ChemFOnt: Showing chemical card for 8-Isoprostane (CFc000002160)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:46:58 UTC

Chemfont ID

CFc000002160

Molecule Identification

Common Name

8-Isoprostane

Definition

8-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

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(1R,2S)-1-Heptyl-2-octylcyclopentane	ChEBI
(8beta)-Prostane	ChEBI
(8b)-Prostane	Generator
(8Β)-prostane	Generator
8-beta-Prostane	HMDB
15-F(2t)-Isoprostane	MeSH, HMDB
8-iso-PGF(2alpha)	MeSH, HMDB
15-F(2t)-IsoP	MeSH, HMDB
8-Epi-PGF2alpha	MeSH, HMDB
8-Epi-prostaglandin F2alpha	MeSH, HMDB
8-iso-PGF2alpha	MeSH, HMDB
Isoprostaglandin F2alpha type-III	MeSH, HMDB
8-Isoprostaglandin F2alpha	MeSH, HMDB
8-Epiprostaglandin F2alpha	MeSH, HMDB
8-F(2t)-Isoprostane	MeSH, HMDB
8-Epi-PGF2 alpha	MeSH, HMDB
15-F2t-IsoP	MeSH, HMDB
15-F2t-Isoprostane	MeSH, HMDB

Chemical Formula

C₂₀H₄₀

Average Molecular Weight

280.5316

Monoisotopic Molecular Weight

280.31300128

IUPAC Name

(1R,2S)-1-heptyl-2-octylcyclopentane

Traditional Name

8β-prostane

CAS Registry Number

155976-51-5

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 Key

UKVVPDHLUHAJNZ-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).

Kingdom

Organic compounds

Super Class

Hydrocarbons

Class

Saturated hydrocarbons

Sub Class

Cycloalkanes

Direct Parent

Cycloalkanes

Alternative Parents

Not Available

Substituents

Cycloalkane
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

1-heptyl-2-octylcyclopentane (CHEBI:33023 )

Functional Ontology

Physiological effect

Health effect

Nervous system disorder

Central nervous system disorder

Traumatic brain injury (HMDB: HMDB0004659)

Adipose tissue (HMDB: HMDB0004659)
Adipose tissue (HMDB: HMDB0004659)

Epithelium

Epidermis (HMDB: HMDB0004659)

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 18203893)
Cerebrospinal Fluid (CSF) (PMID: 11978879)
Cerebrospinal fluid (HMDB: HMDB0004659)

Cellular substructure

Membrane (HMDB: HMDB0004659)
Cell membrane (HMDB: HMDB0004659)

Cell

Hematocyte

Platelet (HMDB: HMDB0004659)

Excreta

Biofluid or Excreta

Urine (PMID: 11339277)

Organ

Skin (HMDB: HMDB0004659)

Source

Endogenous

Endogenous (HMDB: HMDB0004659)

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Process

Naturally occurring process

Biological process

Biochemical pathway

Drug action pathway

Acetylsalicylic Acid Action Pathway (HMDB: HMDB0004659)
Piroxicam Action Pathway (PathBank: SMP0000077)
Acetylsalicylic Acid Action Pathway (PathBank: SMP0000083)
Etodolac Action Pathway (PathBank: SMP0000084)
Ketoprofen Action Pathway (PathBank: SMP0000085)
Ibuprofen Action Pathway (PathBank: SMP0000086)
Rofecoxib Action Pathway (PathBank: SMP0000087)
Diclofenac Action Pathway (PathBank: SMP0000093)
Sulindac Action Pathway (PathBank: SMP0000094)
Celecoxib Action Pathway (PathBank: SMP0000096)
Ketorolac Action Pathway (PathBank: SMP0000098)
Suprofen Action Pathway (PathBank: SMP0000101)
Bromfenac Action Pathway (PathBank: SMP0000102)
Indomethacin Action Pathway (PathBank: SMP0000104)
Mefenamic Acid Action Pathway (PathBank: SMP0000109)
Oxaprozin Action Pathway (PathBank: SMP0000113)
Nabumetone Action Pathway (PathBank: SMP0000114)
Naproxen Action Pathway (PathBank: SMP0000120)
Diflunisal Action Pathway (PathBank: SMP0000289)
Meloxicam Action Pathway (PathBank: SMP0000106)
Valdecoxib Action Pathway (PathBank: SMP0000116)
Antipyrine Action Pathway (PathBank: SMP0000692)
Antrafenine Action Pathway (PathBank: SMP0000693)
Carprofen Action Pathway (PathBank: SMP0000694)
Etoricoxib Action Pathway (PathBank: SMP0000695)
Fenoprofen Action Pathway (PathBank: SMP0000696)
Flurbiprofen Action Pathway (PathBank: SMP0000697)
Magnesium salicylate Action Pathway (PathBank: SMP0000698)
Lumiracoxib Action Pathway (PathBank: SMP0000699)
Lornoxicam Action Pathway (PathBank: SMP0000700)
Phenylbutazone Action Pathway (PathBank: SMP0000701)
Nepafenac Action Pathway (PathBank: SMP0000702)
Trisalicylate-choline Action Pathway (PathBank: SMP0000703)
Tolmetin Action Pathway (PathBank: SMP0000704)
Tiaprofenic Acid Action Pathway (PathBank: SMP0000705)
Tenoxicam Action Pathway (PathBank: SMP0000706)
Salsalate Action Pathway (PathBank: SMP0000707)
Salicylate-sodium Action Pathway (PathBank: SMP0000708)
Salicylic Acid Action Pathway (PathBank: SMP0000709)
Acetaminophen Action Pathway (PathBank: SMP0000710)

Disease pathway

Leukotriene C4 Synthesis Deficiency (PathBank: SMP0120510)

Metabolic pathway

Arachidonic Acid Metabolism (PathBank: SMP0087315)
Arachidonic Acid Metabolism (HMDB: HMDB0004659)

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	7.8e-06 g/L	ALOGPS
logP	9.29	ALOGPS
logP	8.58	ChemAxon
logS	-7.6	ALOGPS
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	0	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	0 Å²	ChemAxon
Rotatable Bond Count	13	ChemAxon
Refractivity	91.92 m³·mol⁻¹	ChemAxon
Polarizability	40.05 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon