Showing Compound 11,12-DiHETrE (FDB022961)

Record Information

Version

1.0

Creation date

2011-09-21 00:22:25 UTC

Update date

2015-07-21 06:57:26 UTC

Primary ID

FDB022961

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

11,12-DiHETrE

Description

11,12-DiHETrE is a Cytochrome P450 (P450) eicosanoid. Arachidonic acid may be oxygenated by cytochrome P450 in several ways. Epoxidation of the double bonds leads to the regio- and enantioselective formation of four epoxyeicosatrienoic acids (EETs), which are hydrolyzed by epoxide hydrolase to vicinal diols (DHETs). 11,12-DiHETrE excretion is increased in healthy pregnant women compared with nonpregnant female volunteers, and increased even further in patients with pregnancy-induced hypertension (PIH). The physiological significance of arachidonic acid epoxides has been debated and it is unknown whether they play a role in pregnancy and parturition. Vasodilative effects, inhibition of cyclooxygenase, or inhibition of platelet aggregation by EETs have been observed only at micromolar concentrations. On the other hand, effects on the stimulus-secretion coupling during hormone release have been found in the nanomolar and picomolar range. (PMID: 9440131, 2198572) [HMDB]

CAS Number

192461-95-3

Structure

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

Synonyms

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Synonym	Source
(+/-)-11,12-dihydroxy-5Z,8Z,14Z,17Z-eicosatetraenoate	hmdb
(+/-)-11,12-dihydroxy-5Z,8Z,14Z,17Z-eicosatetraenoic acid	hmdb
(+/-)11,12-dihetre	ChEBI
(5Z,8Z,14Z)-11,12-Dihydroxyeicosa-5,8,14-trienoate	hmdb
(5Z,8Z,14Z)-11,12-Dihydroxyeicosa-5,8,14-trienoic acid	hmdb
(5Z,8Z,14Z)-11,12-Dihydroxyicosa-5,8,14-trienoate	hmdb
(5Z,8Z,14Z)-11,12-Dihydroxyicosa-5,8,14-trienoic acid	hmdb
11,12-DHET	hmdb
11,12-DHETA	MeSH
11,12-Dihydroxy-5,8,14-eicosatrienoic acid	MeSH

Showing 1 to 10 of 16 entries

Predicted Properties

Property	Value	Source
Water Solubility	0.013 g/L	ALOGPS
logP	5.41	ALOGPS
logP	4.49	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Acidic)	4.82	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	77.76 Å²	ChemAxon
Rotatable Bond Count	15	ChemAxon
Refractivity	101.87 m³·mol⁻¹	ChemAxon
Polarizability	40.48 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

C20H34O4

IUPAC name

11,12-dihydroxyicosa-5,8,14-trienoic acid

InChI Identifier

InChI=1S/C20H34O4/c1-2-3-4-5-9-12-15-18(21)19(22)16-13-10-7-6-8-11-14-17-20(23)24/h6,8-10,12-13,18-19,21-22H,2-5,7,11,14-17H2,1H3,(H,23,24)

InChI Key

LRPPQRCHCPFBPE-UHFFFAOYSA-N

Isomeric SMILES

CCCCCC=CCC(O)C(O)CC=CCC=CCCCC(O)=O

Average Molecular Weight

338.4816

Monoisotopic Molecular Weight

338.245709576

Classification

Description

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

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Eicosanoids

Direct Parent

Hydroxyeicosatrienoic acids

Alternative Parents

Substituents

Hydroxyeicosatrienoic acid
Long-chain fatty acid
Hydroxy fatty acid
Unsaturated fatty acid
Fatty acid
Secondary alcohol
1,2-diol
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
Alcohol
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

4446270

ChEMBL ID

Not Available

KEGG Compound ID

C14774

Pubchem Compound ID

5283146

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB02314

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

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 11,12-DiHETrE (FDB022961)

Structure for FDB022961 (11,12-DiHETrE)