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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

2022-03-07 02:49:09 UTC

HMDB ID

HMDB0001381

Secondary Accession Numbers

HMDB01381

Metabolite Identification

Common Name

Prostaglandin H2

Description

Prostaglandin H2 (PGH2) is the first intermediate in the biosynthesis of all prostaglandins. Prostaglandins are synthesized from arachidonic acid by the enzyme COX-1 and COX-2, which are also called PGH synthase 1 and 2. These enzymes generate a reactive intermediate PGH2 which has a reasonably long half-life (90-100 s) but is highly lipophilic. PGH2 is converted into the biologically active prostaglandins by prostaglandin isomerases, yielding PGE2, PGD2, and PGF2, or by thromboxane synthase to make TXA2 or by prostacyclin synthase to make PGI2. Most nonsteroidal anti-inflammatory drugs such as aspirin and indomethacin inhibit both PGH synthase 1 and 2. A key feature for eicosanoid transcellular biosynthesis is the export of PGH2 or LTA4 from the donor cell as well as the uptake of these reactive intermediates by the acceptor cell. Very little is known about either process despite the demonstrated importance of both events. In cells, PGH2 rearranges nonenzymatically to LGs even in the presence of enzymes that use PGH2 as a substrate. When platelets form thromboxane A2 (TXA2) from endogenous arachidonic acid (AA), PGH2 reaches concentrations very similar to those of TXA2 and high enough to produce strong platelet activation. Therefore, platelet activation by TXA2 appears to go along with an activation by PGH2. The agonism of PGH2 is limited by the formation of inhibitory prostaglandins, especially PGD2 at higher concentrations. That is why thromboxane synthase inhibitors in PRP and at a physiological HSA concentration do not augment platelet activation (PMID: 2798452 , 15650407 , 16968946 ). Prostaglandins are eicosanoids. The eicosanoids consist of the prostaglandins (PGs), thromboxanes (TXs), leukotrienes (LTs), and lipoxins (LXs). The PGs and TXs are collectively identified as prostanoids. Prostaglandins were originally shown to be synthesized in the prostate gland, thromboxanes from platelets (thrombocytes), and leukotrienes from leukocytes, hence the derivation of their names. All mammalian cells except erythrocytes synthesize eicosanoids. These molecules are extremely potent and are able to cause profound physiological effects at very dilute concentrations. All eicosanoids function locally at the site of synthesis through receptor-mediated G-protein linked signalling pathways.

Structure

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

HMDB0001381
     RDKit          3D
Prostaglandin H2
 57 58  0  0  0  0  0  0  0  0999 V2000
    5.7624    1.3467    2.6402 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9910    0.0386    2.4679 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6159    0.3138    1.9624 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5627    1.0111    0.6399 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2177    0.2575   -0.4768 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5326   -1.0646   -0.6419 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.1025   -1.8145   -1.6733 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0851   -0.9672   -0.9184 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5367    0.0108   -1.6191 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1276    0.1948   -1.9449 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1467    0.3358   -3.4199 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6351   -1.0858   -3.7543 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7362   -1.0061   -2.6770 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.2763    0.2172   -2.9788 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3944    0.9835   -3.5215 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8387   -0.8118   -1.4561 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7033   -0.3022   -0.2963 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5131    0.8659   -0.6424 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8247    0.9479   -0.6127 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6648   -0.1813   -0.2090 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5147    0.1437    1.0099 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6521    0.5051    2.1943 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5297    0.8094    3.3431 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7725    0.7354    3.2015 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0293    1.1744    4.5744 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4553    1.3027    3.5058 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0691    2.1913    2.8326 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4036    1.5402    1.7409 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8960   -0.3847    3.4906 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5554   -0.6919    1.8747 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1116    0.9787    2.7027 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0409   -0.6338    1.9729 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9885    2.0322    0.7121 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4928    1.1437    0.3769 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2932    0.0349   -0.2715 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2229    0.8767   -1.3945 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6687   -1.6584    0.2833 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0097   -1.2634   -2.4925 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4409   -1.7275   -0.5322 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2781    0.7524   -1.9793 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1563    1.2017   -1.5091 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6244    0.7052   -4.0398 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1085   -1.8415   -3.5209 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0860   -1.1360   -4.7455 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3780   -1.8525   -2.6466 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4566   -1.7753   -1.1271 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9362    0.0629    0.4598 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2096   -1.1335    0.1910 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9884    1.7809   -0.9595 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3208    1.8829   -0.8959 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1587   -1.1506   -0.0936 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4006   -0.3600   -1.0560 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1280   -0.7207    1.3062 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1661    1.0086    0.8033 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9806   -0.3446    2.4766 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0201    1.3968    1.9290 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5763    1.0288    5.4145 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 13 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  2  0
 23 25  1  0
 16 10  1  0
 15 11  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  2 29  1  0
  2 30  1  0
  3 31  1  0
  3 32  1  0
  4 33  1  0
  4 34  1  0
  5 35  1  0
  5 36  1  0
  6 37  1  1
  7 38  1  0
  8 39  1  0
  9 40  1  0
 10 41  1  1
 11 42  1  6
 12 43  1  0
 12 44  1  0
 13 45  1  1
 16 46  1  1
 17 47  1  0
 17 48  1  0
 18 49  1  0
 19 50  1  0
 20 51  1  0
 20 52  1  0
 21 53  1  0
 21 54  1  0
 22 55  1  0
 22 56  1  0
 25 57  1  0
M  END

  Mrv1652305171817272D          

 25 26  0  0  0  0            999 V2000
10011.108510013.8190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10011.823710013.4057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10012.647810013.4057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10013.361710013.8190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10014.075810013.4057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10014.789810013.8190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10015.503810013.4057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10016.217810013.8190    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10015.503810012.5823    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10011.108510012.1701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10011.823710012.5823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10012.536810012.1701    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10013.251210012.5823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10013.965310012.1701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10014.679310012.5823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10015.393310012.1701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10016.107310012.5823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10012.536810011.3456    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10009.953610012.9943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10009.680810013.8203    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10008.965410013.4073    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10008.965410012.5812    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10009.680810012.1683    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10010.396210012.5812    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10010.396210013.4073    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  2  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 18  1  6  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 20 25  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 20 21  1  0  0  0  0
 22 23  1  0  0  0  0
 21 22  1  0  0  0  0
 24 10  1  1  0  0  0
 25  1  1  6  0  0  0
 20 19  1  1  0  0  0
 23 19  1  1  0  0  0
M  END
> <DATABASE_ID>
HMDB0001381

> <DATABASE_NAME>
hmdb

> <SMILES>
CCCCC[C@H](O)\C=C\[C@H]1[C@H]2C[C@H](OO2)[C@@H]1C\C=C/CCCC(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C20H32O5/c1-2-3-6-9-15(21)12-13-17-16(18-14-19(17)25-24-18)10-7-4-5-8-11-20(22)23/h4,7,12-13,15-19,21H,2-3,5-6,8-11,14H2,1H3,(H,22,23)/b7-4-,13-12+/t15-,16+,17+,18-,19+/m0/s1

> <INCHI_KEY>
YIBNHAJFJUQSRA-YNNPMVKQSA-N

> <FORMULA>
C20H32O5

> <MOLECULAR_WEIGHT>
352.4651

> <EXACT_MASS>
352.224974134

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
57

> <JCHEM_AVERAGE_POLARIZABILITY>
39.904322068518134

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(5Z)-7-[(1R,4S,5R,6R)-6-[(1E,3S)-3-hydroxyoct-1-en-1-yl]-2,3-dioxabicyclo[2.2.1]heptan-5-yl]hept-5-enoic acid

> <ALOGPS_LOGP>
4.27

> <JCHEM_LOGP>
3.956927585999999

> <ALOGPS_LOGS>
-4.02

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
17.680578207201535

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.355294049144599

> <JCHEM_PKA_STRONGEST_BASIC>
-1.6260430885771613

> <JCHEM_POLAR_SURFACE_AREA>
75.99000000000001

> <JCHEM_REFRACTIVITY>
98.0419

> <JCHEM_ROTATABLE_BOND_COUNT>
12

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.37e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
prostaglandin H2

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0001381
     RDKit          3D
Prostaglandin H2
 57 58  0  0  0  0  0  0  0  0999 V2000
    5.7624    1.3467    2.6402 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9910    0.0386    2.4679 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6159    0.3138    1.9624 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5627    1.0111    0.6399 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2177    0.2575   -0.4768 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5326   -1.0646   -0.6419 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.1025   -1.8145   -1.6733 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0851   -0.9672   -0.9184 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5367    0.0108   -1.6191 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1276    0.1948   -1.9449 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1467    0.3358   -3.4199 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6351   -1.0858   -3.7543 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7362   -1.0061   -2.6770 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.2763    0.2172   -2.9788 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3944    0.9835   -3.5215 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8387   -0.8118   -1.4561 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7033   -0.3022   -0.2963 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5131    0.8659   -0.6424 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8247    0.9479   -0.6127 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6648   -0.1813   -0.2090 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5147    0.1437    1.0099 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6521    0.5051    2.1943 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5297    0.8094    3.3431 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7725    0.7354    3.2015 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0293    1.1744    4.5744 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4553    1.3027    3.5058 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0691    2.1913    2.8326 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4036    1.5402    1.7409 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8960   -0.3847    3.4906 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5554   -0.6919    1.8747 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1116    0.9787    2.7027 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0409   -0.6338    1.9729 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9885    2.0322    0.7121 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4928    1.1437    0.3769 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2932    0.0349   -0.2715 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2229    0.8767   -1.3945 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6687   -1.6584    0.2833 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0097   -1.2634   -2.4925 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4409   -1.7275   -0.5322 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2781    0.7524   -1.9793 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1563    1.2017   -1.5091 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6244    0.7052   -4.0398 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1085   -1.8415   -3.5209 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0860   -1.1360   -4.7455 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3780   -1.8525   -2.6466 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4566   -1.7753   -1.1271 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9362    0.0629    0.4598 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2096   -1.1335    0.1910 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9884    1.7809   -0.9595 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3208    1.8829   -0.8959 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1587   -1.1506   -0.0936 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4006   -0.3600   -1.0560 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1280   -0.7207    1.3062 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1661    1.0086    0.8033 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9806   -0.3446    2.4766 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0201    1.3968    1.9290 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5763    1.0288    5.4145 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 13 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  2  0
 23 25  1  0
 16 10  1  0
 15 11  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  2 29  1  0
  2 30  1  0
  3 31  1  0
  3 32  1  0
  4 33  1  0
  4 34  1  0
  5 35  1  0
  5 36  1  0
  6 37  1  1
  7 38  1  0
  8 39  1  0
  9 40  1  0
 10 41  1  1
 11 42  1  6
 12 43  1  0
 12 44  1  0
 13 45  1  1
 16 46  1  1
 17 47  1  0
 17 48  1  0
 18 49  1  0
 19 50  1  0
 20 51  1  0
 20 52  1  0
 21 53  1  0
 21 54  1  0
 22 55  1  0
 22 56  1  0
 25 57  1  0
M  END

HEADER    PROTEIN                                 17-MAY-18   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-MAY-18         0                                  
HETATM    1  C   UNK     0    8687.4038692.462   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8688.7388691.691   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8690.2768691.691   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    8691.6088692.462   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0    8692.9418691.691   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    8694.2748692.462   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    8695.6078691.691   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0    8696.9408692.462   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0    8695.6078690.154   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0    8687.4038689.384   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8688.7388690.154   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8690.0698689.384   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8691.4028690.154   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8692.7358689.384   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8694.0688690.154   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8695.4018689.384   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8696.7348690.154   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0    8690.0698687.845   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0    8685.2478690.923   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0    8684.7388692.465   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0    8683.4028691.694   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0    8683.4028690.152   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0    8684.7388689.381   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0    8686.0738690.152   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0    8686.0738691.694   0.000  0.00  0.00           C+0
CONECT    1    2   25                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7                                                            
CONECT   10   11   24                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   18                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16                                                            
CONECT   18   12                                                            
CONECT   19   20   23                                                       
CONECT   20   25   21   19                                                  
CONECT   21   20   22                                                       
CONECT   22   23   21                                                       
CONECT   23   24   22   19                                                  
CONECT   24   23   25   10                                                  
CONECT   25   20   24    1                                                  
MASTER        0    0    0    0    0    0    0    0   25    0   52    0
END

COMPND    HMDB0001381
HETATM    1  C1  UNL     1       5.762   1.347   2.640  1.00  0.00           C  
HETATM    2  C2  UNL     1       4.991   0.039   2.468  1.00  0.00           C  
HETATM    3  C3  UNL     1       3.616   0.314   1.962  1.00  0.00           C  
HETATM    4  C4  UNL     1       3.563   1.011   0.640  1.00  0.00           C  
HETATM    5  C5  UNL     1       4.218   0.258  -0.477  1.00  0.00           C  
HETATM    6  C6  UNL     1       3.533  -1.065  -0.642  1.00  0.00           C  
HETATM    7  O1  UNL     1       4.103  -1.814  -1.673  1.00  0.00           O  
HETATM    8  C7  UNL     1       2.085  -0.967  -0.918  1.00  0.00           C  
HETATM    9  C8  UNL     1       1.537   0.011  -1.619  1.00  0.00           C  
HETATM   10  C9  UNL     1       0.128   0.195  -1.945  1.00  0.00           C  
HETATM   11  C10 UNL     1      -0.147   0.336  -3.420  1.00  0.00           C  
HETATM   12  C11 UNL     1      -0.635  -1.086  -3.754  1.00  0.00           C  
HETATM   13  C12 UNL     1      -1.736  -1.006  -2.677  1.00  0.00           C  
HETATM   14  O2  UNL     1      -2.276   0.217  -2.979  1.00  0.00           O  
HETATM   15  O3  UNL     1      -1.394   0.983  -3.522  1.00  0.00           O  
HETATM   16  C13 UNL     1      -0.839  -0.812  -1.456  1.00  0.00           C  
HETATM   17  C14 UNL     1      -1.703  -0.302  -0.296  1.00  0.00           C  
HETATM   18  C15 UNL     1      -2.513   0.866  -0.642  1.00  0.00           C  
HETATM   19  C16 UNL     1      -3.825   0.948  -0.613  1.00  0.00           C  
HETATM   20  C17 UNL     1      -4.665  -0.181  -0.209  1.00  0.00           C  
HETATM   21  C18 UNL     1      -5.515   0.144   1.010  1.00  0.00           C  
HETATM   22  C19 UNL     1      -4.652   0.505   2.194  1.00  0.00           C  
HETATM   23  C20 UNL     1      -5.530   0.809   3.343  1.00  0.00           C  
HETATM   24  O4  UNL     1      -6.772   0.735   3.202  1.00  0.00           O  
HETATM   25  O5  UNL     1      -5.029   1.174   4.574  1.00  0.00           O  
HETATM   26  H1  UNL     1       6.455   1.303   3.506  1.00  0.00           H  
HETATM   27  H2  UNL     1       5.069   2.191   2.833  1.00  0.00           H  
HETATM   28  H3  UNL     1       6.404   1.540   1.741  1.00  0.00           H  
HETATM   29  H4  UNL     1       4.896  -0.385   3.491  1.00  0.00           H  
HETATM   30  H5  UNL     1       5.555  -0.692   1.875  1.00  0.00           H  
HETATM   31  H6  UNL     1       3.112   0.979   2.703  1.00  0.00           H  
HETATM   32  H7  UNL     1       3.041  -0.634   1.973  1.00  0.00           H  
HETATM   33  H8  UNL     1       3.989   2.032   0.712  1.00  0.00           H  
HETATM   34  H9  UNL     1       2.493   1.144   0.377  1.00  0.00           H  
HETATM   35  H10 UNL     1       5.293   0.035  -0.271  1.00  0.00           H  
HETATM   36  H11 UNL     1       4.223   0.877  -1.394  1.00  0.00           H  
HETATM   37  H12 UNL     1       3.669  -1.658   0.283  1.00  0.00           H  
HETATM   38  H13 UNL     1       4.010  -1.263  -2.493  1.00  0.00           H  
HETATM   39  H14 UNL     1       1.441  -1.727  -0.532  1.00  0.00           H  
HETATM   40  H15 UNL     1       2.278   0.752  -1.979  1.00  0.00           H  
HETATM   41  H16 UNL     1      -0.156   1.202  -1.509  1.00  0.00           H  
HETATM   42  H17 UNL     1       0.624   0.705  -4.040  1.00  0.00           H  
HETATM   43  H18 UNL     1       0.109  -1.842  -3.521  1.00  0.00           H  
HETATM   44  H19 UNL     1      -1.086  -1.136  -4.745  1.00  0.00           H  
HETATM   45  H20 UNL     1      -2.378  -1.853  -2.647  1.00  0.00           H  
HETATM   46  H21 UNL     1      -0.457  -1.775  -1.127  1.00  0.00           H  
HETATM   47  H22 UNL     1      -0.936   0.063   0.460  1.00  0.00           H  
HETATM   48  H23 UNL     1      -2.210  -1.134   0.191  1.00  0.00           H  
HETATM   49  H24 UNL     1      -1.988   1.781  -0.959  1.00  0.00           H  
HETATM   50  H25 UNL     1      -4.321   1.883  -0.896  1.00  0.00           H  
HETATM   51  H26 UNL     1      -4.159  -1.151  -0.094  1.00  0.00           H  
HETATM   52  H27 UNL     1      -5.401  -0.360  -1.056  1.00  0.00           H  
HETATM   53  H28 UNL     1      -6.128  -0.721   1.306  1.00  0.00           H  
HETATM   54  H29 UNL     1      -6.166   1.009   0.803  1.00  0.00           H  
HETATM   55  H30 UNL     1      -3.981  -0.345   2.477  1.00  0.00           H  
HETATM   56  H31 UNL     1      -4.020   1.397   1.929  1.00  0.00           H  
HETATM   57  H32 UNL     1      -5.576   1.029   5.414  1.00  0.00           H  
CONECT    1    2   26   27   28
CONECT    2    3   29   30
CONECT    3    4   31   32
CONECT    4    5   33   34
CONECT    5    6   35   36
CONECT    6    7    8   37
CONECT    7   38
CONECT    8    9    9   39
CONECT    9   10   40
CONECT   10   11   16   41
CONECT   11   12   15   42
CONECT   12   13   43   44
CONECT   13   14   16   45
CONECT   14   15
CONECT   16   17   46
CONECT   17   18   47   48
CONECT   18   19   19   49
CONECT   19   20   50
CONECT   20   21   51   52
CONECT   21   22   53   54
CONECT   22   23   55   56
CONECT   23   24   24   25
CONECT   25   57
END

HMDB0001381
     RDKit          3D
Prostaglandin H2
 57 58  0  0  0  0  0  0  0  0999 V2000
    5.7624    1.3467    2.6402 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9910    0.0386    2.4679 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6159    0.3138    1.9624 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5627    1.0111    0.6399 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2177    0.2575   -0.4768 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5326   -1.0646   -0.6419 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.1025   -1.8145   -1.6733 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0851   -0.9672   -0.9184 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5367    0.0108   -1.6191 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1276    0.1948   -1.9449 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1467    0.3358   -3.4199 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6351   -1.0858   -3.7543 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7362   -1.0061   -2.6770 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.2763    0.2172   -2.9788 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3944    0.9835   -3.5215 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8387   -0.8118   -1.4561 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7033   -0.3022   -0.2963 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5131    0.8659   -0.6424 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8247    0.9479   -0.6127 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6648   -0.1813   -0.2090 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5147    0.1437    1.0099 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6521    0.5051    2.1943 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5297    0.8094    3.3431 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7725    0.7354    3.2015 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0293    1.1744    4.5744 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4553    1.3027    3.5058 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0691    2.1913    2.8326 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4036    1.5402    1.7409 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8960   -0.3847    3.4906 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5554   -0.6919    1.8747 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1116    0.9787    2.7027 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0409   -0.6338    1.9729 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9885    2.0322    0.7121 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4928    1.1437    0.3769 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2932    0.0349   -0.2715 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2229    0.8767   -1.3945 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6687   -1.6584    0.2833 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0097   -1.2634   -2.4925 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4409   -1.7275   -0.5322 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2781    0.7524   -1.9793 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1563    1.2017   -1.5091 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6244    0.7052   -4.0398 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1085   -1.8415   -3.5209 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0860   -1.1360   -4.7455 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3780   -1.8525   -2.6466 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4566   -1.7753   -1.1271 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9362    0.0629    0.4598 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2096   -1.1335    0.1910 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9884    1.7809   -0.9595 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3208    1.8829   -0.8959 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1587   -1.1506   -0.0936 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4006   -0.3600   -1.0560 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1280   -0.7207    1.3062 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1661    1.0086    0.8033 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9806   -0.3446    2.4766 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0201    1.3968    1.9290 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5763    1.0288    5.4145 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 13 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  2  0
 23 25  1  0
 16 10  1  0
 15 11  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  2 29  1  0
  2 30  1  0
  3 31  1  0
  3 32  1  0
  4 33  1  0
  4 34  1  0
  5 35  1  0
  5 36  1  0
  6 37  1  1
  7 38  1  0
  8 39  1  0
  9 40  1  0
 10 41  1  1
 11 42  1  6
 12 43  1  0
 12 44  1  0
 13 45  1  1
 16 46  1  1
 17 47  1  0
 17 48  1  0
 18 49  1  0
 19 50  1  0
 20 51  1  0
 20 52  1  0
 21 53  1  0
 21 54  1  0
 22 55  1  0
 22 56  1  0
 25 57  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(5Z,13E)-(15S)-9alpha,11alpha-Epidioxy-15-hydroxyprosta-5,13-dienoate	ChEBI
(5Z,13E,15S)-9alpha,11alpha-Epidioxy-15-hydroxyprosta-5,13-dienoate	ChEBI
(5Z,9alpha,11alpha,13E,15S)-9,11-Epidioxy-15-hydroxyprosta-5,13-dien-1-Oic acid	ChEBI
9,11-Epoxymethano-PGH2	ChEBI
PGH2	ChEBI
(5Z,9alpha,11alpha,13E,15S)-9,11-Epidioxy-15-hydroxy-prosta-5,13-dienoate	Kegg
(5Z,13E)-(15S)-9a,11a-Epidioxy-15-hydroxyprosta-5,13-dienoate	Generator
(5Z,13E)-(15S)-9a,11a-Epidioxy-15-hydroxyprosta-5,13-dienoic acid	Generator
(5Z,13E)-(15S)-9alpha,11alpha-Epidioxy-15-hydroxyprosta-5,13-dienoic acid	Generator
(5Z,13E)-(15S)-9Α,11α-epidioxy-15-hydroxyprosta-5,13-dienoate	Generator
(5Z,13E)-(15S)-9Α,11α-epidioxy-15-hydroxyprosta-5,13-dienoic acid	Generator
(5Z,13E,15S)-9a,11a-Epidioxy-15-hydroxyprosta-5,13-dienoate	Generator
(5Z,13E,15S)-9a,11a-Epidioxy-15-hydroxyprosta-5,13-dienoic acid	Generator
(5Z,13E,15S)-9alpha,11alpha-Epidioxy-15-hydroxyprosta-5,13-dienoic acid	Generator
(5Z,13E,15S)-9Α,11α-epidioxy-15-hydroxyprosta-5,13-dienoate	Generator
(5Z,13E,15S)-9Α,11α-epidioxy-15-hydroxyprosta-5,13-dienoic acid	Generator
(5Z,9a,11a,13E,15S)-9,11-Epidioxy-15-hydroxyprosta-5,13-dien-1-Oate	Generator
(5Z,9a,11a,13E,15S)-9,11-Epidioxy-15-hydroxyprosta-5,13-dien-1-Oic acid	Generator
(5Z,9alpha,11alpha,13E,15S)-9,11-Epidioxy-15-hydroxyprosta-5,13-dien-1-Oate	Generator
(5Z,9Α,11α,13E,15S)-9,11-epidioxy-15-hydroxyprosta-5,13-dien-1-Oate	Generator
(5Z,9Α,11α,13E,15S)-9,11-epidioxy-15-hydroxyprosta-5,13-dien-1-Oic acid	Generator
(5Z,9a,11a,13E,15S)-9,11-Epidioxy-15-hydroxy-prosta-5,13-dienoate	Generator
(5Z,9a,11a,13E,15S)-9,11-Epidioxy-15-hydroxy-prosta-5,13-dienoic acid	Generator
(5Z,9alpha,11alpha,13E,15S)-9,11-Epidioxy-15-hydroxy-prosta-5,13-dienoic acid	Generator
(5Z,9Α,11α,13E,15S)-9,11-epidioxy-15-hydroxy-prosta-5,13-dienoate	Generator
(5Z,9Α,11α,13E,15S)-9,11-epidioxy-15-hydroxy-prosta-5,13-dienoic acid	Generator
(15S)Hydroxy-9alpha,11alpha-(epoxymethano)prosta-5,13-dienoate	HMDB
(15S)Hydroxy-9alpha,11alpha-(epoxymethano)prosta-5,13-dienoic acid	HMDB
(5Z)-7-{(1R,4S,5R,6R)-6-[(1E,3S)-3-hydroxyoct-1-en-1-yl]-2,3-dioxabicyclo[2.2.1]hept-5-yl}hept-5-enoate	HMDB
(5Z)-7-{(1R,4S,5R,6R)-6-[(1E,3S)-3-hydroxyoct-1-en-1-yl]-2,3-dioxabicyclo[2.2.1]hept-5-yl}hept-5-enoic acid	HMDB
(5Z,13E)-(15S)-9,11-Epidioxy-15-hydroxyprosta-5,13-dienoate	HMDB
(5Z,13E)-(15S)-9,11-Epidioxy-15-hydroxyprosta-5,13-dienoic acid	HMDB
(5Z,13E)-(15S)-9-alpha,11-alpha-Epidioxy-15-hydroxyprosta-5,13-dienoate	HMDB
(5Z,13E)-(15S)-9-alpha,11-alpha-Epidioxy-15-hydroxyprosta-5,13-dienoic acid	HMDB
(5Z,13E,15S)-9-alpha,11-alpha-Epidioxy-15-hydroxyprosta-5,13-dienoate	HMDB
(5Z,13E,15S)-9-alpha,11-alpha-Epidioxy-15-hydroxyprosta-5,13-dienoic acid	HMDB
(5Z,9alpha,11alpha,13E,15S)-9,11-Epidioxy-15-hydroxy-prosta-5,13-dien-1-Oate	HMDB
(5Z,9alpha,11alpha,13E,15S)-9,11-Epidioxy-15-hydroxy-prosta-5,13-dien-1-Oic acid	HMDB
15-Hydroxy-9alpha,11alpha-peroxidoprosta-5,13-dienoate	HMDB
15-Hydroxy-9alpha,11alpha-peroxidoprosta-5,13-dienoic acid	HMDB
9S,11R-Epidioxy-15S-hydroxy-5Z,13E-prostadienoate	HMDB
9S,11R-Epidioxy-15S-hydroxy-5Z,13E-prostadienoic acid	HMDB
Endoperoxide H2	HMDB
Prostaglandin R2	HMDB
Prostaglandin-H2	HMDB
PGH(2)	HMDB

Chemical Formula

C₂₀H₃₂O₅

Average Molecular Weight

352.4651

Monoisotopic Molecular Weight

352.224974134

IUPAC Name

(5Z)-7-[(1R,4S,5R,6R)-6-[(1E,3S)-3-hydroxyoct-1-en-1-yl]-2,3-dioxabicyclo[2.2.1]heptan-5-yl]hept-5-enoic acid

Traditional Name

prostaglandin H2

CAS Registry Number

42935-17-1

SMILES

CCCCC[C@H](O)\C=C\[C@H]1[C@H]2C[C@H](OO2)[C@@H]1C\C=C/CCCC(O)=O

InChI Identifier

InChI=1S/C20H32O5/c1-2-3-6-9-15(21)12-13-17-16(18-14-19(17)25-24-18)10-7-4-5-8-11-20(22)23/h4,7,12-13,15-19,21H,2-3,5-6,8-11,14H2,1H3,(H,22,23)/b7-4-,13-12+/t15-,16+,17+,18-,19+/m0/s1

InChI Key

YIBNHAJFJUQSRA-YNNPMVKQSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as prostaglandins and related compounds. These are unsaturated carboxylic acids consisting of a 20 carbon skeleton that also contains a five member ring, and are based upon the fatty acid arachidonic acid.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Eicosanoids

Direct Parent

Prostaglandins and related compounds

Alternative Parents

Substituents

Prostaglandin skeleton
Long-chain fatty acid
Heterocyclic fatty acid
Hydroxy fatty acid
Ortho-dioxane
Fatty acid
Unsaturated fatty acid
Ortho-dioxolane
Dialkyl peroxide
Secondary alcohol
Carboxylic acid derivative
Carboxylic acid
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Organic oxide
Organic oxygen compound
Hydrocarbon derivative
Alcohol
Carbonyl group
Organooxygen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

prostaglandins H (CHEBI:15554 )
oxylipin (CHEBI:15554 )
Prostaglandins (C00427 )
Prostaglandins (LMFA03010010 )

Ontology

Not Available

Platelet (HMDB: HMDB0001381)

Cellular substructure

Organelle

Endoplasmic reticulum (HMDB: HMDB0001381)

Source

Exogenous

Exogenous (HMDB: HMDB0001381)

Endogenous

Endogenous (HMDB: HMDB0001381)

Process

Naturally occurring process

Biological process

Biochemical pathway

Disease pathway

Leukotriene C4 Synthesis Deficiency (PathBank: SMP0120510)

Metabolic pathway

Arachidonic Acid Metabolism (PathBank: SMP0087315)

Drug action pathway

Piroxicam Action Pathway (PathBank: SMP0000077)
Acetylsalicylic Acid Action Pathway (PathBank: SMP0000083)
Etodolac Action Pathway (PathBank: SMP0000084)
Ketoprofen Action Pathway (PathBank: SMP0000085)
Ibuprofen Action Pathway (PathBank: SMP0000086)
Rofecoxib Action Pathway (PathBank: SMP0000087)
Diclofenac Action Pathway (PathBank: SMP0000093)
Sulindac Action Pathway (PathBank: SMP0000094)
Celecoxib Action Pathway (PathBank: SMP0000096)
Ketorolac Action Pathway (PathBank: SMP0000098)
Suprofen Action Pathway (PathBank: SMP0000101)
Bromfenac Action Pathway (PathBank: SMP0000102)
Indomethacin Action Pathway (PathBank: SMP0000104)
Mefenamic Acid Action Pathway (PathBank: SMP0000109)
Oxaprozin Action Pathway (PathBank: SMP0000113)
Nabumetone Action Pathway (PathBank: SMP0000114)
Naproxen Action Pathway (PathBank: SMP0000120)
Diflunisal Action Pathway (PathBank: SMP0000289)
Meloxicam Action Pathway (PathBank: SMP0000106)
Valdecoxib Action Pathway (PathBank: SMP0000116)
Antipyrine Action Pathway (PathBank: SMP0000692)
Antrafenine Action Pathway (PathBank: SMP0000693)
Carprofen Action Pathway (PathBank: SMP0000694)
Etoricoxib Action Pathway (PathBank: SMP0000695)
Fenoprofen Action Pathway (PathBank: SMP0000696)
Flurbiprofen Action Pathway (PathBank: SMP0000697)
Magnesium salicylate Action Pathway (PathBank: SMP0000698)
Lumiracoxib Action Pathway (PathBank: SMP0000699)
Lornoxicam Action Pathway (PathBank: SMP0000700)
Phenylbutazone Action Pathway (PathBank: SMP0000701)
Nepafenac Action Pathway (PathBank: SMP0000702)
Trisalicylate-choline Action Pathway (PathBank: SMP0000703)
Tolmetin Action Pathway (PathBank: SMP0000704)
Tiaprofenic Acid Action Pathway (PathBank: SMP0000705)
Tenoxicam Action Pathway (PathBank: SMP0000706)
Salsalate Action Pathway (PathBank: SMP0000707)
Salicylate-sodium Action Pathway (PathBank: SMP0000708)
Salicylic Acid Action Pathway (PathBank: SMP0000709)
Acetaminophen Action Pathway (PathBank: SMP0000710)

Role

Not Available

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	0.034 g/L	ALOGPS
logP	4.27	ALOGPS
logP	3.96	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	4.36	ChemAxon
pKa (Strongest Basic)	-1.6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	75.99 Å²	ChemAxon
Rotatable Bond Count	12	ChemAxon
Refractivity	98.04 m³·mol⁻¹	ChemAxon
Polarizability	39.9 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	186.185	31661259
DarkChem	[M-H]-	191.411	31661259
AllCCS	[M+H]+	192.713	32859911
AllCCS	[M-H]-	192.593	32859911
DeepCCS	[M+H]+	195.173	30932474
DeepCCS	[M-H]-	192.778	30932474
DeepCCS	[M-2H]-	226.099	30932474
DeepCCS	[M+Na]+	201.029	30932474
AllCCS	[M+H]+	192.7	32859911
AllCCS	[M+H-H2O]+	190.0	32859911
AllCCS	[M+NH4]+	195.2	32859911
AllCCS	[M+Na]+	195.9	32859911
AllCCS	[M-H]-	192.6	32859911
AllCCS	[M+Na-2H]-	193.9	32859911
AllCCS	[M+HCOO]-	195.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Prostaglandin H2	CCCCC[C@H](O)\C=C\[C@H]1[C@H]2C[C@H](OO2)[C@@H]1C\C=C/CCCC(O)=O	4176.5	Standard polar	33892256
Prostaglandin H2	CCCCC[C@H](O)\C=C\[C@H]1[C@H]2C[C@H](OO2)[C@@H]1C\C=C/CCCC(O)=O	2546.5	Standard non polar	33892256
Prostaglandin H2	CCCCC[C@H](O)\C=C\[C@H]1[C@H]2C[C@H](OO2)[C@@H]1C\C=C/CCCC(O)=O	2701.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Prostaglandin H2,1TMS,isomer #1	CCCCC[C@@H](/C=C/[C@H]1[C@H]2C[C@H](OO2)[C@@H]1C/C=C\CCCC(=O)O)O[Si](C)(C)C	2698.8	Semi standard non polar	33892256
Prostaglandin H2,1TMS,isomer #2	CCCCC[C@H](O)/C=C/[C@H]1[C@H]2C[C@H](OO2)[C@@H]1C/C=C\CCCC(=O)O[Si](C)(C)C	2661.0	Semi standard non polar	33892256
Prostaglandin H2,2TMS,isomer #1	CCCCC[C@@H](/C=C/[C@H]1[C@H]2C[C@H](OO2)[C@@H]1C/C=C\CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C	2703.5	Semi standard non polar	33892256
Prostaglandin H2,1TBDMS,isomer #1	CCCCC[C@@H](/C=C/[C@H]1[C@H]2C[C@H](OO2)[C@@H]1C/C=C\CCCC(=O)O)O[Si](C)(C)C(C)(C)C	2890.3	Semi standard non polar	33892256
Prostaglandin H2,1TBDMS,isomer #2	CCCCC[C@H](O)/C=C/[C@H]1[C@H]2C[C@H](OO2)[C@@H]1C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C	2882.3	Semi standard non polar	33892256
Prostaglandin H2,2TBDMS,isomer #1	CCCCC[C@@H](/C=C/[C@H]1[C@H]2C[C@H](OO2)[C@@H]1C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3145.7	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 - Prostaglandin H2 GC-MS (Non-derivatized) - 70eV, Positive	splash10-05d3-5192000000-448e0e493622387c9600	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Prostaglandin H2 GC-MS (2 TMS) - 70eV, Positive	splash10-00gr-9221300000-2098865f850184449832	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Prostaglandin H2 GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Prostaglandin H2 GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	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 - Prostaglandin H2 10V, Positive-QTOF	splash10-000i-0019000000-f1f4732bb2fcf1ecdd31	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Prostaglandin H2 20V, Positive-QTOF	splash10-00kr-4298000000-8f02063e16efefaecab3	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Prostaglandin H2 40V, Positive-QTOF	splash10-05tu-9300000000-e3cb6f0175b4d6d56475	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Prostaglandin H2 10V, Negative-QTOF	splash10-0udi-0009000000-661131f879ff507a5adf	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Prostaglandin H2 20V, Negative-QTOF	splash10-0kai-1049000000-c49ffddba6a8b323d42f	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Prostaglandin H2 40V, Negative-QTOF	splash10-0a4i-9332000000-145fc48bf43661f2584f	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Prostaglandin H2 10V, Positive-QTOF	splash10-014r-0009000000-416c95b6b6ca7d458ed6	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Prostaglandin H2 20V, Positive-QTOF	splash10-014i-4298000000-1e1b7f327aae394c6509	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Prostaglandin H2 40V, Positive-QTOF	splash10-00r6-9600000000-0dcbe56cd4069bcb2350	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Prostaglandin H2 10V, Negative-QTOF	splash10-0udi-0009000000-c3076b041f51673c7c5b	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Prostaglandin H2 20V, Negative-QTOF	splash10-0gb9-0019000000-1908f881874f924ccebd	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Prostaglandin H2 40V, Negative-QTOF	splash10-001i-3094000000-05963bfb2b050a03f37c	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular
Membrane
Endoplasmic reticulum

Biospecimen Locations

Not Available

Tissue Locations

Platelet

Pathways

Name	SMPDB/PathBank	KEGG
Arachidonic Acid Metabolism
Leukotriene C4 Synthesis Deficiency		Not Available
Piroxicam Action Pathway		Not Available
Acetylsalicylic Acid Action Pathway		Not Available
Etodolac Action Pathway		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

FDB031134

KNApSAcK ID

Not Available

Chemspider ID

392800

KEGG Compound ID

C00427

BioCyc ID

Not Available

BiGG ID

Wikipedia Link

METLIN ID

PubChem Compound

PDB ID

Not Available

ChEBI ID

15554

Food Biomarker Ontology

Not Available

VMH ID

PROSTGH2

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Onguru O, Casey MB, Kajita S, Nakamura N, Lloyd RV: Cyclooxygenase-2 and thromboxane synthase in non-endocrine and endocrine tumors: a review. Endocr Pathol. 2005 Winter;16(4):253-77. [PubMed:16627914 ]
Rybicki JP, Le Breton GC: Prostaglandin H2 directly lowers human platelet cAMP levels. Thromb Res. 1983 Jun 1;30(5):407-14. [PubMed:6310815 ]
Ulrich CM, Carlson CS, Sibert J, Poole EM, Yu JH, Wang LH, Sparks R, Potter JD, Bigler J: Thromboxane synthase (TBXAS1) polymorphisms in African-American and Caucasian populations: evidence for selective pressure. Hum Mutat. 2005 Oct;26(4):394-5. [PubMed:16134166 ]
Hornberger W, Patscheke H: Transient concentrations and agonist potency of PGH2 in platelet activation by endogenous arachidonate. Eicosanoids. 1989;2(4):241-8. [PubMed:2517034 ]
Johnson GJ, Dunlop PC, Leis LA, From AH: Dihydropyridine agonist Bay K 8644 inhibits platelet activation by competitive antagonism of thromboxane A2-prostaglandin H2 receptor. Circ Res. 1988 Mar;62(3):494-505. [PubMed:2449295 ]
Maclouf J, Kindahl H, Granstrom E, Samuelsson B: Interactions of prostaglandin H2 and thromboxane A2 with human serum albumin. Eur J Biochem. 1980 Aug;109(2):561-6. [PubMed:7408901 ]
Gerrard JM, White JG, Rao GH, Townsend D: Localization of platelet prostaglandin production in the platelet dense tubular system. Am J Pathol. 1976 May;83(2):283-98. [PubMed:1266944 ]
Patscheke H, Hornberger W, Zehender H: Pathophysiological role of thromboxane A2 and pharmacological approaches to its inhibition. Z Kardiol. 1990;79 Suppl 3:151-4. [PubMed:2099038 ]
Goerig M, Habenicht AJ, Zeh W, Salbach P, Kommerell B, Rothe DE, Nastainczyk W, Glomset JA: Evidence for coordinate, selective regulation of eicosanoid synthesis in platelet-derived growth factor-stimulated 3T3 fibroblasts and in HL-60 cells induced to differentiate into macrophages or neutrophils. J Biol Chem. 1988 Dec 25;263(36):19384-91. [PubMed:2848824 ]
Beitz J, Forster W: Influence of human low density and high density lipoprotein cholesterol on the in vitro prostaglandin I2 synthetase activity. Biochim Biophys Acta. 1980 Dec 5;620(3):352-5. [PubMed:6786342 ]
Mevkh AT, Basevich VV, Varfolomeev SD: [Synthesis of thromboxane A2: limiting stages of primary thrombocyte aggregation in humans initiated by arachidonic acid and its metabolic products]. Biokhimiia. 1984 Dec;49(12):2035-40. [PubMed:6441604 ]
Basevich VV, Mevkh AT, Varfolomeev SD: [Kinetic mechanisms of enzyme activity of the thromboxane synthetase system. Thromboxane synthetase of human platelets]. Biokhimiia. 1984 Sep;49(9):1538-45. [PubMed:6440597 ]
Gresele P, Deckmyn H, Nenci GG, Vermylen J: Thromboxane synthase inhibitors, thromboxane receptor antagonists and dual blockers in thrombotic disorders. Trends Pharmacol Sci. 1991 Apr;12(4):158-63. [PubMed:1829559 ]
Borg C, Lam SC, Dieter JP, Lim CT, Komiotis D, Venton DL, Le Breton GC: Anti-peptide antibodies against the human blood platelet thromboxane A2/prostaglandin H2 receptor. Production, purification and characterization. Biochem Pharmacol. 1993 May 25;45(10):2071-8. [PubMed:7685602 ]
Miller OV, Johnson RA, Gorman RR: Inhibition of PGE1-stimulated cAMP accumulation in human platelets by thromboxane a2. Prostaglandins. 1977 Apr;13(4):599-609. [PubMed:193153 ]
Kuzuya T, Hoshida S, Yamagishi M, Ohmori M, Inoue M, Kamada T, Tada M: Effect of OKY-046, a thromboxane A2 synthetase inhibitor, on arachidonate-induced platelet aggregation: possible role of "prostaglandin H2 steal" mechanism. Jpn Circ J. 1986 Nov;50(11):1071-8. [PubMed:3102802 ]
Vezza R, Mezzasoma AM, Venditti G, Gresele P: Prostaglandin endoperoxides and thromboxane A2 activate the same receptor isoforms in human platelets. Thromb Haemost. 2002 Jan;87(1):114-21. [PubMed:11848439 ]
Ushikubi F, Nakajima M, Hirata M, Okuma M, Fujiwara M, Narumiya S: Purification of the thromboxane A2/prostaglandin H2 receptor from human blood platelets. J Biol Chem. 1989 Oct 5;264(28):16496-501. [PubMed:2528545 ]
Hornberger WB, Patscheke H: Prostaglandin H2 in human platelet activation: coactivator and substitute for thromboxane A2. Prog Clin Biol Res. 1989;301:315-9. [PubMed:2798452 ]
Salomon RG: Levuglandins and isolevuglandins: stealthy toxins of oxidative injury. Antioxid Redox Signal. 2005 Jan-Feb;7(1-2):185-201. [PubMed:15650407 ]
Folco G, Murphy RC: Eicosanoid transcellular biosynthesis: from cell-cell interactions to in vivo tissue responses. Pharmacol Rev. 2006 Sep;58(3):375-88. [PubMed:16968946 ]

Enzymes

Enzyme Details

1. Prostaglandin E synthase

General function:: Involved in prostaglandin-E synthase activity
Specific function:: Catalyzes the oxidoreduction of prostaglandin endoperoxide H2 (PGH2) to prostaglandin E2 (PGE2).
Gene Name:: PTGES
Uniprot ID:: O14684
Molecular weight:: 17102.135

Reactions

Prostaglandin H2 → Prostaglandin E2	details

Enzyme Details

2. Prostaglandin G/H synthase 2

General function:: Involved in peroxidase activity
Specific function:: Mediates the formation of prostaglandins from arachidonate. May have a role as a major mediator of inflammation and/or a role for prostanoid signaling in activity-dependent plasticity.
Gene Name:: PTGS2
Uniprot ID:: P35354
Molecular weight:: 68995.625

Reactions

Prostaglandin H2 + Acceptor + Water → Prostaglandin G2 + Reduced acceptor	details

Enzyme Details

3. Prostaglandin G/H synthase 1

General function:: Involved in peroxidase activity
Specific function:: May play an important role in regulating or promoting cell proliferation in some normal and neoplastically transformed cells.
Gene Name:: PTGS1
Uniprot ID:: P23219
Molecular weight:: 68685.82

Reactions

Prostaglandin H2 + Acceptor + Water → Prostaglandin G2 + Reduced acceptor	details

Enzyme Details

4. Prostacyclin synthase

General function:: Involved in monooxygenase activity
Specific function:: Catalyzes the isomerization of prostaglandin H2 to prostacyclin (= prostaglandin I2).
Gene Name:: PTGIS
Uniprot ID:: Q16647
Molecular weight:: 57103.385

Reactions

Prostaglandin H2 → Prostaglandin I2	details

Enzyme Details

5. Hematopoietic prostaglandin D synthase

General function:: Involved in glutathione transferase activity
Specific function:: Bifunctional enzyme which catalyzes both the conversion of PGH2 to PGD2, a prostaglandin involved in smooth muscle contraction/relaxation and a potent inhibitor of platelet aggregation, and the conjugation of glutathione with a wide range of aryl halides and organic isothiocyanates. Also exhibits low glutathione-peroxidase activity towards cumene hydroperoxide.
Gene Name:: HPGDS
Uniprot ID:: O60760
Molecular weight:: 23343.65

Reactions

Prostaglandin H2 → Prostaglandin D2	details

Enzyme Details

6. Prostaglandin-H2 D-isomerase

General function:: Involved in binding
Specific function:: Catalyzes the conversion of PGH2 to PGD2, a prostaglandin involved in smooth muscle contraction/relaxation and a potent inhibitor of platelet aggregation. Involved in a variety of CNS functions, such as sedation, NREM sleep and PGE2-induced allodynia, and may have an anti-apoptotic role in oligodendrocytes. Binds small non-substrate lipophilic molecules, including biliverdin, bilirubin, retinal, retinoic acid and thyroid hormone, and may act as a scavenger for harmful hydrophopic molecules and as a secretory retinoid and thyroid hormone transporter. Possibly involved in development and maintenance of the blood-brain, blood-retina, blood-aqueous humor and blood-testis barrier. It is likely to play important roles in both maturation and maintenance of the central nervous system and male reproductive system.
Gene Name:: PTGDS
Uniprot ID:: P41222
Molecular weight:: 21028.665

Reactions

Prostaglandin H2 → Prostaglandin D2	details

Enzyme Details

7. Thromboxane-A synthase

General function:: Involved in monooxygenase activity
Specific function:: Not Available
Gene Name:: TBXAS1
Uniprot ID:: P24557
Molecular weight:: 60648.885

Reactions

Prostaglandin H2 → Thromboxane A2	details

Enzyme Details

8. Prostaglandin E synthase 2

General function:: Involved in electron carrier activity
Specific function:: Isomerase that catalyzes the conversion of unstable intermediate of prostaglandin E2 H2 (PGH2) into the more stable prostaglandin E2 (PGE2) form. May also have transactivation activity toward IFN-gamma (IFNG), possibly via an interaction with CEBPB; however, the relevance of transcription activation activity remains unclear.
Gene Name:: PTGES2
Uniprot ID:: Q9H7Z7
Molecular weight:: 21337.205

Reactions

Prostaglandin H2 → Prostaglandin E2	details

Enzyme Details

9. HCG14925, isoform CRA_a

General function:: Involved in monooxygenase activity
Specific function:: Not Available
Gene Name:: Not Available
Uniprot ID:: Q53F23
Molecular weight:: 60648.9

Enzyme Details

10. Prostaglandin E synthase 3

General function:: Involved in prostaglandin-E synthase activity
Specific function:: Molecular chaperone that localizes to genomic response elements in a hormone-dependent manner and disrupts receptor-mediated transcriptional activation, by promoting disassembly of transcriptional regulatory complexes.
Gene Name:: PTGES3
Uniprot ID:: Q15185
Molecular weight:: 18697.195

Reactions

Prostaglandin H2 → Prostaglandin E2	details

Showing metabocard for Prostaglandin H2 (HMDB0001381)

MOL for HMDB0001381 (Prostaglandin H2)

3D MOL for HMDB0001381 (Prostaglandin H2)

3D SDF for HMDB0001381 (Prostaglandin H2)

3D-SDF for HMDB0001381 (Prostaglandin H2)

PDB for HMDB0001381 (Prostaglandin H2)

3D PDB for HMDB0001381 (Prostaglandin H2)

SMILES for HMDB0001381 (Prostaglandin H2)

INCHI for HMDB0001381 (Prostaglandin H2)

Structure for HMDB0001381 (Prostaglandin H2)

3D Structure for HMDB0001381 (Prostaglandin H2)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

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