ChemFOnt: Showing chemical card for 9,10-DHOME (CFc000002183)

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

CFc000002183

Molecule Identification

Common Name

9,10-DHOME

Definition

9,10-Dihydroxy-12-octadecenoic acid (CAS: 263399-34-4), also known as 9,10-DHOME, is a derivative of linoleic acid diol and has been reported to be toxic in human's tissue preparations. 9,10-DHOME is a naturally occurring proliferator-activated receptor (PPAR) gamma2 ligand, which stimulates adipocytes and inhibits osteoblast differentiation. 9,10-DHOME is the epoxide hydrolase metabolite of the leukotoxin 9,10-EpOME. 9,10-EpOME act as a protoxin, with the corresponding epoxide hydrolase metabolite 9,10-DHOME, specifically exerting toxicity. Both 9,10-EpOME and 9,10-DHOME are shown to have neutrophil chemotactic activity. 9,10-DHOME suppresses the neutrophil respiratory burst by a mechanism distinct from that of respiratory burst inhibitors such as cyclosporin H or lipoxin A4, which inhibit multiple aspects of neutrophil activation (PMID: 12021203 , 12127265 , 17435320 ). 9,10-DHOME is found in fruits and can be isolated from the seeds of Cucurbita pepo.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
LX-Diol	MeSH
Leukotoxin-diol	MeSH

Chemical Formula

C₁₈H₃₄O₄

Average Molecular Weight

314.4602

Monoisotopic Molecular Weight

314.245709576

IUPAC Name

(12E)-9,10-dihydroxyoctadec-12-enoic acid

Traditional Name

(12E)-9,10-dihydroxyoctadec-12-enoic acid

CAS Registry Number

125356-86-7

SMILES

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

InChI Identifier

InChI=1S/C18H34O4/c1-2-3-4-5-7-10-13-16(19)17(20)14-11-8-6-9-12-15-18(21)22/h7,10,16-17,19-20H,2-6,8-9,11-15H2,1H3,(H,21,22)/b10-7+

InChI Key

XEBKSQSGNGRGDW-JXMROGBWSA-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
1,2-diol
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

Other Octadecanoids (LMFA02000161 )

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 18953024)
Cerebrospinal Fluid (CSF) (HMDB: HMDB0004704)

Cellular substructure

Organelle

Adiposome (HMDB: HMDB0004704)

Excreta

Biofluid or Excreta

Feces (PMID: 27543620)
Urine (HMDB: HMDB0004704)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0004704)

Source

Endogenous

Endogenous (HMDB: HMDB0004704)

Plant

Plant (HMDB: HMDB0004704)

Animal

Animal (HMDB: HMDB0004704)

Exogenous

Food

Food (HMDB: HMDB0004704)

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: HMDB0004704)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0004704)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0004704)

Lipid metabolism pathway (HMDB: HMDB0004704)

Cellular process

Cell signaling (HMDB: HMDB0004704)

Biochemical process

Lipid transport (HMDB: HMDB0004704)

Role

Biological role

Energy source (HMDB: HMDB0004704)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0004704)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.04 g/L	ALOGPS
logP	5.18	ALOGPS
logP	4.32	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Acidic)	4.62	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	77.76 Å²	ChemAxon
Rotatable Bond Count	15	ChemAxon
Refractivity	90.43 m³·mol⁻¹	ChemAxon
Polarizability	39.26 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

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB023415

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

5282958

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for 9,10-DHOME (CFc000002183)

MOL for CFc000002183 (9,10-DHOME)

3D MOL for CFc000002183 (9,10-DHOME)

3D SDF for CFc000002183 (9,10-DHOME)

3D-SDF for CFc000002183 (9,10-DHOME)

PDB for CFc000002183 (9,10-DHOME)

3D PDB for CFc000002183 (9,10-DHOME)

SMILES for CFc000002183 (9,10-DHOME)

INCHI for CFc000002183 (9,10-DHOME)

Structure for CFc000002183 (9,10-DHOME)

3D Structure for CFc000002183 (9,10-DHOME)