You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Yeast Metabolome Database.
Identification
YMDB IDYMDB00995
NameD-Phenylalanine
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionD-Phenylalanine, also known as D-phe or DPN, 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. D-Phenylalanine is a very strong basic compound (based on its pKa). D-Phenylalanine may be a unique S. cerevisiae (yeast) metabolite.
Structure
Thumb
Synonyms
  • (-)-beta-Phenylalanine
  • (L)-Phenylalanine
  • (S)-(-)-Phenylalanine
  • (S)-2-amino-3-phenylpropanoate
  • (S)-2-amino-3-phenylpropanoic acid
  • (S)-2-Amino-3-phenylpropionate
  • (S)-2-Amino-3-phenylpropionic acid
  • (S)-alpha-Amino-benzenepropanoate
  • (S)-alpha-Amino-benzenepropanoic acid
  • (S)-alpha-Amino-beta-phenylpropionate
  • (S)-alpha-Amino-beta-phenylpropionic acid
  • (S)-alpha-Aminobenzenepropanoate
  • (S)-alpha-Aminobenzenepropanoic acid
  • (S)-alpha-Aminohydrocinnamate
  • (S)-alpha-Aminohydrocinnamic acid
  • (S)-Phenylalanine
  • 3-Phenyl-L-alanine
  • Alanine, phenyl-, D-
  • alpha-Aminohydrocinnamate
  • alpha-Aminohydrocinnamic acid
  • beta-Phenyl-alpha-alanine
  • beta-Phenyl-L-alanine
  • beta-Phenylalanine
  • D-alpha-Amino-beta-phenylpropionic acid
  • D-Phenylalanine
  • L-2-Amino-3-phenylpropionate
  • L-2-Amino-3-phenylpropionic acid
  • L-Phenylalanine
  • Phe
  • phenyl-Alanine
  • Phenylalamine
  • Phenylalanine
  • Sabiden
  • D-Phe
  • DPN
  • Phenylalanine D-form
  • D-a-Amino-b-phenylpropionate
  • D-a-Amino-b-phenylpropionic acid
  • D-alpha-Amino-beta-phenylpropionate
  • D-Α-amino-β-phenylpropionate
  • D-Α-amino-β-phenylpropionic acid
CAS number673-06-3
WeightAverage: 165.1891
Monoisotopic: 165.078978601
InChI KeyCOLNVLDHVKWLRT-MRVPVSSYSA-N
InChIInChI=1S/C9H11NO2/c10-8(9(11)12)6-7-4-2-1-3-5-7/h1-5,8H,6,10H2,(H,11,12)/t8-/m1/s1
IUPAC Name(2R)-2-amino-3-phenylpropanoic acid
Traditional IUPAC NameD-phenylalanine
Chemical FormulaC9H11NO2
SMILESN[C@H](CC1=CC=CC=C1)C(O)=O
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
  • 3-phenylpropanoic-acid
  • Alpha-amino acid
  • Amphetamine or derivatives
  • D-alpha-amino acid
  • Aralkylamine
  • Monocyclic benzene moiety
  • Benzenoid
  • Amino acid
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organic nitrogen compound
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Primary aliphatic amine
  • Organic oxide
  • Carbonyl group
  • Organopnictogen compound
  • Organic oxygen compound
  • Amine
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Physical Properties
StateSolid
Charge0
Melting point283 °C
Experimental Properties
PropertyValueReference
Water Solubility26.9 mg/mL at 25 oC [YALKOWSKY,SH & DANNENFELSER,RM (1992)]PhysProp
LogP-1.38 [AVDEEF,A (1997)]PhysProp
Predicted Properties
PropertyValueSource
Water Solubility4.14 g/LALOGPS
logP-1.4ALOGPS
logP-1.2ChemAxon
logS-1.6ALOGPS
pKa (Strongest Acidic)2.47ChemAxon
pKa (Strongest Basic)9.45ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area63.32 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity45.12 m³·mol⁻¹ChemAxon
Polarizability17.13 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular LocationsNot Available
Organoleptic Properties
Flavour/OdourSource
OdorlessNot Available
SMPDB Pathways
Methionine metabolism and salvagePW002384 ThumbThumb?image type=greyscaleThumb?image type=simple
Phenylalanine metabolismPW002437 ThumbThumb?image type=greyscaleThumb?image type=simple
Tryptophan metabolismPW002442 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Phenylalanine metabolismec00360 Map00360
Tryptophan metabolismec00380 Map00380
SMPDB ReactionsNot Available
KEGG ReactionsNot Available
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-006x-9600000000-df38fcb743d8f44fb876JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00xr-1900000000-0716c626d7af27ede0c6JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-2900000000-c28830f82e77d9fd325cJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9100000000-59ef5064d5616752bdcbJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0900000000-73d3e9e338ef63c2f358JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03k9-3900000000-09edb34ae30afc47be75JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00di-9400000000-bc289705a957b79378baJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
References
References:
  • Scheer, M., Grote, A., Chang, A., Schomburg, I., Munaretto, C., Rother, M., Sohngen, C., Stelzer, M., Thiele, J., Schomburg, D. (2011). "BRENDA, the enzyme information system in 2011." Nucleic Acids Res 39:D670-D676.21062828
  • Yow, G. Y., Uo, T., Yoshimura, T., Esaki, N. (2004). "D-amino acid N-acetyltransferase of Saccharomyces cerevisiae: a close homologue of histone acetyltransferase Hpa2p acting exclusively on free D-amino acids." Arch Microbiol 182:396-403.15375647
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID16998
HMDB IDHMDB00159
Pubchem Compound ID6140
Kegg IDC02265
ChemSpider ID64639
FOODB IDNot Available
WikipediaPhenylalanine
BioCyc IDPHE

Enzymes

General function:
Involved in N-acetyltransferase activity
Specific function:
N-acetyltransferase whose physiological acetyl acceptor substrate is still unknown. In vitro, histone acetylation is very weak
Gene Name:
HPA3
Uniprot ID:
P39979
Molecular weight:
20698.5
Reactions
acetyl-CoA + a D-amino acid → CoA + an N-acetyl-D-amino acid