L-Aspartyl-L-phenylalanine (CHEM021629)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 18:08:41 UTC
Update Date2016-11-09 01:17:20 UTC
Accession NumberCHEM021629
Identification
Common NameL-Aspartyl-L-phenylalanine
ClassSmall Molecule
DescriptionA dipeptide formed from L-alpha-aspartyl and L-phenylalanine residues. It is obtained after the hydrolysis of aspartame in intestinal lumen.
Contaminant Sources
  • FooDB Chemicals
  • HMDB Contaminants - Urine
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
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
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
AspartylphenylalanineChEBI
Chemical FormulaC13H16N2O5
Average Molecular Mass280.277 g/mol
Monoisotopic Mass280.106 g/mol
CAS Registry Number13433-09-5
IUPAC Name(3S)-3-amino-3-{[(1S)-1-carboxy-2-phenylethyl]carbamoyl}propanoic acid
Traditional NameL-aspartyl-L-phenylalanine
SMILESN[C@@H](CC(O)=O)C(=O)N[C@@H](CC1=CC=CC=C1)C(O)=O
InChI IdentifierInChI=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
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot 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 FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9210000000-99b1c60ce2664aa530b1Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-06r6-9525000000-3a4d24d1ee1454572cc1Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-001i-0390000000-7b0a372df9ac94084afeSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-00di-3900000000-87243f88c85294b0b9c0Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-00di-7900000000-d2b84cae5c8bb909a375Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT , positivesplash10-03di-0090000000-a5bb00a5f0b23af52395Spectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-0w4l-6900000000-78b037a83ec30bbf4935Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-03di-0790000000-591db14e072572b92070Spectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-03fr-2900000000-e2b57705f5b8d696a79dSpectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-00di-2910000000-93b5544c57de969784cdSpectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-00di-4900000000-ceb2492c0254b28ed94aSpectrum
LC-MS/MSLC-MS/MS Spectrum - 0V, Positivesplash10-001i-0490000000-4d232314dbe9e869b9efSpectrum
LC-MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-00xr-0920000000-488268e5e8c985cd3313Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-014i-5900000000-e4b26f79b07132c2f7a2Spectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-006x-9500000000-8e6d999331cec9d7dd42Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-01bi-0790000000-fd787d6145e4675c5ddfSpectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-00di-5910000000-1989861c1aeddffbc5f6Spectrum
LC-MS/MSLC-MS/MS Spectrum - 0V, Positivesplash10-001i-0091000000-1eef70f739bf19b7a430Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0gi9-1791000000-e03a7de1b774d1b01b0fSpectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-00di-2910000000-d15779875dee04b8ecccSpectrum
LC-MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-03di-0920000000-ff051eab84623ab1d4beSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-2190000000-ada65fa05610fc51f76eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00dr-9540000000-9ed983dde86880aa4527Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-b3417045792cf6898dc6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-01ti-0190000000-f75d1eee083251e5adf3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-2790000000-c95ba2116f0b468c3d39Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03kc-8900000000-14070390cd9111dd4545Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0000706
FooDB IDFDB002275
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN ID5674
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID84028
ChEBI ID73830
PubChem Compound ID93078
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=22200573
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=23218487
3. Marahiel, 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.
4. 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.
5. Tobey NA, Heizer WD: Intestinal hydrolysis of aspartylphenylalanine--the metabolic product of aspartame. Gastroenterology. 1986 Oct;91(4):931-7.
6. 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.
7. 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.
8. 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.
9. 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.
10. 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.
11. Pattanaargson S, Sanchavanakit C: Aspartame degradation study using electrospray ionization mass spectrometry. Rapid Commun Mass Spectrom. 2000;14(11):987-93.
12. 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.
13. Leung SS, Grant DJ: Solid state stability studies of model dipeptides: aspartame and aspartylphenylalanine. J Pharm Sci. 1997 Jan;86(1):64-71.