Identification
- Generic Name
- D-Tryptophan
- DrugBank Accession Number
- DB03225
- Background
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.
- Type
- Small Molecule
- Groups
- Experimental
- Structure
Structure for D-Tryptophan (DB03225)
- Weight
- Average: 204.2252
Monoisotopic: 204.089877638 - Chemical Formula
- C11H12N2O2
- Synonyms
- (2R)-2-amino-3-(1H-indol-3-yl)propanoic acid
- (R)-tryptophan
- DTR
- External IDs
- NSC-97942
Pharmacology
- Indication
Not Available
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Not Available
- Mechanism of action
Target Actions Organism UD-amino-acid oxidase Not Available Humans - 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
- Adverse Effects
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates.Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
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
Categories
- Drug Categories
- Not Available
- Chemical TaxonomyProvided by Classyfire
- 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
- 3-alkylindole / Alpha-amino acid / Alpha-amino acid or derivatives / Amine / Amino acid / Amino acid or derivatives / Aralkylamine / Aromatic heteropolycyclic compound / Azacycle / Benzenoid show 19 more
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- D-alpha-amino acid, tryptophan (CHEBI:16296) / Other amino acids (C00525)
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- 7NS97N9H1G
- CAS number
- 153-94-6
- 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
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
- ZINC
- ZINC000000083317
- PDBe Ligand
- DTR
- PDB Entries
- 1czq / 1ddo / 1dfy / 1dfz / 1dg0 / 1nxn / 1qfb / 1soc / 1tkf / 1xxz … show 95 more
Clinical Trials
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
- Not Available
- Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 282-85 dec °C PhysProp - Predicted Properties
Property Value Source Water Solubility 1.36 mg/mL ALOGPS logP -1.1 ALOGPS logP -1.1 Chemaxon logS -2.2 ALOGPS pKa (Strongest Acidic) 2.54 Chemaxon pKa (Strongest Basic) 9.4 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 3 Chemaxon Hydrogen Donor Count 3 Chemaxon Polar Surface Area 79.11 Å2 Chemaxon Rotatable Bond Count 3 Chemaxon Refractivity 56.2 m3·mol-1 Chemaxon Polarizability 21.17 Å3 Chemaxon Number of Rings 2 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.984 Blood Brain Barrier + 0.951 Caco-2 permeable - 0.5943 P-glycoprotein substrate Non-substrate 0.5988 P-glycoprotein inhibitor I Non-inhibitor 0.9951 P-glycoprotein inhibitor II Non-inhibitor 0.9779 Renal organic cation transporter Non-inhibitor 0.8805 CYP450 2C9 substrate Non-substrate 0.8463 CYP450 2D6 substrate Non-substrate 0.7897 CYP450 3A4 substrate Non-substrate 0.7841 CYP450 1A2 substrate Non-inhibitor 0.9531 CYP450 2C9 inhibitor Non-inhibitor 0.9481 CYP450 2D6 inhibitor Non-inhibitor 0.9307 CYP450 2C19 inhibitor Non-inhibitor 0.9644 CYP450 3A4 inhibitor Non-inhibitor 0.9432 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9542 Ames test Non AMES toxic 0.9284 Carcinogenicity Non-carcinogens 0.931 Biodegradation Not ready biodegradable 0.8348 Rat acute toxicity 1.1785 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9864 hERG inhibition (predictor II) Non-inhibitor 0.9402
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS Not Available Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available MS/MS Spectrum - , negative LC-MS/MS splash10-0gi0-4940000000-00a5a8140b79080185e6 MS/MS Spectrum - , negative LC-MS/MS splash10-0gi0-3940000000-321dc703abd716322faa MS/MS Spectrum - , positive LC-MS/MS splash10-000j-0900000000-75b4d705a8e2930848e3 MS/MS Spectrum - , positive LC-MS/MS splash10-000j-0900000000-5ce443f4be2efcf027ea
Targets
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- 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
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
- 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. [Article]
- 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. [Article]
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
- 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. [Article]
Drug created at June 13, 2005 13:24 / Updated at June 12, 2020 16:52