This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.

Identification

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Name
Leukotriene C4
Accession Number
DB08855
Type
Small Molecule
Groups
Experimental, Investigational
Description

The conjugation product of LEUKOTRIENE A4 and glutathione. It is the major arachidonic acid metabolite in macrophages and human mast cells as well as in antigen-sensitized lung tissue. It stimulates mucus secretion in the lung, and produces contractions of nonvascular and some vascular smooth muscle. (From Dictionary of Prostaglandins and Related Compounds, 1990)

Structure
Thumb
Synonyms
  • (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
  • L-γ-glutamyl-S-[(1R,2E,4E,6Z,9Z)-1-[(1S)-4-carboxy-1-hydroxybutyl]pentadeca-2,4,6,9-tetraen-1-yl]-L-cysteinylglycine
  • LTC (sub 4)
  • LTC4
Categories
UNII
2CU6TT9V48
CAS number
72025-60-6
Weight
Average: 625.774
Monoisotopic: 625.303300807
Chemical Formula
C30H47N3O9S
InChI Key
GWNVDXQDILPJIG-NXOLIXFESA-N
InChI
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
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
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

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UCysteinyl leukotriene receptor 1Not AvailableHumans
UCysteinyl leukotriene receptor 2Not AvailableHumans
UMultidrug resistance-associated protein 1Not AvailableHumans
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Not Available
Food Interactions
Not Available

References

General References
Not Available
External Links
Human Metabolome Database
HMDB0001198
KEGG Compound
C02166
ChemSpider
4444133
ChEBI
16978
ChEMBL
CHEMBL451509
HET
LTX
Wikipedia
Leukotriene_C4
PDB Entries
5b6f / 5h9n / 5kvl / 5uja

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.00254 mg/mLALOGPS
logP0.04ALOGPS
logP-0.015ChemAxon
logS-5.4ALOGPS
pKa (Strongest Acidic)1.8ChemAxon
pKa (Strongest Basic)9.31ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area216.35 Å2ChemAxon
Rotatable Bond Count25ChemAxon
Refractivity168.51 m3·mol-1ChemAxon
Polarizability68.38 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-QIT , negativeLC-MS/MSsplash10-00di-0000009000-9ba4d29fb234bf629c19
LC-MS/MS Spectrum - LC-ESI-QIT , negativeLC-MS/MSsplash10-00di-0000009000-c2e3b5fb18c749bec683
LC-MS/MS Spectrum - LC-ESI-QIT , negativeLC-MS/MSsplash10-00di-0000009000-764950659a3ede43e5fa
LC-MS/MS Spectrum - LC-ESI-QIT , negativeLC-MS/MSsplash10-00di-0000009000-84d0f40152dc35593991
LC-MS/MS Spectrum - LC-ESI-QIT , negativeLC-MS/MSsplash10-00di-0000009000-2b9de1e9017bddef56ff
LC-MS/MS Spectrum - LC-ESI-QIT , negativeLC-MS/MSsplash10-00di-0020019000-c37ade6bbbbb0db63082
LC-MS/MS Spectrum - LC-ESI-QIT , negativeLC-MS/MSsplash10-0c00-0290044000-556a3c7aef20c3fd1ba2
LC-MS/MS Spectrum - LC-ESI-QIT , negativeLC-MS/MSsplash10-0un9-0492001000-2801dff9e15f1a96421c
LC-MS/MS Spectrum - LC-ESI-QIT , negativeLC-MS/MSsplash10-01t9-0970000000-e6b8d4063abe84fe54f6

Taxonomy

Description
This compound 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
Gamma-glutamyl peptides / Leukotrienes / Hydroxyeicosatetraenoic acids / Glutamine and derivatives / N-acyl-alpha amino acids / Alpha amino acid amides / Cysteine and derivatives / L-alpha-amino acids / Tricarboxylic acids and derivatives / Thia fatty acids
show 13 more
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
show 33 more
Molecular Framework
Aliphatic acyclic compounds
External Descriptors
leukotriene (CHEBI:16978) / Leukotrienes (C02166) / Leukotrienes (LMFA03020003)

Targets

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Leukotriene receptor activity
Specific Function
Receptor for cysteinyl leukotrienes mediating bronchoconstriction of individuals with and without asthma. Stimulation by LTD4 results in the contraction and proliferation of smooth muscle, edema, e...
Gene Name
CYSLTR1
Uniprot ID
Q9Y271
Uniprot Name
Cysteinyl leukotriene receptor 1
Molecular Weight
38540.55 Da
References
  1. Lynch KR, O'Neill GP, Liu Q, Im DS, Sawyer N, Metters KM, Coulombe N, Abramovitz M, Figueroa DJ, Zeng Z, Connolly BM, Bai C, Austin CP, Chateauneuf A, Stocco R, Greig GM, Kargman S, Hooks SB, Hosfield E, Williams DL Jr, Ford-Hutchinson AW, Caskey CT, Evans JF: Characterization of the human cysteinyl leukotriene CysLT1 receptor. Nature. 1999 Jun 24;399(6738):789-93. [PubMed:10391245]
  2. Sarau HM, Ames RS, Chambers J, Ellis C, Elshourbagy N, Foley JJ, Schmidt DB, Muccitelli RM, Jenkins O, Murdock PR, Herrity NC, Halsey W, Sathe G, Muir AI, Nuthulaganti P, Dytko GM, Buckley PT, Wilson S, Bergsma DJ, Hay DW: Identification, molecular cloning, expression, and characterization of a cysteinyl leukotriene receptor. Mol Pharmacol. 1999 Sep;56(3):657-63. [PubMed:10462554]
  3. Bouchelouche K, Andersen L, Nordling J, Horn T, Bouchelouche P: The cysteinyl-leukotriene D4 induces cytosolic Ca2+ elevation and contraction of the human detrusor muscle. J Urol. 2003 Aug;170(2 Pt 1):638-44. [PubMed:12853847]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Leukotriene receptor activity
Specific Function
Receptor for cysteinyl leukotrienes. The response is mediated via a G-protein that activates a phosphatidylinositol-calcium second messenger system. Stimulation by BAY u9773, a partial agonist, ind...
Gene Name
CYSLTR2
Uniprot ID
Q9NS75
Uniprot Name
Cysteinyl leukotriene receptor 2
Molecular Weight
39634.815 Da
References
  1. Nothacker HP, Wang Z, Zhu Y, Reinscheid RK, Lin SH, Civelli O: Molecular cloning and characterization of a second human cysteinyl leukotriene receptor: discovery of a subtype selective agonist. Mol Pharmacol. 2000 Dec;58(6):1601-8. [PubMed:11093801]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Transporter activity
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, methotre...
Gene Name
ABCC1
Uniprot ID
P33527
Uniprot Name
Multidrug resistance-associated protein 1
Molecular Weight
171589.5 Da
References
  1. Karwatsky J, Leimanis M, Cai J, Gros P, Georges E: The leucotriene C4 binding sites in multidrug resistance protein 1 (ABCC1) include the first membrane multiple spanning domain. Biochemistry. 2005 Jan 11;44(1):340-51. [PubMed:15628876]

Transporters

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Sodium-independent organic anion transmembrane transporter activity
Specific Function
Mediates the Na(+)-independent uptake of organic anions such as pravastatin, taurocholate, methotrexate, dehydroepiandrosterone sulfate, 17-beta-glucuronosyl estradiol, estrone sulfate, prostagland...
Gene Name
SLCO1B1
Uniprot ID
Q9Y6L6
Uniprot Name
Solute carrier organic anion transporter family member 1B1
Molecular Weight
76447.99 Da
References
  1. Kullak-Ublick GA, Ismair MG, Stieger B, Landmann L, Huber R, Pizzagalli F, Fattinger K, Meier PJ, Hagenbuch B: Organic anion-transporting polypeptide B (OATP-B) and its functional comparison with three other OATPs of human liver. Gastroenterology. 2001 Feb;120(2):525-33. [PubMed:11159893]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Sodium-independent organic anion transmembrane transporter activity
Specific Function
Mediates the Na(+)-independent uptake of organic anions such as 17-beta-glucuronosyl estradiol, taurocholate, triiodothyronine (T3), leukotriene C4, dehydroepiandrosterone sulfate (DHEAS), methotre...
Gene Name
SLCO1B3
Uniprot ID
Q9NPD5
Uniprot Name
Solute carrier organic anion transporter family member 1B3
Molecular Weight
77402.175 Da
References
  1. Kullak-Ublick GA, Ismair MG, Stieger B, Landmann L, Huber R, Pizzagalli F, Fattinger K, Meier PJ, Hagenbuch B: Organic anion-transporting polypeptide B (OATP-B) and its functional comparison with three other OATPs of human liver. Gastroenterology. 2001 Feb;120(2):525-33. [PubMed:11159893]

Drug created on March 03, 2013 16:13 / Updated on December 02, 2019 08:30