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Human Metabolome Database Version 3.5

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Showing metabocard for L-Dopa (HMDB00181)

Record Information
Version 3.5
Creation Date 2005-11-16 08:48:42 -0700
Update Date 2013-02-08 17:08:02 -0700
HMDB ID HMDB00181
Secondary Accession Numbers None
Metabolite Identification
Common Name L-Dopa
Description L-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
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
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 Formula C9H11NO4
Average Molecular Weight 197.1879
Monoisotopic Molecular Weight 197.068807845
IUPAC Name (2S)-2-amino-3-(3,4-dihydroxyphenyl)propanoic acid
Traditional IUPAC Name levodopa
CAS Registry Number 59-92-7
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 Key WTDRDQBEARUVNC-LURJTMIESA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Amino Acids, Peptides, and Analogues
Class Amino Acids and Derivatives
Sub Class Alpha 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 Parent Alpha Amino Acids and Derivatives
Ontology
Status Detected and Quantified
Origin
  • Endogenous
Biofunction
  • Component of Riboflavin metabolism
  • Component of Stilbene, coumarine and lignin biosynthesis
  • Component of Tyrosine metabolism
Application Not Available
Cellular locations
  • Cytoplasm
  • Extracellular
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point 285 °C Not Available
Boiling Point Not Available Not Available
Water Solubility 5.0 mg/mL Not Available
LogP -2.39 SANGSTER (1993)
Predicted Properties
Property Value Source
Water Solubility 3.3 g/L ALOGPS
LogP -2.32 ALOGPS
LogP -1.8 ChemAxon
LogS -1.78 ALOGPS
pKa (strongest acidic) 1.65 ChemAxon
pKa (strongest basic) 9.06 ChemAxon
Hydrogen Acceptor Count 5 ChemAxon
Hydrogen Donor Count 4 ChemAxon
Polar Surface Area 103.78 A2 ChemAxon
Rotatable Bond Count 3 ChemAxon
Refractivity 49.08 ChemAxon
Polarizability 19.02 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 0 ChemAxon
Spectra
1H NMR Spectrum
MS/MS Spectrum Quattro_QQQ 10
MS/MS Spectrum Quattro_QQQ 25
MS/MS Spectrum Quattro_QQQ 40
MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic)
MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic)
MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic)
MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic)
MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic)
MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic)
MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic)
MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic)
MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic)
MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic)
MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic)
MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic)
[1H,13C] 2D NMR Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biofluid Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Urine
Tissue Location
  • Muscle
  • Bladder
  • Intestine
  • Neuron
  • Placenta
  • Epidermis
  • Brain
  • Adrenal Medulla
  • Nerve Cells
  • Platelet
  • Striatum
Pathways
Name SMPDB Link KEGG Link
Tyrosine Metabolism SMP00006 map00350 Link_out
Catecholamine Biosynthesis SMP00012 map00350 Link_out
Normal Concentrations
Biofluid Status Value Age Sex Condition Comments
Blood Detected and Quantified
Article_icon
0.00723 +/- 0.00097 uM Adult (>18 years old) Both Normal Not Available
Cerebrospinal Fluid (CSF) Detected and Quantified
Article_icon
0.0035 +/- 0.0009 uM Adult (>18 years old) Not Specified Normal Not Available
Cerebrospinal Fluid (CSF) Detected and Quantified
Article_icon
<0.025 uM Children (1-13 year old) Male Normal Not Available
Urine Detected and Quantified
Article_icon
0.02 (0.01-0.04) umol/mmol creatinine Adult (>18 years old) Both Normal by LC-MS/MS (Biocrates kit)
Urine Detected and Quantified
Article_icon
0.008 (0.0036-0.0138) umol/mmol creatinine Children (1-13 year old) Both Normal Not Available
Urine Detected and Quantified
Article_icon
0.0136 +/- 0.0033 umol/mmol creatinine Adult (>18 years old) Both Normal Not Available
Abnormal Concentrations
Biofluid Status Value Age Sex Condition Comments
Blood Detected and Quantified
Article_icon
14.0 +/- 2.53 uM Elderly (>65 years old) Both Alzheimer's disease Not Available
Cerebrospinal Fluid (CSF) Detected and Quantified
Article_icon
<0.001 uM Children (1-13 year old) Male sepiapterin reductase deficiency Not Available
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 Link_out
    Associated OMIM IDs
    DrugBank ID DB01235 Link_out
    Phenol Explorer Compound ID Not Available
    Phenol Explorer Metabolite ID Not Available
    FoodDB ID FDB000567
    KNApSAcK ID C00001357 Link_out
    Chemspider ID 5824 Link_out
    KEGG Compound ID C00355 Link_out
    BioCyc ID L-DOPA Link_out
    BiGG ID 34719 Link_out
    Wikipedia Link L-Dopa Link_out
    NuGOwiki Link HMDB00181 Link_out
    Metagene Link HMDB00181 Link_out
    METLIN ID 42 Link_out
    PubChem Compound 6047 Link_out
    PDB ID DAH Link_out
    ChEBI ID 15765 Link_out
    References
    Synthesis Reference Haneda, 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) Download (PDF)
    General References
    1. 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 Link_out
    2. 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 Link_out
    3. 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 Link_out
    4. 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 Link_out
    5. 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 Link_out
    6. 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 Link_out
    7. 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 Link_out
    8. 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 Link_out
    9. 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 Link_out
    10. 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 Link_out
    11. 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 Link_out
    12. 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 Link_out
    13. Hyland K, Clayton PT: Aromatic L-amino acid decarboxylase deficiency: diagnostic methodology. Clin Chem. 1992 Dec;38(12):2405-10. Pubmed: 1281049 Link_out
    14. 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 Link_out
    15. 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 Link_out
    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 Link_out
    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 Link_out
    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 Link_out
    Enzymes
    Name: Tyrosinase
    Reactions:
    • L-tyrosine + L-dopa + O2 = L-dopa + dopaquinone + H2O [RN:R02078]
    Gene Name: TYR
    Uniprot ID: P14679 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: Catechol O-methyltransferase
    Reactions:
    • S-adenosyl-L-methionine + a catechol = S-adenosyl-L-homocysteine + a guaiacol [RN:R07330]
    Gene Name: COMT
    Uniprot ID: P21964 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: Tyrosine 3-monooxygenase
    Reactions:
    • L-tyrosine + tetrahydrobiopterin + O2 = 3,4-dihydroxy-L-phenylalanine + 4a-hydroxytetrahydrobiopterin [RN:R07212]
    Gene Name: TH
    Uniprot ID: P07101 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: Aromatic-L-amino-acid decarboxylase
    Reactions:
    • (1) 3,4-dihydroxy-L-phenylalanine = dopamine + CO2 [RN:R02080]
    • (2) 5-hydroxy-L-tryptophan = 5-hydroxytryptamine + CO2 [RN:R02701]
    Gene Name: DDC
    Uniprot ID: P20711 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: Cytochrome P450 2D6
    Reactions:
    • RH + reduced flavoprotein + O2 = ROH + oxidized flavoprotein + H2O [RN:R04122]
    Gene Name: CYP2D6
    Uniprot ID: P10635 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: D(2) dopamine receptor
    Reactions:
      Gene Name: DRD2
      Uniprot ID: P14416 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: D(4) dopamine receptor
      Reactions:
        Gene Name: DRD4
        Uniprot ID: P21917 Link_out
        Protein Sequence: FASTA
        Gene Sequence: FASTA
        Name: 4F2 cell-surface antigen heavy chain
        Reactions:
          Gene Name: SLC3A2
          Uniprot ID: P08195 Link_out
          Protein Sequence: FASTA
          Gene Sequence: FASTA
          Name: D(3) dopamine receptor
          Reactions:
            Gene Name: DRD3
            Uniprot ID: P35462 Link_out
            Protein Sequence: FASTA
            Gene Sequence: FASTA
            Name: D(1A) dopamine receptor
            Reactions:
              Gene Name: DRD1
              Uniprot ID: P21728 Link_out
              Protein Sequence: FASTA
              Gene Sequence: FASTA
              Name: D(1B) dopamine receptor
              Reactions:
                Gene Name: DRD5
                Uniprot ID: P21918 Link_out
                Protein Sequence: FASTA
                Gene Sequence: FASTA
                Transporters
                Name: Solute carrier family 15 member 1
                Reactions:
                  Gene Name: SLC15A1
                  Uniprot ID: P46059 Link_out
                  Protein Sequence: FASTA
                  Gene Sequence: FASTA
                  Name: Monocarboxylate transporter 10
                  Reactions:
                    Gene Name: SLC16A10
                    Uniprot ID: Q8TF71 Link_out
                    Protein Sequence: FASTA
                    Gene Sequence: FASTA