ChemFOnt: Showing chemical card for 9,10-Epoxyoctadecenoic acid (CFc000002181)

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

CFc000002181

Molecule Identification

Common Name

9,10-Epoxyoctadecenoic acid

Definition

9,10-Epoxyoctadecenoic acid (9,10-EOA) is a peroxidation product of linoleic acid (LA). 9,10-EOA is a naturally occurring component of oxidized low density lipoprotein (LDL), the level of which increases with aging, atherosclerosis, and rheumatoid arthritis, perhaps due to an increase in 15-lipoxygenase and free oxygen radicals. 9,10-EOA is a proliferator-activated receptors (PPAR) gamma2 ligand, that is antiosteogenic without stimulating adipocyte differentiation. Studies in dogs suggest that 9,10-EOA has toxic cardiovascular effects. (PMID: 12665667 , 12021203 , 10667371 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
9(10)-Epoxyoctadec-12Z-enoic acid	ChEBI
9,10-EOA	ChEBI
9,10-Epoxy-12Z-octadecenoic acid	ChEBI
9,10-Epoxyoctadec-12(Z)-enoic acid	ChEBI
Coronaric acid	ChEBI
9(10)-Epoxyoctadec-12Z-enoate	Generator
9,10-Epoxy-12Z-octadecenoate	Generator
9,10-Epoxyoctadec-12(Z)-enoate	Generator
Coronarate	Generator
9,10-Epoxyoctadecenoate	Generator
(+/-)-9(10)-epoxy-12Z-octadecenoate	HMDB
(+/-)-9(10)-epoxy-12Z-octadecenoic acid	HMDB
9(10)-EpOME	HMDB
9,10-Epoxyoctadecenoic acid	ChEBI

Chemical Formula

C₁₈H₃₂O₃

Average Molecular Weight

296.4449

Monoisotopic Molecular Weight

296.23514489

IUPAC Name

8-{3-[(2Z)-oct-2-en-1-yl]oxiran-2-yl}octanoic acid

Traditional Name

9,10-epoxyoctadecenoic acid

CAS Registry Number

None

SMILES

CCCCC\C=C/CC1OC1CCCCCCCC(O)=O

InChI Identifier

InChI=1S/C18H32O3/c1-2-3-4-5-7-10-13-16-17(21-16)14-11-8-6-9-12-15-18(19)20/h7,10,16-17H,2-6,8-9,11-15H2,1H3,(H,19,20)/b10-7-

InChI Key

FBUKMFOXMZRGRB-YFHOEESVSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acids and conjugates

Direct Parent

Medium-chain fatty acids

Alternative Parents

Substituents

Medium-chain fatty acid
Epoxy fatty acid
Heterocyclic fatty acid
Carboxylic acid derivative
Carboxylic acid
Dialkyl ether
Oxirane
Ether
Monocarboxylic acid or derivatives
Oxacycle
Organoheterocyclic compound
Organic oxide
Carbonyl group
Organooxygen compound
Hydrocarbon derivative
Organic oxygen compound
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

epoxyoctadecenoic acid (CHEBI:34494 )
Other Octadecanoids (LMFA02000037 )

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 18953024)
Cerebrospinal Fluid (CSF) (HMDB: HMDB0004701)

Cellular substructure

Extracellular (HMDB: HMDB0004701)
Membrane (HMDB: HMDB0004701)

Source

Exogenous

Exogenous (HMDB: HMDB0004701)

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: HMDB0004701)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.0005 g/L	ALOGPS
logP	6.35	ALOGPS
logP	5.48	ChemAxon
logS	-5.8	ALOGPS
pKa (Strongest Acidic)	4.62	ChemAxon
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	49.83 Å²	ChemAxon
Rotatable Bond Count	14	ChemAxon
Refractivity	86.92 m³·mol⁻¹	ChemAxon
Polarizability	37.22 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0004701

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB112216

KNApSAcK ID

Not Available

Chemspider ID

4861048

KEGG Compound ID

C14825

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6246154

PDB ID

Not Available

ChEBI ID

34494

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for 9,10-Epoxyoctadecenoic acid (CFc000002181)

MOL for CFc000002181 (9,10-Epoxyoctadecenoic acid)

3D MOL for CFc000002181 (9,10-Epoxyoctadecenoic acid)

3D SDF for CFc000002181 (9,10-Epoxyoctadecenoic acid)

3D-SDF for CFc000002181 (9,10-Epoxyoctadecenoic acid)

PDB for CFc000002181 (9,10-Epoxyoctadecenoic acid)

3D PDB for CFc000002181 (9,10-Epoxyoctadecenoic acid)

SMILES for CFc000002181 (9,10-Epoxyoctadecenoic acid)

INCHI for CFc000002181 (9,10-Epoxyoctadecenoic acid)

Structure for CFc000002181 (9,10-Epoxyoctadecenoic acid)

3D Structure for CFc000002181 (9,10-Epoxyoctadecenoic acid)