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Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2016-02-11 01:03:15 UTC
HMDB IDHMDB00706
Secondary Accession Numbers
  • HMDB06113
Metabolite Identification
Common NameL-Aspartyl-L-phenylalanine
DescriptionThis is a metabolic byproduct of aspartame (Nutrasweet). Aspartame is the methyl ester of aspartylphenylalanine. After hydrolysis of the ester bond in the intestinal lumen, the dipeptide is apparently absorbed and digested in the same manner as dipeptides derived from protein digestion. There are several Asp-Phe dipeptidases that degrade this peptide. It has been suggested that individuals with aspartame allergies may be defficient in this peptidase. (PMID 3743970 ). It has been observed that the N-beta-L-aspartyl-L-phenylalanine (a breakdown product of Asn-Phe) is a naturally occurring peptide found in both blood and urine.(PMID: 2723819 ).
Structure
Thumb
Synonyms
ValueSource
alpha-AspartylphenylalanineChEBI
Aspartyl-phenylalanineChEBI
AspartylphenylalanineChEBI
DemethylaspartameChEBI
DFChEBI
L-alpha-Asp-L-pheChEBI
L-Asp-L-pheChEBI
L-Aspartyl-L-phenylalanineChEBI
a-AspartylphenylalanineGenerator
α-aspartylphenylalanineGenerator
L-a-Asp-L-pheGenerator
L-α-asp-L-pheGenerator
3-amino-N-(a-Carboxyphenethyl)-succinamic acid stereoisomerHMDB
3-amino-N-(Carboxyphenethyl)-succinamic acid stereoisomerHMDB
a-L-Aspartyl-L-phenylalanineHMDB
alpha-L-Aspartyl-L-phenylalanineHMDB
L-a-Aspartyl-L-phenylalanineHMDB
L-alpha-Aspartyl-L-phenylalanineHMDB
N-L-a-Aspartyl-L-phenylalanineHMDB
N-L-alpha-Aspartyl-L-phenylalanineHMDB
N-L-Aspartyl-L-phenylalanineHMDB
Chemical FormulaC13H16N2O5
Average Molecular Weight280.2765
Monoisotopic Molecular Weight280.105921632
IUPAC Name(3S)-3-amino-3-{[(1S)-1-carboxy-2-phenylethyl]carbamoyl}propanoic acid
Traditional NameL-aspartyl-L-phenylalanine
CAS Registry Number13433-09-5
SMILES
N[C@@H](CC(O)=O)C(=O)N[C@@H](CC1=CC=CC=C1)C(O)=O
InChI Identifier
InChI=1S/C13H16N2O5/c14-9(7-11(16)17)12(18)15-10(13(19)20)6-8-4-2-1-3-5-8/h1-5,9-10H,6-7,14H2,(H,15,18)(H,16,17)(H,19,20)/t9-,10-/m0/s1
InChI KeyInChIKey=YZQCXOFQZKCETR-UWVGGRQHSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as peptides. These are compounds containing an amide derived from two or more amino carboxylic acid molecules (the same or different) by formation of a covalent bond from the carbonyl carbon of one to the nitrogen atom of another.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentPeptides
Alternative Parents
Substituents
  • Alpha peptide
  • N-acyl-aliphatic-alpha amino acid
  • N-acyl-alpha amino acid or derivatives
  • N-acyl-alpha-amino acid
  • Alpha-amino acid amide
  • 3-phenylpropanoic-acid
  • N-acyl-l-alpha-amino acid
  • Amphetamine or derivatives
  • Alpha-amino acid or derivatives
  • N-substituted-alpha-amino acid
  • Amino fatty acid
  • Fatty acyl
  • Benzenoid
  • N-acyl-amine
  • Fatty amide
  • Dicarboxylic acid or derivatives
  • Monocyclic benzene moiety
  • Secondary carboxylic acid amide
  • Carboxamide group
  • Carboxylic acid
  • Carboxylic acid amide
  • Hydrocarbon derivative
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Carbonyl group
  • Amine
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
Origin
  • Food
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point236 - 239 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility1.14 mg/mLALOGPS
logP-2.4ALOGPS
logP-2.8ChemAxon
logS-2.4ALOGPS
pKa (Strongest Acidic)3.17ChemAxon
pKa (Strongest Basic)8.53ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area129.72 Å2ChemAxon
Rotatable Bond Count7ChemAxon
Refractivity68.45 m3·mol-1ChemAxon
Polarizability27.39 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-001i-0390000000-7b0a372df9ac94084afeView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-00di-3900000000-87243f88c85294b0b9c0View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-00di-7900000000-d2b84cae5c8bb909a375View in MoNA
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Biological Properties
Cellular LocationsNot Available
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.018 +/- 0.004 uMAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified0.29 +/- 0.10 umol/mmol creatinineAdult (>18 years old)FemaleNormal details
UrineDetected and Quantified0.21 +/- 0.04 umol/mmol creatinineAdult (>18 years old)MaleNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB002275
KNApSAcK IDNot Available
Chemspider ID84028
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB00706
Metagene LinkHMDB00706
METLIN ID5674
PubChem Compound93078
PDB IDNot Available
ChEBI ID385866
References
Synthesis ReferenceMarahiel, Mohamed Abdalla; Quaedflieg, Peter Jan Leonard Mario; Sonke, Theodorus. Production of a-L-aspartyl-L-phenylalanine using chimeric non-ribosomal dipeptide synthetase. PCT Int. Appl. (2004), 51 pp.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Burton EG, Schoenhard GL, Hill JA, Schmidt RE, Hribar JD, Kotsonis FN, Oppermann JA: Identification of N-beta-L-aspartyl-L-phenylalanine as a normal constituent of human plasma and urine. J Nutr. 1989 May;119(5):713-21. [2723819 ]
  2. Tobey NA, Heizer WD: Intestinal hydrolysis of aspartylphenylalanine--the metabolic product of aspartame. Gastroenterology. 1986 Oct;91(4):931-7. [3743970 ]