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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2019-05-16 17:25:38 UTC
HMDB IDHMDB0000706
Secondary Accession Numbers
  • HMDB0006113
  • HMDB0028760
  • HMDB00706
  • HMDB06113
  • HMDB28760
Metabolite Identification
Common NameAspartylphenylalanine
DescriptionAspartylphenylalanine is a dipeptide composed of aspartate and phenylalanine, and is a metabolic byproduct of its methyl ester, aspartame (Nutrasweet). 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 deficient in this peptidase (PMID: 3743970 ). It has been observed that N-beta-aspartylphenylalanine (a breakdown product of Asp-Phe) is a naturally occurring peptide found in both blood and urine (PMID: 2723819 ).
Structure
Data?1558027538
Synonyms
ValueSource
alpha-AspartylphenylalanineChEBI
Aspartyl-phenylalanineChEBI
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
AspartylphenylalanineChEBI
Asp-PheHMDB
Aspartate phenylalanine dipeptideHMDB
Aspartate-phenylalanine dipeptideHMDB
Aspartic acid phenylalanine dipeptideHMDB
Aspartic acid-phenylalanine dipeptideHMDB
D-F dipeptideHMDB
DF dipeptideHMDB
L-α-Aspartyl-L-phenylalanineHMDB
N-AspartylphenylalanineHMDB
N-L-alpha-AspartylphenylalanineHMDB
N-L-α-Aspartyl-L-phenylalanineHMDB
N-L-α-AspartylphenylalanineHMDB
N-alpha-AspartylphenylalanineHMDB
N-alpha-L-Aspartyl-L-phenylalanineHMDB
N-α-AspartylphenylalanineHMDB
N-α-L-Aspartyl-L-phenylalanineHMDB
alpha-Asp-PheHMDB
alpha-L-Asp-L-PheHMDB
α-Asp-PheHMDB
α-L-Asp-L-PheHMDB
α-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
Description belongs to the class of organic compounds known as peptides. Peptides 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
  • 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:

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
Polarizability27.38 ųChemAxon
Number of Rings1ChemAxon
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, Positivesplash10-0006-9210000000-99b1c60ce2664aa530b1JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-06r6-9525000000-3a4d24d1ee1454572cc1JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-001i-0390000000-7b0a372df9ac94084afeJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-00di-3900000000-87243f88c85294b0b9c0JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-00di-7900000000-d2b84cae5c8bb909a375JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT , positivesplash10-03di-0090000000-a5bb00a5f0b23af52395JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-2190000000-ada65fa05610fc51f76eJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00dr-9540000000-9ed983dde86880aa4527JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-b3417045792cf6898dc6JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-01ti-0190000000-f75d1eee083251e5adf3JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-2790000000-c95ba2116f0b468c3d39JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03kc-8900000000-14070390cd9111dd4545JSpectraViewer | MoNA
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableJSpectraViewer
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Feces
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.018 +/- 0.004 uMAdult (>18 years old)Both
Normal
details
FecesDetected but not Quantified Adult (>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
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not Quantified Adult (>18 years old)Both
Colorectal cancer
details
FecesDetected but not Quantified Adult (>18 years old)BothColorectal Cancer details
FecesDetected but not Quantified Adult (>18 years old)Both
Colorectal cancer
details
Associated Disorders and Diseases
Disease References
Colorectal cancer
  1. Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ]
  2. Sinha R, Ahn J, Sampson JN, Shi J, Yu G, Xiong X, Hayes RB, Goedert JJ: Fecal Microbiota, Fecal Metabolome, and Colorectal Cancer Interrelations. PLoS One. 2016 Mar 25;11(3):e0152126. doi: 10.1371/journal.pone.0152126. eCollection 2016. [PubMed:27015276 ]
  3. Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound 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 ID73830
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 ]