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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2006-05-22 14:17:50 UTC
Update Date2022-09-22 18:34:16 UTC
HMDB IDHMDB0002372
Secondary Accession Numbers
  • HMDB02372
Metabolite Identification
Common NameN-Phenylacetylphenylalanine
DescriptionN-Phenylacetylphenylalanine belongs to the class of organic compounds known as phenylalanine and derivatives. Phenylalanine and derivatives are compounds containing phenylalanine or a derivative thereof resulting from reaction of phenylalanine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. N-Phenylacetylphenylalanine has been detected, but not quantified in, a few different foods, such as anatidaes (Anatidae), chickens (Gallus gallus), and domestic pigs (Sus scrofa domestica). This could make N-phenylacetylphenylalanine a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on N-Phenylacetylphenylalanine.
Structure
Data?1582752246
Synonyms
ValueSource
3-Phenyl-N-(phenylacetyl)-alanineHMDB
L-3-Phenyl-N-(phenylacetyl)-alanineHMDB
N-(Phenylacetyl)-L-phenylalanineHMDB
N-Phenylacetyl-L-phenylalanineHMDB, MeSH
N-Phenylacetylphenylalanine, (D)-isomerMeSH, HMDB
(2S)-2-[(1-Hydroxy-2-phenylethylidene)amino]-3-phenylpropanoateGenerator, HMDB
N-PhenylacetylphenylalanineMeSH
Chemical FormulaC17H17NO3
Average Molecular Weight283.3218
Monoisotopic Molecular Weight283.120843415
IUPAC Name(2S)-3-phenyl-2-(2-phenylacetamido)propanoic acid
Traditional NameN-phenylacetyl-L-phenylalanine
CAS Registry Number738-75-0
SMILES
OC(=O)[C@H](CC1=CC=CC=C1)NC(=O)CC1=CC=CC=C1
InChI Identifier
InChI=1S/C17H17NO3/c19-16(12-14-9-5-2-6-10-14)18-15(17(20)21)11-13-7-3-1-4-8-13/h1-10,15H,11-12H2,(H,18,19)(H,20,21)/t15-/m0/s1
InChI KeyLIIPHJDKZNTNII-HNNXBMFYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as phenylalanine and derivatives. Phenylalanine and derivatives are compounds containing phenylalanine or a derivative thereof resulting from reaction of phenylalanine 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 ParentPhenylalanine and derivatives
Alternative Parents
Substituents
  • Phenylalanine or derivatives
  • N-acyl-alpha-amino acid
  • N-acyl-alpha amino acid or derivatives
  • N-acyl-l-alpha-amino acid
  • 3-phenylpropanoic-acid
  • Amphetamine or derivatives
  • Phenylacetamide
  • Monocyclic benzene moiety
  • Benzenoid
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Hydrocarbon derivative
  • Organic oxide
  • Organic nitrogen compound
  • Organopnictogen compound
  • Carbonyl group
  • Organic oxygen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.027 g/LALOGPS
logP2.39ALOGPS
logP2.73ChemAxon
logS-4ALOGPS
pKa (Strongest Acidic)4.08ChemAxon
pKa (Strongest Basic)-2.6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area66.4 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity79.28 m³·mol⁻¹ChemAxon
Polarizability29.97 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+165.92631661259
DarkChem[M-H]-165.50331661259
DeepCCS[M+H]+165.72930932474
DeepCCS[M-H]-163.37130932474
DeepCCS[M-2H]-196.99530932474
DeepCCS[M+Na]+172.22130932474
AllCCS[M+H]+167.332859911
AllCCS[M+H-H2O]+163.732859911
AllCCS[M+NH4]+170.532859911
AllCCS[M+Na]+171.532859911
AllCCS[M-H]-169.532859911
AllCCS[M+Na-2H]-169.232859911
AllCCS[M+HCOO]-169.132859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
N-PhenylacetylphenylalanineOC(=O)[C@H](CC1=CC=CC=C1)NC(=O)CC1=CC=CC=C13626.0Standard polar33892256
N-PhenylacetylphenylalanineOC(=O)[C@H](CC1=CC=CC=C1)NC(=O)CC1=CC=CC=C12260.5Standard non polar33892256
N-PhenylacetylphenylalanineOC(=O)[C@H](CC1=CC=CC=C1)NC(=O)CC1=CC=CC=C12409.6Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
N-Phenylacetylphenylalanine,1TMS,isomer #1C[Si](C)(C)OC(=O)[C@H](CC1=CC=CC=C1)NC(=O)CC1=CC=CC=C12405.2Semi standard non polar33892256
N-Phenylacetylphenylalanine,1TMS,isomer #2C[Si](C)(C)N(C(=O)CC1=CC=CC=C1)[C@@H](CC1=CC=CC=C1)C(=O)O2410.8Semi standard non polar33892256
N-Phenylacetylphenylalanine,2TMS,isomer #1C[Si](C)(C)OC(=O)[C@H](CC1=CC=CC=C1)N(C(=O)CC1=CC=CC=C1)[Si](C)(C)C2371.9Semi standard non polar33892256
N-Phenylacetylphenylalanine,2TMS,isomer #1C[Si](C)(C)OC(=O)[C@H](CC1=CC=CC=C1)N(C(=O)CC1=CC=CC=C1)[Si](C)(C)C2422.6Standard non polar33892256
N-Phenylacetylphenylalanine,2TMS,isomer #1C[Si](C)(C)OC(=O)[C@H](CC1=CC=CC=C1)N(C(=O)CC1=CC=CC=C1)[Si](C)(C)C3004.3Standard polar33892256
N-Phenylacetylphenylalanine,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)[C@H](CC1=CC=CC=C1)NC(=O)CC1=CC=CC=C12670.5Semi standard non polar33892256
N-Phenylacetylphenylalanine,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)N(C(=O)CC1=CC=CC=C1)[C@@H](CC1=CC=CC=C1)C(=O)O2651.8Semi standard non polar33892256
N-Phenylacetylphenylalanine,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)[C@H](CC1=CC=CC=C1)N(C(=O)CC1=CC=CC=C1)[Si](C)(C)C(C)(C)C2860.2Semi standard non polar33892256
N-Phenylacetylphenylalanine,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)[C@H](CC1=CC=CC=C1)N(C(=O)CC1=CC=CC=C1)[Si](C)(C)C(C)(C)C2820.8Standard non polar33892256
N-Phenylacetylphenylalanine,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)[C@H](CC1=CC=CC=C1)N(C(=O)CC1=CC=CC=C1)[Si](C)(C)C(C)(C)C3147.1Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - N-Phenylacetylphenylalanine GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-7920000000-414527b0d8767edb022a2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - N-Phenylacetylphenylalanine GC-MS (1 TMS) - 70eV, Positivesplash10-006x-9301000000-6bba534fc811e446dd422017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - N-Phenylacetylphenylalanine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Phenylacetylphenylalanine 10V, Negative-QTOFsplash10-001i-0490000000-47fac515ba1e5c7e08a22016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Phenylacetylphenylalanine 20V, Negative-QTOFsplash10-00m3-1940000000-4ac1507005c25d36f8b42016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Phenylacetylphenylalanine 40V, Negative-QTOFsplash10-014l-9700000000-2bb6f7f95d0c2306716f2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Phenylacetylphenylalanine 10V, Negative-QTOFsplash10-03xr-1910000000-f164e21280a47480c5dd2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Phenylacetylphenylalanine 20V, Negative-QTOFsplash10-044m-4910000000-948f26d129049ea5276f2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Phenylacetylphenylalanine 40V, Negative-QTOFsplash10-00r7-7900000000-454ec737db24b4710cdd2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Phenylacetylphenylalanine 10V, Positive-QTOFsplash10-02ai-2890000000-731f005addd7e44b2d792016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Phenylacetylphenylalanine 20V, Positive-QTOFsplash10-014i-1920000000-1a43b8b4de97159d14622016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Phenylacetylphenylalanine 40V, Positive-QTOFsplash10-0006-9300000000-3ae402042e506b3eac682016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Phenylacetylphenylalanine 10V, Positive-QTOFsplash10-00lr-0590000000-c540ae154f5783eaed2c2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Phenylacetylphenylalanine 20V, Positive-QTOFsplash10-00di-1900000000-f83c0d5eac6e344538642021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Phenylacetylphenylalanine 40V, Positive-QTOFsplash10-0006-9600000000-6e9bb33785266131fff22021-09-22Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biospecimen Locations
  • Blood
  • Feces
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
UrineDetected and Quantified6.988 +/- 4.615 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Normal
    • Analysis of 30 no...
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedCancer patients undergoing total body irradiation details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothColorectal Cancer details
UrineDetected and Quantified5.592 +/- 3.046 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Eosinophilic esophagitis
    • Analysis of 30 no...
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 ]
Eosinophilic esophagitis
  1. Slae, M., Huynh, H., Wishart, D.S. (2014). Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work). NA.
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022983
KNApSAcK IDNot Available
Chemspider ID43287
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound47579
PDB IDNot Available
ChEBI ID975589
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Burley SK, Wang AH, Votano JR, Rich A: Antigelling and antisickling bisphenyl oligopeptides and peptide analogues have similar structural features. Biochemistry. 1987 Aug 11;26(16):5091-9. [PubMed:3663644 ]
  2. Votano JR, Altman J, Wilchek M, Gorecki M, Rich A: Potential use of biaromatic L-phenylalanyl derivatives as therapeutic agents in the treatment of sickle cell disease. Proc Natl Acad Sci U S A. 1984 May;81(10):3190-4. [PubMed:6587344 ]