L-α-methyldopa   Click here for help

GtoPdb Ligand ID: 5217

Synonyms: Aldomet® | Aldoril® | Dopamet® | L-α-Methyl-3,4-dihydroxyphenylalanine
Approved drug
L-α-methyldopa is an approved drug (FDA (1962))
Compound class: Synthetic organic
Comment: L-α-methyldopa is metabolised to α-methylnorepinephrine in the brain, the metabolite being a selective agonist of α2 adrenoceptors. Clinical L-α-methyldopa use has largely been replaced by safer alternatives.
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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Click here for structure editor
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 4
Rotatable bonds 3
Topological polar surface area 103.78
Molecular weight 211.08
XLogP -1.92
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 OC(=O)C(Cc1ccc(c(c1)O)O)(N)C
Isomeric SMILES OC(=O)[C@](Cc1ccc(c(c1)O)O)(N)C
InChI InChI=1S/C10H13NO4/c1-10(11,9(14)15)5-6-2-3-7(12)8(13)4-6/h2-4,12-13H,5,11H2,1H3,(H,14,15)/t10-/m0/s1
InChI Key CJCSPKMFHVPWAR-JTQLQIEISA-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 Synthetic organic
Approved drug? Yes (FDA (1962))
WHO Essential Medicine WHO Essential Medicines List (EML) (23rd List, 2023). Access PDF version.
Click to view more information about the WHO Model Lists of Essential Medicines.
IUPAC Name Click here for help
(2S)-2-amino-3-(3,4-dihydroxyphenyl)-2-methylpropanoic acid
International Nonproprietary Names Click here for help
INN number INN
1110 methyldopa
Synonyms Click here for help
Aldomet® | Aldoril® | Dopamet® | L-α-Methyl-3,4-dihydroxyphenylalanine
Database Links Click here for help
CAS Registry No. 555-30-6
ChEBI CHEBI:61058
ChEMBL Ligand CHEMBL459
DrugBank Ligand DB00968
DrugCentral Ligand 1762
GtoPdb PubChem SID 178101902
PubChem CID 38853
Search Google for chemical match using the InChIKey CJCSPKMFHVPWAR-JTQLQIEISA-N
Search Google for chemicals with the same backbone CJCSPKMFHVPWAR
Search PubMed clinical trials methyldopa
Search PubMed titles methyldopa
Search PubMed titles/abstracts methyldopa
UniChem Compound Search for chemical match using the InChIKey CJCSPKMFHVPWAR-JTQLQIEISA-N
UniChem Connectivity Search for chemical match using the InChIKey CJCSPKMFHVPWAR-JTQLQIEISA-N
Wikipedia Methyldopa