ChemFOnt: Showing chemical card for 8R-Hydroperoxylinoleic acid (CFc000336975)

Record Information

Version

1.0

Creation Date

Update Date

2022-09-14 05:30:26 UTC

Chemfont ID

CFc000336975

Molecule Identification

Common Name

8R-Hydroperoxylinoleic acid

Definition

8(R)-hydroperoxylinoleic acid (8(R)-EPODE) is an oxidized product of linoleic acid. Oxidized lipids such as 8(R)-HPODE can decrease cellular proteoglycan metabolism in endothelial monolayers and alter mRNA levels of major specific proteoglycans in a concentration-dependent manner. This may have implications in lipid-mediated disruption of endothelial barrier function and atherosclerosis. (PMID: 8645361 , 9507987 ) [HMDB]

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
8R-Hydroperoxylinoleate	Generator
8-HPODE	MeSH
8-Hydroperoxylinoleic acid	MeSH

Chemical Formula

C₁₈H₃₂O₄

Average Molecular Weight

312.4443

Monoisotopic Molecular Weight

312.230059512

IUPAC Name

(8R)-8-hydroperoxyoctadeca-9,12-dienoic acid

Traditional Name

(8R)-8-hydroperoxyoctadeca-9,12-dienoic acid

CAS Registry Number

143343-95-7

SMILES

[H][C@](CCCCCCC(O)=O)(OO)C=CCC=CCCCCC

InChI Identifier

InChI=1S/C18H32O4/c1-2-3-4-5-6-7-8-11-14-17(22-21)15-12-9-10-13-16-18(19)20/h6-7,11,14,17,21H,2-5,8-10,12-13,15-16H2,1H3,(H,19,20)/t17-/m0/s1

InChI Key

RGJSGXNKRWWCOQ-KRWDZBQOSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as lineolic acids and derivatives. These are derivatives of lineolic acid. Lineolic acid is a polyunsaturated omega-6 18 carbon long fatty acid, with two CC double bonds at the 9- and 12-positions.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Lineolic acids and derivatives

Direct Parent

Lineolic acids and derivatives

Alternative Parents

Substituents

Octadecanoid
Long-chain fatty acid
Hydroperoxy fatty acid
Fatty acid
Unsaturated fatty acid
Allylic hydroperoxide
Hydroperoxide
Carboxylic acid derivative
Alkyl hydroperoxide
Carboxylic acid
Peroxol
Monocarboxylic acid or derivatives
Carbonyl group
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Exogenous (HMDB: HMDB04706)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.0041 g/L	ALOGPS
logP	5.68	ALOGPS
logP	5.64	ChemAxon
logS	-4.9	ALOGPS
pKa (Strongest Acidic)	4.45	ChemAxon
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.76 Å²	ChemAxon
Rotatable Bond Count	15	ChemAxon
Refractivity	91.38 m³·mol⁻¹	ChemAxon
Polarizability	37.42 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB023417

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

3035745

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for 8R-Hydroperoxylinoleic acid (CFc000336975)

MOL for CFc000336975 (8R-Hydroperoxylinoleic acid)

3D MOL for CFc000336975 (8R-Hydroperoxylinoleic acid)

3D SDF for CFc000336975 (8R-Hydroperoxylinoleic acid)

3D-SDF for CFc000336975 (8R-Hydroperoxylinoleic acid)

PDB for CFc000336975 (8R-Hydroperoxylinoleic acid)

3D PDB for CFc000336975 (8R-Hydroperoxylinoleic acid)

SMILES for CFc000336975 (8R-Hydroperoxylinoleic acid)

INCHI for CFc000336975 (8R-Hydroperoxylinoleic acid)

Structure for CFc000336975 (8R-Hydroperoxylinoleic acid)

3D Structure for CFc000336975 (8R-Hydroperoxylinoleic acid)