carbidopa   Click here for help

GtoPdb Ligand ID: 5159

Synonyms: Duodopa® | Lodosyn® | MK 486 [4]
Approved drug PDB Ligand
carbidopa is an approved drug (FDA (1977))
Compound class: Synthetic organic
Comment: Carbidopa was originally approved by the FDA in combination with levodopa in 1975. It is an inhibitor of L-Aromatic amino-acid decarboxylase (a.k.a. L-Dopa decarboxylase) [1,4] that decreases the peripheral decarboxylation of levodopa to dopamine. The competitive or noncompetitive nature of carbidopa's interaction with L-Dopa decarboxylase is complex. Two published papers that discuss the kinetics of the inhibitor/enzyme interaction are [4] and [1], and from analysis of these it would appear that due to the slow dissociation of carbidopa from L-Dopa decarboxylase, once the enzyme/inhibitor complex has formed substrate is unable to displace the inhibitor. Carbidopa is described as a competitive inhibitor in these articles [2-3].
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Ligand Activity Visualisation Charts

These are box plot that provide a unique visualisation, summarising all the activity data for a ligand taken from ChEMBL and GtoPdb across multiple targets and species. Click on a plot to see the median, interquartile range, low and high data points. A value of zero indicates that no data are available. A separate chart is created for each target, and where possible the algorithm tries to merge ChEMBL and GtoPdb targets by matching them on name and UniProt accession, for each available species. However, please note that inconsistency in naming of targets may lead to data for the same target being reported across multiple charts.

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View interactive charts of activity data across species

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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 CDK toolkit. 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 4
Hydrogen bond donors 5
Rotatable bonds 4
Topological polar surface area 115.81
Molecular weight 226.1
XLogP 0.02
No. Lipinski's rules broken 0
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.

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Canonical SMILES NNC(C(=O)O)(Cc1ccc(c(c1)O)O)C
Isomeric SMILES NN[C@](C(=O)O)(Cc1ccc(c(c1)O)O)C
InChI InChI=1S/C10H14N2O4/c1-10(12-11,9(15)16)5-6-2-3-7(13)8(14)4-6/h2-4,12-14H,5,11H2,1H3,(H,15,16)/t10-/m0/s1
InChI Key TZFNLOMSOLWIDK-JTQLQIEISA-N
References
1. Borri-Voltattorni C, Minelli A, Borri P. (1977)
Interaction of L-alpha-methyl-alpha-hydrazino-3,4 dihydroxyphenylpropionic acid with dopa-decarboxylase from pig kidney.
FEBS Lett, 75 (1): 277-80. [PMID:852589]
2. Durso R, Evans JE, Josephs E, Szabo G, Evans B, Fernandez HH, Browne TR. (2000)
Variable absorption of carbidopa affects both peripheral and central levodopa metabolism.
J Clin Pharmacol, 40 (8): 854-60. [PMID:10934669]
3. Ho CS, Butt A, Semra YK, Swaminathan R. (1997)
Effect of carbidopa on the excretion of sodium, dopamine, and ouabain-like substance in the rat.
Hypertension, 30 (6): 1544-8. [PMID:9403580]
4. Waterhouse MJ, Chia YC, Lees GJ. (1979)
Inhibition of human and rat hepatic aminotransferase activity with L-3,4-dihydroxyphenylalanine by inhibitors of peripheral aromatic amino acid decarboxylase.
Mol Pharmacol, 15 (1): 108-14. [PMID:423884]