Bovine Metabolome Database: Showing metabocard for 20-Carboxyleukotriene B4 (BMDB0006059)

Identification Taxonomy Physical properties Pathways Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-09-30 23:20:03 UTC

Update Date

2020-04-22 15:16:49 UTC

BMDB ID

BMDB0006059

Secondary Accession Numbers

BMDB06059

Metabolite Identification

Common Name

20-Carboxyleukotriene B4

Description

20-Carboxy-leukotriene B4, also known as 20-COOH-LTB4 or 20-carboxy-LTB4, belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms. Thus, 20-carboxy-leukotriene B4 is considered to be an eicosanoid. Based on a literature review a significant number of articles have been published on 20-Carboxy-leukotriene B4.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
20-Carboxy-LTB4	ChEBI
20-COOH-Leukotriene b4	ChEBI
20-COOH-LTB4	ChEBI
5,12-Dihydroxy-delta5,8,11,14-eicosapolyendioic acid	ChEBI
5,12-Dihydroxy-delta5,8,11,14-eicosapolyendioate	Generator
5,12-Dihydroxy-δ5,8,11,14-eicosapolyendioate	Generator
5,12-Dihydroxy-δ5,8,11,14-eicosapolyendioic acid	Generator
(5S,6Z,8E,10E,12R,14Z)-5,12-Dihydroxyicosa-6,8,10,14-tetraenedioate	HMDB
(5S,6Z,8E,10E,12R,14Z)-5,12-Dihydroxyicosa-6,8,10,14-tetraenedioic acid	HMDB
(S-(R,s-(e,Z,e,Z)))-5,12-dihydroxy-6,8,10,14-eicosatetraenedioate	HMDB
(S-(R,s-(e,Z,e,Z)))-5,12-dihydroxy-6,8,10,14-eicosatetraenedioic acid	HMDB
20-Carboxy-leukotriene- b4	HMDB
20-Carboxyleukotriene b4	HMDB
20-Hydroxy-20-oxo-leukotriene b4	HMDB
5(S),12(R)-Dihydroxy-20-carboxy-6,8,10,14-eicosatetraenoate	HMDB
5(S),12(R)-Dihydroxy-20-carboxy-6,8,10,14-eicosatetraenoic acid	HMDB
5S,12R-Dihydroxy-6Z,8E,10E,14Z-eicosatetraene-1,20-dioate	HMDB
5S,12R-Dihydroxy-6Z,8E,10E,14Z-eicosatetraene-1,20-dioic acid	HMDB
20-COOH LTB4	HMDB

Chemical Formula

C₂₀H₃₀O₆

Average Molecular Weight

366.4486

Monoisotopic Molecular Weight

366.204238692

IUPAC Name

(5S,6Z,8E,10E,12R,14Z)-5,12-dihydroxyicosa-6,8,10,14-tetraenedioic acid

Traditional Name

20-cooh-LTB4

CAS Registry Number

80434-82-8

SMILES

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

InChI Identifier

InChI=1S/C20H30O6/c21-17(11-6-2-1-3-9-15-19(23)24)12-7-4-5-8-13-18(22)14-10-16-20(25)26/h2,4-8,12-13,17-18,21-22H,1,3,9-11,14-16H2,(H,23,24)(H,25,26)/b5-4+,6-2-,12-7+,13-8-/t17-,18-/m1/s1

InChI Key

SXWGPVJGNOLNHT-VFLUTPEKSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acids and conjugates

Direct Parent

Long-chain fatty acids

Alternative Parents

Substituents

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

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

icosatetraenedioic acid (CHEBI:27562 )
Leukotrienes (C05950 )
Leukotrienes (LMFA03020016 )

Ontology

Status

Expected but not Quantified

Origin

Endogenous

Exogenous

Biofunction

Not Available

Application

Not Available

Cellular locations

Adiposome
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	3.17	ALOGPS
logP	2.81	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Acidic)	4.33	ChemAxon
pKa (Strongest Basic)	-1.3	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	115.06 Å²	ChemAxon
Rotatable Bond Count	15	ChemAxon
Refractivity	104.65 m³·mol⁻¹	ChemAxon
Polarizability	40.39 Å³	ChemAxon
Number of Rings	0	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	splash10-0005-2689000000-096c66447bfe6ad6733e	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positive	splash10-002p-5210976000-f9a166749a4b77249360	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	splash10-001j-0009000000-5550fddab03d6af2f102	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0f8j-0249000000-a2aa1fa4a5b39c1fd168	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0gw1-3493000000-1c97736464f35a64b096	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0009000000-e264ae86339bd5dedb96	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0v4j-0119000000-c7065844077ceffef493	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-9242000000-99ba9a3a04c75f28044a	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00kb-0009000000-a987ee79162f85ff16ce	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-052b-3039000000-233d80f7f111963e8f18	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-052f-9552000000-821cd0bc697d2333645f	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001j-0029000000-a8397c4233da39a13193	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-053s-1096000000-4ced9dcb2b61dd57a14d	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0570-9371000000-48100671499945ded827	View in MoNA