Showing metabocard for 8-iso-PGF3a (BMDB0002132)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 22:51:31 UTC
Update Date2020-04-22 15:09:50 UTC
BMDB IDBMDB0002132
Secondary Accession Numbers
  • BMDB02132
Metabolite Identification
Common Name8-iso-PGF3a
Description8-iso-PGF3a, also known as 8-iso-PGF3alpha or 8-iso-PGF3α, 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. Thus, 8-iso-PGF3a is considered to be an eicosanoid. Based on a literature review very few articles have been published on 8-iso-PGF3a.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(5Z,8b,9a,11a,13E,15S,17Z)-9,11,15-Trihydroxy-prosta-5,13,17-trien-1-OateHMDB
(5Z,8b,9a,11a,13E,15S,17Z)-9,11,15-Trihydroxy-prosta-5,13,17-trien-1-Oic acidHMDB
7-[3a,5a-Dihydroxy-2-(3-hydroxy-1,5-octadienyl)cyclopentyl]-5-heptenoateHMDB
7-[3a,5a-Dihydroxy-2-(3-hydroxy-1,5-octadienyl)cyclopentyl]-5-heptenoic acidHMDB
8-Iso-PGF3alphaHMDB
9S,11R,15S-Trihydroxy-5Z,13E,17Z-prostatrienoateHMDB
9S,11R,15S-Trihydroxy-5Z,13E,17Z-prostatrienoic acidHMDB
9S,11R,15S-Trihydroxy-5Z,13E,17Z-prostatrienoic acid-cyclo[8S,12R]HMDB
8-Iso-PGF3αHMDB
8-Iso-PGF3aGenerator
Chemical FormulaC20H32O5
Average Molecular Weight352.4651
Monoisotopic Molecular Weight352.224974134
IUPAC Name(5Z)-7-[(1S,2R,3R,5S)-3,5-dihydroxy-2-[(1E,3S,5Z)-3-hydroxyocta-1,5-dien-1-yl]cyclopentyl]hept-5-enoic acid
Traditional Name8-iso-PGF3α
CAS Registry Number7045-31-0
SMILES
CC\C=C/C[C@H](O)\C=C\[C@H]1[C@H](O)C[C@H](O)[C@H]1C\C=C/CCCC(O)=O
InChI Identifier
InChI=1S/C20H32O5/c1-2-3-6-9-15(21)12-13-17-16(18(22)14-19(17)23)10-7-4-5-8-11-20(24)25/h3-4,6-7,12-13,15-19,21-23H,2,5,8-11,14H2,1H3,(H,24,25)/b6-3-,7-4-,13-12+/t15-,16-,17+,18-,19+/m0/s1
InChI KeySAKGBZWJAIABSY-PJCXKLBTSA-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
  • Hydroxy fatty acid
  • Cyclopentanol
  • Fatty acid
  • Unsaturated fatty acid
  • Cyclic alcohol
  • Secondary alcohol
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organic oxide
  • Organic oxygen compound
  • Alcohol
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cell membrane
  • Cytoplasm
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP3.7ALOGPS
logP2.25ChemAxon
logS-3.5ALOGPS
pKa (Strongest Acidic)4.36ChemAxon
pKa (Strongest Basic)-1.7ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area97.99 ŲChemAxon
Rotatable Bond Count11ChemAxon
Refractivity101.59 m³·mol⁻¹ChemAxon
Polarizability40.35 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0690-5569000000-b6d9924bb1e1598b9d72View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positivesplash10-004i-6100298000-cefdc46b7ca2307e3bfdView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014r-0019000000-f98b94189569251d37a2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014r-3197000000-85761caed143126a0974View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01bi-9170000000-9c3f2455a6d592ea0a4aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0ue9-0009000000-3b5070d3e2790d2cb20fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-1039000000-d00dd3f608a0e190f458View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9631000000-10bc983babf036749841View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0uxr-0009000000-33af08865c9568c21f7aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0fs9-0097000000-18f214d33dfa137da432View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-007y-9162000000-31a96bbf479dad16df6eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014r-0019000000-40e30046291432c91b56View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-9276000000-4e19df362ec1af060bb2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014l-9300000000-ba6ae7b1d6d0d6589c1fView in MoNA
Biological Properties
Cellular Locations
  • Cell membrane
  • Cytoplasm
  • Membrane
Biospecimen LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDHMDB0002132
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022859
KNApSAcK IDNot Available
Chemspider ID4446338
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5283217
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceBeal, Philip F., III; Fonken, Gunther S.; Pike, John E. Microbiological conversions of unsaturated fatty acids. (1965), 34 pp. BE 659984 19650819 CAN 64:87998 AN 1966:87998
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available