Record Information
Version1.0
Creation date2010-04-08 22:04:31 UTC
Update date2019-11-27 17:02:27 UTC
Primary IDFDB000298
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameCaffeoyl aspartic acid
DescriptionCaffeoyl 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. Caffeoyl aspartic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). Caffeoyl aspartic acid is found, on average, in the highest concentration within cocoa powders and hot chocolates. This could make caffeoyl aspartic acid a potential biomarker for the consumption of these foods.
CAS Number860295-20-1
Structure
Thumb
Synonyms
SynonymSource
Caffeoyl aspartateGenerator
(+)-N-[3',4'-Dihydroxy-(e)-cinnamoyl]-L-aspartic acidHMDB
N-Caffeoylaspartic acidHMDB
(+)-N-[3',4'-Dihydroxy-(E)-cinnamoyl]-L-aspartic acidmanual
Predicted Properties
PropertyValueSource
Water Solubility0.55 g/LALOGPS
logP1.47ALOGPS
logP0.35ChemAxon
logS-2.7ALOGPS
pKa (Strongest Acidic)3.19ChemAxon
pKa (Strongest Basic)0.69ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area144.16 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity70.35 m³·mol⁻¹ChemAxon
Polarizability27.84 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC13H13NO7
IUPAC name2-[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enamido]butanedioic acid
InChI IdentifierInChI=1S/C13H13NO7/c15-9-3-1-7(5-10(9)16)2-4-11(17)14-8(13(20)21)6-12(18)19/h1-5,8,15-16H,6H2,(H,14,17)(H,18,19)(H,20,21)/b4-2+
InChI KeyYNHFZQQNJPOYRC-DUXPYHPUSA-N
Isomeric SMILESOC(=O)CC(NC(=O)\C=C\C1=CC(O)=C(O)C=C1)C(O)=O
Average Molecular Weight295.2448
Monoisotopic Molecular Weight295.069201775
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
  • N-acyl-alpha amino acid or derivatives
  • Cinnamic acid amide
  • Cinnamic acid or derivatives
  • Hydroxycinnamic acid or derivatives
  • Catechol
  • Styrene
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • 1-hydroxy-4-unsubstituted benzenoid
  • Benzenoid
  • Monocyclic benzene moiety
  • Dicarboxylic acid or derivatives
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Carboxylic acid
  • Carbonyl group
  • Organooxygen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Organic oxide
  • Organic nitrogen compound
  • Organonitrogen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Biological role:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
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
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-03fr-2960000000-52338e0e7633b2e19048View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positivesplash10-0a4i-7219070000-4a7d3dfe7fa0eea2a3c1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-003s-1590000000-f7fa4becc100b31af02cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0079-9860000000-8b849d06f12d20207047View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-9500000000-05e18ea6b0c65b18b9c9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0f6x-0290000000-21661e5932a28ee7f403View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0w5c-1690000000-2d6afb93ddddb93d1964View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03du-9700000000-78b251fb070d0d39b656View in MoNA
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID24891368
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer ID551
DrugBank IDNot Available
HMDB IDHMDB29294
CRC / DFC (Dictionary of Food Compounds) IDHJB19-Y:OVP05-O
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— Rothwell JA, Pérez-Jiménez J, Neveu V, Medina-Ramon A, M'Hiri N, Garcia Lobato P, Manach C, Knox K, Eisner R, Wishart D, Scalbert A. (2013) Phenol-Explorer 3.0: a major update of the Phenol-Explorer database to incorporate data on the effects of food processing on polyphenol content. Database, 10.1093/database/bat070.