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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2006-05-22 15:12:43 UTC
Update Date2022-07-12 23:05:07 UTC
HMDB IDHMDB0003235
Secondary Accession Numbers
  • HMDB0005100
  • 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 signalling pathways.
Structure
Data?1582752267
Synonyms
ValueSource
PGG2ChEBI
(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-enoateHMDB
(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-OateHMDB
9,11-Epidioxy-15-hydroperoxy-prosta-5,13-dien-1-Oic acidHMDB
9S,11R-Epidioxy-15S-hydroperoxy-5Z,13E-prostadienoateHMDB
9S,11R-Epidioxy-15S-hydroperoxy-5Z,13E-prostadienoic acidHMDB
Endoperoxide g2HMDB
PGG(2)HMDB
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
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 KeySGUKUZOVHSFKPH-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.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassEicosanoids
Direct ParentProstaglandins 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 FrameworkAliphatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Process
Naturally occurring process
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M-H]-Not Available194.3http://allccs.zhulab.cn/database/detail?ID=AllCCS00001911
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.026 g/LALOGPS
logP4.31ALOGPS
logP4.41ChemAxon
logS-4.2ALOGPS
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+189.88831661259
DarkChem[M-H]-194.25531661259
DeepCCS[M+H]+196.70530932474
DeepCCS[M-H]-194.8130932474
DeepCCS[M-2H]-228.05230932474
DeepCCS[M+Na]+202.44930932474
AllCCS[M+H]+195.332859911
AllCCS[M+H-H2O]+192.832859911
AllCCS[M+NH4]+197.732859911
AllCCS[M+Na]+198.332859911
AllCCS[M-H]-194.932859911
AllCCS[M+Na-2H]-196.332859911
AllCCS[M+HCOO]-197.932859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
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)=O4149.8Standard polar33892256
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)=O2531.9Standard non polar33892256
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)=O2759.3Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Prostaglandin G2,1TMS,isomer #1CCCCC[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)OO2751.9Semi standard non polar33892256
Prostaglandin G2,1TBDMS,isomer #1CCCCC[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)OO2968.8Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Prostaglandin G2 GC-MS (Non-derivatized) - 70eV, Positivesplash10-006x-5293000000-4f6f219630c974fad6842017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Prostaglandin G2 GC-MS (1 TMS) - 70eV, Positivesplash10-00gr-9142200000-12079cbb99c54d74b4e42017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Prostaglandin G2 GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Prostaglandin G2 GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prostaglandin G2 10V, Positive-QTOFsplash10-0udi-0119000000-06893304af83e030a39b2015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prostaglandin G2 20V, Positive-QTOFsplash10-0zmr-3369000000-b1d0f67eea930b11ae4c2015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prostaglandin G2 40V, Positive-QTOFsplash10-1003-9400000000-7fbd48d8b1a086fc44d22015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prostaglandin G2 10V, Negative-QTOFsplash10-014i-0019000000-4a1c6a9bb1b35fe201ef2015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prostaglandin G2 20V, Negative-QTOFsplash10-00r2-2149000000-16bc14c91731cdc795862015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prostaglandin G2 40V, Negative-QTOFsplash10-0a4i-9162000000-ad0929ccdcab78d69a992015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prostaglandin G2 10V, Positive-QTOFsplash10-0gb9-0009000000-7bd756fb66d8a2f4e9dd2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prostaglandin G2 20V, Positive-QTOFsplash10-014r-2069000000-0067297ea99f20c4e4ca2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prostaglandin G2 40V, Positive-QTOFsplash10-06ec-7920000000-d773a60db405a49448652021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prostaglandin G2 10V, Negative-QTOFsplash10-00lr-0009000000-a2da7230358a405653f82021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prostaglandin G2 20V, Negative-QTOFsplash10-00li-0029000000-c33c17a6864e28828b802021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prostaglandin G2 40V, Negative-QTOFsplash10-014j-3096000000-14b691a730b064b985832021-09-22Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane (predicted from logP)
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB03866
Phenol Explorer Compound IDNot Available
FooDB IDFDB023127
KNApSAcK IDNot Available
Chemspider ID4444406
KEGG Compound IDC05956
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkProstaglandin G2
METLIN ID3508
PubChem Compound5280883
PDB IDNot Available
ChEBI ID27647
Food Biomarker OntologyNot Available
VMH IDHC02217
MarkerDB IDNot Available
Good Scents IDNot Available
References
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 ]

Enzymes

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 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:
PTGS1
Uniprot ID:
P23219
Molecular weight:
68685.82
Reactions
Prostaglandin H2 + Acceptor + Water → Prostaglandin G2 + Reduced acceptordetails
Arachidonic acid + Oxygen → Prostaglandin G2details
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