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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2006-05-22 14:17:37 UTC
Update Date2022-03-07 02:49:13 UTC
HMDB IDHMDB0002132
Secondary Accession Numbers
  • HMDB02132
Metabolite Identification
Common Name8-iso-PGF3a
Description8-iso-PGF3alpha is an isoprostane with an antiaggregatory action in human blood. Isoprostanes (IsoPs) are formed in vivo from the free radical-catalyzed peroxidation of arachidonate independent of cyclooxygenase (COX). Although the structures of these compounds are very similar to COX-derived prostaglandins (PGs), an important distinction between IsoPs and PGs is that IsoP bicycloendoperoxide intermediates contain side chains that are predominantly (>90%) oriented cis in relation to the prostane ring because the generation of these intermediates is favored kinetically. In contrast to other types of prostanoids, E2/D2-IsoPs are beta-hydroxyketone-containing compounds that can undergo reversible keto-enol tautomerization under both acidic and basic conditions, allowing rearrangement of the side chains that are initially cis to the more stable trans-configuration. (PMID: 12746435 ).
Structure
Data?1582752231
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
Not AvailableNot 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 Solubility0.11 g/LALOGPS
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 RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+189.22831661259
DarkChem[M-H]-183.64931661259
DeepCCS[M+H]+198.58730932474
DeepCCS[M-H]-196.19130932474
DeepCCS[M-2H]-229.60830932474
DeepCCS[M+Na]+204.49930932474
AllCCS[M+H]+193.132859911
AllCCS[M+H-H2O]+190.432859911
AllCCS[M+NH4]+195.632859911
AllCCS[M+Na]+196.332859911
AllCCS[M-H]-190.432859911
AllCCS[M+Na-2H]-191.832859911
AllCCS[M+HCOO]-193.532859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
8-iso-PGF3aCC\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)=O4597.6Standard polar33892256
8-iso-PGF3aCC\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)=O2704.3Standard non polar33892256
8-iso-PGF3aCC\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)=O2970.8Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
8-iso-PGF3a,1TMS,isomer #1CC/C=C\C[C@@H](/C=C/[C@@H]1[C@H](C/C=C\CCCC(=O)O)[C@@H](O)C[C@H]1O)O[Si](C)(C)C2931.6Semi standard non polar33892256
8-iso-PGF3a,1TMS,isomer #2CC/C=C\C[C@H](O)/C=C/[C@@H]1[C@H](C/C=C\CCCC(=O)O)[C@@H](O)C[C@H]1O[Si](C)(C)C2826.6Semi standard non polar33892256
8-iso-PGF3a,1TMS,isomer #3CC/C=C\C[C@H](O)/C=C/[C@@H]1[C@H](C/C=C\CCCC(=O)O)[C@@H](O[Si](C)(C)C)C[C@H]1O2807.9Semi standard non polar33892256
8-iso-PGF3a,1TMS,isomer #4CC/C=C\C[C@H](O)/C=C/[C@@H]1[C@H](C/C=C\CCCC(=O)O[Si](C)(C)C)[C@@H](O)C[C@H]1O2827.7Semi standard non polar33892256
8-iso-PGF3a,2TMS,isomer #1CC/C=C\C[C@@H](/C=C/[C@@H]1[C@H](C/C=C\CCCC(=O)O[Si](C)(C)C)[C@@H](O)C[C@H]1O)O[Si](C)(C)C2844.7Semi standard non polar33892256
8-iso-PGF3a,2TMS,isomer #2CC/C=C\C[C@@H](/C=C/[C@@H]1[C@H](C/C=C\CCCC(=O)O)[C@@H](O[Si](C)(C)C)C[C@H]1O)O[Si](C)(C)C2783.8Semi standard non polar33892256
8-iso-PGF3a,2TMS,isomer #3CC/C=C\C[C@@H](/C=C/[C@@H]1[C@H](C/C=C\CCCC(=O)O)[C@@H](O)C[C@H]1O[Si](C)(C)C)O[Si](C)(C)C2798.6Semi standard non polar33892256
8-iso-PGF3a,2TMS,isomer #4CC/C=C\C[C@H](O)/C=C/[C@@H]1[C@H](C/C=C\CCCC(=O)O[Si](C)(C)C)[C@@H](O)C[C@H]1O[Si](C)(C)C2772.3Semi standard non polar33892256
8-iso-PGF3a,2TMS,isomer #5CC/C=C\C[C@H](O)/C=C/[C@@H]1[C@H](C/C=C\CCCC(=O)O)[C@@H](O[Si](C)(C)C)C[C@H]1O[Si](C)(C)C2777.9Semi standard non polar33892256
8-iso-PGF3a,2TMS,isomer #6CC/C=C\C[C@H](O)/C=C/[C@@H]1[C@H](C/C=C\CCCC(=O)O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)C[C@H]1O2753.0Semi standard non polar33892256
8-iso-PGF3a,3TMS,isomer #1CC/C=C\C[C@@H](/C=C/[C@@H]1[C@H](C/C=C\CCCC(=O)O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)C[C@H]1O)O[Si](C)(C)C2741.9Semi standard non polar33892256
8-iso-PGF3a,3TMS,isomer #2CC/C=C\C[C@@H](/C=C/[C@@H]1[C@H](C/C=C\CCCC(=O)O[Si](C)(C)C)[C@@H](O)C[C@H]1O[Si](C)(C)C)O[Si](C)(C)C2760.9Semi standard non polar33892256
8-iso-PGF3a,3TMS,isomer #3CC/C=C\C[C@@H](/C=C/[C@@H]1[C@H](C/C=C\CCCC(=O)O)[C@@H](O[Si](C)(C)C)C[C@H]1O[Si](C)(C)C)O[Si](C)(C)C2736.7Semi standard non polar33892256
8-iso-PGF3a,3TMS,isomer #4CC/C=C\C[C@H](O)/C=C/[C@@H]1[C@H](C/C=C\CCCC(=O)O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)C[C@H]1O[Si](C)(C)C2739.7Semi standard non polar33892256
8-iso-PGF3a,4TMS,isomer #1CC/C=C\C[C@@H](/C=C/[C@@H]1[C@H](C/C=C\CCCC(=O)O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)C[C@H]1O[Si](C)(C)C)O[Si](C)(C)C2750.1Semi standard non polar33892256
8-iso-PGF3a,1TBDMS,isomer #1CC/C=C\C[C@@H](/C=C/[C@@H]1[C@H](C/C=C\CCCC(=O)O)[C@@H](O)C[C@H]1O)O[Si](C)(C)C(C)(C)C3179.6Semi standard non polar33892256
8-iso-PGF3a,1TBDMS,isomer #2CC/C=C\C[C@H](O)/C=C/[C@@H]1[C@H](C/C=C\CCCC(=O)O)[C@@H](O)C[C@H]1O[Si](C)(C)C(C)(C)C3046.5Semi standard non polar33892256
8-iso-PGF3a,1TBDMS,isomer #3CC/C=C\C[C@H](O)/C=C/[C@@H]1[C@H](C/C=C\CCCC(=O)O)[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H]1O3026.2Semi standard non polar33892256
8-iso-PGF3a,1TBDMS,isomer #4CC/C=C\C[C@H](O)/C=C/[C@@H]1[C@H](C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C)[C@@H](O)C[C@H]1O3097.2Semi standard non polar33892256
8-iso-PGF3a,2TBDMS,isomer #1CC/C=C\C[C@@H](/C=C/[C@@H]1[C@H](C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C)[C@@H](O)C[C@H]1O)O[Si](C)(C)C(C)(C)C3367.5Semi standard non polar33892256
8-iso-PGF3a,2TBDMS,isomer #2CC/C=C\C[C@@H](/C=C/[C@@H]1[C@H](C/C=C\CCCC(=O)O)[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H]1O)O[Si](C)(C)C(C)(C)C3255.7Semi standard non polar33892256
8-iso-PGF3a,2TBDMS,isomer #3CC/C=C\C[C@@H](/C=C/[C@@H]1[C@H](C/C=C\CCCC(=O)O)[C@@H](O)C[C@H]1O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3264.5Semi standard non polar33892256
8-iso-PGF3a,2TBDMS,isomer #4CC/C=C\C[C@H](O)/C=C/[C@@H]1[C@H](C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C)[C@@H](O)C[C@H]1O[Si](C)(C)C(C)(C)C3258.1Semi standard non polar33892256
8-iso-PGF3a,2TBDMS,isomer #5CC/C=C\C[C@H](O)/C=C/[C@@H]1[C@H](C/C=C\CCCC(=O)O)[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H]1O[Si](C)(C)C(C)(C)C3228.5Semi standard non polar33892256
8-iso-PGF3a,2TBDMS,isomer #6CC/C=C\C[C@H](O)/C=C/[C@@H]1[C@H](C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H]1O3240.2Semi standard non polar33892256
8-iso-PGF3a,3TBDMS,isomer #1CC/C=C\C[C@@H](/C=C/[C@@H]1[C@H](C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H]1O)O[Si](C)(C)C(C)(C)C3474.3Semi standard non polar33892256
8-iso-PGF3a,3TBDMS,isomer #2CC/C=C\C[C@@H](/C=C/[C@@H]1[C@H](C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C)[C@@H](O)C[C@H]1O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3487.0Semi standard non polar33892256
8-iso-PGF3a,3TBDMS,isomer #3CC/C=C\C[C@@H](/C=C/[C@@H]1[C@H](C/C=C\CCCC(=O)O)[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H]1O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3440.9Semi standard non polar33892256
8-iso-PGF3a,3TBDMS,isomer #4CC/C=C\C[C@H](O)/C=C/[C@@H]1[C@H](C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H]1O[Si](C)(C)C(C)(C)C3454.8Semi standard non polar33892256
8-iso-PGF3a,4TBDMS,isomer #1CC/C=C\C[C@@H](/C=C/[C@@H]1[C@H](C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H]1O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3625.5Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 8-iso-PGF3a GC-MS (Non-derivatized) - 70eV, Positivesplash10-0690-5569000000-b6d9924bb1e1598b9d722017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 8-iso-PGF3a GC-MS (4 TMS) - 70eV, Positivesplash10-004i-6100298000-cefdc46b7ca2307e3bfd2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 8-iso-PGF3a 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 - 8-iso-PGF3a 10V, Positive-QTOFsplash10-014r-0019000000-f98b94189569251d37a22017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8-iso-PGF3a 20V, Positive-QTOFsplash10-014r-3197000000-85761caed143126a09742017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8-iso-PGF3a 40V, Positive-QTOFsplash10-01bi-9170000000-9c3f2455a6d592ea0a4a2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8-iso-PGF3a 10V, Negative-QTOFsplash10-0ue9-0009000000-3b5070d3e2790d2cb20f2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8-iso-PGF3a 20V, Negative-QTOFsplash10-001i-1039000000-d00dd3f608a0e190f4582017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8-iso-PGF3a 40V, Negative-QTOFsplash10-0a4i-9631000000-10bc983babf0367498412017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8-iso-PGF3a 10V, Negative-QTOFsplash10-0uxr-0009000000-33af08865c9568c21f7a2021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8-iso-PGF3a 20V, Negative-QTOFsplash10-0fs9-0097000000-18f214d33dfa137da4322021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8-iso-PGF3a 40V, Negative-QTOFsplash10-007y-9162000000-31a96bbf479dad16df6e2021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8-iso-PGF3a 10V, Positive-QTOFsplash10-014r-0019000000-40e30046291432c91b562021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8-iso-PGF3a 20V, Positive-QTOFsplash10-014i-9276000000-4e19df362ec1af060bb22021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8-iso-PGF3a 40V, Positive-QTOFsplash10-014l-9300000000-ba6ae7b1d6d0d6589c1f2021-09-25Wishart 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 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
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents 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 References
  1. Gao L, Zackert WE, Hasford JJ, Danekis ME, Milne GL, Remmert C, Reese J, Yin H, Tai HH, Dey SK, Porter NA, Morrow JD: Formation of prostaglandins E2 and D2 via the isoprostane pathway: a mechanism for the generation of bioactive prostaglandins independent of cyclooxygenase. J Biol Chem. 2003 Aug 1;278(31):28479-89. Epub 2003 May 13. [PubMed:12746435 ]