ChemFOnt: Showing chemical card for 13-HETE (CFc000008041)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:54:39 UTC

Chemfont ID

CFc000008041

Molecule Identification

Common Name

13-HETE

Definition

13-Hydroxyeicosatetraenoic acid is one of the main metabolites of 15-lipoxygenases (15-LOXs), are endogenous ligands of PPARr. It can inhibit cell proliferation and induce apoptosis in several types of human cancer. 13-HETE is an arachidonic acid metabolite in rat liver microsomes, and is a metabolite of red algae.Hydroxyeicosatetraenoic acids (HETEs) are formed in numerous cell types by enzymatically-mediated hydroxylation of arachidonic acid. There are three distinct enzymes involved in HETE biosynthesis:lipoxygenase (LOX), prostaglandin H (PGH) synthase, and cytochrome P-450. LOX- and PGH-synthase-mediated arachidonic acid metabolism is normally highly stereoselective.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(5Z,8Z,11Z,14Z)-13-Hydroxyicosatetraenoic acid	ChEBI
13-Hydroxy-(5Z,8Z,11Z,14Z)-eicosatetraenoic acid	ChEBI
13-Hydroxy-(5Z,8Z,11Z,14Z)-icosatetraenoic acid	ChEBI
13-Hydroxyeicosatetraenoic acid	ChEBI
(5Z,8Z,11Z,14Z)-13-Hydroxyicosatetraenoate	Generator
13-Hydroxy-(5Z,8Z,11Z,14Z)-eicosatetraenoate	Generator
13-Hydroxy-(5Z,8Z,11Z,14Z)-icosatetraenoate	Generator
13-Hydroxyeicosatetraenoate	Generator
13-Hydroxy-5Z,8Z,11Z,14Z-eicosatetraenoate	HMDB
13-Hydroxy-5Z,8Z,11Z,14Z-eicosatetraenoic acid	HMDB
13-Hydroxyeicosatetraenoic acid, (S)-(all-Z)-isomer	MeSH, HMDB

Chemical Formula

C₂₀H₃₂O₃

Average Molecular Weight

320.4663

Monoisotopic Molecular Weight

320.23514489

IUPAC Name

(5Z,8Z,11Z,14Z)-13-hydroxyicosa-5,8,11,14-tetraenoic acid

Traditional Name

(5Z,8Z,11Z,14Z)-13-hydroxyicosa-5,8,11,14-tetraenoic acid

CAS Registry Number

151910-72-4

SMILES

CCCCC\C=C/C(O)\C=C/C\C=C/C\C=C/CCCC(O)=O

InChI Identifier

InChI=1S/C20H32O3/c1-2-3-4-10-13-16-19(21)17-14-11-8-6-5-7-9-12-15-18-20(22)23/h6-9,13-14,16-17,19,21H,2-5,10-12,15,18H2,1H3,(H,22,23)/b8-6-,9-7-,16-13-,17-14-

InChI Key

SAKQICHVWOJSNI-BWWNDVLWSA-N

Chemical Taxonomy

Description

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

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Eicosanoids

Direct Parent

Hydroxyeicosatetraenoic acids

Alternative Parents

Substituents

Hydroxyeicosatetraenoic 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

Cellular substructure

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0012567)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0012567)

Source

Endogenous

Endogenous (HMDB: HMDB0012567)

Animal

Animal (HMDB: HMDB0012567)

Exogenous

Food

Food (HMDB: HMDB0012567)

Exogenous (HMDB: HMDB0012567)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0012567)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0012567)

Lipid metabolism pathway (HMDB: HMDB0012567)

Cellular process

Cell signaling (HMDB: HMDB0012567)

Biochemical process

Lipid transport (HMDB: HMDB0012567)

Role

Biological role

Energy source (HMDB: HMDB0012567)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0012567)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.0016 g/L	ALOGPS
logP	5.82	ALOGPS
logP	5.51	ChemAxon
logS	-5.3	ALOGPS
pKa (Strongest Acidic)	4.82	ChemAxon
pKa (Strongest Basic)	-1.9	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	101.32 m³·mol⁻¹	ChemAxon
Polarizability	38.02 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

External Links

HMDB ID

HMDB0012567

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB029131

KNApSAcK ID

Not Available

Chemspider ID

35032542

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

53481471

PDB ID

Not Available

ChEBI ID

137345

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for 13-HETE (CFc000008041)

MOL for CFc000008041 (13-HETE)

3D MOL for CFc000008041 (13-HETE)

3D SDF for CFc000008041 (13-HETE)

3D-SDF for CFc000008041 (13-HETE)

PDB for CFc000008041 (13-HETE)

3D PDB for CFc000008041 (13-HETE)

SMILES for CFc000008041 (13-HETE)

INCHI for CFc000008041 (13-HETE)

Structure for CFc000008041 (13-HETE)

3D Structure for CFc000008041 (13-HETE)