Identification
YMDB IDYMDB00805
NameD-Tyrosine
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionD-Tyrosine, also known as D-tyr, belongs to the class of organic compounds known as tyrosine and derivatives. Tyrosine and derivatives are compounds containing tyrosine or a derivative thereof resulting from reaction of tyrosine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. D-Tyrosine is a very strong basic compound (based on its pKa). D-Tyrosine exists in both E. coli (prokaryote) and yeast (eukaryote).
Structure
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Synonyms
  • (-)-a-Amino-p-hydroxyhydrocinnamate
  • (-)-a-Amino-p-hydroxyhydrocinnamic acid
  • (-)-alpha-Amino-p-hydroxyhydrocinnamate
  • (-)-alpha-Amino-p-hydroxyhydrocinnamic acid
  • (2R)-2-amino-3-(4-hydroxyphenyl)propanoic acid
  • (R)-2-Amino-3-(p-hydroxyphenyl)propionic acid
  • (R)-3-(p-Hydroxyphenyl)alanine
  • (S)-(-)-Tyrosine
  • (S)-2-Amino-3-(p-hydroxyphenyl)propionate
  • (S)-2-Amino-3-(p-hydroxyphenyl)propionic acid
  • (S)-3-(p-Hydroxyphenyl)alanine
  • (S)-a-amino-4-hydroxy-Benzenepropanoate
  • (S)-a-amino-4-hydroxy-Benzenepropanoic acid
  • (S)-a-Amino-4-hydroxybenzenepropanoate
  • (S)-a-Amino-4-hydroxybenzenepropanoic acid
  • (S)-alpha-amino-4-hydroxy-Benzenepropanoate
  • (S)-alpha-amino-4-hydroxy-Benzenepropanoic acid
  • (S)-alpha-Amino-4-hydroxybenzenepropanoate
  • (S)-alpha-Amino-4-hydroxybenzenepropanoic acid
  • (S)-Tyrosine
  • 3-(4-Hydroxyphenyl)-L-alanine
  • 4-hydroxy-L-Phenylalanine
  • Benzenepropanoate
  • Benzenepropanoic acid
  • D-Tyrosin
  • D-Tyrosine
  • L-p-Tyrosine
  • L-tyrosine
  • p-Tyrosine
  • Tyr
  • Tyrosine
  • D-Tyr
  • DTY
  • (2R)-2-Amino-3-(4-hydroxyphenyl)propanoate
  • (R)-2-Amino-3-(p-hydroxyphenyl)propionate
CAS number556-02-5
WeightAverage: 181.1885
Monoisotopic: 181.073893223
InChI KeyOUYCCCASQSFEME-MRVPVSSYSA-N
InChIInChI=1S/C9H11NO3/c10-8(9(12)13)5-6-1-3-7(11)4-2-6/h1-4,8,11H,5,10H2,(H,12,13)/t8-/m1/s1
IUPAC Name(2R)-2-amino-3-(4-hydroxyphenyl)propanoic acid
Traditional IUPAC Name(.+-.)-tyrosine
Chemical FormulaC9H11NO3
SMILESN[C@H](CC1=CC=C(O)C=C1)C(O)=O
Chemical Taxonomy
Description belongs to the class of organic compounds known as tyrosine and derivatives. Tyrosine and derivatives are compounds containing tyrosine or a derivative thereof resulting from reaction of tyrosine 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 ParentTyrosine and derivatives
Alternative Parents
Substituents
  • Tyrosine or derivatives
  • Phenylalanine or derivatives
  • 3-phenylpropanoic-acid
  • Alpha-amino acid
  • Amphetamine or derivatives
  • D-alpha-amino acid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Aralkylamine
  • Monocyclic benzene moiety
  • Benzenoid
  • Amino acid
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organic oxide
  • Organooxygen compound
  • Organonitrogen compound
  • Amine
  • Primary aliphatic amine
  • Organic nitrogen compound
  • Carbonyl group
  • Organopnictogen compound
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Primary amine
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Physical Properties
StateSolid
Charge0
Melting point343 °C
Experimental Properties
PropertyValueReference
Water Solubility0.479 mg/mL at 25 oC [SEIDELL,A (1941)]PhysProp
LogP-2.26 [HANSCH,C ET AL. (1995)]PhysProp
Predicted Properties
PropertyValueSource
Water Solubility7.67 g/LALOGPS
logP-2.4ALOGPS
logP-1.5ChemAxon
logS-1.4ALOGPS
pKa (Strongest Acidic)2ChemAxon
pKa (Strongest Basic)9.19ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area83.55 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity47.1 m³·mol⁻¹ChemAxon
Polarizability18.06 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular LocationsNot Available
Organoleptic PropertiesNot Available
SMPDB Pathways
Tyrosine metabolismPW002441 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Tyrosine metabolismec00350 Map00350
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, Positivesplash10-052r-4900000000-9be1412408207db5df4eJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01q0-0900000000-64b5df3e494e5df5c1beJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0900000000-c38735d64e2a16bd0c68JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-6900000000-6696908ff67c37922f99JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0900000000-941af648c85b3f0f7c66JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01q9-1900000000-b7d3075f2496303aeb37JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05fr-9700000000-c242deae91617b5e8735JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H 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
  • Zenk, M. H., Schmitt, J. H. (1965). "[Purification and properties of acetyl-CoA: D-amino acid-alpha-N-acetyltransferase from yeast]." Biochem Z 342:54-65.5847960
  • Vaseghi, S., Baumeister, A., Rizzi, M., Reuss, M. (1999). "In vivo dynamics of the pentose phosphate pathway in Saccharomyces cerevisiae." Metab Eng 1:128-140.10935926
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID28479
HMDB IDHMDB00158
Pubchem Compound ID6057
Kegg IDC06420
ChemSpider ID64252
FOODB IDNot Available
WikipediaTyrosine
BioCyc IDTYR

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