Bovine Metabolome Database: Showing metabocard for Leukotriene A4 (BMDB0001337)

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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 22:44:20 UTC

Update Date

2020-05-21 16:27:00 UTC

BMDB ID

BMDB0001337

Secondary Accession Numbers

BMDB01337

Metabolite Identification

Common Name

Leukotriene A4

Description

Leukotriene A4, also known as LTA4, belongs to the class of organic compounds known as epoxy fatty acids. These are fatty acids containing an oxirane ring as part of the aliphatic chain. Thus, leukotriene A4 is considered to be an eicosanoid lipid molecule. Leukotriene A4 is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(5S,6S,7E,9E,11Z,14Z)-5,6-Epoxyicosa-7,9,11,14-tetraenoate	ChEBI
(7E,9E,11Z,14Z)-(5S,6S)-5,6-Epoxyeicosa-7,9,11,14-tetraenoate	ChEBI
(7E,9E,11Z,14Z)-(5S,6S)-5,6-Epoxyeicosa-7,9,11,14-tetraenoic acid	ChEBI
(7E,9E,11Z,14Z)-(5S,6S)-5,6-Epoxyicosa-7,9,11,14-tetraenoate	ChEBI
5(S)-5,6-Oxido-7,9-trans-11,14-cis-eicosatetraenoic acid	ChEBI
5S,6S-Epoxy-7E,9E,11Z,14Z-eicosatetraenoic acid	ChEBI
5S,6S-Leukotriene a4	ChEBI
LTA4	ChEBI
(5S,6S,7E,9E,11Z,14Z)-5,6-Epoxyicosa-7,9,11,14-tetraenoic acid	Generator
(7E,9E,11Z,14Z)-(5S,6S)-5,6-Epoxyicosa-7,9,11,14-tetraenoic acid	Generator
5(S)-5,6-Oxido-7,9-trans-11,14-cis-eicosatetraenoate	Generator
5S,6S-Epoxy-7E,9E,11Z,14Z-eicosatetraenoate	Generator
(7E,9E,11Z,14Z)-(5S,6S)-5,6-Epoxyicosa- 7,9,11,14-tetraenoate	HMDB
(7E,9E,11Z,14Z)-(5S,6S)-5,6-Epoxyicosa- 7,9,11,14-tetraenoic acid	HMDB
(7E,9E,11Z,14Z)-(5S,6S)-5,6-Epoxyicosa-7,9,11,14-tetrenoioc acid	HMDB
Leukotriene a	HMDB
Leukotriene a 4	HMDB
Leukotrienes a	HMDB
Leukotriene a-4	HMDB

Chemical Formula

C₂₀H₃₀O₃

Average Molecular Weight

318.4504

Monoisotopic Molecular Weight

318.219494826

IUPAC Name

4-[(2S,3S)-3-[(1E,3E,5Z,8Z)-tetradeca-1,3,5,8-tetraen-1-yl]oxiran-2-yl]butanoic acid

Traditional Name

leukotriene A4

CAS Registry Number

72059-45-1

SMILES

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

InChI Identifier

InChI=1S/C20H30O3/c1-2-3-4-5-6-7-8-9-10-11-12-13-15-18-19(23-18)16-14-17-20(21)22/h6-7,9-13,15,18-19H,2-5,8,14,16-17H2,1H3,(H,21,22)/b7-6-,10-9-,12-11+,15-13+/t18-,19-/m0/s1

InChI Key

UFPQIRYSPUYQHK-WAQVJNLQSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as epoxy fatty acids. These are fatty acids containing an oxirane ring as part of the aliphatic chain.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acids and conjugates

Direct Parent

Epoxy fatty acids

Alternative Parents

Substituents

Epoxy fatty acid
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Ether
Oxirane
Dialkyl ether
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

long-chain fatty acid (CHEBI:15651 )
leukotriene (CHEBI:15651 )
polyunsaturated fatty acid (CHEBI:15651 )
oxylipin (CHEBI:15651 )
epoxy fatty acid (CHEBI:15651 )
Epoxy fatty acids (C00909 )
Leukotrienes (C00909 )
Leukotrienes (LMFA03020023 )

Ontology

Status

Expected but not Quantified

Origin

Endogenous

Exogenous

Biofunction

Not Available

Application

Not Available

Cellular locations

Adiposome
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

Property	Value	Source
logP	6.04	ALOGPS
logP	5.44	ChemAxon
logS	-5.9	ALOGPS
pKa (Strongest Acidic)	4.49	ChemAxon
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	49.83 Å²	ChemAxon
Rotatable Bond Count	13	ChemAxon
Refractivity	99.32 m³·mol⁻¹	ChemAxon
Polarizability	37.95 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

Spectrum Type	Description	Splash Key
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0uec-8290000000-c9cb5a94725e337cb3e0	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-00gr-9143000000-62d8773d6e2e97f53892	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0gb9-1129000000-fffe04743dab285e2ca8	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-052g-9421000000-f30ef9628caae676c4c0	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9610000000-5d083c3562218df21b53	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0139000000-39394fbcd6b959bb3bf7	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-01b9-4396000000-97fa16078ceabe3f07db	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-052f-9230000000-62723f520381db54d71c	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0uxr-3529000000-0fbbeee57f59de11f177	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0fyn-9533000000-d9537938ec7f6d247757	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-052f-9100000000-e99fd57f045ac7fdae48	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0009000000-144e64ffbb4253ee3d97	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014i-6339000000-eb15f4eeced3dd8bfaed	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-052f-9320000000-a3755453c278384f23ba	View in MoNA

Biological Properties

Cellular Locations

Adiposome
Cell membrane
Cytoplasm
Endoplasmic reticulum
Membrane

Biospecimen Locations

Epidermis

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

Abnormal Concentrations

Not Available

External Links

HMDB ID

HMDB0001337

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022561

KNApSAcK ID

Not Available

Chemspider ID

4444074

KEGG Compound ID

C00909

BioCyc ID

Not Available

BiGG ID

Wikipedia Link

METLIN ID

PubChem Compound

PDB ID

Not Available

ChEBI ID

15651

References

Synthesis Reference

Not Available

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

Reactions

Leukotriene A4 + Water → 6-trans-Leukotriene B4	details

Enzyme Details

2. Leukotriene C4 synthase

General function:: Involved in enzyme activator activity
Specific function:: Catalyzes the conjugation of leukotriene A4 with reduced glutathione to form leukotriene C4.
Gene Name:: LTC4S
Uniprot ID:: Q2NKS0
Molecular weight:: 16701.0

Reactions

Leukotriene A4 + Glutathione → Leukotriene C4	details

Showing metabocard for Leukotriene A4 (BMDB0001337)

Structure for BMDB0001337 (Leukotriene A4)

Enzymes

Reactions

Reactions