ChemFOnt: Showing chemical card for 9,10-DiHODE (CFc000006230)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:52:09 UTC

Chemfont ID

CFc000006230

Molecule Identification

Common Name

9,10-DiHODE

Definition

9,10-DiHODE or 9,10-dihydroxy-12Z,15Z- octadecadienoic acid is an oxylipin. It is a double oxidation product of octadeadienoic acid generated through the action of CYP450 on linolenic acid (PMID: 6301473 ). Specifically cytochrome P-450 catalyzed epoxidation of the omega 3, omega 6 and omega 9 double bonds, followed by enzymatic hydrolysis to 1,2-diols would lead to this compound.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Not Available

Chemical Formula

C₁₈H₃₂O₄

Average Molecular Weight

312.4443

Monoisotopic Molecular Weight

312.230059512

IUPAC Name

9,10-dihydroxyoctadeca-12,15-dienoic acid

Traditional Name

9,10-dihydroxyoctadeca-12,15-dienoic acid

CAS Registry Number

None

SMILES

CCC=CCC=CCC(O)C(O)CCCCCCCC(O)=O

InChI Identifier

InChI=1S/C18H32O4/c1-2-3-4-5-7-10-13-16(19)17(20)14-11-8-6-9-12-15-18(21)22/h3-4,7,10,16-17,19-20H,2,5-6,8-9,11-15H2,1H3,(H,21,22)

InChI Key

QRHSEDZBZMZPOA-UHFFFAOYSA-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
Hydroxy fatty acid
Unsaturated fatty acid
Fatty acid
Secondary alcohol
1,2-diol
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
Alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 18953024)

Cellular substructure

Membrane (HMDB: HMDB0010221)

Source

Endogenous

Endogenous (HMDB: HMDB0010221)

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)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.051 g/L	ALOGPS
logP	4.88	ALOGPS
logP	3.96	ChemAxon
logS	-3.8	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	14	ChemAxon
Refractivity	91.55 m³·mol⁻¹	ChemAxon
Polarizability	37.92 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

FDB027374

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

54242986

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for 9,10-DiHODE (CFc000006230)

MOL for CFc000006230 (9,10-DiHODE)

3D MOL for CFc000006230 (9,10-DiHODE)

3D SDF for CFc000006230 (9,10-DiHODE)

3D-SDF for CFc000006230 (9,10-DiHODE)

PDB for CFc000006230 (9,10-DiHODE)

3D PDB for CFc000006230 (9,10-DiHODE)

SMILES for CFc000006230 (9,10-DiHODE)

INCHI for CFc000006230 (9,10-DiHODE)

Structure for CFc000006230 (9,10-DiHODE)

3D Structure for CFc000006230 (9,10-DiHODE)