NP-MRD: Showing NP-Card for DL-Dopa (NP0000491)

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Record Information

Version

2.0

Created at

2005-11-16 15:48:42 UTC

Updated at

2024-09-17 15:42:02 UTC

NP-MRD ID

NP0000491

Secondary Accession Numbers

None

Natural Product Identification

Common Name

DL-Dopa

Description

DL-DOPA, also known as (+-)-DOPA or (R,S)-DOPA or DL-3,4-dihydroxyphenylalanine is an alpha amino acid. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon). DL-DOPA also belongs to the class of organic compounds known as tyrosines and derivatives. Tyrosines 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. DL-DOPA is a racemic mixture of both D-DOPA and L-DOPA. D-DOPA is similar to L-DOPA (levodopa), but with opposite chirality. Levo- and dextro- rotation refer to a molecule's ability to rotate planes of polarized light in one or the other direction. Whereas L-DOPA is moderately effective in the treatment of Parkinson's disease (PD) by stimulating the production of dopamine in the brain, D-DOPA was at one time thought to be biologically inactive. However, it has recently been found that D-DOPA can be converted to L-DOPA and then to dopamine via the human enzyme known as D-amino acid oxidase and that racemic mixtures of DL-DOPA can be effective in treating Parkinsonism (PMID: 17924443 ; PMID: 3129126 ; PMID: 17042912 ). The biological production or biosynthesis of D-DOPA is thought to occur through bacterial conversion of tyrosine. L-DOPA is found naturally in both animals and plants. It is made via biosynthesis from the amino acid L-tyrosine by the enzyme tyrosine hydroxylase. L-DOPA is the precursor to the neurotransmitters dopamine, norepinephrine (noradrenaline), and epinephrine (adrenaline), which are collectively known as catecholamines.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

  Mrv1652305271900102D          

 14 14  0  0  0  0            999 V2000
   15.3793   -8.6665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6648   -9.0790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8082   -8.6665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0937   -9.9040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0937   -9.0790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8082   -7.8415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6648   -9.9040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3793  -10.3165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5227   -7.4290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0937   -7.4290    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.9503  -10.3165    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.3793  -11.1414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.5227   -6.6040    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.2371   -7.8415    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  5  2  0  0  0  0
  1  2  1  0  0  0  0
  2  7  2  0  0  0  0
  3  6  1  0  0  0  0
  3  5  1  0  0  0  0
  4  8  2  0  0  0  0
  4  5  1  0  0  0  0
  6 10  1  0  0  0  0
  6  9  1  0  0  0  0
  7 11  1  0  0  0  0
  7  8  1  0  0  0  0
  8 12  1  0  0  0  0
  9 13  1  0  0  0  0
  9 14  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0000491

> <DATABASE_NAME>
NP-MRD

> <SMILES>
NC(CC1=CC=C(O)C(O)=C1)C(O)=O

> <INCHI_IDENTIFIER>
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)

> <INCHI_KEY>
WTDRDQBEARUVNC-UHFFFAOYSA-N

> <FORMULA>
C9H11NO4

> <MOLECULAR_WEIGHT>
197.1879

> <EXACT_MASS>
197.068807845

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
25

> <JCHEM_AVERAGE_POLARIZABILITY>
19.079841092462985

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-amino-3-(3,4-dihydroxyphenyl)propanoic acid

> <ALOGPS_LOGP>
-2.32

> <JCHEM_LOGP>
-1.7921814507627933

> <ALOGPS_LOGS>
-1.78

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.686049362161093

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.650696949850563

> <JCHEM_PKA_STRONGEST_BASIC>
9.055027392905787

> <JCHEM_POLAR_SURFACE_AREA>
103.78

> <JCHEM_REFRACTIVITY>
49.0781

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.30e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3',4'-dihydroxyphenylalanine

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  C   UNK     0      28.708 -16.177   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      27.374 -16.947   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      31.375 -16.177   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      30.042 -18.487   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      30.042 -16.947   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      31.375 -14.637   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      27.374 -18.487   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      28.708 -19.257   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      32.709 -13.867   0.000  0.00  0.00           C+0
HETATM   10  N   UNK     0      30.042 -13.867   0.000  0.00  0.00           N+0
HETATM   11  O   UNK     0      26.041 -19.257   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      28.708 -20.797   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      32.709 -12.327   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0      34.043 -14.637   0.000  0.00  0.00           O+0
CONECT    1    5    2                                                       
CONECT    2    1    7                                                       
CONECT    3    6    5                                                       
CONECT    4    8    5                                                       
CONECT    5    1    3    4                                                  
CONECT    6    3   10    9                                                  
CONECT    7    2   11    8                                                  
CONECT    8    4    7   12                                                  
CONECT    9    6   13   14                                                  
CONECT   10    6                                                            
CONECT   11    7                                                            
CONECT   12    8                                                            
CONECT   13    9                                                            
CONECT   14    9                                                            
MASTER        0    0    0    0    0    0    0    0   14    0   28    0
END

View in JSmol View NMR Assignments

Synonyms

Value	Source
(+-)-3-(3,4-Dihydroxyphenyl)alanine	ChEBI
(+-)-Dopa	ChEBI
(R,S)-Dopa	ChEBI
3',4'-Dihydroxyphenylalanine	ChEBI
3-Hydroxy-DL-tyrosine	ChEBI
3-Hydroxytyrosine	ChEBI
beta-(3,4-Dihydroxyphenyl)-DL-alpha-alanine	ChEBI
DL-3,4-Dopa	ChEBI
DL-beta-(3,4-Dihydroxyphenyl)-alpha-alanine	ChEBI
DL-beta-(3,4-Dihydroxyphenyl)alanine	ChEBI
DL-Dihydroxyphenylalanine	ChEBI
DL-Dioxyphenylalanine	ChEBI
b-(3,4-Dihydroxyphenyl)-DL-a-alanine	Generator
Β-(3,4-dihydroxyphenyl)-DL-α-alanine	Generator
DL-b-(3,4-Dihydroxyphenyl)-a-alanine	Generator
DL-Β-(3,4-dihydroxyphenyl)-α-alanine	Generator
DL-b-(3,4-Dihydroxyphenyl)alanine	Generator
DL-Β-(3,4-dihydroxyphenyl)alanine	Generator
(+/-) 3-(3,4-dihydroxyphenyl)alanine	HMDB
2-Amino-3-(3,4-dihydroxyphenyl)propanoate	HMDB
2-Amino-3-(3,4-dihydroxyphenyl)propanoic acid	HMDB
3,4-Dihydroxy-DL-phenylalanine	HMDB
3,4-Dihydroxyphenylalanine	HMDB
3-(3,4-Dihydroxyphenyl)-DL-alanine	HMDB
a-Amino-3,4-dihydroxy-benzenepropanoate	HMDB
a-Amino-3,4-dihydroxy-benzenepropanoic acid	HMDB
alpha-Amino-3,4-dihydroxy-benzenepropanoate	HMDB
alpha-Amino-3,4-dihydroxy-benzenepropanoic acid	HMDB
alpha-Amino-hydrocaffeic acid	HMDB
b-(3,4-Dihydroxyphenyl)-a-alanine	HMDB
beta-(3,4-Dihydroxyphenyl)-alpha-alanine	HMDB
DL-3',4'-Dihydroxyphenylalanine	HMDB
DL-3,4-Dihydroxyphenylalanine	HMDB
DL-3-Hydroxytyrosine	HMDB
DL-4,5-Dihydroxyphenylalanine	HMDB
Dopa	HMDB
3 Hydroxy DL tyrosine	HMDB
3,4 Dihydroxyphenylalanine	HMDB
beta-Hydroxytyrosine	HMDB
Dihydroxyphenylalanine hydrochloride, (2:1)	HMDB
beta Hydroxytyrosine	HMDB
Dihydroxyphenylalanine	HMDB

Chemical Formula

C₉H₁₁NO₄

Average Mass

197.1879 Da

Monoisotopic Mass

197.06881 Da

IUPAC Name

2-amino-3-(3,4-dihydroxyphenyl)propanoic acid

Traditional Name

3',4'-dihydroxyphenylalanine

CAS Registry Number

63-84-3

SMILES

NC(CC1=CC=C(O)C(O)=C1)C(O)=O

InChI Identifier

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)

InChI Key

WTDRDQBEARUVNC-UHFFFAOYSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Amaranthus mangostanus	Plant	KNApSAcK
Anas platyrhynchos	FooDB	FooDB
Anatidae	FooDB	FooDB
Anser anser	FooDB	FooDB
Basella alba	Plant	KNApSAcK
Beta vulgaris	Plant	KNApSAcK
Bison bison	FooDB	FooDB
Bos taurus	FooDB	FooDB
Bos taurus X Bison bison	FooDB	FooDB
Brassica olereacea	Plant	KNApSAcK
Bubalus bubalis	FooDB	FooDB
Capra aegagrus hircus	FooDB	FooDB
Celosia argentea	Plant	KNApSAcK
Cervidae	FooDB	FooDB
Cervus canadensis	FooDB	FooDB
Chenopodium quinoa	Plant	KNApSAcK
Citrus X sinensis (L.) Osbeck (pro. sp.)	Plant	KNApSAcK
Columba	FooDB	FooDB
Columbidae	FooDB	FooDB
Cytisus coparius	Plant	KNApSAcK
Dromaius novaehollandiae	FooDB	FooDB
Equus caballus	FooDB	FooDB
Gallus gallus	FooDB	FooDB
Glottiphyllum longum	-	KNApSAcK
Gomphrena globosa	Plant	KNApSAcK
Lagopus muta	FooDB	FooDB
Leporidae	FooDB	FooDB
Lepus timidus	FooDB	FooDB
Lophophora williamsii	Plant	KNApSAcK
Lupinus spp.	Plant	KNApSAcK
Melanitta fusca	FooDB	FooDB
Meleagris gallopavo	FooDB	FooDB
Mirabilis jalapa	Plant	KNApSAcK
Mucuna priuriens	Plant	KNApSAcK
Mucuna pruriens	LOTUS Database	35616633
Mucuna sloanei	Plant	KNApSAcK
Mucuna spp.	Plant	KNApSAcK
Musa acuminata	Plant	KNApSAcK
Numida meleagris	FooDB	FooDB
Odocoileus	FooDB	FooDB
Opuntia elatior	Plant	KNApSAcK
Opuntia ficus-indica	Plant	KNApSAcK
Oryctolagus	FooDB	FooDB
Ovis aries	FooDB	FooDB
Persea americana	Plant	KNApSAcK
Phaseolus vulgaris	Plant	KNApSAcK
Phasianidae	FooDB	FooDB
Phasianus colchicus	FooDB	FooDB
Pisum sativum	Plant	KNApSAcK
Plantago major	Plant	KNApSAcK
Portulaca grandiflora	Plant	KNApSAcK
Rivina humilis	Plant	KNApSAcK
Solanum lycopersicum	Plant	KNApSAcK
Solanum melanogena	Plant	KNApSAcK
Spinacia oleracea	Plant	KNApSAcK
Struthio camelus	FooDB	FooDB
Sus scrofa	FooDB	FooDB
Sus scrofa domestica	FooDB	FooDB
Tenebrio molitor	LOTUS Database	35616633
Theobroma cacao	Plant	KNApSAcK
Vicia faba	Plant	KNApSAcK

Species Where Detected

Species Name	Source	Reference
Streptoalloteichus hindustanus	KNApSAcK Database	22123792

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

Substituents

Tyrosine or derivatives
Phenylalanine or derivatives
3-phenylpropanoic-acid
Amphetamine or derivatives
Alpha-amino acid
Catechol
1-hydroxy-2-unsubstituted benzenoid
1-hydroxy-4-unsubstituted benzenoid
Phenol
Aralkylamine
Monocyclic benzene moiety
Benzenoid
Amino acid
Monocarboxylic acid or derivatives
Carboxylic acid
Hydrocarbon derivative
Organic oxygen compound
Organooxygen compound
Organonitrogen compound
Primary aliphatic amine
Organic nitrogen compound
Carbonyl group
Organic oxide
Organopnictogen compound
Amine
Primary amine
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

non-proteinogenic alpha-amino acid (CHEBI:49168 )
tyrosine derivative (CHEBI:49168 )
hydroxyphenylalanine (CHEBI:49168 )

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	270 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	3.6 mg/mL	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	3.3 g/L	ALOGPS
logP	-2.3	ALOGPS
logP	-1.8	ChemAxon
logS	-1.8	ALOGPS
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 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	49.08 m³·mol⁻¹	ChemAxon
Polarizability	19.08 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0000609

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Dihydroxyphenylalanine

METLIN ID

Not Available

PubChem Compound

836

PDB ID

Not Available

ChEBI ID

49168

Good Scents ID

Not Available

References

General References

Goldstein DS, Eisenhofer G, Kopin IJ: Sources and significance of plasma levels of catechols and their metabolites in humans. J Pharmacol Exp Ther. 2003 Jun;305(3):800-11. Epub 2003 Mar 20. [PubMed:12649306 ]
Ichise M, Kim YJ, Ballinger JR, Vines D, Erami SS, Tanaka F, Lang AE: SPECT imaging of pre- and postsynaptic dopaminergic alterations in L-dopa-untreated PD. Neurology. 1999 Apr 12;52(6):1206-14. [PubMed:10214745 ]
Kesten SR, Heffner TG, Johnson SJ, Pugsley TA, Wright JL, Wise LD: Design, synthesis, and evaluation of chromen-2-ones as potent and selective human dopamine D4 antagonists. J Med Chem. 1999 Sep 9;42(18):3718-25. [PubMed:10479303 ]
Furukawa Y, Nygaard TG, Gutlich M, Rajput AH, Pifl C, DiStefano L, Chang LJ, Price K, Shimadzu M, Hornykiewicz O, Haycock JW, Kish SJ: Striatal biopterin and tyrosine hydroxylase protein reduction in dopa-responsive dystonia. Neurology. 1999 Sep 22;53(5):1032-41. [PubMed:10496263 ]
Preising M, Op de Laak JP, Lorenz B: Deletion in the OA1 gene in a family with congenital X linked nystagmus. Br J Ophthalmol. 2001 Sep;85(9):1098-103. [PubMed:11520764 ]
Yoshida M, Hirotsu S, Nakahara M, Uchiwa H, Tomita Y: Histamine is involved in ultraviolet B-induced pigmentation of guinea pig skin. J Invest Dermatol. 2002 Feb;118(2):255-60. [PubMed:11841541 ]
Ito K, Nagano-Saito A, Kato T, Arahata Y, Nakamura A, Kawasumi Y, Hatano K, Abe Y, Yamada T, Kachi T, Brooks DJ: Striatal and extrastriatal dysfunction in Parkinson's disease with dementia: a 6-[18F]fluoro-L-dopa PET study. Brain. 2002 Jun;125(Pt 6):1358-65. [PubMed:12023324 ]
Bohme TM, Augelli-Szafran CE, Hallak H, Pugsley T, Serpa K, Schwarz RD: Synthesis and pharmacology of benzoxazines as highly selective antagonists at M(4) muscarinic receptors. J Med Chem. 2002 Jul 4;45(14):3094-102. [PubMed:12086495 ]
Misu Y, Kitahama K, Goshima Y: L-3,4-Dihydroxyphenylalanine as a neurotransmitter candidate in the central nervous system. Pharmacol Ther. 2003 Feb;97(2):117-37. [PubMed:12559386 ]
Moore RY, Whone AL, McGowan S, Brooks DJ: Monoamine neuron innervation of the normal human brain: an 18F-DOPA PET study. Brain Res. 2003 Aug 29;982(2):137-45. [PubMed:12915249 ]
Scherfler C, Khan NL, Pavese N, Eunson L, Graham E, Lees AJ, Quinn NP, Wood NW, Brooks DJ, Piccini PP: Striatal and cortical pre- and postsynaptic dopaminergic dysfunction in sporadic parkin-linked parkinsonism. Brain. 2004 Jun;127(Pt 6):1332-42. Epub 2004 Apr 16. [PubMed:15090472 ]
Moore RT, Chae KA, Rhodes AR: Laugier and Hunziker pigmentation: a lentiginous proliferation of melanocytes. J Am Acad Dermatol. 2004 May;50(5 Suppl):S70-4. [PubMed:15097932 ]
Sun M, Kong L, Wang X, Holmes C, Gao Q, Zhang GR, Pfeilschifter J, Goldstein DS, Geller AI: Coexpression of tyrosine hydroxylase, GTP cyclohydrolase I, aromatic amino acid decarboxylase, and vesicular monoamine transporter 2 from a helper virus-free herpes simplex virus type 1 vector supports high-level, long-term biochemical and behavioral correction of a rat model of Parkinson's disease. Hum Gene Ther. 2004 Dec;15(12):1177-96. [PubMed:15684695 ]
Pahwa R, Lyons KE, Hauser RA: Ropinirole therapy for Parkinson's disease. Expert Rev Neurother. 2004 Jul;4(4):581-8. [PubMed:15853577 ]
Mann R, Bhathal PS, Bell C: Sympathetic innervation of the liver in man and dog: an immunohistochemical study. Clin Auton Res. 1991 Jun;1(2):141-5. [PubMed:1688040 ]
Tohgi H, Abe T, Kikuchi T, Takahashi S, Nozaki Y: The significance of 3-O-methyldopa concentrations in the cerebrospinal fluid in the pathogenesis of wearing-off phenomenon in Parkinson's disease. Neurosci Lett. 1991 Oct 28;132(1):19-22. [PubMed:1787913 ]
Shigetomi S, Buu NT, Kuchel O: Dopaminergic abnormalities in borderline essential hypertensive patients. Hypertension. 1991 Jun;17(6 Pt 2):997-1002. [PubMed:1904403 ]
Gill JR Jr, Grossman E, Goldstein DS: High urinary dopa and low urinary dopamine-to-dopa ratio in salt-sensitive hypertension. Hypertension. 1991 Nov;18(5):614-21. [PubMed:1937664 ]
Rosen CF, Seki Y, Farinelli W, Stern RS, Fitzpatrick TB, Pathak MA, Gange RW: A comparison of the melanocyte response to narrow band UVA and UVB exposure in vivo. J Invest Dermatol. 1987 Jun;88(6):774-9. [PubMed:3108414 ]
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Showing NP-Card for DL-Dopa (NP0000491)

MOL for NP0000491 (DL-Dopa)

3D MOL for NP0000491 (DL-Dopa)

3D SDF for NP0000491 (DL-Dopa)

3D-SDF for NP0000491 (DL-Dopa)

PDB for NP0000491 (DL-Dopa)

3D PDB for NP0000491 (DL-Dopa)

SMILES for NP0000491 (DL-Dopa)

INCHI for NP0000491 (DL-Dopa)

Structure for NP0000491 (DL-Dopa)

3D Structure for NP0000491 (DL-Dopa)