Bovine Metabolome Database: Showing metabocard for Leukotriene C4 (BMDB0001198)

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 22:42:28 UTC

Update Date

2020-05-19 22:01:11 UTC

BMDB ID

BMDB0001198

Secondary Accession Numbers

BMDB01198

Metabolite Identification

Common Name

Leukotriene C4

Description

Leukotriene C4, also known as 5S,6R-LTC(sub 4) or LTC4, belongs to the class of organic compounds known as oligopeptides. These are organic compounds containing a sequence of between three and ten alpha-amino acids joined by peptide bonds. Thus, leukotriene C4 is considered to be an eicosanoid lipid molecule. Leukotriene C4 is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Within humans, leukotriene C4 participates in a number of enzymatic reactions. In particular, leukotriene C4 can be biosynthesized from leukotriene A4 and glutathione; which is catalyzed by the enzyme leukotriene C4 synthase. In addition, leukotriene C4 can be converted into leukotriene D4 and L-glutamic acid through its interaction with the enzyme Gamma-glutamyltranspeptidase 1. In humans, leukotriene C4 is involved in mefenamic acid action pathway. Outside of the human body, Leukotriene C4 has been detected, but not quantified in, several different foods, such as romaine lettuces, mung beans, annual wild rices, dandelions, and java plums. This could make leukotriene C4 a potential biomarker for the consumption of these foods. Leukotriene C4, with regard to humans, has been found to be associated with several diseases such as leukotriene c4-synthesis deficiency, aseptic meningitis, hydrocephalus, and aids; leukotriene C4 has also been linked to the inborn metabolic disorder glutathione synthetase deficiency. A leukotriene that is (5S,7E,9E,11Z,14Z)-5-hydroxyicosa-7,9,11,14-tetraenoic acid in which a glutathionyl group is attached at position 6 via a sulfide linkage.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(R-(R,s-(e,e,Z,Z)))-N-(S-(1-(4-carboxy-1-hydroxybutyl)-2,4,6,9-pentadecatetraenyl)-N-L-gamma-glutamyl-L-cysteinyl)glycine	ChEBI
5S,6R-LTC(Sub 4)	ChEBI
5S-Hydroxy,6R-(S-glutathionyl),7E,9E,11Z,14Z-eicosatetraenoic acid	ChEBI
LTC (Sub 4)	ChEBI
LTC4	ChEBI
(R-(R,s-(e,e,Z,Z)))-N-(S-(1-(4-carboxy-1-hydroxybutyl)-2,4,6,9-pentadecatetraenyl)-N-L-g-glutamyl-L-cysteinyl)glycine	Generator
(R-(R,s-(e,e,Z,Z)))-N-(S-(1-(4-carboxy-1-hydroxybutyl)-2,4,6,9-pentadecatetraenyl)-N-L-γ-glutamyl-L-cysteinyl)glycine	Generator
5S-Hydroxy,6R-(S-glutathionyl),7E,9E,11Z,14Z-eicosatetraenoate	Generator
Leukotriene C-1	HMDB
Leukotriene C-4	HMDB
Leukotrienes C	HMDB
Leukotriene C	HMDB
Leukotriene C 1	HMDB
Leukotriene C 4	HMDB
Leukotriene C1	HMDB
(R-(R,s-(e,e,Z,Z)))-N-(S-(1-(4-carboxy-1-hydroxybutyl)-2,4,6,9-pentadecatetraenyl)-N-L-gamma-glutamyl-L-cysteinyl)-glycine	HMDB
5S,6R-LTC	HMDB
L-gamma-Glutamyl-S-[(1R,2E,4E,6Z,9Z)-1-[(1S)-4-carboxy-1-hydroxybutyl]-2,4,6,9-pentadecatetraenyl]-L-cysteinyl-glycine	HMDB
Leucotriene C4	HMDB
LTC	HMDB
[R-[R,s-(e,e,Z,Z)]]-N-[S-[1-(4-carboxy-1-hydroxybutyl)-2,4,6,9-pentadecatetraenyl]-N-L-gamma-glutamyl-L-cysteinyl]-glycine 5S,6R-LTC4	HMDB
5S,6R-LTC4	HMDB
Leukotriene C4	HMDB

Chemical Formula

C₃₀H₄₇N₃O₉S

Average Molecular Weight

625.774

Monoisotopic Molecular Weight

625.303300807

IUPAC Name

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

Traditional Name

leukotriene C4

CAS Registry Number

72025-60-6

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)NCC(O)=O)[C@@H](O)CCCC(O)=O

InChI Identifier

InChI=1S/C30H47N3O9S/c1-2-3-4-5-6-7-8-9-10-11-12-13-16-25(24(34)15-14-17-27(36)37)43-21-23(29(40)32-20-28(38)39)33-26(35)19-18-22(31)30(41)42/h6-7,9-13,16,22-25,34H,2-5,8,14-15,17-21,31H2,1H3,(H,32,40)(H,33,35)(H,36,37)(H,38,39)(H,41,42)/b7-6-,10-9-,12-11+,16-13+/t22-,23-,24-,25+/m0/s1

InChI Key

GWNVDXQDILPJIG-NXOLIXFESA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as oligopeptides. These are organic compounds containing a sequence of between three and ten alpha-amino acids joined by peptide bonds.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Oligopeptides

Alternative Parents

Substituents

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

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

leukotriene (CHEBI:16978 )
Leukotrienes (C02166 )
Leukotrienes (LMFA03020003 )

Ontology

Status

Expected but not Quantified

Origin

Endogenous

Biofunction

Not Available

Application

Not Available

Cellular locations

Endoplasmic reticulum

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	0.04	ALOGPS
logP	-0.015	ChemAxon
logS	-5.4	ALOGPS
pKa (Strongest Acidic)	1.8	ChemAxon
pKa (Strongest Basic)	9.31	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	216.35 Å²	ChemAxon
Rotatable Bond Count	25	ChemAxon
Refractivity	168.51 m³·mol⁻¹	ChemAxon
Polarizability	68.38 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	splash10-05o0-3202091000-c6dee8507ab8b61b0c02	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-0g5c-6203049000-51753829f5101ccfd684	View in MoNA
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_1_7) - 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_2_17) - 70eV, Positive	Not Available	View in JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QIT , negative	splash10-00di-0000009000-9ba4d29fb234bf629c19	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QIT , negative	splash10-00di-0000009000-c2e3b5fb18c749bec683	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QIT , negative	splash10-00di-0000009000-764950659a3ede43e5fa	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QIT , negative	splash10-00di-0000009000-84d0f40152dc35593991	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QIT , negative	splash10-00di-0000009000-2b9de1e9017bddef56ff	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QIT , negative	splash10-00di-0020019000-c37ade6bbbbb0db63082	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QIT , negative	splash10-0c00-0290044000-556a3c7aef20c3fd1ba2	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QIT , negative	splash10-0un9-0492001000-2801dff9e15f1a96421c	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QIT , negative	splash10-01t9-0970000000-e6b8d4063abe84fe54f6	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0c34-2010394000-b2537b2e21446a86fab1	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00di-9303360000-546ae5580086593ee435	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00di-9013010000-43aff9255ff94b18ed35	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0kn9-0127079000-3855e84af2520307dddf	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0zgr-0139010000-fdb78d5f775d532f53ec	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0f6y-2912000000-a86e557888d76eea9df8	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-0010009000-78d18a02a7849f6bf4ae	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00di-1951014000-2f6a645de70656f26d29	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0007-6900010000-a4f76d24eb6f5ec03a33	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0570-1405119000-3fe7d1ddf1fa60edcdb7	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00kr-1902000000-cf43af95f58742e02019	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-05o0-2900000000-92e9d6fced329468ccfd	View in MoNA
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer

Biological Properties

Cellular Locations

Endoplasmic reticulum

Biospecimen Locations

Epidermis
Eye Lens
Intestine
Leukocyte
Platelet
Smooth Muscle

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
Eye Lens	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Intestine	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
Smooth Muscle	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details

Abnormal Concentrations

Not Available

External Links

HMDB ID

HMDB0001198

DrugBank ID

DB08855

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB030979

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

C02166

BioCyc ID

LEUKOTRIENE-C4

BiGG ID

Not Available

Wikipedia Link

Leukotriene_C4

METLIN ID

Not Available

PubChem Compound

5280493

PDB ID

Not Available

ChEBI ID

16978

References

Synthesis Reference

Rokach, Joshua; Young, Robert N.; Kakushima, Masatoshi; Lau, Cheuk-Kun; Seguin, Rick; Frenette, Richard; Guindon, Yvan. Synthesis of leukotrienes. New synthesis of natural leukotriene A4. Tetrahedron Letters (1981), 22(11), 979-82.

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Enzymes

Enzyme Details

1. 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

Enzyme Details

2. Multidrug resistance-associated protein 1

General function:: Defense mechanisms
Specific function:: Mediates export of organic anions and drugs from the cytoplasm. Mediates ATP-dependent transport of glutathione and glutathione conjugates, leukotriene C4, estradiol-17-beta-o-glucuronide, methotrexate, antiviral drugs and other xenobiotics. Confers resistance to anticancer drugs by decreasing accumulation of drug in cells, and by mediating ATP- and GSH-dependent drug export (PubMed:12067707). Hydrolyzes ATP with low efficiency. Catalyzes the export of sphingosine 1-phosphate from mast cells independently of their degranulation (By similarity). Participates in inflammatory response by allowing export of leukotriene C4 from leukotriene C4-synthezing cells (By similarity).
Gene Name:: ABCC1
Uniprot ID:: Q8HXQ5
Molecular weight:: 171666.0

Showing metabocard for Leukotriene C4 (BMDB0001198)

Structure for BMDB0001198 (Leukotriene C4)

Enzymes

Reactions