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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2020-09-13 20:55:48 UTC

HMDB ID

HMDB0001097

Secondary Accession Numbers

HMDB01097

Metabolite Identification

Common Name

Protoporphyrinogen IX

Description

Protoporphyrinogen IX is an intermediate in heme biosynthesis. It is a porphyrinogen in which two pyrrole rings each have one methyl and one propionate side chain, and the other two pyrrole rings each have one methyl and one vinyl side chain. Fifteen isomers are possible but only one, type IX, occurs naturally. Protoporphyrinogen is produced by oxidative decarboxylation of coproporphyrinogen. Under certain conditions, protoporphyrinogen IX can act as a phototoxin, a neurotoxin, and a metabotoxin. A phototoxin leads to cell damage upon exposure to light. A neurotoxin causes damage to nerve cells and nerve tissues. A metabotoxin is an endogenously produced metabolite that causes adverse health effects at chronically high levels. Chronically high levels of porphyrins are associated with porphyrias such as porphyria variegate, acute intermittent porphyria, and hereditary coproporphyria (HCP). In particular, protoporphyrinogen IX is accumulated and excreted excessively in the feces in acute intermittent porphyria, protoporphyria, and variegate porphyria. There are several types of porphyrias (most are inherited). Hepatic porphyrias are characterized by acute neurological attacks (seizures, psychosis, extreme back and abdominal pain, and an acute polyneuropathy), while the erythropoietic forms present with skin problems (usually a light-sensitive blistering rash and increased hair growth). The neurotoxicity of porphyrins may be due to their selective interactions with tubulin, which disrupt microtubule formation and cause neural malformations (PMID: 3441503 ).

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

  Mrv1652303021823532D          

 42 46  0  0  0  0            999 V2000
   -1.6485    0.7079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7095    1.6679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.0852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7305    1.6679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6695    0.7079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0870   -0.0015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6695   -0.7111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7305   -1.6712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.0885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7095   -1.6712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6485   -0.7111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0660   -0.0015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8556    0.8540    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8556   -0.8572    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8347   -0.8572    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0243    1.4592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8211    1.6727    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4609    2.0435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6744    2.8404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0661   -1.4624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8629   -1.6759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0243   -1.4624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8211   -1.6759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4399    2.0435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6533    2.8404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4502    3.0539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0661    1.4592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8629    1.6727    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0764    2.4696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4399   -2.0467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6533   -2.8436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4502   -3.0571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4609   -2.0467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6744   -2.8436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4713   -3.0571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4605   -4.0675    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6637   -3.8539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0804   -4.4373    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1014   -4.4373    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6847   -3.8539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4815   -4.0675    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8347    0.8540    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1 42  1  0  0  0  0
 16  1  2  0  0  0  0
 12  1  1  0  0  0  0
  2  3  1  0  0  0  0
 42  2  1  0  0  0  0
 24  2  2  0  0  0  0
  3  4  1  0  0  0  0
  4 13  1  0  0  0  0
 18  4  2  0  0  0  0
  5  6  1  0  0  0  0
 13  5  1  0  0  0  0
 27  5  2  0  0  0  0
  6  7  1  0  0  0  0
  7 14  1  0  0  0  0
  7 20  2  0  0  0  0
  8  9  1  0  0  0  0
 33  8  2  0  0  0  0
 14  8  1  0  0  0  0
 10  9  1  0  0  0  0
 15 10  1  0  0  0  0
 30 10  2  0  0  0  0
 11 12  1  0  0  0  0
 15 11  1  0  0  0  0
 22 11  2  0  0  0  0
 24 16  1  0  0  0  0
 16 17  1  0  0  0  0
 18 27  1  0  0  0  0
 18 19  1  0  0  0  0
 20 33  1  0  0  0  0
 20 21  1  0  0  0  0
 22 30  1  0  0  0  0
 22 23  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 37  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 40  1  0  0  0  0
 37 36  1  0  0  0  0
 37 38  2  0  0  0  0
 40 39  1  0  0  0  0
 40 41  2  0  0  0  0
M  END

HMDB0001097
     RDKit          3D
Protoporphyrinogen IX
 82 86  0  0  0  0  0  0  0  0999 V2000
    4.5727   -4.6923    1.6814 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5636   -4.5750    0.8724 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3981   -3.7003    1.1058 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3754   -2.3913    1.5808 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1005   -2.0036    1.7076 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2933   -3.0119    1.3216 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0883   -4.0911    0.9409 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6462   -5.4515    0.4371 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2090   -3.0251    1.1919 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8346   -1.8534    0.4888 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2731   -0.7505   -0.0276 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2793    0.0137   -0.5208 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4849   -0.6280   -0.3103 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8774   -0.2103   -0.6967 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0632   -0.5271   -2.1427 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4186   -0.1600   -2.6381 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3510   -0.9618   -2.4097 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7023    0.9989   -3.3256 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2298   -1.8118    0.3280 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2417   -2.8315    0.7626 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2306    1.3640   -1.1625 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9698    2.1524   -0.9995 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2984    1.7386   -1.2751 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1145    2.7215   -0.8790 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3966    3.7847   -0.3575 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8857    5.1031    0.1985 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9532    3.4225   -0.4317 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0443    4.2870    0.0807 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4222    4.2103    1.4924 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8475    2.9837    2.1159 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3043    1.8829    1.9453 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9516    2.9553    2.9936 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6411    2.7385   -0.8118 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2415    1.4734   -0.2559 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8888    0.7689    0.8380 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6536   -0.3439    0.8281 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4998   -0.3491   -0.2677 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5195   -1.3689   -0.7007 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2418    0.8097   -0.9610 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9949    1.1886   -2.1607 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3740    2.3928   -2.4748 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6123   -1.5159    1.8094 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6631   -4.1637    2.6109 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4128   -5.3578    1.4584 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5656   -5.1619   -0.0518 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7555   -1.0077    2.1160 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4096   -6.1697    0.7542 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4680   -5.4185   -0.6586 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3007   -5.6651    0.9369 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6469   -3.1812    2.1813 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5513   -3.9732    0.6617 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1976   -0.5156   -0.0610 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5775   -0.7721   -0.0558 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0335    0.8653   -0.4640 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8878   -1.6096   -2.3285 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3506    0.0189   -2.7582 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3271    1.7238   -2.9853 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8513   -3.4717    1.5620 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0791   -2.2564    1.2098 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6347   -3.4029   -0.1008 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0925    1.9246   -0.6793 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5187    1.3676   -2.2075 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5766    0.7914   -1.7852 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1446    5.8881    0.0152 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7955    5.3710   -0.3816 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1802    5.0034    1.2543 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9689    4.0710   -0.5293 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8374    5.3655   -0.1631 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6017    4.7145    2.1126 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2594    4.9924    1.6235 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1247    3.7945    3.5289 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0445    3.6374   -0.3071 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9485    2.9170   -1.8491 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1464    1.0519    1.6108 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0023   -2.1502   -1.2978 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0370   -1.7605    0.1807 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2717   -0.8868   -1.3523 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2357    0.3495   -2.8242 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1827    3.2662   -1.8906 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9279    2.5499   -3.3891 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8646   -1.2967    2.8362 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4965   -2.1788    1.5555 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  6  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 13 19  1  0
 19 20  1  0
 12 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 25 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  2  0
 30 32  1  0
 24 33  1  0
 33 34  1  0
 34 35  1  0
 35 36  1  0
 36 37  2  0
 37 38  1  0
 37 39  1  0
 39 40  1  0
 40 41  2  3
 36 42  1  0
  7  3  1  0
 19 10  2  0
 27 22  2  0
 39 34  2  0
 42  4  1  0
  1 43  1  0
  1 44  1  0
  2 45  1  0
  5 46  1  0
  8 47  1  0
  8 48  1  0
  8 49  1  0
  9 50  1  0
  9 51  1  0
 11 52  1  0
 14 53  1  0
 14 54  1  0
 15 55  1  0
 15 56  1  0
 18 57  1  0
 20 58  1  0
 20 59  1  0
 20 60  1  0
 21 61  1  0
 21 62  1  0
 23 63  1  0
 26 64  1  0
 26 65  1  0
 26 66  1  0
 28 67  1  0
 28 68  1  0
 29 69  1  0
 29 70  1  0
 32 71  1  0
 33 72  1  0
 33 73  1  0
 35 74  1  0
 38 75  1  0
 38 76  1  0
 38 77  1  0
 40 78  1  0
 41 79  1  0
 41 80  1  0
 42 81  1  0
 42 82  1  0
M  END

  Mrv1652303021823532D          

 42 46  0  0  0  0            999 V2000
   -1.6485    0.7079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7095    1.6679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.0852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7305    1.6679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6695    0.7079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0870   -0.0015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6695   -0.7111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7305   -1.6712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.0885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7095   -1.6712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6485   -0.7111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0660   -0.0015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8556    0.8540    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8556   -0.8572    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8347   -0.8572    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0243    1.4592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8211    1.6727    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4609    2.0435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6744    2.8404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0661   -1.4624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8629   -1.6759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0243   -1.4624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8211   -1.6759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4399    2.0435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6533    2.8404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4502    3.0539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0661    1.4592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8629    1.6727    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0764    2.4696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4399   -2.0467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6533   -2.8436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4502   -3.0571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4609   -2.0467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6744   -2.8436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4713   -3.0571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4605   -4.0675    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6637   -3.8539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0804   -4.4373    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1014   -4.4373    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6847   -3.8539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4815   -4.0675    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8347    0.8540    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1 42  1  0  0  0  0
 16  1  2  0  0  0  0
 12  1  1  0  0  0  0
  2  3  1  0  0  0  0
 42  2  1  0  0  0  0
 24  2  2  0  0  0  0
  3  4  1  0  0  0  0
  4 13  1  0  0  0  0
 18  4  2  0  0  0  0
  5  6  1  0  0  0  0
 13  5  1  0  0  0  0
 27  5  2  0  0  0  0
  6  7  1  0  0  0  0
  7 14  1  0  0  0  0
  7 20  2  0  0  0  0
  8  9  1  0  0  0  0
 33  8  2  0  0  0  0
 14  8  1  0  0  0  0
 10  9  1  0  0  0  0
 15 10  1  0  0  0  0
 30 10  2  0  0  0  0
 11 12  1  0  0  0  0
 15 11  1  0  0  0  0
 22 11  2  0  0  0  0
 24 16  1  0  0  0  0
 16 17  1  0  0  0  0
 18 27  1  0  0  0  0
 18 19  1  0  0  0  0
 20 33  1  0  0  0  0
 20 21  1  0  0  0  0
 22 30  1  0  0  0  0
 22 23  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 37  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 40  1  0  0  0  0
 37 36  1  0  0  0  0
 37 38  2  0  0  0  0
 40 39  1  0  0  0  0
 40 41  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0001097

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1=C2CC3=C(C)C(C=C)=C(CC4=C(C)C(C=C)=C(CC5=C(C)C(CCC(O)=O)=C(CC(N2)=C1CCC(O)=O)N5)N4)N3

> <INCHI_IDENTIFIER>
InChI=1S/C34H40N4O4/c1-7-21-17(3)25-13-26-19(5)23(9-11-33(39)40)31(37-26)16-32-24(10-12-34(41)42)20(6)28(38-32)15-30-22(8-2)18(4)27(36-30)14-29(21)35-25/h7-8,35-38H,1-2,9-16H2,3-6H3,(H,39,40)(H,41,42)

> <INCHI_KEY>
UHSGPDMIQQYNAX-UHFFFAOYSA-N

> <FORMULA>
C34H40N4O4

> <MOLECULAR_WEIGHT>
568.7058

> <EXACT_MASS>
568.304955788

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
82

> <JCHEM_AVERAGE_POLARIZABILITY>
64.5199264797442

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-[20-(2-carboxyethyl)-9,14-diethenyl-5,10,15,19-tetramethyl-21,22,23,24-tetraazapentacyclo[16.2.1.1^{3,6}.1^{8,11}.1^{13,16}]tetracosa-1(20),3,5,8,10,13,15,18-octaen-4-yl]propanoic acid

> <ALOGPS_LOGP>
3.44

> <JCHEM_LOGP>
6.200009445999999

> <ALOGPS_LOGS>
-5.01

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
4.67011788729448

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.0668900795671075

> <JCHEM_POLAR_SURFACE_AREA>
137.76

> <JCHEM_REFRACTIVITY>
169.41620000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.51e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-[20-(2-carboxyethyl)-9,14-diethenyl-5,10,15,19-tetramethyl-21,22,23,24-tetraazapentacyclo[16.2.1.1^{3,6}.1^{8,11}.1^{13,16}]tetracosa-1(20),3,5,8,10,13,15,18-octaen-4-yl]propanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0001097
     RDKit          3D
Protoporphyrinogen IX
 82 86  0  0  0  0  0  0  0  0999 V2000
    4.5727   -4.6923    1.6814 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5636   -4.5750    0.8724 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3981   -3.7003    1.1058 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3754   -2.3913    1.5808 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1005   -2.0036    1.7076 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2933   -3.0119    1.3216 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0883   -4.0911    0.9409 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6462   -5.4515    0.4371 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2090   -3.0251    1.1919 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8346   -1.8534    0.4888 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2731   -0.7505   -0.0276 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2793    0.0137   -0.5208 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4849   -0.6280   -0.3103 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8774   -0.2103   -0.6967 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0632   -0.5271   -2.1427 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4186   -0.1600   -2.6381 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3510   -0.9618   -2.4097 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7023    0.9989   -3.3256 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2298   -1.8118    0.3280 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2417   -2.8315    0.7626 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2306    1.3640   -1.1625 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9698    2.1524   -0.9995 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2984    1.7386   -1.2751 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1145    2.7215   -0.8790 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3966    3.7847   -0.3575 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8857    5.1031    0.1985 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9532    3.4225   -0.4317 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0443    4.2870    0.0807 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4222    4.2103    1.4924 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8475    2.9837    2.1159 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3043    1.8829    1.9453 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9516    2.9553    2.9936 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6411    2.7385   -0.8118 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2415    1.4734   -0.2559 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8888    0.7689    0.8380 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6536   -0.3439    0.8281 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4998   -0.3491   -0.2677 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5195   -1.3689   -0.7007 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2418    0.8097   -0.9610 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9949    1.1886   -2.1607 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3740    2.3928   -2.4748 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6123   -1.5159    1.8094 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6631   -4.1637    2.6109 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4128   -5.3578    1.4584 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5656   -5.1619   -0.0518 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7555   -1.0077    2.1160 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4096   -6.1697    0.7542 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4680   -5.4185   -0.6586 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3007   -5.6651    0.9369 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6469   -3.1812    2.1813 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5513   -3.9732    0.6617 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1976   -0.5156   -0.0610 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5775   -0.7721   -0.0558 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0335    0.8653   -0.4640 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8878   -1.6096   -2.3285 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3506    0.0189   -2.7582 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3271    1.7238   -2.9853 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8513   -3.4717    1.5620 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0791   -2.2564    1.2098 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6347   -3.4029   -0.1008 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0925    1.9246   -0.6793 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5187    1.3676   -2.2075 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5766    0.7914   -1.7852 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1446    5.8881    0.0152 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7955    5.3710   -0.3816 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1802    5.0034    1.2543 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9689    4.0710   -0.5293 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8374    5.3655   -0.1631 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6017    4.7145    2.1126 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2594    4.9924    1.6235 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1247    3.7945    3.5289 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0445    3.6374   -0.3071 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9485    2.9170   -1.8491 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1464    1.0519    1.6108 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0023   -2.1502   -1.2978 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0370   -1.7605    0.1807 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2717   -0.8868   -1.3523 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2357    0.3495   -2.8242 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1827    3.2662   -1.8906 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9279    2.5499   -3.3891 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8646   -1.2967    2.8362 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4965   -2.1788    1.5555 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  6  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 13 19  1  0
 19 20  1  0
 12 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 25 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  2  0
 30 32  1  0
 24 33  1  0
 33 34  1  0
 34 35  1  0
 35 36  1  0
 36 37  2  0
 37 38  1  0
 37 39  1  0
 39 40  1  0
 40 41  2  3
 36 42  1  0
  7  3  1  0
 19 10  2  0
 27 22  2  0
 39 34  2  0
 42  4  1  0
  1 43  1  0
  1 44  1  0
  2 45  1  0
  5 46  1  0
  8 47  1  0
  8 48  1  0
  8 49  1  0
  9 50  1  0
  9 51  1  0
 11 52  1  0
 14 53  1  0
 14 54  1  0
 15 55  1  0
 15 56  1  0
 18 57  1  0
 20 58  1  0
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 20 60  1  0
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 23 63  1  0
 26 64  1  0
 26 65  1  0
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 28 67  1  0
 28 68  1  0
 29 69  1  0
 29 70  1  0
 32 71  1  0
 33 72  1  0
 33 73  1  0
 35 74  1  0
 38 75  1  0
 38 76  1  0
 38 77  1  0
 40 78  1  0
 41 79  1  0
 41 80  1  0
 42 81  1  0
 42 82  1  0
M  END

HEADER    PROTEIN                                 02-MAR-18   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-MAR-18         0                                  
HETATM    1  C   UNK     0      -3.077   1.321   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.324   3.113   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000   3.892   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.364   3.113   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.116   1.321   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.896  -0.003   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.116  -1.327   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.364  -3.120   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000  -3.899   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.324  -3.120   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -3.077  -1.327   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -3.856  -0.003   0.000  0.00  0.00           C+0
HETATM   13  N   UNK     0       1.597   1.594   0.000  0.00  0.00           N+0
HETATM   14  N   UNK     0       1.597  -1.600   0.000  0.00  0.00           N+0
HETATM   15  N   UNK     0      -1.558  -1.600   0.000  0.00  0.00           N+0
HETATM   16  C   UNK     0      -3.779   2.724   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -5.266   3.122   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.727   3.815   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.126   5.302   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.857  -2.730   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.344  -3.128   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -3.779  -2.730   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -5.266  -3.128   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -2.688   3.815   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -3.086   5.302   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -4.574   5.701   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       3.857   2.724   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       5.344   3.122   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       5.743   4.610   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -2.688  -3.821   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -3.086  -5.308   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -4.574  -5.707   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       2.727  -3.821   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       3.126  -5.308   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       4.613  -5.707   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      -6.460  -7.593   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0      -4.972  -7.194   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0      -3.883  -8.283   0.000  0.00  0.00           O+0
HETATM   39  O   UNK     0       3.923  -8.283   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0       5.011  -7.194   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0       6.499  -7.593   0.000  0.00  0.00           O+0
HETATM   42  N   UNK     0      -1.558   1.594   0.000  0.00  0.00           N+0
CONECT    1   42   16   12                                                  
CONECT    2    3   42   24                                                  
CONECT    3    2    4                                                       
CONECT    4    3   13   18                                                  
CONECT    5    6   13   27                                                  
CONECT    6    5    7                                                       
CONECT    7    6   14   20                                                  
CONECT    8    9   33   14                                                  
CONECT    9    8   10                                                       
CONECT   10    9   15   30                                                  
CONECT   11   12   15   22                                                  
CONECT   12    1   11                                                       
CONECT   13    4    5                                                       
CONECT   14    7    8                                                       
CONECT   15   10   11                                                       
CONECT   16    1   24   17                                                  
CONECT   17   16                                                            
CONECT   18    4   27   19                                                  
CONECT   19   18                                                            
CONECT   20    7   33   21                                                  
CONECT   21   20                                                            
CONECT   22   11   30   23                                                  
CONECT   23   22                                                            
CONECT   24    2   16   25                                                  
CONECT   25   24   26                                                       
CONECT   26   25                                                            
CONECT   27    5   18   28                                                  
CONECT   28   27   29                                                       
CONECT   29   28                                                            
CONECT   30   10   22   31                                                  
CONECT   31   30   32                                                       
CONECT   32   31   37                                                       
CONECT   33    8   20   34                                                  
CONECT   34   33   35                                                       
CONECT   35   34   40                                                       
CONECT   36   37                                                            
CONECT   37   32   36   38                                                  
CONECT   38   37                                                            
CONECT   39   40                                                            
CONECT   40   35   39   41                                                  
CONECT   41   40                                                            
CONECT   42    1    2                                                       
MASTER        0    0    0    0    0    0    0    0   42    0   92    0
END

COMPND    HMDB0001097
HETATM    1  C1  UNL     1       4.573  -4.692   1.681  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.564  -4.575   0.872  1.00  0.00           C  
HETATM    3  C3  UNL     1       2.398  -3.700   1.106  1.00  0.00           C  
HETATM    4  C4  UNL     1       2.375  -2.391   1.581  1.00  0.00           C  
HETATM    5  N1  UNL     1       1.100  -2.004   1.708  1.00  0.00           N  
HETATM    6  C5  UNL     1       0.293  -3.012   1.322  1.00  0.00           C  
HETATM    7  C6  UNL     1       1.088  -4.091   0.941  1.00  0.00           C  
HETATM    8  C7  UNL     1       0.646  -5.451   0.437  1.00  0.00           C  
HETATM    9  C8  UNL     1      -1.209  -3.025   1.192  1.00  0.00           C  
HETATM   10  C9  UNL     1      -1.835  -1.853   0.489  1.00  0.00           C  
HETATM   11  N2  UNL     1      -1.273  -0.750  -0.028  1.00  0.00           N  
HETATM   12  C10 UNL     1      -2.279   0.014  -0.521  1.00  0.00           C  
HETATM   13  C11 UNL     1      -3.485  -0.628  -0.310  1.00  0.00           C  
HETATM   14  C12 UNL     1      -4.877  -0.210  -0.697  1.00  0.00           C  
HETATM   15  C13 UNL     1      -5.063  -0.527  -2.143  1.00  0.00           C  
HETATM   16  C14 UNL     1      -6.419  -0.160  -2.638  1.00  0.00           C  
HETATM   17  O1  UNL     1      -7.351  -0.962  -2.410  1.00  0.00           O  
HETATM   18  O2  UNL     1      -6.702   0.999  -3.326  1.00  0.00           O  
HETATM   19  C15 UNL     1      -3.230  -1.812   0.328  1.00  0.00           C  
HETATM   20  C16 UNL     1      -4.242  -2.831   0.763  1.00  0.00           C  
HETATM   21  C17 UNL     1      -2.231   1.364  -1.163  1.00  0.00           C  
HETATM   22  C18 UNL     1      -0.970   2.152  -0.999  1.00  0.00           C  
HETATM   23  N3  UNL     1       0.298   1.739  -1.275  1.00  0.00           N  
HETATM   24  C19 UNL     1       1.115   2.722  -0.879  1.00  0.00           C  
HETATM   25  C20 UNL     1       0.397   3.785  -0.357  1.00  0.00           C  
HETATM   26  C21 UNL     1       0.886   5.103   0.198  1.00  0.00           C  
HETATM   27  C22 UNL     1      -0.953   3.423  -0.432  1.00  0.00           C  
HETATM   28  C23 UNL     1      -2.044   4.287   0.081  1.00  0.00           C  
HETATM   29  C24 UNL     1      -2.422   4.210   1.492  1.00  0.00           C  
HETATM   30  C25 UNL     1      -2.848   2.984   2.116  1.00  0.00           C  
HETATM   31  O3  UNL     1      -2.304   1.883   1.945  1.00  0.00           O  
HETATM   32  O4  UNL     1      -3.952   2.955   2.994  1.00  0.00           O  
HETATM   33  C26 UNL     1       2.641   2.739  -0.812  1.00  0.00           C  
HETATM   34  C27 UNL     1       3.241   1.473  -0.256  1.00  0.00           C  
HETATM   35  N4  UNL     1       2.889   0.769   0.838  1.00  0.00           N  
HETATM   36  C28 UNL     1       3.654  -0.344   0.828  1.00  0.00           C  
HETATM   37  C29 UNL     1       4.500  -0.349  -0.268  1.00  0.00           C  
HETATM   38  C30 UNL     1       5.520  -1.369  -0.701  1.00  0.00           C  
HETATM   39  C31 UNL     1       4.242   0.810  -0.961  1.00  0.00           C  
HETATM   40  C32 UNL     1       4.995   1.189  -2.161  1.00  0.00           C  
HETATM   41  C33 UNL     1       5.374   2.393  -2.475  1.00  0.00           C  
HETATM   42  C34 UNL     1       3.612  -1.516   1.809  1.00  0.00           C  
HETATM   43  H1  UNL     1       4.663  -4.164   2.611  1.00  0.00           H  
HETATM   44  H2  UNL     1       5.413  -5.358   1.458  1.00  0.00           H  
HETATM   45  H3  UNL     1       3.566  -5.162  -0.052  1.00  0.00           H  
HETATM   46  H4  UNL     1       0.756  -1.008   2.116  1.00  0.00           H  
HETATM   47  H5  UNL     1       1.410  -6.170   0.754  1.00  0.00           H  
HETATM   48  H6  UNL     1       0.468  -5.418  -0.659  1.00  0.00           H  
HETATM   49  H7  UNL     1      -0.301  -5.665   0.937  1.00  0.00           H  
HETATM   50  H8  UNL     1      -1.647  -3.181   2.181  1.00  0.00           H  
HETATM   51  H9  UNL     1      -1.551  -3.973   0.662  1.00  0.00           H  
HETATM   52  H10 UNL     1      -0.198  -0.516  -0.061  1.00  0.00           H  
HETATM   53  H11 UNL     1      -5.577  -0.772  -0.056  1.00  0.00           H  
HETATM   54  H12 UNL     1      -5.033   0.865  -0.464  1.00  0.00           H  
HETATM   55  H13 UNL     1      -4.888  -1.610  -2.329  1.00  0.00           H  
HETATM   56  H14 UNL     1      -4.351   0.019  -2.758  1.00  0.00           H  
HETATM   57  H15 UNL     1      -7.327   1.724  -2.985  1.00  0.00           H  
HETATM   58  H16 UNL     1      -3.851  -3.472   1.562  1.00  0.00           H  
HETATM   59  H17 UNL     1      -5.079  -2.256   1.210  1.00  0.00           H  
HETATM   60  H18 UNL     1      -4.635  -3.403  -0.101  1.00  0.00           H  
HETATM   61  H19 UNL     1      -3.093   1.925  -0.679  1.00  0.00           H  
HETATM   62  H20 UNL     1      -2.519   1.368  -2.207  1.00  0.00           H  
HETATM   63  H21 UNL     1       0.577   0.791  -1.785  1.00  0.00           H  
HETATM   64  H22 UNL     1       0.145   5.888   0.015  1.00  0.00           H  
HETATM   65  H23 UNL     1       1.795   5.371  -0.382  1.00  0.00           H  
HETATM   66  H24 UNL     1       1.180   5.003   1.254  1.00  0.00           H  
HETATM   67  H25 UNL     1      -2.969   4.071  -0.529  1.00  0.00           H  
HETATM   68  H26 UNL     1      -1.837   5.365  -0.163  1.00  0.00           H  
HETATM   69  H27 UNL     1      -1.602   4.714   2.113  1.00  0.00           H  
HETATM   70  H28 UNL     1      -3.259   4.992   1.624  1.00  0.00           H  
HETATM   71  H29 UNL     1      -4.125   3.795   3.529  1.00  0.00           H  
HETATM   72  H30 UNL     1       3.045   3.637  -0.307  1.00  0.00           H  
HETATM   73  H31 UNL     1       2.949   2.917  -1.849  1.00  0.00           H  
HETATM   74  H32 UNL     1       2.146   1.052   1.611  1.00  0.00           H  
HETATM   75  H33 UNL     1       5.002  -2.150  -1.298  1.00  0.00           H  
HETATM   76  H34 UNL     1       6.037  -1.760   0.181  1.00  0.00           H  
HETATM   77  H35 UNL     1       6.272  -0.887  -1.352  1.00  0.00           H  
HETATM   78  H36 UNL     1       5.236   0.350  -2.824  1.00  0.00           H  
HETATM   79  H37 UNL     1       5.183   3.266  -1.891  1.00  0.00           H  
HETATM   80  H38 UNL     1       5.928   2.550  -3.389  1.00  0.00           H  
HETATM   81  H39 UNL     1       3.865  -1.297   2.836  1.00  0.00           H  
HETATM   82  H40 UNL     1       4.497  -2.179   1.556  1.00  0.00           H  
CONECT    1    2    2   43   44
CONECT    2    3   45
CONECT    3    4    4    7
CONECT    4    5   42
CONECT    5    6   46
CONECT    6    7    7    9
CONECT    7    8
CONECT    8   47   48   49
CONECT    9   10   50   51
CONECT   10   11   19   19
CONECT   11   12   52
CONECT   12   13   13   21
CONECT   13   14   19
CONECT   14   15   53   54
CONECT   15   16   55   56
CONECT   16   17   17   18
CONECT   18   57
CONECT   19   20
CONECT   20   58   59   60
CONECT   21   22   61   62
CONECT   22   23   27   27
CONECT   23   24   63
CONECT   24   25   25   33
CONECT   25   26   27
CONECT   26   64   65   66
CONECT   27   28
CONECT   28   29   67   68
CONECT   29   30   69   70
CONECT   30   31   31   32
CONECT   32   71
CONECT   33   34   72   73
CONECT   34   35   39   39
CONECT   35   36   74
CONECT   36   37   37   42
CONECT   37   38   39
CONECT   38   75   76   77
CONECT   39   40
CONECT   40   41   41   78
CONECT   41   79   80
CONECT   42   81   82
END

HMDB0001097
     RDKit          3D
Protoporphyrinogen IX
 82 86  0  0  0  0  0  0  0  0999 V2000
    4.5727   -4.6923    1.6814 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5636   -4.5750    0.8724 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3981   -3.7003    1.1058 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3754   -2.3913    1.5808 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1005   -2.0036    1.7076 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2933   -3.0119    1.3216 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0883   -4.0911    0.9409 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6462   -5.4515    0.4371 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2090   -3.0251    1.1919 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8346   -1.8534    0.4888 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2731   -0.7505   -0.0276 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2793    0.0137   -0.5208 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4849   -0.6280   -0.3103 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8774   -0.2103   -0.6967 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0632   -0.5271   -2.1427 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4186   -0.1600   -2.6381 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3510   -0.9618   -2.4097 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7023    0.9989   -3.3256 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2298   -1.8118    0.3280 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2417   -2.8315    0.7626 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2306    1.3640   -1.1625 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9698    2.1524   -0.9995 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2984    1.7386   -1.2751 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1145    2.7215   -0.8790 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3966    3.7847   -0.3575 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8857    5.1031    0.1985 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9532    3.4225   -0.4317 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0443    4.2870    0.0807 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4222    4.2103    1.4924 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8475    2.9837    2.1159 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3043    1.8829    1.9453 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9516    2.9553    2.9936 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6411    2.7385   -0.8118 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2415    1.4734   -0.2559 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8888    0.7689    0.8380 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6536   -0.3439    0.8281 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4998   -0.3491   -0.2677 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5195   -1.3689   -0.7007 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2418    0.8097   -0.9610 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9949    1.1886   -2.1607 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3740    2.3928   -2.4748 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6123   -1.5159    1.8094 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6631   -4.1637    2.6109 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4128   -5.3578    1.4584 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5656   -5.1619   -0.0518 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7555   -1.0077    2.1160 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4096   -6.1697    0.7542 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4680   -5.4185   -0.6586 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3007   -5.6651    0.9369 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6469   -3.1812    2.1813 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5513   -3.9732    0.6617 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1976   -0.5156   -0.0610 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5775   -0.7721   -0.0558 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0335    0.8653   -0.4640 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8878   -1.6096   -2.3285 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3506    0.0189   -2.7582 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3271    1.7238   -2.9853 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8513   -3.4717    1.5620 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0791   -2.2564    1.2098 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6347   -3.4029   -0.1008 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0925    1.9246   -0.6793 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5187    1.3676   -2.2075 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5766    0.7914   -1.7852 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1446    5.8881    0.0152 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7955    5.3710   -0.3816 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1802    5.0034    1.2543 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9689    4.0710   -0.5293 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8374    5.3655   -0.1631 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6017    4.7145    2.1126 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2594    4.9924    1.6235 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1247    3.7945    3.5289 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0445    3.6374   -0.3071 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9485    2.9170   -1.8491 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1464    1.0519    1.6108 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0023   -2.1502   -1.2978 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0370   -1.7605    0.1807 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2717   -0.8868   -1.3523 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2357    0.3495   -2.8242 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1827    3.2662   -1.8906 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9279    2.5499   -3.3891 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8646   -1.2967    2.8362 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4965   -2.1788    1.5555 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  6  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 13 19  1  0
 19 20  1  0
 12 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 25 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  2  0
 30 32  1  0
 24 33  1  0
 33 34  1  0
 34 35  1  0
 35 36  1  0
 36 37  2  0
 37 38  1  0
 37 39  1  0
 39 40  1  0
 40 41  2  3
 36 42  1  0
  7  3  1  0
 19 10  2  0
 27 22  2  0
 39 34  2  0
 42  4  1  0
  1 43  1  0
  1 44  1  0
  2 45  1  0
  5 46  1  0
  8 47  1  0
  8 48  1  0
  8 49  1  0
  9 50  1  0
  9 51  1  0
 11 52  1  0
 14 53  1  0
 14 54  1  0
 15 55  1  0
 15 56  1  0
 18 57  1  0
 20 58  1  0
 20 59  1  0
 20 60  1  0
 21 61  1  0
 21 62  1  0
 23 63  1  0
 26 64  1  0
 26 65  1  0
 26 66  1  0
 28 67  1  0
 28 68  1  0
 29 69  1  0
 29 70  1  0
 32 71  1  0
 33 72  1  0
 33 73  1  0
 35 74  1  0
 38 75  1  0
 38 76  1  0
 38 77  1  0
 40 78  1  0
 41 79  1  0
 41 80  1  0
 42 81  1  0
 42 82  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
7,12-Diethenyl-3,8,13,17-tetramethyl-5,10,15,20,22,24-hexahydroporphyrin-2,18-dipropanoic acid	ChEBI
7,12-Diethenyl-3,8,13,17-tetramethyl-5,10,15,20,22,24-hexahydroporphyrin-2,18-dipropanoate	Generator
5,10,15,20,22,24-Hexahydro protoporphyrin IX deriv.	HMDB
7,12-Diethenyl-5,10,15,20,22,24-hexahydro-3,8,13,17-tetramethyl-21H,23H-porphine-2,18-dipropanoate	HMDB
7,12-Diethenyl-5,10,15,20,22,24-hexahydro-3,8,13,17-tetramethyl-21H,23H-porphine-2,18-dipropanoic acid	HMDB
Protoporphyrinogen	HMDB
Protoporphyrinogen-IX	HMDB

Chemical Formula

C₃₄H₄₀N₄O₄

Average Molecular Weight

568.7058

Monoisotopic Molecular Weight

568.304955788

IUPAC Name

3-[20-(2-carboxyethyl)-9,14-diethenyl-5,10,15,19-tetramethyl-21,22,23,24-tetraazapentacyclo[16.2.1.1^{3,6}.1^{8,11}.1^{13,16}]tetracosa-1(20),3,5,8,10,13,15,18-octaen-4-yl]propanoic acid

Traditional Name

3-[20-(2-carboxyethyl)-9,14-diethenyl-5,10,15,19-tetramethyl-21,22,23,24-tetraazapentacyclo[16.2.1.1^{3,6}.1^{8,11}.1^{13,16}]tetracosa-1(20),3,5,8,10,13,15,18-octaen-4-yl]propanoic acid

CAS Registry Number

7412-77-3

SMILES

CC1=C2CC3=C(C)C(C=C)=C(CC4=C(C)C(C=C)=C(CC5=C(C)C(CCC(O)=O)=C(CC(N2)=C1CCC(O)=O)N5)N4)N3

InChI Identifier

InChI=1S/C34H40N4O4/c1-7-21-17(3)25-13-26-19(5)23(9-11-33(39)40)31(37-26)16-32-24(10-12-34(41)42)20(6)28(38-32)15-30-22(8-2)18(4)27(36-30)14-29(21)35-25/h7-8,35-38H,1-2,9-16H2,3-6H3,(H,39,40)(H,41,42)

InChI Key

UHSGPDMIQQYNAX-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as porphyrins. Porphyrins are compounds containing a fundamental skeleton of four pyrrole nuclei united through the alpha-positions by four methine groups to form a macrocyclic structure.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Tetrapyrroles and derivatives

Sub Class

Porphyrins

Direct Parent

Porphyrins

Alternative Parents

Substituents

Porphyrin
Dicarboxylic acid or derivatives
Substituted pyrrole
Pyrrole
Heteroaromatic compound
Azacycle
Carboxylic acid
Carboxylic acid derivative
Carbonyl group
Organopnictogen compound
Organic oxygen compound
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Hydrocarbon derivative
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

porphyrinogens (CHEBI:15435 )

Ontology

Physiological effect

Health effect

Genetic disorder

Inborn errors of metabolism

Porphyria (HMDB: HMDB0001097)
Hereditary coproporphyria (HMDB: HMDB0001097)

Disposition

Biological location

Cellular substructure

Organelle

Mitochondrion (HMDB: HMDB0001097)

Organ

Liver (HMDB: HMDB0001097)
Placenta (HMDB: HMDB0001097)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0001097)

Source

Endogenous

Endogenous (HMDB: HMDB0001097)

Plant

Animal

Animal (HMDB: HMDB0001097)

Exogenous

Food

Food (HMDB: HMDB0001097)

Animal origin

Poultry

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Herbs and Spices (FooDB: FOOD00866)

Nut

Almond (FooDB: FOOD00148)
Brazil nut (FooDB: FOOD00024)
Cashew nut (FooDB: FOOD00011)
Chestnut (FooDB: FOOD00045)
Hazelnut (FooDB: FOOD00376)
Peanut (FooDB: FOOD00016)
Pecan nut (FooDB: FOOD00044)
Pine nut (FooDB: FOOD00138)
Pistachio (FooDB: FOOD00140)
Walnut (FooDB: FOOD00608)
Acorn (FooDB: FOOD00282)
Beech nut (FooDB: FOOD00299)
Butternut (FooDB: FOOD00316)
Chinese chestnut (FooDB: FOOD00331)
European chestnut (FooDB: FOOD00363)
Hickory nut (FooDB: FOOD00377)
Macadamia nut (FooDB: FOOD00525)
Mixed nuts (FooDB: FOOD00771)
Pili nut (FooDB: FOOD00432)
Colorado pinyon (FooDB: FOOD00433)
Black walnut (FooDB: FOOD00093)
Common walnut (FooDB: FOOD00094)
Japanese chestnut (FooDB: FOOD00385)
Common hazelnut (FooDB: FOOD00062)
Macadamia nut (M. tetraphylla) (FooDB: FOOD00225)
Japanese walnut (FooDB: FOOD00240)
Nuts (FooDB: FOOD00869)

Fruit

Pome

Drupe

Apricot (FooDB: FOOD00144)
Prunus (Cherry, Plum) (FooDB: FOOD00143)
Nectarine (FooDB: FOOD00229)
Peach (FooDB: FOOD00149)
European plum (FooDB: FOOD00147)
Sour cherry (FooDB: FOOD00146)
Sweet cherry (FooDB: FOOD00145)
Common chokecherry (FooDB: FOOD00562)
Peach (var.) (FooDB: FOOD00230)

Tropical fruit

Berry

Bilberry (FooDB: FOOD00193)
Rubus (Blackberry, Raspberry) (FooDB: FOOD00160)
Vaccinium (Blueberry, Cranberry, Huckleberry) (FooDB: FOOD00188)
Blackcurrant (FooDB: FOOD00155)
Redcurrant (FooDB: FOOD00156)
Elderberry (FooDB: FOOD00358)
Gooseberry (FooDB: FOOD00157)
Grape (FooDB: FOOD00369)
Lingonberry (FooDB: FOOD00194)
Loganberry (FooDB: FOOD00400)
Strawberry (FooDB: FOOD00083)
Boysenberry (FooDB: FOOD00542)
American cranberry (FooDB: FOOD00192)
Common grape (FooDB: FOOD00204)
Strawberry guava (FooDB: FOOD00482)
Black mulberry (FooDB: FOOD00117)
Red raspberry (FooDB: FOOD00162)
Muscadine grape (FooDB: FOOD00203)
Salmonberry (FooDB: FOOD00456)
Alaska blueberry (FooDB: FOOD00380)
Sea-buckthornberry (FooDB: FOOD00087)
Black elderberry (FooDB: FOOD00166)
Black crowberry (FooDB: FOOD00075)
Black huckleberry (FooDB: FOOD00084)
Mulberry (FooDB: FOOD00116)
Black chokeberry (FooDB: FOOD00136)
Cloudberry (FooDB: FOOD00161)
Black raspberry (FooDB: FOOD00163)
Rowanberry (FooDB: FOOD00176)
Lowbush blueberry (FooDB: FOOD00189)
Sparkleberry (FooDB: FOOD00190)
Highbush blueberry (FooDB: FOOD00191)
Arctic blackberry (FooDB: FOOD00207)
Bayberry (FooDB: FOOD00209)
Elliott's blueberry (FooDB: FOOD00210)
Canada blueberry (FooDB: FOOD00211)
Bog bilberry (FooDB: FOOD00212)
Buffalo currant (FooDB: FOOD00213)
European cranberry (FooDB: FOOD00217)
Deerberry (FooDB: FOOD00218)
Cascade huckleberry (FooDB: FOOD00220)
Oval-leaf huckleberry (FooDB: FOOD00221)
Evergreen huckleberry (FooDB: FOOD00222)
Red huckleberry (FooDB: FOOD00223)
Summer grape (FooDB: FOOD00227)
Fox grape (FooDB: FOOD00228)
Half-highbush blueberry (FooDB: FOOD00248)
Jostaberry (FooDB: FOOD00257)
Sweet rowanberry (FooDB: FOOD00265)
Skunk currant (FooDB: FOOD00267)
Squashberry (FooDB: FOOD00344)
Ohelo berry (FooDB: FOOD00419)
Chinese bayberry (FooDB: FOOD00852)
Saskatoon berry (FooDB: FOOD00884)
Nanking cherry (FooDB: FOOD00885)

Other fruit

Date (FooDB: FOOD00135)
Fig (FooDB: FOOD00081)
Jujube (FooDB: FOOD00388)

Citrus

Grapefruit (FooDB: FOOD00256)
Lemon (FooDB: FOOD00054)
Lime (FooDB: FOOD00053)
Sweet orange (FooDB: FOOD00057)
Mandarin orange (Clementine, Tangerine) (FooDB: FOOD00056)
Persian lime (FooDB: FOOD00543)
Pummelo (FooDB: FOOD00055)
Grapefruit/Pummelo hybrid (FooDB: FOOD00255)
Citrus (FooDB: FOOD00859)

Fruits (FooDB: FOOD00871)

Vegetable

Shoot vegetable

Fruit vegetable

Eggplant (FooDB: FOOD00174)
Avocado (FooDB: FOOD00130)
Groundcherry (FooDB: FOOD00371)
Olive (FooDB: FOOD00121)
Pepper (FooDB: FOOD00040)
Garden tomato (FooDB: FOOD00171)
Mexican groundcherry (FooDB: FOOD00491)
Green bell pepper (FooDB: FOOD00877)
Yellow bell pepper (FooDB: FOOD00878)
Red bell pepper (FooDB: FOOD00880)
Italian sweet red pepper (FooDB: FOOD00881)
Garden tomato (var.) (FooDB: FOOD00173)
Cherry tomato (FooDB: FOOD00172)
Pepper (C. baccatum) (FooDB: FOOD00231)
Pepper (C. chinense) (FooDB: FOOD00232)
Pepper (Capsicum) (FooDB: FOOD00233)
Pepper (C. frutescens) (FooDB: FOOD00428)
Pepper (C. pubescens) (FooDB: FOOD00849)
Orange bell pepper (FooDB: FOOD00879)

Root vegetable

Cabbage

Leaf vegetable

Lettuce (FooDB: FOOD00095)
Swiss chard (FooDB: FOOD00237)
Garden cress (FooDB: FOOD00099)
Endive (FooDB: FOOD00048)
Spinach (FooDB: FOOD00178)
Common beet (FooDB: FOOD00025)
Garland chrysanthemum (FooDB: FOOD00333)
Jute (FooDB: FOOD00389)
Lambsquarters (FooDB: FOOD00394)
New Zealand spinach (FooDB: FOOD00415)
Swamp cabbage (FooDB: FOOD00091)
Rocket salad (ssp.) (FooDB: FOOD00077)
Yautia (FooDB: FOOD00510)
Romaine lettuce (FooDB: FOOD00888)
Rocket salad (FooDB: FOOD00244)
Chicory leaves (FooDB: FOOD00250)
Corn salad (FooDB: FOOD00340)
Malabar spinach (FooDB: FOOD00404)
Ostrich fern (FooDB: FOOD00556)
Green vegetables (FooDB: FOOD00872)

Mushroom

Tuber

Onion-family vegetable

Leek (FooDB: FOOD00007)
Allium (FooDB: FOOD00005)
Wild leek (FooDB: FOOD00396)
Shallot (FooDB: FOOD00243)
Garden onion (FooDB: FOOD00006)
Garden onion (var.) (FooDB: FOOD00226)
Onion-family vegetables (FooDB: FOOD00855)
Green onion (FooDB: FOOD00963)
Red onion (FooDB: FOOD00962)

Other vegetable

Okra (FooDB: FOOD00420)
Horseradish tree (FooDB: FOOD00379)
Sacred lotus (FooDB: FOOD00402)
Tree fern (FooDB: FOOD00797)
Chinese water chestnut (FooDB: FOOD00332)
Nopal (FooDB: FOOD00416)
Carob (FooDB: FOOD00321)
Agave (FooDB: FOOD00563)
Narrowleaf cattail (FooDB: FOOD00564)
Giant butterbur (FooDB: FOOD00314)
Sesbania flower (FooDB: FOOD00469)

Stalk vegetable

Brassica

Brassicas (FooDB: FOOD00857)

Cereal and cereal product

Other bread

Other bread (FooDB: FOOD00269)

Cereal

Cereal product

Dough

Sourdough (FooDB: FOOD00275)

Cereals and cereal products (FooDB: FOOD00858)

Pulse

Bean

Lentil

Lentils (FooDB: FOOD00098)

Pea

Other pulse

White lupine (FooDB: FOOD00403)
Lupine (FooDB: FOOD00104)

Pulses (FooDB: FOOD00867)

Soy

Soy bean (FooDB: FOOD00085)

Soy product

Other soy product (FooDB: FOOD00271)

Abalone (FooDB: FOOD00279)
Conch (FooDB: FOOD00611)

Gourd

Chayote (FooDB: FOOD00325)
Cucumber (FooDB: FOOD00065)
Muskmelon (FooDB: FOOD00064)
Cucurbita (FooDB: FOOD00066)
Watermelon (FooDB: FOOD00052)
Bitter gourd (FooDB: FOOD00115)
Calabash (FooDB: FOOD00318)
Towel gourd (FooDB: FOOD00492)
Winter squash (FooDB: FOOD00283)
Butternut squash (FooDB: FOOD00317)
Wax gourd (FooDB: FOOD00499)
Green zucchini (FooDB: FOOD00875)
Yellow zucchini (FooDB: FOOD00876)
Japanese pumpkin (FooDB: FOOD00886)
Sunburst squash (pattypan squash) (FooDB: FOOD00874)
Tinda (FooDB: FOOD00559)
Horned melon (FooDB: FOOD00761)

Tea

Herbal tea

Greenthread tea (FooDB: FOOD00820)

Cocoa and cocoa product

Cocoa

Cocoa bean (FooDB: FOOD00182)

Process

Role

Indirect biological role

Metabotoxin

Metabotoxin (HMDB: HMDB0001097)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.0055 g/L	ALOGPS
logP	3.44	ALOGPS
logP	6.2	ChemAxon
logS	-5	ALOGPS
pKa (Strongest Acidic)	4.07	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	137.76 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	169.42 m³·mol⁻¹	ChemAxon
Polarizability	64.52 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	231.936	31661259
DarkChem	[M-H]-	229.467	31661259
AllCCS	[M+H]+	238.262	32859911
AllCCS	[M-H]-	234.789	32859911
DeepCCS	[M+H]+	241.137	30932474
DeepCCS	[M-H]-	238.926	30932474
DeepCCS	[M-2H]-	272.168	30932474
DeepCCS	[M+Na]+	247.05	30932474
AllCCS	[M+H]+	238.3	32859911
AllCCS	[M+H-H2O]+	236.8	32859911
AllCCS	[M+NH4]+	239.6	32859911
AllCCS	[M+Na]+	240.0	32859911
AllCCS	[M-H]-	234.8	32859911
AllCCS	[M+Na-2H]-	236.6	32859911
AllCCS	[M+HCOO]-	238.7	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Protoporphyrinogen IX	CC1=C2CC3=C(C)C(C=C)=C(CC4=C(C)C(C=C)=C(CC5=C(C)C(CCC(O)=O)=C(CC(N2)=C1CCC(O)=O)N5)N4)N3	5796.1	Standard polar	33892256
Protoporphyrinogen IX	CC1=C2CC3=C(C)C(C=C)=C(CC4=C(C)C(C=C)=C(CC5=C(C)C(CCC(O)=O)=C(CC(N2)=C1CCC(O)=O)N5)N4)N3	4191.6	Standard non polar	33892256
Protoporphyrinogen IX	CC1=C2CC3=C(C)C(C=C)=C(CC4=C(C)C(C=C)=C(CC5=C(C)C(CCC(O)=O)=C(CC(N2)=C1CCC(O)=O)N5)N4)N3	5415.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Protoporphyrinogen IX,1TMS,isomer #1	C=CC1=C2CC3=C(C)C(C=C)=C(CC4=C(C)C(CCC(=O)O[Si](C)(C)C)=C(CC5=C(CCC(=O)O)C(C)=C(CC(=C1C)[NH]2)[NH]5)[NH]4)[NH]3	5056.8	Semi standard non polar	33892256
Protoporphyrinogen IX,1TMS,isomer #2	C=CC1=C2CC3=C(C)C(C=C)=C(CC4=C(C)C(CCC(=O)O)=C(CC5=C(CCC(=O)O[Si](C)(C)C)C(C)=C(CC(=C1C)[NH]2)[NH]5)[NH]4)[NH]3	5056.8	Semi standard non polar	33892256
Protoporphyrinogen IX,1TMS,isomer #3	C=CC1=C2CC3=C(C)C(C=C)=C(CC4=C(C)C(CCC(=O)O)=C(CC5=C(CCC(=O)O)C(C)=C(CC(=C1C)[NH]2)N5[Si](C)(C)C)[NH]4)[NH]3	5134.8	Semi standard non polar	33892256
Protoporphyrinogen IX,1TMS,isomer #4	C=CC1=C2CC3=C(C)C(C=C)=C(CC4=C(C)C(CCC(=O)O)=C(CC5=C(CCC(=O)O)C(C)=C(CC(=C1C)[NH]2)[NH]5)N4[Si](C)(C)C)[NH]3	5139.4	Semi standard non polar	33892256
Protoporphyrinogen IX,1TMS,isomer #5	C=CC1=C2CC3=C(C)C(C=C)=C(CC4=C(C)C(CCC(=O)O)=C(CC5=C(CCC(=O)O)C(C)=C(CC(=C1C)[NH]2)[NH]5)[NH]4)N3[Si](C)(C)C	5093.7	Semi standard non polar	33892256
Protoporphyrinogen IX,1TMS,isomer #6	C=CC1=C2CC3=C(C)C(CCC(=O)O)=C(CC4=C(CCC(=O)O)C(C)=C(CC5=C(C)C(C=C)=C(CC(=C1C)[NH]2)N5[Si](C)(C)C)[NH]4)[NH]3	5090.0	Semi standard non polar	33892256
Protoporphyrinogen IX,2TMS,isomer #1	C=CC1=C2CC3=C(C)C(C=C)=C(CC4=C(C)C(CCC(=O)O[Si](C)(C)C)=C(CC5=C(CCC(=O)O[Si](C)(C)C)C(C)=C(CC(=C1C)[NH]2)[NH]5)[NH]4)[NH]3	4955.1	Semi standard non polar	33892256
Protoporphyrinogen IX,2TMS,isomer #10	C=CC1=C2CC3=C(C)C(CCC(=O)O)=C(CC4=C(CCC(=O)O)C(C)=C(CC5=C(C)C(C=C)=C(CC(=C1C)[NH]2)N5[Si](C)(C)C)N4[Si](C)(C)C)[NH]3	5100.1	Semi standard non polar	33892256
Protoporphyrinogen IX,2TMS,isomer #11	C=CC1=C2CC3=C(C)C(C=C)=C(CC4=C(C)C(CCC(=O)O)=C(CC5=C(CCC(=O)O)C(C)=C(CC(=C1C)[NH]2)N5[Si](C)(C)C)N4[Si](C)(C)C)[NH]3	5147.4	Semi standard non polar	33892256
Protoporphyrinogen IX,2TMS,isomer #12	C=CC1=C2CC3=C(C)C(C=C)=C(CC4=C(C)C(CCC(=O)O)=C(CC5=C(CCC(=O)O)C(C)=C(CC(=C1C)[NH]2)N5[Si](C)(C)C)[NH]4)N3[Si](C)(C)C	5094.7	Semi standard non polar	33892256
Protoporphyrinogen IX,2TMS,isomer #13	C=CC1=C2CC3=C(C)C(CCC(=O)O)=C(CC4=C(CCC(=O)O)C(C)=C(CC5=C(C)C(C=C)=C(CC(=C1C)[NH]2)N5[Si](C)(C)C)[NH]4)N3[Si](C)(C)C	5094.9	Semi standard non polar	33892256
Protoporphyrinogen IX,2TMS,isomer #14	C=CC1=C2CC3=C(C)C(C=C)=C(CC4=C(C)C(CCC(=O)O)=C(CC5=C(CCC(=O)O)C(C)=C(CC(=C1C)[NH]2)[NH]5)N4[Si](C)(C)C)N3[Si](C)(C)C	5110.8	Semi standard non polar	33892256
Protoporphyrinogen IX,2TMS,isomer #15	C=CC1=C2CC3=C(C)C(CCC(=O)O)=C(CC4=C(CCC(=O)O)C(C)=C(CC5=C(C)C(C=C)=C(CC(=C1C)N2[Si](C)(C)C)N5[Si](C)(C)C)[NH]4)[NH]3	5072.4	Semi standard non polar	33892256
Protoporphyrinogen IX,2TMS,isomer #2	C=CC1=C2CC3=C(C)C(CCC(=O)O[Si](C)(C)C)=C(CC4=C(CCC(=O)O)C(C)=C(CC5=C(C)C(C=C)=C(CC(=C1C)[NH]2)N5[Si](C)(C)C)[NH]4)[NH]3	4999.7	Semi standard non polar	33892256
Protoporphyrinogen IX,2TMS,isomer #3	C=CC1=C2CC3=C(C)C(C=C)=C(CC4=C(C)C(CCC(=O)O[Si](C)(C)C)=C(CC5=C(CCC(=O)O)C(C)=C(CC(=C1C)[NH]2)N5[Si](C)(C)C)[NH]4)[NH]3	5033.9	Semi standard non polar	33892256
Protoporphyrinogen IX,2TMS,isomer #4	C=CC1=C2CC3=C(C)C(C=C)=C(CC4=C(C)C(CCC(=O)O[Si](C)(C)C)=C(CC5=C(CCC(=O)O)C(C)=C(CC(=C1C)[NH]2)[NH]5)N4[Si](C)(C)C)[NH]3	5037.0	Semi standard non polar	33892256
Protoporphyrinogen IX,2TMS,isomer #5	C=CC1=C2CC3=C(C)C(C=C)=C(CC4=C(C)C(CCC(=O)O[Si](C)(C)C)=C(CC5=C(CCC(=O)O)C(C)=C(CC(=C1C)[NH]2)[NH]5)[NH]4)N3[Si](C)(C)C	5004.3	Semi standard non polar	33892256
Protoporphyrinogen IX,2TMS,isomer #6	C=CC1=C2CC3=C(C)C(CCC(=O)O)=C(CC4=C(CCC(=O)O[Si](C)(C)C)C(C)=C(CC5=C(C)C(C=C)=C(CC(=C1C)[NH]2)N5[Si](C)(C)C)[NH]4)[NH]3	4999.5	Semi standard non polar	33892256
Protoporphyrinogen IX,2TMS,isomer #7	C=CC1=C2CC3=C(C)C(C=C)=C(CC4=C(C)C(CCC(=O)O)=C(CC5=C(CCC(=O)O[Si](C)(C)C)C(C)=C(CC(=C1C)[NH]2)N5[Si](C)(C)C)[NH]4)[NH]3	5031.3	Semi standard non polar	33892256
Protoporphyrinogen IX,2TMS,isomer #8	C=CC1=C2CC3=C(C)C(C=C)=C(CC4=C(C)C(CCC(=O)O)=C(CC5=C(CCC(=O)O[Si](C)(C)C)C(C)=C(CC(=C1C)[NH]2)[NH]5)N4[Si](C)(C)C)[NH]3	5039.6	Semi standard non polar	33892256
Protoporphyrinogen IX,2TMS,isomer #9	C=CC1=C2CC3=C(C)C(C=C)=C(CC4=C(C)C(CCC(=O)O)=C(CC5=C(CCC(=O)O[Si](C)(C)C)C(C)=C(CC(=C1C)[NH]2)[NH]5)[NH]4)N3[Si](C)(C)C	5004.3	Semi standard non polar	33892256
Protoporphyrinogen IX,3TMS,isomer #1	C=CC1=C2CC3=C(C)C(CCC(=O)O[Si](C)(C)C)=C(CC4=C(CCC(=O)O[Si](C)(C)C)C(C)=C(CC5=C(C)C(C=C)=C(CC(=C1C)[NH]2)N5[Si](C)(C)C)[NH]4)[NH]3	4920.5	Semi standard non polar	33892256
Protoporphyrinogen IX,3TMS,isomer #1	C=CC1=C2CC3=C(C)C(CCC(=O)O[Si](C)(C)C)=C(CC4=C(CCC(=O)O[Si](C)(C)C)C(C)=C(CC5=C(C)C(C=C)=C(CC(=C1C)[NH]2)N5[Si](C)(C)C)[NH]4)[NH]3	4535.4	Standard non polar	33892256
Protoporphyrinogen IX,3TMS,isomer #1	C=CC1=C2CC3=C(C)C(CCC(=O)O[Si](C)(C)C)=C(CC4=C(CCC(=O)O[Si](C)(C)C)C(C)=C(CC5=C(C)C(C=C)=C(CC(=C1C)[NH]2)N5[Si](C)(C)C)[NH]4)[NH]3	6148.8	Standard polar	33892256
Protoporphyrinogen IX,3TMS,isomer #10	C=CC1=C2CC3=C(C)C(C=C)=C(CC4=C(C)C(CCC(=O)O[Si](C)(C)C)=C(CC5=C(CCC(=O)O)C(C)=C(CC(=C1C)[NH]2)[NH]5)N4[Si](C)(C)C)N3[Si](C)(C)C	5029.7	Semi standard non polar	33892256
Protoporphyrinogen IX,3TMS,isomer #10	C=CC1=C2CC3=C(C)C(C=C)=C(CC4=C(C)C(CCC(=O)O[Si](C)(C)C)=C(CC5=C(CCC(=O)O)C(C)=C(CC(=C1C)[NH]2)[NH]5)N4[Si](C)(C)C)N3[Si](C)(C)C	4536.9	Standard non polar	33892256
Protoporphyrinogen IX,3TMS,isomer #10	C=CC1=C2CC3=C(C)C(C=C)=C(CC4=C(C)C(CCC(=O)O[Si](C)(C)C)=C(CC5=C(CCC(=O)O)C(C)=C(CC(=C1C)[NH]2)[NH]5)N4[Si](C)(C)C)N3[Si](C)(C)C	6162.2	Standard polar	33892256
Protoporphyrinogen IX,3TMS,isomer #11	C=CC1=C2CC3=C(C)C(CCC(=O)O)=C(CC4=C(CCC(=O)O[Si](C)(C)C)C(C)=C(CC5=C(C)C(C=C)=C(CC(=C1C)N2[Si](C)(C)C)N5[Si](C)(C)C)[NH]4)[NH]3	5000.6	Semi standard non polar	33892256
Protoporphyrinogen IX,3TMS,isomer #11	C=CC1=C2CC3=C(C)C(CCC(=O)O)=C(CC4=C(CCC(=O)O[Si](C)(C)C)C(C)=C(CC5=C(C)C(C=C)=C(CC(=C1C)N2[Si](C)(C)C)N5[Si](C)(C)C)[NH]4)[NH]3	4556.7	Standard non polar	33892256
Protoporphyrinogen IX,3TMS,isomer #11	C=CC1=C2CC3=C(C)C(CCC(=O)O)=C(CC4=C(CCC(=O)O[Si](C)(C)C)C(C)=C(CC5=C(C)C(C=C)=C(CC(=C1C)N2[Si](C)(C)C)N5[Si](C)(C)C)[NH]4)[NH]3	6052.7	Standard polar	33892256
Protoporphyrinogen IX,3TMS,isomer #12	C=CC1=C2CC3=C(C)C(CCC(=O)O)=C(CC4=C(CCC(=O)O[Si](C)(C)C)C(C)=C(CC5=C(C)C(C=C)=C(CC(=C1C)[NH]2)N5[Si](C)(C)C)N4[Si](C)(C)C)[NH]3	5019.1	Semi standard non polar	33892256
Protoporphyrinogen IX,3TMS,isomer #12	C=CC1=C2CC3=C(C)C(CCC(=O)O)=C(CC4=C(CCC(=O)O[Si](C)(C)C)C(C)=C(CC5=C(C)C(C=C)=C(CC(=C1C)[NH]2)N5[Si](C)(C)C)N4[Si](C)(C)C)[NH]3	4535.6	Standard non polar	33892256
Protoporphyrinogen IX,3TMS,isomer #12	C=CC1=C2CC3=C(C)C(CCC(=O)O)=C(CC4=C(CCC(=O)O[Si](C)(C)C)C(C)=C(CC5=C(C)C(C=C)=C(CC(=C1C)[NH]2)N5[Si](C)(C)C)N4[Si](C)(C)C)[NH]3	6160.7	Standard polar	33892256
Protoporphyrinogen IX,3TMS,isomer #13	C=CC1=C2CC3=C(C)C(CCC(=O)O)=C(CC4=C(CCC(=O)O[Si](C)(C)C)C(C)=C(CC5=C(C)C(C=C)=C(CC(=C1C)[NH]2)N5[Si](C)(C)C)[NH]4)N3[Si](C)(C)C	5018.1	Semi standard non polar	33892256
Protoporphyrinogen IX,3TMS,isomer #13	C=CC1=C2CC3=C(C)C(CCC(=O)O)=C(CC4=C(CCC(=O)O[Si](C)(C)C)C(C)=C(CC5=C(C)C(C=C)=C(CC(=C1C)[NH]2)N5[Si](C)(C)C)[NH]4)N3[Si](C)(C)C	4532.2	Standard non polar	33892256
Protoporphyrinogen IX,3TMS,isomer #13	C=CC1=C2CC3=C(C)C(CCC(=O)O)=C(CC4=C(CCC(=O)O[Si](C)(C)C)C(C)=C(CC5=C(C)C(C=C)=C(CC(=C1C)[NH]2)N5[Si](C)(C)C)[NH]4)N3[Si](C)(C)C	6163.5	Standard polar	33892256
Protoporphyrinogen IX,3TMS,isomer #14	C=CC1=C2CC3=C(C)C(C=C)=C(CC4=C(C)C(CCC(=O)O)=C(CC5=C(CCC(=O)O[Si](C)(C)C)C(C)=C(CC(=C1C)[NH]2)N5[Si](C)(C)C)N4[Si](C)(C)C)[NH]3	5057.4	Semi standard non polar	33892256
Protoporphyrinogen IX,3TMS,isomer #14	C=CC1=C2CC3=C(C)C(C=C)=C(CC4=C(C)C(CCC(=O)O)=C(CC5=C(CCC(=O)O[Si](C)(C)C)C(C)=C(CC(=C1C)[NH]2)N5[Si](C)(C)C)N4[Si](C)(C)C)[NH]3	4510.6	Standard non polar	33892256
Protoporphyrinogen IX,3TMS,isomer #14	C=CC1=C2CC3=C(C)C(C=C)=C(CC4=C(C)C(CCC(=O)O)=C(CC5=C(CCC(=O)O[Si](C)(C)C)C(C)=C(CC(=C1C)[NH]2)N5[Si](C)(C)C)N4[Si](C)(C)C)[NH]3	6265.9	Standard polar	33892256
Protoporphyrinogen IX,3TMS,isomer #15	C=CC1=C2CC3=C(C)C(C=C)=C(CC4=C(C)C(CCC(=O)O)=C(CC5=C(CCC(=O)O[Si](C)(C)C)C(C)=C(CC(=C1C)[NH]2)N5[Si](C)(C)C)[NH]4)N3[Si](C)(C)C	5015.1	Semi standard non polar	33892256
Protoporphyrinogen IX,3TMS,isomer #15	C=CC1=C2CC3=C(C)C(C=C)=C(CC4=C(C)C(CCC(=O)O)=C(CC5=C(CCC(=O)O[Si](C)(C)C)C(C)=C(CC(=C1C)[NH]2)N5[Si](C)(C)C)[NH]4)N3[Si](C)(C)C	4533.5	Standard non polar	33892256
Protoporphyrinogen IX,3TMS,isomer #15	C=CC1=C2CC3=C(C)C(C=C)=C(CC4=C(C)C(CCC(=O)O)=C(CC5=C(CCC(=O)O[Si](C)(C)C)C(C)=C(CC(=C1C)[NH]2)N5[Si](C)(C)C)[NH]4)N3[Si](C)(C)C	6159.4	Standard polar	33892256
Protoporphyrinogen IX,3TMS,isomer #16	C=CC1=C2CC3=C(C)C(C=C)=C(CC4=C(C)C(CCC(=O)O)=C(CC5=C(CCC(=O)O[Si](C)(C)C)C(C)=C(CC(=C1C)[NH]2)[NH]5)N4[Si](C)(C)C)N3[Si](C)(C)C	5033.0	Semi standard non polar	33892256
Protoporphyrinogen IX,3TMS,isomer #16	C=CC1=C2CC3=C(C)C(C=C)=C(CC4=C(C)C(CCC(=O)O)=C(CC5=C(CCC(=O)O[Si](C)(C)C)C(C)=C(CC(=C1C)[NH]2)[NH]5)N4[Si](C)(C)C)N3[Si](C)(C)C	4535.3	Standard non polar	33892256
Protoporphyrinogen IX,3TMS,isomer #16	C=CC1=C2CC3=C(C)C(C=C)=C(CC4=C(C)C(CCC(=O)O)=C(CC5=C(CCC(=O)O[Si](C)(C)C)C(C)=C(CC(=C1C)[NH]2)[NH]5)N4[Si](C)(C)C)N3[Si](C)(C)C	6166.3	Standard polar	33892256
Protoporphyrinogen IX,3TMS,isomer #17	C=CC1=C2CC3=C(C)C(CCC(=O)O)=C(CC4=C(CCC(=O)O)C(C)=C(CC5=C(C)C(C=C)=C(CC(=C1C)N2[Si](C)(C)C)N5[Si](C)(C)C)N4[Si](C)(C)C)[NH]3	5100.4	Semi standard non polar	33892256
Protoporphyrinogen IX,3TMS,isomer #17	C=CC1=C2CC3=C(C)C(CCC(=O)O)=C(CC4=C(CCC(=O)O)C(C)=C(CC5=C(C)C(C=C)=C(CC(=C1C)N2[Si](C)(C)C)N5[Si](C)(C)C)N4[Si](C)(C)C)[NH]3	4570.4	Standard non polar	33892256
Protoporphyrinogen IX,3TMS,isomer #17	C=CC1=C2CC3=C(C)C(CCC(=O)O)=C(CC4=C(CCC(=O)O)C(C)=C(CC5=C(C)C(C=C)=C(CC(=C1C)N2[Si](C)(C)C)N5[Si](C)(C)C)N4[Si](C)(C)C)[NH]3	6070.2	Standard polar	33892256
Protoporphyrinogen IX,3TMS,isomer #18	C=CC1=C2CC3=C(C)C(CCC(=O)O)=C(CC4=C(CCC(=O)O)C(C)=C(CC5=C(C)C(C=C)=C(CC(=C1C)[NH]2)N5[Si](C)(C)C)N4[Si](C)(C)C)N3[Si](C)(C)C	5144.4	Semi standard non polar	33892256
Protoporphyrinogen IX,3TMS,isomer #18	C=CC1=C2CC3=C(C)C(CCC(=O)O)=C(CC4=C(CCC(=O)O)C(C)=C(CC5=C(C)C(C=C)=C(CC(=C1C)[NH]2)N5[Si](C)(C)C)N4[Si](C)(C)C)N3[Si](C)(C)C	4548.5	Standard non polar	33892256
Protoporphyrinogen IX,3TMS,isomer #18	C=CC1=C2CC3=C(C)C(CCC(=O)O)=C(CC4=C(CCC(=O)O)C(C)=C(CC5=C(C)C(C=C)=C(CC(=C1C)[NH]2)N5[Si](C)(C)C)N4[Si](C)(C)C)N3[Si](C)(C)C	6190.1	Standard polar	33892256
Protoporphyrinogen IX,3TMS,isomer #19	C=CC1=C2CC3=C(C)C(C=C)=C(CC4=C(C)C(CCC(=O)O)=C(CC5=C(CCC(=O)O)C(C)=C(CC(=C1C)[NH]2)N5[Si](C)(C)C)N4[Si](C)(C)C)N3[Si](C)(C)C	5149.1	Semi standard non polar	33892256
Protoporphyrinogen IX,3TMS,isomer #19	C=CC1=C2CC3=C(C)C(C=C)=C(CC4=C(C)C(CCC(=O)O)=C(CC5=C(CCC(=O)O)C(C)=C(CC(=C1C)[NH]2)N5[Si](C)(C)C)N4[Si](C)(C)C)N3[Si](C)(C)C	4548.6	Standard non polar	33892256
Protoporphyrinogen IX,3TMS,isomer #19	C=CC1=C2CC3=C(C)C(C=C)=C(CC4=C(C)C(CCC(=O)O)=C(CC5=C(CCC(=O)O)C(C)=C(CC(=C1C)[NH]2)N5[Si](C)(C)C)N4[Si](C)(C)C)N3[Si](C)(C)C	6190.9	Standard polar	33892256
Protoporphyrinogen IX,3TMS,isomer #2	C=CC1=C2CC3=C(C)C(C=C)=C(CC4=C(C)C(CCC(=O)O[Si](C)(C)C)=C(CC5=C(CCC(=O)O[Si](C)(C)C)C(C)=C(CC(=C1C)[NH]2)N5[Si](C)(C)C)[NH]4)[NH]3	4930.7	Semi standard non polar	33892256
Protoporphyrinogen IX,3TMS,isomer #2	C=CC1=C2CC3=C(C)C(C=C)=C(CC4=C(C)C(CCC(=O)O[Si](C)(C)C)=C(CC5=C(CCC(=O)O[Si](C)(C)C)C(C)=C(CC(=C1C)[NH]2)N5[Si](C)(C)C)[NH]4)[NH]3	4511.7	Standard non polar	33892256
Protoporphyrinogen IX,3TMS,isomer #2	C=CC1=C2CC3=C(C)C(C=C)=C(CC4=C(C)C(CCC(=O)O[Si](C)(C)C)=C(CC5=C(CCC(=O)O[Si](C)(C)C)C(C)=C(CC(=C1C)[NH]2)N5[Si](C)(C)C)[NH]4)[NH]3	6244.6	Standard polar	33892256
Protoporphyrinogen IX,3TMS,isomer #20	C=CC1=C2CC3=C(C)C(C=C)=C(CC4=C(C)C(CCC(=O)O)=C(CC5=C(CCC(=O)O)C(C)=C(CC(=C1C)N2[Si](C)(C)C)[NH]5)N4[Si](C)(C)C)N3[Si](C)(C)C	5104.9	Semi standard non polar	33892256
Protoporphyrinogen IX,3TMS,isomer #20	C=CC1=C2CC3=C(C)C(C=C)=C(CC4=C(C)C(CCC(=O)O)=C(CC5=C(CCC(=O)O)C(C)=C(CC(=C1C)N2[Si](C)(C)C)[NH]5)N4[Si](C)(C)C)N3[Si](C)(C)C	4570.2	Standard non polar	33892256
Protoporphyrinogen IX,3TMS,isomer #20	C=CC1=C2CC3=C(C)C(C=C)=C(CC4=C(C)C(CCC(=O)O)=C(CC5=C(CCC(=O)O)C(C)=C(CC(=C1C)N2[Si](C)(C)C)[NH]5)N4[Si](C)(C)C)N3[Si](C)(C)C	6070.9	Standard polar	33892256
Protoporphyrinogen IX,3TMS,isomer #3	C=CC1=C2CC3=C(C)C(C=C)=C(CC4=C(C)C(CCC(=O)O[Si](C)(C)C)=C(CC5=C(CCC(=O)O[Si](C)(C)C)C(C)=C(CC(=C1C)[NH]2)[NH]5)N4[Si](C)(C)C)[NH]3	4934.8	Semi standard non polar	33892256
Protoporphyrinogen IX,3TMS,isomer #3	C=CC1=C2CC3=C(C)C(C=C)=C(CC4=C(C)C(CCC(=O)O[Si](C)(C)C)=C(CC5=C(CCC(=O)O[Si](C)(C)C)C(C)=C(CC(=C1C)[NH]2)[NH]5)N4[Si](C)(C)C)[NH]3	4513.6	Standard non polar	33892256
Protoporphyrinogen IX,3TMS,isomer #3	C=CC1=C2CC3=C(C)C(C=C)=C(CC4=C(C)C(CCC(=O)O[Si](C)(C)C)=C(CC5=C(CCC(=O)O[Si](C)(C)C)C(C)=C(CC(=C1C)[NH]2)[NH]5)N4[Si](C)(C)C)[NH]3	6245.1	Standard polar	33892256
Protoporphyrinogen IX,3TMS,isomer #4	C=CC1=C2CC3=C(C)C(C=C)=C(CC4=C(C)C(CCC(=O)O[Si](C)(C)C)=C(CC5=C(CCC(=O)O[Si](C)(C)C)C(C)=C(CC(=C1C)[NH]2)[NH]5)[NH]4)N3[Si](C)(C)C	4923.5	Semi standard non polar	33892256
Protoporphyrinogen IX,3TMS,isomer #4	C=CC1=C2CC3=C(C)C(C=C)=C(CC4=C(C)C(CCC(=O)O[Si](C)(C)C)=C(CC5=C(CCC(=O)O[Si](C)(C)C)C(C)=C(CC(=C1C)[NH]2)[NH]5)[NH]4)N3[Si](C)(C)C	4538.1	Standard non polar	33892256
Protoporphyrinogen IX,3TMS,isomer #4	C=CC1=C2CC3=C(C)C(C=C)=C(CC4=C(C)C(CCC(=O)O[Si](C)(C)C)=C(CC5=C(CCC(=O)O[Si](C)(C)C)C(C)=C(CC(=C1C)[NH]2)[NH]5)[NH]4)N3[Si](C)(C)C	6149.2	Standard polar	33892256
Protoporphyrinogen IX,3TMS,isomer #5	C=CC1=C2CC3=C(C)C(CCC(=O)O[Si](C)(C)C)=C(CC4=C(CCC(=O)O)C(C)=C(CC5=C(C)C(C=C)=C(CC(=C1C)N2[Si](C)(C)C)N5[Si](C)(C)C)[NH]4)[NH]3	5000.6	Semi standard non polar	33892256
Protoporphyrinogen IX,3TMS,isomer #5	C=CC1=C2CC3=C(C)C(CCC(=O)O[Si](C)(C)C)=C(CC4=C(CCC(=O)O)C(C)=C(CC5=C(C)C(C=C)=C(CC(=C1C)N2[Si](C)(C)C)N5[Si](C)(C)C)[NH]4)[NH]3	4556.7	Standard non polar	33892256
Protoporphyrinogen IX,3TMS,isomer #5	C=CC1=C2CC3=C(C)C(CCC(=O)O[Si](C)(C)C)=C(CC4=C(CCC(=O)O)C(C)=C(CC5=C(C)C(C=C)=C(CC(=C1C)N2[Si](C)(C)C)N5[Si](C)(C)C)[NH]4)[NH]3	6052.7	Standard polar	33892256
Protoporphyrinogen IX,3TMS,isomer #6	C=CC1=C2CC3=C(C)C(CCC(=O)O[Si](C)(C)C)=C(CC4=C(CCC(=O)O)C(C)=C(CC5=C(C)C(C=C)=C(CC(=C1C)[NH]2)N5[Si](C)(C)C)N4[Si](C)(C)C)[NH]3	5021.7	Semi standard non polar	33892256
Protoporphyrinogen IX,3TMS,isomer #6	C=CC1=C2CC3=C(C)C(CCC(=O)O[Si](C)(C)C)=C(CC4=C(CCC(=O)O)C(C)=C(CC5=C(C)C(C=C)=C(CC(=C1C)[NH]2)N5[Si](C)(C)C)N4[Si](C)(C)C)[NH]3	4533.7	Standard non polar	33892256
Protoporphyrinogen IX,3TMS,isomer #6	C=CC1=C2CC3=C(C)C(CCC(=O)O[Si](C)(C)C)=C(CC4=C(CCC(=O)O)C(C)=C(CC5=C(C)C(C=C)=C(CC(=C1C)[NH]2)N5[Si](C)(C)C)N4[Si](C)(C)C)[NH]3	6164.9	Standard polar	33892256
Protoporphyrinogen IX,3TMS,isomer #7	C=CC1=C2CC3=C(C)C(CCC(=O)O[Si](C)(C)C)=C(CC4=C(CCC(=O)O)C(C)=C(CC5=C(C)C(C=C)=C(CC(=C1C)[NH]2)N5[Si](C)(C)C)[NH]4)N3[Si](C)(C)C	5014.8	Semi standard non polar	33892256
Protoporphyrinogen IX,3TMS,isomer #7	C=CC1=C2CC3=C(C)C(CCC(=O)O[Si](C)(C)C)=C(CC4=C(CCC(=O)O)C(C)=C(CC5=C(C)C(C=C)=C(CC(=C1C)[NH]2)N5[Si](C)(C)C)[NH]4)N3[Si](C)(C)C	4534.0	Standard non polar	33892256
Protoporphyrinogen IX,3TMS,isomer #7	C=CC1=C2CC3=C(C)C(CCC(=O)O[Si](C)(C)C)=C(CC4=C(CCC(=O)O)C(C)=C(CC5=C(C)C(C=C)=C(CC(=C1C)[NH]2)N5[Si](C)(C)C)[NH]4)N3[Si](C)(C)C	6159.4	Standard polar	33892256
Protoporphyrinogen IX,3TMS,isomer #8	C=CC1=C2CC3=C(C)C(C=C)=C(CC4=C(C)C(CCC(=O)O[Si](C)(C)C)=C(CC5=C(CCC(=O)O)C(C)=C(CC(=C1C)[NH]2)N5[Si](C)(C)C)N4[Si](C)(C)C)[NH]3	5057.4	Semi standard non polar	33892256
Protoporphyrinogen IX,3TMS,isomer #8	C=CC1=C2CC3=C(C)C(C=C)=C(CC4=C(C)C(CCC(=O)O[Si](C)(C)C)=C(CC5=C(CCC(=O)O)C(C)=C(CC(=C1C)[NH]2)N5[Si](C)(C)C)N4[Si](C)(C)C)[NH]3	4510.5	Standard non polar	33892256
Protoporphyrinogen IX,3TMS,isomer #8	C=CC1=C2CC3=C(C)C(C=C)=C(CC4=C(C)C(CCC(=O)O[Si](C)(C)C)=C(CC5=C(CCC(=O)O)C(C)=C(CC(=C1C)[NH]2)N5[Si](C)(C)C)N4[Si](C)(C)C)[NH]3	6266.0	Standard polar	33892256
Protoporphyrinogen IX,3TMS,isomer #9	C=CC1=C2CC3=C(C)C(C=C)=C(CC4=C(C)C(CCC(=O)O[Si](C)(C)C)=C(CC5=C(CCC(=O)O)C(C)=C(CC(=C1C)[NH]2)N5[Si](C)(C)C)[NH]4)N3[Si](C)(C)C	5018.2	Semi standard non polar	33892256
Protoporphyrinogen IX,3TMS,isomer #9	C=CC1=C2CC3=C(C)C(C=C)=C(CC4=C(C)C(CCC(=O)O[Si](C)(C)C)=C(CC5=C(CCC(=O)O)C(C)=C(CC(=C1C)[NH]2)N5[Si](C)(C)C)[NH]4)N3[Si](C)(C)C	4531.6	Standard non polar	33892256
Protoporphyrinogen IX,3TMS,isomer #9	C=CC1=C2CC3=C(C)C(C=C)=C(CC4=C(C)C(CCC(=O)O[Si](C)(C)C)=C(CC5=C(CCC(=O)O)C(C)=C(CC(=C1C)[NH]2)N5[Si](C)(C)C)[NH]4)N3[Si](C)(C)C	6163.5	Standard polar	33892256
Protoporphyrinogen IX,4TMS,isomer #1	C=CC1=C2CC3=C(C)C(CCC(=O)O[Si](C)(C)C)=C(CC4=C(CCC(=O)O[Si](C)(C)C)C(C)=C(CC5=C(C)C(C=C)=C(CC(=C1C)N2[Si](C)(C)C)N5[Si](C)(C)C)[NH]4)[NH]3	4905.1	Semi standard non polar	33892256
Protoporphyrinogen IX,4TMS,isomer #1	C=CC1=C2CC3=C(C)C(CCC(=O)O[Si](C)(C)C)=C(CC4=C(CCC(=O)O[Si](C)(C)C)C(C)=C(CC5=C(C)C(C=C)=C(CC(=C1C)N2[Si](C)(C)C)N5[Si](C)(C)C)[NH]4)[NH]3	4512.9	Standard non polar	33892256
Protoporphyrinogen IX,4TMS,isomer #1	C=CC1=C2CC3=C(C)C(CCC(=O)O[Si](C)(C)C)=C(CC4=C(CCC(=O)O[Si](C)(C)C)C(C)=C(CC5=C(C)C(C=C)=C(CC(=C1C)N2[Si](C)(C)C)N5[Si](C)(C)C)[NH]4)[NH]3	5792.4	Standard polar	33892256
Protoporphyrinogen IX,4TMS,isomer #10	C=CC1=C2CC3=C(C)C(C=C)=C(CC4=C(C)C(CCC(=O)O[Si](C)(C)C)=C(CC5=C(CCC(=O)O)C(C)=C(CC(=C1C)[NH]2)N5[Si](C)(C)C)N4[Si](C)(C)C)N3[Si](C)(C)C	5060.9	Semi standard non polar	33892256
Protoporphyrinogen IX,4TMS,isomer #10	C=CC1=C2CC3=C(C)C(C=C)=C(CC4=C(C)C(CCC(=O)O[Si](C)(C)C)=C(CC5=C(CCC(=O)O)C(C)=C(CC(=C1C)[NH]2)N5[Si](C)(C)C)N4[Si](C)(C)C)N3[Si](C)(C)C	4484.4	Standard non polar	33892256
Protoporphyrinogen IX,4TMS,isomer #10	C=CC1=C2CC3=C(C)C(C=C)=C(CC4=C(C)C(CCC(=O)O[Si](C)(C)C)=C(CC5=C(CCC(=O)O)C(C)=C(CC(=C1C)[NH]2)N5[Si](C)(C)C)N4[Si](C)(C)C)N3[Si](C)(C)C	5934.4	Standard polar	33892256
Protoporphyrinogen IX,4TMS,isomer #11	C=CC1=C2CC3=C(C)C(C=C)=C(CC4=C(C)C(CCC(=O)O)=C(CC5=C(CCC(=O)O[Si](C)(C)C)C(C)=C(CC(=C1C)N2[Si](C)(C)C)[NH]5)N4[Si](C)(C)C)N3[Si](C)(C)C	5018.7	Semi standard non polar	33892256
Protoporphyrinogen IX,4TMS,isomer #11	C=CC1=C2CC3=C(C)C(C=C)=C(CC4=C(C)C(CCC(=O)O)=C(CC5=C(CCC(=O)O[Si](C)(C)C)C(C)=C(CC(=C1C)N2[Si](C)(C)C)[NH]5)N4[Si](C)(C)C)N3[Si](C)(C)C	4505.6	Standard non polar	33892256
Protoporphyrinogen IX,4TMS,isomer #11	C=CC1=C2CC3=C(C)C(C=C)=C(CC4=C(C)C(CCC(=O)O)=C(CC5=C(CCC(=O)O[Si](C)(C)C)C(C)=C(CC(=C1C)N2[Si](C)(C)C)[NH]5)N4[Si](C)(C)C)N3[Si](C)(C)C	5810.7	Standard polar	33892256
Protoporphyrinogen IX,4TMS,isomer #12	C=CC1=C2CC3=C(C)C(CCC(=O)O)=C(CC4=C(CCC(=O)O[Si](C)(C)C)C(C)=C(CC5=C(C)C(C=C)=C(CC(=C1C)N2[Si](C)(C)C)N5[Si](C)(C)C)N4[Si](C)(C)C)[NH]3	5013.4	Semi standard non polar	33892256
Protoporphyrinogen IX,4TMS,isomer #12	C=CC1=C2CC3=C(C)C(CCC(=O)O)=C(CC4=C(CCC(=O)O[Si](C)(C)C)C(C)=C(CC5=C(C)C(C=C)=C(CC(=C1C)N2[Si](C)(C)C)N5[Si](C)(C)C)N4[Si](C)(C)C)[NH]3	4508.3	Standard non polar	33892256
Protoporphyrinogen IX,4TMS,isomer #12	C=CC1=C2CC3=C(C)C(CCC(=O)O)=C(CC4=C(CCC(=O)O[Si](C)(C)C)C(C)=C(CC5=C(C)C(C=C)=C(CC(=C1C)N2[Si](C)(C)C)N5[Si](C)(C)C)N4[Si](C)(C)C)[NH]3	5806.2	Standard polar	33892256
Protoporphyrinogen IX,4TMS,isomer #13	C=CC1=C2CC3=C(C)C(CCC(=O)O)=C(CC4=C(CCC(=O)O[Si](C)(C)C)C(C)=C(CC5=C(C)C(C=C)=C(CC(=C1C)[NH]2)N5[Si](C)(C)C)N4[Si](C)(C)C)N3[Si](C)(C)C	5057.3	Semi standard non polar	33892256
Protoporphyrinogen IX,4TMS,isomer #13	C=CC1=C2CC3=C(C)C(CCC(=O)O)=C(CC4=C(CCC(=O)O[Si](C)(C)C)C(C)=C(CC5=C(C)C(C=C)=C(CC(=C1C)[NH]2)N5[Si](C)(C)C)N4[Si](C)(C)C)N3[Si](C)(C)C	4486.4	Standard non polar	33892256
Protoporphyrinogen IX,4TMS,isomer #13	C=CC1=C2CC3=C(C)C(CCC(=O)O)=C(CC4=C(CCC(=O)O[Si](C)(C)C)C(C)=C(CC5=C(C)C(C=C)=C(CC(=C1C)[NH]2)N5[Si](C)(C)C)N4[Si](C)(C)C)N3[Si](C)(C)C	5934.7	Standard polar	33892256
Protoporphyrinogen IX,4TMS,isomer #14	C=CC1=C2CC3=C(C)C(C=C)=C(CC4=C(C)C(CCC(=O)O)=C(CC5=C(CCC(=O)O[Si](C)(C)C)C(C)=C(CC(=C1C)[NH]2)N5[Si](C)(C)C)N4[Si](C)(C)C)N3[Si](C)(C)C	5060.9	Semi standard non polar	33892256
Protoporphyrinogen IX,4TMS,isomer #14	C=CC1=C2CC3=C(C)C(C=C)=C(CC4=C(C)C(CCC(=O)O)=C(CC5=C(CCC(=O)O[Si](C)(C)C)C(C)=C(CC(=C1C)[NH]2)N5[Si](C)(C)C)N4[Si](C)(C)C)N3[Si](C)(C)C	4484.5	Standard non polar	33892256
Protoporphyrinogen IX,4TMS,isomer #14	C=CC1=C2CC3=C(C)C(C=C)=C(CC4=C(C)C(CCC(=O)O)=C(CC5=C(CCC(=O)O[Si](C)(C)C)C(C)=C(CC(=C1C)[NH]2)N5[Si](C)(C)C)N4[Si](C)(C)C)N3[Si](C)(C)C	5934.4	Standard polar	33892256
Protoporphyrinogen IX,4TMS,isomer #15	C=CC1=C2CC3=C(C)C(C=C)=C(CC4=C(C)C(CCC(=O)O)=C(CC5=C(CCC(=O)O)C(C)=C(CC(=C1C)N2[Si](C)(C)C)N5[Si](C)(C)C)N4[Si](C)(C)C)N3[Si](C)(C)C	5168.3	Semi standard non polar	33892256
Protoporphyrinogen IX,4TMS,isomer #15	C=CC1=C2CC3=C(C)C(C=C)=C(CC4=C(C)C(CCC(=O)O)=C(CC5=C(CCC(=O)O)C(C)=C(CC(=C1C)N2[Si](C)(C)C)N5[Si](C)(C)C)N4[Si](C)(C)C)N3[Si](C)(C)C	4528.9	Standard non polar	33892256
Protoporphyrinogen IX,4TMS,isomer #15	C=CC1=C2CC3=C(C)C(C=C)=C(CC4=C(C)C(CCC(=O)O)=C(CC5=C(CCC(=O)O)C(C)=C(CC(=C1C)N2[Si](C)(C)C)N5[Si](C)(C)C)N4[Si](C)(C)C)N3[Si](C)(C)C	5849.5	Standard polar	33892256
Protoporphyrinogen IX,4TMS,isomer #2	C=CC1=C2CC3=C(C)C(CCC(=O)O[Si](C)(C)C)=C(CC4=C(CCC(=O)O[Si](C)(C)C)C(C)=C(CC5=C(C)C(C=C)=C(CC(=C1C)[NH]2)N5[Si](C)(C)C)N4[Si](C)(C)C)[NH]3	4920.3	Semi standard non polar	33892256
Protoporphyrinogen IX,4TMS,isomer #2	C=CC1=C2CC3=C(C)C(CCC(=O)O[Si](C)(C)C)=C(CC4=C(CCC(=O)O[Si](C)(C)C)C(C)=C(CC5=C(C)C(C=C)=C(CC(=C1C)[NH]2)N5[Si](C)(C)C)N4[Si](C)(C)C)[NH]3	4485.2	Standard non polar	33892256
Protoporphyrinogen IX,4TMS,isomer #2	C=CC1=C2CC3=C(C)C(CCC(=O)O[Si](C)(C)C)=C(CC4=C(CCC(=O)O[Si](C)(C)C)C(C)=C(CC5=C(C)C(C=C)=C(CC(=C1C)[NH]2)N5[Si](C)(C)C)N4[Si](C)(C)C)[NH]3	5908.4	Standard polar	33892256
Protoporphyrinogen IX,4TMS,isomer #3	C=CC1=C2CC3=C(C)C(CCC(=O)O[Si](C)(C)C)=C(CC4=C(CCC(=O)O[Si](C)(C)C)C(C)=C(CC5=C(C)C(C=C)=C(CC(=C1C)[NH]2)N5[Si](C)(C)C)[NH]4)N3[Si](C)(C)C	4918.5	Semi standard non polar	33892256
Protoporphyrinogen IX,4TMS,isomer #3	C=CC1=C2CC3=C(C)C(CCC(=O)O[Si](C)(C)C)=C(CC4=C(CCC(=O)O[Si](C)(C)C)C(C)=C(CC5=C(C)C(C=C)=C(CC(=C1C)[NH]2)N5[Si](C)(C)C)[NH]4)N3[Si](C)(C)C	4482.7	Standard non polar	33892256
Protoporphyrinogen IX,4TMS,isomer #3	C=CC1=C2CC3=C(C)C(CCC(=O)O[Si](C)(C)C)=C(CC4=C(CCC(=O)O[Si](C)(C)C)C(C)=C(CC5=C(C)C(C=C)=C(CC(=C1C)[NH]2)N5[Si](C)(C)C)[NH]4)N3[Si](C)(C)C	5906.1	Standard polar	33892256
Protoporphyrinogen IX,4TMS,isomer #4	C=CC1=C2CC3=C(C)C(C=C)=C(CC4=C(C)C(CCC(=O)O[Si](C)(C)C)=C(CC5=C(CCC(=O)O[Si](C)(C)C)C(C)=C(CC(=C1C)[NH]2)N5[Si](C)(C)C)N4[Si](C)(C)C)[NH]3	4948.8	Semi standard non polar	33892256
Protoporphyrinogen IX,4TMS,isomer #4	C=CC1=C2CC3=C(C)C(C=C)=C(CC4=C(C)C(CCC(=O)O[Si](C)(C)C)=C(CC5=C(CCC(=O)O[Si](C)(C)C)C(C)=C(CC(=C1C)[NH]2)N5[Si](C)(C)C)N4[Si](C)(C)C)[NH]3	4458.9	Standard non polar	33892256
Protoporphyrinogen IX,4TMS,isomer #4	C=CC1=C2CC3=C(C)C(C=C)=C(CC4=C(C)C(CCC(=O)O[Si](C)(C)C)=C(CC5=C(CCC(=O)O[Si](C)(C)C)C(C)=C(CC(=C1C)[NH]2)N5[Si](C)(C)C)N4[Si](C)(C)C)[NH]3	6016.7	Standard polar	33892256
Protoporphyrinogen IX,4TMS,isomer #5	C=CC1=C2CC3=C(C)C(C=C)=C(CC4=C(C)C(CCC(=O)O[Si](C)(C)C)=C(CC5=C(CCC(=O)O[Si](C)(C)C)C(C)=C(CC(=C1C)[NH]2)N5[Si](C)(C)C)[NH]4)N3[Si](C)(C)C	4919.0	Semi standard non polar	33892256
Protoporphyrinogen IX,4TMS,isomer #5	C=CC1=C2CC3=C(C)C(C=C)=C(CC4=C(C)C(CCC(=O)O[Si](C)(C)C)=C(CC5=C(CCC(=O)O[Si](C)(C)C)C(C)=C(CC(=C1C)[NH]2)N5[Si](C)(C)C)[NH]4)N3[Si](C)(C)C	4483.3	Standard non polar	33892256
Protoporphyrinogen IX,4TMS,isomer #5	C=CC1=C2CC3=C(C)C(C=C)=C(CC4=C(C)C(CCC(=O)O[Si](C)(C)C)=C(CC5=C(CCC(=O)O[Si](C)(C)C)C(C)=C(CC(=C1C)[NH]2)N5[Si](C)(C)C)[NH]4)N3[Si](C)(C)C	5905.6	Standard polar	33892256
Protoporphyrinogen IX,4TMS,isomer #6	C=CC1=C2CC3=C(C)C(C=C)=C(CC4=C(C)C(CCC(=O)O[Si](C)(C)C)=C(CC5=C(CCC(=O)O[Si](C)(C)C)C(C)=C(CC(=C1C)[NH]2)[NH]5)N4[Si](C)(C)C)N3[Si](C)(C)C	4928.4	Semi standard non polar	33892256
Protoporphyrinogen IX,4TMS,isomer #6	C=CC1=C2CC3=C(C)C(C=C)=C(CC4=C(C)C(CCC(=O)O[Si](C)(C)C)=C(CC5=C(CCC(=O)O[Si](C)(C)C)C(C)=C(CC(=C1C)[NH]2)[NH]5)N4[Si](C)(C)C)N3[Si](C)(C)C	4486.6	Standard non polar	33892256
Protoporphyrinogen IX,4TMS,isomer #6	C=CC1=C2CC3=C(C)C(C=C)=C(CC4=C(C)C(CCC(=O)O[Si](C)(C)C)=C(CC5=C(CCC(=O)O[Si](C)(C)C)C(C)=C(CC(=C1C)[NH]2)[NH]5)N4[Si](C)(C)C)N3[Si](C)(C)C	5907.7	Standard polar	33892256
Protoporphyrinogen IX,4TMS,isomer #7	C=CC1=C2CC3=C(C)C(C=C)=C(CC4=C(C)C(CCC(=O)O[Si](C)(C)C)=C(CC5=C(CCC(=O)O)C(C)=C(CC(=C1C)N2[Si](C)(C)C)[NH]5)N4[Si](C)(C)C)N3[Si](C)(C)C	5017.2	Semi standard non polar	33892256
Protoporphyrinogen IX,4TMS,isomer #7	C=CC1=C2CC3=C(C)C(C=C)=C(CC4=C(C)C(CCC(=O)O[Si](C)(C)C)=C(CC5=C(CCC(=O)O)C(C)=C(CC(=C1C)N2[Si](C)(C)C)[NH]5)N4[Si](C)(C)C)N3[Si](C)(C)C	4505.7	Standard non polar	33892256
Protoporphyrinogen IX,4TMS,isomer #7	C=CC1=C2CC3=C(C)C(C=C)=C(CC4=C(C)C(CCC(=O)O[Si](C)(C)C)=C(CC5=C(CCC(=O)O)C(C)=C(CC(=C1C)N2[Si](C)(C)C)[NH]5)N4[Si](C)(C)C)N3[Si](C)(C)C	5806.2	Standard polar	33892256
Protoporphyrinogen IX,4TMS,isomer #8	C=CC1=C2CC3=C(C)C(CCC(=O)O[Si](C)(C)C)=C(CC4=C(CCC(=O)O)C(C)=C(CC5=C(C)C(C=C)=C(CC(=C1C)N2[Si](C)(C)C)N5[Si](C)(C)C)N4[Si](C)(C)C)[NH]3	5014.5	Semi standard non polar	33892256
Protoporphyrinogen IX,4TMS,isomer #8	C=CC1=C2CC3=C(C)C(CCC(=O)O[Si](C)(C)C)=C(CC4=C(CCC(=O)O)C(C)=C(CC5=C(C)C(C=C)=C(CC(=C1C)N2[Si](C)(C)C)N5[Si](C)(C)C)N4[Si](C)(C)C)[NH]3	4508.1	Standard non polar	33892256
Protoporphyrinogen IX,4TMS,isomer #8	C=CC1=C2CC3=C(C)C(CCC(=O)O[Si](C)(C)C)=C(CC4=C(CCC(=O)O)C(C)=C(CC5=C(C)C(C=C)=C(CC(=C1C)N2[Si](C)(C)C)N5[Si](C)(C)C)N4[Si](C)(C)C)[NH]3	5810.7	Standard polar	33892256
Protoporphyrinogen IX,4TMS,isomer #9	C=CC1=C2CC3=C(C)C(CCC(=O)O[Si](C)(C)C)=C(CC4=C(CCC(=O)O)C(C)=C(CC5=C(C)C(C=C)=C(CC(=C1C)[NH]2)N5[Si](C)(C)C)N4[Si](C)(C)C)N3[Si](C)(C)C	5057.1	Semi standard non polar	33892256
Protoporphyrinogen IX,4TMS,isomer #9	C=CC1=C2CC3=C(C)C(CCC(=O)O[Si](C)(C)C)=C(CC4=C(CCC(=O)O)C(C)=C(CC5=C(C)C(C=C)=C(CC(=C1C)[NH]2)N5[Si](C)(C)C)N4[Si](C)(C)C)N3[Si](C)(C)C	4486.3	Standard non polar	33892256
Protoporphyrinogen IX,4TMS,isomer #9	C=CC1=C2CC3=C(C)C(CCC(=O)O[Si](C)(C)C)=C(CC4=C(CCC(=O)O)C(C)=C(CC5=C(C)C(C=C)=C(CC(=C1C)[NH]2)N5[Si](C)(C)C)N4[Si](C)(C)C)N3[Si](C)(C)C	5934.7	Standard polar	33892256
Protoporphyrinogen IX,1TBDMS,isomer #1	C=CC1=C2CC3=C(C)C(C=C)=C(CC4=C(C)C(CCC(=O)O[Si](C)(C)C(C)(C)C)=C(CC5=C(CCC(=O)O)C(C)=C(CC(=C1C)[NH]2)[NH]5)[NH]4)[NH]3	5292.7	Semi standard non polar	33892256
Protoporphyrinogen IX,1TBDMS,isomer #2	C=CC1=C2CC3=C(C)C(C=C)=C(CC4=C(C)C(CCC(=O)O)=C(CC5=C(CCC(=O)O[Si](C)(C)C(C)(C)C)C(C)=C(CC(=C1C)[NH]2)[NH]5)[NH]4)[NH]3	5292.8	Semi standard non polar	33892256
Protoporphyrinogen IX,1TBDMS,isomer #3	C=CC1=C2CC3=C(C)C(C=C)=C(CC4=C(C)C(CCC(=O)O)=C(CC5=C(CCC(=O)O)C(C)=C(CC(=C1C)[NH]2)N5[Si](C)(C)C(C)(C)C)[NH]4)[NH]3	5322.2	Semi standard non polar	33892256
Protoporphyrinogen IX,1TBDMS,isomer #4	C=CC1=C2CC3=C(C)C(C=C)=C(CC4=C(C)C(CCC(=O)O)=C(CC5=C(CCC(=O)O)C(C)=C(CC(=C1C)[NH]2)[NH]5)N4[Si](C)(C)C(C)(C)C)[NH]3	5329.2	Semi standard non polar	33892256
Protoporphyrinogen IX,1TBDMS,isomer #5	C=CC1=C2CC3=C(C)C(C=C)=C(CC4=C(C)C(CCC(=O)O)=C(CC5=C(CCC(=O)O)C(C)=C(CC(=C1C)[NH]2)[NH]5)[NH]4)N3[Si](C)(C)C(C)(C)C	5281.3	Semi standard non polar	33892256
Protoporphyrinogen IX,1TBDMS,isomer #6	C=CC1=C2CC3=C(C)C(CCC(=O)O)=C(CC4=C(CCC(=O)O)C(C)=C(CC5=C(C)C(C=C)=C(CC(=C1C)[NH]2)N5[Si](C)(C)C(C)(C)C)[NH]4)[NH]3	5277.3	Semi standard non polar	33892256
Protoporphyrinogen IX,2TBDMS,isomer #1	C=CC1=C2CC3=C(C)C(C=C)=C(CC4=C(C)C(CCC(=O)O[Si](C)(C)C(C)(C)C)=C(CC5=C(CCC(=O)O[Si](C)(C)C(C)(C)C)C(C)=C(CC(=C1C)[NH]2)[NH]5)[NH]4)[NH]3	5355.0	Semi standard non polar	33892256
Protoporphyrinogen IX,2TBDMS,isomer #10	C=CC1=C2CC3=C(C)C(CCC(=O)O)=C(CC4=C(CCC(=O)O)C(C)=C(CC5=C(C)C(C=C)=C(CC(=C1C)[NH]2)N5[Si](C)(C)C(C)(C)C)N4[Si](C)(C)C(C)(C)C)[NH]3	5443.3	Semi standard non polar	33892256
Protoporphyrinogen IX,2TBDMS,isomer #11	C=CC1=C2CC3=C(C)C(C=C)=C(CC4=C(C)C(CCC(=O)O)=C(CC5=C(CCC(=O)O)C(C)=C(CC(=C1C)[NH]2)N5[Si](C)(C)C(C)(C)C)N4[Si](C)(C)C(C)(C)C)[NH]3	5491.6	Semi standard non polar	33892256
Protoporphyrinogen IX,2TBDMS,isomer #12	C=CC1=C2CC3=C(C)C(C=C)=C(CC4=C(C)C(CCC(=O)O)=C(CC5=C(CCC(=O)O)C(C)=C(CC(=C1C)[NH]2)N5[Si](C)(C)C(C)(C)C)[NH]4)N3[Si](C)(C)C(C)(C)C	5437.2	Semi standard non polar	33892256
Protoporphyrinogen IX,2TBDMS,isomer #13	C=CC1=C2CC3=C(C)C(CCC(=O)O)=C(CC4=C(CCC(=O)O)C(C)=C(CC5=C(C)C(C=C)=C(CC(=C1C)[NH]2)N5[Si](C)(C)C(C)(C)C)[NH]4)N3[Si](C)(C)C(C)(C)C	5439.1	Semi standard non polar	33892256
Protoporphyrinogen IX,2TBDMS,isomer #14	C=CC1=C2CC3=C(C)C(C=C)=C(CC4=C(C)C(CCC(=O)O)=C(CC5=C(CCC(=O)O)C(C)=C(CC(=C1C)[NH]2)[NH]5)N4[Si](C)(C)C(C)(C)C)N3[Si](C)(C)C(C)(C)C	5453.1	Semi standard non polar	33892256
Protoporphyrinogen IX,2TBDMS,isomer #15	C=CC1=C2CC3=C(C)C(CCC(=O)O)=C(CC4=C(CCC(=O)O)C(C)=C(CC5=C(C)C(C=C)=C(CC(=C1C)N2[Si](C)(C)C(C)(C)C)N5[Si](C)(C)C(C)(C)C)[NH]4)[NH]3	5409.5	Semi standard non polar	33892256
Protoporphyrinogen IX,2TBDMS,isomer #2	C=CC1=C2CC3=C(C)C(CCC(=O)O[Si](C)(C)C(C)(C)C)=C(CC4=C(CCC(=O)O)C(C)=C(CC5=C(C)C(C=C)=C(CC(=C1C)[NH]2)N5[Si](C)(C)C(C)(C)C)[NH]4)[NH]3	5404.3	Semi standard non polar	33892256
Protoporphyrinogen IX,2TBDMS,isomer #3	C=CC1=C2CC3=C(C)C(C=C)=C(CC4=C(C)C(CCC(=O)O[Si](C)(C)C(C)(C)C)=C(CC5=C(CCC(=O)O)C(C)=C(CC(=C1C)[NH]2)N5[Si](C)(C)C(C)(C)C)[NH]4)[NH]3	5437.0	Semi standard non polar	33892256
Protoporphyrinogen IX,2TBDMS,isomer #4	C=CC1=C2CC3=C(C)C(C=C)=C(CC4=C(C)C(CCC(=O)O[Si](C)(C)C(C)(C)C)=C(CC5=C(CCC(=O)O)C(C)=C(CC(=C1C)[NH]2)[NH]5)N4[Si](C)(C)C(C)(C)C)[NH]3	5438.5	Semi standard non polar	33892256
Protoporphyrinogen IX,2TBDMS,isomer #5	C=CC1=C2CC3=C(C)C(C=C)=C(CC4=C(C)C(CCC(=O)O[Si](C)(C)C(C)(C)C)=C(CC5=C(CCC(=O)O)C(C)=C(CC(=C1C)[NH]2)[NH]5)[NH]4)N3[Si](C)(C)C(C)(C)C	5407.4	Semi standard non polar	33892256
Protoporphyrinogen IX,2TBDMS,isomer #6	C=CC1=C2CC3=C(C)C(CCC(=O)O)=C(CC4=C(CCC(=O)O[Si](C)(C)C(C)(C)C)C(C)=C(CC5=C(C)C(C=C)=C(CC(=C1C)[NH]2)N5[Si](C)(C)C(C)(C)C)[NH]4)[NH]3	5404.5	Semi standard non polar	33892256
Protoporphyrinogen IX,2TBDMS,isomer #7	C=CC1=C2CC3=C(C)C(C=C)=C(CC4=C(C)C(CCC(=O)O)=C(CC5=C(CCC(=O)O[Si](C)(C)C(C)(C)C)C(C)=C(CC(=C1C)[NH]2)N5[Si](C)(C)C(C)(C)C)[NH]4)[NH]3	5433.9	Semi standard non polar	33892256
Protoporphyrinogen IX,2TBDMS,isomer #8	C=CC1=C2CC3=C(C)C(C=C)=C(CC4=C(C)C(CCC(=O)O)=C(CC5=C(CCC(=O)O[Si](C)(C)C(C)(C)C)C(C)=C(CC(=C1C)[NH]2)[NH]5)N4[Si](C)(C)C(C)(C)C)[NH]3	5441.9	Semi standard non polar	33892256
Protoporphyrinogen IX,2TBDMS,isomer #9	C=CC1=C2CC3=C(C)C(C=C)=C(CC4=C(C)C(CCC(=O)O)=C(CC5=C(CCC(=O)O[Si](C)(C)C(C)(C)C)C(C)=C(CC(=C1C)[NH]2)[NH]5)[NH]4)N3[Si](C)(C)C(C)(C)C	5407.4	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Protoporphyrinogen IX GC-MS (Non-derivatized) - 70eV, Positive	splash10-0pi3-1000190000-2785151d048ffcfdafc1	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Protoporphyrinogen IX GC-MS (1 TMS) - 70eV, Positive	splash10-00bc-9000053000-45009d4bbcc7a57d2e8b	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Protoporphyrinogen IX GC-MS ("Protoporphyrinogen IX,1TMS,#1" TMS) - 70eV, Positive	Not Available	2021-10-14	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Protoporphyrinogen IX GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-10-15	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Protoporphyrinogen IX GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-10-15	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Protoporphyrinogen IX GC-MS (TMS_1_4) - 70eV, Positive	Not Available	2021-10-15	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Protoporphyrinogen IX GC-MS (TMS_1_5) - 70eV, Positive	Not Available	2021-10-15	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Protoporphyrinogen IX GC-MS (TMS_1_6) - 70eV, Positive	Not Available	2021-10-15	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Protoporphyrinogen IX GC-MS (TMS_2_1) - 70eV, Positive	Not Available	2021-10-15	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Protoporphyrinogen IX GC-MS (TMS_2_2) - 70eV, Positive	Not Available	2021-10-15	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Protoporphyrinogen IX GC-MS (TMS_2_3) - 70eV, Positive	Not Available	2021-10-15	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Protoporphyrinogen IX GC-MS (TMS_2_4) - 70eV, Positive	Not Available	2021-10-15	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Protoporphyrinogen IX GC-MS (TMS_2_5) - 70eV, Positive	Not Available	2021-10-15	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Protoporphyrinogen IX GC-MS (TMS_2_6) - 70eV, Positive	Not Available	2021-10-15	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Protoporphyrinogen IX GC-MS (TMS_2_7) - 70eV, Positive	Not Available	2021-10-15	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Protoporphyrinogen IX GC-MS (TMS_2_8) - 70eV, Positive	Not Available	2021-10-15	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Protoporphyrinogen IX GC-MS (TMS_2_9) - 70eV, Positive	Not Available	2021-10-15	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Protoporphyrinogen IX GC-MS (TMS_2_10) - 70eV, Positive	Not Available	2021-10-15	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Protoporphyrinogen IX GC-MS (TMS_2_11) - 70eV, Positive	Not Available	2021-10-15	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Protoporphyrinogen IX GC-MS (TMS_2_12) - 70eV, Positive	Not Available	2021-10-15	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Protoporphyrinogen IX GC-MS (TMS_2_13) - 70eV, Positive	Not Available	2021-10-15	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Protoporphyrinogen IX GC-MS (TMS_2_14) - 70eV, Positive	Not Available	2021-10-15	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Protoporphyrinogen IX GC-MS (TMS_2_15) - 70eV, Positive	Not Available	2021-10-15	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Protoporphyrinogen IX GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-10-15	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Protoporphyrinogen IX GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-10-15	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Protoporphyrinogen IX 10V, Positive-QTOF	splash10-0udi-0000190000-7c4ce83e3be73bfccdf6	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Protoporphyrinogen IX 20V, Positive-QTOF	splash10-0pi0-0000490000-affa2d20d85ce7a5a2a1	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Protoporphyrinogen IX 40V, Positive-QTOF	splash10-03dj-0020900000-a1714c4d96457c66da57	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Protoporphyrinogen IX 10V, Negative-QTOF	splash10-014i-0000090000-4148fa37b5b91e3b5a92	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Protoporphyrinogen IX 20V, Negative-QTOF	splash10-05tb-1000090000-27a9f5ba745bc29e2b22	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Protoporphyrinogen IX 40V, Negative-QTOF	splash10-0a4i-9000260000-392765703d0911aa98fc	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Protoporphyrinogen IX 10V, Positive-QTOF	splash10-0gb9-0000090000-9a1be7ce809937d54938	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Protoporphyrinogen IX 20V, Positive-QTOF	splash10-0ldi-0000190000-1a53eff6b6eaea2bd1a8	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Protoporphyrinogen IX 40V, Positive-QTOF	splash10-0a4i-0000790000-030a68500ee48fd68e34	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Protoporphyrinogen IX 10V, Negative-QTOF	splash10-014j-0000090000-4f79e644c71d1a64565b	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Protoporphyrinogen IX 20V, Negative-QTOF	splash10-014j-0000090000-8599f24133cbc58316eb	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Protoporphyrinogen IX 40V, Negative-QTOF	splash10-0a4i-1000950000-a5525829d1d51b8650b0	2021-09-22	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Membrane (predicted from logP)
Mitochondria

Biospecimen Locations

Not Available

Tissue Locations

Liver
Placenta

Pathways

Name	SMPDB/PathBank	KEGG
Porphyrin Metabolism
Acute Intermittent Porphyria		Not Available
Porphyria Variegata (PV)		Not Available
Congenital Erythropoietic Porphyria (CEP) or Gunther Disease		Not Available
Hereditary Coproporphyria (HCP)		Not Available

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Wikipedia Link

Protoporphyrinogen IX

METLIN ID

6003

PubChem Compound

121893

PDB ID

Not Available

ChEBI ID

15435

Food Biomarker Ontology

Not Available

VMH ID

PPPG9

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Wan J, Zhang L, Yang G, Zhan CG: Quantitative structure-activity relationship for cyclic imide derivatives of protoporphyrinogen oxidase inhibitors: a study of quantum chemical descriptors from density functional theory. J Chem Inf Comput Sci. 2004 Nov-Dec;44(6):2099-105. [PubMed:15554680 ]
Herrick AL, Moore MR, Thompson GG, Ford GP, McColl KE: Cholelithiasis in patients with variegate porphyria. J Hepatol. 1991 Jan;12(1):50-3. [PubMed:2007776 ]
Krijt J, Stranska P, Maruna P, Vokurka M, Sanitrak J: Herbicide-induced experimental variegate porphyria in mice: tissue porphyrinogen accumulation and response to porphyrogenic drugs. Can J Physiol Pharmacol. 1997 Oct-Nov;75(10-11):1181-7. [PubMed:9431441 ]
Bloomer JR: Enzyme defects in the porphyrias and their relevance to the biochemical abnormalities in these disorders. J Invest Dermatol. 1981 Jul;77(1):102-6. [PubMed:7252240 ]
de Villiers JN, Kotze MJ, van Heerden CJ, Sadie A, Gardner HF, Liebenberg J, van Zyl R, du Plessis L, Kimberg M, Frank J, Warnich L: Overrepresentation of the founder PPOX gene mutation R59W in a South African patient with severe clinical manifestation of porphyria. Exp Dermatol. 2005 Jan;14(1):50-5. [PubMed:15660919 ]
Corrigall AV, Hift RJ, Adams PA, Kirsch RE: Inhibition of mammalian protoporphyrinogen oxidase by acifluorfen. Biochem Mol Biol Int. 1994 Dec;34(6):1283-9. [PubMed:7697001 ]
Cox TM, Jack N, Lofthouse S, Watling J, Haines J, Warren MJ: King George III and porphyria: an elemental hypothesis and investigation. Lancet. 2005 Jul 23-29;366(9482):332-5. [PubMed:16039338 ]
Winkelman JW, Collins GH: Neurotoxicity of tetraphenylporphinesulfonate TPPS4 and its relation to photodynamic therapy. Photochem Photobiol. 1987 Nov;46(5):801-7. [PubMed:3441503 ]

Enzymes

Enzyme Details

1. Coproporphyrinogen-III oxidase, mitochondrial

General function:: Involved in coproporphyrinogen oxidase activity
Specific function:: Key enzyme in heme biosynthesis. Catalyzes the oxidative decarboxylation of propionic acid side chains of rings A and B of coproporphyrinogen III.
Gene Name:: CPOX
Uniprot ID:: P36551
Molecular weight:: 50151.605

Reactions

Coproporphyrinogen III + Oxygen + Hydrogen Ion → Protoporphyrinogen IX + CO(2) + Water	details
Coproporphyrinogen III + Oxygen → Protoporphyrinogen IX + Carbon dioxide + Water	details

Enzyme Details

2. Protoporphyrinogen oxidase

General function:: Involved in catalytic activity
Specific function:: Catalyzes the 6-electron oxidation of protoporphyrinogen-IX to form protoporphyrin-IX.
Gene Name:: PPOX
Uniprot ID:: P50336
Molecular weight:: 50764.8

Reactions

Protoporphyrinogen IX + Oxygen → Protoporphyrin IX + Hydrogen peroxide	details
Protoporphyrinogen IX + Oxygen → Protoporphyrin IX + Hydrogen peroxide	details

Showing metabocard for Protoporphyrinogen IX (HMDB0001097)

MOL for HMDB0001097 (Protoporphyrinogen IX)

3D MOL for HMDB0001097 (Protoporphyrinogen IX)

3D SDF for HMDB0001097 (Protoporphyrinogen IX)

3D-SDF for HMDB0001097 (Protoporphyrinogen IX)

PDB for HMDB0001097 (Protoporphyrinogen IX)

3D PDB for HMDB0001097 (Protoporphyrinogen IX)

SMILES for HMDB0001097 (Protoporphyrinogen IX)

INCHI for HMDB0001097 (Protoporphyrinogen IX)

Structure for HMDB0001097 (Protoporphyrinogen IX)

3D Structure for HMDB0001097 (Protoporphyrinogen IX)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes

Reactions

Reactions