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Record Information
StatusExpected but not Quantified
Creation Date2006-05-22 15:12:43 UTC
Update Date2017-12-20 20:32:50 UTC
Secondary Accession Numbers
  • HMDB03235
  • HMDB05100
Metabolite Identification
Common NameProstaglandin G2
DescriptionProstaglandin 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 signaling pathways.
(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 acidHMDB
9,11-Epidioxy-15-hydroperoxy-prosta-5,13-dien-1-Oic acidHMDB
9S,11R-Epidioxy-15S-hydroperoxy-5Z,13E-prostadienoic acidHMDB
Endoperoxide g2HMDB
Chemical FormulaC20H32O6
Average Molecular Weight368.4645
Monoisotopic Molecular Weight368.219888756
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 Nameprostaglandin G2
CAS Registry Number51982-36-6
InChI Identifier
Chemical Taxonomy
DescriptionThis compound 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
  • 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 FrameworkAliphatic heteropolycyclic compounds
External Descriptors

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  Pharmaceutical industry:

Biological role:


Physical Properties
Experimental Properties
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
Water Solubility0.026 g/LALOGPS
pKa (Strongest Acidic)4.36ChemAxon
pKa (Strongest Basic)-4.2ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area85.22 ŲChemAxon
Rotatable Bond Count13ChemAxon
Refractivity99.39 m³·mol⁻¹ChemAxon
Polarizability40.85 ųChemAxon
Number of Rings2ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-006x-5293000000-4f6f219630c974fad684View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00gr-9142200000-12079cbb99c54d74b4e4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0119000000-06893304af83e030a39bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0zmr-3369000000-b1d0f67eea930b11ae4cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-1003-9400000000-7fbd48d8b1a086fc44d2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0019000000-4a1c6a9bb1b35fe201efView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00r2-2149000000-16bc14c91731cdc79586View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9162000000-ad0929ccdcab78d69a99View in MoNA
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane (predicted from logP)
Biofluid LocationsNot Available
Tissue LocationNot Available
Suprofen Action PathwayThumbThumb?image type=greyscaleThumb?image type=simpleNot Available
Tenoxicam Action PathwayThumbThumb?image type=greyscaleThumb?image type=simpleNot Available
Tiaprofenic Acid Action PathwayThumbThumb?image type=greyscaleThumb?image type=simpleNot Available
Tolmetin Action PathwayThumbThumb?image type=greyscaleThumb?image type=simpleNot Available
Trisalicylate-choline Action PathwayThumbThumb?image type=greyscaleThumb?image type=simpleNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB03866
Phenol Explorer Compound IDNot Available
FoodDB IDFDB023127
KNApSAcK IDNot Available
Chemspider ID4444406
KEGG Compound IDC05956
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
PubChem Compound5280883
ChEBI ID27647
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. 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 ]
  2. Burdan F, Chalas A, Szumilo J: [Cyclooxygenase and prostanoids--biological implications]. Postepy Hig Med Dosw (Online). 2006;60:129-41. [PubMed:16552393 ]
  3. 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 ]
  4. 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 ]


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
Arachidonic acid + Oxygen → Prostaglandin G2details
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
Arachidonic acid + Oxygen → Prostaglandin G2details