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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2009-07-25 00:12:08 UTC
Update Date2022-03-07 02:51:28 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
Data?1582753086
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
Physiological effectNot Available
Disposition
ProcessNot Available
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 PropertiesNot Available
Predicted Molecular 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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+197.45130932474
DeepCCS[M-H]-195.05530932474
DeepCCS[M-2H]-228.32830932474
DeepCCS[M+Na]+203.36330932474
AllCCS[M+H]+191.932859911
AllCCS[M+H-H2O]+189.132859911
AllCCS[M+NH4]+194.432859911
AllCCS[M+Na]+195.132859911
AllCCS[M-H]-191.432859911
AllCCS[M+Na-2H]-192.632859911
AllCCS[M+HCOO]-194.032859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Prostaglandin H3CC\C=C/C[C@H](O)\C=C\[C@H]1[C@H]2C[C@H](OO2)[C@@H]1C\C=C/CCCC(O)=O4243.7Standard polar33892256
Prostaglandin H3CC\C=C/C[C@H](O)\C=C\[C@H]1[C@H]2C[C@H](OO2)[C@@H]1C\C=C/CCCC(O)=O2512.4Standard non polar33892256
Prostaglandin H3CC\C=C/C[C@H](O)\C=C\[C@H]1[C@H]2C[C@H](OO2)[C@@H]1C\C=C/CCCC(O)=O2730.0Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Prostaglandin H3,1TMS,isomer #1CC/C=C\C[C@@H](/C=C/[C@H]1[C@H]2C[C@H](OO2)[C@@H]1C/C=C\CCCC(=O)O)O[Si](C)(C)C2752.7Semi standard non polar33892256
Prostaglandin H3,1TMS,isomer #2CC/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[Si](C)(C)C2688.3Semi standard non polar33892256
Prostaglandin H3,2TMS,isomer #1CC/C=C\C[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)O[Si](C)(C)C2733.0Semi standard non polar33892256
Prostaglandin H3,1TBDMS,isomer #1CC/C=C\C[C@@H](/C=C/[C@H]1[C@H]2C[C@H](OO2)[C@@H]1C/C=C\CCCC(=O)O)O[Si](C)(C)C(C)(C)C2946.3Semi standard non polar33892256
Prostaglandin H3,1TBDMS,isomer #2CC/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[Si](C)(C)C(C)(C)C2911.0Semi standard non polar33892256
Prostaglandin H3,2TBDMS,isomer #1CC/C=C\C[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)O[Si](C)(C)C(C)(C)C3180.5Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Prostaglandin H3 GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Prostaglandin H3 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 H3 10V, Positive-QTOFsplash10-001i-0019000000-77e67e33d78d860c2b692018-11-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prostaglandin H3 20V, Positive-QTOFsplash10-067r-5197000000-a340b5689ff35749ead62018-11-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prostaglandin H3 40V, Positive-QTOFsplash10-00kr-9300000000-3f5fdbb50eb4e2f4786e2018-11-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prostaglandin H3 10V, Positive-QTOFsplash10-0159-0019000000-15c30c1364eb62a11cdc2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prostaglandin H3 20V, Positive-QTOFsplash10-0159-3294000000-c385acec093995b9b2cc2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prostaglandin H3 40V, Positive-QTOFsplash10-014l-9700000000-953ce8ec5b904f32214e2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prostaglandin H3 10V, Negative-QTOFsplash10-000t-0009000000-d5a90b83be9f7c55e5382021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prostaglandin H3 20V, Negative-QTOFsplash10-014i-0039000000-9792e0648327259104ce2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prostaglandin H3 40V, Negative-QTOFsplash10-001i-5293000000-1bd1d88436ef3645370f2021-09-22Wishart LabView Spectrum
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
FooDB 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
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
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.