Record Information
Version1.0
Creation date2011-09-21 00:29:15 UTC
Update date2015-07-21 06:57:41 UTC
Primary IDFDB023392
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name8-Isoprostane
Description8-isoprostane concentrations are elevated in asthma and increase with the clinical severity and during acute asthma episodes. Isoprostane is formed in the airways of asthmatic patients from peroxidation of poly-unsaturated fatty acids in cell membranes, the effect of reactive oxygen species resulting of the NADPH oxidase of eosinophils, neutrophils and alveolar macrophages, which produces superoxide anion which undergoes dismutation to H2O2. (PMID 16354413) 8-isoprostane is also elevated in Bronchopulmonary dysplasia, which remains an important cause of morbidity and mortality in extremely premature newborn infants receiving intensive care and is the most common contributing factor to severe respiratory morbidity and mortality in early childhood. (PMID 14980283) 8-Isoprostaglandin F(2a) is a marker of oxidative stress in the aqueous humour of patients with exfoliation syndrome (XFS) (PubMed ID 12598453) [HMDB]
CAS Number155976-51-5
Structure
Thumb
Synonyms
SynonymSource
(1R,2S)-1-Heptyl-2-octylcyclopentaneChEBI
(8beta)-ProstaneChEBI
(8b)-ProstaneGenerator
(8Β)-prostaneGenerator
8-beta-ProstaneHMDB
15-F(2t)-IsoprostaneMeSH, HMDB
8-iso-PGF(2alpha)MeSH, HMDB
15-F(2t)-IsoPMeSH, HMDB
8-Epi-PGF2alphaMeSH, HMDB
8-Epi-prostaglandin F2alphaMeSH, HMDB
8-iso-PGF2alphaMeSH, HMDB
Isoprostaglandin F2alpha type-IIIMeSH, HMDB
8-Isoprostaglandin F2alphaMeSH, HMDB
8-Epiprostaglandin F2alphaMeSH, HMDB
8-F(2t)-IsoprostaneMeSH, HMDB
8-Epi-PGF2 alphaMeSH, HMDB
15-F2t-IsoPMeSH, HMDB
15-F2t-IsoprostaneMeSH, HMDB
(8β)-prostaneGenerator
8-beta-prostanehmdb
8-Isoprostanehmdb
Predicted Properties
PropertyValueSource
Water Solubility7.8e-06 g/LALOGPS
logP9.29ALOGPS
logP8.58ChemAxon
logS-7.6ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count13ChemAxon
Refractivity91.92 m³·mol⁻¹ChemAxon
Polarizability40.05 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC20H40
IUPAC name(1R,2S)-1-heptyl-2-octylcyclopentane
InChI IdentifierInChI=1S/C20H40/c1-3-5-7-9-11-13-16-20-18-14-17-19(20)15-12-10-8-6-4-2/h19-20H,3-18H2,1-2H3/t19-,20+/m1/s1
InChI KeyUKVVPDHLUHAJNZ-UXHICEINSA-N
Isomeric SMILES[H][C@@]1(CCCCCCC)CCC[C@]1([H])CCCCCCCC
Average Molecular Weight280.5316
Monoisotopic Molecular Weight280.31300128
Classification
Description Belongs to the class of organic compounds known as cycloalkanes. These are saturated monocyclic hydrocarbons (with or without side chains).
KingdomOrganic compounds
Super ClassHydrocarbons
ClassSaturated hydrocarbons
Sub ClassCycloalkanes
Direct ParentCycloalkanes
Alternative ParentsNot Available
Substituents
  • Cycloalkane
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

Disposition

Source:

Biological location:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MS8-Isoprostane, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0q3a-5690000000-8578513810f15e2b1675Spectrum
Predicted GC-MS8-Isoprostane, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS8-Isoprostane, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0290000000-a20b197c3e7f1d74f249Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001j-4890000000-eb1a2356a35d532ad8e6Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-059g-9570000000-b243e014ae11d5220934Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0090000000-ea56d8a3a2a3da747c77Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-0090000000-b99d9f57d25c668e68d2Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03g1-2590000000-7060fdcd4f3536c40ac1Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-2090000000-1aa04390e1979d610a49Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0560-9560000000-24c9aaae80f6353f7332Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4l-9510000000-2a35251ab7150a2a305dSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0090000000-bc21dbf6b7d615cdf298Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-0090000000-bc21dbf6b7d615cdf298Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-0090000000-8d49c6985a616961b999Spectrum
NMRNot Available
ChemSpider ID97008
ChEMBL IDNot Available
KEGG Compound IDC13809
Pubchem Compound ID107873
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB04659
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
Pathways
NameSMPDB LinkKEGG Link
Arachidonic Acid MetabolismSMP00075 map00590
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference