Natural Product (NP) Details

General Information of the NP (ID: NP3140)
Name
Levodopa
Synonyms
levodopa; L-dopa; 59-92-7; 3-Hydroxy-L-tyrosine; 3,4-dihydroxy-L-phenylalanine; Dopar; Bendopa; Larodopa; Levopa; 3-(3,4-Dihydroxyphenyl)-L-alanine; Brocadopa; Cidandopa; Insulamina; Maipedopa; Dopaidan; Dopalina; Dopasol; Eldopal; Eldopar; Pardopa; Prodopa; Syndopa; 3,4-Dihydroxyphenylalanine; (-)-Dopa; Dihydroxy-L-phenylalanine; Helfo-Dopa; Dopaflex; Deadopa; Dopal-fher; Doparkine; Dopaston; Dopastral; Eldopatec; Eurodopa; Doparl; Doprin; Veldopa; (2S)-2-amino-3-(3,4-dihydroxyphenyl)propanoic acid; L-3,4-Dihydroxyphenylalanine; Levedopa; L-o-Hydroxytyrosine; Dopa; Levodopum; Ledopa; (-)-3-(3,4-Dihydroxyphenyl)-L-alanine; L-Tyrosine, 3-hydroxy-; 3,4-Dihydroxyphenyl-L-alanine; Dopaston SE; beta-(3,4-Dihydroxyphenyl)-L-alanine; L-(o-Dihydroxyphenyl)alanine; L-(-)-Dopa; L-3-Hydroxytyrosine; L-beta-(3,4-Dihydroxyphenyl)alanine; Weldopa; Parda; L-Dihydroxyphenylalanine; L-3-(3,4-Dihydroxyphenyl)alanine; C9H11NO4; Ro 4-6316; beta-(3,4-Dihydroxyphenyl)alanine; alanine, 3-(3,4-dihydroxyphenyl)-, L-; (S)-2-amino-3-(3,4-dihydroxyphenyl)propanoic acid; Levodopa free base; MFCD00002598; component of Sinemet; Dopar (TN); CHEBI:15765; beta-(3,4-Dihydroxyphenyl)-alpha-L-alanine; L-beta-(3,4-Dihydroxyphenyl)-alpha-alanine; UNII-46627O600J; Alanine, 3-(3,4-dihydroxyphenyl)-, (-)-; L(-)-Dopa; (-)-(3,4-Dihydroxyphenyl)alanine; dihydroxyphenylalanine; L-3,4-Dihydrophenylalanine; L-.beta.-(3,4-Dihydroxyphenyl)alanine; CHEMBL1009; .beta.-(3,4-Dihydroxyphenyl)-L-alanine; 59-92-7 (free base); L-(3,4-Dihydroxyphenyl)alanine; CVT-301; NSC118381; .beta.-(3,4-Dihydroxyphenyl)alanine; NSC-118381; CAS-59-92-7; NCGC00016270-04; Biodopa; Cerepap; Laradopa; Sobiodopa; L-(3,4-Dihydroxyphenyl)-.alpha.-alanine; 46627O600J; Helfo DOPA; beta-(3,4-Dihydroxyphenyl)-alpha-alanine; Tyrosine, 3-hydroxy-; Atamet; Levodopum [INN-Latin]; BDBM50130192; L-O-Dihydroxyphenylalanine; L Dopa; 3-(3,4-Dihydroxyphenyl)-L-alanine, 99%; CCRIS 3766; HSDB 3348; WLN: QVYZ1R CQ DQ; 3,4-Dihydroxyphenylalanine (VAN); SR-01000075384; 587-45-1; EINECS 200-445-2; NSC 118381; Dopastone; Dopicar; Inbrija; Prolopa; (2S)-2-amino-3-(3,4-dihydroxyphenyl)propanoate; Prestwick_185; Levodopa (Sinemet); L-DOPA; Levodopa; Madopa (Salt/Mix); Levodopa [USAN:USP:INN:BAN:JAN]; Spectrum_000454; Carbidopa EP Impurity A; Prestwick0_000017; Prestwick1_000017; Prestwick2_000017; Prestwick3_000017; Spectrum2_000496; Spectrum4_000539; Spectrum5_001899; Lopac-D-9628; Levodopa (JP15/USP); DSSTox_CID_3209; bmse000322; Epitope ID:150927; 3, 4-Dihydroxyphenylalanine; Alanine,4-dihydroxyphenyl)-; DSSTox_RID_76926; DSSTox_GSID_23209; Lopac0_000454; SCHEMBL22655; BSPBio_000053; BSPBio_002354; KBioGR_001177; KBioSS_000934; L-4-5-Dihydroxyphenylalanine; MLS000028514; BIDD:GT0158; DivK1c_000452; SPECTRUM2300205; Levodopa (JP17/USP/INN); SPBio_000391; SPBio_001974; BPBio1_000059; GTPL3639; b-(3,4-Dihydroxyphenyl)alanine; DTXSID9023209; WLN: QVYZ1R CQ DQ -L; 3, 4-Dihydroxy-L-phenylalanine; BDBM60928; HMS501G14; KBio1_000452; KBio2_000934; KBio2_003502; KBio2_006070; Alanine,4-dihydroxyphenyl)-, L-; L-(3, 4-Dihydroxyphenyl)alanine; NINDS_000452; 3-Ethoxy-4-fluorophenylboronicacid; HMS1568C15; HMS1922J14; HMS2090O08; HMS2093N04; HMS2095C15; HMS2230B04; HMS3261K10; HMS3712C15; Pharmakon1600-02300205; ZINC895199; H-Phe{3,4-(OH)2}-OH; HY-N0304; Levodopa;3,4-Dihydroxyphenylalanine; b-(3,4-Dihydroxyphenyl)-L-alanine; Inbrija (levodopa inhalation powder); Tox21_110338; Tox21_500454; ANW-33396; CCG-39571; KM0355; L-3-(3,4-dihydroxy-phenyl)alanine; L-3-(3,4-dihydroxyphenyl)-Alanine; NSC759573; PDSP1_001541; PDSP2_001525; s1726; SBB017533; Alanine, 3-(3,4-dihydroxyphenyl)-; Alanine,4-dihydroxyphenyl)-, (-)-; AKOS010396267; b-(3,4-Dihydroxyphenyl)-a-L-alanine; L-b-(3,4-Dihydroxyphenyl)-a-alanine; .beta.-(3, 4-Dihydroxyphenyl)alanine; AC-8432; AM82124; CS-1945; DB01235; LP00454; MCULE-4743781842; NSC-759573; SDCCGMLS-0066924.P001; SDCCGSBI-0050439.P004; VA11170; IDI1_000452; NCGC00015384-01; NCGC00016270-01; NCGC00016270-06; NCGC00016270-07; NCGC00016270-09; NCGC00016270-10; NCGC00016270-22; NCGC00093869-04; NCGC00261139-01; AK187821; AS-13287; BP-12850; H813; SMR000058312; ST086623; SBI-0050439.P003; AB0013279; L-(3, 4-Dihydroxyphenyl)-.alpha.-alanine; D0600; D9628; EU-0100454; N1648; 59L927; Alanine, 3-(3, 4-dihydroxyphenyl)-, (-)-; C00355; D 9628; D00059; J10404; V-1512; 13173-EP2269989A1; 13173-EP2277876A1; 13173-EP2277882A1; 13173-EP2281559A1; 13173-EP2281815A1; 13173-EP2292614A1; 13173-EP2295412A1; 13173-EP2295413A1; 13173-EP2295439A1; 13173-EP2298731A1; 13173-EP2301933A1; 13173-EP2301934A1; 13173-EP2305633A1; 13173-EP2305640A2; 13173-EP2308867A2; 13173-EP2308870A2; 13173-EP2311827A1; 13173-EP2311837A1; 13173-EP2314571A2; 13173-EP2316470A2; 13173-EP2316834A1; 21660-EP2272832A1; 21660-EP2275420A1; 21660-EP2281559A1; 21660-EP2301934A1; 21660-EP2314571A2; 21920-EP2295410A1; 21920-EP2301939A1; 21920-EP2314571A2; 3,4-Dihydroxy-L-phenylalanine, >=98% (TLC); AB00052418-06; AB00052418-07; AB00052418_08; AB00052418_09; Q300989; Q-201294; SR-01000075384-1; SR-01000075384-4; SR-01000075384-6; SR-01000075384-7; (S)-2-Amino-3-(3,4-dihydroxy-phenyl)-propionic acid; F0347-4695; Levodopa, British Pharmacopoeia (BP) Reference Standard; Levodopa, European Pharmacopoeia (EP) Reference Standard; Z1762772338; (2S)-2-amino-3-(3,4-dihydroxyphenyl)propanoic acidL-dopa; UNII-QI9C343R60 component WTDRDQBEARUVNC-LURJTMIESA-N; 1E83F927-C221-46AA-B90A-81B33C5F3868; 3,4-Dihydroxy-L-phenylalanine, Vetec(TM) reagent grade, 98%; Levodopa, United States Pharmacopeia (USP) Reference Standard; 3,4-Dihydroxy-L-phenylalanine, certified reference material, TraceCERT(R); Levodopa, Pharmaceutical Secondary Standard; Certified Reference Material; 122769-74-8; L-Methyldopa ; (2S)-2-Amino-3-(3,4-dihydroxyphenyl)-2-methylpropanoic acid; 3-(3,4-Dihydroxyphenyl)-?-methyl-L-alanine; 3-Hydroxy-a-methyl-L-tyrosine
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Species Origin Mucuna pruriens ...     Click to Show/Hide
Mucuna pruriens
Kingdom: Viridiplantae
Phylum: Streptophyta
Class: Magnoliopsida
Order: Fabales
Family: Fabaceae
Genus: Mucuna
Species: Mucuna pruriens
Disease Parkinson's disease [ICD-11: 8A00] Approved [1]
Structure
Click to Download Mol
2D MOL

3D MOL

ADMET Property
Absporption
Caco-2 Permeability
 -5.932
 
MDCK Permeability
 -4.96
 
PAMPA
 +++
 
HIA
 - - -
 
Distribution
VDss
 0.297
 
PPB
 21.8%
 
BBB
 - - -
 
Metabolism
CYP1A2 inhibitor
 - - -
CYP1A2 substrate
 - - -
CYP2C19 inhibitor
 - - -
CYP2C19 substrate
 - - -
CYP2C9 inhibitor
 - - -
CYP2C9 substrate
 ++
CYP2D6 inhibitor
 - - -
CYP2D6 substrate
 +++
CYP3A4 inhibitor
 - - -
CYP3A4 substrate
 - - -
CYP2B6 inhibitor
 - - -
CYP2B6 substrate
 - - -
CYP2C8 inhibitor
 - - -
HLM Stability
 +
 
Excretion
CLplasma
 23.223
 
T1/2
 2.416
Toxicity
DILI
 - -
 
Rat Oral Acute Toxicity
 - -
 
FDAMDD
 - -
 
Respiratory
 - - -
 
Human Hepatotoxicity
 +
 
Ototoxicity
 -
 
Drug-induced Nephrotoxicity
 - -
 
Drug-induced Neurotoxicity
 - -
 
Hematotoxicity
 - - -
 
Genotoxicity
 ++
 
Tips: 1. For the classification endpoints, the prediction probability values are transformed into six symbols: 0-0.1 (- - -), 0.1-0.3 (- -), 0.3-0.5 (-), 0.5-0.7 (+), 0.7-0.9 (++), and 0.9-1.0 (+++). 2. Additionally, the corresponding relationships of the three labels are as follows: excellent; medium; poor.
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    Click to Show/Hide the Molecular Information and External Link(s) of This Natural Product
Formula
C9H11NO4
PubChem CID
6047
Canonical SMILES
C1=CC(=C(C=C1CC(C(=O)O)N)O)O
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
InChIKey
WTDRDQBEARUVNC-LURJTMIESA-N
CAS Number
CAS 59-92-7
ChEBI ID
CHEBI:15765
Herb ID
HBIN033038
SymMap ID
SMIT03076
TCMSP ID
MOL000482
TTD Drug ID
D08HVR
Combinatorial Therapeutic Effect(s) Validated Clinically or Experimentally
    α. A List of Drug(s) Whose Efficacy can be Enhanced by This NP
          Celecoxib      Rheumatoid arthritis     Click to Show/Hide the Molecular Data of This Drug
                 Achieving Therapeutic Synergy     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [2]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    In-vivo Model Parkinsonian rats were used as animal model in this study.
                    Experimental
                    Result(s)		 L-DOPA + celecoxib combination produces an antiallodynic and antihyperalgesic synergistic interaction at the systemic level, and these effects are mediated, at the central level, through activation of the NO-cGMP-ATP-sensitive K+ channel pathway.
Target and Pathway
Target(s) Dopamine D2 receptor (D2R)  Molecule Info  [1]
KEGG Pathway Rap1 signaling pathway Click to Show/Hide
2 cAMP signaling pathway
3 Neuroactive ligand-receptor interaction
4 Gap junction
5 Dopaminergic synapse
6 Parkinson's disease
7 Cocaine addiction
8 Alcoholism
Panther Pathway Heterotrimeric G-protein signaling pathway-Gi alpha and Gs alpha mediated pathway Click to Show/Hide
2 Heterotrimeric G-protein signaling pathway-Gq alpha and Go alpha mediated pathway
3 Dopamine receptor mediated signaling pathway
4 Nicotine pharmacodynamics pathway
Reactome Dopamine receptors Click to Show/Hide
2 G alpha (i) signalling events
WikiPathways Hypothetical Network for Drug Addiction Click to Show/Hide
2 Monoamine GPCRs
3 GPCRs, Class A Rhodopsin-like
4 Genes and (Common) Pathways Underlying Drug Addiction
5 GPCR ligand binding
6 GPCR downstream signaling
7 Nicotine Activity on Dopaminergic Neurons
References
Reference 1 URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 3639).
Reference 2 Synergistic antiallodynic and antihyperalgesic interaction between L-DOPA and celecoxib in parkinsonian rats is mediated by NO-cGMP-ATP-sensitive K + channel. Eur J Pharmacol. 2020 Dec 15;889:173537.
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