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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2020-04-23 20:56:37 UTC

HMDB ID

HMDB0000241

Secondary Accession Numbers

HMDB00241

Metabolite Identification

Common Name

Protoporphyrin IX

Description

Protoporphyrins are tetrapyrroles containing 4 methyl, 2 propionic, and 2 vinyl side chains. Protoporphyrin is produced by oxidation of the methylene bridge of protoporphyrinogen. Protoporphyrin IX is the only naturally occurring isomer; it is an intermediate in heme biosynthesis, combining with ferrous iron to form protoheme IX, the heme prosthetic group of hemoglobin. Protoporphyrin IX is created by the enzyme protoporphyrinogen oxidase. The enzyme ferrochelatase converts it into heme. Protoporphyrin IX naturally occurs in small amounts in feces. Protoporphyrin IX is also responsible for the brown pigment (ooporphyrin) of birds' eggs. Protoporphyrin IX is used as a branch point in the biosynthetic pathway leading to heme (by insertion of iron) and chlorophylls (by insertion of Mg and further side-chain transformation). Protoporphyrin IX can be used to treat liver disorders, mainly as the sodium salt. Under certain conditions, protoporphyrin IX can act as a neurotoxin, a phototoxin, and a metabotoxin. A neurotoxin causes damage to nerve cells and nerve tissues. A phototoxin causes cell damage upon exposure to light. 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, it 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

 
  Mrv1652309032023582D          
 
 42 46  0  0  0  0            999 V2000
   15.6785  -11.9918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9224  -12.3185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7388  -11.1649    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.4874  -12.3009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1490  -12.0064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5365  -10.9777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9770  -11.6728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4146  -12.3749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0173  -11.1865    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.8349  -10.2355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9569   -9.4122    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.8249  -11.8284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2085  -11.0554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5296   -9.4940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0596   -8.5923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1370   -9.5579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8784  -10.3244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9021   -8.7450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7132   -9.3657    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.3189   -8.2413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8088   -8.1921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7473   -8.8337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3132   -8.1734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5828   -8.5570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3077   -7.4035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9170   -8.8337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3062   -7.3396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0288   -6.9827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7255   -8.7315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5071  -13.1806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2162  -13.6353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1987  -14.5100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9496  -14.9647    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.4303  -14.9345    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.4193  -13.1955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6530  -13.5753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6578  -14.3958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8914  -14.7757    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.3082  -14.8365    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.9465  -11.8260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7762  -11.6687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1642   -9.4639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 11 15  1  0  0  0  0
 11 16  1  0  0  0  0
 13 17  2  0  0  0  0
 14 18  1  0  0  0  0
 14 19  2  0  0  0  0
 15 20  2  0  0  0  0
 15 21  1  0  0  0  0
 16 22  2  0  0  0  0
 18 23  2  0  0  0  0
 19 24  1  0  0  0  0
 20 25  1  0  0  0  0
 22 26  1  0  0  0  0
 23 27  1  0  0  0  0
  6  7  1  0  0  0  0
 12 13  1  0  0  0  0
 16 17  1  0  0  0  0
 20 22  1  0  0  0  0
 21 24  2  0  0  0  0
 23 24  1  0  0  0  0
 25 28  2  0  0  0  0
 18 29  1  0  0  0  0
  1  2  2  0  0  0  0
  4 30  1  0  0  0  0
  1  3  1  0  0  0  0
 30 31  1  0  0  0  0
  1  4  1  0  0  0  0
 31 32  1  0  0  0  0
  2  5  1  0  0  0  0
 32 33  2  0  0  0  0
  3  6  1  0  0  0  0
 32 34  1  0  0  0  0
  4  7  2  0  0  0  0
  8 35  1  0  0  0  0
  5  8  1  0  0  0  0
 35 36  1  0  0  0  0
  5  9  2  0  0  0  0
 36 37  1  0  0  0  0
  6 10  2  0  0  0  0
 37 38  1  0  0  0  0
  8 12  2  0  0  0  0
 37 39  2  0  0  0  0
  9 13  1  0  0  0  0
 12 40  1  0  0  0  0
 10 14  1  0  0  0  0
  7 41  1  0  0  0  0
 29 42  2  0  0  0  0
M  END

HMDB0000241
     RDKit          3D
Protoporphyrin IX
 76 80  0  0  0  0  0  0  0  0999 V2000
   -3.8863    5.2800    0.4954 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5612    4.2188    0.1914 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1359    2.8470    0.1725 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8898    1.8121   -0.1711 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3027    1.8632   -0.6012 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1247    0.5941   -0.0686 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3203   -0.7664   -0.2996 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3237   -1.7623   -0.3300 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1005   -1.7563   -0.8661 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5357   -2.9419   -0.6086 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2774   -3.4596   -0.9245 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9587   -2.8172   -0.8415 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0215   -1.5951   -0.2991 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2855   -1.1078   -0.2920 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4553    0.1788    0.2193 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4724    1.1752    0.3796 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1785    1.0899    0.7174 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3094    2.3424    0.7001 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6072    2.8216    0.9690 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8168    2.3126    0.5236 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9074    0.9732    0.3496 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7001    3.2640    0.3439 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6068    4.7675    0.2178 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8237    2.5132    0.1434 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1586    3.1083   -0.2335 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0864    3.2689    0.9161 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3469    3.8694    0.3790 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1804    3.1129   -0.1763 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6422    5.2128    0.4610 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1192   -2.1297   -0.8927 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5507   -2.0862   -1.1692 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4573   -2.3649   -0.0254 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4047   -1.5069    1.1378 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0125   -0.3950    1.2399 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6542   -1.8744    2.2480 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3114   -3.1577   -1.2238 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7642   -4.4113   -1.8718 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4484   -3.7406    0.1252 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2352   -5.1491    0.6430 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5931   -3.0070    0.3110 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8032   -3.4078    1.0205 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1934   -4.6495    1.0360 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8867    5.3237    0.7866 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3969    6.2627    0.4509 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6300    4.3739   -0.0956 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3989    1.8000   -1.7060 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8936    1.0052   -0.2032 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8491    2.7670   -0.2653 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3820   -1.0410   -0.4533 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6323   -0.9213   -1.4524 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1450   -4.5105   -1.2734 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5059    0.3600    0.4801 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3822    0.1633    0.9850 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7337    3.7182    1.6108 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1162    5.0464   -0.7298 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0183    5.0991    1.0713 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6112    5.1678    0.3630 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6146    2.4336   -0.9880 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9995    4.0810   -0.7393 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6950    3.9536    1.7014 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3595    2.3380    1.4080 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9885    5.9535    0.2748 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7997   -1.0917   -1.6090 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7891   -2.8460   -1.9756 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3003   -3.4311    0.3516 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5364   -2.3779   -0.3675 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9507   -2.5908    2.8996 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9313   -5.0461   -2.1898 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3892   -4.2228   -2.7688 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4425   -4.9313   -1.1379 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6903   -5.1935    1.6359 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5019   -5.9125   -0.0789 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1136   -5.2138    0.8192 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3686   -2.6629    1.5334 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7050   -5.4660    0.5603 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1203   -4.9273    1.5861 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
  4  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 18 22  1  0
 22 23  1  0
 22 24  2  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  2  0
 27 29  1  0
 14 30  1  0
 30 31  1  0
 31 32  1  0
 32 33  1  0
 33 34  2  0
 33 35  1  0
 30 36  2  0
 36 37  1  0
 10 38  2  0
 38 39  1  0
 38 40  1  0
 40 41  1  0
 41 42  2  3
 20  3  1  0
 21  6  1  0
 40  8  2  0
 36 12  1  0
 24 16  1  0
  1 43  1  0
  1 44  1  0
  2 45  1  0
  5 46  1  0
  5 47  1  0
  5 48  1  0
  7 49  1  0
  9 50  1  0
 11 51  1  0
 15 52  1  0
 17 53  1  0
 19 54  1  0
 23 55  1  0
 23 56  1  0
 23 57  1  0
 25 58  1  0
 25 59  1  0
 26 60  1  0
 26 61  1  0
 29 62  1  0
 31 63  1  0
 31 64  1  0
 32 65  1  0
 32 66  1  0
 35 67  1  0
 37 68  1  0
 37 69  1  0
 37 70  1  0
 39 71  1  0
 39 72  1  0
 39 73  1  0
 41 74  1  0
 42 75  1  0
 42 76  1  0
M  END

 
  Mrv1652309032023582D          
 
 42 46  0  0  0  0            999 V2000
   15.6785  -11.9918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9224  -12.3185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7388  -11.1649    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.4874  -12.3009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1490  -12.0064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5365  -10.9777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9770  -11.6728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4146  -12.3749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0173  -11.1865    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.8349  -10.2355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9569   -9.4122    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.8249  -11.8284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2085  -11.0554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5296   -9.4940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0596   -8.5923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1370   -9.5579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8784  -10.3244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9021   -8.7450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7132   -9.3657    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.3189   -8.2413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8088   -8.1921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7473   -8.8337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3132   -8.1734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5828   -8.5570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3077   -7.4035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9170   -8.8337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3062   -7.3396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0288   -6.9827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7255   -8.7315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5071  -13.1806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2162  -13.6353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1987  -14.5100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9496  -14.9647    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.4303  -14.9345    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.4193  -13.1955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6530  -13.5753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6578  -14.3958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8914  -14.7757    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.3082  -14.8365    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.9465  -11.8260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7762  -11.6687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1642   -9.4639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 11 15  1  0  0  0  0
 11 16  1  0  0  0  0
 13 17  2  0  0  0  0
 14 18  1  0  0  0  0
 14 19  2  0  0  0  0
 15 20  2  0  0  0  0
 15 21  1  0  0  0  0
 16 22  2  0  0  0  0
 18 23  2  0  0  0  0
 19 24  1  0  0  0  0
 20 25  1  0  0  0  0
 22 26  1  0  0  0  0
 23 27  1  0  0  0  0
  6  7  1  0  0  0  0
 12 13  1  0  0  0  0
 16 17  1  0  0  0  0
 20 22  1  0  0  0  0
 21 24  2  0  0  0  0
 23 24  1  0  0  0  0
 25 28  2  0  0  0  0
 18 29  1  0  0  0  0
  1  2  2  0  0  0  0
  4 30  1  0  0  0  0
  1  3  1  0  0  0  0
 30 31  1  0  0  0  0
  1  4  1  0  0  0  0
 31 32  1  0  0  0  0
  2  5  1  0  0  0  0
 32 33  2  0  0  0  0
  3  6  1  0  0  0  0
 32 34  1  0  0  0  0
  4  7  2  0  0  0  0
  8 35  1  0  0  0  0
  5  8  1  0  0  0  0
 35 36  1  0  0  0  0
  5  9  2  0  0  0  0
 36 37  1  0  0  0  0
  6 10  2  0  0  0  0
 37 38  1  0  0  0  0
  8 12  2  0  0  0  0
 37 39  2  0  0  0  0
  9 13  1  0  0  0  0
 12 40  1  0  0  0  0
 10 14  1  0  0  0  0
  7 41  1  0  0  0  0
 29 42  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0000241

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1=C(CCC(O)=O)/C2=C/C3=N/C(=C\C4=C(C)C(C=C)=C(N4)/C=C4\N=C(\C=C\1/N\2)C(C=C)=C4C)/C(C)=C3CCC(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C34H34N4O4/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/h7-8,13-16,35,38H,1-2,9-12H2,3-6H3,(H,39,40)(H,41,42)/b25-13-,26-13-,27-14-,28-15-,29-14-,30-15-,31-16-,32-16-

> <INCHI_KEY>
KSFOVUSSGSKXFI-UJJXFSCMSA-N

> <FORMULA>
C34H34N4O4

> <MOLECULAR_WEIGHT>
562.6582

> <EXACT_MASS>
562.258005596

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
76

> <JCHEM_AVERAGE_POLARIZABILITY>
66.03349029270831

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
4

> <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(21),2,4,6,8(23),9,11,13,15,17,19-undecaen-4-yl]propanoic acid

> <ALOGPS_LOGP>
4.40

> <JCHEM_LOGP>
6.778796967715938

> <ALOGPS_LOGS>
-4.41

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
4.128117407779678

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.684359896427431

> <JCHEM_PKA_STRONGEST_BASIC>
4.958835229373015

> <JCHEM_POLAR_SURFACE_AREA>
131.96

> <JCHEM_REFRACTIVITY>
163.81120000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.17e-02 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(21),2,4,6,8(23),9,11,13,15,17,19-undecaen-4-yl]propanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0000241
     RDKit          3D
Protoporphyrin IX
 76 80  0  0  0  0  0  0  0  0999 V2000
   -3.8863    5.2800    0.4954 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5612    4.2188    0.1914 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1359    2.8470    0.1725 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8898    1.8121   -0.1711 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3027    1.8632   -0.6012 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1247    0.5941   -0.0686 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3203   -0.7664   -0.2996 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3237   -1.7623   -0.3300 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1005   -1.7563   -0.8661 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5357   -2.9419   -0.6086 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2774   -3.4596   -0.9245 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9587   -2.8172   -0.8415 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0215   -1.5951   -0.2991 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2855   -1.1078   -0.2920 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4553    0.1788    0.2193 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4724    1.1752    0.3796 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1785    1.0899    0.7174 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3094    2.3424    0.7001 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6072    2.8216    0.9690 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8168    2.3126    0.5236 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9074    0.9732    0.3496 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7001    3.2640    0.3439 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6068    4.7675    0.2178 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8237    2.5132    0.1434 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1586    3.1083   -0.2335 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0864    3.2689    0.9161 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3469    3.8694    0.3790 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1804    3.1129   -0.1763 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6422    5.2128    0.4610 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1192   -2.1297   -0.8927 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5507   -2.0862   -1.1692 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4573   -2.3649   -0.0254 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4047   -1.5069    1.1378 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0125   -0.3950    1.2399 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6542   -1.8744    2.2480 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3114   -3.1577   -1.2238 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7642   -4.4113   -1.8718 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4484   -3.7406    0.1252 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2352   -5.1491    0.6430 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5931   -3.0070    0.3110 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8032   -3.4078    1.0205 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1934   -4.6495    1.0360 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8867    5.3237    0.7866 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3969    6.2627    0.4509 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6300    4.3739   -0.0956 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3989    1.8000   -1.7060 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8936    1.0052   -0.2032 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8491    2.7670   -0.2653 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3820   -1.0410   -0.4533 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6323   -0.9213   -1.4524 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1450   -4.5105   -1.2734 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5059    0.3600    0.4801 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3822    0.1633    0.9850 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7337    3.7182    1.6108 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1162    5.0464   -0.7298 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0183    5.0991    1.0713 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6112    5.1678    0.3630 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6146    2.4336   -0.9880 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9995    4.0810   -0.7393 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6950    3.9536    1.7014 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3595    2.3380    1.4080 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9885    5.9535    0.2748 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7997   -1.0917   -1.6090 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7891   -2.8460   -1.9756 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3003   -3.4311    0.3516 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5364   -2.3779   -0.3675 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9507   -2.5908    2.8996 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9313   -5.0461   -2.1898 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3892   -4.2228   -2.7688 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4425   -4.9313   -1.1379 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6903   -5.1935    1.6359 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5019   -5.9125   -0.0789 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1136   -5.2138    0.8192 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3686   -2.6629    1.5334 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7050   -5.4660    0.5603 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1203   -4.9273    1.5861 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
  4  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 18 22  1  0
 22 23  1  0
 22 24  2  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  2  0
 27 29  1  0
 14 30  1  0
 30 31  1  0
 31 32  1  0
 32 33  1  0
 33 34  2  0
 33 35  1  0
 30 36  2  0
 36 37  1  0
 10 38  2  0
 38 39  1  0
 38 40  1  0
 40 41  1  0
 41 42  2  3
 20  3  1  0
 21  6  1  0
 40  8  2  0
 36 12  1  0
 24 16  1  0
  1 43  1  0
  1 44  1  0
  2 45  1  0
  5 46  1  0
  5 47  1  0
  5 48  1  0
  7 49  1  0
  9 50  1  0
 11 51  1  0
 15 52  1  0
 17 53  1  0
 19 54  1  0
 23 55  1  0
 23 56  1  0
 23 57  1  0
 25 58  1  0
 25 59  1  0
 26 60  1  0
 26 61  1  0
 29 62  1  0
 31 63  1  0
 31 64  1  0
 32 65  1  0
 32 66  1  0
 35 67  1  0
 37 68  1  0
 37 69  1  0
 37 70  1  0
 39 71  1  0
 39 72  1  0
 39 73  1  0
 41 74  1  0
 42 75  1  0
 42 76  1  0
M  END

HEADER    PROTEIN                                 03-SEP-20   NONE
TITLE     NULL                                                        
COMPND    MOLECULE:                                                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-SEP-20         0                                  
HETATM    1  C   UNK     0      29.267 -22.385   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      27.855 -22.995   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0      29.379 -20.841   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0      30.776 -22.962   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      26.411 -22.412   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      30.868 -20.492   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      31.690 -21.789   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      25.041 -23.100   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0      26.166 -20.881   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0      31.425 -19.106   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0      26.053 -17.569   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0      23.940 -22.080   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      24.656 -20.637   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      30.855 -17.722   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      26.245 -16.039   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      24.522 -17.841   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      24.040 -19.272   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      31.551 -16.324   0.000  0.00  0.00           C+0
HETATM   19  N   UNK     0      29.331 -17.483   0.000  0.00  0.00           N+0
HETATM   20  C   UNK     0      24.862 -15.384   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      27.643 -15.292   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      23.795 -16.490   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      30.451 -15.257   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      29.088 -15.973   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      24.841 -13.820   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      22.245 -16.490   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      30.438 -13.701   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      26.187 -13.034   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      33.088 -16.299   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      30.813 -24.604   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      32.137 -25.453   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      32.104 -27.085   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      33.506 -27.934   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0      30.670 -27.878   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0      25.049 -24.632   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      23.619 -25.341   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      23.628 -26.872   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0      22.197 -27.581   0.000  0.00  0.00           O+0
HETATM   39  O   UNK     0      24.842 -27.695   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0      22.300 -22.075   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      33.182 -21.782   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      33.907 -17.666   0.000  0.00  0.00           C+0
CONECT    1    2    3    4                                                  
CONECT    2    1    5                                                       
CONECT    3    1    6                                                       
CONECT    4   30    1    7                                                  
CONECT    5    2    8    9                                                  
CONECT    6    7    3   10                                                  
CONECT    7    6    4   41                                                  
CONECT    8   35    5   12                                                  
CONECT    9    5   13                                                       
CONECT   10    6   14                                                       
CONECT   11   15   16                                                       
CONECT   12   13    8   40                                                  
CONECT   13   17   12    9                                                  
CONECT   14   18   19   10                                                  
CONECT   15   11   20   21                                                  
CONECT   16   11   22   17                                                  
CONECT   17   13   16                                                       
CONECT   18   14   23   29                                                  
CONECT   19   14   24                                                       
CONECT   20   15   25   22                                                  
CONECT   21   15   24                                                       
CONECT   22   16   26   20                                                  
CONECT   23   18   27   24                                                  
CONECT   24   19   21   23                                                  
CONECT   25   20   28                                                       
CONECT   26   22                                                            
CONECT   27   23                                                            
CONECT   28   25                                                            
CONECT   29   18   42                                                       
CONECT   30    4   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32                                                            
CONECT   35    8   36                                                       
CONECT   36   35   37                                                       
CONECT   37   36   38   39                                                  
CONECT   38   37                                                            
CONECT   39   37                                                            
CONECT   40   12                                                            
CONECT   41    7                                                            
CONECT   42   29                                                            
MASTER        0    0    0    0    0    0    0    0   42    0   92    0
END

COMPND    HMDB0000241
HETATM    1  C1  UNL     1      -3.886   5.280   0.495  1.00  0.00           C  
HETATM    2  C2  UNL     1      -4.561   4.219   0.191  1.00  0.00           C  
HETATM    3  C3  UNL     1      -4.136   2.847   0.173  1.00  0.00           C  
HETATM    4  C4  UNL     1      -4.890   1.812  -0.171  1.00  0.00           C  
HETATM    5  C5  UNL     1      -6.303   1.863  -0.601  1.00  0.00           C  
HETATM    6  C6  UNL     1      -4.125   0.594  -0.069  1.00  0.00           C  
HETATM    7  C7  UNL     1      -4.320  -0.766  -0.300  1.00  0.00           C  
HETATM    8  C8  UNL     1      -3.324  -1.762  -0.330  1.00  0.00           C  
HETATM    9  N1  UNL     1      -2.100  -1.756  -0.866  1.00  0.00           N  
HETATM   10  C9  UNL     1      -1.536  -2.942  -0.609  1.00  0.00           C  
HETATM   11  C10 UNL     1      -0.277  -3.460  -0.925  1.00  0.00           C  
HETATM   12  C11 UNL     1       0.959  -2.817  -0.841  1.00  0.00           C  
HETATM   13  N2  UNL     1       1.022  -1.595  -0.299  1.00  0.00           N  
HETATM   14  C12 UNL     1       2.286  -1.108  -0.292  1.00  0.00           C  
HETATM   15  C13 UNL     1       2.455   0.179   0.219  1.00  0.00           C  
HETATM   16  C14 UNL     1       1.472   1.175   0.380  1.00  0.00           C  
HETATM   17  N3  UNL     1       0.179   1.090   0.717  1.00  0.00           N  
HETATM   18  C15 UNL     1      -0.309   2.342   0.700  1.00  0.00           C  
HETATM   19  C16 UNL     1      -1.607   2.822   0.969  1.00  0.00           C  
HETATM   20  C17 UNL     1      -2.817   2.313   0.524  1.00  0.00           C  
HETATM   21  N4  UNL     1      -2.907   0.973   0.350  1.00  0.00           N  
HETATM   22  C18 UNL     1       0.700   3.264   0.344  1.00  0.00           C  
HETATM   23  C19 UNL     1       0.607   4.768   0.218  1.00  0.00           C  
HETATM   24  C20 UNL     1       1.824   2.513   0.143  1.00  0.00           C  
HETATM   25  C21 UNL     1       3.159   3.108  -0.233  1.00  0.00           C  
HETATM   26  C22 UNL     1       4.086   3.269   0.916  1.00  0.00           C  
HETATM   27  C23 UNL     1       5.347   3.869   0.379  1.00  0.00           C  
HETATM   28  O1  UNL     1       6.180   3.113  -0.176  1.00  0.00           O  
HETATM   29  O2  UNL     1       5.642   5.213   0.461  1.00  0.00           O  
HETATM   30  C24 UNL     1       3.119  -2.130  -0.893  1.00  0.00           C  
HETATM   31  C25 UNL     1       4.551  -2.086  -1.169  1.00  0.00           C  
HETATM   32  C26 UNL     1       5.457  -2.365  -0.025  1.00  0.00           C  
HETATM   33  C27 UNL     1       5.405  -1.507   1.138  1.00  0.00           C  
HETATM   34  O3  UNL     1       6.012  -0.395   1.240  1.00  0.00           O  
HETATM   35  O4  UNL     1       4.654  -1.874   2.248  1.00  0.00           O  
HETATM   36  C28 UNL     1       2.311  -3.158  -1.224  1.00  0.00           C  
HETATM   37  C29 UNL     1       2.764  -4.411  -1.872  1.00  0.00           C  
HETATM   38  C30 UNL     1      -2.448  -3.741   0.125  1.00  0.00           C  
HETATM   39  C31 UNL     1      -2.235  -5.149   0.643  1.00  0.00           C  
HETATM   40  C32 UNL     1      -3.593  -3.007   0.311  1.00  0.00           C  
HETATM   41  C33 UNL     1      -4.803  -3.408   1.020  1.00  0.00           C  
HETATM   42  C34 UNL     1      -5.193  -4.650   1.036  1.00  0.00           C  
HETATM   43  H1  UNL     1      -2.887   5.324   0.787  1.00  0.00           H  
HETATM   44  H2  UNL     1      -4.397   6.263   0.451  1.00  0.00           H  
HETATM   45  H3  UNL     1      -5.630   4.374  -0.096  1.00  0.00           H  
HETATM   46  H4  UNL     1      -6.399   1.800  -1.706  1.00  0.00           H  
HETATM   47  H5  UNL     1      -6.894   1.005  -0.203  1.00  0.00           H  
HETATM   48  H6  UNL     1      -6.849   2.767  -0.265  1.00  0.00           H  
HETATM   49  H7  UNL     1      -5.382  -1.041  -0.453  1.00  0.00           H  
HETATM   50  H8  UNL     1      -1.632  -0.921  -1.452  1.00  0.00           H  
HETATM   51  H9  UNL     1      -0.145  -4.510  -1.273  1.00  0.00           H  
HETATM   52  H10 UNL     1       3.506   0.360   0.480  1.00  0.00           H  
HETATM   53  H11 UNL     1      -0.382   0.163   0.985  1.00  0.00           H  
HETATM   54  H12 UNL     1      -1.734   3.718   1.611  1.00  0.00           H  
HETATM   55  H13 UNL     1       0.116   5.046  -0.730  1.00  0.00           H  
HETATM   56  H14 UNL     1      -0.018   5.099   1.071  1.00  0.00           H  
HETATM   57  H15 UNL     1       1.611   5.168   0.363  1.00  0.00           H  
HETATM   58  H16 UNL     1       3.615   2.434  -0.988  1.00  0.00           H  
HETATM   59  H17 UNL     1       2.999   4.081  -0.739  1.00  0.00           H  
HETATM   60  H18 UNL     1       3.695   3.954   1.701  1.00  0.00           H  
HETATM   61  H19 UNL     1       4.360   2.338   1.408  1.00  0.00           H  
HETATM   62  H20 UNL     1       4.988   5.954   0.275  1.00  0.00           H  
HETATM   63  H21 UNL     1       4.800  -1.092  -1.609  1.00  0.00           H  
HETATM   64  H22 UNL     1       4.789  -2.846  -1.976  1.00  0.00           H  
HETATM   65  H23 UNL     1       5.300  -3.431   0.352  1.00  0.00           H  
HETATM   66  H24 UNL     1       6.536  -2.378  -0.368  1.00  0.00           H  
HETATM   67  H25 UNL     1       4.951  -2.591   2.900  1.00  0.00           H  
HETATM   68  H26 UNL     1       1.931  -5.046  -2.190  1.00  0.00           H  
HETATM   69  H27 UNL     1       3.389  -4.223  -2.769  1.00  0.00           H  
HETATM   70  H28 UNL     1       3.443  -4.931  -1.138  1.00  0.00           H  
HETATM   71  H29 UNL     1      -2.690  -5.193   1.636  1.00  0.00           H  
HETATM   72  H30 UNL     1      -2.502  -5.912  -0.079  1.00  0.00           H  
HETATM   73  H31 UNL     1      -1.114  -5.214   0.819  1.00  0.00           H  
HETATM   74  H32 UNL     1      -5.369  -2.663   1.533  1.00  0.00           H  
HETATM   75  H33 UNL     1      -4.705  -5.466   0.560  1.00  0.00           H  
HETATM   76  H34 UNL     1      -6.120  -4.927   1.586  1.00  0.00           H  
CONECT    1    2    2   43   44
CONECT    2    3   45
CONECT    3    4    4   20
CONECT    4    5    6
CONECT    5   46   47   48
CONECT    6    7    7   21
CONECT    7    8   49
CONECT    8    9   40   40
CONECT    9   10   50
CONECT   10   11   38   38
CONECT   11   12   12   51
CONECT   12   13   36
CONECT   13   14   14
CONECT   14   15   30
CONECT   15   16   16   52
CONECT   16   17   24
CONECT   17   18   53
CONECT   18   19   19   22
CONECT   19   20   54
CONECT   20   21   21
CONECT   22   23   24   24
CONECT   23   55   56   57
CONECT   24   25
CONECT   25   26   58   59
CONECT   26   27   60   61
CONECT   27   28   28   29
CONECT   29   62
CONECT   30   31   36   36
CONECT   31   32   63   64
CONECT   32   33   65   66
CONECT   33   34   34   35
CONECT   35   67
CONECT   36   37
CONECT   37   68   69   70
CONECT   38   39   40
CONECT   39   71   72   73
CONECT   40   41
CONECT   41   42   42   74
CONECT   42   75   76
END

HMDB0000241
     RDKit          3D
Protoporphyrin IX
 76 80  0  0  0  0  0  0  0  0999 V2000
   -3.8863    5.2800    0.4954 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5612    4.2188    0.1914 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1359    2.8470    0.1725 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8898    1.8121   -0.1711 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3027    1.8632   -0.6012 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1247    0.5941   -0.0686 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3203   -0.7664   -0.2996 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3237   -1.7623   -0.3300 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1005   -1.7563   -0.8661 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5357   -2.9419   -0.6086 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2774   -3.4596   -0.9245 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9587   -2.8172   -0.8415 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0215   -1.5951   -0.2991 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2855   -1.1078   -0.2920 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4553    0.1788    0.2193 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4724    1.1752    0.3796 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1785    1.0899    0.7174 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3094    2.3424    0.7001 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6072    2.8216    0.9690 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8168    2.3126    0.5236 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9074    0.9732    0.3496 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7001    3.2640    0.3439 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6068    4.7675    0.2178 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8237    2.5132    0.1434 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1586    3.1083   -0.2335 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0864    3.2689    0.9161 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3469    3.8694    0.3790 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1804    3.1129   -0.1763 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6422    5.2128    0.4610 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1192   -2.1297   -0.8927 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5507   -2.0862   -1.1692 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4573   -2.3649   -0.0254 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4047   -1.5069    1.1378 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0125   -0.3950    1.2399 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6542   -1.8744    2.2480 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3114   -3.1577   -1.2238 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7642   -4.4113   -1.8718 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4484   -3.7406    0.1252 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2352   -5.1491    0.6430 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5931   -3.0070    0.3110 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8032   -3.4078    1.0205 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1934   -4.6495    1.0360 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8867    5.3237    0.7866 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3969    6.2627    0.4509 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6300    4.3739   -0.0956 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3989    1.8000   -1.7060 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8936    1.0052   -0.2032 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8491    2.7670   -0.2653 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3820   -1.0410   -0.4533 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6323   -0.9213   -1.4524 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1450   -4.5105   -1.2734 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5059    0.3600    0.4801 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3822    0.1633    0.9850 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7337    3.7182    1.6108 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1162    5.0464   -0.7298 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0183    5.0991    1.0713 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6112    5.1678    0.3630 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6146    2.4336   -0.9880 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9995    4.0810   -0.7393 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6950    3.9536    1.7014 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3595    2.3380    1.4080 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9885    5.9535    0.2748 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7997   -1.0917   -1.6090 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7891   -2.8460   -1.9756 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3003   -3.4311    0.3516 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5364   -2.3779   -0.3675 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9507   -2.5908    2.8996 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9313   -5.0461   -2.1898 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3892   -4.2228   -2.7688 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4425   -4.9313   -1.1379 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6903   -5.1935    1.6359 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5019   -5.9125   -0.0789 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1136   -5.2138    0.8192 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3686   -2.6629    1.5334 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7050   -5.4660    0.5603 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1203   -4.9273    1.5861 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
  4  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 18 22  1  0
 22 23  1  0
 22 24  2  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  2  0
 27 29  1  0
 14 30  1  0
 30 31  1  0
 31 32  1  0
 32 33  1  0
 33 34  2  0
 33 35  1  0
 30 36  2  0
 36 37  1  0
 10 38  2  0
 38 39  1  0
 38 40  1  0
 40 41  1  0
 41 42  2  3
 20  3  1  0
 21  6  1  0
 40  8  2  0
 36 12  1  0
 24 16  1  0
  1 43  1  0
  1 44  1  0
  2 45  1  0
  5 46  1  0
  5 47  1  0
  5 48  1  0
  7 49  1  0
  9 50  1  0
 11 51  1  0
 15 52  1  0
 17 53  1  0
 19 54  1  0
 23 55  1  0
 23 56  1  0
 23 57  1  0
 25 58  1  0
 25 59  1  0
 26 60  1  0
 26 61  1  0
 29 62  1  0
 31 63  1  0
 31 64  1  0
 32 65  1  0
 32 66  1  0
 35 67  1  0
 37 68  1  0
 37 69  1  0
 37 70  1  0
 39 71  1  0
 39 72  1  0
 39 73  1  0
 41 74  1  0
 42 75  1  0
 42 76  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
3,3'-(3,7,12,17-Tetramethyl-8,13-divinyl-21H,23H-porphine-2,18-diyl)-bis-propionic acid	ChEBI
3,7,12,17-Tetramethyl-8,13-divinylporphyrin-2,18-dipropanoic acid	ChEBI
H2PpIX	ChEBI
Kammerer's prophyrin	ChEBI
Ooporphyrin	ChEBI
Porphyrinogen IX	ChEBI
3,3'-(3,7,12,17-Tetramethyl-8,13-divinyl-21H,23H-porphine-2,18-diyl)-bis-propionate	Generator
3,7,12,17-Tetramethyl-8,13-divinylporphyrin-2,18-dipropanoate	Generator
3,3'-(3,7,12,17-Tetramethyl-8,13-divinylporphine-2,18-diyl)di	HMDB
PpIX	HMDB
Protoporphyrin	HMDB
Protoporphyrin-"ix"	HMDB
Protoporphyrin-IX	HMDB

Chemical Formula

C₃₄H₃₄N₄O₄

Average Molecular Weight

562.6582

Monoisotopic Molecular Weight

562.258005596

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(21),2,4,6,8(23),9,11,13,15,17,19-undecaen-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(21),2,4,6,8(23),9,11,13,15,17,19-undecaen-4-yl]propanoic acid

CAS Registry Number

553-12-8

SMILES

CC1=C(CCC(O)=O)/C2=C/C3=N/C(=C\C4=C(C)C(C=C)=C(N4)/C=C4\N=C(\C=C\1/N\2)C(C=C)=C4C)/C(C)=C3CCC(O)=O

InChI Identifier

InChI=1S/C34H34N4O4/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/h7-8,13-16,35,38H,1-2,9-12H2,3-6H3,(H,39,40)(H,41,42)/b25-13-,26-13-,27-14-,28-15-,29-14-,30-15-,31-16-,32-16-

InChI Key

KSFOVUSSGSKXFI-UJJXFSCMSA-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

Not Available

Substituents

Not Available

Molecular Framework

Not Available

External Descriptors

Not Available

Ontology

Physiological effect

Health effect

Genetic disorder

Inborn errors of metabolism

Porphyria (HMDB: HMDB0000241)
Hereditary coproporphyria (HMDB: HMDB0000241)

Adipose tissue (HMDB: HMDB0000241)
Adipose tissue (HMDB: HMDB0000241)

Epithelium

Epidermis (HMDB: HMDB0000241)

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 13765301)
Lymph (HMDB: HMDB0000241)

Cellular substructure

Organelle

Mitochondrion (HMDB: HMDB0000241)

Cell

Fibroblast

Fibroblast (HMDB: HMDB0000241)

Hematocyte

Platelet (HMDB: HMDB0000241)

Organ substructure

Adrenal medulla (HMDB: HMDB0000241)

Organ

Gland

Thyroid gland (HMDB: HMDB0000241)
Thyroid gland (HMDB: HMDB0000241)

Stratum Corneum (HMDB: HMDB0000241)
T-Lymphocyte (HMDB: HMDB0000241)
Gastrointestinal Tract (HMDB: HMDB0000241)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0000241)

Source

Exogenous

Exogenous (HMDB: HMDB0000241)

Food

Food (HMDB: HMDB0000241)

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)

Herb and spice mixture

Curry powder (FooDB: FOOD00678)

Vegetable

Cabbage

Onion-family vegetable

Root vegetable

Shoot vegetable

Leaf vegetable

Common beet (FooDB: FOOD00025)
Endive (FooDB: FOOD00048)
Rocket salad (ssp.) (FooDB: FOOD00077)
Swamp cabbage (FooDB: FOOD00091)
Lettuce (FooDB: FOOD00095)
Garden cress (FooDB: FOOD00099)
Spinach (FooDB: FOOD00178)
Swiss chard (FooDB: FOOD00237)
Chicory leaves (FooDB: FOOD00250)
Garland chrysanthemum (FooDB: FOOD00333)
Corn salad (FooDB: FOOD00340)
Jute (FooDB: FOOD00389)
Lambsquarters (FooDB: FOOD00394)
Malabar spinach (FooDB: FOOD00404)
New Zealand spinach (FooDB: FOOD00415)
Yautia (FooDB: FOOD00510)
Ostrich fern (FooDB: FOOD00556)
Romaine lettuce (FooDB: FOOD00888)
Iceberg lettuce (FooDB: FOOD00973)
Pea shoots (FooDB: FOOD00975)
Yau choy (FooDB: FOOD00976)
Water spinach (FooDB: FOOD00977)

Fruit vegetable

Pepper (FooDB: FOOD00040)
Olive (FooDB: FOOD00121)
Avocado (FooDB: FOOD00130)
Garden tomato (FooDB: FOOD00171)
Cherry tomato (FooDB: FOOD00172)
Garden tomato (var.) (FooDB: FOOD00173)
Eggplant (FooDB: FOOD00174)
Pepper (C. baccatum) (FooDB: FOOD00231)
Pepper (C. chinense) (FooDB: FOOD00232)
Pepper (Capsicum) (FooDB: FOOD00233)
Groundcherry (FooDB: FOOD00371)
Pepper (C. frutescens) (FooDB: FOOD00428)
Mexican groundcherry (FooDB: FOOD00491)
Pepper (C. pubescens) (FooDB: FOOD00849)
Green bell pepper (FooDB: FOOD00877)
Yellow bell pepper (FooDB: FOOD00878)
Orange bell pepper (FooDB: FOOD00879)
Red bell pepper (FooDB: FOOD00880)
Italian sweet red pepper (FooDB: FOOD00881)
Jalapeno pepper (FooDB: FOOD00955)
Cubanelle pepper (FooDB: FOOD00971)

Tuber

Stalk vegetable

Other vegetable

Giant butterbur (FooDB: FOOD00314)
Carob (FooDB: FOOD00321)
Chinese water chestnut (FooDB: FOOD00332)
Horseradish tree (FooDB: FOOD00379)
Sacred lotus (FooDB: FOOD00402)
Nopal (FooDB: FOOD00416)
Okra (FooDB: FOOD00420)
Sesbania flower (FooDB: FOOD00469)
Agave (FooDB: FOOD00563)
Narrowleaf cattail (FooDB: FOOD00564)
Heart of palm (FooDB: FOOD00718)
Tree fern (FooDB: FOOD00797)

Mushroom

Castanospermum australe (FooDB: FOOD00893)
Gentiana lutea (FooDB: FOOD00894)
Juniperus communis (FooDB: FOOD00895)
Albizia gummifera (FooDB: FOOD00896)

Fruit

Tropical fruit

Citrus

Lime (FooDB: FOOD00053)
Lemon (FooDB: FOOD00054)
Pummelo (FooDB: FOOD00055)
Mandarin orange (Clementine, Tangerine) (FooDB: FOOD00056)
Sweet orange (FooDB: FOOD00057)
Grapefruit/Pummelo hybrid (FooDB: FOOD00255)
Grapefruit (FooDB: FOOD00256)
Persian lime (FooDB: FOOD00543)
Sour orange (FooDB: FOOD00918)
Mikan (FooDB: FOOD00932)
Clementine (FooDB: FOOD00959)

Pome

Berry

Black crowberry (FooDB: FOOD00075)
Strawberry (FooDB: FOOD00083)
Black huckleberry (FooDB: FOOD00084)
Sea-buckthornberry (FooDB: FOOD00087)
Mulberry (FooDB: FOOD00116)
Black mulberry (FooDB: FOOD00117)
Black chokeberry (FooDB: FOOD00136)
Blackcurrant (FooDB: FOOD00155)
Redcurrant (FooDB: FOOD00156)
Gooseberry (FooDB: FOOD00157)
Cloudberry (FooDB: FOOD00161)
Red raspberry (FooDB: FOOD00162)
Black raspberry (FooDB: FOOD00163)
Black elderberry (FooDB: FOOD00166)
Rowanberry (FooDB: FOOD00176)
Vaccinium (Blueberry, Cranberry, Huckleberry) (FooDB: FOOD00188)
Lowbush blueberry (FooDB: FOOD00189)
Sparkleberry (FooDB: FOOD00190)
Highbush blueberry (FooDB: FOOD00191)
American cranberry (FooDB: FOOD00192)
Bilberry (FooDB: FOOD00193)
Lingonberry (FooDB: FOOD00194)
Muscadine grape (FooDB: FOOD00203)
Common grape (FooDB: FOOD00204)
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)
Elderberry (FooDB: FOOD00358)
Grape (FooDB: FOOD00369)
Alaska blueberry (FooDB: FOOD00380)
Loganberry (FooDB: FOOD00400)
Ohelo berry (FooDB: FOOD00419)
Salmonberry (FooDB: FOOD00456)
Strawberry guava (FooDB: FOOD00482)
Boysenberry (FooDB: FOOD00542)
Chinese bayberry (FooDB: FOOD00852)
Saskatoon berry (FooDB: FOOD00884)
Nanking cherry (FooDB: FOOD00885)
Rabbiteye blueberry (FooDB: FOOD00898)
Blackberry (FooDB: FOOD00906)
Partridge berry (FooDB: FOOD00931)
Green grape (FooDB: FOOD00964)
Red grape (FooDB: FOOD00965)
Black plum (FooDB: FOOD00966)
Black raisin (FooDB: FOOD00968)
Chinese plum (FooDB: FOOD00978)
Green plum (FooDB: FOOD00979)
Wampee (FooDB: FOOD00980)
Goji (FooDB: FOOD00982)
Monk fruit (FooDB: FOOD00983)
Hawthorn (FooDB: FOOD00985)
Lantern fruit (FooDB: FOOD00986)
Cape gooseberry (FooDB: FOOD00988)

Other fruit

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

Drupe

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

Nut

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

Cereal and cereal product

Cereal

Cereal product

Pasta (FooDB: FOOD00273)
Bulgur (FooDB: FOOD00741)
Semolina (FooDB: FOOD00745)
Flour (FooDB: FOOD00799)

Dough

Sourdough (FooDB: FOOD00275)

Leavened bread

Flat bread

Other bread

Potato bread (FooDB: FOOD00811)

Sweet bread

Raisin bread (FooDB: FOOD00817)

Pulse

Pea

Lentil

Lentils (FooDB: FOOD00098)

Other pulse

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

Bean

Green lentil (FooDB: FOOD00970)

Gourd

Watermelon (FooDB: FOOD00052)
Muskmelon (FooDB: FOOD00064)
Cucumber (FooDB: FOOD00065)
Cucurbita (FooDB: FOOD00066)
Bitter gourd (FooDB: FOOD00115)
Winter squash (FooDB: FOOD00283)
Butternut squash (FooDB: FOOD00317)
Calabash (FooDB: FOOD00318)
Chayote (FooDB: FOOD00325)
Towel gourd (FooDB: FOOD00492)
Wax gourd (FooDB: FOOD00499)
Tinda (FooDB: FOOD00559)
Horned melon (FooDB: FOOD00761)
Sunburst squash (pattypan squash) (FooDB: FOOD00874)
Green zucchini (FooDB: FOOD00875)
Yellow zucchini (FooDB: FOOD00876)
Japanese pumpkin (FooDB: FOOD00886)
Acorn squash (FooDB: FOOD00972)
Cantaloupe melon (FooDB: FOOD00984)

Coffee and coffee product

Coffee

Arabica coffee (FooDB: FOOD00059)
Robusta coffee (FooDB: FOOD00060)

Soy

Soy bean (FooDB: FOOD00085)

Soy product

Soy sauce (FooDB: FOOD00694)
Miso (FooDB: FOOD00695)
Tofu (FooDB: FOOD00696)
Soy milk (FooDB: FOOD00736)
Soy cream (FooDB: FOOD00784)

Dish

Other dish

Taco shell (FooDB: FOOD00991)
Tostada shell (FooDB: FOOD00992)

Tea

Herbal tea

Hibiscus tea (FooDB: FOOD00723)
Greenthread tea (FooDB: FOOD00820)

Baking good

Wrapper

Wonton wrapper (FooDB: FOOD00818)

Endogenous

Endogenous (HMDB: HMDB0000241)

Plant

Plant (HMDB: HMDB0000241)

Process

Role

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	300 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.17 mg/mL at 25 °C	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M-H]-	MetCCS_train_neg	245.232	30932474
[M+H]+	MetCCS_train_pos	241.419	30932474
[M-H]-	Not Available	245.232	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000317
[M+H]+	Not Available	242.26	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000317

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.022 g/L	ALOGPS
logP	4.4	ALOGPS
logP	6.78	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Acidic)	3.68	ChemAxon
pKa (Strongest Basic)	4.96	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	131.96 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	163.81 m³·mol⁻¹	ChemAxon
Polarizability	66.03 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
AllCCS	[M+H]+	237.435	32859911
AllCCS	[M-H]-	230.792	32859911
DeepCCS	[M+H]+	251.038	30932474
DeepCCS	[M-H]-	249.213	30932474
DeepCCS	[M-2H]-	282.456	30932474
DeepCCS	[M+Na]+	256.644	30932474
AllCCS	[M+H]+	237.4	32859911
AllCCS	[M+H-H2O]+	235.8	32859911
AllCCS	[M+NH4]+	239.0	32859911
AllCCS	[M+Na]+	239.4	32859911
AllCCS	[M-H]-	230.8	32859911
AllCCS	[M+Na-2H]-	232.3	32859911
AllCCS	[M+HCOO]-	234.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Protoporphyrin IX	CC1=C(CCC(O)=O)/C2=C/C3=N/C(=C\C4=C(C)C(C=C)=C(N4)/C=C4\N=C(\C=C\1/N\2)C(C=C)=C4C)/C(C)=C3CCC(O)=O	6245.9	Standard polar	33892256
Protoporphyrin IX	CC1=C(CCC(O)=O)/C2=C/C3=N/C(=C\C4=C(C)C(C=C)=C(N4)/C=C4\N=C(\C=C\1/N\2)C(C=C)=C4C)/C(C)=C3CCC(O)=O	3858.4	Standard non polar	33892256
Protoporphyrin IX	CC1=C(CCC(O)=O)/C2=C/C3=N/C(=C\C4=C(C)C(C=C)=C(N4)/C=C4\N=C(\C=C\1/N\2)C(C=C)=C4C)/C(C)=C3CCC(O)=O	5813.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Protoporphyrin IX,1TMS,isomer #1	C=CC1=C(C)C2=CC3=C(C=C)C(C)=C(C=C4N=C(C=C5[NH]C(=CC1=N2)C(C)=C5CCC(=O)O[Si](C)(C)C)C(CCC(=O)O)=C4C)[NH]3	5372.5	Semi standard non polar	33892256
Protoporphyrin IX,1TMS,isomer #2	C=CC1=C(C)C2=CC3=C(C=C)C(C)=C(C=C4N=C(C=C5[NH]C(=CC1=N2)C(C)=C5CCC(=O)O)C(CCC(=O)O[Si](C)(C)C)=C4C)[NH]3	5357.7	Semi standard non polar	33892256
Protoporphyrin IX,1TMS,isomer #3	C=CC1=C(C)C2=CC3=C(C=C)C(C)=C(C=C4N=C(C=C5[NH]C(=CC1=N2)C(C)=C5CCC(=O)O)C(CCC(=O)O)=C4C)N3[Si](C)(C)C	5429.1	Semi standard non polar	33892256
Protoporphyrin IX,1TMS,isomer #4	C=CC1=C(C)C2=CC3=C(C=C)C(C)=C(C=C4N=C(C=C5C(CCC(=O)O)=C(C)C(=CC1=N2)N5[Si](C)(C)C)C(CCC(=O)O)=C4C)[NH]3	5403.2	Semi standard non polar	33892256
Protoporphyrin IX,2TMS,isomer #1	C=CC1=C(C)C2=CC3=C(C=C)C(C)=C(C=C4N=C(C=C5[NH]C(=CC1=N2)C(C)=C5CCC(=O)O[Si](C)(C)C)C(CCC(=O)O[Si](C)(C)C)=C4C)[NH]3	5260.4	Semi standard non polar	33892256
Protoporphyrin IX,2TMS,isomer #2	C=CC1=C(C)C2=CC3=C(C=C)C(C)=C(C=C4N=C(C=C5[NH]C(=CC1=N2)C(C)=C5CCC(=O)O[Si](C)(C)C)C(CCC(=O)O)=C4C)N3[Si](C)(C)C	5350.2	Semi standard non polar	33892256
Protoporphyrin IX,2TMS,isomer #3	C=CC1=C(C)C2=CC3=C(C=C)C(C)=C(C=C4N=C(C=C5C(CCC(=O)O[Si](C)(C)C)=C(C)C(=CC1=N2)N5[Si](C)(C)C)C(CCC(=O)O)=C4C)[NH]3	5328.0	Semi standard non polar	33892256
Protoporphyrin IX,2TMS,isomer #4	C=CC1=C(C)C2=CC3=C(C=C)C(C)=C(C=C4N=C(C=C5[NH]C(=CC1=N2)C(C)=C5CCC(=O)O)C(CCC(=O)O[Si](C)(C)C)=C4C)N3[Si](C)(C)C	5332.6	Semi standard non polar	33892256
Protoporphyrin IX,2TMS,isomer #5	C=CC1=C(C)C2=CC3=C(C=C)C(C)=C(C=C4N=C(C=C5C(CCC(=O)O)=C(C)C(=CC1=N2)N5[Si](C)(C)C)C(CCC(=O)O[Si](C)(C)C)=C4C)[NH]3	5309.9	Semi standard non polar	33892256
Protoporphyrin IX,2TMS,isomer #6	C=CC1=C(C)C2=CC3=C(C=C)C(C)=C(C=C4N=C(C=C5C(CCC(=O)O)=C(C)C(=CC1=N2)N5[Si](C)(C)C)C(CCC(=O)O)=C4C)N3[Si](C)(C)C	5368.9	Semi standard non polar	33892256
Protoporphyrin IX,3TMS,isomer #1	C=CC1=C(C)C2=CC3=C(C=C)C(C)=C(C=C4N=C(C=C5[NH]C(=CC1=N2)C(C)=C5CCC(=O)O[Si](C)(C)C)C(CCC(=O)O[Si](C)(C)C)=C4C)N3[Si](C)(C)C	5237.9	Semi standard non polar	33892256
Protoporphyrin IX,3TMS,isomer #1	C=CC1=C(C)C2=CC3=C(C=C)C(C)=C(C=C4N=C(C=C5[NH]C(=CC1=N2)C(C)=C5CCC(=O)O[Si](C)(C)C)C(CCC(=O)O[Si](C)(C)C)=C4C)N3[Si](C)(C)C	4475.5	Standard non polar	33892256
Protoporphyrin IX,3TMS,isomer #1	C=CC1=C(C)C2=CC3=C(C=C)C(C)=C(C=C4N=C(C=C5[NH]C(=CC1=N2)C(C)=C5CCC(=O)O[Si](C)(C)C)C(CCC(=O)O[Si](C)(C)C)=C4C)N3[Si](C)(C)C	6148.1	Standard polar	33892256
Protoporphyrin IX,3TMS,isomer #2	C=CC1=C(C)C2=CC3=C(C=C)C(C)=C(C=C4N=C(C=C5C(CCC(=O)O[Si](C)(C)C)=C(C)C(=CC1=N2)N5[Si](C)(C)C)C(CCC(=O)O[Si](C)(C)C)=C4C)[NH]3	5213.5	Semi standard non polar	33892256
Protoporphyrin IX,3TMS,isomer #2	C=CC1=C(C)C2=CC3=C(C=C)C(C)=C(C=C4N=C(C=C5C(CCC(=O)O[Si](C)(C)C)=C(C)C(=CC1=N2)N5[Si](C)(C)C)C(CCC(=O)O[Si](C)(C)C)=C4C)[NH]3	4461.0	Standard non polar	33892256
Protoporphyrin IX,3TMS,isomer #2	C=CC1=C(C)C2=CC3=C(C=C)C(C)=C(C=C4N=C(C=C5C(CCC(=O)O[Si](C)(C)C)=C(C)C(=CC1=N2)N5[Si](C)(C)C)C(CCC(=O)O[Si](C)(C)C)=C4C)[NH]3	6237.9	Standard polar	33892256
Protoporphyrin IX,3TMS,isomer #3	C=CC1=C(C)C2=CC3=C(C=C)C(C)=C(C=C4N=C(C=C5C(CCC(=O)O[Si](C)(C)C)=C(C)C(=CC1=N2)N5[Si](C)(C)C)C(CCC(=O)O)=C4C)N3[Si](C)(C)C	5282.5	Semi standard non polar	33892256
Protoporphyrin IX,3TMS,isomer #3	C=CC1=C(C)C2=CC3=C(C=C)C(C)=C(C=C4N=C(C=C5C(CCC(=O)O[Si](C)(C)C)=C(C)C(=CC1=N2)N5[Si](C)(C)C)C(CCC(=O)O)=C4C)N3[Si](C)(C)C	4484.5	Standard non polar	33892256
Protoporphyrin IX,3TMS,isomer #3	C=CC1=C(C)C2=CC3=C(C=C)C(C)=C(C=C4N=C(C=C5C(CCC(=O)O[Si](C)(C)C)=C(C)C(=CC1=N2)N5[Si](C)(C)C)C(CCC(=O)O)=C4C)N3[Si](C)(C)C	6111.8	Standard polar	33892256
Protoporphyrin IX,3TMS,isomer #4	C=CC1=C(C)C2=CC3=C(C=C)C(C)=C(C=C4N=C(C=C5C(CCC(=O)O)=C(C)C(=CC1=N2)N5[Si](C)(C)C)C(CCC(=O)O[Si](C)(C)C)=C4C)N3[Si](C)(C)C	5277.2	Semi standard non polar	33892256
Protoporphyrin IX,3TMS,isomer #4	C=CC1=C(C)C2=CC3=C(C=C)C(C)=C(C=C4N=C(C=C5C(CCC(=O)O)=C(C)C(=CC1=N2)N5[Si](C)(C)C)C(CCC(=O)O[Si](C)(C)C)=C4C)N3[Si](C)(C)C	4480.4	Standard non polar	33892256
Protoporphyrin IX,3TMS,isomer #4	C=CC1=C(C)C2=CC3=C(C=C)C(C)=C(C=C4N=C(C=C5C(CCC(=O)O)=C(C)C(=CC1=N2)N5[Si](C)(C)C)C(CCC(=O)O[Si](C)(C)C)=C4C)N3[Si](C)(C)C	6123.2	Standard polar	33892256
Protoporphyrin IX,4TMS,isomer #1	C=CC1=C(C)C2=CC3=C(C=C)C(C)=C(C=C4N=C(C=C5C(CCC(=O)O[Si](C)(C)C)=C(C)C(=CC1=N2)N5[Si](C)(C)C)C(CCC(=O)O[Si](C)(C)C)=C4C)N3[Si](C)(C)C	5182.6	Semi standard non polar	33892256
Protoporphyrin IX,4TMS,isomer #1	C=CC1=C(C)C2=CC3=C(C=C)C(C)=C(C=C4N=C(C=C5C(CCC(=O)O[Si](C)(C)C)=C(C)C(=CC1=N2)N5[Si](C)(C)C)C(CCC(=O)O[Si](C)(C)C)=C4C)N3[Si](C)(C)C	4462.6	Standard non polar	33892256
Protoporphyrin IX,4TMS,isomer #1	C=CC1=C(C)C2=CC3=C(C=C)C(C)=C(C=C4N=C(C=C5C(CCC(=O)O[Si](C)(C)C)=C(C)C(=CC1=N2)N5[Si](C)(C)C)C(CCC(=O)O[Si](C)(C)C)=C4C)N3[Si](C)(C)C	5851.9	Standard polar	33892256
Protoporphyrin IX,1TBDMS,isomer #1	C=CC1=C(C)C2=CC3=C(C=C)C(C)=C(C=C4N=C(C=C5[NH]C(=CC1=N2)C(C)=C5CCC(=O)O[Si](C)(C)C(C)(C)C)C(CCC(=O)O)=C4C)[NH]3	5616.8	Semi standard non polar	33892256
Protoporphyrin IX,1TBDMS,isomer #2	C=CC1=C(C)C2=CC3=C(C=C)C(C)=C(C=C4N=C(C=C5[NH]C(=CC1=N2)C(C)=C5CCC(=O)O)C(CCC(=O)O[Si](C)(C)C(C)(C)C)=C4C)[NH]3	5602.5	Semi standard non polar	33892256
Protoporphyrin IX,1TBDMS,isomer #3	C=CC1=C(C)C2=CC3=C(C=C)C(C)=C(C=C4N=C(C=C5[NH]C(=CC1=N2)C(C)=C5CCC(=O)O)C(CCC(=O)O)=C4C)N3[Si](C)(C)C(C)(C)C	5595.2	Semi standard non polar	33892256
Protoporphyrin IX,1TBDMS,isomer #4	C=CC1=C(C)C2=CC3=C(C=C)C(C)=C(C=C4N=C(C=C5C(CCC(=O)O)=C(C)C(=CC1=N2)N5[Si](C)(C)C(C)(C)C)C(CCC(=O)O)=C4C)[NH]3	5583.3	Semi standard non polar	33892256
Protoporphyrin IX,2TBDMS,isomer #1	C=CC1=C(C)C2=CC3=C(C=C)C(C)=C(C=C4N=C(C=C5[NH]C(=CC1=N2)C(C)=C5CCC(=O)O[Si](C)(C)C(C)(C)C)C(CCC(=O)O[Si](C)(C)C(C)(C)C)=C4C)[NH]3	5648.2	Semi standard non polar	33892256
Protoporphyrin IX,2TBDMS,isomer #2	C=CC1=C(C)C2=CC3=C(C=C)C(C)=C(C=C4N=C(C=C5[NH]C(=CC1=N2)C(C)=C5CCC(=O)O[Si](C)(C)C(C)(C)C)C(CCC(=O)O)=C4C)N3[Si](C)(C)C(C)(C)C	5674.6	Semi standard non polar	33892256
Protoporphyrin IX,2TBDMS,isomer #3	C=CC1=C(C)C2=CC3=C(C=C)C(C)=C(C=C4N=C(C=C5C(CCC(=O)O[Si](C)(C)C(C)(C)C)=C(C)C(=CC1=N2)N5[Si](C)(C)C(C)(C)C)C(CCC(=O)O)=C4C)[NH]3	5664.1	Semi standard non polar	33892256
Protoporphyrin IX,2TBDMS,isomer #4	C=CC1=C(C)C2=CC3=C(C=C)C(C)=C(C=C4N=C(C=C5[NH]C(=CC1=N2)C(C)=C5CCC(=O)O)C(CCC(=O)O[Si](C)(C)C(C)(C)C)=C4C)N3[Si](C)(C)C(C)(C)C	5666.9	Semi standard non polar	33892256
Protoporphyrin IX,2TBDMS,isomer #5	C=CC1=C(C)C2=CC3=C(C=C)C(C)=C(C=C4N=C(C=C5C(CCC(=O)O)=C(C)C(=CC1=N2)N5[Si](C)(C)C(C)(C)C)C(CCC(=O)O[Si](C)(C)C(C)(C)C)=C4C)[NH]3	5660.8	Semi standard non polar	33892256
Protoporphyrin IX,2TBDMS,isomer #6	C=CC1=C(C)C2=CC3=C(C=C)C(C)=C(C=C4N=C(C=C5C(CCC(=O)O)=C(C)C(=CC1=N2)N5[Si](C)(C)C(C)(C)C)C(CCC(=O)O)=C4C)N3[Si](C)(C)C(C)(C)C	5687.2	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 - Protoporphyrin IX GC-MS (Non-derivatized) - 70eV, Positive	splash10-0uxu-1000290000-e22236fe3cca8eed1ecf	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Protoporphyrin IX GC-MS (1 TMS) - 70eV, Positive	splash10-00di-6000094000-b9c12952e100c5144cab	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Protoporphyrin IX GC-MS ("Protoporphyrin IX,1TMS,#1" TMS) - 70eV, Positive	Not Available	2021-10-14	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Protoporphyrin IX GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-10-15	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Protoporphyrin IX GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-10-15	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Protoporphyrin IX GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-10-15	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Protoporphyrin IX GC-MS (TMS_1_4) - 70eV, Positive	Not Available	2021-10-15	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Protoporphyrin IX GC-MS (TMS_2_1) - 70eV, Positive	Not Available	2021-10-15	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Protoporphyrin IX GC-MS (TMS_2_2) - 70eV, Positive	Not Available	2021-10-15	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Protoporphyrin IX GC-MS (TMS_2_3) - 70eV, Positive	Not Available	2021-10-15	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Protoporphyrin IX GC-MS (TMS_2_4) - 70eV, Positive	Not Available	2021-10-15	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Protoporphyrin IX GC-MS (TMS_2_5) - 70eV, Positive	Not Available	2021-10-15	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Protoporphyrin IX GC-MS (TMS_2_6) - 70eV, Positive	Not Available	2021-10-15	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Protoporphyrin IX GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-10-15	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Protoporphyrin IX GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-10-15	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Protoporphyrin IX GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	2021-10-15	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Protoporphyrin IX GC-MS (TBDMS_1_4) - 70eV, Positive	Not Available	2021-10-15	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Protoporphyrin IX GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	2021-10-15	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Protoporphyrin IX GC-MS (TBDMS_2_2) - 70eV, Positive	Not Available	2021-10-15	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Protoporphyrin IX GC-MS (TBDMS_2_3) - 70eV, Positive	Not Available	2021-10-15	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Protoporphyrin IX GC-MS (TBDMS_2_4) - 70eV, Positive	Not Available	2021-10-15	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Protoporphyrin IX GC-MS (TBDMS_2_5) - 70eV, Positive	Not Available	2021-10-15	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Protoporphyrin IX GC-MS (TBDMS_2_6) - 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 - Protoporphyrin IX 10V, Positive-QTOF	splash10-0002-0000090000-5d5be53410134c5719ab	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Protoporphyrin IX 20V, Positive-QTOF	splash10-00kb-1000590000-2d4157b9f73534d95a9c	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Protoporphyrin IX 40V, Positive-QTOF	splash10-0a4l-1000910000-07524a9291a1921dfafc	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Protoporphyrin IX 10V, Negative-QTOF	splash10-03di-0000090000-5df26c1cfb9a0b16a91a	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Protoporphyrin IX 20V, Negative-QTOF	splash10-0296-1000190000-2d4bcb49201fc10adc09	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Protoporphyrin IX 40V, Negative-QTOF	splash10-0a4l-9000230000-064fb944a966d08c06bf	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Protoporphyrin IX 10V, Negative-QTOF	splash10-03di-0000090000-87c1740ecd1a28f4a2d9	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Protoporphyrin IX 20V, Negative-QTOF	splash10-03xu-0000590000-99160b987bb7e62ab362	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Protoporphyrin IX 40V, Negative-QTOF	splash10-00di-0000900000-f2d9118441a9c8c47d79	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Protoporphyrin IX 10V, Positive-QTOF	splash10-03dj-0000090000-d428ac6dc2fc4794cc41	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Protoporphyrin IX 20V, Positive-QTOF	splash10-0j4j-0000090000-2b065966ec57bb97d511	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Protoporphyrin IX 40V, Positive-QTOF	splash10-0uk9-1000970000-b435817e4dc349e65ab3	2021-09-23	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)	2022-08-21	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	2022-08-21	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	2022-08-21	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	2022-08-21	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)	2022-08-21	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	2022-08-21	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)	2022-08-21	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	2022-08-21	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)	2022-08-21	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	2022-08-21	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)	2022-08-21	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	2022-08-21	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)	2022-08-21	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	2022-08-21	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)	2022-08-21	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	2022-08-21	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)	2022-08-21	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	2022-08-21	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)	2022-08-21	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	2022-08-21	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Membrane (predicted from logP)
Mitochondria

Biospecimen Locations

Blood

Tissue Locations

Adipose Tissue
Adrenal Medulla
Bladder
Epidermis
Erythrocyte
Fibroblasts
Intestine
Kidney
Leukocyte
Liver
Platelet
Spleen
Testis
Thyroid Gland

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

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.66 +/- 0.18 uM	Adult (>18 years old)	Female	Normal	Geigy Scientific ...	details
Blood	Detected and Quantified	0.53 +/- 0.13 uM	Adult (>18 years old)	Male	Normal	Geigy Scientific ...	details
Blood	Detected and Quantified	1.09 +/- 0.57 uM	Newborn (0-30 days old)	Both	Normal	Geigy Scientific ...	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0-1.244 uM	Adult (>18 years old)	Male	Protoporphyria, Erythropoietic	13765301	details

Associated Disorders and Diseases

Disease References

Protoporphyria, Erythropoietic
MAGNUS IA, JARRETT A, PRANKERD TA, RIMINGTON C: Erythropoietic protoporphyria. A new porphyria syndrome with solar urticaria due to protoporphyrinaemia. Lancet. 1961 Aug 26;2(7200):448-51. [PubMed:13765301 ]

Associated OMIM IDs

177000 (Protoporphyria, Erythropoietic)

External Links

DrugBank ID

DB02285

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Protoporphyrin_IX

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

15430

Food Biomarker Ontology

Not Available

VMH ID

PPP9

MarkerDB ID

Not Available

Good Scents ID

rw1279251

References

Synthesis Reference

Games, David E.; Jackson, Anthony H.; Jackson, J. Richard; Belcher, Roderick V.; Smith, Sydney G. Biosynthesis of protoporphyrin-IX from coproporphyrinogen-III. Journal of the Chemical Society, Chemical Communications (1976), (6), 187-8.

Material Safety Data Sheet (MSDS)

Not Available

General References

Messmann H, Knuchel R, Baumler W, Holstege A, Scholmerich J: Endoscopic fluorescence detection of dysplasia in patients with Barrett's esophagus, ulcerative colitis, or adenomatous polyps after 5-aminolevulinic acid-induced protoporphyrin IX sensitization. Gastrointest Endosc. 1999 Jan;49(1):97-101. [PubMed:9869731 ]
Stankiewicz A, Lutz W, Krajewska B, Szulc B: [Plasma indicators of iron metabolism in persons occupationally exposed to organic solvents with normal and increased levels of protoporphyrin IX in erythrocytes]. Pol Tyg Lek. 1986 Jul 7;41(27):851-4. [PubMed:3763462 ]
Stankiewicz A: [Erythrocyte protoporphyrin IX in occupational exposure to asbestos]. Med Pr. 1984;35(5):351-4. [PubMed:6530952 ]
Sudworth CD, Stringer MR, Cruse-Sawyer JE, Brown SB: Fluorescence microspectroscopy technique for the study of intracellular protoporphyrin IX dynamics. Appl Spectrosc. 2003 Jun;57(6):682-8. [PubMed:14658702 ]
Kufner G, Schlegel H, Jager R: A spectrophotometric micromethod for determining erythrocyte protoporphyrin-IX in whole blood or erythrocytes. Clin Chem Lab Med. 2005;43(2):183-91. [PubMed:15843214 ]
Stankiewicz A: The concentration of protoporphyrin IX in workers occupationally exposed to lead. Mater Med Pol. 1989 Apr-Jun;21(2):100-2. [PubMed:2488459 ]
Krieg RC, Fickweiler S, Wolfbeis OS, Knuechel R: Cell-type specific protoporphyrin IX metabolism in human bladder cancer in vitro. Photochem Photobiol. 2000 Aug;72(2):226-33. [PubMed:10946577 ]
Bailey GG, Needham LL: Simultaneous quantification of erythrocyte zinc protoporphyrin and protoporphyrin IX by liquid chromatography. Clin Chem. 1986 Dec;32(12):2137-42. [PubMed:3779978 ]
Chisolm J Jr, Brown DH: Micro-scale photofluorometric determination of "free erythrocyte pophyrin" (protoporphyrin IX). Clin Chem. 1975 Oct;21(11):1669-82. [PubMed:1164799 ]
Casas A, Batlle AM, Butler AR, Robertson D, Brown EH, MacRobert A, Riley PA: Comparative effect of ALA derivatives on protoporphyrin IX production in human and rat skin organ cultures. Br J Cancer. 1999 Jul;80(10):1525-32. [PubMed:10408393 ]
Smits T, Robles CA, van Erp PE, van de Kerkhof PC, Gerritsen MJ: Correlation between macroscopic fluorescence and protoporphyrin IX content in psoriasis and actinic keratosis following application of aminolevulinic acid. J Invest Dermatol. 2005 Oct;125(4):833-9. [PubMed:16185285 ]
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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

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

Enzyme Details

3. Ferrochelatase, mitochondrial

General function:: Involved in ferrochelatase activity
Specific function:: Catalyzes the ferrous insertion into protoporphyrin IX.
Gene Name:: FECH
Uniprot ID:: P22830
Molecular weight:: 47861.77

Reactions

Heme + Hydrogen Ion → Protoporphyrin IX + Fe2+	details
Protoporphyrin IX + Fe2+ → Heme + Hydrogen Ion	details

Enzyme Details

4. Ferritin light chain

General function:: Involved in oxidoreductase activity
Specific function:: Stores iron in a soluble, non-toxic, readily available form. Important for iron homeostasis. Iron is taken up in the ferrous form and deposited as ferric hydroxides after oxidation. Also plays a role in delivery of iron to cells. Mediates iron uptake in capsule cells of the developing kidney
Gene Name:: FTL
Uniprot ID:: P02792
Molecular weight:: 20019.5

References

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235 ]

Enzyme Details

5. Ferrochelatase

General function:: Involved in ferrochelatase activity
Specific function:: Catalyzes the ferrous insertion into protoporphyrin IX
Gene Name:: Not Available
Uniprot ID:: Q53FU1
Molecular weight:: 47488.3

Enzyme Details

6. Ferrochelatase

General function:: Involved in ferrochelatase activity
Specific function:: Catalyzes the ferrous insertion into protoporphyrin IX
Gene Name:: Not Available
Uniprot ID:: Q5TZY0
Molecular weight:: 47680.5

Enzyme Details

7. Ferrochelatase

General function:: Involved in ferrochelatase activity
Specific function:: Catalyzes the ferrous insertion into protoporphyrin IX
Gene Name:: DKFZp686P18130
Uniprot ID:: Q7KZA3
Molecular weight:: 47131.9

Showing metabocard for Protoporphyrin IX (HMDB0000241)

MOL for HMDB0000241 (Protoporphyrin IX)

3D MOL for HMDB0000241 (Protoporphyrin IX)

3D SDF for HMDB0000241 (Protoporphyrin IX)

3D-SDF for HMDB0000241 (Protoporphyrin IX)

PDB for HMDB0000241 (Protoporphyrin IX)

3D PDB for HMDB0000241 (Protoporphyrin IX)

SMILES for HMDB0000241 (Protoporphyrin IX)

INCHI for HMDB0000241 (Protoporphyrin IX)

Structure for HMDB0000241 (Protoporphyrin IX)

3D Structure for HMDB0000241 (Protoporphyrin IX)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes

Reactions

Reactions

References