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:
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.
neurotoxin  A poison that interferes with the functions of the nervous system.
human metabolite  Any mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens).
mouse metabolite  Any mammalian metabolite produced during a metabolic reaction in a mouse (Mus musculus).
plant metabolite  Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
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.
dopaminergic agent  A drug used for its effects on dopamine receptors, on the life cycle of dopamine, or on the survival of dopaminergic neurons.
analgesic  An agent capable of relieving pain without the loss of consciousness or without producing anaesthesia. In addition, analgesic is a role played by a compound which is exhibited by a capability to cause a reduction of pain symptoms.
human metabolite  Any mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens).
Applications:
antidepressant  Antidepressants are mood-stimulating drugs used primarily in the treatment of affective disorders and related conditions.
anti-asthmatic agent  Any compound that has anti-asthmatic effects.
neuroprotective agent  Any compound that can be used for the treatment of neurodegenerative disorders.
antiparkinson drug  A drug used in the treatment of Parkinson's disease.
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.
dopaminergic agent  A drug used for its effects on dopamine receptors, on the life cycle of dopamine, or on the survival of dopaminergic neurons.
vasoconstrictor agent  Drug used to cause constriction of the blood vessels.
antipsychotic agent  Antipsychotic drugs are agents that control agitated psychotic behaviour, alleviate acute psychotic states, reduce psychotic symptoms, and exert a quieting effect.
antidyskinesia agent  Any compound which can be used to treat or alleviate the symptoms of dyskinesia.
ophthalmology drug  Any compound used for the treatment of eye conditions or eye diseases.
analgesic  An agent capable of relieving pain without the loss of consciousness or without producing anaesthesia. In addition, analgesic is a role played by a compound which is exhibited by a capability to cause a reduction of pain symptoms.
ChEBI Ontology
Outgoing Relation(s)
L-dopa (CHEBI:15765) has role allelochemical (CHEBI:62215)
L-dopa (CHEBI:15765) has role analgesic (CHEBI:35480)
L-dopa (CHEBI:15765) has role anti-asthmatic agent (CHEBI:65023)
L-dopa (CHEBI:15765) has role antidepressant (CHEBI:35469)
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 antipsychotic agent (CHEBI:35476)
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 neuroprotective agent (CHEBI:63726)
L-dopa (CHEBI:15765) has role neurotoxin (CHEBI:50910)
L-dopa (CHEBI:15765) has role ophthalmology drug (CHEBI:66981)
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) has role vasoconstrictor agent (CHEBI:50514)
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
Cvt-301ChEMBL
Dihydroxy-L-phenylalanineKEGG COMPOUND
Brand Names  Source
BrocadopaChEMBL
DoparKEGG DRUG
InbrijaChEMBL
Levodopa component of /carbidopa/entacapone orionChEMBL
Levodopa component of corbiltaChEMBL
Levodopa component of crexontChEMBL
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:59-92-7KEGG COMPOUND
CAS:59-92-7NIST Chemistry WebBook
Citations