Showing Compound 15(S)-Hydroxyeicosatrienoic acid (FDB023608)

Record Information

Version

1.0

Creation date

2011-09-21 00:32:21 UTC

Update date

2015-07-21 06:57:47 UTC

Primary ID

FDB023608

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

15(S)-Hydroxyeicosatrienoic acid

Description

15(S)-hydroxyeicosatrienoic acid (15S-HETrE) is the in vivo metabolite of gamma-linolenic acid, a polyunsaturated fatty acid that have been reported to modulate arachidonic acid (AA) metabolism and tumorigenesis. 15S-HETrE suppress cyclooxygenase-2 (COX-2) over expression and/or Prostaglandin E2 (PGE2) biosynthesis (PMID 15197770), and inhibits [(3)H]thymidine uptake in parallel with the upregulation of peroxisome proliferator-activated receptor-gamma expression (a growth modulating nuclear receptor, PPARgamma). (PMID 12445673) [HMDB]

CAS Number

13-16-1

Structure

MOL SDF PDB SMILES InChI

Synonyms

Show entries

Search:

Synonym	Source
15(S)-Hydroxyeicosatrienoate	Generator
15(S)-hydroxyeicosatrienoate	hmdb
15(S)-hydroxyeicosatrienoic acid	hmdb
15-HETrE	hmdb
15-hydroxy-(8Z,11Z,13E)-eicosatrienoate	hmdb
15-hydroxy-(8Z,11Z,13E)-eicosatrienoic acid	hmdb
15-hydroxy-cis,cis,trans-8,11,13-eicosatrienoate	hmdb
15-hydroxy-cis,cis,trans-8,11,13-eicosatrienoic acid	hmdb
15-hydroxyeicosatrienoate	hmdb
15-hydroxyeicosatrienoic acid	hmdb

Showing 1 to 10 of 13 entries

Predicted Properties

Property	Value	Source
Water Solubility	0.0009 g/L	ALOGPS
logP	6.2	ALOGPS
logP	5.72	ChemAxon
logS	-5.6	ALOGPS
pKa (Strongest Acidic)	4.89	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	15	ChemAxon
Refractivity	100.35 m³·mol⁻¹	ChemAxon
Polarizability	40.98 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C20H34O3

IUPAC name

(15S)-15-hydroxyicosa-8,11,13-trienoic acid

InChI Identifier

InChI=1S/C20H34O3/c1-2-3-13-16-19(21)17-14-11-9-7-5-4-6-8-10-12-15-18-20(22)23/h4-5,9,11,14,17,19,21H,2-3,6-8,10,12-13,15-16,18H2,1H3,(H,22,23)/t19-/m0/s1

InChI Key

IUKXMNDGTWTNTP-IBGZPJMESA-N

Isomeric SMILES

[H][C@](O)(CCCCC)C=CC=CCC=CCCCCCCC(O)=O

Average Molecular Weight

322.4822

Monoisotopic Molecular Weight

322.250794954

Classification

Description

Belongs to the class of organic compounds known as hydroxyeicosatrienoic acids. These are eicosanoic acids with an attached hydroxyl group and three CC double bonds.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Eicosanoids

Direct Parent

Hydroxyeicosatrienoic acids

Alternative Parents

Substituents

Hydroxyeicosatrienoic acid
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

Not Available

Ontology

No ontology term

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

Show entries

Search:

Property	Value	Reference
Boiling Point	Not Available
Charge	Not Available
Density	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Experimental Water Solubility	Not Available
Isoelectric point	Not Available
Mass Composition	Not Available
Melting Point	Not Available
Optical Rotation	Not Available

Showing 1 to 10 of 14 entries

Spectra

Not Available

External Links

ChemSpider ID

4446269

ChEMBL ID

Not Available

KEGG Compound ID

Not Available

Pubchem Compound ID

5283145

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB05045

CRC / DFC (Dictionary of Food Compounds) ID

Not Available

EAFUS ID

Not Available

Dr. Duke ID

Not Available

BIGG ID

Not Available

KNApSAcK ID

Not Available

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

Not Available

Wikipedia ID

Not Available

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

Show entries

Search:

Food	Content Range	Average	Reference

Anatidae	Expected but not quantified	Not Available	HMDB
Beefalo	Expected but not quantified	Not Available	HMDB
Bison	Expected but not quantified	Not Available	HMDB
Buffalo	Expected but not quantified	Not Available	HMDB
Cattle (Beef, Veal)	Expected but not quantified	Not Available	HMDB
Chicken	Expected but not quantified	Not Available	HMDB
Columbidae (Dove, Pigeon)	Expected but not quantified	Not Available	HMDB
Deer	Expected but not quantified	Not Available	HMDB
Domestic goat	Expected but not quantified	Not Available	HMDB
Domestic pig	Expected but not quantified	Not Available	HMDB