ChemFOnt: Showing chemical card for 15(S)-Hydroxyeicosatrienoic acid (CFc000002383)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:47:15 UTC

Chemfont ID

CFc000002383

Molecule Identification

Common Name

15(S)-Hydroxyeicosatrienoic acid

Definition

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 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
15(S)-Hydroxyeicosatrienoate	Generator

Chemical Formula

C₂₀H₃₄O₃

Average Molecular Weight

322.4822

Monoisotopic Molecular Weight

322.250794954

IUPAC Name

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

Traditional Name

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

CAS Registry Number

13-16-1

SMILES

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

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

Chemical Taxonomy

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

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 20671299)

Cellular substructure

Membrane (HMDB: HMDB0005045)
Extracellular (HMDB: HMDB0005045)

Source

Exogenous

Exogenous (HMDB: HMDB0005045)

Food

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)

Endogenous

Endogenous (HMDB: HMDB0005045)

Process

Not Available

Role

Not Available

Physical Properties

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

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB023608

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

3246874

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for 15(S)-Hydroxyeicosatrienoic acid (CFc000002383)

MOL for CFc000002383 (15(S)-Hydroxyeicosatrienoic acid)

3D MOL for CFc000002383 (15(S)-Hydroxyeicosatrienoic acid)

3D SDF for CFc000002383 (15(S)-Hydroxyeicosatrienoic acid)

3D-SDF for CFc000002383 (15(S)-Hydroxyeicosatrienoic acid)

PDB for CFc000002383 (15(S)-Hydroxyeicosatrienoic acid)

3D PDB for CFc000002383 (15(S)-Hydroxyeicosatrienoic acid)

SMILES for CFc000002383 (15(S)-Hydroxyeicosatrienoic acid)

INCHI for CFc000002383 (15(S)-Hydroxyeicosatrienoic acid)

Structure for CFc000002383 (15(S)-Hydroxyeicosatrienoic acid)

3D Structure for CFc000002383 (15(S)-Hydroxyeicosatrienoic acid)