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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:50 UTC
Update Date2022-03-07 02:51:43 UTC
HMDB IDHMDB0014725
Secondary Accession Numbers
  • HMDB14725
Metabolite Identification
Common NameCinalukast
DescriptionCinalukast belongs to the class of organic compounds known as anilides. These are organic heterocyclic compounds derived from oxoacids RkE(=O)l(OH)m (l not 0) by replacing an OH group by the NHPh group or derivative formed by ring substitution. Cinalukast is a drug which is used for protection against second- phase inflamation in exercise-induced bronchoconstriction and asthma. Based on a literature review very few articles have been published on Cinalukast.
Structure
Data?1582753213
Synonyms
ValueSource
3'-((e)-2-(4-Cyclobutyl-2-thiazolyl)vinyl)-2,2-diethylsuccinanilic acidChEBI
3'-((e)-2-(4-Cyclobutyl-2-thiazolyl)vinyl)-2,2-diethylsuccinanilateGenerator
4-(3-(2-(4-Cyclobutyl-2-thiazolyl)ethenyl)phenylamino)-2,2-diethyl-4-oxobutanoic acidHMDB
Chemical FormulaC23H28N2O3S
Average Molecular Weight412.545
Monoisotopic Molecular Weight412.182063462
IUPAC Name3-({3-[(E)-2-(4-cyclobutyl-1,3-thiazol-2-yl)ethenyl]phenyl}carbamoyl)-2,2-diethylpropanoic acid
Traditional Namecinalukast
CAS Registry Number128312-51-6
SMILES
CCC(CC)(CC(=O)NC1=CC=CC(\C=C\C2=NC(=CS2)C2CCC2)=C1)C(O)=O
InChI Identifier
InChI=1S/C23H28N2O3S/c1-3-23(4-2,22(27)28)14-20(26)24-18-10-5-7-16(13-18)11-12-21-25-19(15-29-21)17-8-6-9-17/h5,7,10-13,15,17H,3-4,6,8-9,14H2,1-2H3,(H,24,26)(H,27,28)/b12-11+
InChI KeyBZMKNPGKXJAIDV-VAWYXSNFSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as anilides. These are organic heterocyclic compounds derived from oxoacids RkE(=O)l(OH)m (l not 0) by replacing an OH group by the NHPh group or derivative formed by ring substitution.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassAnilides
Direct ParentAnilides
Alternative Parents
Substituents
  • Anilide
  • Styrene
  • N-arylamide
  • 2,4-disubstituted 1,3-thiazole
  • Fatty amide
  • Fatty acyl
  • Azole
  • Heteroaromatic compound
  • Thiazole
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Azacycle
  • Organoheterocyclic compound
  • Organic oxygen compound
  • Organic oxide
  • Organic nitrogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Carbonyl group
  • Organopnictogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.00087 g/LNot Available
LogP4Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.00087 g/LALOGPS
logP4.98ALOGPS
logP5.48ChemAxon
logS-5.7ALOGPS
pKa (Strongest Acidic)4.36ChemAxon
pKa (Strongest Basic)2.44ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area79.29 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity116.75 m³·mol⁻¹ChemAxon
Polarizability45.8 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+198.68430932474
DeepCCS[M-H]-196.32630932474
DeepCCS[M-2H]-230.14530932474
DeepCCS[M+Na]+205.37430932474
AllCCS[M+H]+200.632859911
AllCCS[M+H-H2O]+198.432859911
AllCCS[M+NH4]+202.632859911
AllCCS[M+Na]+203.132859911
AllCCS[M-H]-194.932859911
AllCCS[M+Na-2H]-195.532859911
AllCCS[M+HCOO]-196.432859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
CinalukastCCC(CC)(CC(=O)NC1=CC=CC(\C=C\C2=NC(=CS2)C2CCC2)=C1)C(O)=O5006.6Standard polar33892256
CinalukastCCC(CC)(CC(=O)NC1=CC=CC(\C=C\C2=NC(=CS2)C2CCC2)=C1)C(O)=O3400.5Standard non polar33892256
CinalukastCCC(CC)(CC(=O)NC1=CC=CC(\C=C\C2=NC(=CS2)C2CCC2)=C1)C(O)=O3701.5Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Cinalukast,1TMS,isomer #1CCC(CC)(CC(=O)NC1=CC=CC(/C=C/C2=NC(C3CCC3)=CS2)=C1)C(=O)O[Si](C)(C)C3619.9Semi standard non polar33892256
Cinalukast,1TMS,isomer #2CCC(CC)(CC(=O)N(C1=CC=CC(/C=C/C2=NC(C3CCC3)=CS2)=C1)[Si](C)(C)C)C(=O)O3550.2Semi standard non polar33892256
Cinalukast,2TMS,isomer #1CCC(CC)(CC(=O)N(C1=CC=CC(/C=C/C2=NC(C3CCC3)=CS2)=C1)[Si](C)(C)C)C(=O)O[Si](C)(C)C3421.7Semi standard non polar33892256
Cinalukast,2TMS,isomer #1CCC(CC)(CC(=O)N(C1=CC=CC(/C=C/C2=NC(C3CCC3)=CS2)=C1)[Si](C)(C)C)C(=O)O[Si](C)(C)C3417.8Standard non polar33892256
Cinalukast,2TMS,isomer #1CCC(CC)(CC(=O)N(C1=CC=CC(/C=C/C2=NC(C3CCC3)=CS2)=C1)[Si](C)(C)C)C(=O)O[Si](C)(C)C4086.3Standard polar33892256
Cinalukast,1TBDMS,isomer #1CCC(CC)(CC(=O)NC1=CC=CC(/C=C/C2=NC(C3CCC3)=CS2)=C1)C(=O)O[Si](C)(C)C(C)(C)C3835.4Semi standard non polar33892256
Cinalukast,1TBDMS,isomer #2CCC(CC)(CC(=O)N(C1=CC=CC(/C=C/C2=NC(C3CCC3)=CS2)=C1)[Si](C)(C)C(C)(C)C)C(=O)O3750.3Semi standard non polar33892256
Cinalukast,2TBDMS,isomer #1CCC(CC)(CC(=O)N(C1=CC=CC(/C=C/C2=NC(C3CCC3)=CS2)=C1)[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C3789.8Semi standard non polar33892256
Cinalukast,2TBDMS,isomer #1CCC(CC)(CC(=O)N(C1=CC=CC(/C=C/C2=NC(C3CCC3)=CS2)=C1)[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C3878.4Standard non polar33892256
Cinalukast,2TBDMS,isomer #1CCC(CC)(CC(=O)N(C1=CC=CC(/C=C/C2=NC(C3CCC3)=CS2)=C1)[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C4153.6Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Cinalukast GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a59-4379000000-738e6d7592628c151ba02017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Cinalukast GC-MS (1 TMS) - 70eV, Positivesplash10-074l-9305800000-d1299e5068cf6861be4b2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Cinalukast GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Cinalukast GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cinalukast 10V, Positive-QTOFsplash10-0bt9-0294400000-f92831fe0a108ec270fa2016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cinalukast 20V, Positive-QTOFsplash10-0a4i-0291000000-7d920d5c1e2519d3d0302016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cinalukast 40V, Positive-QTOFsplash10-00m0-9630000000-4394a5ce969ab4fe86a22016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cinalukast 10V, Negative-QTOFsplash10-03e9-0229500000-be5b09ebcb69df32c4ea2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cinalukast 20V, Negative-QTOFsplash10-0cdr-3879300000-8558f0369c4e4e20ecf12016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cinalukast 40V, Negative-QTOFsplash10-0w29-4960000000-c648dd857204eea481362016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cinalukast 10V, Positive-QTOFsplash10-08fr-2456900000-eb3b49687f6cb6233edc2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cinalukast 20V, Positive-QTOFsplash10-014j-5089000000-0cb9d2efa3e5036750e22021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cinalukast 40V, Positive-QTOFsplash10-0nni-4391000000-42671c23660bfea27a9b2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cinalukast 10V, Negative-QTOFsplash10-03di-0011900000-5acd86465f2a92838c862021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cinalukast 20V, Negative-QTOFsplash10-05nr-2169000000-cb03145d53ae6c7677ad2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cinalukast 40V, Negative-QTOFsplash10-0a4l-7792100000-9db94de0b6143268bd312021-10-11Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00587 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00587 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00587
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID4940804
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound6436135
PDB IDNot Available
ChEBI ID126598
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Involved in G-protein coupled receptor protein signaling pathway
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, eosinophil migration and damage to the mucus layer in the lung. This response is mediated via a G-protein that activates a phosphatidylinositol-calcium second messenger system. The rank order of affinities for the leukotrienes is LTD4 >> LTE4 = LTC4 >> LTB4
Gene Name:
CYSLTR1
Uniprot ID:
Q9Y271
Molecular weight:
38540.5
References
  1. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
  2. Adelroth E, Inman MD, Summers E, Pace D, Modi M, O'Byrne PM: Prolonged protection against exercise-induced bronchoconstriction by the leukotriene D4-receptor antagonist cinalukast. J Allergy Clin Immunol. 1997 Feb;99(2):210-5. [PubMed:9042047 ]
  3. Foller M, Mahmud H, Gu S, Wang K, Floride E, Kucherenko Y, Luik S, Laufer S, Lang F: Participation of leukotriene C(4) in the regulation of suicidal erythrocyte death. J Physiol Pharmacol. 2009 Sep;60(3):135-43. [PubMed:19826192 ]