Showing Compound Trioxilin A3 (FDB022775)

Record Information

Version

1.0

Creation date

2011-09-21 00:19:26 UTC

Update date

2015-07-21 06:57:21 UTC

Primary ID

FDB022775

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Trioxilin A3

Description

Trioxilin A3 is the enzymatically formed derivative of Hepoxilin A3. Normal human epidermis incubated with exogenous AA produces 12-oxo-eicosatetraenoic acid (12-oxo-ETE), hepoxilin A3 (HxA3), and hepoxilin B3 (HxB3) through the 12- Lipoxygenase (LO) pathway. 12-LO is the major arachidonic acid (AA) oxygenation pathway in epidermal cells with total product formation generally exceeding cyclooxygenase activity. Platelet-type 12-LO has been found to be the predominant isoenzyme expressed in human and murine skin epidermis. Increased levels of nonesterified hepoxilins and trioxilins occur in the psoriatic scales. Normal human epidermis synthesized only one of the two possible 10-hydroxy epimers of HxB3 whose formation is probably catalyzed by 12-LO. Hepoxilins exert action on plasma permeability on skin, and induce a specific-receptor-dependent Ca2+ mobilization from endogenous sources and the release of AA and diacylglycerols. (PMID: 11851887) [HMDB]

CAS Number

68860-46-8

Structure

MOL SDF PDB SMILES InChI

Synonyms

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Synonym	Source
(5Z,9E,11R,12S,14Z)-8,11,12-trihydroxyicosa-5,9,14-trienoate	hmdb
(5Z,9E,11R,12S,14Z)-8,11,12-trihydroxyicosa-5,9,14-trienoic acid	hmdb
(5Z,9E,14Z)-(11R,12S)-8,11,12-Trihydroxyeicosa-5,9,14-trienoate	hmdb
(5Z,9E,14Z)-(11R,12S)-8,11,12-Trihydroxyeicosa-5,9,14-trienoic acid	hmdb
(5Z,9E,14Z)-(11R,12S)-8,11,12-Trihydroxyicosa-5,9,14-trienoate	hmdb
(5Z,9E,14Z)-(11R,12S)-8,11,12-Trihydroxyicosa-5,9,14-trienoic acid	hmdb
(8,11R,12S)-OH 5c9t14t-20:3	ChEBI
(8,11R,12S)-OH 5c9t14t-C20:3	ChEBI
8,11,12-TETA	MeSH
8,11,12-Teta	hmdb

Showing 1 to 10 of 18 entries

Predicted Properties

Property	Value	Source
Water Solubility	0.047 g/L	ALOGPS
logP	4.53	ALOGPS
logP	3.41	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Acidic)	4.68	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	97.99 Å²	ChemAxon
Rotatable Bond Count	15	ChemAxon
Refractivity	103.23 m³·mol⁻¹	ChemAxon
Polarizability	42.34 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

C20H34O5

IUPAC name

(11R,12S)-8,11,12-trihydroxyicosa-5,9,14-trienoic acid

InChI Identifier

InChI=1S/C20H34O5/c1-2-3-4-5-6-10-13-18(22)19(23)16-15-17(21)12-9-7-8-11-14-20(24)25/h6-7,9-10,15-19,21-23H,2-5,8,11-14H2,1H3,(H,24,25)/t17?,18-,19+/m0/s1

InChI Key

WPLPEZUSILBTGP-JLMCIHFGSA-N

Isomeric SMILES

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

Average Molecular Weight

354.481

Monoisotopic Molecular Weight

354.240624198

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
Fatty acid
Unsaturated fatty acid
Secondary alcohol
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Polyol
Organic oxide
Organic oxygen compound
Hydrocarbon derivative
Carbonyl group
Organooxygen compound
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

4446329

ChEMBL ID

Not Available

KEGG Compound ID

C14809

Pubchem Compound ID

5283208

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB01977

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

Anatidae	Expected but not quantified	Not Available	HMDB
Beefalo	Expected but not quantified	Not Available	HMDB
Bison	Expected but not quantified	Not Available	HMDB
Buffalo	Expected but not quantified	Not Available	HMDB
Cattle (Beef, Veal)	Expected but not quantified	Not Available	HMDB
Chicken	Expected but not quantified	Not Available	HMDB
Columbidae (Dove, Pigeon)	Expected but not quantified	Not Available	HMDB
Deer	Expected but not quantified	Not Available	HMDB
Domestic goat	Expected but not quantified	Not Available	HMDB
Domestic pig	Expected but not quantified	Not Available	HMDB