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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2022-09-09 20:57:23 UTC
Update Date2022-09-22 18:34:53 UTC
HMDB IDHMDB0341402
Secondary Accession NumbersNone
Metabolite Identification
Common NameTranilast
DescriptionTranilast (trans-) 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. Based on a literature review a significant number of articles have been published on Tranilast (trans-).
Structure
Thumb
SynonymsNot Available
Chemical FormulaC18H17NO5
Average Molecular Weight327.336
Monoisotopic Molecular Weight327.110672651
IUPAC Name2-[3-(3,4-dimethoxyphenyl)prop-2-enamido]benzoic acid
Traditional Nametranilast
CAS Registry NumberNot Available
SMILES
COC1=C(OC)C=C(C=CC(=O)NC2=CC=CC=C2C(O)=O)C=C1
InChI Identifier
InChI=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)
InChI KeyNZHGWWWHIYHZNX-UHFFFAOYSA-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 DescriptorsNot Available
Ontology
Physiological effectNot Available
DispositionNot Available
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
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
Polarizability34.26 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+174.56530932474
DeepCCS[M-H]-172.20730932474
DeepCCS[M-2H]-206.10930932474
DeepCCS[M+Na]+181.90930932474
AllCCS[M+H]+177.632859911
AllCCS[M+H-H2O]+174.432859911
AllCCS[M+NH4]+180.732859911
AllCCS[M+Na]+181.632859911
AllCCS[M-H]-178.932859911
AllCCS[M+Na-2H]-178.632859911
AllCCS[M+HCOO]-178.532859911

Predicted Kovats Retention Indices

Not Available
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Benzoic acid, 2-[[3-(3,4-dimethoxyphenyl)-1-oxo-2-propenyl]amino]- GC-MS (Non-derivatized) - 70eV, Positivesplash10-03di-0956000000-76667488af9ce4be02872021-09-23Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Benzoic acid, 2-[[3-(3,4-dimethoxyphenyl)-1-oxo-2-propenyl]amino]- GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Benzoic acid, 2-[[3-(3,4-dimethoxyphenyl)-1-oxo-2-propenyl]amino]- GC-MS (TMS_1_1) - 70eV, PositiveNot Available2021-11-03Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Benzoic acid, 2-[[3-(3,4-dimethoxyphenyl)-1-oxo-2-propenyl]amino]- GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-11-03Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Benzoic acid, 2-[[3-(3,4-dimethoxyphenyl)-1-oxo-2-propenyl]amino]- GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-11-03Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Benzoic acid, 2-[[3-(3,4-dimethoxyphenyl)-1-oxo-2-propenyl]amino]- GC-MS (TBDMS_1_2) - 70eV, PositiveNot Available2021-11-03Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tranilast 10V, Positive-QTOFsplash10-0006-0900000000-b9cd47e83309e8c31f5f2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tranilast 20V, Positive-QTOFsplash10-01ox-0900000000-bd19728246069b7a10dd2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tranilast 40V, Positive-QTOFsplash10-01x0-0920000000-34079cc2ac90e1a5628f2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tranilast 10V, Negative-QTOFsplash10-004i-0239000000-ab769a1db4100b7b83db2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tranilast 20V, Negative-QTOFsplash10-0uxr-0290000000-fb85428e5ad08c98a6d92021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tranilast 40V, Negative-QTOFsplash10-0gbd-1590000000-be486d414eb47dc06ded2021-10-12Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedCancer patients undergoing total body irradiation details
UrineDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedCancer patients undergoing total body irradiation details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID5326
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5527
PDB IDNot Available
ChEBI ID92320
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 References
  1. Simon-Manso Y, Marupaka R, Yan X, Liang Y, Telu KH, Mirokhin Y, Stein SE: Mass Spectrometry Fingerprints of Small-Molecule Metabolites in Biofluids: Building a Spectral Library of Recurrent Spectra for Urine Analysis. Anal Chem. 2019 Sep 17;91(18):12021-12029. doi: 10.1021/acs.analchem.9b02977. Epub 2019 Aug 30. [PubMed:31424920 ]