Showing Compound cis-8,11,14,17-Eicosatetraenoic acid (FDB022887)

Record Information

Version

1.0

Creation date

2011-09-21 00:21:09 UTC

Update date

2019-11-26 03:21:06 UTC

Primary ID

FDB022887

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

cis-8,11,14,17-Eicosatetraenoic acid

Description

Cis-8,11,14,17-Eicosatetraenoic acid is an eicosanoid present in marine lipids, a minor n-3 polyunsaturated fatty acid (PUFA) which is a position isomer of 20:4n-6. n-3 PUFA contained in marine lipids appear to have a protective effect against coronary heart disease and thrombosis. Human platelets metabolize 8,11,14,17-eicosatetraenoic acid primarily into 12-hydroxy-8,10,14,17-eicosatetraenoic acid. 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. Taken together, these findings indicate that the enzymatic conversion of eicosatrienoic acid to specific signaling molecules can occur in the nucleus, that it is regulated, and that the synthesized products may act within the nucleus. PMID: 3109494, 8142566, 16574479, 15896193, 10037447) Trans fatty acids are characteristically produced during industrial hydrogenation of plant oils. [HMDB]

CAS Number

2091-26-1

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

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Synonym	Source
(8Z,11Z,14Z,17Z)-Eicosa-8,11,14,17-tetraenoate	Generator
(8Z,11Z,14Z,17Z)-Eicosa-8,11,14,17-tetraenoic acid	ChEBI
(8Z,11Z,14Z,17Z)-Eicosatetraenoate	Generator
(8Z,11Z,14Z,17Z)-Eicosatetraenoic acid	ChEBI
(8Z,11Z,14Z,17Z)-Icosatetraenoate	Generator
(8Z,11Z,14Z,17Z)-Icosatetraenoic acid	ChEBI
(Z,Z,Z,Z)-Eicosa-8,11,14,17-tetraenoate	Generator
(Z,Z,Z,Z)-Eicosa-8,11,14,17-tetraenoic acid	ChEBI
(Z,Z,Z,Z)-Icosa-8,11,14,17-tetraenoate	Generator
(Z,Z,Z,Z)-Icosa-8,11,14,17-tetraenoic acid	ChEBI

Showing 1 to 10 of 26 entries

Predicted Properties

Property	Value	Source
Water Solubility	0.00016 g/L	ALOGPS
logP	6.83	ALOGPS
logP	6.59	ChemAxon
logS	-6.3	ALOGPS
pKa (Strongest Acidic)	4.89	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	37.3 Å²	ChemAxon
Rotatable Bond Count	14	ChemAxon
Refractivity	99.95 m³·mol⁻¹	ChemAxon
Polarizability	38.41 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

Chemical Formula

C20H32O2

IUPAC name

icosa-8,11,14,17-tetraenoic acid

InChI Identifier

InChI=1S/C20H32O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(21)22/h3-4,6-7,9-10,12-13H,2,5,8,11,14-19H2,1H3,(H,21,22)

InChI Key

HQPCSDADVLFHHO-UHFFFAOYSA-N

Isomeric SMILES

CCC=CCC=CCC=CCC=CCCCCCCC(O)=O

Average Molecular Weight

304.4669

Monoisotopic Molecular Weight

304.240230268

Classification

Description

Belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acids and conjugates

Direct Parent

Long-chain fatty acids

Alternative Parents

Substituents

Long-chain fatty acid
Unsaturated fatty acid
Straight chain fatty acid
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
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

9897310

ChEMBL ID

Not Available

KEGG Compound ID

Not Available

Pubchem Compound ID

11722594

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB02177

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

Milk (Cow)	952.484 - 1116.706 uM	1034.595 uM	M. Ferrand et al. Determination of fatty acid profile in cow's milk using mid-infrared spectrometry: Interest of applying a variable selection by genetic algorithms before a PLS regression. Chemometrics and Intelligent Laboratory Systems 106 (2011) 183?189

Showing 1 to 1 of 1 entries

Biological Effects and Interactions

Health Effects / Bioactivities

Not Available

Enzymes

Not Available

Pathways