Bovine Metabolome Database: Showing metabocard for Hepoxilin A3 (BMDB0004688)

Identification Taxonomy Physical properties Pathways Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-09-30 23:10:16 UTC

Update Date

2020-05-11 20:19:58 UTC

BMDB ID

BMDB0004688

Secondary Accession Numbers

BMDB04688

Metabolite Identification

Common Name

Hepoxilin A3

Description

Hepoxilin A3, also known as hexophilin A3 or HXA3 CPD, belongs to the class of organic compounds known as hepoxilins. These are eicosanoids containing an oxirane group attached to the fatty acyl chain. Thus, hepoxilin A3 is considered to be an eicosanoid. Based on a literature review a significant number of articles have been published on Hepoxilin A3.

Structure

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

Synonyms

Value	Source
(5Z,9E,14Z)-(8XI,11R,12S)-11,12-epoxy-8-hydroxyeicosa-5,9,14-trienoic acid	ChEBI
(5Z,9E,14Z)-(8XI,11R,12S)-11,12-epoxy-8-hydroxyeicosa-5,9,14-trienoate	Generator
11,12-Epoxy-8-hydroxyeicosa-5,9,14-trienoate	HMDB
8-Hydroxy-11,12-epoxyeicosa-5,9,14-trienoic acid	HMDB
Hexophilin a3	HMDB
HXA3 CPD	HMDB
8-EH-2	HMDB
Hepoxilin a	HMDB
(5Z,9E)-8-Hydroxy-10-{(2S,3S)-3-[(2Z)-oct-2-en-1-yl]oxiran-2-yl}deca-5,9-dienoate	HMDB
(5Z,9E)-8-Hydroxy-10-{(2S,3S)-3-[(2Z)-oct-2-en-1-yl]oxiran-2-yl}deca-5,9-dienoic acid	HMDB
(5Z,9E,14Z)-(11S,12S)-11,12-Epoxy-8-hydroxyeicosa-5,9,14-trienoate	HMDB
(5Z,9E,14Z)-(11S,12S)-11,12-Epoxy-8-hydroxyeicosa-5,9,14-trienoic acid	HMDB
(5Z,9E,14Z)-(11S,12S)-11,12-Epoxy-8-hydroxyicosa-5,9,14-trienoate	HMDB
(5Z,9E,14Z)-(11S,12S)-11,12-Epoxy-8-hydroxyicosa-5,9,14-trienoic acid	HMDB
8-Hydroxy-11,12-epoxyeicosa-5,9,14-trienoate	HMDB
8-Hydroxy-11S,12S-epoxy-5Z,14Z,9E-eicosatrienoate	HMDB
8-Hydroxy-11S,12S-epoxy-5Z,14Z,9E-eicosatrienoic acid	HMDB
(5Z,9E,14Z)-(8XI,11R,12S)-11,12-epoxy-8-hydroxyicosa-5,9,14-trienoate	HMDB
Hepoxilin a3	MeSH

Chemical Formula

C₂₀H₃₂O₄

Average Molecular Weight

336.4657

Monoisotopic Molecular Weight

336.230059512

IUPAC Name

(5Z,9E)-8-hydroxy-10-[(2R,3S)-3-[(2Z)-oct-2-en-1-yl]oxiran-2-yl]deca-5,9-dienoic acid

Traditional Name

HXA3 cpd

CAS Registry Number

85589-24-8

SMILES

CCCCC\C=C/C[C@@H]1O[C@@H]1\C=C\C(O)C\C=C/CCCC(O)=O

InChI Identifier

InChI=1S/C20H32O4/c1-2-3-4-5-6-10-13-18-19(24-18)16-15-17(21)12-9-7-8-11-14-20(22)23/h6-7,9-10,15-19,21H,2-5,8,11-14H2,1H3,(H,22,23)/b9-7-,10-6-,16-15+/t17?,18-,19+/m0/s1

InChI Key

SGTUOBURCVMACZ-CIQDQOFUSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as hepoxilins. These are eicosanoids containing an oxirane group attached to the fatty acyl chain.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Eicosanoids

Direct Parent

Hepoxilins

Alternative Parents

Substituents

Hepoxilin
Medium-chain hydroxy acid
Medium-chain fatty acid
Epoxy fatty acid
Heterocyclic fatty acid
Hydroxy fatty acid
Fatty acid
Unsaturated fatty acid
Secondary alcohol
Carboxylic acid derivative
Carboxylic acid
Dialkyl ether
Oxirane
Ether
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Organic oxide
Hydrocarbon derivative
Carbonyl group
Alcohol
Organic oxygen compound
Organooxygen compound
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

long-chain fatty acid (CHEBI:15631 )
epoxy fatty acid (CHEBI:15631 )
trienoic fatty acid (CHEBI:15631 )
hydroxy fatty acid (CHEBI:15631 )
Epoxyeicosatrienoic acids (LMFA03080012 )

Ontology

Status

Expected but not Quantified

Origin

Endogenous

Exogenous

Biofunction

Not Available

Application

Not Available

Cellular locations

Cell membrane
Cytoplasm
Membrane

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	5.57	ALOGPS
logP	4.57	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Acidic)	4.68	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	70.06 Å²	ChemAxon
Rotatable Bond Count	14	ChemAxon
Refractivity	99.72 m³·mol⁻¹	ChemAxon
Polarizability	38.57 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Biological Properties

Cellular Locations

Cell membrane
Cytoplasm
Membrane

Biospecimen Locations

Epidermis
Leukocyte

Pathways

Not Available

Name	SMPDB/Pathwhiz	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Epidermis	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Leukocyte	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details