Hmdb loader
You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version5.0
StatusDetected and Quantified
Creation Date2010-05-13 16:18:18 UTC
Update Date2021-10-13 05:40:42 UTC
HMDB IDHMDB0013609
Secondary Accession Numbers
  • HMDB13609
Metabolite Identification
Common NameD-Tryptophan
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. D-Tryptophan is found, on average, in the highest concentration within milk (cow) and beer. This could make D-tryptophan a potential biomarker for the consumption of these foods. D-Tryptophan is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review a significant number of articles have been published on D-Tryptophan.
Structure
Data?1582753136
Synonyms
ValueSource
(2R)-2-Amino-3-(1H-indol-3-yl)propanoic acidChEBI
(R)-TryptophanChEBI
DTRChEBI
(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
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
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
Ontology
Physiological effect

Adverse health effect

Disposition

Biological location

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point282 - 85 °CNot Available
Boiling Point447.91 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility2848 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP0.704 (est)The Good Scents Company Information System
Experimental Spectral PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility1.36 g/LALOGPS
logP10(-1.1) g/LALOGPS
logP10(-1.1) g/LChemAxon
logS10(-2.2) g/LALOGPS
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Spectral Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+146.83831661259
DarkChem[M-H]-146.57331661259

Predicted Kovats Retention Indices

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
D-Tryptophan,1TMS,#1C[Si](C)(C)OC(=O)[C@H](N)CC1=C[NH]C2=CC=CC=C122197.3Semi standard non polarhttps://arxiv.org/abs/1905.12712
D-Tryptophan,1TMS,#2C[Si](C)(C)N[C@H](CC1=C[NH]C2=CC=CC=C12)C(=O)O2255.2Semi standard non polarhttps://arxiv.org/abs/1905.12712
D-Tryptophan,1TMS,#3C[Si](C)(C)N1C=C(C[C@@H](N)C(=O)O)C2=CC=CC=C212272.6Semi standard non polarhttps://arxiv.org/abs/1905.12712
D-Tryptophan,1TBDMS,#1CC(C)(C)[Si](C)(C)OC(=O)[C@H](N)CC1=C[NH]C2=CC=CC=C122475.2Semi standard non polarhttps://arxiv.org/abs/1905.12712
D-Tryptophan,1TBDMS,#2CC(C)(C)[Si](C)(C)N[C@H](CC1=C[NH]C2=CC=CC=C12)C(=O)O2522.1Semi standard non polarhttps://arxiv.org/abs/1905.12712
D-Tryptophan,1TBDMS,#3CC(C)(C)[Si](C)(C)N1C=C(C[C@@H](N)C(=O)O)C2=CC=CC=C212534.0Semi standard non polarhttps://arxiv.org/abs/1905.12712
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - D-Tryptophan GC-MS (Non-derivatized) - 70eV, Positivesplash10-0560-4900000000-fa932bc4cffed0ca66b72016-09-22Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - D-Tryptophan GC-MS (1 TMS) - 70eV, Positivesplash10-00gl-7490000000-c8150f8039963f4eb7f72017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - D-Tryptophan GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Feces
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot Available
Normal
      Not Available
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Not Specified
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
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 QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified1.13-34.27 umol/mmol creatinineChildren (1-13 years old)Not SpecifiedNormal details
UrineDetected and Quantified1.70-25.90 umol/mmol creatinineAdolescent (13-18 years old)Not SpecifiedNormal details
UrineDetected and Quantified2.036-12.90 umol/mmol creatinineAdult (>18 years old)Not SpecifiedNormal details
UrineDetected and Quantified1.58-35.63 umol/mmol creatinineInfant (0-1 year old)Not SpecifiedNormal details
UrineDetected and Quantified1.58-35.63 umol/mmol creatinineChildren (1-13 years old)Not SpecifiedNormal details
UrineDetected and Quantified1.13-34.27 umol/mmol creatinineChildren (1-13 years old)Not SpecifiedNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer
details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothBladder 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 IDDB03225
Phenol Explorer Compound IDNot Available
FooDB IDFDB029595
KNApSAcK IDC00052033
Chemspider ID8707
KEGG Compound IDC00525
BioCyc IDD-TRYPTOPHAN
BiGG IDNot Available
Wikipedia LinkTryptophan
METLIN IDNot Available
PubChem Compound9060
PDB IDNot Available
ChEBI ID16296
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1234281
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