N-Caffeoyltryptophan (CHEM023468)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 21:04:49 UTC
Update Date2016-11-09 01:17:43 UTC
Accession NumberCHEM023468
Identification
Common NameN-Caffeoyltryptophan
ClassSmall Molecule
DescriptionN-Caffeoyltryptophan is found in coffee and coffee products. N-Caffeoyltryptophan is a constituent of green coffee beans
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
2-{[(2E)-3-(3,4-dihydroxyphenyl)-1-hydroxyprop-2-en-1-ylidene]amino}-3-(1H-indol-3-yl)propanoateHMDB
Chemical FormulaC20H18N2O5
Average Molecular Mass366.367 g/mol
Monoisotopic Mass366.122 g/mol
CAS Registry Number109163-69-1
IUPAC Name2-[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enamido]-3-(1H-indol-3-yl)propanoic acid
Traditional Name2-[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enamido]-3-(1H-indol-3-yl)propanoic acid
SMILESOC(=O)C(CC1=CNC2=C1C=CC=C2)NC(=O)\C=C\C1=CC(O)=C(O)C=C1
InChI IdentifierInChI=1S/C20H18N2O5/c23-17-7-5-12(9-18(17)24)6-8-19(25)22-16(20(26)27)10-13-11-21-15-4-2-1-3-14(13)15/h1-9,11,16,21,23-24H,10H2,(H,22,25)(H,26,27)/b8-6+
InChI KeyXITPERBRJNUFSB-SOFGYWHQSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as n-acyl-alpha amino acids. N-acyl-alpha amino acids are compounds containing an alpha amino acid which bears an acyl group at its terminal nitrogen atom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentN-acyl-alpha amino acids
Alternative Parents
Substituents
  • N-acyl-alpha-amino acid
  • Cinnamic acid amide
  • Cinnamic acid or derivatives
  • Hydroxycinnamic acid or derivatives
  • Indolyl carboxylic acid derivative
  • 3-alkylindole
  • Indole
  • Indole or derivatives
  • Catechol
  • Styrene
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Benzenoid
  • Substituted pyrrole
  • Monocyclic benzene moiety
  • Pyrrole
  • Heteroaromatic compound
  • Secondary carboxylic acid amide
  • Carboxamide group
  • Azacycle
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carbonyl group
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic nitrogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • 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 Solubility0.014 g/LALOGPS
logP2.94ALOGPS
logP2.75ChemAxon
logS-4.4ALOGPS
pKa (Strongest Acidic)3.71ChemAxon
pKa (Strongest Basic)0.7ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area122.65 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity100.02 m³·mol⁻¹ChemAxon
Polarizability37.66 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-03di-0901000000-b0304ea99bf1400bf610Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-014i-4101890000-cd0b9ff7a59bfc83b7f4Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0gb9-0659000000-1330b0dba7e115b3a200Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-0921000000-76dae2a27a423fe1e1faSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-0900000000-80f8e3c5045d079160beSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0219000000-71bb929d9587814879e3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0i99-1946000000-af124d71126824aed774Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00kf-6900000000-6d33fcd6f9816ffd6006Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00xr-0219000000-44dde8ed4cfa6e0ccb38Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01bl-0924000000-88de6bdca53f6b6ac8c7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000i-0900000000-399303410db4ee033e50Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03xs-0908000000-695299bb4f62ad02350eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00dl-0905000000-6ea0d9047486b0276e2dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-02a9-0900000000-00d8e62cd8d3618dde6eSpectrum
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 IDHMDB0029830
FooDB IDFDB001045
Phenol Explorer IDNot Available
KNApSAcK IDC00054102
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID8604387
ChEBI ID175694
PubChem Compound ID10428959
Kegg Compound IDNot Available
YMDB IDNot Available
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.