Record Information
Version3.6
Creation Date2010-05-13 16:18:18 UTC
Update Date2013-02-09 00:30:39 UTC
HMDB IDHMDB13609
Secondary Accession NumbersNone
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
  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 FormulaC11H12N2O2
Average Molecular Weight204.2252
Monoisotopic Molecular Weight204.089877638
IUPAC Name(2R)-2-amino-3-(1H-indol-3-yl)propanoic acid
Traditional IUPAC 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
KingdomOrganic Compounds
Super ClassAmino Acids, Peptides, and Analogues
ClassAmino Acids and Derivatives
Sub ClassAlpha 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 ParentAlpha Amino Acids and Derivatives
Ontology
StatusExpected and 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 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 area79.11ChemAxon
rotatable bond count3ChemAxon
refractivity56.2ChemAxon
polarizability21.21ChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular LocationsNot Available
Biofluid Locations
  • Blood
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReference
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableCommentNormal
  • Not Applicable
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 LinkHMDB13609
Metagene LinkHMDB13609
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

Gene Name:
IDO1
Uniprot ID:
P14902
Reactions
D-Tryptophan + Oxygen unknown N'-Formylkynureninedetails