Bovine Metabolome Database: Showing metabocard for Leukotriene B4 (BMDB0001085)

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Identification Taxonomy Physical properties Pathways Spectra Concentrations Links References enzymes (2) Show 2 proteins XML

Record Information

Version

1.0

Creation Date

2016-09-30 22:40:54 UTC

Update Date

2020-05-11 20:44:23 UTC

BMDB ID

BMDB0001085

Secondary Accession Numbers

BMDB01085

Metabolite Identification

Common Name

Leukotriene B4

Description

Leukotriene B4, also known as LTB4 or 5,12-dihete, belongs to the class of organic compounds known as leukotrienes. These are eicosanoids containing a hydroxyl group attached to the aliphatic chain of an arachidonic acid. Leukotrienes have four double bonds, three (and only three) of which are conjugated. Thus, leukotriene B4 is considered to be an eicosanoid lipid molecule. Leukotriene B4 is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(5S,12R,6Z,8E,10E,14Z)-5,12-Dihydroxy-6,8,10,14-eicosatetraenoic acid	ChEBI
(5S,6Z,8E,10E,12R,14Z)-5,12-Dihydroxyeicosa-6,8,10,14-tetraenoic acid	ChEBI
(S-(R,s-(e,Z,e,Z)))-5,12-dihydroxy-6,8,10,14-eicosatetraenoic acid	ChEBI
5(S),12(R)-Dihydroxy-6(Z),8(e),10(e),14(Z)-eicosatetraenoic acid	ChEBI
5(S),12(R)-Dihydroxy-6(Z),8(e),10(e),14(Z)-icosatetraenoic acid	ChEBI
5,12-Dihete	ChEBI
5,12-Hete	ChEBI
5S,12R-Dihydroxy-6Z,8E,10E,14Z-eicosatetraenoic acid	ChEBI
LTB4	ChEBI
(6Z,8E,10E,14Z)-(5S,12R)-5,12-Dihydroxyeicosa-6,8,10,14-tetraenoate	Kegg
(6Z,8E,10E,14Z)-(5S,12R)-5,12-Dihydroxyicosa-6,8,10,14-tetraenoate	Kegg
(5S,12R,6Z,8E,10E,14Z)-5,12-Dihydroxy-6,8,10,14-eicosatetraenoate	Generator
(5S,6Z,8E,10E,12R,14Z)-5,12-Dihydroxyeicosa-6,8,10,14-tetraenoate	Generator
(S-(R,s-(e,Z,e,Z)))-5,12-dihydroxy-6,8,10,14-eicosatetraenoate	Generator
5(S),12(R)-Dihydroxy-6(Z),8(e),10(e),14(Z)-eicosatetraenoate	Generator
5(S),12(R)-Dihydroxy-6(Z),8(e),10(e),14(Z)-icosatetraenoate	Generator
5S,12R-Dihydroxy-6Z,8E,10E,14Z-eicosatetraenoate	Generator
(6Z,8E,10E,14Z)-(5S,12R)-5,12-Dihydroxyeicosa-6,8,10,14-tetraenoic acid	Generator
(6Z,8E,10E,14Z)-(5S,12R)-5,12-Dihydroxyicosa-6,8,10,14-tetraenoic acid	Generator
5,12 HETE	HMDB
5,12 DiHETE	HMDB
Leukotriene b-4	HMDB
Leukotrienes b	HMDB
b-4, Leukotriene	HMDB
Leukotriene b 4	HMDB
Leukotriene b	HMDB
5,12-Dihydroxy-6,10-trans -8,14-cis -eicosatetraenoate	HMDB
5,12-Dihydroxy-6,10-trans -8,14-cis -eicosatetraenoic acid	HMDB
Leukotriene b4 ethanol solution	HMDB
(+)-Leukotriene b4	HMDB
(5S,12R)-Leukotriene b4	HMDB
5(S),12(R)-Dihydroxy-6-cis,8,10-trans,14-cis-eicosatetraenoic acid	HMDB
Leucotriene b4	HMDB
cis-Leukotriene b4	HMDB
Leukotriene B4	HMDB

Chemical Formula

C₂₀H₃₂O₄

Average Molecular Weight

336.4657

Monoisotopic Molecular Weight

336.230059512

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

71160-24-2

SMILES

Not Available

InChI Identifier

InChI=1S/C20H32O4/c1-2-3-4-5-6-9-13-18(21)14-10-7-8-11-15-19(22)16-12-17-20(23)24/h6-11,14-15,18-19,21-22H,2-5,12-13,16-17H2,1H3,(H,23,24)/b8-7+,9-6-,14-10+,15-11-/t18-,19-/m1/s1

InChI Key

VNYSSYRCGWBHLG-AMOLWHMGSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as leukotrienes. These are eicosanoids containing a hydroxyl group attached to the aliphatic chain of an arachidonic acid. Leukotrienes have four double bonds, three (and only three) of which are conjugated.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Eicosanoids

Direct Parent

Leukotrienes

Alternative Parents

Substituents

Leukotriene
Hydroxyeicosatetraenoic acid
Long-chain fatty acid
Hydroxy fatty acid
Fatty acid
Unsaturated fatty acid
Secondary alcohol
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organooxygen compound
Alcohol
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

long-chain fatty acid (CHEBI:15647 )
leukotriene (CHEBI:15647 )
dihydroxy monocarboxylic acid (CHEBI:15647 )
polyunsaturated fatty acid (CHEBI:15647 )
hydroxy fatty acid (CHEBI:15647 )
Leukotrienes (C02165 )
Leukotrienes (LMFA03020001 )

Ontology

Status

Expected but not Quantified

Origin

Endogenous

Exogenous

Biofunction

Not Available

Application

Not Available

Cellular locations

Cell membrane
Cytoplasm
Endoplasmic reticulum
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

Not Available

Spectra

Spectrum Type	Description	Splash Key

Biological Properties

Cellular Locations

Cell membrane
Cytoplasm
Endoplasmic reticulum
Membrane

Biospecimen Locations

Epidermis
Leukocyte
Platelet

Pathways

Name	SMPDB/Pathwhiz	KEGG
Arachidonic Acid Metabolism		Not Available

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
Platelet	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details

Abnormal Concentrations

Not Available

External Links

HMDB ID

HMDB0001085

DrugBank ID

DB12961

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

C02165

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Leukotriene_B4

METLIN ID

Not Available

PubChem Compound

5280492

PDB ID

Not Available

ChEBI ID

15647

References

Synthesis Reference

Han, Chao Qi; DiTullio, Dennis; Wang, Yi Fong; Sih, Charles J. A chemoenzymatic synthesis of leukotriene B4. Journal of Organic Chemistry (1986), 51(8), 1253-8.

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Enzymes

Enzyme Details

1. Leukotriene A-4 hydrolase

General function:: Amino acid transport and metabolism
Specific function:: Epoxide hydrolase that catalyzes the final step in the biosynthesis of the proinflammatory mediator leukotriene B4. Has also aminopeptidase activity (By similarity).
Gene Name:: LTA4H
Uniprot ID:: Q3SZH7
Molecular weight:: 69306.0

Enzyme Details

2. Leukotriene B4 receptor 1

General function:: Involved in G-protein coupled receptor protein signalin
Specific function:: Receptor for extracellular ATP > UTP and ADP. The activity of this receptor is mediated by G proteins which activate a phosphatidylinositol-calcium second messenger system. May be the cardiac P2Y receptor involved in the regulation of cardiac muscle contraction through modulation of L-type calcium currents. Is a receptor for leukotriene B4, a potent chemoattractant involved in inflammation and immune response (By similarity).
Gene Name:: LTB4R
Uniprot ID:: Q3T181
Molecular weight:: 37689.0

Showing metabocard for Leukotriene B4 (BMDB0001085)

Structure for BMDB0001085 (Leukotriene B4)

Enzymes