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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2010-05-13 16:18:18 UTC
Update Date2018-05-20 20:23:49 UTC
HMDB IDHMDB0013609
Secondary Accession Numbers
  • HMDB13609
Metabolite Identification
Common NameD-Tryptophan
DescriptionTryptophan (Trp or W) (sold for medical use as Tryptan) is one of the 20 standard amino acids. Its distinguishing structural characteristic is its indole functional group. The D-stereoisomer is occasionally found in naturally produced peptides (e.g. contryphan, the marine venom peptide).
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=C1C=CC=C2)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
Disposition

Biological location:

Source:

Role

Industrial application:

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 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
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0560-4900000000-fa932bc4cffed0ca66b7View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00gl-7490000000-c8150f8039963f4eb7f7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - , negativesplash10-0gi0-4940000000-00a5a8140b79080185e6View in MoNA
LC-MS/MSLC-MS/MS Spectrum - , 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, Positivesplash10-0a4i-0920000000-48b0cf647bfaeff82749View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-0900000000-ae69c675905bf421649dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-0900000000-0189d8e97d18427f2b04View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-3290000000-670b28bfa8011e4915e0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-9730000000-c2c5e2644b01d811fce0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00di-9600000000-06c476c7e459db7aa6b4View in MoNA
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Feces
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot Available
Normal
    details
    FecesDetected but not Quantified Adult (>18 years old)Both
    Normal
    details
    FecesDetected but not Quantified Adult (>18 years old)Not Specified
    Normal
    details
    FecesDetected and Quantified170 +/- 110 nmol/g wet fecesAdult (>18 years old)Both
    Normal
    details
    FecesDetected and Quantified20 +/- 20 nmol/g wet fecesAdult (>18 years old)Both
    Normal
    details
    FecesDetected but not Quantified Adult (>18 years old)Both
    Normal
    details
    Abnormal Concentrations
    BiospecimenStatusValueAgeSexConditionReferenceDetails
    FecesDetected but not Quantified Adult (>18 years old)Both
    Colorectal cancer
    details
    FecesDetected but not Quantified Adult (>18 years old)Both
    Colorectal cancer
    details
    Associated Disorders and Diseases
    Disease References
    Colorectal cancer
    1. Sinha R, Ahn J, Sampson JN, Shi J, Yu G, Xiong X, Hayes RB, Goedert JJ: Fecal Microbiota, Fecal Metabolome, and Colorectal Cancer Interrelations. PLoS One. 2016 Mar 25;11(3):e0152126. doi: 10.1371/journal.pone.0152126. eCollection 2016. [PubMed:27015276 ]
    2. Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
    Associated OMIM IDs
    DrugBank IDNot Available
    Phenol Explorer Compound IDNot Available
    FoodDB IDFDB029595
    KNApSAcK IDNot Available
    Chemspider ID8707
    KEGG Compound IDC00525
    BioCyc IDD-TRYPTOPHAN
    BiGG IDNot Available
    Wikipedia LinkNot Available
    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