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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2009-07-25 00:12:08 UTC
Update Date2018-05-17 16:01:21 UTC
HMDB IDHMDB0013040
Secondary Accession Numbers
  • HMDB13040
Metabolite Identification
Common NameProstaglandin H3
DescriptionProstaglandin H3 (PGH3) can be enzymatically converted by platelets into thromboxane A3 (TXA3). Both prostaglandin H2 (PGH2) and thromboxane A2 (TXA2) aggregate human platelet-rich plasma. In contrast, PGH3 and TXA3 do not. PGH3 and TXA3 increase platelet cyclic AMP in platelet-rich plasma and thereby (1) inhibit aggregation by other agonists, (2) block the ADP-induced release reaction, and (3) suppress platelet phospholipase-A2 activity or events leading to its activation. PGI3 (A'7-prostacyclin; synthesized from PGH3 by blood vessel enzyme) and PGI2 (prostacyclin) exert similar effects. Both compounds are potent coronary relaxants that also inhibit aggregation in human platelet-rich plasma and increase platelet adenylate cyclase activity. 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.
Structure
Thumb
Synonyms
ValueSource
(5Z,9alpha,11alpha,13E,15S,17Z)-9,11-Epidioxy-15-hydroxyprosta-5,13,17-trien-1-Oic acidChEBI
(5Z,9S,11R,13E,15S,17Z)-15-Hydroxy-9,11-epidioxyprosta-5,13,17-trienoic acidChEBI
PGH3ChEBI
(5Z,9a,11a,13E,15S,17Z)-9,11-Epidioxy-15-hydroxyprosta-5,13,17-trien-1-OateGenerator
(5Z,9a,11a,13E,15S,17Z)-9,11-Epidioxy-15-hydroxyprosta-5,13,17-trien-1-Oic acidGenerator
(5Z,9alpha,11alpha,13E,15S,17Z)-9,11-Epidioxy-15-hydroxyprosta-5,13,17-trien-1-OateGenerator
(5Z,9Α,11α,13E,15S,17Z)-9,11-epidioxy-15-hydroxyprosta-5,13,17-trien-1-OateGenerator
(5Z,9Α,11α,13E,15S,17Z)-9,11-epidioxy-15-hydroxyprosta-5,13,17-trien-1-Oic acidGenerator
(5Z,9S,11R,13E,15S,17Z)-15-Hydroxy-9,11-epidioxyprosta-5,13,17-trienoateGenerator
Chemical FormulaC20H30O5
Average Molecular Weight350.455
Monoisotopic Molecular Weight350.209324066
IUPAC Name(5Z)-7-[(1R,4S,5R,6R)-6-[(1E,3S,5Z)-3-hydroxyocta-1,5-dien-1-yl]-2,3-dioxabicyclo[2.2.1]heptan-5-yl]hept-5-enoic acid
Traditional Name(5Z)-7-[(1R,4S,5R,6R)-6-[(1E,3S,5Z)-3-hydroxyocta-1,5-dien-1-yl]-2,3-dioxabicyclo[2.2.1]heptan-5-yl]hept-5-enoic acid
CAS Registry Number60114-66-1
SMILES
CC\C=C/C[C@H](O)\C=C\[C@H]1[C@H]2C[C@H](OO2)[C@@H]1C\C=C/CCCC(O)=O
InChI Identifier
InChI=1S/C20H30O5/c1-2-3-6-9-15(21)12-13-17-16(18-14-19(17)25-24-18)10-7-4-5-8-11-20(22)23/h3-4,6-7,12-13,15-19,21H,2,5,8-11,14H2,1H3,(H,22,23)/b6-3-,7-4-,13-12+/t15-,16+,17+,18-,19+/m0/s1
InChI KeyPVTQTOGPOPGQGE-SAMSIYEGSA-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
  • 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 DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.041 g/LALOGPS
logP4.22ALOGPS
logP3.6ChemAxon
logS-3.9ALOGPS
pKa (Strongest Acidic)4.36ChemAxon
pKa (Strongest Basic)-1.7ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area75.99 ŲChemAxon
Rotatable Bond Count11ChemAxon
Refractivity99.16 m³·mol⁻¹ChemAxon
Polarizability38.71 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
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 IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB029265
KNApSAcK IDNot Available
Chemspider ID52085727
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound101600091
PDB IDNot Available
ChEBI ID134407
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  2. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  3. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  4. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  5. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.