ChemFOnt: Showing chemical card for 9,12,13-TriHOME (CFc000002186)

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

CFc000002186

Molecule Identification

Common Name

9,12,13-TriHOME

Definition

9,12,13-TriHOME is a trihydroxyoctadecenoic acid metabolite of linoleic acid, one of the major fatty acids found in lipids. Vascular tissue converts various polyunsaturated fatty acids to monohydroxy and trihydroxy metabolites derived from hydroperoxides which may be involved in regulating prostaglandin synthesis. The absolute amounts of 9,12,13-TriHOME varies considerably from one species to another. There are several possible mechanisms for the formation of esterified oxygenated polyunsaturated fatty acids: oxygenated and then incorporated into lipids, not well incorporated into either vascular endothelial or smooth muscle cells, or could accumulated in lipids either due to autoxidation in vivo or to the action of an enzyme similar to Iipoxygenase. (PMID: 3997883 , 6414520 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(10E)-(9S,12S,13S)-9,12,13-Trihydroxyoctadec-10-enoic acid	ChEBI
9(S),12(S),13(S)-Trihydroxy-10(e)-octadecenoic acid	ChEBI
9S,12S,13S-Trihydroxy-10E-octadecenoic acid	ChEBI
(10E)-(9S,12S,13S)-9,12,13-Trihydroxyoctadec-10-enoate	Generator
9(S),12(S),13(S)-Trihydroxy-10(e)-octadecenoate	Generator
9S,12S,13S-Trihydroxy-10E-octadecenoate	Generator
Pinellic acid	MeSH, HMDB

Chemical Formula

C₁₈H₃₄O₅

Average Molecular Weight

330.4596

Monoisotopic Molecular Weight

330.240624198

IUPAC Name

(9S,10E,12S,13S)-9,12,13-trihydroxyoctadec-10-enoic acid

Traditional Name

(9S,10E,12S,13S)-9,12,13-trihydroxyoctadec-10-enoic acid

CAS Registry Number

97134-11-7

SMILES

CCCCC[C@H](O)[C@@H](O)\C=C\[C@@H](O)CCCCCCCC(O)=O

InChI Identifier

InChI=1S/C18H34O5/c1-2-3-7-11-16(20)17(21)14-13-15(19)10-8-5-4-6-9-12-18(22)23/h13-17,19-21H,2-12H2,1H3,(H,22,23)/b14-13+/t15-,16-,17-/m0/s1

InChI Key

MDIUMSLCYIJBQC-MVFSOIOZSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acids and conjugates

Direct Parent

Long-chain fatty acids

Alternative Parents

Substituents

Long-chain fatty acid
Hydroxy fatty acid
Unsaturated fatty acid
Secondary alcohol
Polyol
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

TriHOME (CHEBI:34506 )
Other Octadecanoids (C14833 )
Other Octadecanoids (LMFA02000014 )

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 18953024)

Cellular substructure

Organelle

Adiposome (HMDB: HMDB0004708)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0004708)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0004708)

Source

Endogenous

Endogenous (HMDB: HMDB0004708)

Animal

Animal (HMDB: HMDB0004708)

Exogenous

Food

Food (HMDB: HMDB0004708)

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)

Exogenous (HMDB: HMDB0004708)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0004708)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0004708)

Lipid metabolism pathway (HMDB: HMDB0004708)

Cellular process

Cell signaling (HMDB: HMDB0004708)

Biochemical process

Lipid transport (HMDB: HMDB0004708)

Role

Biological role

Energy source (HMDB: HMDB0004708)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0004708)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.16 g/L	ALOGPS
logP	3.77	ALOGPS
logP	3.25	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	4.68	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	97.99 Å²	ChemAxon
Rotatable Bond Count	15	ChemAxon
Refractivity	91.79 m³·mol⁻¹	ChemAxon
Polarizability	40.04 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0004708

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB023418

KNApSAcK ID

Not Available

Chemspider ID

8034429

KEGG Compound ID

C14833

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

9858729

PDB ID

Not Available

ChEBI ID

34506

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for 9,12,13-TriHOME (CFc000002186)

MOL for CFc000002186 (9,12,13-TriHOME)

3D MOL for CFc000002186 (9,12,13-TriHOME)

3D SDF for CFc000002186 (9,12,13-TriHOME)

3D-SDF for CFc000002186 (9,12,13-TriHOME)

PDB for CFc000002186 (9,12,13-TriHOME)

3D PDB for CFc000002186 (9,12,13-TriHOME)

SMILES for CFc000002186 (9,12,13-TriHOME)

INCHI for CFc000002186 (9,12,13-TriHOME)

Structure for CFc000002186 (9,12,13-TriHOME)

3D Structure for CFc000002186 (9,12,13-TriHOME)