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Record Information
Version3.6
Creation Date2010-05-13 16:18:18 UTC
Update Date2017-08-16 08:31:23 UTC
HMDB IDHMDB0013609
Secondary Accession Numbers
  • HMDB13609
Metabolite Identification
Common NameD-Tryptophan
DescriptionTryptophan (IUPAC-IUBMB abbreviation: Trp or W; IUPAC abbreviation: L-Trp or D-Trp; sold for medical use as Tryptan) is one of the 20 standard amino acids, as well as an essential amino acid in the human diet. It is encoded in the standard genetic code as the codon UGG. the D-stereoisomer is occasionally found in naturally produced peptides (for example, the marine venom peptide contryphan). The distinguishing structural characteristic of tryptophan is that it contains an indole functional group. It is an essential amino acid as defined by its growth effects on rats.
Structure
Thumb
Synonyms
ValueSource
(2R)-2-amino-3-(1H-indol-3-yl)Propanoic acidChEBI
(R)-TryptophanChEBI
(2R)-2-amino-3-(1H-indol-3-yl)PropanoateGenerator
(+)-TryptophanHMDB
(R)-(+)-2-amino-3-(3-Indolyl)propionic acidHMDB
(R)-2-amino-3-(3-Indolyl)propionic acidHMDB
D-(+)-TryptophanHMDB
D-alpha-amino-3-Indolepropionic acidHMDB
D-TryptophaneHMDB
D-TrytophaneHMDB
delta-(+)-TryptophanHMDB
delta-alpha-amino-3-Indolepropionic acidHMDB
delta-TryptophaneHMDB
delta-TrytophaneHMDB
DL-TryptophanHMDB
DTRHMDB
H-D-TRP-OHHMDB
H-delta-TRP-OHHMDB
TryptophanHMDB
Chemical FormulaC11H12N2O2
Average Molecular Weight204.2252
Monoisotopic Molecular Weight204.089877638
IUPAC Name(2R)-2-amino-3-(1H-indol-3-yl)propanoic acid
Traditional NameD-tryptophan
CAS Registry Number153-94-6
SMILES
N[C@H](CC1=CNC2=CC=CC=C12)C(O)=O
InChI Identifier
InChI=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
InChI KeyQIVBCDIJIAJPQS-SECBINFHSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as indolyl carboxylic acids and derivatives. These 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
  • D-alpha-amino acid
  • Alpha-amino acid or derivatives
  • Alpha-amino acid
  • Indole
  • Aralkylamine
  • Amino fatty acid
  • Fatty acyl
  • Benzenoid
  • Substituted pyrrole
  • Heteroaromatic compound
  • Pyrrole
  • Azacycle
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Carbonyl group
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point282 - 85 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility1.36 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity56.2 m3·mol-1ChemAxon
Polarizability21.17 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MSNot Available
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-0gi0-4940000000-00a5a8140b79080185e6View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-0gi0-3940000000-321dc703abd716322faaView in MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-000j-0900000000-75b4d705a8e2930848e3View in MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-000j-0900000000-5ce443f4be2efcf027eaView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
Biological Properties
Cellular LocationsNot Available
Biofluid Locations
  • Blood
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot Available
Normal
    details
    Abnormal Concentrations
    Not Available
    Associated Disorders and Diseases
    Disease ReferencesNone
    Associated OMIM IDsNone
    DrugBank IDNot Available
    DrugBank Metabolite IDNot Available
    Phenol Explorer Compound IDNot Available
    Phenol Explorer Metabolite IDNot Available
    FoodDB IDFDB029595
    KNApSAcK IDNot Available
    Chemspider ID8707
    KEGG Compound IDC00525
    BioCyc IDD-TRYPTOPHAN
    BiGG IDNot Available
    Wikipedia LinkNot Available
    NuGOwiki LinkHMDB0013609
    METLIN IDNot Available
    PubChem Compound9060
    PDB IDDTR
    ChEBI ID16296
    References
    Synthesis ReferenceNot Available
    Material Safety Data Sheet (MSDS)Not Available
    General References
    1. BARENBOIM GM: [Brief-duration fluorescence of DLtryptophan in frozen solutions]. Biofizika. 1962;7:227-32. [PubMed:13864966 ]

    Enzymes

    General function:
    Involved in heme binding
    Specific function:
    Catalyzes the cleavage of the pyrrol ring of tryptophan and incorporates both atoms of a molecule of oxygen.
    Gene Name:
    IDO1
    Uniprot ID:
    P14902
    Molecular weight:
    45325.89
    Reactions
    D-Tryptophan + Oxygen → N'-Formylkynureninedetails