Record Information
Version1.0
Creation date2011-09-21 00:08:16 UTC
Update date2015-10-09 22:30:08 UTC
Primary IDFDB022084
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameN-Acetyl-L-phenylalanine
DescriptionAcetylphenylalanine is a hazardous amphipathic metabolite of phenylalanine. It appears in large amount in urine of patients with phenylketonuria which is a human genetic disorder due to the lack of phenylalanine hydroxylase, the enzyme necessary to metabolize phenylalanine to tyrosine. Acetylphenylalanine is a product of enzyme phenylalanine N-acetyltransferase [EC 2.3.1.53] in the pathway phenylalanine metabolism. (KEGG; Wikipedia) [HMDB]
CAS Number2018-61-3
Structure
Thumb
Synonyms
SynonymSource
Acetyl-L-phenylalanineChEBI
AcetylphenylalanineChEBI
L-N-AcetylphenylalanineChEBI
N-AcetylphenylalanineChEBI
N-Acetyl-3-phenyl-L-alanineHMDB
N-Acetyl-L-phenalanineHMDB
N-Acetylphenylalanine, (D,L)-isomer, 3H-labeledHMDB
N-Acetylphenylalanine, (L)-isomerHMDB
N-Acetylphenylalanine, (L)-isomer, 3H-labeledHMDB
N-Acetylphenylalanine, (D)-isomerHMDB
N-acetyl-3-phenyl-L-Alaninehmdb
N-Acetyl-l-phenalaninehmdb
N-Acetyl-L-phenylalaninehmdb
Predicted PropertiesNot Available
Chemical FormulaC11H13NO3
IUPAC name
InChI IdentifierInChI=1S/C11H13NO3/c1-8(13)12-10(11(14)15)7-9-5-3-2-4-6-9/h2-6,10H,7H2,1H3,(H,12,13)(H,14,15)/t10-/m0/s1
InChI KeyCBQJSKKFNMDLON-JTQLQIEISA-N
Isomeric SMILESCC(=O)N[C@@H](CC1=CC=CC=C1)C(O)=O
Average Molecular Weight207.2258
Monoisotopic Molecular Weight207.089543287
Classification
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
  • 3-phenylpropanoic-acid
  • Amphetamine or derivatives
  • Monocyclic benzene moiety
  • Benzenoid
  • Carboximidic acid
  • Carboximidic acid derivative
  • Carboxylic acid
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Monocarboxylic acid or derivatives
  • Organic nitrogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Carbonyl group
  • Organic oxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Source:

Biological location:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MSN-Acetyl-L-phenylalanine, 2 TMS, GC-MS Spectrumsplash10-00kf-3980000000-205dc96635b498baa46cSpectrum
GC-MSN-Acetyl-L-phenylalanine, 1 TMS, GC-MS Spectrumsplash10-00dl-3920000000-50af7cdc34df34b89e91Spectrum
GC-MSN-Acetyl-L-phenylalanine, non-derivatized, GC-MS Spectrumsplash10-00kf-3980000000-205dc96635b498baa46cSpectrum
GC-MSN-Acetyl-L-phenylalanine, non-derivatized, GC-MS Spectrumsplash10-00dl-3920000000-50af7cdc34df34b89e91Spectrum
GC-MSN-Acetyl-L-phenylalanine, non-derivatized, GC-MS Spectrumsplash10-0fr7-1950000000-8c9c63efeb473bcf7625Spectrum
GC-MSN-Acetyl-L-phenylalanine, non-derivatized, GC-MS Spectrumsplash10-00dl-2920000000-f0ce2160cf1eb9d38d56Spectrum
GC-MSN-Acetyl-L-phenylalanine, non-derivatized, GC-MS Spectrumsplash10-0f6x-2910000000-33afe725162942dc296aSpectrum
Predicted GC-MSN-Acetyl-L-phenylalanine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0006-9400000000-2c91eb9a78faef00e1daSpectrum
Predicted GC-MSN-Acetyl-L-phenylalanine, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00dl-9110000000-e910d5b4824d2e88d697Spectrum
Predicted GC-MSN-Acetyl-L-phenylalanine, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSN-Acetyl-L-phenylalanine, TMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSN-Acetyl-L-phenylalanine, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSN-Acetyl-L-phenylalanine, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-014i-0900000000-9e69c187ac85603658262012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-014i-0900000000-04559809a9c6261f18b62012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0ufr-5900000000-a8bb0fc573e6143527aa2012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-0a4i-0090000000-2dcdf0ed503251026e402012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-03di-2920000000-7447f1e30d868cae5af62012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-0lxy-8900000000-3b53da8f8106adfdd6772012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-0pbc-9400000000-1737db9a05bf29f3701a2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-0a4l-9100000000-f015dd2066ebbefec15a2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-0a4l-1960000000-20faf15c3d02bbe80ad22012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-00di-0900000000-891ecddb54dab32f4dce2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-00di-1900000000-6867cba730dee87122652012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-00di-2900000000-2e77f5a51bec17ed674e2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-0udi-4900000000-c9aadc8231b14121aa8c2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positivesplash10-02tc-0900000000-ac3b438665d0b035a7e22012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positivesplash10-00di-0900000000-a426a7fbff06e9213f592012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positivesplash10-00di-0900000000-0d8dd7876525745785ff2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positivesplash10-0fdo-6900000000-ad4d31f8b5e3e04744162012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a4i-0090000000-2dcdf0ed503251026e402017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-03di-2920000000-7447f1e30d868cae5af62017-09-14View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0btc-2950000000-2865ae294df6193f5a752016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-044l-2900000000-1b1f3d364775a1619b262016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9200000000-9bb5ea6eb4c3ab49ee322016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-2890000000-293238d6264d01ab86c42016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0900-5910000000-b912a04d31d0b03a85522016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-9200000000-1b69d466f84616cfe6282016-09-12View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CD3OD, experimental)Spectrum
ChemSpider ID67404
ChEMBL IDCHEMBL55743
KEGG Compound IDC03519
Pubchem Compound ID74839
Pubchem Substance IDNot Available
ChEBI ID16259
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB00512
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
Enzymes
NameGene NameUniProt ID
Glycine N-acyltransferaseGLYATQ6IB77
Glycine N-acyltransferase-like protein 1GLYATL1Q969I3
Glycine N-acyltransferase-like protein 2GLYATL2Q8WU03
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference