Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2013-02-09 00:08:02 UTC
HMDB IDHMDB00181
Secondary Accession NumbersNone
Metabolite Identification
Common NameL-Dopa
DescriptionL-Dopa is the naturally occurring form of dihydroxyphenylalanine and the immediate precursor of dopamine. Unlike dopamine itself, L-Dopa can be taken orally and crosses the blood-brain barrier. It is rapidly taken up by dopaminergic neurons and converted to dopamine. In particular, it is metabolized to dopamine by aromatic L-amino acid decarboxylase. Pyridoxal phosphate (vitamin B6) is a required cofactor for this decarboxylation, and may be administered along with levodopa, usually as pyridoxine. L-Dopa is used for the treatment of Parkinsonian disorders and Dopa-Responsive Dystonia and is usually given with agents that inhibit its conversion to dopamine outside of the central nervous system. Peripheral tissue conversion may be the mechanism of the adverse effects of levodopa. It is standard clinical practice to co-administer a peripheral DOPA decarboxylase inhibitor - carbidopa or benserazide - and often a catechol-O-methyl transferase (COMT) inhibitor, to prevent synthesis of dopamine in peripheral tissue.
Structure
Thumb
Synonyms
  1. (-)-3-(3,4-dihydroxyphenyl)-L-alanine
  2. (-)-Dopa
  3. (2S)-2-amino-3-(3,4-dihydroxyphenyl)propanoate
  4. (2S)-2-amino-3-(3,4-dihydroxyphenyl)propanoic acid
  5. 3,4-Dihydroxy-L-phenylalanine
  6. 3,4-Dihydroxyphenyl-L-alanine
  7. 3,4-Dihydroxyphenylalanine
  8. 3-(3,4-Dihydroxyphenyl)-L-alanine
  9. 3-Hydroxy-L-tyrosine
  10. b-(3,4-Dihydroxyphenyl)-a-L-alanine
  11. b-(3,4-Dihydroxyphenyl)-L-alanine
  12. b-(3,4-Dihydroxyphenyl)alanine
  13. Bendopa
  14. beta-(3,4-Dihydroxyphenyl)-alpha-L-alanine
  15. beta-(3,4-Dihydroxyphenyl)-L-alanine
  16. beta-(3,4-Dihydroxyphenyl)alanine
  17. Cidandopa
  18. Dihydroxy-L-phenylalanine
  19. Dihydroxyphenylalanine
  20. Dopaflex
  21. Dopaidan
  22. Dopal
  23. Dopalina
  24. Dopar
  25. Doparkine
  26. Doparl
  27. Dopasol
  28. Dopaston
  29. Dopastone
  30. Dopastral
  31. Dopicar
  32. Doprin
  33. Eldopal
  34. Eldopar
  35. Eldopatec
  36. Eurodopa
  37. Helfo-dopa
  38. Insulamina
  39. L-(-)-Dopa
  40. L-3-(3,4-Dihydroxyphenyl)-Alanine
  41. L-4-5-Dihydroxyphenylalanine
  42. L-b-(3,4-Dihydroxyphenyl)-a-alanine
  43. L-beta-(3,4-Dihydroxyphenyl)-alpha-alanine
  44. L-Dihydroxyphenylalanine
  45. L-Dopa
  46. Laradopa
  47. Larodopa
  48. Ledopa
  49. Levedopa
  50. Levodopa
  51. Levopa
  52. Maipedopa
  53. Parda
  54. Pardopa
  55. Prodopa
  56. Syndopa
  57. Veldopa
  58. Weldopa
Chemical FormulaC9H11NO4
Average Molecular Weight197.1879
Monoisotopic Molecular Weight197.068807845
IUPAC Name(2S)-2-amino-3-(3,4-dihydroxyphenyl)propanoic acid
Traditional IUPAC Namelevodopa
CAS Registry Number59-92-7
SMILES
N[C@@H](CC1=CC(O)=C(O)C=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)/t6-/m0/s1
InChI KeyWTDRDQBEARUVNC-LURJTMIESA-N
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassAmino Acids, Peptides, and Analogues
ClassAmino Acids and Derivatives
Sub ClassAlpha Amino Acids and Derivatives
Other Descriptors
  • Aromatic Homomonocyclic Compounds
  • Biogenic amines(KEGG)
  • Other amino acids(KEGG)
  • amino acid zwitterion(ChEBI)
Substituents
  • 1,2 Diphenol
  • Amphetamine Or Derivative
  • Carboxylic Acid
  • Catecholamine
  • Phenethylamine
  • Phenol
  • Phenol Derivative
  • Primary Aliphatic Amine (Alkylamine)
Direct ParentAlpha Amino Acids and Derivatives
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
Biofunction
  • Component of Riboflavin metabolism
  • Component of Stilbene, coumarine and lignin biosynthesis
  • Component of Tyrosine metabolism
ApplicationNot Available
Cellular locations
  • Cytoplasm
  • Extracellular
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point285 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility5.0 mg/mLNot Available
LogP-2.39SANGSTER (1993)
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 area103.78ChemAxon
rotatable bond count3ChemAxon
refractivity49.08ChemAxon
polarizability19.02ChemAxon
Spectra
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biofluid Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Urine
Tissue Location
  • Adrenal Medulla
  • Bladder
  • Brain
  • Epidermis
  • Intestine
  • Muscle
  • Nerve Cells
  • Neuron
  • Placenta
  • Platelet
  • Striatum
Pathways
NameSMPDB LinkKEGG Link
Catecholamine BiosynthesisSMP00012map00350
Tyrosine MetabolismSMP00006map00350
Normal Concentrations
BiofluidStatusValueAgeSexConditionReference
BloodDetected and Quantified0.00723 +/- 0.00097 uMAdult (>18 years old)BothNormal
  • Geigy Scient...
Cerebrospinal Fluid (CSF)Detected and Quantified0.0035 +/- 0.0009 uMAdult (>18 years old)Not SpecifiedNormal
Cerebrospinal Fluid (CSF)Detected and Quantified<0.025 uMChildren (1-13 year old)MaleNormal
UrineDetected and Quantified0.02 (0.01-0.04) umol/mmol creatinineAdult (>18 years old)BothCommentNormal
UrineDetected and Quantified0.008 (0.0036-0.0138) umol/mmol creatinineChildren (1-13 year old)BothNormal
  • Geigy Scient...
  • West Cadwell...
  • Basel, Switz...
UrineDetected and Quantified0.0136 +/- 0.0033 umol/mmol creatinineAdult (>18 years old)BothNormal
  • Geigy Scient...
  • West Cadwell...
  • Basel, Switz...
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReference
BloodDetected and Quantified14.0 +/- 2.53 uMElderly (>65 years old)BothAlzheimer's disease
Cerebrospinal Fluid (CSF)Detected and Quantified<0.001 uMChildren (1-13 year old)Malesepiapterin reductase deficiency
Associated Disorders and Diseases
Disease References
Alzheimer's disease
  • Fonteh AN, Harrington RJ, Tsai A, Liao P, Harrington MG: Free amino acid and dipeptide changes in the body fluids from Alzheimer's disease subjects. Amino Acids. 2007 Feb;32(2):213-24. Epub 2006 Oct 10. Pubmed: 17031479
Associated OMIM IDs
DrugBank IDDB01235
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB000567
KNApSAcK IDC00001357
Chemspider ID5824
KEGG Compound IDC00355
BioCyc IDL-DOPA
BiGG ID34719
Wikipedia LinkL-Dopa
NuGOwiki LinkHMDB00181
Metagene LinkHMDB00181
METLIN ID42
PubChem Compound6047
PDB IDDAH
ChEBI ID15765
References
Synthesis ReferenceHaneda, Katsuji; Watanabe, Shiro; Takeda, Isao. Synthesis ofL-3,4-dihydroxyphenylalanine from L-tyrosine by microorganisms. Applied Microbiology (1971), 22(4), 721-2.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. 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
  2. Cools R: Dopaminergic modulation of cognitive function-implications for L-DOPA treatment in Parkinson's disease. Neurosci Biobehav Rev. 2006;30(1):1-23. Epub 2005 Jun 1. Pubmed: 15935475
  3. de Jong AP, Kok RM, Cramers CA, Wadman SK, Haan E: A new method for the determination of L-dopa and 3-O-methyldopa in plasma and cerebrospinal fluid using gas chromatography and electron capture negative ion mass spectrometry. Clin Chim Acta. 1988 Jan 15;171(1):49-61. Pubmed: 3127089
  4. Dutton J, Copeland LG, Playfer JR, Roberts NB: Measuring L-dopa in plasma and urine to monitor therapy of elderly patients with Parkinson disease treated with L-dopa and a dopa decarboxylase inhibitor. Clin Chem. 1993 Apr;39(4):629-34. Pubmed: 8472357
  5. Mercuri NB, Bernardi G: The 'magic' of L-dopa: why is it the gold standard Parkinson's disease therapy? Trends Pharmacol Sci. 2005 Jul;26(7):341-4. Pubmed: 15936832
  6. Goldstein DS, Hahn SH, Holmes C, Tifft C, Harvey-White J, Milstien S, Kaufman S: Monoaminergic effects of folinic acid, L-DOPA, and 5-hydroxytryptophan in dihydropteridine reductase deficiency. J Neurochem. 1995 Jun;64(6):2810-3. Pubmed: 7760062
  7. Kagedal B, Pettersson A: Liquid-chromatographic determination of 5-S-L-cysteinyl-L-dopa with electrochemical detection in urine prepurified with a phenylboronate affinity gel. Clin Chem. 1983 Dec;29(12):2031-4. Pubmed: 6416708
  8. Dousa MK, Weinshilboum RM, Muenter MD, Offord KP, Decker PA, Tyce GM: L-DOPA biotransformation: correlations of dosage, erythrocyte catechol O-methyltransferase and platelet SULT1A3 activities with metabolic pathways in Parkinsonian patients. J Neural Transm. 2003 Aug;110(8):899-910. Pubmed: 12898345
  9. Di Stefano A, Mosciatti B, Cingolani GM, Giorgioni G, Ricciutelli M, Cacciatore I, Sozio P, Claudi F: Dimeric L-dopa derivatives as potential prodrugs. Bioorg Med Chem Lett. 2001 Apr 23;11(8):1085-8. Pubmed: 11327596
  10. Tada K, Kudo T, Kishimoto Y: Effects of L-dopa or dopamine on human decidual prostaglandin synthesis. Acta Med Okayama. 1991 Oct;45(5):333-8. Pubmed: 1755339
  11. Crivellato E, Damiani D, Mallardi F: Comparison between the L-DOPA histofluorescence procedure and the indirect immunofluorescence with anti-T6 and -HLA-DR monoclonal antibodies in visualizing Langerhans cells of human epidermis. Acta Histochem. 1990;88(1):59-64. Pubmed: 2113342
  12. Michel H, Solere M, Granier P, Cauvet G, Bali JP, Pons F, Bellet-Hermann H: Treatment of cirrhotic hepatic encephalopathy with L-dopa. A controlled trial. Gastroenterology. 1980 Aug;79(2):207-11. Pubmed: 6995221
  13. Streifler M, Avrami E, Rabey JM: L-dopa and the secretion of sebum in Parkinsonian patients. Eur Neurol. 1980;19(1):43-8. Pubmed: 7371653
  14. Hyland K, Clayton PT: Aromatic L-amino acid decarboxylase deficiency: diagnostic methodology. Clin Chem. 1992 Dec;38(12):2405-10. Pubmed: 1281049
  15. Vassiliou AG, Vassilacopoulou D, Fragoulis EG: Purification of an endogenous inhibitor of L-Dopa decarboxylase activity from human serum. Neurochem Res. 2005 May;30(5):641-9. Pubmed: 16176068
  16. Chalimoniuk M, Stepien A: Influence of the therapy with pergolide mesylate plus L-DOPA and with L-DOPA alone on serum cGMP level in PD patients. Pol J Pharmacol. 2004 Sep-Oct;56(5):647-50. Pubmed: 15591656
  17. Blandini F, Nappi G, Fancellu R, Mangiagalli A, Samuele A, Riboldazzi G, Calandrella D, Pacchetti C, Bono G, Martignoni E: Modifications of plasma and platelet levels of L-DOPA and its direct metabolites during treatment with tolcapone or entacapone in patients with Parkinson's disease. J Neural Transm. 2003 Aug;110(8):911-22. Pubmed: 12898346
  18. Shen H, Kannari K, Yamato H, Arai A, Matsunaga M: Effects of benserazide on L-DOPA-derived extracellular dopamine levels and aromatic L-amino acid decarboxylase activity in the striatum of 6-hydroxydopamine-lesioned rats. Tohoku J Exp Med. 2003 Mar;199(3):149-59. Pubmed: 12703659
  19. Kageyama T, Nakamura M, Matsuo A, Yamasaki Y, Takakura Y, Hashida M, Kanai Y, Naito M, Tsuruo T, Minato N, Shimohama S: The 4F2hc/LAT1 complex transports L-DOPA across the blood-brain barrier. Brain Res. 2000 Oct 6;879(1-2):115-21. Pubmed: 11011012
  20. Pinho MJ, Serrao MP, Gomes P, Hopfer U, Jose PA, Soares-da-Silva P: Over-expression of renal LAT1 and LAT2 and enhanced L-DOPA uptake in SHR immortalized renal proximal tubular cells. Kidney Int. 2004 Jul;66(1):216-26. Pubmed: 15200428

Enzymes

Gene Name:
TYR
Uniprot ID:
P14679
Reactions
L-Dopa + Oxygen unknown Dopaquinone + Waterdetails
L-Tyrosine + Oxygen unknown L-Dopa + Waterdetails
L-Dopa + L-Tyrosine + Oxygen unknown Dopaquinone + L-Dopa + Waterdetails
Gene Name:
COMT
Uniprot ID:
P21964
Gene Name:
TH
Uniprot ID:
P07101
Reactions
L-Tyrosine + L-erythro-tetrahydrobiopterin + Oxygen unknown L-Dopa + 4a-Hydroxytetrahydrobiopterindetails
L-erythro-tetrahydrobiopterin + L-Tyrosine + Oxygen unknown L-Dopa + 4a-Carbinolamine tetrahydrobiopterin + Waterdetails
Gene Name:
DDC
Uniprot ID:
P20711
Reactions
L-Dopa unknown Dopamine + CO(2)details
L-Dopa unknown Dopamine + Carbon dioxidedetails
Gene Name:
CYP2D6
Uniprot ID:
P10635
Gene Name:
DRD2
Uniprot ID:
P14416
Gene Name:
DRD4
Uniprot ID:
P21917
Gene Name:
SLC3A2
Uniprot ID:
P08195
Gene Name:
DRD3
Uniprot ID:
P35462
Gene Name:
DRD1
Uniprot ID:
P21728
Gene Name:
DRD5
Uniprot ID:
P21918

Transporters

Gene Name:
SLC15A1
Uniprot ID:
P46059
Gene Name:
SLC16A10
Uniprot ID:
Q8TF71