ChemFOnt: Showing chemical card for (9Z,11E)-13-Hydroxy-9,11-octadecadienoic acid (CFc000042124)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 19:44:28 UTC

Chemfont ID

CFc000042124

Molecule Identification

Common Name

(9Z,11E)-13-Hydroxy-9,11-octadecadienoic acid

Definition

13-Hydroxyoctadecadienoic acid (13-HODE) is the major lipoxygenation product derived from linoleic acid. It has been shown to be involved in cell proliferation and differentiation in a number of systems. 13-HODE is found to be produced by prostate tumors and cell lines and researchers believe there is a link between linoleic acid metabolism and the development or progression of prostate cancer. (PMID: 9367845

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(13S)-Hydroxyoctadecadienoic acid	ChEBI
(9Z, 11E)-(13S)-13-Hydroxyoctadeca-9,11-dienoic acid	ChEBI
(9Z,11E)-(13S)-13-Hydroxyoctadeca-9,11-dienoic acid	ChEBI
(13S)-Hydroxyoctadecadienoate	Generator
(9Z, 11E)-(13S)-13-Hydroxyoctadeca-9,11-dienoate	Generator
(9Z,11E)-(13S)-13-Hydroxyoctadeca-9,11-dienoate	Generator
13S-Hydroxyoctadecadienoate	HMDB
13-Hydroxy-9,11-octadecadienoic acid	HMDB
13-Hydroxy-9,11-octadecadienoic acid, (S)-(e,Z)-isomer	HMDB
13-Hydroxy-9,11-octadecadienoic acid, (Z,e)-isomer	HMDB
13-Hydroxyoctadecadienoic acid	HMDB
13-Hydroxy-9,11-octadecadienoic acid, (e,Z)-isomer	HMDB
13(S) HODE	HMDB
13-Hydroxyoctadecadienoate	HMDB
(+)-Coriolic acid	HMDB
(13S,9Z,11E)-13-Hydroxy-9,11-octadecadienoic acid	HMDB
(9Z,11E)-13-Hydroxy-9,11-octadecadienoic acid	HMDB
(9Z,11E,13S)-13-Hydroxy-9,11-octadecadienoic acid	HMDB
(9Z,11E,13S)-13-Hydroxyoctadecadienoic acid	HMDB
(S)-Coriolic acid	HMDB
(±)-coriolic acid	HMDB
13-Hydroxy-9(Z),11(e)-octadecadienoic acid	HMDB
13-Hydroxy-9,11-cis,trans-octadecadienoic acid	HMDB
13-Hydroxy-9-cis-11-trans-octadecadienoic acid	HMDB
13-Hydroxy-cis-9-trans-11-octadecadienoic acid	HMDB
13-Hydroxylinoleic acid	HMDB
13-Hydroxyoctadeca-9,11-dienoic acid	HMDB
13S-HODE	HMDB
13S-Hydroxy-9Z,11E-octadecadienoic acid	HMDB
L-13-Hydroxy-cis-9,trans-11-octadecadienoic acid	HMDB
alpha-Artemisolic acid	HMDB
Α-artemisolic acid	HMDB
(9Z,11E,13S)-13-Hydroxyoctadeca-9,11-dienoate	HMDB
(9Z,11E)-13-HODE	HMDB
(9Z,11E)-13-Hydroxyoctadecadienoic acid	HMDB
FA(18:2(9Z,11E,13-OH))	HMDB
FA(18:2(9Z,11E,13S-OH))	HMDB
13-HODE	HMDB, MeSH

Chemical Formula

C₁₈H₃₂O₃

Average Molecular Weight

296.4449

Monoisotopic Molecular Weight

296.23514489

IUPAC Name

(9Z,11E,13S)-13-hydroxyoctadeca-9,11-dienoic acid

Traditional Name

13-hydroxyoctadecadienoic acid

CAS Registry Number

5204-88-6

SMILES

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

InChI Identifier

InChI=1S/C18H32O3/c1-2-3-11-14-17(19)15-12-9-7-5-4-6-8-10-13-16-18(20)21/h7,9,12,15,17,19H,2-6,8,10-11,13-14,16H2,1H3,(H,20,21)/b9-7-,15-12+/t17-/m0/s1

InChI Key

HNICUWMFWZBIFP-IRQZEAMPSA-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
Fatty acid
Unsaturated fatty acid
Secondary alcohol
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Organic oxide
Organic oxygen compound
Alcohol
Hydrocarbon derivative
Carbonyl group
Organooxygen compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

HODE (CHEBI:34154 )
Other Octadecanoids (C14762 )
Other Octadecanoids (LMFA02000228 )

Functional Ontology

Not Available

Exogenous (HMDB: HMDB0061708)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.003 g/L	ALOGPS
logP	5.88	ALOGPS
logP	5.19	ChemAxon
logS	-5	ALOGPS
pKa (Strongest Acidic)	4.99	ChemAxon
pKa (Strongest Basic)	-1.6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	57.53 Å²	ChemAxon
Rotatable Bond Count	14	ChemAxon
Refractivity	90.03 m³·mol⁻¹	ChemAxon
Polarizability	37.26 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon