ContaminantDB: Carbidopa

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-05-22 03:38:16 UTC

Update Date

2016-11-09 01:15:26 UTC

Accession Number

CHEM016604

Identification

Common Name

Carbidopa

Class

Small Molecule

Description

3-(3,4-Dihydroxyphenyl)propanoic acid in which the hydrogens alpha- to the carboxyl group are substituted by hydrazinyl and methyl groups (S-configuration). Carbidopa is a dopa decarboxylase inhibitor, so prevents conversion of levodopa to dopamine. It has no antiparkinson activity by itself, but is used (commonly as its hydrate) in the management of Parkinson's disease to reduce peripheral adverse effects of levodopa.

Contaminant Sources

HMDB Contaminants - Urine
STOFF IDENT Compounds
ToxCast & Tox21 Chemicals

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(-)-L-alpha-Hydrazino-3,4-dihydroxy-alpha-methylhydrocinnamic acid	ChEBI
(AlphaS)-alpha-hydrazino-3,4-dihydroxy-alpha-methylbenzenepropanoic acid	ChEBI
(S)-(-)-Carbidopa	ChEBI
(S)-Carbidopa	ChEBI
Carbidopum	ChEBI
L-3-(3,4-Dihydroxyphenyl)-2-methyl-2-hydrazinopropionic acid	ChEBI
L-alpha-Methyldopahydrazine	ChEBI
(-)-L-a-Hydrazino-3,4-dihydroxy-a-methylhydrocinnamate	Generator
(-)-L-a-Hydrazino-3,4-dihydroxy-a-methylhydrocinnamic acid	Generator
(-)-L-alpha-Hydrazino-3,4-dihydroxy-alpha-methylhydrocinnamate	Generator
(-)-L-Α-hydrazino-3,4-dihydroxy-α-methylhydrocinnamate	Generator
(-)-L-Α-hydrazino-3,4-dihydroxy-α-methylhydrocinnamic acid	Generator
(AlphaS)-a-hydrazino-3,4-dihydroxy-a-methylbenzenepropanoate	Generator
(AlphaS)-a-hydrazino-3,4-dihydroxy-a-methylbenzenepropanoic acid	Generator
(AlphaS)-alpha-hydrazino-3,4-dihydroxy-alpha-methylbenzenepropanoate	Generator
(AlphaS)-α-hydrazino-3,4-dihydroxy-α-methylbenzenepropanoate	Generator
(AlphaS)-α-hydrazino-3,4-dihydroxy-α-methylbenzenepropanoic acid	Generator
L-3-(3,4-Dihydroxyphenyl)-2-methyl-2-hydrazinopropionate	Generator
L-a-Methyldopahydrazine	Generator
L-Α-methyldopahydrazine	Generator
Lodosin	HMDB
Carbidopa, (R)-isomer	HMDB
Carbidopa, (S)-isomer	HMDB
Lodosyn	HMDB
Methyldopahydrazine	HMDB
Carbidopa	MeSH

Chemical Formula

C₁₀H₁₄N₂O₄

Average Molecular Mass

226.229 g/mol

Monoisotopic Mass

226.095 g/mol

CAS Registry Number

28860-95-9

IUPAC Name

(2S)-3-(3,4-dihydroxyphenyl)-2-hydrazinyl-2-methylpropanoic acid

Traditional Name

carbidopa

SMILES

C[C@@](CC1=CC(O)=C(O)C=C1)(NN)C(O)=O

InChI Identifier

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

Chemical Taxonomy

Description

belongs to the class of organic compounds known as phenylpropanoic acids. Phenylpropanoic acids are compounds with a structure containing a benzene ring conjugated to a propanoic acid.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Phenylpropanoic acids

Sub Class

Not Available

Direct Parent

Phenylpropanoic acids

Alternative Parents

Substituents

3-phenylpropanoic-acid
Alpha-amino acid or derivatives
Amphetamine or derivatives
Phenylpropane
Catechol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Benzenoid
Carboxylic acid derivative
Carboxylic acid
Alkylhydrazine
Monocarboxylic acid or derivatives
Organopnictogen compound
Hydrazine derivative
Organic oxygen compound
Organic nitrogen compound
Carbonyl group
Organonitrogen compound
Organooxygen compound
Organic oxide
Hydrocarbon derivative
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

monocarboxylic acid (CHEBI:39585 )
catechols (CHEBI:39585 )
hydrazines (CHEBI:39585 )

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	3.73 g/L	ALOGPS
logP	-0.16	ALOGPS
logP	-1.2	ChemAxon
logS	-1.8	ALOGPS
pKa (Strongest Acidic)	2.35	ChemAxon
pKa (Strongest Basic)	5.66	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	115.81 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	68.77 m³·mol⁻¹	ChemAxon
Polarizability	21.81 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0059-0980000000-f4aca4a185059362dadd	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-001i-0900000000-2f941cf7f7d49b1caefc	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0229-4900000000-fac3bc9d4b9d53b9abc7	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-1690000000-67f97c0c2d2205cf0066	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0ugi-3910000000-a2228e074afa13d25fff	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0f6t-2900000000-7db6ff075a07e0488f95	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-01si-0910000000-bda3c1f377846ab5976d	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0002-2900000000-7cf8eca30b1c42cf3cae	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00di-7900000000-8f2600bec3907643cf6e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-003r-0950000000-d304dfb158072a55b9db	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00e9-2900000000-eaccc21f6f8038d9897c	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-05fr-9400000000-94536afed8baecf9b7f6	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum

Toxicity Profile

Route of Exposure

Not Available

Mechanism of Toxicity

Not Available

Metabolism

Not Available

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

Not Available

Uses/Sources

Not Available

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Not Available

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

DB00190

HMDB ID

HMDB0014336

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Chemspider ID

ChEBI ID

PubChem Compound ID

Kegg Compound ID

Not Available

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

MSDS

Not Available

General References

1. Vickers S, Stuart EK, Hucker HB: Further studies on the metabolism of carbidopa, (minus)-L-alpha-hydrazino-3,4-dihydroxy-alpha-methylbenzenepropanoic acid monohydrate, in the human, Rhesus monkey, dog, and rat. J Med Chem. 1975 Feb;18(2):134-8.

2. Vickers S, Stuart EK, Bianchine JR, Hucker HB, Jaffe ME, Rhodes RE, Vandenheuvel WJ: Metabolism of carbidopa (1-(-)-alpha-hydrazino-3,4-dihydroxy-alpha-methylhydrocinnamic acid monohydrate), an aromatic amino acid decarboxylase inhibitor, in the rat, rhesus monkey, and man. Drug Metab Dispos. 1974 Jan-Feb;2(1):9-22.

Carbidopa (CHEM016604)

Structure for CHEM016604: Carbidopa