Showing Compound 5-HEPE (FDB023620)

Record Information

Version

1.0

Creation date

2011-09-21 00:32:30 UTC

Update date

2018-05-28 18:36:48 UTC

Primary ID

FDB023620

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

5-HEPE

Description

5-HEPE is a major eicosanoid formed from eicosapentaenoic acid (EPA). 5-HEPE is produced in human neutrophils. The eicosanoids are a diverse family of molecules that have powerful effects on cell function. They are best known as intercellular messengers, having autocrine and paracrine effects following their secretion from the cells that synthesize them. The diversity of possible products that can be synthesized from eicosatrienoic acid is due, in part to the variety of enzymes that can act on it. Studies have placed many, but not all, of these enzymes at or inside the nucleus. In some cases, the nuclear import or export of eicosatrienoic acid-processing enzymes is highly regulated. Furthermore, nuclear receptors that are activated by specific eicosanoids are known to exist. (PMID: 8847485, 15896193) [HMDB]

CAS Number

92008-51-0

Structure

MOL SDF PDB SMILES InChI

Synonyms

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Synonym	Source
(+-)-5-HEPE	ChEBI
(+-)-5-Hydroxy-6e,8Z,11Z,14Z,17Z-eicosapentaenoate	Generator
(+-)-5-Hydroxy-6e,8Z,11Z,14Z,17Z-eicosapentaenoic acid	ChEBI
(+/-)-5-HEPE	hmdb
(+/-)-5-hydroxy-6E,8Z,11Z,14Z,17Z-eicosapentaenoate	hmdb
(+/-)-5-hydroxy-6E,8Z,11Z,14Z,17Z-eicosapentaenoic acid	hmdb
5-Hepe	hmdb
5-Hydroxy-6,8,11,14,17-eicosapentaenoate	hmdb
5-Hydroxy-6,8,11,14,17-eicosapentaenoic acid	hmdb
5-Hydroxyeicosapentaenoate	hmdb

Showing 1 to 10 of 11 entries

Predicted Properties

Property	Value	Source
Water Solubility	0.0029 g/L	ALOGPS
logP	5.54	ALOGPS
logP	4.99	ChemAxon
logS	-5	ALOGPS
pKa (Strongest Acidic)	4.58	ChemAxon
pKa (Strongest Basic)	-1.5	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	13	ChemAxon
Refractivity	102.59 m³·mol⁻¹	ChemAxon
Polarizability	38.51 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

Chemical Formula

C20H30O3

IUPAC name

(6E)-5-hydroxyicosa-6,8,11,14,17-pentaenoic acid

InChI Identifier

InChI=1S/C20H30O3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-16-19(21)17-15-18-20(22)23/h3-4,6-7,9-10,12-14,16,19,21H,2,5,8,11,15,17-18H2,1H3,(H,22,23)/b4-3?,7-6?,10-9?,13-12?,16-14+

InChI Key

FTAGQROYQYQRHF-OTZRFASISA-N

Isomeric SMILES

CCC=CCC=CCC=CCC=C\C=C\C(O)CCCC(O)=O

Average Molecular Weight

318.4504

Monoisotopic Molecular Weight

318.219494826

Classification

Description

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

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Eicosanoids

Direct Parent

Hydroxyeicosapentaenoic acids

Alternative Parents

Substituents

Hydroxyeicosapentaenoic 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

4944072

ChEMBL ID

Not Available

KEGG Compound ID

Not Available

Pubchem Compound ID

6439678

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB05081

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

Not Available

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Not Available

Files

MSDS

Not Available

References

Synthesis Reference

Not Available

General Reference

Not Available

Content Reference

Showing Compound 5-HEPE (FDB023620)

Structure for FDB023620 (5-HEPE)