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Human Metabolome Database Version 3.5

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Showing metabocard for Prostaglandin G2 (HMDB03235)

Record Information
Version 3.5
Creation Date 2006-05-22 09:12:43 -0600
Update Date 2013-02-08 17:12:22 -0700
HMDB ID HMDB03235
Secondary Accession Numbers
  • 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 Link_out, 16552393 Link_out, 16411757 Link_out). 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.
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. (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
  2. (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
  3. 9,11-Epidioxy-15-hydroperoxy-Prosta-5,13-dien-1-oate
  4. 9,11-Epidioxy-15-hydroperoxy-Prosta-5,13-dien-1-oic acid
  5. 9S,11R-Epidioxy-15S-hydroperoxy-5Z,13E-prostadienoate
  6. 9S,11R-Epidioxy-15S-hydroperoxy-5Z,13E-prostadienoic acid
  7. Endoperoxide G2
  8. PGG2
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 IUPAC Name prostaglandin G2
CAS Registry Number 51982-36-6
SMILES [H][C@@]12C[C@@]([H])(OO1)[C@H](\C=C\[C@H](CCCCC)OO)[C@H]2C\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
Kingdom Organic Compounds
Super Class Lipids
Class Eicosanoids
Sub Class Prostaglandins and related compounds
Other Descriptors
  • Aliphatic Heteropolycyclic Compounds
  • Heterocyclic Fatty Acids
  • Hydroperoxy Fatty Acids
  • Organic Compounds
  • Unsaturated Fatty Acids
Substituents
  • Carboxylic Acid
  • Hydroperoxide
  • Ortho Dioxane
  • Ortho Dioxolane
Direct Parent Prostaglandins and related compounds
Ontology
Status Expected and Not Quantified
Origin
  • Endogenous
  • Food
Biofunction
  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane integrity/stability
Application
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Extracellular
  • Membrane (predicted from logP)
Physical Properties
State Solid
Experimental 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
Predicted Properties
Property Value Source
Water Solubility 0.026 g/L ALOGPS
LogP 4.31 ALOGPS
LogP 4.41 ChemAxon
LogS -4.15 ALOGPS
pKa (strongest acidic) 4.36 ChemAxon
pKa (strongest basic) -4.2 ChemAxon
Hydrogen Acceptor Count 6 ChemAxon
Hydrogen Donor Count 2 ChemAxon
Polar Surface Area 85.22 A2 ChemAxon
Rotatable Bond Count 13 ChemAxon
Refractivity 99.39 ChemAxon
Polarizability 40.2 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge -1 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane (predicted from logP)
Biofluid Locations Not Available
Tissue Location Not Available
Pathways
Name SMPDB Link KEGG Link
Arachidonic Acid Metabolism SMP00075 map00590 Link_out
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB023127
KNApSAcK ID Not Available
Chemspider ID 4444406 Link_out
KEGG Compound ID C05956 Link_out
BioCyc ID Not Available
BiGG ID Not Available
Wikipedia Link Not Available
NuGOwiki Link HMDB03235 Link_out
Metagene Link HMDB03235 Link_out
METLIN ID 3508 Link_out
PubChem Compound 5280883 Link_out
PDB ID PGX Link_out
ChEBI ID 27647 Link_out
References
Synthesis Reference Not 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 Link_out
Enzymes
Name: Prostaglandin G/H synthase 2
Reactions:
  • arachidonate + AH2 + 2 O2 = prostaglandin H2 + A + H2O [RN:R01599]
Gene Name: PTGS2
Uniprot ID: P35354 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Prostaglandin G/H synthase 1
Reactions:
  • arachidonate + AH2 + 2 O2 = prostaglandin H2 + A + H2O [RN:R01599]
Gene Name: PTGS1
Uniprot ID: P23219 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA