Human Metabolome Database Version 3.5

Showing metabocard for D-Tryptophan (HMDB13609)

Record Information
Version 3.5
Creation Date 2010-05-13 10:18:18 -0600
Update Date 2013-02-08 17:30:39 -0700
HMDB ID HMDB13609
Secondary Accession Numbers None
Metabolite Identification
Common Name D-Tryptophan
Description Tryptophan (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
Download: MOL | SDF | PDB | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. (+)-tryptophan
  2. (2R)-2-amino-3-(1H-indol-3-yl)propanoate
  3. (2R)-2-amino-3-(1H-indol-3-yl)propanoic acid
  4. (R)-(+)-2-Amino-3-(3-indolyl)propionic acid
  5. (R)-2-Amino-3-(3-indolyl)propionic acid
  6. (R)-tryptophan
  7. D-(+)-Tryptophan
  8. D-alpha-Amino-3-indolepropionic acid
  9. D-Tryptophane
  10. D-Trytophane
  11. delta-(+)-Tryptophan
  12. delta-alpha-Amino-3-indolepropionic acid
  13. delta-Tryptophane
  14. delta-Trytophane
  15. DL-tryptophan
  16. DTR
  17. H-D-TRP-oh
  18. H-delta-TRP-oh
  19. Tryptophan
Chemical Formula C11H12N2O2
Average Molecular Weight 204.2252
Monoisotopic Molecular Weight 204.089877638
IUPAC Name (2R)-2-amino-3-(1H-indol-3-yl)propanoic acid
Traditional IUPAC Name D-tryptophan
CAS Registry Number 153-94-6
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 Key QIVBCDIJIAJPQS-SECBINFHSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Amino Acids, Peptides, and Analogues
Class Amino Acids and Derivatives
Sub Class Alpha Amino Acids and Derivatives
Other Descriptors
  • Aromatic Heteropolycyclic Compounds
  • Common amino acids(KEGG)
  • amino acid zwitterion(ChEBI)
Substituents
  • Carboxylic Acid
  • Indole
  • Indolyl Carboxylic Acid Derivative
  • Primary Aliphatic Amine (Alkylamine)
  • Pyrrole
  • Tryptamine
Direct Parent Alpha Amino Acids and Derivatives
Ontology
Status Expected and Not Quantified
Origin
  • Endogenous
Biofunction Not Available
Application Not Available
Cellular locations Not Available
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point 282 - 85 °C Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 1.36 g/L ALOGPS
LogP -1.10 ALOGPS
LogP -1.1 ChemAxon
LogS -2.18 ALOGPS
pKa (strongest acidic) 2.54 ChemAxon
pKa (strongest basic) 9.4 ChemAxon
Hydrogen Acceptor Count 3 ChemAxon
Hydrogen Donor Count 3 ChemAxon
Polar Surface Area 79.11 A2 ChemAxon
Rotatable Bond Count 3 ChemAxon
Refractivity 56.2 ChemAxon
Polarizability 21.21 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 0 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations Not Available
Biofluid Locations
  • Blood
Tissue Location Not Available
Pathways Not Available
Normal Concentrations
Biofluid Status Value Age Sex Condition Reference
Blood Expected but not Quantified
Not Applicable Not Available Not Available Comment Normal
  • Not Applicable
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
DrugBank Metabolite ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB029595
KNApSAcK ID Not Available
Chemspider ID 8707 Link_out
KEGG Compound ID C00525 Link_out
BioCyc ID D-TRYPTOPHAN Link_out
BiGG ID Not Available
Wikipedia Link Not Available
NuGOwiki Link HMDB13609 Link_out
Metagene Link HMDB13609 Link_out
METLIN ID Not Available
PubChem Compound 9060 Link_out
PDB ID DTR Link_out
ChEBI ID 16296 Link_out
References
Synthesis Reference Not 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 Link_out

Enzymes
Name: Indoleamine 2,3-dioxygenase 1
Reactions:
D-Tryptophan + Oxygen unknown N'-Formylkynurenine details
Gene Name: IDO1
Uniprot ID: P14902 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA