Record Information
Version1.0
Creation date2010-04-08 22:04:37 UTC
Update date2018-05-29 00:29:31 UTC
Primary IDFDB000567
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameL-DOPA
DescriptionOccurs in seedlings and pods of Vicia faba L-DOPA (L-3,4-dihydroxyphenylalanine; INN levodopa; trade names Sinemet, Parcopa, Atamet, Stalevo, Madopar, Prolopa, etc.) is a naturally-occurring dietary supplement and psychoactive drug found in certain kinds of food and herbs (e.g., Mucuna pruriens, or velvet bean), and is synthesized from the amino acid L-tyrosine in the mammalian body and brain.
CAS Number59-92-7
Structure
Thumb
Synonyms
SynonymSource
(-)-3-(3,4-Dihydroxyphenyl)-L-alanineChEBI
(-)-DopaChEBI
3,4-Dihydroxy-L-phenylalanineChEBI
3,4-DIHYDROXYPHENYLALANINEChEBI
3-Hydroxy-L-tyrosineChEBI
beta-(3,4-Dihydroxyphenyl)-L-alanineChEBI
beta-(3,4-Dihydroxyphenyl)alanineChEBI
Dihydroxy-L-phenylalanineChEBI
DoparChEBI
L-beta-(3,4-Dihydroxyphenyl)alanineChEBI
LevodopaChEBI
LevodopumChEBI
b-(3,4-Dihydroxyphenyl)-L-alanineGenerator
Β-(3,4-dihydroxyphenyl)-L-alanineGenerator
b-(3,4-Dihydroxyphenyl)alanineGenerator
Β-(3,4-dihydroxyphenyl)alanineGenerator
L-b-(3,4-Dihydroxyphenyl)alanineGenerator
L-Β-(3,4-dihydroxyphenyl)alanineGenerator
(2S)-2-Amino-3-(3,4-dihydroxyphenyl)propanoateHMDB
(2S)-2-Amino-3-(3,4-dihydroxyphenyl)propanoic acidHMDB
3,4-Dihydroxyphenyl-L-alanineHMDB
3-(3,4-Dihydroxyphenyl)-L-alanineHMDB
b-(3,4-Dihydroxyphenyl)-a-L-alanineHMDB
BendopaHMDB
beta-(3,4-Dihydroxyphenyl)-alpha-L-alanineHMDB
CidandopaHMDB
DihydroxyphenylalanineHMDB
DopaflexHMDB
DopaidanHMDB
DopalHMDB
DopalinaHMDB
DoparkineHMDB
DoparlHMDB
DopasolHMDB
DopastonHMDB
DopastoneHMDB
DopastralHMDB
DopicarHMDB
DoprinHMDB
EldopalHMDB
EldoparHMDB
EldopatecHMDB
EurodopaHMDB
Helfo-dopaHMDB
InsulaminaHMDB
L-(-)-DopaHMDB
L-3-(3,4-Dihydroxyphenyl)-alanineHMDB
L-4-5-DihydroxyphenylalanineHMDB
L-b-(3,4-Dihydroxyphenyl)-a-alanineHMDB
L-beta-(3,4-Dihydroxyphenyl)-alpha-alanineHMDB
L-DihydroxyphenylalanineHMDB
LaradopaHMDB
LarodopaHMDB
LedopaHMDB
LevedopaHMDB
LevopaHMDB
MaipedopaHMDB
PardaHMDB
PardopaHMDB
ProdopaHMDB
SyndopaHMDB
VeldopaHMDB
WeldopaHMDB
3 Hydroxy L tyrosineHMDB
Roche brand OF levodopaHMDB
L 3,4 DihydroxyphenylalanineHMDB
L-3,4-DihydroxyphenylalanineHMDB
Medphano brand OF levodopaHMDB
L DopaHMDB
Roberts brand OF levodopaHMDB
(-)-(3,4-Dihydroxyphenyl)alaninebiospider
(-)-3-(3,4-dihydroxyphenyl)-L-alaninebiospider
(-)-DOPAbiospider
(2S)-2-amino-3-(3,4-dihydroxyphenyl)propanoatebiospider
(2S)-2-amino-3-(3,4-dihydroxyphenyl)propanoic acidbiospider
β-(3,4-Dihydroxyphenyl)-L-alaninebiospider
β-(3,4-Dihydroxyphenyl)alaninebiospider
2-Amino-3-(3,4-dihydroxyphenyl)propanoic acid; L-formdb_source
Alanine, 3-(3,4-dihydroxyphenyl)-, (-)-biospider
Alanine, 3-(3,4-dihydroxyphenyl)-, L-biospider
DOPAbiospider
L-(-)-DOPAbiospider
L-(3, 4-Dihydroxyphenyl)alaninebiospider
L-(3,4-Dihydroxyphenyl)-α-alaninebiospider
L-(3,4-Dihydroxyphenyl)alaninebiospider
L-β-(3,4-Dihydroxyphenyl)alaninebiospider
L-3-(3,4-dihydroxyphenyl)-Alaninebiospider
L-3-(3,4-Dihydroxyphenyl)alaninebiospider
L-3-Hydroxytyrosinebiospider
L-dihydroxyphenylalaninebiospider
L-DOPAbiospider
L-Tyrosine, 3-hydroxy-biospider
L-β-(3,4-dihydroxyphenyl)alanineGenerator
Levodopa, BAN, INN, JAN, USANdb_source
β-(3,4-dihydroxyphenyl)-L-alanineGenerator
β-(3,4-dihydroxyphenyl)alanineGenerator
Predicted Properties
PropertyValueSource
Water Solubility3.3 g/LALOGPS
logP-2.3ALOGPS
logP-1.8ChemAxon
logS-1.8ALOGPS
pKa (Strongest Acidic)1.65ChemAxon
pKa (Strongest Basic)9.06ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area103.78 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity49.08 m³·mol⁻¹ChemAxon
Polarizability18.91 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC9H11NO4
IUPAC name(2S)-2-amino-3-(3,4-dihydroxyphenyl)propanoic acid
InChI IdentifierInChI=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 KeyWTDRDQBEARUVNC-LURJTMIESA-N
Isomeric SMILESN[C@@H](CC1=CC(O)=C(O)C=C1)C(O)=O
Average Molecular Weight197.1879
Monoisotopic Molecular Weight197.068807845
Classification
Description belongs to the class of organic compounds known as tyrosine and derivatives. Tyrosine and derivatives are compounds containing tyrosine or a derivative thereof resulting from reaction of tyrosine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentTyrosine and derivatives
Alternative Parents
Substituents
  • Tyrosine or derivatives
  • Phenylalanine or derivatives
  • 3-phenylpropanoic-acid
  • Alpha-amino acid
  • Amphetamine or derivatives
  • L-alpha-amino acid
  • Catechol
  • 1-hydroxy-4-unsubstituted benzenoid
  • Aralkylamine
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Monocyclic benzene moiety
  • Benzenoid
  • Amino acid
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organic oxide
  • Organooxygen compound
  • Organonitrogen compound
  • Primary amine
  • Primary aliphatic amine
  • Organic nitrogen compound
  • Organic oxygen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Amine
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionC 54.82%; H 5.62%; N 7.10%; O 32.45%DFC
Melting PointMp 285.5° dec.DFC
Boiling PointNot Available
Experimental Water Solubility5 mg/mL at 20 oCYALKOWSKY,SH & DANNENFELSER,RM (1992)
Experimental logP-2.39SANGSTER (1993)
Experimental pKa2.32
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]20D -12.15 (c, 4 in 1N HCl)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (4 TMS)splash10-014i-0790000000-b2f7f063a2c8197c7eddView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-014i-0690000000-622497b3104c6082a45dView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (4 TMS)splash10-00xr-9350000000-b0cc4636931d2de64d81View in MoNA
GC-MSGC-MS Spectrum - GC-MS (4 TMS)splash10-014i-0590000000-4474e81e4226bb4e1d4cView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-014i-0790000000-b2f7f063a2c8197c7eddView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-014i-0690000000-622497b3104c6082a45dView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00xr-9350000000-b0cc4636931d2de64d81View in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-014i-0590000000-4474e81e4226bb4e1d4cView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-014i-1890000000-646d209fa1943582a336View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-014i-0690000000-720ed87e98a0d9f1721dView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0fk9-3900000000-266d9baeda773fe1fb22View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-0002-4193000000-8c76bf85d8a897e9403cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0uea-0900000000-8eb71aa0cc8622f097a2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0a59-2900000000-bf63b9b719959b82b543View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-056r-9300000000-a78b0b31dd33fe8479a7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0f6t-0911000000-15affa616923dfb9c45aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-000i-0900000000-22d8267801d0eb0b73c2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-001i-0900000000-2c310034a1a871502b4cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0udi-0900000000-5e6020c952f741531fcbView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0007-0970100000-49594dae82ce73e734e6View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-001i-0900000000-2183a68f58b951f3f1c7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-03di-0900000000-0030db588fbd92c5b761View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0006-0090000000-544615463a975baae9e4View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-0002-0729111000-0a20b01f58fff8ad7ef0View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-004i-0900000000-c8095a31ed4b3dbbc646View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-03di-0190000000-41515cba3a6929721859View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-0002-0900000000-8074c509ef5bae1129fcView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-0006-0502193020-497bfad7ba247159ca00View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-004i-0900000000-0b0d4b6dcb7f1fa24e1aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-004i-0029800000-05f40324c8c1fec7963aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-0006-0000090000-c0cd80185ce47b30e5feView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-0002-0900000000-df116b84981cf4a1371aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Positivesplash10-0f6t-0900000000-1c1c39a8880442ea18dfView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udj-0900000000-cf54b26df05181b0d2fcView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0900000000-d506f2673b114b8e38d2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00di-8900000000-1699873cb7650f62b5bcView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0900000000-a0d81bfc4868b0d1cbf9View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
ChemSpider ID5824
ChEMBL IDCHEMBL1009
KEGG Compound IDC00355
Pubchem Compound ID6047
Pubchem Substance IDNot Available
ChEBI ID15765
Phenol-Explorer IDNot Available
DrugBank IDDB01235
HMDB IDHMDB00181
CRC / DFC (Dictionary of Food Compounds) IDHHZ68-O:BDR85-N
EAFUS IDNot Available
Dr. Duke IDL-DOPA|DOPA
BIGG ID34719
KNApSAcK IDC00001357
HET IDDAH
Flavornet IDNot Available
GoodScent IDrw1253531
SuperScent IDNot Available
Wikipedia IDL-Dopa
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
analgesic35480 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.DUKE
anorexic50780 An agent which regulates the physiologic mechanisms that control the appetite and food intake.DUKE
antidote50247 Any protective agent counteracting or neutralizing the action of poisons.DUKE
anti encephalopathic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti feedantDUKE
anti morphinicDUKE
anti neuroleptic35470 A class of drugs producing both physiological and psychological effects through a variety of mechanisms involving the central nervous system.DUKE
anti Parkinsonian48407 A drug used in the treatment of Parkinson's disease.DUKE
anti reserpineDUKE
anti tremor52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
aphrodisiacDUKE
arrhythmigenic38070 A drug used for the treatment or prevention of cardiac arrhythmias. Anti-arrhythmia drugs may affect the polarisation-repolarisation phase of the action potential, its excitability or refractoriness, or impulse conduction or membrane responsiveness within cardiac fibres.DUKE
cardiovascular38070 A drug used for the treatment or prevention of cardiac arrhythmias. Anti-arrhythmia drugs may affect the polarisation-repolarisation phase of the action potential, its excitability or refractoriness, or impulse conduction or membrane responsiveness within cardiac fibres.DUKE
central nervous system active35470 A class of drugs producing both physiological and psychological effects through a variety of mechanisms involving the central nervous system.DUKE
depressantDUKE
diuretic35498 An agent that promotes the excretion of urine through its effects on kidney function.DUKE
dopaminergic48560 A drug used for its effects on dopamine receptors, on the life cycle of dopamine, or on the survival of dopaminergic neurons.DUKE
emeticDUKE
hallucinogen35499 Drugs capable of inducing illusions, hallucinations, delusions, paranoid ideations and other alterations of mood and thinking.DUKE
hypertensiveDUKE
hypotensiveDUKE
insectifuge24852 Strictly, a substance intended to kill members of the class Insecta. In common usage, any substance used for preventing, destroying, repelling or controlling insects.DUKE
miotic51068 Aa agent causing contraction of the pupil of the eye. Because the size of the pupil is under the antagonistic control of the sympathetic and parasympathetic systems, drugs affecting either system can cause miosis. Drugs that mimic or potentiate the parasympathetic input to the circular constrictor muscle and drugs that inhibit sympathetic input to the radial dilator muscle tend to contract the pupils.DUKE
natriureticDUKE
neurotoxic50910 A poison that interferes with the functions of the nervous system.CHEBI
Enzymes
NameGene NameUniProt ID
Aromatic-L-amino-acid decarboxylaseDDCP20711
Tyrosine 3-monooxygenaseTHP07101
D(2) dopamine receptorDRD2P14416
D(4) dopamine receptorDRD4P21917
Pathways
NameSMPDB LinkKEGG Link
Catecholamine BiosynthesisSMP00012 map00350
Tyrosine MetabolismSMP00006 map00350
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
odorless
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.
— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).