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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:29:30 UTC
Update Date2019-01-11 19:37:43 UTC
HMDB IDHMDB0029295
Secondary Accession Numbers
  • HMDB29295
Metabolite Identification
Common NameCaffeoyl tyrosine
DescriptionCaffeoyl tyrosine is a constituent of cocoa flowers and robusta coffee beans [CCD]
Structure
Data?1547235463
Synonyms
ValueSource
DeoxyclovamideHMDB
N-trans-CaffeoyltyrosineHMDB
N-[3',4'-Dihydroxy-(e)-cinnamoyl]-L-tyrosineHMDB
Chemical FormulaC18H17NO6
Average Molecular Weight343.3307
Monoisotopic Molecular Weight343.105587281
IUPAC Name2-[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enamido]-3-(4-hydroxyphenyl)propanoic acid
Traditional Name2-[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enamido]-3-(4-hydroxyphenyl)propanoic acid
CAS Registry Number124027-56-1
SMILES
OC(=O)C(CC1=CC=C(O)C=C1)NC(=O)\C=C\C1=CC=C(O)C(O)=C1
InChI Identifier
InChI=1S/C18H17NO6/c20-13-5-1-11(2-6-13)9-14(18(24)25)19-17(23)8-4-12-3-7-15(21)16(22)10-12/h1-8,10,14,20-22H,9H2,(H,19,23)(H,24,25)/b8-4+
InChI KeyJRXLVUMFJASLDR-XBXARRHUSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as n-acyl-aliphatic-alpha amino acids. These are alpha amino acids carrying a N-acylated aliphatic chain.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentN-acyl-aliphatic-alpha amino acids
Alternative Parents
Substituents
  • N-acyl-aliphatic-alpha amino acid
  • Hydroxycinnamic acid or derivatives
  • Cinnamic acid or derivatives
  • Cinnamic acid amide
  • 3-phenylpropanoic-acid
  • Amphetamine or derivatives
  • Phenylpropene
  • Styrene
  • 1,2-diphenol
  • Phenol
  • Amino fatty acid
  • Fatty acyl
  • Benzenoid
  • Monocyclic benzene moiety
  • Secondary carboxylic acid amide
  • Carboxamide group
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid amide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Source:

Biological location:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.4 mg/mL at 20 °CNot Available
LogP-2.04Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.051 g/LALOGPS
logP2.23ALOGPS
logP2.35ChemAxon
logS-3.8ALOGPS
pKa (Strongest Acidic)3.39ChemAxon
pKa (Strongest Basic)0.7ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area127.09 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity90.92 m³·mol⁻¹ChemAxon
Polarizability34.88 ųChemAxon
Number of Rings2ChemAxon
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, Positivesplash10-08fr-0910000000-c97d515678dae252e781JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positivesplash10-014i-2112095000-6938197ec7fba55e6471JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001l-0925000000-5eff4a2368d6948dd2c0JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-0900000000-9746355ef13e3a83eb1bJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-2900000000-38b3ede11a2664cd91d6JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0349000000-b554ef12553310ea28a1JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03gm-0953000000-7b890e3e3be23713a519JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01ox-6900000000-a1ef157cc1fc1819cfc0JSpectraViewer | MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
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 ID554
FoodDB IDFDB000301
KNApSAcK IDNot Available
Chemspider ID22546930
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound14352555
PDB IDNot Available
ChEBI ID490727
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available