Levodopa

Details

• Internal ID: 739369c0-c659-4cc6-ba8f-f0473a72df2f
• Taxonomy: Organic acids and derivatives > Carboxylic acids and derivatives > Amino acids, peptides, and analogues > Alpha amino acids and derivatives > Tyrosine and derivatives
• IUPAC Name: (2S)-2-amino-3-(3,4-dihydroxyphenyl)propanoic acid
• SMILES (Canonical): C1=CC(=C(C=C1CC(C(=O)O)N)O)O
• SMILES (Isomeric): C1=CC(=C(C=C1C[C@@H](C(=O)O)N)O)O
• InChI: 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
• InChI Key: WTDRDQBEARUVNC-LURJTMIESA-N
• Popularity: 46,018 references in papers

Physical and Chemical Properties

• Molecular Formula: C₉H₁₁NO₄
• Molecular Weight: 197.19 g/mol
• Exact Mass: 197.06880783 g/mol
• Topological Polar Surface Area (TPSA): 104.00 Ų
• XlogP: -2.70
• Atomic LogP (AlogP): 0.05
• H-Bond Acceptor: 4
• H-Bond Donor: 4
• Rotatable Bonds: 3

Synonyms

• L-dopa
• 59-92-7
• Dopar
• 3,4-dihydroxy-L-phenylalanine
• 3-Hydroxy-L-tyrosine
• Bendopa
• Larodopa
• Levopa
• 3,4-Dihydroxyphenylalanine
• Brocadopa
• Cidandopa
• Dopaidan
• Dopalina
• Insulamina
• Maipedopa
• Dopasol
• Eldopal
• Eldopar
• Pardopa
• Prodopa
• Syndopa
• Helfo-Dopa
• (-)-Dopa
• Dihydroxy-L-phenylalanine
• Deadopa
• Dopaflex
• 3-(3,4-Dihydroxyphenyl)-L-alanine
• Doparkine
• Dopaston
• Dopastral
• Eldopatec
• Eurodopa
• Doparl
• Doprin
• Veldopa
• Dopal-fher
• L-3,4-Dihydroxyphenylalanine
• (2S)-2-amino-3-(3,4-dihydroxyphenyl)propanoic acid
• Levodopum
• L-o-Hydroxytyrosine
• Dopa
• Levedopa
• Ledopa
• (-)-3-(3,4-Dihydroxyphenyl)-L-alanine
• L-Tyrosine, 3-hydroxy-
• Dopaston SE
• L-(o-Dihydroxyphenyl)alanine
• Laradopa
• Biodopa
• Parda
• beta-(3,4-Dihydroxyphenyl)-L-alanine
• L-(-)-Dopa
• 3,4-Dihydroxyphenyl-L-alanine
• L-beta-(3,4-Dihydroxyphenyl)alanine
• L-3-(3,4-Dihydroxyphenyl)alanine
• L-3-Hydroxytyrosine
• Cerepap
• Inbrija
• Sobiodopa
• Weldopa
• Ro 4-6316
• beta-(3,4-Dihydroxyphenyl)alanine
• L-Dihydroxyphenylalanine
• C9H11NO4
• Helfo DOPA
• L Dopa
• (S)-2-amino-3-(3,4-dihydroxyphenyl)propanoic acid
• L-O-Dihydroxyphenylalanine
• CVT-301
• CCRIS 3766
• Levodopum [INN-Latin]
• CHEBI:15765
• L(-)-Dopa
• HSDB 3348
• alanine, 3-(3,4-dihydroxyphenyl)-, L-
• beta-(3,4-Dihydroxyphenyl)-alpha-L-alanine
• L-beta-(3,4-Dihydroxyphenyl)-alpha-alanine
• dihydroxyphenylalanine
• EINECS 200-445-2
• Alanine, 3-(3,4-dihydroxyphenyl)-, (-)-
• component of Sinemet
• NSC 118381
• NSC-118381
• Dopar (TN)
• DTXSID9023209
• beta-(3,4-Dihydroxyphenyl)-alpha-alanine
• UNII-46627O600J
• 3,4-Dihydroxyphenylalanine (VAN)
• (-)-(3,4-Dihydroxyphenyl)alanine
• NSC118381
• DOPA, L-
• L-.beta.-(3,4-Dihydroxyphenyl)alanine
• CHEMBL1009
• .beta.-(3,4-Dihydroxyphenyl)-L-alanine
• DHIVY COMPONENT LEVODOPA
• DTXCID303209
• DUOPA COMPONENT LEVODOPA
• RYTARY COMPONENT LEVODOPA
• 46627O600J
• L-(3,4-Dihydroxyphenyl)alanine
• PARCOPA COMPONENT LEVODOPA
• STALEVO COMPONENT LEVODOPA
• Levodopa [USAN:INN:BAN:JAN]
• CARBILEV COMPONENT LEVODOPA
• CORBILTA COMPONENT LEVODOPA
• DOPASNAP COMPONENT LEVODOPA
• IPX203 COMPONENT LEVODOPA
• V-1512
• LEVODOPA COMPONENT OF DHIVY
• LEVODOPA COMPONENT OF DUOPA
• IPX-203 COMPONENT LEVODOPA
• LEVODOPA COMPONENT OF RYTARY
• LEVODOPA COMPONENT OF PARCOPA
• LEVODOPA COMPONENT OF SINEMET
• LEVODOPA COMPONENT OF STALEVO
• Inbrija (levodopa inhalation powder)
• LEVODOPA COMPONENT OF CARBILEV
• LEVODOPA COMPONENT OF CORBILTA
• LEVODOPA COMPONENT OF DOPASNAP
• .beta.-(3,4-Dihydroxyphenyl)alanine
• Levodopa [USAN:USP:INN:BAN:JAN]
• CAS-59-92-7
• Tyrosine, 3-hydroxy-
• NCGC00016270-04
• L-(3,4-Dihydroxyphenyl)-.alpha.-alanine
• MFCD00002598
• LEVODOPA (MART.)
• LEVODOPA [MART.]
• LEVODOPA (EP IMPURITY)
• LEVODOPA [EP IMPURITY]
• L-dihydroxy-phenylalanine
• LEVODOPA (EP MONOGRAPH)
• LEVODOPA [EP MONOGRAPH]
• LEVODOPA (USP MONOGRAPH)
• LEVODOPA [USP MONOGRAPH]
• LEVODOPA/CARBIDOPA/ENTACAPONE ORION COMPONENT LEVODOPA
• LEVODOPA COMPONENT OF LEVODOPA/CARBIDOPA/ENTACAPONE ORION
• BDBM50130192
• 3 Hydroxy L tyrosine
• WLN: QVYZ1R CQ DQ
• SR-01000075384
• L-3,4-Dihydrophenylalanine
• Dopastone
• Dopicar
• Prolopa
• L 3,4 Dihydroxyphenylalanine
• levodopa-
• (2S)-2-amino-3-(3,4-dihydroxyphenyl)propanoate
• IV Levodopa
• Prestwick_185
• Levodopa (Sinemet)
• L-DOPA; Levodopa
• Madopa (Salt/Mix)
• Spectrum_000454
• 4-dihydroxyphenylalanine
• LEVODOPA [HSDB]
• LEVODOPA [USAN]
• LEVODOPA [INN]
• LEVODOPA [JAN]
• Carbidopa EP Impurity A
• LEVODOPA [MI]
• LEVODOPA [VANDF]
• Prestwick0_000017
• Prestwick1_000017
• Prestwick2_000017
• Prestwick3_000017
• Spectrum2_000496
• Spectrum4_000539
• Spectrum5_001899
• L-Tirosina, 3-hidroxi-
• Lopac-D-9628
• Levodopa (JP15/USP)
• bmse000322
• D08HVR
• Epitope ID:150927
• LEVODOPA [USP-RS]
• LEVODOPA [WHO-DD]
• LEVODOPA [WHO-IP]
• 3, 4-Dihydroxyphenylalanine
• Alanine,4-dihydroxyphenyl)-
• LEVODOPA [EMA EPAR]
• 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
• LEVODOPA [ORANGE BOOK]
• BPBio1_000059
• GTPL3639
• b-(3,4-Dihydroxyphenyl)alanine
• WLN: QVYZ1R CQ DQ -L
• 3, 4-Dihydroxy-L-phenylalanine
• BDBM60928
• HMS501G14
• KBio1_000452
• KBio2_000934
• KBio2_003502
• KBio2_006070
• Levodopa [USAN:BAN:INN:JAN]
• LEVODOPUM [WHO-IP LATIN]
• N04BA01
• Alanine,4-dihydroxyphenyl)-, L-
• L-(3, 4-Dihydroxyphenyl)alanine
• NINDS_000452
• HMS1568C15
• HMS1922J14
• HMS2090O08
• HMS2093N04
• HMS2095C15
• HMS2230B04
• HMS3261K10
• HMS3712C15
• Pharmakon1600-02300205
• H-Phe{3,4-(OH)2}-OH
• HY-N0304
• Levodopa;3,4-Dihydroxyphenylalanine
• b-(3,4-Dihydroxyphenyl)-L-alanine
• Tox21_110338
• Tox21_500454
• CCG-39571
• HB1925
• L-3-(3,4-dihydroxy-phenyl)alanine
• L-3-(3,4-dihydroxyphenyl)-Alanine
• LS-255
• NSC759573
• PDSP1_001541
• PDSP2_001525
• s1726
• Alanine, 3-(3,4-dihydroxyphenyl)-
• Alanine,4-dihydroxyphenyl)-, (-)-
• AKOS010396267
• b-(3,4-Dihydroxyphenyl)-a-L-alanine
• L-b-(3,4-Dihydroxyphenyl)-a-alanine
• L-DOPA (3,4-Dihydroxyphenylalanine)
• .beta.-(3, 4-Dihydroxyphenyl)alanine
• AC-8432
• AM82124
• CS-1945
• DB01235
• LP00454
• NSC-759573
• SDCCGMLS-0066924.P001
• SDCCGSBI-0050439.P004
• IDI1_000452
• NCGC00015384-01
• NCGC00016270-01
• NCGC00016270-06
• NCGC00016270-07
• NCGC00016270-09
• NCGC00016270-10
• NCGC00016270-22
• NCGC00093869-04
• NCGC00261139-01
• AS-13287
• BP-12850
• SMR000058312
• SBI-0050439.P003
• (--)-3-(3,4-Dihydroxyphenyl)-L-alanine
• L-(3, 4-Dihydroxyphenyl)-.alpha.-alanine
• BETA-(3,4-DIHYDROPHENYL)-L-ALANINE
• D0600
• D9628
• EU-0100454
• EN300-52637
• Alanine, 3-(3, 4-dihydroxyphenyl)-, (-)-
• C00355
• D 9628
• D00059
• D70595
• 3,4-Dihydroxy-L-phenylalanine, >=98% (TLC)
• AB00052418-06
• AB00052418-07
• AB00052418_08
• AB00052418_09
• A832543
• Q300989
• (2S)-2-amino-3-(3,4-dihydroxyphenyl)propanoicacid
• Q-201294
• SR-01000075384-1
• SR-01000075384-4
• SR-01000075384-6
• SR-01000075384-7
• (--)-2Amino-3-(3,4-dihydroxyphenyl)propanoic Acid
• Levodopa (optimized formulation, Parkinson's disease)
• More effective levodopa (Parkinson's disease), Orion
• (S)-2-Amino-3-(3,4-dihydroxy-phenyl)-propionic acid
• F0347-4695
• Levodopa, British Pharmacopoeia (BP) Reference Standard
• Levodopa, European Pharmacopoeia (EP) Reference Standard
• Z756440064
• (2S)-2-amino-3-(3,4-dihydroxyphenyl)propanoic acidL-dopa
• 1E83F927-C221-46AA-B90A-81B33C5F3868
• 3,4-Dihydroxy-L-phenylalanine, Vetec(TM) reagent grade, 98%
• Levodopa (optimized formulation, Parkinson's disease), Orion
• 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
• 65170-01-6
• 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

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9662	96.62%
Caco-2	-	0.9372	93.72%
Blood Brain Barrier	-	0.9000	90.00%
Human oral bioavailability	-	0.7286	72.86%
Subcellular localzation	Nucleus	0.4463	44.63%
OATP2B1 inhibitior	-	0.8630	86.30%
OATP1B1 inhibitior	+	0.9736	97.36%
OATP1B3 inhibitior	+	0.9490	94.90%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	-	0.9162	91.62%
P-glycoprotein inhibitior	-	0.9946	99.46%
P-glycoprotein substrate	-	0.9723	97.23%
CYP3A4 substrate	-	0.7772	77.72%
CYP2C9 substrate	-	0.6291	62.91%
CYP2D6 substrate	-	0.7403	74.03%
CYP3A4 inhibition	-	0.9140	91.40%
CYP2C9 inhibition	-	0.9765	97.65%
CYP2C19 inhibition	-	0.9504	95.04%
CYP2D6 inhibition	-	0.9576	95.76%
CYP1A2 inhibition	-	0.9467	94.67%
CYP2C8 inhibition	-	0.8861	88.61%
CYP inhibitory promiscuity	-	0.9713	97.13%
UGT catelyzed	+	0.5362	53.62%
Carcinogenicity (binary)	-	0.5200	52.00%
Carcinogenicity (trinary)	Non-required	0.7666	76.66%
Eye corrosion	-	0.9948	99.48%
Eye irritation	+	0.7199	71.99%
Skin irritation	-	0.6993	69.93%
Skin corrosion	-	0.8968	89.68%
Ames mutagenesis	+	0.6600	66.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.8122	81.22%
Micronuclear	+	0.7500	75.00%
Hepatotoxicity	-	0.7875	78.75%
skin sensitisation	+	0.5821	58.21%
Respiratory toxicity	+	0.8333	83.33%
Reproductive toxicity	+	0.9000	90.00%
Mitochondrial toxicity	+	0.9375	93.75%
Nephrotoxicity	-	0.8797	87.97%
Acute Oral Toxicity (c)	III	0.8019	80.19%
Estrogen receptor binding	-	0.9124	91.24%
Androgen receptor binding	+	0.6384	63.84%
Thyroid receptor binding	-	0.7859	78.59%
Glucocorticoid receptor binding	-	0.7387	73.87%
Aromatase binding	-	0.9480	94.80%
PPAR gamma	-	0.6168	61.68%
Honey bee toxicity	-	0.9398	93.98%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.7800	78.00%
Fish aquatic toxicity	-	0.3886	38.86%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL2903	P16050	Arachidonate 15-lipoxygenase	39810.7 nM	Potency	via CMAUP
CHEMBL1293236	P46063	ATP-dependent DNA helicase Q1	12589.3 nM	Potency	via CMAUP
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	158.5 nM	Potency	via Super-PRED
CHEMBL4159	Q99714	Endoplasmic reticulum-associated amyloid beta-peptide-binding protein	316.2 nM; 3981.1 nM; 316.2 nM	Potency; Potency; Potency	via Super-PRED; via CMAUP; via CMAUP
CHEMBL203	P00533	Epidermal growth factor receptor erbB1	2880 nM; 900000 nM	IC50; IC50	via CMAUP; PMID: 2552117
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	10000 nM; 10000 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL1293226	B2RXH2	Lysine-specific demethylase 4D-like	12589.3 nM	Potency	via CMAUP
CHEMBL1841	P06241	Tyrosine-protein kinase FYN	2146 nM	IC50	via CMAUP
CHEMBL258	P06239	Tyrosine-protein kinase LCK	3729 nM	IC50	via CMAUP
CHEMBL1075138	Q9NUW8	Tyrosyl-DNA phosphodiesterase 1	125.9 nM; 562.3 nM; 501.2 nM; 501.2 nM	Potency; Potency; Potency; Potency	via Super-PRED; via Super-PRED; via Super-PRED; via CMAUP
CHEMBL1293227	O75604	Ubiquitin carboxyl-terminal hydrolase 2	20749.1 nM	Potency	via CMAUP

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.15%	96.09%
CHEMBL2581	P07339	Cathepsin D	92.33%	98.95%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	91.96%	99.15%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	89.91%	94.45%
CHEMBL3060	Q9Y345	Glycine transporter 2	89.57%	99.17%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	89.31%	96.95%
CHEMBL1255126	O15151	Protein Mdm4	88.59%	90.20%
CHEMBL3976	Q9UHL4	Dipeptidyl peptidase II	87.65%	92.29%
CHEMBL3492	P49721	Proteasome Macropain subunit	87.50%	90.24%
CHEMBL236	P41143	Delta opioid receptor	86.12%	99.35%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.36%	95.56%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	84.06%	95.50%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	83.92%	97.21%
CHEMBL1951	P21397	Monoamine oxidase A	81.81%	91.49%

Plants that contains it

• Astragalus hamosus
• Bruguiera cylindrica
• Crataegus laevigata
• Ecbolium ligustrinum
• Euphorbia lathyris
• Jacobaea arnautorum
• Kalanchoe marmorata
• Littorella uniflora
• Machilus robusta
• Mucuna holtonii
• Mucuna pruriens
• Mucuna pruriens var. utilis
• Musa × paradisiaca
• Phegopteris subaurita
• Portulaca grandiflora
• Portulaca oleracea
• Spatholobus suberectus
• Symphytum tuberosum
• Thymus quinquecostatus var. przewalskii
• Thymus transcaucasicus

Cross-Links

• PubChem: 6047
• NPASS: NPC161593
• ChEMBL: CHEMBL1009
• LOTUS: LTS0130329
• wikiData: Q300989