Bovine Metabolome Database: Showing metabocard for Leukotriene F4 (BMDB0006465)

Identification Taxonomy Physical properties Pathways Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-09-30 23:22:14 UTC

Update Date

2020-04-22 15:17:30 UTC

BMDB ID

BMDB0006465

Secondary Accession Numbers

BMDB06465

Metabolite Identification

Common Name

Leukotriene F4

Description

Leukotriene F4, also known as LTF4, 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 F4 is considered to be an eicosanoid. Based on a literature review a significant number of articles have been published on Leukotriene F4.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
5(S)-Hydroxy-6(R)-S-gamma-glutamylcysteine-7,9-trans-11,14-cis-eicosatetraenoic acid	ChEBI
L-gamma-Glutamyl-S-{(1R,2E,4E,6Z,9Z)-1-[(1S)-4-carboxy-1-hydroxybutyl]pentadeca-2,4,6,9-tetraen-1-yl}-L-cysteine	ChEBI
Leukotriene F-4	ChEBI
LTF4	ChEBI
5(S)-Hydroxy-6(R)-S-g-glutamylcysteine-7,9-trans-11,14-cis-eicosatetraenoate	Generator
5(S)-Hydroxy-6(R)-S-g-glutamylcysteine-7,9-trans-11,14-cis-eicosatetraenoic acid	Generator
5(S)-Hydroxy-6(R)-S-gamma-glutamylcysteine-7,9-trans-11,14-cis-eicosatetraenoate	Generator
5(S)-Hydroxy-6(R)-S-γ-glutamylcysteine-7,9-trans-11,14-cis-eicosatetraenoate	Generator
5(S)-Hydroxy-6(R)-S-γ-glutamylcysteine-7,9-trans-11,14-cis-eicosatetraenoic acid	Generator
L-g-Glutamyl-S-{(1R,2E,4E,6Z,9Z)-1-[(1S)-4-carboxy-1-hydroxybutyl]pentadeca-2,4,6,9-tetraen-1-yl}-L-cysteine	Generator
L-Γ-glutamyl-S-{(1R,2E,4E,6Z,9Z)-1-[(1S)-4-carboxy-1-hydroxybutyl]pentadeca-2,4,6,9-tetraen-1-yl}-L-cysteine	Generator
5S-Hydroxy-6R-(S-glutamylcysteinyl)-7E,9E,11Z,14Z-eicosatetraenoate	HMDB
5S-Hydroxy-6R-(S-glutamylcysteinyl)-7E,9E,11Z,14Z-eicosatetraenoic acid	HMDB

Chemical Formula

C₂₈H₄₄N₂O₈S

Average Molecular Weight

568.723

Monoisotopic Molecular Weight

568.281837084

IUPAC Name

(5S,6R,7E,9E,11Z,14Z)-6-{[(2R)-2-[(4S)-4-amino-4-carboxybutanamido]-2-carboxyethyl]sulfanyl}-5-hydroxyicosa-7,9,11,14-tetraenoic acid

Traditional Name

leukotriene F4

CAS Registry Number

83851-42-7

SMILES

CCCCC\C=C/C\C=C/C=C/C=C/[C@@H](SC[C@H](NC(=O)CC[C@H](N)C(O)=O)C(O)=O)[C@@H](O)CCCC(O)=O

InChI Identifier

InChI=1S/C28H44N2O8S/c1-2-3-4-5-6-7-8-9-10-11-12-13-16-24(23(31)15-14-17-26(33)34)39-20-22(28(37)38)30-25(32)19-18-21(29)27(35)36/h6-7,9-13,16,21-24,31H,2-5,8,14-15,17-20,29H2,1H3,(H,30,32)(H,33,34)(H,35,36)(H,37,38)/b7-6-,10-9-,12-11+,16-13+/t21-,22-,23-,24+/m0/s1

InChI Key

PYSODLWHFWCFLV-VJBFNVCUSA-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
Alpha-dipeptide
Gamma-glutamyl alpha-amino acid
Glutamine or derivatives
N-acyl-l-alpha-amino acid
N-acyl-alpha-amino acid
N-acyl-alpha amino acid or derivatives
Cysteine or derivatives
Alpha-amino acid
Alpha-amino acid or derivatives
L-alpha-amino acid
Tricarboxylic acid or derivatives
Hydroxy fatty acid
Thia fatty acid
Fatty amide
N-acyl-amine
Secondary alcohol
Secondary carboxylic acid amide
Amino acid or derivatives
Carboxamide group
Amino acid
Thioether
Sulfenyl compound
Dialkylthioether
Carboxylic acid derivative
Carboxylic acid
Primary amine
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Alcohol
Primary aliphatic amine
Organonitrogen compound
Carbonyl group
Organooxygen compound
Amine
Organic oxygen compound
Organic nitrogen compound
Organosulfur compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

leukotriene (CHEBI:27491 )
Leukotrienes (C06462 )
Leukotrienes (LMFA03020009 )

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	0.69	ALOGPS
logP	1.14	ChemAxon
logS	-5.3	ALOGPS
pKa (Strongest Acidic)	1.77	ChemAxon
pKa (Strongest Basic)	9.31	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	187.25 Å²	ChemAxon
Rotatable Bond Count	23	ChemAxon
Refractivity	155.71 m³·mol⁻¹	ChemAxon
Polarizability	62.92 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	splash10-0g4l-6413390000-dee39a27081fc5a88fc9	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-00xv-9314083000-d5186b17ce38316aef6a	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS ("Leukotriene F4,1TMS,#1" TMS) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_4) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_5) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_6) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_4) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_5) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_6) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_7) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_8) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_9) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_10) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_11) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_12) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_13) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_14) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_15) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_16) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_3_1) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0zn9-0000190000-de2d2f5e2583512ed1e3	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0079-2805890000-f9aea2d590c4c6a8bb95	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0pi9-8749220000-9d280ac5a92d5f4e475e	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00l2-0023090000-23b4133bee512f6ae0d4	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0f8a-0169230000-b386e734e0822f0f7483	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-000i-6942000000-7df258f20e5665566211	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0100090000-aabfb28ab58bc9871e3a	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0frt-2957150000-6c0eadffc826c6e16ea3	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-003f-9400000000-761921bb2745202a2fe9	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0uxr-0329030000-f55fa0bd92c071ec6eb7	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0gbl-2914000000-00e11cbf64a58818b84a	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-05o0-2900000000-200b6f45dc516fbf832b	View in MoNA

Biological Properties

Cellular Locations

Cell membrane
Cytoplasm
Membrane

Biospecimen Locations

Not Available

Pathways

Not Available

Name	SMPDB/Pathwhiz	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

External Links

HMDB ID

HMDB0006465

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB023925

KNApSAcK ID

Not Available

Chemspider ID

4444440

KEGG Compound ID

C06462

BioCyc ID

Not Available

BiGG ID

2705818

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5280938

PDB ID

Not Available

ChEBI ID

27491

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Showing metabocard for Leukotriene F4 (BMDB0006465)

Structure for BMDB0006465 (Leukotriene F4)