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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2017-12-11 21:46:03 UTC
HMDB IDHMDB0000706
Secondary Accession Numbers
  • HMDB0028760
  • HMDB00706
  • HMDB06113
  • HMDB28760
Metabolite Identification
Common NameAspartylphenylalanine
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
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 KeyYZQCXOFQZKCETR-UWVGGRQHSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities 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.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganic acids and derivatives
Sub ClassCarboxylic acids and derivatives
Direct ParentPeptides
Alternative Parents
Substituents
  • Alpha peptide
  • Phenylalanine or derivatives
  • N-acyl-alpha-amino acid
  • N-acyl-alpha amino acid or derivatives
  • Beta amino acid or derivatives
  • 3-phenylpropanoic-acid
  • Alpha-amino acid or derivatives
  • Amphetamine or derivatives
  • Monocyclic benzene moiety
  • Dicarboxylic acid or derivatives
  • Benzenoid
  • Amino acid or derivatives
  • Amino acid
  • Carboximidic acid derivative
  • Carboxylic acid
  • Carboximidic acid
  • Propargyl-type 1,3-dipolar organic compound
  • Organic 1,3-dipolar compound
  • Organic nitrogen compound
  • Primary aliphatic amine
  • Organonitrogen compound
  • Organooxygen compound
  • Primary amine
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Amine
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Biological Location:

  Biofluid and excreta:

Source:

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 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity68.45 m³·mol⁻¹ChemAxon
Polarizability27.39 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9210000000-99b1c60ce2664aa530b1View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-06r6-9525000000-3a4d24d1ee1454572cc1View in MoNA
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
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT , positivesplash10-03di-0090000000-a5bb00a5f0b23af52395View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-2190000000-ada65fa05610fc51f76eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00dr-9540000000-9ed983dde86880aa4527View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-b3417045792cf6898dc6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-01ti-0190000000-f75d1eee083251e5adf3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-2790000000-c95ba2116f0b468c3d39View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03kc-8900000000-14070390cd9111dd4545View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
Biological Properties
Cellular LocationsNot Available
Biofluid Locations
  • Blood
  • Feces
  • Urine
Tissue LocationNot Available
PathwaysNot Available
NameSMPDB/PathwhizKEGG
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
BiofluidStatusValueAgeSexConditionReferenceDetails
FecesDetected but not Quantified Adult (>18 years old)BothColorectal Cancer details
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
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. [PubMed:2723819 ]
  2. Tobey NA, Heizer WD: Intestinal hydrolysis of aspartylphenylalanine--the metabolic product of aspartame. Gastroenterology. 1986 Oct;91(4):931-7. [PubMed:3743970 ]
  3. Mizuma T, Masubuchi S, Awazu S: Intestinal absorption of stable cyclic dipeptides by the oligopeptide transporter in rat. J Pharm Pharmacol. 1998 Feb;50(2):167-72. [PubMed:9530984 ]
  4. Borke JL, Litwiller RD, Bell MP, Fass DN, McKean DJ, Kumar R: The isolation, characterization and amino terminal sequence of the vitamin D-binding protein (group specific component) from mouse plasma. Int J Biochem. 1988;20(12):1343-9. [PubMed:3243374 ]
  5. Burgert SL, Andersen DW, Stegink LD, Takeuchi H, Schedl HP: Metabolism of aspartame and its L-phenylalanine methyl ester decomposition product by the porcine gut. Metabolism. 1991 Jun;40(6):612-8. [PubMed:1865825 ]
  6. Benoiton NL, Chen FM: 2,4-Dimethyl-5(4H)-oxazolone as reagent for activation and coupling of N-substituted aspartic acid. Int J Pept Protein Res. 1994 Aug;44(2):139-42. [PubMed:7982757 ]
  7. Goodman M, Mattern RH, Gantzel P, Santini A, Iacovino R, Saviano M, Benedetti E: X-ray structures of new dipeptide taste ligands. J Pept Sci. 1998 Jun;4(4):229-38. [PubMed:9680057 ]
  8. Pattanaargson S, Sanchavanakit C: Aspartame degradation study using electrospray ionization mass spectrometry. Rapid Commun Mass Spectrom. 2000;14(11):987-93. [PubMed:10844736 ]
  9. Schwerdt G, Freudinger R, Silbernagl S, Gekle M: Apical uptake of radiolabelled ochratoxin A into Madin-Darby canine kidney cells. Toxicology. 1998 Nov 16;131(2-3):193-202. [PubMed:9928634 ]
  10. Leung SS, Grant DJ: Solid state stability studies of model dipeptides: aspartame and aspartylphenylalanine. J Pharm Sci. 1997 Jan;86(1):64-71. [PubMed:9002461 ]