Showing Compound leukotriene-C4 (FDB030979)

Record Information

Version

1.0

Creation date

2015-05-07 20:42:12 UTC

Update date

2019-11-26 03:22:00 UTC

Primary ID

FDB030979

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

leukotriene-C4

Description

Leukotriene c4, also known as ltc4 or 5s,6r-ltc(sub 4), is a member of the class of compounds known as oligopeptides. Oligopeptides 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 practically insoluble (in water) and a moderately acidic compound (based on its pKa). Leukotriene c4 can be synthesized from icosa-7,9,11,14-tetraenoic acid. Leukotriene c4 is also a parent compound for other transformation products, including but not limited to, leukotriene C4 methyl ester, 11,12-dihydro-(12R)-hydroxyleukotriene C4, and 11,12-dihydro-12-oxoleukotriene C4. Leukotriene c4 can be found in a number of food items such as gram bean, maitake, caraway, and burbot, which makes leukotriene c4 a potential biomarker for the consumption of these food products. Leukotriene c4 can be found primarily in blood and cerebrospinal fluid (CSF), as well as throughout most human tissues. In humans, leukotriene c4 is involved in several metabolic pathways, some of which include trisalicylate-choline action pathway, antipyrine action pathway, nepafenac action pathway, and fenoprofen action pathway. Leukotriene c4 is also involved in a couple of metabolic disorders, which include leukotriene C4 synthesis deficiency and tiaprofenic acid action pathway. Moreover, leukotriene c4 is found to be associated with eczema. Leukotriene C4 (LTC4) is a leukotriene. LTC4 has been extensively studied in the context of allergy and asthma. In cells of myeloid origin such as mast cells, its biosynthesis is orchestrated by translocation to the nuclear envelope along with co-localization of cytosolic phospholipase A2 (cPLA2), Arachidonate 5-lipoxygenase (5-LO), 5-lipoxygenase-activating protein (FLAP) and LTC4 synthase (LTC4S), which couples glutathione to an LTA4 intermediate.The MRP1 transporter then secretes cytosolic LTC4 and cell surface proteases further metabolize it by sequential cleavage of the γ-glutamyl and glycine residues off its glutathione segment, generating the more stable products LTD4 and LTE4. All three leukotrienes then bind at different affinities to two G-protein coupled receptors: CYSLTR1 and CYSLTR2, triggering pulmonary vasoconstriction and bronchoconstriction .

CAS Number

72025-60-6

Structure

MOL SDF PDB SMILES InChI

Synonyms

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Synonym	Source
(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-gamma-glutamyl-L-cysteinyl)-glycine	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	ChEBI
(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,6R-LTC	HMDB
5S,6R-LTC(Sub 4)	ChEBI
5S,6R-LTC4	HMDB
5S-Hydroxy,6R-(S-glutathionyl),7E,9E,11Z,14Z-eicosatetraenoate	Generator
5S-Hydroxy,6R-(S-glutathionyl),7E,9E,11Z,14Z-eicosatetraenoic acid	ChEBI
[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

Showing 1 to 10 of 23 entries

Predicted Properties

Property	Value	Source
Water Solubility	0.0025 g/L	ALOGPS
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	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C30H47N3O9S

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

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

Isomeric 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

Average Molecular Weight

625.774

Monoisotopic Molecular Weight

625.303300807

Classification

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

Physiological effect

Health effect:

Health condition:

Eczema

Disposition

Source:

Endogenous

Biological location:

Tissue and substructures:

Smooth muscle

Organ and components:

Biofluid and excreta:

Cell and elements:

Extracellular

Element:

Platelet

Cell:

White blood cell

Subcellular:

Endoplasmic reticulum

Role

Industrial application:

Pharmaceutical industry:

Pharmaceutical

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

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Property	Value	Reference
Boiling Point	Not Available
Charge	Not Available
Density	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Experimental Water Solubility	Not Available
Isoelectric point	Not Available
Mass Composition	Not Available
Melting Point	Not Available
Optical Rotation	Not Available

Showing 1 to 10 of 14 entries

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	leukotriene-C4, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-05o0-3202091000-c6dee8507ab8b61b0c02	Spectrum
Predicted GC-MS	leukotriene-C4, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0g5c-6203049000-51753829f5101ccfd684	Spectrum
Predicted GC-MS	leukotriene-C4, TMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	leukotriene-C4, TMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	leukotriene-C4, TMS_1_4, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	leukotriene-C4, TMS_1_5, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	leukotriene-C4, TMS_1_6, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	leukotriene-C4, TMS_1_7, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	leukotriene-C4, TMS_2_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	leukotriene-C4, TMS_2_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	leukotriene-C4, TMS_2_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	leukotriene-C4, TMS_2_4, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	leukotriene-C4, TMS_2_5, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	leukotriene-C4, TMS_2_6, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	leukotriene-C4, TMS_2_7, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	leukotriene-C4, TMS_2_8, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	leukotriene-C4, TMS_2_9, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	leukotriene-C4, TMS_2_10, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	leukotriene-C4, TMS_2_11, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	leukotriene-C4, TMS_2_12, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	leukotriene-C4, TMS_2_13, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	leukotriene-C4, TMS_2_14, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	leukotriene-C4, TMS_2_15, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	leukotriene-C4, TMS_2_16, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	leukotriene-C4, TMS_2_17, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - LC-ESI-QIT , negative	splash10-00di-0000009000-9ba4d29fb234bf629c19	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QIT , negative	splash10-00di-0000009000-c2e3b5fb18c749bec683	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QIT , negative	splash10-00di-0000009000-764950659a3ede43e5fa	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QIT , negative	splash10-00di-0000009000-84d0f40152dc35593991	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QIT , negative	splash10-00di-0000009000-2b9de1e9017bddef56ff	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QIT , negative	splash10-00di-0020019000-c37ade6bbbbb0db63082	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QIT , negative	splash10-0c00-0290044000-556a3c7aef20c3fd1ba2	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QIT , negative	splash10-0un9-0492001000-2801dff9e15f1a96421c	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QIT , negative	splash10-01t9-0970000000-e6b8d4063abe84fe54f6	2017-09-14	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0c34-2010394000-b2537b2e21446a86fab1	2017-07-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00di-9303360000-546ae5580086593ee435	2017-07-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00di-9013010000-43aff9255ff94b18ed35	2017-07-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0kn9-0127079000-3855e84af2520307dddf	2017-07-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0zgr-0139010000-fdb78d5f775d532f53ec	2017-07-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0f6y-2912000000-a86e557888d76eea9df8	2017-07-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-0010009000-78d18a02a7849f6bf4ae	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00di-1951014000-2f6a645de70656f26d29	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0007-6900010000-a4f76d24eb6f5ec03a33	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0570-1405119000-3fe7d1ddf1fa60edcdb7	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00kr-1902000000-cf43af95f58742e02019	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-05o0-2900000000-92e9d6fced329468ccfd	2021-09-22	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

Not Available

ChEMBL ID

Not Available

KEGG Compound ID

Not Available

Pubchem Compound ID

Not Available

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

Not Available

CRC / DFC (Dictionary of Food Compounds) ID

Not Available

EAFUS ID

Not Available

Dr. Duke ID

Not Available

BIGG ID

Not Available

KNApSAcK ID

Not Available

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

Not Available

Wikipedia ID

Not Available

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

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Food	Content Range	Average	Reference

Processing...

Biological Effects and Interactions

Health Effects / Bioactivities

Not Available

Enzymes

Not Available

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Not Available

Files

MSDS

Not Available

References

Synthesis Reference

Not Available

General Reference

Not Available

Content Reference

Showing Compound leukotriene-C4 (FDB030979)

Structure for FDB030979 (leukotriene-C4)