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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (3) Show 3 proteins XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2006-05-22 15:12:43 UTC

Update Date

2022-07-12 23:05:07 UTC

HMDB ID

HMDB0003235

Secondary Accession Numbers

HMDB0005100
HMDB03235
HMDB05100

Metabolite Identification

Common Name

Prostaglandin G2

Description

Prostaglandin G2 (PGG2) is synthesized from arachidonic acid on a cyclooxygenase (COX) metabolic pathway as a primary step; the COX biosynthesis of prostaglandin (PG) begins with the highly specific oxygenation of arachidonic acid in the 11R configuration and ends with a 15S oxygenation to form PGG2. The COX site activity that catalyzes the conversion of arachidonic acid to PGG2 is the target for nonsteroidal antiinflammatory drugs (NSAIDs). The peroxidase site activity catalyzes the two-electron reduction of the hydroperoxide bond of PGG2 to yield the corresponding alcohol prostaglandin H2 (PGH2). The formation of a phenoxyl radical on Tyr385 couples the activities of the two sites. The Tyr385 radical is produced via oxidation by compound I, an oxoferryl porphyrin -cation radical, which is generated by reaction of the hemin resting state with PGG2 or other hydroperoxides. The tyrosyl radical homolytically abstracts the 13proS hydrogen atom of arachidonic acid which initiates a radical cascade that ends with the stereoselective formation of PGG2. PGG2 then migrates from the cyclooxygenase (COX) site to the peroxidase (POX) site where it reacts with the hemin group to generate PGH2 and compound I. The heterolytic oxygen-oxygen bond cleavage is assisted by the conserved distal residues His207 and Gln203, mutation of which has been shown to severely impair enzyme activity. Compound I, upon reaction with Tyr385, gives compound II, which in turn is reduced to the hemin resting state by one-electron oxidation of reducing cosubstrates or undergoes reactions that result in enzyme self-inactivation. Prostaglandin endoperoxide H synthase (PGHS) 1 is a bifunctional membrane enzyme of the endoplasmic reticulum that converts arachidonic acid into prostaglandin H2 (PGH2), the precursor of all prostaglandins, thromboxanes, and prostacyclins. These lipid mediators are intricately involved in normal physiology, namely, in mitogenesis, fever generation, pain response, lymphocyte chemotaxis, fertility, and contradictory stimuli such as vasoconstriction and vasodilatation, as well as platelet aggregation and quiescence. PGHS is implicated in numerous pathologies, including inflammation, cancers of the colon, lung, and breast, Alzheimer's disease, Parkinson's disease, and numerous cardiovascular diseases including atherosclerosis, thrombosis, myocardial infarction, and stroke. (PMID: 14594816 , 16552393 , 16411757 ). 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, 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

PGX
  Mrv0541 02231217142D          

 31 32  0  0  0  0            999 V2000
    1.0661   -4.1518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7985   -3.3714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0112   -3.2130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2788   -2.4326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2632   -1.8106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0044   -1.0302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8141   -0.8718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0817   -0.0914    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8122    0.2789    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7421    1.8147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5821    0.9993    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7866    0.5340    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0015    0.7780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6069    0.2176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3950    0.4616    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5776    1.2662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9722    1.8266    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1549    2.6311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5495    3.1916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7322    3.9961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8757   -4.3102    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5241   -4.7737    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5877   -0.1114    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2224    0.5491    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0004   -0.0988    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8177   -0.9033    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5222   -0.4747    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8130   -0.3051    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4055    1.5559    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4037    0.0931    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9665    0.8583    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1 21  2  0  0  0  0
  1 22  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  8  7  1  1  0  0  0
  8  9  1  0  0  0  0
  8 12  1  0  0  0  0
  8 27  1  6  0  0  0
  9 10  1  0  0  0  0
  9 23  1  0  0  0  0
  9 28  1  6  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 24  1  0  0  0  0
 11 29  1  1  0  0  0
 12 13  1  6  0  0  0
 12 30  1  1  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 25  1  1  0  0  0
 15 31  1  1  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 23 24  1  0  0  0  0
 25 26  1  0  0  0  0
M  END

HMDB0003235
     RDKit          3D
Prostaglandin G2
 58 59  0  0  0  0  0  0  0  0999 V2000
    6.1281   -1.0483    0.4014 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7580   -0.1882   -0.6310 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8448    0.5091   -1.5516 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8660    1.4803   -1.0339 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7681    0.9858   -0.1545 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9189    0.0254   -0.9605 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7867   -0.5439   -0.1539 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5896   -0.0325   -0.1542 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5252   -0.5881    0.6355 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0394   -1.6642    1.5464 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5951   -0.8064    2.6552 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7731   -0.1270    2.9635 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4960   -1.2738    3.1396 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1481   -2.1442    2.2607 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0339    0.4705    1.6399 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4628    0.8533    1.3813 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4382   -0.2232    1.4558 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1676   -0.5720    0.4247 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0940    0.0519   -0.8799 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4065    0.6842   -1.2803 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4629   -0.3902   -1.3254 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7305    0.2485   -1.7344 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9288    0.4997   -2.9428 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6708    0.5560   -0.7796 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3760    0.6665   -2.0814 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7797    0.0711   -3.1609 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1452   -1.4547    0.1511 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7854   -1.9787    0.5777 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0724   -0.5417    1.4046 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4016    0.5990   -0.1114 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4870   -0.8312   -1.2336 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3619   -0.2711   -2.2170 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5013    1.0779   -2.3004 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4021    2.3463   -0.5143 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3440    1.9832   -1.9153 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1482    0.5641    0.7817 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1513    1.8843    0.1450 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5330   -0.7991   -1.3118 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0242   -1.4075    0.4372 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4324    0.8676   -0.7921 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3747   -0.9184   -0.0096 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5806   -2.4383    1.1555 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9337   -1.4024    3.4983 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2844   -0.0574    2.2694 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6993    0.5331    3.8098 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4197    1.4108    1.4867 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7932    1.6073    2.1844 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4567    1.4604    0.4595 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5447   -0.7247    2.4346 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8721   -1.4118    0.5982 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2307    0.6682   -1.1206 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9930   -0.8213   -1.6271 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3295    1.2394   -2.2327 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6868    1.3687   -0.4313 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5426   -0.8120   -0.2851 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1489   -1.1831   -2.0460 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8234    1.4863   -0.4106 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2935    0.4563   -3.9219 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
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 12 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 22 24  1  0
  6 25  1  0
 25 26  1  0
 15  9  1  0
 14 10  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  2 30  1  0
  2 31  1  0
  3 32  1  0
  3 33  1  0
  4 34  1  0
  4 35  1  0
  5 36  1  0
  5 37  1  0
  6 38  1  6
  7 39  1  0
  8 40  1  0
  9 41  1  6
 10 42  1  6
 11 43  1  0
 11 44  1  0
 12 45  1  1
 15 46  1  1
 16 47  1  0
 16 48  1  0
 17 49  1  0
 18 50  1  0
 19 51  1  0
 19 52  1  0
 20 53  1  0
 20 54  1  0
 21 55  1  0
 21 56  1  0
 24 57  1  0
 26 58  1  0
M  END

PGX
  Mrv0541 02231217142D          

 31 32  0  0  0  0            999 V2000
    1.0661   -4.1518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7985   -3.3714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0112   -3.2130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2788   -2.4326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2632   -1.8106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0044   -1.0302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8141   -0.8718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0817   -0.0914    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8122    0.2789    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7421    1.8147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5821    0.9993    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7866    0.5340    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0015    0.7780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6069    0.2176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3950    0.4616    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5776    1.2662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9722    1.8266    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1549    2.6311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5495    3.1916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7322    3.9961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8757   -4.3102    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5241   -4.7737    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5877   -0.1114    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2224    0.5491    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0004   -0.0988    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8177   -0.9033    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5222   -0.4747    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8130   -0.3051    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4055    1.5559    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4037    0.0931    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9665    0.8583    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1 21  2  0  0  0  0
  1 22  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  8  7  1  1  0  0  0
  8  9  1  0  0  0  0
  8 12  1  0  0  0  0
  8 27  1  6  0  0  0
  9 10  1  0  0  0  0
  9 23  1  0  0  0  0
  9 28  1  6  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 24  1  0  0  0  0
 11 29  1  1  0  0  0
 12 13  1  6  0  0  0
 12 30  1  1  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 25  1  1  0  0  0
 15 31  1  1  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 23 24  1  0  0  0  0
 25 26  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0003235

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C20H32O6/c1-2-3-6-9-15(24-23)12-13-17-16(18-14-19(17)26-25-18)10-7-4-5-8-11-20(21)22/h4,7,12-13,15-19,23H,2-3,5-6,8-11,14H2,1H3,(H,21,22)/b7-4-,13-12+/t15-,16+,17+,18-,19+/m0/s1

> <INCHI_KEY>
SGUKUZOVHSFKPH-YNNPMVKQSA-N

> <FORMULA>
C20H32O6

> <MOLECULAR_WEIGHT>
368.4645

> <EXACT_MASS>
368.219888756

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
40.84761069185284

> <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-hydroperoxyoct-1-en-1-yl]-2,3-dioxabicyclo[2.2.1]heptan-5-yl]hept-5-enoic acid

> <ALOGPS_LOGP>
4.31

> <JCHEM_LOGP>
4.406262963333332

> <ALOGPS_LOGS>
-4.15

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
11.712417615263744

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.355293577134534

> <JCHEM_PKA_STRONGEST_BASIC>
-4.23678854343082

> <JCHEM_POLAR_SURFACE_AREA>
85.22000000000001

> <JCHEM_REFRACTIVITY>
99.3921

> <JCHEM_ROTATABLE_BOND_COUNT>
13

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.64e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
prostaglandin G2

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0003235
     RDKit          3D
Prostaglandin G2
 58 59  0  0  0  0  0  0  0  0999 V2000
    6.1281   -1.0483    0.4014 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7580   -0.1882   -0.6310 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8448    0.5091   -1.5516 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8660    1.4803   -1.0339 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7681    0.9858   -0.1545 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9189    0.0254   -0.9605 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7867   -0.5439   -0.1539 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5896   -0.0325   -0.1542 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5252   -0.5881    0.6355 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0394   -1.6642    1.5464 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5951   -0.8064    2.6552 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7731   -0.1270    2.9635 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4960   -1.2738    3.1396 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1481   -2.1442    2.2607 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0339    0.4705    1.6399 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4628    0.8533    1.3813 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4382   -0.2232    1.4558 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1676   -0.5720    0.4247 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0940    0.0519   -0.8799 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4065    0.6842   -1.2803 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4629   -0.3902   -1.3254 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7305    0.2485   -1.7344 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9288    0.4997   -2.9428 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6708    0.5560   -0.7796 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3760    0.6665   -2.0814 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7797    0.0711   -3.1609 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1452   -1.4547    0.1511 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7854   -1.9787    0.5777 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0724   -0.5417    1.4046 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4016    0.5990   -0.1114 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4870   -0.8312   -1.2336 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3619   -0.2711   -2.2170 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5013    1.0779   -2.3004 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4021    2.3463   -0.5143 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3440    1.9832   -1.9153 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1482    0.5641    0.7817 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1513    1.8843    0.1450 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5330   -0.7991   -1.3118 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0242   -1.4075    0.4372 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4324    0.8676   -0.7921 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3747   -0.9184   -0.0096 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5806   -2.4383    1.1555 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9337   -1.4024    3.4983 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2844   -0.0574    2.2694 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6993    0.5331    3.8098 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4197    1.4108    1.4867 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7932    1.6073    2.1844 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4567    1.4604    0.4595 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5447   -0.7247    2.4346 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8721   -1.4118    0.5982 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2307    0.6682   -1.1206 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9930   -0.8213   -1.6271 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3295    1.2394   -2.2327 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6868    1.3687   -0.4313 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5426   -0.8120   -0.2851 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1489   -1.1831   -2.0460 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8234    1.4863   -0.4106 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2935    0.4563   -3.9219 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
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 12 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 22 24  1  0
  6 25  1  0
 25 26  1  0
 15  9  1  0
 14 10  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  2 30  1  0
  2 31  1  0
  3 32  1  0
  3 33  1  0
  4 34  1  0
  4 35  1  0
  5 36  1  0
  5 37  1  0
  6 38  1  6
  7 39  1  0
  8 40  1  0
  9 41  1  6
 10 42  1  6
 11 43  1  0
 11 44  1  0
 12 45  1  1
 15 46  1  1
 16 47  1  0
 16 48  1  0
 17 49  1  0
 18 50  1  0
 19 51  1  0
 19 52  1  0
 20 53  1  0
 20 54  1  0
 21 55  1  0
 21 56  1  0
 24 57  1  0
 26 58  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: PGX                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  C   UNK     0       1.990  -7.750   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.491  -6.293   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.021  -5.998   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.520  -4.541   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.491  -3.380   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.008  -1.923   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.520  -1.627   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.019  -0.171   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -3.383   0.521   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -3.252   3.387   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.953   1.865   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.468   0.997   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.003   1.452   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.133   0.406   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.604   0.862   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.945   2.364   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.815   3.410   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.156   4.911   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.026   5.958   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.367   7.459   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       3.501  -8.046   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       0.978  -8.911   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      -4.830  -0.208   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      -4.148   1.025   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       3.734  -0.184   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       3.393  -1.686   0.000  0.00  0.00           O+0
HETATM   27  H   UNK     0      -2.841  -0.886   0.000  0.00  0.00           H+0
HETATM   28  H   UNK     0      -3.384  -0.570   0.000  0.00  0.00           H+0
HETATM   29  H   UNK     0      -2.624   2.904   0.000  0.00  0.00           H+0
HETATM   30  H   UNK     0      -0.754   0.174   0.000  0.00  0.00           H+0
HETATM   31  H   UNK     0       1.804   1.602   0.000  0.00  0.00           H+0
CONECT    1    2   21   22                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   12   27                                             
CONECT    9    8   10   23   28                                             
CONECT   10    9   11                                                       
CONECT   11   10   12   24   29                                             
CONECT   12    8   11   13   30                                             
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   25   31                                             
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19                                                            
CONECT   21    1                                                            
CONECT   22    1                                                            
CONECT   23    9   24                                                       
CONECT   24   11   23                                                       
CONECT   25   15   26                                                       
CONECT   26   25                                                            
CONECT   27    8                                                            
CONECT   28    9                                                            
CONECT   29   11                                                            
CONECT   30   12                                                            
CONECT   31   15                                                            
MASTER        0    0    0    0    0    0    0    0   31    0   64    0
END

COMPND    HMDB0003235
HETATM    1  C1  UNL     1       6.128  -1.048   0.401  1.00  0.00           C  
HETATM    2  C2  UNL     1       6.758  -0.188  -0.631  1.00  0.00           C  
HETATM    3  C3  UNL     1       5.845   0.509  -1.552  1.00  0.00           C  
HETATM    4  C4  UNL     1       4.866   1.480  -1.034  1.00  0.00           C  
HETATM    5  C5  UNL     1       3.768   0.986  -0.154  1.00  0.00           C  
HETATM    6  C6  UNL     1       2.919   0.025  -0.960  1.00  0.00           C  
HETATM    7  C7  UNL     1       1.787  -0.544  -0.154  1.00  0.00           C  
HETATM    8  C8  UNL     1       0.590  -0.033  -0.154  1.00  0.00           C  
HETATM    9  C9  UNL     1      -0.525  -0.588   0.636  1.00  0.00           C  
HETATM   10  C10 UNL     1      -0.039  -1.664   1.546  1.00  0.00           C  
HETATM   11  C11 UNL     1       0.595  -0.806   2.655  1.00  0.00           C  
HETATM   12  C12 UNL     1      -0.773  -0.127   2.963  1.00  0.00           C  
HETATM   13  O1  UNL     1      -1.496  -1.274   3.140  1.00  0.00           O  
HETATM   14  O2  UNL     1      -1.148  -2.144   2.261  1.00  0.00           O  
HETATM   15  C13 UNL     1      -1.034   0.471   1.640  1.00  0.00           C  
HETATM   16  C14 UNL     1      -2.463   0.853   1.381  1.00  0.00           C  
HETATM   17  C15 UNL     1      -3.438  -0.223   1.456  1.00  0.00           C  
HETATM   18  C16 UNL     1      -4.168  -0.572   0.425  1.00  0.00           C  
HETATM   19  C17 UNL     1      -4.094   0.052  -0.880  1.00  0.00           C  
HETATM   20  C18 UNL     1      -5.406   0.684  -1.280  1.00  0.00           C  
HETATM   21  C19 UNL     1      -6.463  -0.390  -1.325  1.00  0.00           C  
HETATM   22  C20 UNL     1      -7.731   0.248  -1.734  1.00  0.00           C  
HETATM   23  O3  UNL     1      -7.929   0.500  -2.943  1.00  0.00           O  
HETATM   24  O4  UNL     1      -8.671   0.556  -0.780  1.00  0.00           O  
HETATM   25  O5  UNL     1       2.376   0.666  -2.081  1.00  0.00           O  
HETATM   26  O6  UNL     1       2.780   0.071  -3.161  1.00  0.00           O  
HETATM   27  H1  UNL     1       5.145  -1.455   0.151  1.00  0.00           H  
HETATM   28  H2  UNL     1       6.785  -1.979   0.578  1.00  0.00           H  
HETATM   29  H3  UNL     1       6.072  -0.542   1.405  1.00  0.00           H  
HETATM   30  H4  UNL     1       7.402   0.599  -0.111  1.00  0.00           H  
HETATM   31  H5  UNL     1       7.487  -0.831  -1.234  1.00  0.00           H  
HETATM   32  H6  UNL     1       5.362  -0.271  -2.217  1.00  0.00           H  
HETATM   33  H7  UNL     1       6.501   1.078  -2.300  1.00  0.00           H  
HETATM   34  H8  UNL     1       5.402   2.346  -0.514  1.00  0.00           H  
HETATM   35  H9  UNL     1       4.344   1.983  -1.915  1.00  0.00           H  
HETATM   36  H10 UNL     1       4.148   0.564   0.782  1.00  0.00           H  
HETATM   37  H11 UNL     1       3.151   1.884   0.145  1.00  0.00           H  
HETATM   38  H12 UNL     1       3.533  -0.799  -1.312  1.00  0.00           H  
HETATM   39  H13 UNL     1       2.024  -1.407   0.437  1.00  0.00           H  
HETATM   40  H14 UNL     1       0.432   0.868  -0.792  1.00  0.00           H  
HETATM   41  H15 UNL     1      -1.375  -0.918  -0.010  1.00  0.00           H  
HETATM   42  H16 UNL     1       0.581  -2.438   1.156  1.00  0.00           H  
HETATM   43  H17 UNL     1       0.934  -1.402   3.498  1.00  0.00           H  
HETATM   44  H18 UNL     1       1.284  -0.057   2.269  1.00  0.00           H  
HETATM   45  H19 UNL     1      -0.699   0.533   3.810  1.00  0.00           H  
HETATM   46  H20 UNL     1      -0.420   1.411   1.487  1.00  0.00           H  
HETATM   47  H21 UNL     1      -2.793   1.607   2.184  1.00  0.00           H  
HETATM   48  H22 UNL     1      -2.457   1.460   0.459  1.00  0.00           H  
HETATM   49  H23 UNL     1      -3.545  -0.725   2.435  1.00  0.00           H  
HETATM   50  H24 UNL     1      -4.872  -1.412   0.598  1.00  0.00           H  
HETATM   51  H25 UNL     1      -3.231   0.668  -1.121  1.00  0.00           H  
HETATM   52  H26 UNL     1      -3.993  -0.821  -1.627  1.00  0.00           H  
HETATM   53  H27 UNL     1      -5.329   1.239  -2.233  1.00  0.00           H  
HETATM   54  H28 UNL     1      -5.687   1.369  -0.431  1.00  0.00           H  
HETATM   55  H29 UNL     1      -6.543  -0.812  -0.285  1.00  0.00           H  
HETATM   56  H30 UNL     1      -6.149  -1.183  -2.046  1.00  0.00           H  
HETATM   57  H31 UNL     1      -8.823   1.486  -0.411  1.00  0.00           H  
HETATM   58  H32 UNL     1       2.293   0.456  -3.922  1.00  0.00           H  
CONECT    1    2   27   28   29
CONECT    2    3   30   31
CONECT    3    4   32   33
CONECT    4    5   34   35
CONECT    5    6   36   37
CONECT    6    7   25   38
CONECT    7    8    8   39
CONECT    8    9   40
CONECT    9   10   15   41
CONECT   10   11   14   42
CONECT   11   12   43   44
CONECT   12   13   15   45
CONECT   13   14
CONECT   15   16   46
CONECT   16   17   47   48
CONECT   17   18   18   49
CONECT   18   19   50
CONECT   19   20   51   52
CONECT   20   21   53   54
CONECT   21   22   55   56
CONECT   22   23   23   24
CONECT   24   57
CONECT   25   26
CONECT   26   58
END

HMDB0003235
     RDKit          3D
Prostaglandin G2
 58 59  0  0  0  0  0  0  0  0999 V2000
    6.1281   -1.0483    0.4014 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7580   -0.1882   -0.6310 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8448    0.5091   -1.5516 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8660    1.4803   -1.0339 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7681    0.9858   -0.1545 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9189    0.0254   -0.9605 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7867   -0.5439   -0.1539 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5896   -0.0325   -0.1542 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5252   -0.5881    0.6355 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0394   -1.6642    1.5464 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5951   -0.8064    2.6552 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7731   -0.1270    2.9635 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4960   -1.2738    3.1396 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1481   -2.1442    2.2607 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0339    0.4705    1.6399 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4628    0.8533    1.3813 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4382   -0.2232    1.4558 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1676   -0.5720    0.4247 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0940    0.0519   -0.8799 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4065    0.6842   -1.2803 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4629   -0.3902   -1.3254 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7305    0.2485   -1.7344 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9288    0.4997   -2.9428 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6708    0.5560   -0.7796 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3760    0.6665   -2.0814 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7797    0.0711   -3.1609 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1452   -1.4547    0.1511 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7854   -1.9787    0.5777 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0724   -0.5417    1.4046 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4016    0.5990   -0.1114 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4870   -0.8312   -1.2336 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3619   -0.2711   -2.2170 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5013    1.0779   -2.3004 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4021    2.3463   -0.5143 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3440    1.9832   -1.9153 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1482    0.5641    0.7817 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1513    1.8843    0.1450 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5330   -0.7991   -1.3118 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0242   -1.4075    0.4372 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4324    0.8676   -0.7921 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3747   -0.9184   -0.0096 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5806   -2.4383    1.1555 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9337   -1.4024    3.4983 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2844   -0.0574    2.2694 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6993    0.5331    3.8098 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4197    1.4108    1.4867 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7932    1.6073    2.1844 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4567    1.4604    0.4595 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5447   -0.7247    2.4346 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8721   -1.4118    0.5982 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2307    0.6682   -1.1206 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9930   -0.8213   -1.6271 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3295    1.2394   -2.2327 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6868    1.3687   -0.4313 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5426   -0.8120   -0.2851 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1489   -1.1831   -2.0460 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8234    1.4863   -0.4106 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2935    0.4563   -3.9219 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
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 12 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 22 24  1  0
  6 25  1  0
 25 26  1  0
 15  9  1  0
 14 10  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  2 30  1  0
  2 31  1  0
  3 32  1  0
  3 33  1  0
  4 34  1  0
  4 35  1  0
  5 36  1  0
  5 37  1  0
  6 38  1  6
  7 39  1  0
  8 40  1  0
  9 41  1  6
 10 42  1  6
 11 43  1  0
 11 44  1  0
 12 45  1  1
 15 46  1  1
 16 47  1  0
 16 48  1  0
 17 49  1  0
 18 50  1  0
 19 51  1  0
 19 52  1  0
 20 53  1  0
 20 54  1  0
 21 55  1  0
 21 56  1  0
 24 57  1  0
 26 58  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
PGG2	ChEBI
(5Z)-7-{(1R,4S,5R,6R)-6-[(1E,3S)-3-hydroperoxyoct-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-hydroperoxyoct-1-en-1-yl]-2,3-dioxabicyclo[2.2.1]hept-5-yl}hept-5-enoic acid	HMDB
9,11-Epidioxy-15-hydroperoxy-prosta-5,13-dien-1-Oate	HMDB
9,11-Epidioxy-15-hydroperoxy-prosta-5,13-dien-1-Oic acid	HMDB
9S,11R-Epidioxy-15S-hydroperoxy-5Z,13E-prostadienoate	HMDB
9S,11R-Epidioxy-15S-hydroperoxy-5Z,13E-prostadienoic acid	HMDB
Endoperoxide g2	HMDB
PGG(2)	HMDB

Chemical Formula

C₂₀H₃₂O₆

Average Molecular Weight

368.4645

Monoisotopic Molecular Weight

368.219888756

IUPAC Name

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

Traditional Name

prostaglandin G2

CAS Registry Number

51982-36-6

SMILES

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

InChI Identifier

InChI=1S/C20H32O6/c1-2-3-6-9-15(24-23)12-13-17-16(18-14-19(17)26-25-18)10-7-4-5-8-11-20(21)22/h4,7,12-13,15-19,23H,2-3,5-6,8-11,14H2,1H3,(H,21,22)/b7-4-,13-12+/t15-,16+,17+,18-,19+/m0/s1

InChI Key

SGUKUZOVHSFKPH-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
Hydroperoxy fatty acid
Heterocyclic fatty acid
Ortho-dioxane
Fatty acid
Unsaturated fatty acid
Allylic hydroperoxide
Ortho-dioxolane
Dialkyl peroxide
Hydroperoxide
Alkyl hydroperoxide
Carboxylic acid derivative
Carboxylic acid
Oxacycle
Monocarboxylic acid or derivatives
Organoheterocyclic compound
Peroxol
Hydrocarbon derivative
Carbonyl group
Organic oxygen compound
Organooxygen compound
Organic oxide
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

prostaglandins G (CHEBI:27647 )
Prostaglandins (C05956 )
Prostaglandins (LMFA03010009 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0003235)
Extracellular (HMDB: HMDB0003235)

Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)
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)

Equine

Horse (FooDB: FOOD00378)

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)

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Arachidonic Acid Metabolism (HMDB: HMDB0003235)

Disease pathway

Leukotriene C4 Synthesis Deficiency (PathBank: SMP0000353)

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

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M-H]-	Not Available	194.3	http://allccs.zhulab.cn/database/detail?ID=AllCCS00001911

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.026 g/L	ALOGPS
logP	4.31	ALOGPS
logP	4.41	ChemAxon
logS	-4.2	ALOGPS
pKa (Strongest Acidic)	4.36	ChemAxon
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	85.22 Å²	ChemAxon
Rotatable Bond Count	13	ChemAxon
Refractivity	99.39 m³·mol⁻¹	ChemAxon
Polarizability	40.85 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]+	189.888	31661259
DarkChem	[M-H]-	194.255	31661259
DeepCCS	[M+H]+	196.705	30932474
DeepCCS	[M-H]-	194.81	30932474
DeepCCS	[M-2H]-	228.052	30932474
DeepCCS	[M+Na]+	202.449	30932474
AllCCS	[M+H]+	195.3	32859911
AllCCS	[M+H-H2O]+	192.8	32859911
AllCCS	[M+NH4]+	197.7	32859911
AllCCS	[M+Na]+	198.3	32859911
AllCCS	[M-H]-	194.9	32859911
AllCCS	[M+Na-2H]-	196.3	32859911
AllCCS	[M+HCOO]-	197.9	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Prostaglandin G2	[H][C@@](CCCCC)(OO)\C=C\[C@@]1([H])[C@@]2([H])C[C@]([H])(OO2)[C@]1([H])C\C=C/CCCC(O)=O	4149.8	Standard polar	33892256
Prostaglandin G2	[H][C@@](CCCCC)(OO)\C=C\[C@@]1([H])[C@@]2([H])C[C@]([H])(OO2)[C@]1([H])C\C=C/CCCC(O)=O	2531.9	Standard non polar	33892256
Prostaglandin G2	[H][C@@](CCCCC)(OO)\C=C\[C@@]1([H])[C@@]2([H])C[C@]([H])(OO2)[C@]1([H])C\C=C/CCCC(O)=O	2759.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Prostaglandin G2,1TMS,isomer #1	CCCCC[C@@H](/C=C/[C@H]1[C@H]2C[C@H](OO2)[C@@H]1C/C=C\CCCC(=O)O[Si](C)(C)C)OO	2751.9	Semi standard non polar	33892256
Prostaglandin G2,1TBDMS,isomer #1	CCCCC[C@@H](/C=C/[C@H]1[C@H]2C[C@H](OO2)[C@@H]1C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C)OO	2968.8	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 G2 GC-MS (Non-derivatized) - 70eV, Positive	splash10-006x-5293000000-4f6f219630c974fad684	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Prostaglandin G2 GC-MS (1 TMS) - 70eV, Positive	splash10-00gr-9142200000-12079cbb99c54d74b4e4	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Prostaglandin G2 GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Prostaglandin G2 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 G2 10V, Positive-QTOF	splash10-0udi-0119000000-06893304af83e030a39b	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Prostaglandin G2 20V, Positive-QTOF	splash10-0zmr-3369000000-b1d0f67eea930b11ae4c	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Prostaglandin G2 40V, Positive-QTOF	splash10-1003-9400000000-7fbd48d8b1a086fc44d2	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Prostaglandin G2 10V, Negative-QTOF	splash10-014i-0019000000-4a1c6a9bb1b35fe201ef	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Prostaglandin G2 20V, Negative-QTOF	splash10-00r2-2149000000-16bc14c91731cdc79586	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Prostaglandin G2 40V, Negative-QTOF	splash10-0a4i-9162000000-ad0929ccdcab78d69a99	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Prostaglandin G2 10V, Positive-QTOF	splash10-0gb9-0009000000-7bd756fb66d8a2f4e9dd	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Prostaglandin G2 20V, Positive-QTOF	splash10-014r-2069000000-0067297ea99f20c4e4ca	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Prostaglandin G2 40V, Positive-QTOF	splash10-06ec-7920000000-d773a60db405a4944865	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Prostaglandin G2 10V, Negative-QTOF	splash10-00lr-0009000000-a2da7230358a405653f8	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Prostaglandin G2 20V, Negative-QTOF	splash10-00li-0029000000-c33c17a6864e28828b80	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Prostaglandin G2 40V, Negative-QTOF	splash10-014j-3096000000-14b691a730b064b98583	2021-09-22	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane (predicted from logP)

Biospecimen Locations

Not Available

Tissue Locations

Not Available

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

DB03866

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB023127

KNApSAcK ID

Not Available

Chemspider ID

4444406

KEGG Compound ID

C05956

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Prostaglandin G2

METLIN ID

3508

PubChem Compound

5280883

PDB ID

Not Available

ChEBI ID

27647

Food Biomarker Ontology

Not Available

VMH ID

HC02217

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Agnoli GC, Borgatti R, Cacciari M, Dorigoni S, Garutti C, Ikonomu E, Marinelli M: [Urinary excretion of prostanoids in the course of changes in diuresis over short and long terms respectively]. Boll Soc Ital Biol Sper. 1987 Apr 30;63(4):357-63. [PubMed:3447615 ]
Burdan F, Chalas A, Szumilo J: [Cyclooxygenase and prostanoids--biological implications]. Postepy Hig Med Dosw (Online). 2006;60:129-41. [PubMed:16552393 ]
Schneider C, Boeglin WE, Brash AR: Identification of two cyclooxygenase active site residues, Leucine 384 and Glycine 526, that control carbon ring cyclization in prostaglandin biosynthesis. J Biol Chem. 2004 Feb 6;279(6):4404-14. Epub 2003 Oct 31. [PubMed:14594816 ]
Chubb AJ, Fitzgerald DJ, Nolan KB, Moman E: The productive conformation of prostaglandin G2 at the peroxidase site of prostaglandin endoperoxide H synthase: docking, molecular dynamics, and site-directed mutagenesis studies. Biochemistry. 2006 Jan 24;45(3):811-20. [PubMed:16411757 ]

Enzymes

Enzyme Details

1. 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
Arachidonic acid + Oxygen → Prostaglandin G2	details

Enzyme Details

2. 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
Arachidonic acid + Oxygen → Prostaglandin G2	details

Enzyme Details

3. Aryl hydrocarbon receptor

General function:: Involved in transcription regulator activity
Specific function:: Ligand-activated transcriptional activator. Binds to the XRE promoter region of genes it activates. Activates the expression of multiple phase I and II xenobiotic chemical metabolizing enzyme genes (such as the CYP1A1 gene). Mediates biochemical and toxic effects of halogenated aromatic hydrocarbons. Involved in cell-cycle regulation. Likely to play an important role in the development and maturation of many tissues
Gene Name:: AHR
Uniprot ID:: P35869
Molecular weight:: 96146.7

Showing metabocard for Prostaglandin G2 (HMDB0003235)

MOL for HMDB0003235 (Prostaglandin G2)

3D MOL for HMDB0003235 (Prostaglandin G2)

3D SDF for HMDB0003235 (Prostaglandin G2)

3D-SDF for HMDB0003235 (Prostaglandin G2)

PDB for HMDB0003235 (Prostaglandin G2)

3D PDB for HMDB0003235 (Prostaglandin G2)

SMILES for HMDB0003235 (Prostaglandin G2)

INCHI for HMDB0003235 (Prostaglandin G2)

Structure for HMDB0003235 (Prostaglandin G2)

3D Structure for HMDB0003235 (Prostaglandin G2)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

Reactions

Reactions