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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2006-08-13 23:19:54 UTC
Update Date2017-12-07 01:53:52 UTC
HMDB IDHMDB0004659
Secondary Accession Numbers
  • HMDB04659
Metabolite Identification
Common 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).
Structure
Thumb
Synonyms
ValueSource
(1R,2S)-1-Heptyl-2-octylcyclopentaneChEBI
(8beta)-ProstaneChEBI
(8b)-ProstaneGenerator
(8β)-prostaneGenerator
8-beta-ProstaneHMDB
15-F(2t)-IsoprostaneMeSH
8-iso-PGF(2alpha)MeSH
15-F(2t)-IsoPMeSH
8-Epi-PGF2alphaMeSH
8-Epi-prostaglandin F2alphaMeSH
8-iso-PGF2alphaMeSH
Isoprostaglandin F2alpha type-IIIMeSH
8-Isoprostaglandin F2alphaMeSH
8-Epiprostaglandin F2alphaMeSH
8-F(2t)-IsoprostaneMeSH
8-Epi-PGF2 alphaMeSH
Chemical FormulaC20H40
Average Molecular Weight280.5316
Monoisotopic Molecular Weight280.31300128
IUPAC Name(1R,2S)-1-heptyl-2-octylcyclopentane
Traditional Name8β-prostane
CAS Registry Number155976-51-5
SMILES
[H][C@@]1(CCCCCCC)CCC[C@]1([H])CCCCCCCC
InChI Identifier
InChI=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
DescriptionThis compound belongs to the class of chemical entities known as cycloalkanes. These are saturated monocyclic hydrocarbons (with or without side chains).
KingdomChemical entities
Super ClassOrganic compounds
ClassHydrocarbons
Sub ClassSaturated hydrocarbons
Direct ParentCycloalkanes
Alternative ParentsNot Available
Substituents
  • Cycloalkane
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External Descriptors
Ontology
Process

Naturally occurring process:

  Biological process:

    Biochemical pathway:

Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

  Tissue and substructures:

  Organ and components:

  Cell and elements:

    Element:

Source:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot 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 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, Positivesplash10-0q3a-5690000000-8578513810f15e2b1675View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0290000000-a20b197c3e7f1d74f249View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001j-4890000000-eb1a2356a35d532ad8e6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-059g-9570000000-b243e014ae11d5220934View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0090000000-ea56d8a3a2a3da747c77View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-0090000000-b99d9f57d25c668e68d2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03g1-2590000000-7060fdcd4f3536c40ac1View in MoNA
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biofluid Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Urine
Tissue Location
  • Adipose Tissue
  • Platelet
  • Skin
Pathways
NameSMPDB/PathwhizKEGG
Acetaminophen Action PathwayPw000687Pw000687 greyscalePw000687 simpleNot Available
Acetylsalicylic Acid PathwayPw000128Pw000128 greyscalePw000128 simpleNot Available
Antipyrine Action PathwayPw000669Pw000669 greyscalePw000669 simpleNot Available
Antrafenine Action PathwayPw000670Pw000670 greyscalePw000670 simpleNot Available
Arachidonic Acid MetabolismPw000044Pw000044 greyscalePw000044 simpleMap00590
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.00011 +/- 0.00004 uMAdult (>18 years old)MaleNormal details
BloodDetected and Quantified0.00053 +/- 0.000043 uMAdult (>18 years old)MaleNormal details
BloodDetected and Quantified0.00047 +/- 0.000014 uMAdult (>18 years old)FemaleNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified0.00003 +/- 0.00002 uMAdult (>18 years old)Not SpecifiedNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified0.000021 (0.0000071-0.000035) uMAdult (>18 years old)Not SpecifiedNormal details
UrineDetected and Quantified0.00007 - 0.0005 umol/mmol creatinineAdult (>18 years old)Not SpecifiedNormal details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
Cerebrospinal Fluid (CSF)Detected and Quantified0.0003 +/- 0.0001 uMChildren (1-13 years old)Not Specified
Brain injury
details
Associated Disorders and Diseases
Disease References
Traumatic brain injury
  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. [PubMed:11978879 ]
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB023392
KNApSAcK IDNot Available
Chemspider ID97008
KEGG Compound IDC13809
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID7067
PubChem Compound107873
PDB IDNot Available
ChEBI ID33023
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not 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. [PubMed:11978879 ]
  2. 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. [PubMed:16249455 ]
  3. 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. [PubMed:10235090 ]
  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. [PubMed:16685055 ]
  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. [PubMed:10447118 ]
  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. [PubMed:16357066 ]
  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. [PubMed:16219641 ]
  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. [PubMed:16164445 ]
  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. [PubMed:16164830 ]
  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. [PubMed:16702043 ]
  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. [PubMed:11883375 ]
  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. [PubMed:16704647 ]
  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. [PubMed:16491351 ]
  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. [PubMed:11035329 ]
  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. [PubMed:14555570 ]
  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. [PubMed:14669408 ]
  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. [PubMed:15531521 ]
  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. [PubMed:11048736 ]
  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. [PubMed:11884287 ]
  20. Misso NL, Thompson PJ: Oxidative stress and antioxidant deficiencies in asthma: potential modification by diet. Redox Rep. 2005;10(5):247-55. [PubMed:16354413 ]
  21. Jankov RP, Keith Tanswell A: Growth factors, postnatal lung growth and bronchopulmonary dysplasia. Paediatr Respir Rev. 2004;5 Suppl A:S265-75. [PubMed:14980283 ]