Showing Compound 15(S)-HETE (FDB023242)

Record Information

Version

1.0

Creation date

2011-09-21 00:26:48 UTC

Update date

2015-07-21 06:57:36 UTC

Primary ID

FDB023242

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

15(S)-HETE

Description

15(S)-HETE is a hydroxyeicosatetraenoic acid. Hydroxyeicosatetraenoic acids (HETEs) are formed by the 5-, 12- and 15-lipoxygenase (LO) pathways. 5- and 12-LO products are mainly proinflammatory in the skin whereas the main 15-LO product 15-HETE has antiinflammatory capacities. In vitro 15-HETE has been shown to inhibit LTB4 formation, 12-HETE formation and specifically inhibits the neutrophil chemotactic effect of LTB4. The inhibition of LTB4 formation is probably due to modulation of the 5-LO because no changes in PGE2 formation have been determined. In vivo, 15-HETE inhibits LTB4-induced erythema and edema, and reduces LTB4 in the synovial fluid of carragheenan-induced experimental arthritis in dogs. 15-HETE has also some immunomodulatory effects. It inhibits the mixed lymphocyte reaction, induces generation of murine cytotoxic suppressor T cells, and it decreases interferon production by murine lymphoma cells. Furthermore, IL-4 and IL-13 have recently been shown to be potent activators of the 15-LO in mononuclear cells. (PMID: 11104340) [HMDB]

CAS Number

54845-95-3

Structure

MOL SDF PDB SMILES InChI

Synonyms

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Synonym	Source
(15S)-15-Hydroxy-5,8,11-cis-13-trans-eicosatetraenoate	hmdb
(15S)-15-Hydroxy-5,8,11-cis-13-trans-eicosatetraenoic acid	hmdb
(15S)-15-Hydroxy-5,8,11-cis-13-trans-eicosic acid	hmdb
(15S)-15-Hydroxy-5,8,11-cis-13-trans-icosatetraenoate	hmdb
(15S)-15-Hydroxy-5,8,11-cis-13-trans-icosatetraenoic acid	hmdb
(15S)-Hydroxy-(5Z,8Z,11Z,13e)-eicosatetraenoate	Generator
(15S)-Hydroxy-(5Z,8Z,11Z,13e)-eicosatetraenoic acid	ChEBI
(15S)-Hydroxyeicosa-(5Z,8Z,11Z,13e)-tetraenoate	Generator
(15S)-Hydroxyeicosa-(5Z,8Z,11Z,13e)-tetraenoic acid	ChEBI
(15S,5Z,8Z,11Z,13E)-15-Hydroxyeicosatetraenoate	hmdb

Showing 1 to 10 of 28 entries

Predicted Properties

Property	Value	Source
Water Solubility	0.002 g/L	ALOGPS
logP	5.82	ALOGPS
logP	5.36	ChemAxon
logS	-5.2	ALOGPS
pKa (Strongest Acidic)	4.82	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	101.47 m³·mol⁻¹	ChemAxon
Polarizability	38.76 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

Chemical Formula

C20H32O3

IUPAC name

(15S)-15-hydroxyicosa-5,8,11,13-tetraenoic acid

InChI Identifier

InChI=1S/C20H32O3/c1-2-3-13-16-19(21)17-14-11-9-7-5-4-6-8-10-12-15-18-20(22)23/h4-5,8-11,14,17,19,21H,2-3,6-7,12-13,15-16,18H2,1H3,(H,22,23)/t19-/m0/s1

InChI Key

JSFATNQSLKRBCI-IBGZPJMESA-N

Isomeric SMILES

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

Average Molecular Weight

320.4663

Monoisotopic Molecular Weight

320.23514489

Classification

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

Ontology

No ontology term

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

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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

ChEMBL ID

KEGG Compound ID

Pubchem Compound ID

Pubchem Substance ID

Not Available

ChEBI ID

15558

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB03876

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

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Food	Content Range	Average	Reference

Processing...

Biological Effects and Interactions

Health Effects / Bioactivities

Not Available

Enzymes

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Name	Gene Name	UniProt ID
Epididymal secretory glutathione peroxidase	GPX5	O75715
Glutathione peroxidase 1	GPX1	P07203
Glutathione peroxidase 2	GPX2	P18283
Glutathione peroxidase 3	GPX3	P22352
Glutathione peroxidase 6	GPX6	P59796
Glutathione peroxidase 7	GPX7	Q96SL4
Phospholipid hydroperoxide glutathione peroxidase, mitochondrial	GPX4	P36969