Tranilast (CHEM016918)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-22 03:47:32 UTC
Update Date2016-11-09 01:15:29 UTC
Accession NumberCHEM016918
Identification
Common NameTranilast
ClassSmall Molecule
DescriptionAn amidobenzoic acid that is anthranilic acid in which one of the anilino hydrogens is replaced by a 3,4-dimethoxycinnamoyl group.
Contaminant Sources
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
MK 341ChEBI
MK-341ChEBI
N-(3,4-Dimethoxycinnamoyl)anthranilic acidChEBI
RizabenChEBI
TranilastumChEBI
N-(3,4-Dimethoxycinnamoyl)anthranilateGenerator
Tranilast hydrateMeSH
N-(3',4'-Dimethoxycinnamoyl)anthranilic acidMeSH
Tranilast sodium saltMeSH
Chemical FormulaC18H17NO5
Average Molecular Mass327.331 g/mol
Monoisotopic Mass327.111 g/mol
CAS Registry Number53902-12-8
IUPAC Name2-[(2E)-3-(3,4-dimethoxyphenyl)prop-2-enamido]benzoic acid
Traditional Nametranilast
SMILESCOC1=CC=C(\C=C\C(=O)NC2=CC=CC=C2C(O)=O)C=C1OC
InChI IdentifierInChI=1S/C18H17NO5/c1-23-15-9-7-12(11-16(15)24-2)8-10-17(20)19-14-6-4-3-5-13(14)18(21)22/h3-11H,1-2H3,(H,19,20)(H,21,22)/b10-8+
InChI KeyNZHGWWWHIYHZNX-CSKARUKUSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as n-cinnamoylanthranilic acids. These are aromatic compounds containing a cinnamic acid conjugated to an anthranilic acid.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassCinnamic acids and derivatives
Sub ClassCinnamic acid amides
Direct ParentN-cinnamoylanthranilic acids
Alternative Parents
Substituents
  • N-cinnamoylanthranilic acid
  • Acylaminobenzoic acid or derivatives
  • O-dimethoxybenzene
  • Dimethoxybenzene
  • Benzoic acid or derivatives
  • Benzoic acid
  • Anilide
  • Phenoxy compound
  • Anisole
  • Phenol ether
  • Methoxybenzene
  • Benzoyl
  • Styrene
  • N-arylamide
  • Alkyl aryl ether
  • Monocyclic benzene moiety
  • Benzenoid
  • Vinylogous amide
  • Secondary carboxylic acid amide
  • Carboxamide group
  • Monocarboxylic acid or derivatives
  • Ether
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Carbonyl group
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0084 g/LALOGPS
logP2.89ALOGPS
logP3.56ChemAxon
logS-4.6ALOGPS
pKa (Strongest Acidic)3.55ChemAxon
pKa (Strongest Basic)-2ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area84.86 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity91.52 m³·mol⁻¹ChemAxon
Polarizability34.2 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-0006-1900000000-7541d25405a74d897cf6Spectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0006-1900000000-7541d25405a74d897cf6Spectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0006-2900000000-d54b9ceefe589f6ddc0bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-002r-0927000000-bf89e823c7cdd47a9a3dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-1911000000-5c1cf930a4fef308588dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0f7c-6900000000-4e912304070f09917a2dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0059-0298000000-ffa3ee332f7a1ed1ac0eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-015c-1391000000-8a5fb678eadbf6828badSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00kf-5930000000-30a98f56ec8a0cc28dc3Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDB07615
HMDB IDNot Available
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkTranilast
Chemspider IDNot Available
ChEBI ID77572
PubChem Compound ID5282230
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=22753703
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=23121382
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=23273396
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=23363021
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=23679559
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=23694807
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=23715805
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=23821545
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=23977380
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=24055688
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=24092987
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=24143895
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=24157455
14. https://www.ncbi.nlm.nih.gov/pubmed/?term=24374452
15. https://www.ncbi.nlm.nih.gov/pubmed/?term=24377619
16. https://www.ncbi.nlm.nih.gov/pubmed/?term=24384948
17. https://www.ncbi.nlm.nih.gov/pubmed/?term=24389486
18. https://www.ncbi.nlm.nih.gov/pubmed/?term=24389817
19. https://www.ncbi.nlm.nih.gov/pubmed/?term=24420060
20. https://www.ncbi.nlm.nih.gov/pubmed/?term=24448965
21. https://www.ncbi.nlm.nih.gov/pubmed/?term=24475260
22. https://www.ncbi.nlm.nih.gov/pubmed/?term=24476069