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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2006-10-25 09:43:39 UTC
Update Date2022-03-07 02:49:25 UTC
HMDB IDHMDB0005077
Secondary Accession Numbers
  • HMDB05077
Metabolite Identification
Common Name8-iso-15-keto-PGF2a
Description8-iso-15-keto-PGF2alpha is an isoprostane. Isoprostanes are produced during peroxidation of membrane lipids by free radicals and reactive oxygen species, and are currently used as markers of many disease states and experimental conditions in which oxidative stress is a prominent feature. A small number of reports have described the ability of some isoprostanes to evoke important biological effects in smooth muscle and other cell types. There is a long (and growing) list of disease states and pathophysiological conditions which are associated with marked elevation in the levels of iso- prostanes. For example, measured levels of the plasma, urine, bronchoalveolar lavage fluid, and/or tissues of smokers, patients with asthma chronic obstructive pulmonary disease, interstitial lung disease, cystic fibrosis, or acute chest syndrome, during exposure to allergen, ozone or hyperoxia; and during ventilated ischemia. Likewise, cardiovascular conditions such as renal, myocardial, ischemia-reperfusion injury, atherosclerosis, and pre-eclampsia are also indicated by a marked elevation of plasma/urinary levels of isoprostanes. (PMID: 10930353 ).
Structure
Data?1582752344
Synonyms
ValueSource
(5Z,8b,9a,11a,13E)-9,11-Dihydroxy-15-oxo-prosta-5,13-dien-1-OateHMDB
(5Z,8b,9a,11a,13E)-9,11-Dihydroxy-15-oxo-prosta-5,13-dien-1-Oic acidHMDB
8-Iso-15-keto-PGF2alphaHMDB
9S,11R-Dihydroxy-15-oxo-5Z,13E-prostadienoateHMDB
9S,11R-Dihydroxy-15-oxo-5Z,13E-prostadienoic acidHMDB
9S,11R-Dihydroxy-15-oxo-5Z,13E-prostadienoic acid-cyclo[8S,12R]HMDB
8-Iso-15-keto-PGF2αHMDB
8-Iso-15-keto-PGF2aGenerator
Chemical FormulaC20H32O5
Average Molecular Weight352.4651
Monoisotopic Molecular Weight352.224974134
IUPAC Name(5Z)-7-[(1S,2R,3R,5S)-3,5-dihydroxy-2-[(1E)-3-oxooct-1-en-1-yl]cyclopentyl]hept-5-enoic acid
Traditional Name8-iso-15-keto-PGF2α
CAS Registry Number191919-01-4
SMILES
CCCCCC(=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/h4,7,12-13,16-19,22-23H,2-3,5-6,8-11,14H2,1H3,(H,24,25)/b7-4-,13-12+/t16-,17+,18-,19+/m0/s1
InChI KeyLOLJEILMPWPILA-RLXHZABYSA-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
  • Unsaturated fatty acid
  • Fatty acid
  • Enone
  • Acryloyl-group
  • Cyclic alcohol
  • Alpha,beta-unsaturated ketone
  • Secondary alcohol
  • Ketone
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organic oxide
  • Organic oxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External Descriptors
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 Solubility0.093 g/LALOGPS
logP3.03ALOGPS
logP3.02ChemAxon
logS-3.6ALOGPS
pKa (Strongest Acidic)4.36ChemAxon
pKa (Strongest Basic)-2.9ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area94.83 ŲChemAxon
Rotatable Bond Count12ChemAxon
Refractivity99.57 m³·mol⁻¹ChemAxon
Polarizability40.77 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
DeepCCS[M+H]+199.52230932474
DeepCCS[M-H]-197.12630932474
DeepCCS[M-2H]-230.82630932474
DeepCCS[M+Na]+205.7530932474
AllCCS[M+H]+192.632859911
AllCCS[M+H-H2O]+189.932859911
AllCCS[M+NH4]+195.032859911
AllCCS[M+Na]+195.732859911
AllCCS[M-H]-191.132859911
AllCCS[M+Na-2H]-192.532859911
AllCCS[M+HCOO]-194.132859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
8-iso-15-keto-PGF2aCCCCCC(=O)\C=C\[C@H]1[C@H](O)C[C@H](O)[C@H]1C\C=C/CCCC(O)=O4596.6Standard polar33892256
8-iso-15-keto-PGF2aCCCCCC(=O)\C=C\[C@H]1[C@H](O)C[C@H](O)[C@H]1C\C=C/CCCC(O)=O2639.5Standard non polar33892256
8-iso-15-keto-PGF2aCCCCCC(=O)\C=C\[C@H]1[C@H](O)C[C@H](O)[C@H]1C\C=C/CCCC(O)=O2948.9Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
8-iso-15-keto-PGF2a,1TMS,isomer #1CCCCCC(=O)/C=C/[C@@H]1[C@H](C/C=C\CCCC(=O)O)[C@@H](O)C[C@H]1O[Si](C)(C)C2758.3Semi standard non polar33892256
8-iso-15-keto-PGF2a,1TMS,isomer #2CCCCCC(=O)/C=C/[C@@H]1[C@H](C/C=C\CCCC(=O)O)[C@@H](O[Si](C)(C)C)C[C@H]1O2753.6Semi standard non polar33892256
8-iso-15-keto-PGF2a,1TMS,isomer #3CCCCCC(=O)/C=C/[C@@H]1[C@H](C/C=C\CCCC(=O)O[Si](C)(C)C)[C@@H](O)C[C@H]1O2839.3Semi standard non polar33892256
8-iso-15-keto-PGF2a,1TMS,isomer #4CCCCC=C(/C=C/[C@@H]1[C@H](C/C=C\CCCC(=O)O)[C@@H](O)C[C@H]1O)O[Si](C)(C)C3159.9Semi standard non polar33892256
8-iso-15-keto-PGF2a,2TMS,isomer #1CCCCCC(=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)C2724.7Semi standard non polar33892256
8-iso-15-keto-PGF2a,2TMS,isomer #2CCCCCC(=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)C2700.5Semi standard non polar33892256
8-iso-15-keto-PGF2a,2TMS,isomer #3CCCCC=C(/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)C3046.3Semi standard non polar33892256
8-iso-15-keto-PGF2a,2TMS,isomer #4CCCCCC(=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]1O2726.2Semi standard non polar33892256
8-iso-15-keto-PGF2a,2TMS,isomer #5CCCCC=C(/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)C3034.3Semi standard non polar33892256
8-iso-15-keto-PGF2a,2TMS,isomer #6CCCCC=C(/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)C3078.6Semi standard non polar33892256
8-iso-15-keto-PGF2a,3TMS,isomer #1CCCCCC(=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)C2696.6Semi standard non polar33892256
8-iso-15-keto-PGF2a,3TMS,isomer #2CCCCC=C(/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)C2998.7Semi standard non polar33892256
8-iso-15-keto-PGF2a,3TMS,isomer #3CCCCC=C(/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)C3006.4Semi standard non polar33892256
8-iso-15-keto-PGF2a,3TMS,isomer #4CCCCC=C(/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)C2984.9Semi standard non polar33892256
8-iso-15-keto-PGF2a,4TMS,isomer #1CCCCC=C(/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)C2964.5Semi standard non polar33892256
8-iso-15-keto-PGF2a,4TMS,isomer #1CCCCC=C(/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)C2751.3Standard non polar33892256
8-iso-15-keto-PGF2a,4TMS,isomer #1CCCCC=C(/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)C2956.4Standard polar33892256
8-iso-15-keto-PGF2a,1TBDMS,isomer #1CCCCCC(=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)C2984.7Semi standard non polar33892256
8-iso-15-keto-PGF2a,1TBDMS,isomer #2CCCCCC(=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]1O2985.2Semi standard non polar33892256
8-iso-15-keto-PGF2a,1TBDMS,isomer #3CCCCCC(=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]1O3113.6Semi standard non polar33892256
8-iso-15-keto-PGF2a,1TBDMS,isomer #4CCCCC=C(/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)C3400.4Semi standard non polar33892256
8-iso-15-keto-PGF2a,2TBDMS,isomer #1CCCCCC(=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)C3225.6Semi standard non polar33892256
8-iso-15-keto-PGF2a,2TBDMS,isomer #2CCCCCC(=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)C3185.1Semi standard non polar33892256
8-iso-15-keto-PGF2a,2TBDMS,isomer #3CCCCC=C(/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)C3480.8Semi standard non polar33892256
8-iso-15-keto-PGF2a,2TBDMS,isomer #4CCCCCC(=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]1O3225.2Semi standard non polar33892256
8-iso-15-keto-PGF2a,2TBDMS,isomer #5CCCCC=C(/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)C3478.3Semi standard non polar33892256
8-iso-15-keto-PGF2a,2TBDMS,isomer #6CCCCC=C(/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)C3568.2Semi standard non polar33892256
8-iso-15-keto-PGF2a,3TBDMS,isomer #1CCCCCC(=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)C3401.9Semi standard non polar33892256
8-iso-15-keto-PGF2a,3TBDMS,isomer #2CCCCC=C(/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)C3701.3Semi standard non polar33892256
8-iso-15-keto-PGF2a,3TBDMS,isomer #3CCCCC=C(/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)C3647.7Semi standard non polar33892256
8-iso-15-keto-PGF2a,3TBDMS,isomer #4CCCCC=C(/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)C3690.8Semi standard non polar33892256
8-iso-15-keto-PGF2a,4TBDMS,isomer #1CCCCC=C(/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)C3844.9Semi standard non polar33892256
8-iso-15-keto-PGF2a,4TBDMS,isomer #1CCCCC=C(/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)C3447.5Standard non polar33892256
8-iso-15-keto-PGF2a,4TBDMS,isomer #1CCCCC=C(/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)C3218.3Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 8-iso-15-keto-PGF2a GC-MS (Non-derivatized) - 70eV, Positivesplash10-0570-4498000000-cc0a6152c4c014df4b6f2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 8-iso-15-keto-PGF2a GC-MS (3 TMS) - 70eV, Positivesplash10-0udi-5100980000-6257b72a2aa9de720f362017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 8-iso-15-keto-PGF2a 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-15-keto-PGF2a 10V, Positive-QTOFsplash10-00kr-0019000000-910369cab5e253b484e62017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8-iso-15-keto-PGF2a 20V, Positive-QTOFsplash10-00kr-2295000000-e2c04166a9405e56f2fc2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8-iso-15-keto-PGF2a 40V, Positive-QTOFsplash10-00dr-9160000000-23fb78d0cc03202e32122017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8-iso-15-keto-PGF2a 10V, Negative-QTOFsplash10-0ue9-0009000000-e05daa9da0040142e39c2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8-iso-15-keto-PGF2a 20V, Negative-QTOFsplash10-0f8i-2069000000-8c098522c3791b504d192017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8-iso-15-keto-PGF2a 40V, Negative-QTOFsplash10-0a4i-9441000000-d1759dfb65fcc9f9b4702017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8-iso-15-keto-PGF2a 10V, Negative-QTOFsplash10-0udi-0039000000-db45ea43b0b32962d5432021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8-iso-15-keto-PGF2a 20V, Negative-QTOFsplash10-0fri-0094000000-e560b2602cb2e45b3c662021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8-iso-15-keto-PGF2a 40V, Negative-QTOFsplash10-052p-9151000000-c46a461dbc0a557352d52021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8-iso-15-keto-PGF2a 10V, Positive-QTOFsplash10-014r-0019000000-e81e2e2f5abdc4bb9c392021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8-iso-15-keto-PGF2a 20V, Positive-QTOFsplash10-014r-9356000000-a519ec47287e412b92ed2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8-iso-15-keto-PGF2a 40V, Positive-QTOFsplash10-00kf-9100000000-fb5ea9c2e3392b9c60142021-09-24Wishart 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 IDFDB023618
KNApSAcK IDNot Available
Chemspider ID4446336
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5283215
PDB IDNot Available
ChEBI IDNot Available
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. Janssen LJ: Isoprostanes: generation, pharmacology, and roles in free-radical-mediated effects in the lung. Pulm Pharmacol Ther. 2000;13(4):149-55. [PubMed:10930353 ]