8-Isoprostane (CHEM021653)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (25)XML
Record Information
Version1.0
Creation Date2016-05-25 18:09:13 UTC
Update Date2026-08-20 07:02:37 UTC
Accession NumberCHEM021653
Identification
Common Name8-Isoprostane
ClassSmall Molecule
Description
Contaminant Sources
  • FooDB Chemicals
  • HMDB Contaminants - Urine
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(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
Chemical FormulaC20H40
Average Molecular Mass280.532 g/mol
Monoisotopic Mass280.313 g/mol
CAS Registry Number155976-51-5
IUPAC Namecis-(1R,2S)-1-heptyl-2-octylcyclopentane
Traditional Name8β-prostane
SMILES[H][C@@]1(CCCCCCC)CCC[C@]1([H])CCCCCCCC
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
Chemical Taxonomy
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
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
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
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0q3a-5690000000-8578513810f15e2b1675Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0290000000-a20b197c3e7f1d74f249Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001j-4890000000-eb1a2356a35d532ad8e6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-059g-9570000000-b243e014ae11d5220934Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0090000000-ea56d8a3a2a3da747c77Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-0090000000-b99d9f57d25c668e68d2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03g1-2590000000-7060fdcd4f3536c40ac1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-2090000000-1aa04390e1979d610a49Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0560-9560000000-24c9aaae80f6353f7332Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4l-9510000000-2a35251ab7150a2a305dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0090000000-bc21dbf6b7d615cdf298Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-0090000000-bc21dbf6b7d615cdf298Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-0090000000-8d49c6985a616961b999Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0004659
FooDB IDFDB023392
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN ID7067
PDB IDNot Available
Wikipedia LinkIsoprostane
Chemspider ID97008
ChEBI ID33023
PubChem Compound ID107873
Kegg Compound IDC13809
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Bayir H, Kagan VE, Tyurina YY, Tyurin V, Ruppel RA, Adelson PD, Graham SH, Janesko K, Clark RS, Kochanek PM: Assessment of antioxidant reserves and oxidative stress in cerebrospinal fluid after severe traumatic brain injury in infants and children. Pediatr Res. 2002 May;51(5):571-8.
2. Raal FJ, Pilcher GJ, Waisberg R, Buthelezi EP, Veller MG, Joffe BI: Low-density lipoprotein cholesterol bulk is the pivotal determinant of atherosclerosis in familial hypercholesterolemia. Am J Cardiol. 1999 May 1;83(9):1330-3.
3. Beisswenger PJ, Drummond KS, Nelson RG, Howell SK, Szwergold BS, Mauer M: Susceptibility to diabetic nephropathy is related to dicarbonyl and oxidative stress. Diabetes. 2005 Nov;54(11):3274-81.
4. Ryan-Borchers TA, Park JS, Chew BP, McGuire MK, Fournier LR, Beerman KA: Soy isoflavones modulate immune function in healthy postmenopausal women. Am J Clin Nutr. 2006 May;83(5):1118-25.
5. Luo X, Sedlackova L, Belcastro R, Cabacungan J, Lye SJ, Tanswell AK: Effect of the 21-aminosteroid U74389G on oxygen-induced free radical production, lipid peroxidation, and inhibition of lung growth in neonatal rats. Pediatr Res. 1999 Aug;46(2):215-23.
6. Roberts CK, Won D, Pruthi S, Kurtovic S, Sindhu RK, Vaziri ND, Barnard RJ: Effect of a short-term diet and exercise intervention on oxidative stress, inflammation, MMP-9, and monocyte chemotactic activity in men with metabolic syndrome factors. J Appl Physiol (1985). 2006 May;100(5):1657-65. Epub 2005 Dec 15.
7. Volpe A, Biasi D, Caramaschi P, Mantovani W, Bambara LM, Canestrini S, Ferrari M, Poli G, Degan M, Carletto A, Pieropan S, Minuz P: Levels of F2-isoprostanes in systemic sclerosis: correlation with clinical features. Rheumatology (Oxford). 2006 Mar;45(3):314-20. Epub 2005 Oct 11.
8. Simpson JL, Wood LG, Gibson PG: Inflammatory mediators in exhaled breath, induced sputum and saliva. Clin Exp Allergy. 2005 Sep;35(9):1180-5.
9. Belli R, Amerio P, Brunetti L, Orlando G, Toto P, Proietto G, Vacca M, Tulli A: Elevated 8-isoprostane levels in basal cell carcinoma and in UVA irradiated skin. Int J Immunopathol Pharmacol. 2005 Jul-Sep;18(3):497-502.
10. Kranzhofer R, Ruef J: Aspirin resistance in coronary artery disease is correlated to elevated markers for oxidative stress but not to the expression of cyclooxygenase (COX) 1/2, a novel COX-1 polymorphism or the PlA(1/2) polymorphism. Platelets. 2006 May;17(3):163-9.
11. Khaw KS, Wang CC, Ngan Kee WD, Pang CP, Rogers MS: Effects of high inspired oxygen fraction during elective caesarean section under spinal anaesthesia on maternal and fetal oxygenation and lipid peroxidation. Br J Anaesth. 2002 Jan;88(1):18-23.
12. Schneider LA, Bloch W, Kopp K, Hainzl A, Rettberg P, Wlaschek M, Horneck G, Scharffetter-Kochanek K: 8-Isoprostane is a dose-related biomarker for photo-oxidative ultraviolet (UV) B damage in vivo: a pilot study with personal UV dosimetry. Br J Dermatol. 2006 Jun;154(6):1147-54.
13. Kuhn M, Wolber R, Kolbe L, Schnorr O, Sies H: Solar-simulated radiation induces secretion of IL-6 and production of isoprostanes in human skin in vivo. Arch Dermatol Res. 2006 Apr;297(10):477-9. Epub 2006 Feb 21.
14. McKinney ET, Shouri R, Hunt RS, Ahokas RA, Sibai BM: Plasma, urinary, and salivary 8-epi-prostaglandin f2alpha levels in normotensive and preeclamptic pregnancies. Am J Obstet Gynecol. 2000 Oct;183(4):874-7.
15. Carpagnano GE, Kharitonov SA, Resta O, Foschino-Barbaro MP, Gramiccioni E, Barnes PJ: 8-Isoprostane, a marker of oxidative stress, is increased in exhaled breath condensate of patients with obstructive sleep apnea after night and is reduced by continuous positive airway pressure therapy. Chest. 2003 Oct;124(4):1386-92.
16. Karowicz-Bilinska A, Kowalska-Koprek U, Suzin J, Sieroszewski P: [Analysis of 8-isoprostane concentration as a marker of oxidative stress in pregnant women diagnosed with IUGR]. Ginekol Pol. 2003 Oct;74(10):1137-42.
17. Lappas M, Permezel M, Rice GE: Release of proinflammatory cytokines and 8-isoprostane from placenta, adipose tissue, and skeletal muscle from normal pregnant women and women with gestational diabetes mellitus. J Clin Endocrinol Metab. 2004 Nov;89(11):5627-33.
18. Ohashi N, Yoshikawa M: Rapid and sensitive quantification of 8-isoprostaglandin F2alpha in human plasma and urine by liquid chromatography-electrospray ionization mass spectrometry. J Chromatogr B Biomed Sci Appl. 2000 Sep 1;746(1):17-24.
19. Ide T, Tsutsui H, Ohashi N, Hayashidani S, Suematsu N, Tsuchihashi M, Tamai H, Takeshita A: Greater oxidative stress in healthy young men compared with premenopausal women. Arterioscler Thromb Vasc Biol. 2002 Mar 1;22(3):438-42.
20. Misso NL, Thompson PJ: Oxidative stress and antioxidant deficiencies in asthma: potential modification by diet. Redox Rep. 2005;10(5):247-55.
21. Jankov RP, Keith Tanswell A: Growth factors, postnatal lung growth and bronchopulmonary dysplasia. Paediatr Respir Rev. 2004;5 Suppl A:S265-75.