methyltyrosine   Click here for help

GtoPdb Ligand ID: 5094

Synonyms: Demser® | DL-alpha-methyltyrosine | metyrosine
Approved drug
methyltyrosine is an approved drug (FDA (1979))
Compound class: Metabolite
Comment: The INN for this compound is racemetirosine, indicating that it is a racemic mix of its R and S enantiomers. We show the non-isomeric structure to represent this mixture. The website rxlist.com describes the approved drug, Demser, as (-)-α-methyl-L-tyrosine, but shows a non-stereo molecular structure. We have annotated both versions (racemic and S-enantiomer (L or α) with the same US FDA approval date, as the exact compostion of the approved drug is unclear.
2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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Hydrogen bond acceptors 3
Hydrogen bond donors 3
Rotatable bonds 3
Topological polar surface area 83.55
Molecular weight 195.09
XLogP -1.68
No. Lipinski's rules broken 0

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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Canonical SMILES Oc1ccc(cc1)CC(C(=O)O)(N)C
Isomeric SMILES Oc1ccc(cc1)CC(C(=O)O)(N)C
InChI InChI=1S/C10H13NO3/c1-10(11,9(13)14)6-7-2-4-8(12)5-3-7/h2-5,12H,6,11H2,1H3,(H,13,14)
InChI Key NHTGHBARYWONDQ-UHFFFAOYSA-N

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
Classification Click here for help
Compound class Metabolite
Approved drug? Yes (FDA (1979))
IUPAC Name Click here for help
2-amino-3-(4-hydroxyphenyl)-2-methylpropanoic acid
International Nonproprietary Names Click here for help
INN number INN
4292 racemetirosine
Synonyms Click here for help
Demser® | DL-alpha-methyltyrosine | metyrosine
Database Links Click here for help
CAS Registry No. 672-87-7
ChEMBL Ligand CHEMBL1330596
GtoPdb PubChem SID 178101787
PubChem CID 3125
Search Google for chemical match using the InChIKey NHTGHBARYWONDQ-UHFFFAOYSA-N
Search Google for chemicals with the same backbone NHTGHBARYWONDQ
Search PubMed clinical trials racemetirosine
Search PubMed titles racemetirosine
Search PubMed titles/abstracts racemetirosine
UniChem Compound Search for chemical match using the InChIKey NHTGHBARYWONDQ-UHFFFAOYSA-N
UniChem Connectivity Search for chemical match using the InChIKey NHTGHBARYWONDQ-UHFFFAOYSA-N
Wikipedia AMPT