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Record Information
StatusExpected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2021-09-14 15:47:03 UTC
Secondary Accession Numbers
  • HMDB01381
Metabolite Identification
Common NameProstaglandin H2
DescriptionProstaglandin 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.
(5Z,9alpha,11alpha,13E,15S)-9,11-Epidioxy-15-hydroxyprosta-5,13-dien-1-Oic acidChEBI
(5Z,13E)-(15S)-9a,11a-Epidioxy-15-hydroxyprosta-5,13-dienoic acidGenerator
(5Z,13E)-(15S)-9alpha,11alpha-Epidioxy-15-hydroxyprosta-5,13-dienoic acidGenerator
(5Z,13E)-(15S)-9Α,11α-epidioxy-15-hydroxyprosta-5,13-dienoic acidGenerator
(5Z,13E,15S)-9a,11a-Epidioxy-15-hydroxyprosta-5,13-dienoic acidGenerator
(5Z,13E,15S)-9alpha,11alpha-Epidioxy-15-hydroxyprosta-5,13-dienoic acidGenerator
(5Z,13E,15S)-9Α,11α-epidioxy-15-hydroxyprosta-5,13-dienoic acidGenerator
(5Z,9a,11a,13E,15S)-9,11-Epidioxy-15-hydroxyprosta-5,13-dien-1-Oic acidGenerator
(5Z,9Α,11α,13E,15S)-9,11-epidioxy-15-hydroxyprosta-5,13-dien-1-Oic acidGenerator
(5Z,9a,11a,13E,15S)-9,11-Epidioxy-15-hydroxy-prosta-5,13-dienoic acidGenerator
(5Z,9alpha,11alpha,13E,15S)-9,11-Epidioxy-15-hydroxy-prosta-5,13-dienoic acidGenerator
(5Z,9Α,11α,13E,15S)-9,11-epidioxy-15-hydroxy-prosta-5,13-dienoic acidGenerator
(15S)Hydroxy-9alpha,11alpha-(epoxymethano)prosta-5,13-dienoic acidHMDB
(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 acidHMDB
(5Z,13E)-(15S)-9,11-Epidioxy-15-hydroxyprosta-5,13-dienoic acidHMDB
(5Z,13E)-(15S)-9-alpha,11-alpha-Epidioxy-15-hydroxyprosta-5,13-dienoic acidHMDB
(5Z,13E,15S)-9-alpha,11-alpha-Epidioxy-15-hydroxyprosta-5,13-dienoic acidHMDB
(5Z,9alpha,11alpha,13E,15S)-9,11-Epidioxy-15-hydroxy-prosta-5,13-dien-1-Oic acidHMDB
15-Hydroxy-9alpha,11alpha-peroxidoprosta-5,13-dienoic acidHMDB
9S,11R-Epidioxy-15S-hydroxy-5Z,13E-prostadienoic acidHMDB
Endoperoxide H2HMDB
Prostaglandin R2HMDB
Chemical FormulaC20H32O5
Average Molecular Weight352.4651
Monoisotopic Molecular Weight352.224974134
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 Nameprostaglandin H2
CAS Registry Number42935-17-1
InChI Identifier
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.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassEicosanoids
Direct ParentProstaglandins and related compounds
Alternative Parents
  • 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 FrameworkAliphatic heteropolycyclic compounds
External Descriptors

Route of exposure:


Biological location:


Naturally occurring process:


Industrial application:

Biological role:

Physical Properties
Experimental Molecular Properties
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Molecular Properties
Water Solubility0.034 g/LALOGPS
pKa (Strongest Acidic)4.36ChemAxon
pKa (Strongest Basic)-1.6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area75.99 ŲChemAxon
Rotatable Bond Count12ChemAxon
Refractivity98.04 m³·mol⁻¹ChemAxon
Polarizability39.9 ųChemAxon
Number of Rings2ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Spectral Properties

Collision Cross Sections

NameAdductTypeData SourceValueReference
DarkChem[M+H]+PredictedNot Available186.18531661259
DarkChem[M-H]-PredictedNot Available191.41131661259
AllCCS[M+H]+PredictedNot Available192.71332859911
AllCCS[M-H]-PredictedNot Available192.59332859911

Retention Indices


Not Available


Prostaglandin H2,1TMS,#12698.7854
Prostaglandin H2,1TMS,#22660.9734
Prostaglandin H2,2TMS,#12703.465
Prostaglandin H2,1TBDMS,#12890.3193
Prostaglandin H2,1TBDMS,#22882.2568
Prostaglandin H2,2TBDMS,#13145.6736


Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-05d3-5192000000-448e0e493622387c96002017-09-01View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00gr-9221300000-2098865f8501844498322017-10-06View Spectrum
MSMass Spectrum (Electron Ionization)splash10-05d3-5192000000-448e0e493622387c96002021-09-05View Spectrum


Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0019000000-f1f4732bb2fcf1ecdd312017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00kr-4298000000-8f02063e16efefaecab32017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05tu-9300000000-e3cb6f0175b4d6d564752017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0009000000-661131f879ff507a5adf2017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0kai-1049000000-c49ffddba6a8b323d42f2017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9332000000-145fc48bf43661f2584f2017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014r-0009000000-416c95b6b6ca7d458ed62021-09-08View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-4298000000-1e1b7f327aae394c65092021-09-08View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00r6-9600000000-0dcbe56cd4069bcb23502021-09-08View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0009000000-c3076b041f51673c7c5b2021-09-08View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0gb9-0019000000-1908f881874f924ccebd2021-09-08View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-3094000000-05963bfb2b050a03f37c2021-09-08View Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
  • Endoplasmic reticulum
Biospecimen LocationsNot Available
Tissue Locations
  • Platelet
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB031134
KNApSAcK IDNot Available
Chemspider ID392800
KEGG Compound IDC00427
BioCyc IDNot Available
BiGG ID34952
Wikipedia LinkProstaglandin H2
PubChem Compound445049
PDB IDNot Available
ChEBI ID15554
Food Biomarker OntologyNot Available
MarkerDB IDNot Available
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. 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 ]
  2. Rybicki JP, Le Breton GC: Prostaglandin H2 directly lowers human platelet cAMP levels. Thromb Res. 1983 Jun 1;30(5):407-14. [PubMed:6310815 ]
  3. 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 ]
  4. 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 ]
  5. 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 ]
  6. 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 ]
  7. 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 ]
  8. 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 ]
  9. 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 ]
  10. 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 ]
  11. 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 ]
  12. 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 ]
  13. 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 ]
  14. 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 ]
  15. 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 ]
  16. 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 ]
  17. 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 ]
  18. 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 ]
  19. 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 ]
  20. Salomon RG: Levuglandins and isolevuglandins: stealthy toxins of oxidative injury. Antioxid Redox Signal. 2005 Jan-Feb;7(1-2):185-201. [PubMed:15650407 ]
  21. 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 ]


General function:
Involved in prostaglandin-E synthase activity
Specific function:
Catalyzes the oxidoreduction of prostaglandin endoperoxide H2 (PGH2) to prostaglandin E2 (PGE2).
Gene Name:
Uniprot ID:
Molecular weight:
Prostaglandin H2 → Prostaglandin E2details
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:
Uniprot ID:
Molecular weight:
Prostaglandin H2 + Acceptor + Water → Prostaglandin G2 + Reduced acceptordetails
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:
Uniprot ID:
Molecular weight:
Prostaglandin H2 + Acceptor + Water → Prostaglandin G2 + Reduced acceptordetails
General function:
Involved in monooxygenase activity
Specific function:
Catalyzes the isomerization of prostaglandin H2 to prostacyclin (= prostaglandin I2).
Gene Name:
Uniprot ID:
Molecular weight:
Prostaglandin H2 → Prostaglandin I2details
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:
Uniprot ID:
Molecular weight:
Prostaglandin H2 → Prostaglandin D2details
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:
Uniprot ID:
Molecular weight:
Prostaglandin H2 → Prostaglandin D2details
General function:
Involved in monooxygenase activity
Specific function:
Not Available
Gene Name:
Uniprot ID:
Molecular weight:
Prostaglandin H2 → Thromboxane A2details
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:
Uniprot ID:
Molecular weight:
Prostaglandin H2 → Prostaglandin E2details
General function:
Involved in monooxygenase activity
Specific function:
Not Available
Gene Name:
Not Available
Uniprot ID:
Molecular weight:
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:
Uniprot ID:
Molecular weight:
Prostaglandin H2 → Prostaglandin E2details