ChemFOnt: Showing chemical card for 11-Hydroxyeicosatetraenoate glyceryl ester (CFc000008022)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:54:38 UTC

Chemfont ID

CFc000008022

Molecule Identification

Common Name

11-Hydroxyeicosatetraenoate glyceryl ester

Definition

11(R)-HETE is produced from arachidonic acid by both COX-1 and COX-2 (cyclooxygenases). Using a model of intestinal epithelial cells that express the COX-2 permanently, 11(R)-HETE is produced upon stimulation. However, 11(R)-HETE is not detected in intact cells. Endothelial cells release several factors which influence vascular tone, leukocyte function and platelet aggregation; 11(R)-HETE is one of these factors. (PMID: 15964853 , 8555273 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
11-Hydroxyeicosatetraenoic acid glyceryl ester	Generator
(11S)-Hydroxy-(5Z,8Z,12E,14Z)-eicosatetraenoyl-2-glyceryl ester	HMDB
(5Z,8Z,12E,14Z)-11S-Hydroxyeicosatetraenoyl-2-glyceryl ester	HMDB
11-HETE-g	HMDB
2-[(11S)-Hydroxy-(5Z,8Z,12E,14Z)-eicosatetraenoyl]-glycerol	HMDB
1,3-Dihydroxypropan-2-yl (5Z,8Z,11S,12E,14Z)-11-hydroxyicosa-5,8,12,14-tetraenoic acid	Generator

Chemical Formula

C₂₃H₃₈O₅

Average Molecular Weight

394.5448

Monoisotopic Molecular Weight

394.271924326

IUPAC Name

1,3-dihydroxypropan-2-yl (5Z,8Z,11S,12E,14Z)-11-hydroxyicosa-5,8,12,14-tetraenoate

Traditional Name

1,3-dihydroxypropan-2-yl (5Z,8Z,11S,12E,14Z)-11-hydroxyicosa-5,8,12,14-tetraenoate

CAS Registry Number

73347-43-0

SMILES

CCCCC\C=C/C=C/[C@@H](O)C\C=C/C\C=C/CCCC(=O)OC(CO)CO

InChI Identifier

InChI=1S/C23H38O5/c1-2-3-4-5-7-10-13-16-21(26)17-14-11-8-6-9-12-15-18-23(27)28-22(19-24)20-25/h6-7,9-11,13-14,16,21-22,24-26H,2-5,8,12,15,17-20H2,1H3/b9-6-,10-7-,14-11-,16-13+/t21-/m1/s1

InChI Key

SSHLWLAPLZCWOT-XYOZOUKRSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as endocannabinoids. These are arachidonic acid derivatives containing either an N-acetylethanolamine(type 1) or a glycerol(types 2 and 3) moiety attached to the aliphatic tail.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Endocannabinoids

Sub Class

Not Available

Direct Parent

Endocannabinoids

Alternative Parents

Substituents

2-arachidonoylglycerol-skeleton
Hydroxyeicosapolyenoic acid
Eicosanoid
Fatty alcohol
2-acyl-sn-glycerol
Monoradylglycerol
Monoacylglycerol
Glycerolipid
Fatty acid ester
Fatty acyl
Carboxylic acid ester
Secondary alcohol
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Primary alcohol
Alcohol
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
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

Route of exposure

Enteral

Ingestion (HMDB: HMDB0012530)

Source

Endogenous

Endogenous (HMDB: HMDB0012530)

Animal

Animal (HMDB: HMDB0012530)

Exogenous

Food

Food (HMDB: HMDB0012530)

Exogenous (HMDB: HMDB0012530)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0012530)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0012530)

Lipid metabolism pathway (HMDB: HMDB0012530)

Cellular process

Cell signaling (HMDB: HMDB0012530)

Biochemical process

Lipid transport (HMDB: HMDB0012530)

Role

Biological role

Energy source (HMDB: HMDB0012530)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0012530)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.0099 g/L	ALOGPS
logP	4.62	ALOGPS
logP	4.18	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Acidic)	14.28	ChemAxon
pKa (Strongest Basic)	-1.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	86.99 Å²	ChemAxon
Rotatable Bond Count	18	ChemAxon
Refractivity	118.49 m³·mol⁻¹	ChemAxon
Polarizability	45.89 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

HMDB0012530

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB029112

KNApSAcK ID

Not Available

Chemspider ID

30776620

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

53481455

PDB ID

Not Available

ChEBI ID

171687

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for 11-Hydroxyeicosatetraenoate glyceryl ester (CFc000008022)

MOL for CFc000008022 (11-Hydroxyeicosatetraenoate glyceryl ester)

3D MOL for CFc000008022 (11-Hydroxyeicosatetraenoate glyceryl ester)

3D SDF for CFc000008022 (11-Hydroxyeicosatetraenoate glyceryl ester)

3D-SDF for CFc000008022 (11-Hydroxyeicosatetraenoate glyceryl ester)

PDB for CFc000008022 (11-Hydroxyeicosatetraenoate glyceryl ester)

3D PDB for CFc000008022 (11-Hydroxyeicosatetraenoate glyceryl ester)

SMILES for CFc000008022 (11-Hydroxyeicosatetraenoate glyceryl ester)

INCHI for CFc000008022 (11-Hydroxyeicosatetraenoate glyceryl ester)

Structure for CFc000008022 (11-Hydroxyeicosatetraenoate glyceryl ester)

3D Structure for CFc000008022 (11-Hydroxyeicosatetraenoate glyceryl ester)