Identification

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Name
D-Tryptophan
Accession Number
DB03225  (EXPT01290)
Type
Small Molecule
Groups
Experimental
Description

Tryptophan 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
  • (2R)-2-amino-3-(1H-indol-3-yl)propanoic acid
  • (R)-tryptophan
  • DTR
External IDs
NSC-97942
Categories
Not Available
UNII
7NS97N9H1G
CAS number
153-94-6
Weight
Average: 204.2252
Monoisotopic: 204.089877638
Chemical Formula
C11H12N2O2
InChI Key
QIVBCDIJIAJPQS-SECBINFHSA-N
InChI
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
IUPAC Name
(2R)-2-amino-3-(1H-indol-3-yl)propanoic acid
SMILES
N[C@H](CC1=CNC2=CC=CC=C12)C(O)=O

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UD-amino-acid oxidaseNot AvailableHumans
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Not Available
Food Interactions
Not Available

References

Synthesis Reference

Hiroaki Yamamoto, Kazuya Mitsuhashi, Akinobu Matsuyama, Fusao Tomita, "Method for producing D-tryptophan." U.S. Patent US5916781, issued July, 1985.

US5916781
General References
Not Available
External Links
Human Metabolome Database
HMDB0013609
KEGG Compound
C00525
PubChem Compound
9060
PubChem Substance
46508031
ChemSpider
8707
BindingDB
50043799
ChEBI
16296
ChEMBL
CHEMBL292303
HET
DTR
PDB Entries
1czq / 1ddo / 1dfy / 1dfz / 1dg0 / 1nxn / 1qfb / 1soc / 1tkf / 1xxz
show 59 more

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)282-85 dec °CPhysProp
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 FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.984
Blood Brain Barrier+0.951
Caco-2 permeable-0.5943
P-glycoprotein substrateNon-substrate0.5988
P-glycoprotein inhibitor INon-inhibitor0.9951
P-glycoprotein inhibitor IINon-inhibitor0.9779
Renal organic cation transporterNon-inhibitor0.8805
CYP450 2C9 substrateNon-substrate0.8463
CYP450 2D6 substrateNon-substrate0.7897
CYP450 3A4 substrateNon-substrate0.7841
CYP450 1A2 substrateNon-inhibitor0.9531
CYP450 2C9 inhibitorNon-inhibitor0.9481
CYP450 2D6 inhibitorNon-inhibitor0.9307
CYP450 2C19 inhibitorNon-inhibitor0.9644
CYP450 3A4 inhibitorNon-inhibitor0.9432
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9542
Ames testNon AMES toxic0.9284
CarcinogenicityNon-carcinogens0.931
BiodegradationNot ready biodegradable0.8348
Rat acute toxicity1.1785 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9864
hERG inhibition (predictor II)Non-inhibitor0.9402
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
MS/MS Spectrum - , negativeLC-MS/MSsplash10-0gi0-4940000000-00a5a8140b79080185e6
MS/MS Spectrum - , negativeLC-MS/MSsplash10-0gi0-3940000000-321dc703abd716322faa
MS/MS Spectrum - , positiveLC-MS/MSsplash10-000j-0900000000-75b4d705a8e2930848e3
MS/MS Spectrum - , positiveLC-MS/MSsplash10-000j-0900000000-5ce443f4be2efcf027ea

Taxonomy

Description
This 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.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Indoles and derivatives
Sub Class
Indolyl carboxylic acids and derivatives
Direct Parent
Indolyl carboxylic acids and derivatives
Alternative Parents
D-alpha-amino acids / 3-alkylindoles / Aralkylamines / Substituted pyrroles / Benzenoids / Heteroaromatic compounds / Amino acids / Monocarboxylic acids and derivatives / Carboxylic acids / Azacyclic compounds
show 5 more
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
show 19 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
D-alpha-amino acid, tryptophan (CHEBI:16296) / Other amino acids (C00525)

Targets

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Receptor binding
Specific Function
Regulates the level of the neuromodulator D-serine in the brain. Has high activity towards D-DOPA and contributes to dopamine synthesis. Could act as a detoxifying agent which removes D-amino acids...
Gene Name
DAO
Uniprot ID
P14920
Uniprot Name
D-amino-acid oxidase
Molecular Weight
39473.75 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
  3. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235]

Transporters

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Transporter activity
Specific Function
Sodium-independent transporter that mediates the update of aromatic acid. Can function as a net efflux pathway for aromatic amino acids in the basosolateral epithelial cells (By similarity).
Gene Name
SLC16A10
Uniprot ID
Q8TF71
Uniprot Name
Monocarboxylate transporter 10
Molecular Weight
55492.07 Da
References
  1. Kim DK, Kanai Y, Chairoungdua A, Matsuo H, Cha SH, Endou H: Expression cloning of a Na+-independent aromatic amino acid transporter with structural similarity to H+/monocarboxylate transporters. J Biol Chem. 2001 May 18;276(20):17221-8. Epub 2001 Feb 20. [PubMed:11278508]

Drug created on June 13, 2005 07:24 / Updated on December 02, 2019 06:28