ChemFOnt: Showing chemical card for 8(R)-Hydroperoxylinoleic acid (CFc000002185)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:47:00 UTC

Chemfont ID

CFc000002185

Molecule Identification

Common Name

8(R)-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 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(8R)-8-Hydroperoxylinoleic acid	ChEBI
(9Z,12Z)-(8R)-8-Hydroperoxyoctadeca-9,12-dienoic acid	ChEBI
(8R,9Z,12Z)-8-Hydroperoxyoctadeca-9,12-dienoate	Kegg
(8R)-8-Hydroperoxylinoleate	Generator
(9Z,12Z)-(8R)-8-Hydroperoxyoctadeca-9,12-dienoate	Generator
(8R,9Z,12Z)-8-Hydroperoxyoctadeca-9,12-dienoic acid	Generator
8(R)-Hydroperoxylinoleate	Generator
(R-(Z,Z))-8-Hydroperoxy-9,12-octadecadienoate	HMDB
(R-(Z,Z))-8-Hydroperoxy-9,12-octadecadienoic acid	HMDB
8(R)-HPODE	HMDB
8-Hpode	HMDB
8-Hydroperoxylinoleic acid	HMDB
8R-Hydroperoxy-9Z,12Z-octadecadienoate	HMDB
8R-Hydroperoxy-9Z,12Z-octadecadienoic acid	HMDB

Chemical Formula

C₁₈H₃₂O₄

Average Molecular Weight

312.4443

Monoisotopic Molecular Weight

312.230059512

IUPAC Name

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

Traditional Name

8-hpode

CAS Registry Number

143343-95-7

SMILES

CCCCC\C=C/C\C=C/[C@@H](CCCCCCC(O)=O)OO

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)/b7-6-,14-11-/t17-/m0/s1

InChI Key

RGJSGXNKRWWCOQ-QMEIEYGNSA-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

HPODE (CHEBI:34485 )
octadecanoid (CHEBI:34485 )
Other Octadecanoids (C14831 )
Other Octadecanoids (LMFA02000113 )

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0004706)
Membrane (HMDB: HMDB0004706)

Source

Exogenous

Exogenous (HMDB: HMDB0004706)

Food

Animal origin

Poultry

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)

Endogenous

Endogenous (HMDB: HMDB0004706)

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	37.37 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

HMDB0004706

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB112218

KNApSAcK ID

Not Available

Chemspider ID

4943210

KEGG Compound ID

C14831

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6438758

PDB ID

Not Available

ChEBI ID

34485

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for 8(R)-Hydroperoxylinoleic acid (CFc000002185)

MOL for CFc000002185 (8(R)-Hydroperoxylinoleic acid)

3D MOL for CFc000002185 (8(R)-Hydroperoxylinoleic acid)

3D SDF for CFc000002185 (8(R)-Hydroperoxylinoleic acid)

3D-SDF for CFc000002185 (8(R)-Hydroperoxylinoleic acid)

PDB for CFc000002185 (8(R)-Hydroperoxylinoleic acid)

3D PDB for CFc000002185 (8(R)-Hydroperoxylinoleic acid)

SMILES for CFc000002185 (8(R)-Hydroperoxylinoleic acid)

INCHI for CFc000002185 (8(R)-Hydroperoxylinoleic acid)

Structure for CFc000002185 (8(R)-Hydroperoxylinoleic acid)

3D Structure for CFc000002185 (8(R)-Hydroperoxylinoleic acid)