levodopa   Click here for help

GtoPdb Ligand ID: 3639

Synonyms: 3,4-dihydroxy-L-phenylalanine | Inbrija® (levodopa inhalation powder) | L-DOPA | Sinemet®
Approved drug PDB Ligand
levodopa is an approved drug (FDA (1993), EMA (2003))
Compound class: Metabolite
Comment: L-DOPA is the precursor to the neurotransmitters dopamine collectively known as catecholamines. Used in the treatment of Parkisons disease. Note a deuterated derivative D3 L-DOPA with enhanced properties is under development.
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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 4
Rotatable bonds 3
Topological polar surface area 103.78
Molecular weight 197.07
XLogP -2.03
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
Isomeric SMILES OC(=O)[C@H](Cc1ccc(c(c1)O)O)N
InChI InChI=1S/C9H11NO4/c10-6(9(13)14)3-5-1-2-7(11)8(12)4-5/h1-2,4,6,11-12H,3,10H2,(H,13,14)/t6-/m0/s1
InChI Key WTDRDQBEARUVNC-LURJTMIESA-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 (1993), EMA (2003))
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.
Prodrug foslevodopa
IUPAC Name Click here for help
(2S)-2-amino-3-(3,4-dihydroxyphenyl)propanoic acid
International Nonproprietary Names Click here for help
INN number INN
2651 levodopa
Synonyms Click here for help
3,4-dihydroxy-L-phenylalanine | Inbrija® (levodopa inhalation powder) | L-DOPA | Sinemet®
Database Links Click here for help
CAS Registry No. 59-92-7 (source: Scifinder)
ChEBI CHEBI:15765
ChEMBL Ligand CHEMBL1009
DrugBank Ligand DB01235
DrugCentral Ligand 1567
GtoPdb PubChem SID 178100545
PubChem CID 6047
RCSB PDB Ligand DAH
Search Google for chemical match using the InChIKey WTDRDQBEARUVNC-LURJTMIESA-N
Search Google for chemicals with the same backbone WTDRDQBEARUVNC
Search PubMed clinical trials levodopa
Search PubMed titles levodopa
Search PubMed titles/abstracts levodopa
UniChem Compound Search for chemical match using the InChIKey WTDRDQBEARUVNC-LURJTMIESA-N
UniChem Connectivity Search for chemical match using the InChIKey WTDRDQBEARUVNC-LURJTMIESA-N
Wikipedia L-DOPA