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Identification
YMDB IDYMDB00998
NameD-Tryptophan
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionD-Tryptophan, also known as DTR, belongs to the class of organic compounds known as indolyl carboxylic acids and derivatives. Indolyl carboxylic acids and derivatives are compounds containing a carboxylic acid chain (of at least 2 carbon atoms) linked to an indole ring. D-Tryptophan exists in all living species, ranging from bacteria to plants to humans. Based on a literature review a significant number of articles have been published on D-Tryptophan.
Structure
Thumb
Synonyms
  • (+)-tryptophan
  • (2R)-2-amino-3-(1H-indol-3-yl)propanoate
  • (2R)-2-amino-3-(1H-indol-3-yl)propanoic acid
  • (R)-(+)-2-Amino-3-(3-indolyl)propionic acid
  • (R)-2-Amino-3-(3-indolyl)propionic acid
  • (r)-tryptophan
  • D-(+)-tryptophan
  • D-alpha-Amino-3-indolepropionic acid
  • D-Tryptophan
  • D-tryptophane
  • D-trytophane
  • delta-(+)-tryptophan
  • delta-alpha-Amino-3-indolepropionic acid
  • delta-tryptophane
  • delta-trytophane
  • DL-tryptophan
  • DTR
  • H-d-TRP-oh
  • H-delta-TRP-oh
  • Tryptophan
  • Tryptophan, D-
CAS number153-94-6
WeightAverage: 204.2252
Monoisotopic: 204.089877638
InChI KeyQIVBCDIJIAJPQS-SECBINFHSA-N
InChIInChI=1S/C11H12N2O2/c12-9(11(14)15)5-7-6-13-10-4-2-1-3-8(7)10/h1-4,6,9,13H,5,12H2,(H,14,15)/t9-/m1/s1
IUPAC Name(2R)-2-amino-3-(1H-indol-3-yl)propanoic acid
Traditional IUPAC NameD-tryptophan
Chemical FormulaC11H12N2O2
SMILESN[C@H](CC1=CNC2=CC=CC=C12)C(O)=O
Chemical Taxonomy
Description belongs to the class of organic compounds known as indolyl carboxylic acids and derivatives. Indolyl carboxylic acids and derivatives are compounds containing a carboxylic acid chain (of at least 2 carbon atoms) linked to an indole ring.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassIndoles and derivatives
Sub ClassIndolyl carboxylic acids and derivatives
Direct ParentIndolyl carboxylic acids and derivatives
Alternative Parents
Substituents
  • Indolyl carboxylic acid derivative
  • Alpha-amino acid
  • Alpha-amino acid or derivatives
  • D-alpha-amino acid
  • 3-alkylindole
  • Indole
  • Aralkylamine
  • Benzenoid
  • Substituted pyrrole
  • Heteroaromatic compound
  • Pyrrole
  • Amino acid or derivatives
  • Amino acid
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Azacycle
  • Amine
  • Primary aliphatic amine
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Organic nitrogen compound
  • Carbonyl group
  • Organonitrogen compound
  • Organooxygen compound
  • Primary amine
  • Organopnictogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Physical Properties
StateSolid
Charge0
Melting point230 °C
Experimental Properties
PropertyValueReference
Water Solubility13.4 mg/mL at 25 oC [YALKOWSKY,SH & DANNENFELSER,RM (1992)]PhysProp
LogP-1.06 [HANSCH,C ET AL. (1995)]PhysProp
Predicted Properties
PropertyValueSource
Water Solubility1.36 g/LALOGPS
logP-1.1ALOGPS
logP-1.1ChemAxon
logS-2.2ALOGPS
pKa (Strongest Acidic)2.54ChemAxon
pKa (Strongest Basic)9.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area79.11 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity56.2 m³·mol⁻¹ChemAxon
Polarizability21.17 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular LocationsNot Available
Organoleptic PropertiesNot Available
SMPDB PathwaysNot Available
KEGG PathwaysNot Available
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, Positivesplash10-0560-4900000000-fa932bc4cffed0ca66b7JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00gl-7490000000-c8150f8039963f4eb7f7JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableJSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - , negativesplash10-0gi0-4940000000-00a5a8140b79080185e6JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - , negativesplash10-0gi0-3940000000-321dc703abd716322faaJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - 75V, Negativesplash10-0uxr-1960000000-3944aa089c0be5dbd57aJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - 30V, Negativesplash10-014i-0900000000-94061fd1f6b08445cdf3JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-0gb9-0930000000-da94834297fcc5b3d3c5JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - 25V, Negativesplash10-0zfr-0890000000-0d359faeb8858c021febJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-014i-0900000000-e78172f4f27df232466eJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-0zfr-0790000000-b95264f9ab4278178457JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-0a4i-0900000000-e13b1ada6628c7f81fadJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - 50V, Negativesplash10-014i-0900000000-93406e2cdb79770abc7dJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0090000000-c73c9b49139319c80b18JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - 65V, Negativesplash10-0udi-0690000000-4bf908b56440e171f545JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - 50V, Negativesplash10-0udi-0190000000-dfe53dc7eb1d8480b67dJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - 95V, Negativesplash10-014i-1910000000-d9efdaa0c5d83afa0a30JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-0udi-0090000000-3f6a5d549dc480992733JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-014i-0900000000-d8162407bfd6d77329ddJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - 60V, Negativesplash10-0udi-0390000000-99187dba9accfe70a9d7JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - 80V, Negativesplash10-0gb9-1940000000-6731b16a7a3f99824a8fJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-014i-0900000000-71ce6030cb0ece21c187JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - 70V, Negativesplash10-0uxr-1980000000-f81e0966edca14970bcdJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0890000000-8d614cd4a32f54f5f42bJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - 55V, Negativesplash10-0udi-0290000000-f509dc2b1981bd74e940JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - 30V, Negativesplash10-0a4i-0900000000-ad4c64ffc9170a5bae1eJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - 45V, Negativesplash10-0udi-0190000000-4aff7b2f76290f449a84JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - 90V, Negativesplash10-014i-0920000000-a9d3f1ce81f54000d79cJSpectraViewer | MoNA
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
  • 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 ID16296
HMDB IDHMDB13609
Pubchem Compound ID9060
Kegg IDC00525
ChemSpider ID8707
FOODB IDFDB029595
WikipediaTryptophan
BioCyc IDD-TRYPTOPHAN

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