Record Information
Version1.0
Creation date2010-04-08 22:04:31 UTC
Update date2018-05-28 23:01:18 UTC
Primary IDFDB000299
Secondary Accession NumbersNot Available
Chemical Information
FooDB Namep-Coumaroyl aspartic acid
DescriptionN-[4'-hydroxy-(E)-cinnamoyl]-L-aspartic acid belongs to the class of organic compounds known as aspartic acid and derivatives. Aspartic acid and derivatives are compounds containing an aspartic acid or a derivative thereof resulting from reaction of aspartic acid at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. N-[4'-hydroxy-(E)-cinnamoyl]-L-aspartic acid is an extremely weak basic (essentially neutral) compound (based on its pKa).
CAS Number151435-24-4
Structure
Thumb
Synonyms
SynonymSource
N-[4'-Hydroxy-(e)-cinnamoyl]-L-aspartateGenerator
2-{[(2E)-1-hydroxy-3-(4-hydroxyphenyl)prop-2-en-1-ylidene]amino}butanedioateGenerator
p-Coumaroyl aspartateGenerator
(+)-N-[4'-Hydroxy-(E)-cinnamoyl]-L-aspartic acidmanual
N-[4'-Hydroxy-(E)-cinnamoyl]-L-aspartic acidmanual
N-p-Coumaroylaspartic acidmanual
Predicted Properties
PropertyValueSource
Water Solubility0.42 g/LALOGPS
logP1.13ALOGPS
logP0.65ChemAxon
logS-2.8ALOGPS
pKa (Strongest Acidic)3.45ChemAxon
pKa (Strongest Basic)-0.7ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area123.93 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity68.37 m³·mol⁻¹ChemAxon
Polarizability26.94 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC13H13NO6
IUPAC name2-[(2E)-3-(4-hydroxyphenyl)prop-2-enamido]butanedioic acid
InChI IdentifierInChI=1S/C13H13NO6/c15-9-4-1-8(2-5-9)3-6-11(16)14-10(13(19)20)7-12(17)18/h1-6,10,15H,7H2,(H,14,16)(H,17,18)(H,19,20)/b6-3+
InChI KeyFKBRNPNAUOXZMQ-ZZXKWVIFSA-N
Isomeric SMILESOC(=O)CC(NC(=O)\C=C\C1=CC=C(O)C=C1)C(O)=O
Average Molecular Weight279.2454
Monoisotopic Molecular Weight279.074287153
Classification
Description Belongs to the class of organic compounds known as aspartic acid and derivatives. Aspartic acid and derivatives are compounds containing an aspartic acid or a derivative thereof resulting from reaction of aspartic acid at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentAspartic acid and derivatives
Alternative Parents
Substituents
  • Aspartic acid or derivatives
  • N-acyl-alpha amino acid or derivatives
  • N-acyl-alpha-amino acid
  • Cinnamic acid amide
  • Cinnamic acid or derivatives
  • Coumaric acid or derivatives
  • Hydroxycinnamic acid or derivatives
  • Styrene
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Monocyclic benzene moiety
  • Benzenoid
  • Dicarboxylic acid or derivatives
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Carboxylic acid
  • Organic nitrogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Carbonyl group
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Biological location:

Source:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSp-Coumaroyl aspartic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0002-1920000000-e5f920a4103ad0440027Spectrum
Predicted GC-MSp-Coumaroyl aspartic acid, 3 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-01di-6396800000-13cb035e82b526a05892Spectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-1590000000-795e7643a1771bcbadc4Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00ei-8960000000-3acfa2ebc7342bbddf7aSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-9500000000-d7f40389bc45f8349d88Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0059-0290000000-88ec740846831a16b536Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01sj-1890000000-a09d055e66c3b93d46f5Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01p6-9700000000-35dd972c48daa2681195Spectrum
NMRNot Available
ChemSpider ID32175166
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID24891369
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer ID552
DrugBank IDNot Available
HMDB IDHMDB29234
CRC / DFC (Dictionary of Food Compounds) IDHJB19-Y:MWS88-P
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General Reference
  1. Stark T, Bareuther S, Hofmann T: Molecular definition of the taste of roasted cocoa nibs (Theobroma cacao) by means of quantitative studies and sensory experiments. J Agric Food Chem. 2006 Jul 26;54(15):5530-9. Pubmed [Structure]
Content Reference