Structural search and advanced query search is temporarily unavailable. We are working to fix this issue. Thank you for your support and patience.

Record Information
Version	2.0
Creation Date	2015-06-04 19:10:39 -0600
Update Date	2015-08-05 16:22:05 -0600
Secondary Accession Numbers	ECMDB23839
Identification
Name:	3,4-Dihydroxy-L-phenylalanine
Description	An optically active form of dopa having L-configuration. Used to treat the stiffness, tremors, spasms, and poor muscle control of Parkinson's disease
Structure	MOLSDF3D-SDFPDBSMILESInChI View 3D Structure × Structure for #<Compound:0xa8142960> Close
Synonyms:	(-)-3-(3,4-Dihydroxyphenyl)-L-alanine (-)-Dopa (2S)-2-amino-3-(3,4-Dihydroxyphenyl)propanoate (2S)-2-amino-3-(3,4-Dihydroxyphenyl)propanoic acid 3,4-Dihydroxy-L-phenylalanine 3,4-Dihydroxyphenyl-L-alanine 3,4-DIHYDROXYPHENYLALANINE 3-(3,4-Dihydroxyphenyl)-L-alanine 3-Hydroxy-L-tyrosine b-(3,4-Dihydroxyphenyl)-a-L-alanine b-(3,4-Dihydroxyphenyl)-L-alanine b-(3,4-Dihydroxyphenyl)alanine Bendopa beta-(3,4-Dihydroxyphenyl)-alpha-L-alanine beta-(3,4-Dihydroxyphenyl)-L-alanine beta-(3,4-Dihydroxyphenyl)alanine Cidandopa Dihydroxy-L-phenylalanine Dihydroxyphenylalanine Dopaflex Dopaidan Dopal Dopalina Dopar Doparkine Doparl Dopasol Dopaston Dopastone Dopastral Dopicar Doprin Eldopal Eldopar Eldopatec Eurodopa helfo-Dopa Insulamina L-(-)-Dopa L-3-(3,4-Dihydroxyphenyl)-alanine L-4-5-Dihydroxyphenylalanine L-b-(3,4-Dihydroxyphenyl)-a-alanine L-b-(3,4-Dihydroxyphenyl)alanine L-beta-(3,4-Dihydroxyphenyl)-alpha-alanine L-beta-(3,4-Dihydroxyphenyl)alanine L-Dihydroxyphenylalanine L-β-(3,4-Dihydroxyphenyl)-α-alanine L-β-(3,4-dihydroxyphenyl)alanine Laradopa Larodopa Ledopa Levedopa Levodopum Levopa Maipedopa Parda Pardopa Prodopa Syndopa Veldopa Weldopa β-(3,4-dihydroxyphenyl)-L-alanine β-(3,4-Dihydroxyphenyl)-α-L-alanine β-(3,4-dihydroxyphenyl)alanine
Chemical Formula:	C9H11NO4
Weight:	Average: 197.1879 Monoisotopic: 197.068807845
InChI Key:	WTDRDQBEARUVNC-LURJTMIESA-N
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
CAS number:	59-92-7
IUPAC Name:	(2S)-2-amino-3-(3,4-dihydroxyphenyl)propanoic acid
Traditional IUPAC Name:	levodopa
SMILES:	N[C@@H](CC1=CC(O)=C(O)C=C1)C(O)=O
Chemical Taxonomy
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.
Kingdom	Organic compounds
Super Class	Organic acids and derivatives
Class	Carboxylic acids and derivatives
Sub Class	Amino acids, peptides, and analogues
Direct Parent	Tyrosine and derivatives
Alternative Parents	Phenylalanine and derivatives Phenylpropanoic acids L-alpha-amino acids Amphetamines and derivatives Catechols 1-hydroxy-2-unsubstituted benzenoids 1-hydroxy-4-unsubstituted benzenoids Aralkylamines Amino acids Monocarboxylic acids and derivatives Carboxylic acids Carbonyl compounds Hydrocarbon derivatives Monoalkylamines Organic oxides Organopnictogen compounds
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 Framework	Aromatic homomonocyclic compounds
External Descriptors	non-proteinogenic L-alpha-amino acid (CHEBI:15765 ) L-tyrosine derivative (CHEBI:15765 ) dopa (CHEBI:15765 ) Other amino acids (C00355 ) Biogenic amines (C00355 )
Physical Properties
State:	Not Available
Charge:	0
Melting point:	Not Available
Experimental Properties:	Property Value Source
Predicted Properties	Property Value Source logP -1.8 ChemAxon pKa (Strongest Acidic) 1.65 ChemAxon pKa (Strongest Basic) 9.06 ChemAxon Physiological Charge 0 ChemAxon Hydrogen Acceptor Count 5 ChemAxon Hydrogen Donor Count 4 ChemAxon Polar Surface Area 103.78 Ų ChemAxon Rotatable Bond Count 3 ChemAxon Refractivity 49.08 m³·mol⁻¹ ChemAxon Polarizability 18.91 ų ChemAxon Number of Rings 1 ChemAxon Bioavailability 1 ChemAxon Rule of Five Yes ChemAxon Ghose Filter Yes ChemAxon Veber's Rule Yes ChemAxon MDDR-like Rule Yes ChemAxon
Biological Properties
Cellular Locations:	Cytoplasm
Reactions:	3,4-Dihydroxy-L-phenylalanine + Oxygen <> 4-(L-Alanin-3-yl)-2-hydroxy-cis,cis-muconate 6-semialdehyde
SMPDB Pathways:	Not Available
KEGG Pathways:	Tyrosine metabolism ec00350
EcoCyc Pathways:	Not Available
Concentrations
	Not Available
Spectra
Spectra:	Spectrum Type Description Splash Key GC-MS GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (4 TMS) splash10-014i-0790000000-b2f7f063a2c8197c7edd View in MoNA GC-MS GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized) splash10-014i-0690000000-622497b3104c6082a45d View in MoNA GC-MS GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (4 TMS) splash10-00xr-9350000000-b0cc4636931d2de64d81 View in MoNA GC-MS GC-MS Spectrum - GC-MS (4 TMS) splash10-014i-0590000000-4474e81e4226bb4e1d4c View in MoNA GC-MS GC-MS Spectrum - GC-EI-TOF (Non-derivatized) splash10-014i-0790000000-b2f7f063a2c8197c7edd View in MoNA GC-MS GC-MS Spectrum - GC-EI-TOF (Non-derivatized) splash10-014i-0690000000-622497b3104c6082a45d View in MoNA GC-MS GC-MS Spectrum - GC-EI-TOF (Non-derivatized) splash10-00xr-9350000000-b0cc4636931d2de64d81 View in MoNA GC-MS GC-MS Spectrum - GC-MS (Non-derivatized) splash10-014i-0590000000-4474e81e4226bb4e1d4c View in MoNA GC-MS GC-MS Spectrum - GC-EI-TOF (Non-derivatized) splash10-014i-1890000000-646d209fa1943582a336 View in MoNA GC-MS GC-MS Spectrum - GC-EI-TOF (Non-derivatized) splash10-014i-0690000000-720ed87e98a0d9f1721d View in MoNA Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive splash10-0fk9-3900000000-266d9baeda773fe1fb22 View in MoNA Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positive splash10-0002-4193000000-8c76bf85d8a897e9403c View in MoNA Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TMS_1_4) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TMS_2_4) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TMS_2_5) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TMS_2_6) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TMS_2_7) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TMS_3_2) - 70eV, Positive Not Available View in JSpectraViewer LC-MS/MS LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated) splash10-0uea-0900000000-8eb71aa0cc8622f097a2 View in MoNA LC-MS/MS LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated) splash10-0a59-2900000000-bf63b9b719959b82b543 View in MoNA LC-MS/MS LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated) splash10-056r-9300000000-a78b0b31dd33fe8479a7 View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive splash10-0f6t-0911000000-15affa616923dfb9c45a View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive splash10-000i-0900000000-22d8267801d0eb0b73c2 View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive splash10-001i-0900000000-2c310034a1a871502b4c View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive splash10-0udi-0900000000-5e6020c952f741531fcb View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive splash10-0007-0970100000-49594dae82ce73e734e6 View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive splash10-001i-0900000000-2183a68f58b951f3f1c7 View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive splash10-03di-0900000000-0030db588fbd92c5b761 View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive splash10-0006-0090000000-544615463a975baae9e4 View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative splash10-0002-0729111000-0a20b01f58fff8ad7ef0 View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative splash10-004i-0900000000-c8095a31ed4b3dbbc646 View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative splash10-03di-0190000000-41515cba3a6929721859 View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative splash10-0002-0900000000-8074c509ef5bae1129fc View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative splash10-0006-0502193020-497bfad7ba247159ca00 View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative splash10-004i-0900000000-0b0d4b6dcb7f1fa24e1a View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative splash10-004i-0029800000-05f40324c8c1fec7963a View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative splash10-0006-0000090000-c0cd80185ce47b30e5fe View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive splash10-0002-0900000000-df116b84981cf4a1371a View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Positive splash10-0f6t-0900000000-1c1c39a8880442ea18df View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive splash10-0udj-0900000000-cf54b26df05181b0d2fc View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-0udi-0900000000-d506f2673b114b8e38d2 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-00di-8900000000-1699873cb7650f62b5bc View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-0002-0900000000-a0d81bfc4868b0d1cbf9 View in MoNA 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 2D NMR [1H,13C] 2D NMR Spectrum Not Available View in JSpectraViewer
References
References:	Not Available
Synthesis Reference:	Not Available
Material Safety Data Sheet (MSDS)	Not Available
Links
External Links:	Resource Link CHEBI ID 15765 HMDB ID HMDB0000181 Pubchem Compound ID 6047 Kegg ID C00355 ChemSpider ID 5824 Wikipedia ID Levodopa BioCyc ID Not Available