CHEBI:15765 - L-dopa

ChEBI IDCHEBI:15765
ChEBI NameL-dopa
Stars
ASCII NameL-dopa
DefinitionAn optically active form of dopa having L-configuration. Used to treat the stiffness, tremors, spasms, and poor muscle control of Parkinson's disease
Secondary ChEBI IDsCHEBI:1377, CHEBI:11693, CHEBI:13098, CHEBI:19825, CHEBI:41871, CHEBI:49933, CHEBI:75987
Last Modified8 March 2024
DownloadsMolfile
FormulaC9H11NO4
Net Charge0
Average Mass197.190
Monoisotopic Mass197.06881
SMILESN[C@@H](Cc1ccc(O)c(O)c1)C(=O)O
InChIInChI=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
InChIKeyWTDRDQBEARUVNC-LURJTMIESA-N
Wikipedia
Species of MetaboliteComponentSourceComments
Homo sapiens (ncbitaxon:9606) - DOI (10.1038/nbt.2488)
Mus musculus (ncbitaxon:10090) - PubMed (19425150) Source: BioModels - MODEL1507180067
Roles Classification
Chemical Roles:
Bronsted base  A molecular entity capable of accepting a hydron from a donor (Brønsted acid).
Bronsted acid  A molecular entity capable of donating a hydron to an acceptor (Brønsted base).
Bronsted base  A molecular entity capable of accepting a hydron from a donor (Brønsted acid).
Bronsted acid  A molecular entity capable of donating a hydron to an acceptor (Brønsted base).
Biological Roles:
neurotoxin  A poison that interferes with the functions of the nervous system.
mouse metabolite  Any mammalian metabolite produced during a metabolic reaction in a mouse (Mus musculus).
human metabolite  Any mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens).
hapten  Any substance capable of eliciting an immune response only when attached to a large carrier such as a protein. Examples include dinitrophenols; oligosaccharides; peptides; and heavy metals.
plant metabolite  Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
dopaminergic agent  A drug used for its effects on dopamine receptors, on the life cycle of dopamine, or on the survival of dopaminergic neurons.
allelochemical  A class of secondary metabolites developed by many plants to influence the behaviour, growth or survival of herbivores, and thus acting as a defence against herbivory.
human metabolite  Any mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens).
Applications:
prodrug  A compound that, on administration, must undergo chemical conversion by metabolic processes before becoming the pharmacologically active drug for which it is a prodrug.
antiparkinson drug  A drug used in the treatment of Parkinson's disease.
antidyskinesia agent  Any compound which can be used to treat or alleviate the symptoms of dyskinesia.
dopaminergic agent  A drug used for its effects on dopamine receptors, on the life cycle of dopamine, or on the survival of dopaminergic neurons.
ChEBI Ontology
Outgoing Relation(s)
L-dopa (CHEBI:15765) has role allelochemical (CHEBI:62215)
L-dopa (CHEBI:15765) has role antidyskinesia agent (CHEBI:66956)
L-dopa (CHEBI:15765) has role antiparkinson drug (CHEBI:48407)
L-dopa (CHEBI:15765) has role dopaminergic agent (CHEBI:48560)
L-dopa (CHEBI:15765) has role hapten (CHEBI:59174)
L-dopa (CHEBI:15765) has role human metabolite (CHEBI:77746)
L-dopa (CHEBI:15765) has role mouse metabolite (CHEBI:75771)
L-dopa (CHEBI:15765) has role neurotoxin (CHEBI:50910)
L-dopa (CHEBI:15765) has role plant growth retardant (CHEBI:35219)
L-dopa (CHEBI:15765) has role plant metabolite (CHEBI:76924)
L-dopa (CHEBI:15765) has role prodrug (CHEBI:50266)
L-dopa (CHEBI:15765) is a L-tyrosine derivative (CHEBI:27177)
L-dopa (CHEBI:15765) is a dopa (CHEBI:49168)
L-dopa (CHEBI:15765) is a non-proteinogenic L-α-amino acid (CHEBI:83822)
L-dopa (CHEBI:15765) is conjugate acid of L-dopa(1−) (CHEBI:67012)
L-dopa (CHEBI:15765) is enantiomer of D-dopa (CHEBI:49169)
L-dopa (CHEBI:15765) is tautomer of L-dopa zwitterion (CHEBI:57504)
Incoming Relation(s)
N-methyl-L-dopa (CHEBI:167646) has functional parent L-dopa (CHEBI:15765)
2-S-cysteinyl-DOPA (CHEBI:84296) has functional parent L-dopa (CHEBI:15765)
2,5-S,S'-dicysteinyldopa (CHEBI:84298) has functional parent L-dopa (CHEBI:15765)
3-O-methyldopa (CHEBI:82913) has functional parent L-dopa (CHEBI:15765)
3,4-dimethoxy-L-phenylalanine (CHEBI:229731) has functional parent L-dopa (CHEBI:15765)
4-O-methyl-L-dopa (CHEBI:193023) has functional parent L-dopa (CHEBI:15765)
6-fluoro-L-dopa (CHEBI:49163) has functional parent L-dopa (CHEBI:15765)
6-hydroxy-L-dopa (CHEBI:72753) has functional parent L-dopa (CHEBI:15765)
foslevodopa (CHEBI:192509) has functional parent L-dopa (CHEBI:15765)
L-dopa(1−) (CHEBI:67012) is conjugate base of L-dopa (CHEBI:15765)
D-dopa (CHEBI:49169) is enantiomer of L-dopa (CHEBI:15765)
L-dopa zwitterion (CHEBI:57504) is tautomer of L-dopa (CHEBI:15765)
IUPAC Names 
(2S)-2-amino-3-(3,4-dihydroxyphenyl)propanoic acid
L-dopa
INNs  Source
levodopaKEGG DRUG
levodopumChemIDplus
Synonyms  Source
(−)-3-(3,4-dihydroxyphenyl)-L-alanineChemIDplus
3,4-Dihydroxy-L-phenylalanineKEGG COMPOUND
3,4-DIHYDROXYPHENYLALANINEPDBeChem
3-Hydroxy-L-tyrosineKEGG COMPOUND
Dihydroxy-L-phenylalanineKEGG COMPOUND
(−)-dopaChemIDplus
Brand Name  Source
DoparKEGG DRUG
Manual XrefsDatabases
1567DrugCentral
C00001357KNApSAcK
C00355KEGG COMPOUND
D00059KEGG DRUG
DAH_LFOHPDBeChem
DB01235DrugBank
HMDB0000181HMDB
L-DIHYDROXY-PHENYLALANINEMetaCyc
L-DOPAWikipedia
LevodopaWikipedia
LSM-5481LINCS
Registry NumbersSources
Reaxys:2215169Reaxys
Gmelin:365846Gmelin
Beilstein:6060047Beilstein
CAS:59-92-7ChemIDplus
CAS:59-92-7NIST Chemistry WebBook
CAS:59-92-7KEGG COMPOUND
Citations