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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 of the catecholamine dopamine neurotransmitters. It has been isolated as a naturally ocurring metabolite from Vicia faba (broad bean or fava) beans [1,3]. 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/)
Bioactivity Comments
Levodopa is a dopamine precursor and has no intrinsic target interactions that convey its therapeutic actions. L-DOPA is transported across the blood-brain barrier by the L-type amino acid transporter 1 (LAT1; SLC7A5) and it is decarboxylated to dopamine by the endogenous enzyme dopa decarboxylase (DDC).
Natural/Endogenous Targets
Target
GPR143
Enzymes Catalysing Reactions with this Compound as a Substrate or Product
Enzyme EC number Reaction Reference
L-Aromatic amino-acid decarboxylase 4.1.1.28 Levodopa -> dopamine + CO2
5-hydroxy-L-tryptophan -> 5-hydroxytryptamine + CO2
L-Tyrosine hydroxylase 1.14.16.2 L-tyrosine + O2 -> levodopa
Transporters Moving this Compound Across a Lipid Membrane
Transporter EC number Reaction Reference
Monocarboxylate transporter 10
Selectivity at GPCRs
Key to terms and symbols Click column headers to sort
Target Sp. Type Action Value Parameter Concentration range (M) Reference
GPR143 Ligand is endogenous in the given species Hs Agonist Agonist - - - 2
⤷ [2]
Ligand mentioned in the following text fields
Catecholamine turnover overview