3-Carboxy-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-1-propanoic acid (CHEM028843)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 00:44:45 UTC
Update Date2016-11-09 01:18:46 UTC
Accession NumberCHEM028843
Identification
Common Name3-Carboxy-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-1-propanoic acid
ClassSmall Molecule
Description3-Carboxy-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-1-propanoic acid is found in alcoholic beverages. 3-Carboxy-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-1-propanoic acid is present in soy and worcester sauces, yeast extract and wine as the (3S)-diastereoisomers. 3-Carboxy-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-1-propanoic acid is formed by Pictet-Spengler condensation of tryptophan with 4-oxobutanoic acid to give predominantly the cis-isomer
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
3-Carboxy-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-1-propanoateGenerator
1-(2-Carboxyethyl)-1,2,3,4-tetrahydro-b-carboline-3-carboxylic acidHMDB
1-(2-Carboxyethyl)-1H,2H,3H,4H,9H-pyrido[3,4-b]indole-3-carboxylateGenerator
Chemical FormulaC15H16N2O4
Average Molecular Mass288.299 g/mol
Monoisotopic Mass288.111 g/mol
CAS Registry NumberNot Available
IUPAC Name1-(2-carboxyethyl)-1H,2H,3H,4H,9H-pyrido[3,4-b]indole-3-carboxylic acid
Traditional Name1-(2-carboxyethyl)-1H,2H,3H,4H,9H-pyrido[3,4-b]indole-3-carboxylic acid
SMILESOC(=O)CCC1NC(CC2=C1NC1=CC=CC=C21)C(O)=O
InChI IdentifierInChI=1S/C15H16N2O4/c18-13(19)6-5-11-14-9(7-12(16-11)15(20)21)8-3-1-2-4-10(8)17-14/h1-4,11-12,16-17H,5-7H2,(H,18,19)(H,20,21)
InChI KeyPPKGNUKJFFAWHY-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as harmala alkaloids. Harmala alkaloids are compounds with a structure based on harmaline, harmine, harmalol, harman or a derivative of those parents. These parents are beta-carbolines, consisting of a pyrimidine fused to the pyrrole moiety of an indole to form a pyrido[3,4-b]indole.
KingdomOrganic compounds
Super ClassAlkaloids and derivatives
ClassHarmala alkaloids
Sub ClassNot Available
Direct ParentHarmala alkaloids
Alternative Parents
Substituents
  • Harman
  • Beta-carboline
  • Pyridoindole
  • Alpha-amino acid
  • Alpha-amino acid or derivatives
  • 3-alkylindole
  • Indole
  • Indole or derivatives
  • Aralkylamine
  • Dicarboxylic acid or derivatives
  • Benzenoid
  • Heteroaromatic compound
  • Pyrrole
  • Amino acid or derivatives
  • Amino acid
  • Carboxylic acid derivative
  • Carboxylic acid
  • Secondary aliphatic amine
  • Azacycle
  • Organoheterocyclic compound
  • Secondary amine
  • Amine
  • Organic oxygen compound
  • Organic nitrogen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Organic oxide
  • Organonitrogen compound
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
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 Solubility0.44 g/LALOGPS
logP-0.59ALOGPS
logP-1.2ChemAxon
logS-2.8ALOGPS
pKa (Strongest Acidic)1.75ChemAxon
pKa (Strongest Basic)9.31ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area102.42 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity74.62 m³·mol⁻¹ChemAxon
Polarizability29.99 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00kf-3690000000-8a203209ee26cc9d81b2Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-01bi-9427100000-83bbdc724a92bedb9dd9Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-007c-0090000000-c072e5e5207b8c910fb0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0036-0590000000-b615c774781c63631475Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001j-1900000000-2b7cf789bff4868649b5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0090000000-016a1ced5998391f910dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000f-0290000000-f825e5f837e939c27da6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052g-8980000000-5333ae5b5ce67dd5e54dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0290000000-993c9e1d7e7cf2f7fc90Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00mn-0790000000-ad5581853fcf6bba5c6fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00mn-2920000000-a796fcd75cb858a9a779Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0090000000-19de8b5ab0e62272a9e4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-007c-0190000000-eab8f030770e8aaaba37Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001m-1930000000-765209de6319e55c489eSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
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 IDNot Available
HMDB IDHMDB0034881
FooDB IDFDB013456
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID35013791
ChEBI IDNot Available
PubChem Compound ID131751635
Kegg Compound IDNot Available
YMDB IDYMDB01492
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.