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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-12 03:02:57 UTC
Update Date2019-01-11 20:00:58 UTC
HMDB IDHMDB0041370
Secondary Accession Numbers
  • HMDB41370
Metabolite Identification
Common NameNa-p-Hydroxycoumaroyltryptophan
DescriptionNa-p-Hydroxycoumaroyltryptophan is found in coffee and coffee products. Na-p-Hydroxycoumaroyltryptophan is a constituent of green coffee beans (Coffea canephora var. robusta) (Rubiaceae).
Structure
Data?1547236858
SynonymsNot Available
Chemical FormulaC20H18N2O4
Average Molecular Weight350.3679
Monoisotopic Molecular Weight350.126657074
IUPAC Name2-[(2E)-3-(4-hydroxyphenyl)prop-2-enamido]-3-(1H-indol-3-yl)propanoic acid
Traditional Name2-[(2E)-3-(4-hydroxyphenyl)prop-2-enamido]-3-(1H-indol-3-yl)propanoic acid
CAS Registry NumberNot Available
SMILES
OC(=O)C(CC1=CNC2=C1C=CC=C2)NC(=O)\C=C\C1=CC=C(O)C=C1
InChI Identifier
InChI=1S/C20H18N2O4/c23-15-8-5-13(6-9-15)7-10-19(24)22-18(20(25)26)11-14-12-21-17-4-2-1-3-16(14)17/h1-10,12,18,21,23H,11H2,(H,22,24)(H,25,26)/b10-7+
InChI KeyIDUPBPKKEQWWCP-JXMROGBWSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as n-acyl-alpha amino acids. These 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
  • Coumaric acid or derivatives
  • Hydroxycinnamic acid or derivatives
  • Indolyl carboxylic acid derivative
  • 3-alkylindole
  • Indole
  • Indole or derivatives
  • Styrene
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Monocyclic benzene moiety
  • Benzenoid
  • Substituted pyrrole
  • Pyrrole
  • Heteroaromatic compound
  • Secondary carboxylic acid amide
  • Carboxamide group
  • Organoheterocyclic compound
  • Azacycle
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Organooxygen compound
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Carbonyl group
  • Organonitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Role

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point208 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0054 g/LALOGPS
logP3.2ALOGPS
logP3.05ChemAxon
logS-4.8ALOGPS
pKa (Strongest Acidic)3.96ChemAxon
pKa (Strongest Basic)0.7ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area102.42 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity98.04 m³·mol⁻¹ChemAxon
Polarizability36.75 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0002-0901000000-116ee215d9b125e0cd3bJSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-004i-4239300000-c714ac237efe8a7b740aJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0zgi-0519000000-3439835289393c5b6577JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-0912000000-8ef7af860f5fcaf5c322JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-1900000000-b8dac02b71c4d4ede956JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0019000000-b1975c14aba879ff1fd2JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0532-1968000000-6b162ebd20a9bb528087JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05mo-4900000000-a4e56b1a0c8116424c00JSpectraViewer | MoNA
Biological Properties
Cellular Locations
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB021295
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound24891366
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .