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Record Information
Version1.0
Created at2005-11-16 15:48:42 UTC
Updated at2021-08-09 22:33:14 UTC
NP-MRD IDNP0000491
Secondary Accession NumbersNone
Natural Product Identification
Common NameDL-Dopa
DescriptionDL-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
Thumb
Synonyms
ValueSource
(+-)-3-(3,4-Dihydroxyphenyl)alanineChEBI
(+-)-DopaChEBI
(R,S)-DopaChEBI
3',4'-DihydroxyphenylalanineChEBI
3-Hydroxy-DL-tyrosineChEBI
3-HydroxytyrosineChEBI
beta-(3,4-Dihydroxyphenyl)-DL-alpha-alanineChEBI
DL-3,4-DopaChEBI
DL-beta-(3,4-Dihydroxyphenyl)-alpha-alanineChEBI
DL-beta-(3,4-Dihydroxyphenyl)alanineChEBI
DL-DihydroxyphenylalanineChEBI
DL-DioxyphenylalanineChEBI
b-(3,4-Dihydroxyphenyl)-DL-a-alanineGenerator
Β-(3,4-dihydroxyphenyl)-DL-α-alanineGenerator
DL-b-(3,4-Dihydroxyphenyl)-a-alanineGenerator
DL-Β-(3,4-dihydroxyphenyl)-α-alanineGenerator
DL-b-(3,4-Dihydroxyphenyl)alanineGenerator
DL-Β-(3,4-dihydroxyphenyl)alanineGenerator
(+/-) 3-(3,4-dihydroxyphenyl)alanineHMDB
2-Amino-3-(3,4-dihydroxyphenyl)propanoateHMDB
2-Amino-3-(3,4-dihydroxyphenyl)propanoic acidHMDB
3,4-Dihydroxy-DL-phenylalanineHMDB
3,4-DihydroxyphenylalanineHMDB
3-(3,4-Dihydroxyphenyl)-DL-alanineHMDB
a-Amino-3,4-dihydroxy-benzenepropanoateHMDB
a-Amino-3,4-dihydroxy-benzenepropanoic acidHMDB
alpha-Amino-3,4-dihydroxy-benzenepropanoateHMDB
alpha-Amino-3,4-dihydroxy-benzenepropanoic acidHMDB
alpha-Amino-hydrocaffeic acidHMDB
b-(3,4-Dihydroxyphenyl)-a-alanineHMDB
beta-(3,4-Dihydroxyphenyl)-alpha-alanineHMDB
DL-3',4'-DihydroxyphenylalanineHMDB
DL-3,4-DihydroxyphenylalanineHMDB
DL-3-HydroxytyrosineHMDB
DL-4,5-DihydroxyphenylalanineHMDB
DopaHMDB
3 Hydroxy DL tyrosineHMDB
3,4 DihydroxyphenylalanineHMDB
beta-HydroxytyrosineHMDB
Dihydroxyphenylalanine hydrochloride, (2:1)HMDB
beta HydroxytyrosineHMDB
DihydroxyphenylalanineHMDB
Chemical FormulaC9H11NO4
Average Mass197.1879 Da
Monoisotopic Mass197.06881 Da
IUPAC Name2-amino-3-(3,4-dihydroxyphenyl)propanoic acid
Traditional Name3',4'-dihydroxyphenylalanine
CAS Registry Number63-84-3
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 KeyWTDRDQBEARUVNC-UHFFFAOYSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Amaranthus mangostanusPlant
Anas platyrhynchosFooDB
AnatidaeFooDB
Anser anserFooDB
Basella albaPlant
Beta vulgarisPlant
Bison bisonFooDB
Bos taurusFooDB
Bos taurus X Bison bisonFooDB
Brassica olereaceaPlant
Bubalus bubalisFooDB
Capra aegagrus hircusFooDB
Celosia argenteaPlant
CervidaeFooDB
Cervus canadensisFooDB
Chenopodium quinoaPlant
Citrus X sinensis (L.) Osbeck (pro. sp.)Plant
ColumbaFooDB
ColumbidaeFooDB
Cytisus copariusPlant
Dromaius novaehollandiaeFooDB
Equus caballusFooDB
Gallus gallusFooDB
Glottiphyllum longum-
Gomphrena globosaPlant
Lagopus mutaFooDB
LeporidaeFooDB
Lepus timidusFooDB
Lophophora williamsiiPlant
Lupinus spp.Plant
Melanitta fuscaFooDB
Meleagris gallopavoFooDB
Mirabilis jalapaPlant
Mucuna priuriensPlant
Mucuna pruriensLOTUS Database
Mucuna sloaneiPlant
Mucuna spp.Plant
Musa acuminataPlant
Numida meleagrisFooDB
OdocoileusFooDB
Opuntia elatiorPlant
Opuntia ficus-indicaPlant
OryctolagusFooDB
Ovis ariesFooDB
Persea americanaPlant
Phaseolus vulgarisPlant
PhasianidaeFooDB
Phasianus colchicusFooDB
Pisum sativumPlant
Plantago majorPlant
Portulaca grandifloraPlant
Rivina humilisPlant
Solanum lycopersicumPlant
Solanum melanogenaPlant
Spinacia oleraceaPlant
Struthio camelusFooDB
Sus scrofaFooDB
Sus scrofa domesticaFooDB
Tenebrio molitorLOTUS Database
Theobroma cacaoPlant
Vicia fabaPlant
Species Where Detected
Species NameSourceReference
Streptoalloteichus hindustanusKNApSAcK Database
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.
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
  • 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 FrameworkAromatic homomonocyclic compounds
External Descriptors
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point270 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility3.6 mg/mLNot Available
LogPNot AvailableNot Available
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
Polarizability19.08 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0000609
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB022140
KNApSAcK IDC00018152
Chemspider ID813
KEGG Compound IDC00355
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkDihydroxyphenylalanine
METLIN IDNot Available
PubChem Compound836
PDB IDNot Available
ChEBI ID49168
Good Scents IDNot Available
References
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. 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 ]
  3. 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 ]
  4. 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 ]
  5. 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 ]
  6. 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 ]
  7. 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 ]
  8. 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 ]
  9. 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 ]
  10. 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 ]
  11. 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 ]
  12. 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 ]
  13. 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 ]
  14. Pahwa R, Lyons KE, Hauser RA: Ropinirole therapy for Parkinson's disease. Expert Rev Neurother. 2004 Jul;4(4):581-8. [PubMed:15853577 ]
  15. 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 ]
  16. 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 ]
  17. Shigetomi S, Buu NT, Kuchel O: Dopaminergic abnormalities in borderline essential hypertensive patients. Hypertension. 1991 Jun;17(6 Pt 2):997-1002. [PubMed:1904403 ]
  18. 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 ]
  19. 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 ]
  20. Boomsma F, van der Hoorn FA, Schalekamp MA: Determination of aromatic-L-amino acid decarboxylase in human plasma. Clin Chim Acta. 1986 Sep 15;159(2):173-83. [PubMed:3769207 ]
  21. Muskiet FA, Fremouw-Ottevangers DC, van der Meulen J, Wolthers BG, de Vries JA: Determination of some L-3,4-dihydroxyphenylalanine and dopamine metabolites in urine by means of mass fragmentography. Clin Chem. 1978 Jan;24(1):122-7. [PubMed:73430 ]
  22. Eldrup E, Mogensen P, Jacobsen J, Pakkenberg H, Christensen NJ: CSF and plasma concentrations of free norepinephrine, dopamine, 3,4-dihydroxyphenylacetic acid (DOPAC), 3,4-dihydroxyphenylalanine (DOPA), and epinephrine in Parkinson's disease. Acta Neurol Scand. 1995 Aug;92(2):116-21. [PubMed:7484057 ]
  23. Ikeda H, Pastuszko A, Ikegaki N, Kennett RH, Wilson DF: 3,4-dihydroxyphenylalanine (dopa) metabolism and retinoic acid induced differentiation in human neuroblastoma. Neurochem Res. 1994 Dec;19(12):1487-94. [PubMed:7877718 ]
  24. Cumming P, Gjedde A: Compartmental analysis of dopa decarboxylation in living brain from dynamic positron emission tomograms. Synapse. 1998 May;29(1):37-61. [PubMed:9552174 ]
  25. Kishore A, Nygaard TG, de la Fuente-Fernandez R, Naini AB, Schulzer M, Mak E, Ruth TJ, Calne DB, Snow BJ, Stoessl AJ: Striatal D2 receptors in symptomatic and asymptomatic carriers of dopa-responsive dystonia measured with [11C]-raclopride and positron-emission tomography. Neurology. 1998 Apr;50(4):1028-32. [PubMed:9566390 ]
  26. Nakazawa K, Sahuc F, Damour O, Collombel C, Nakazawa H: Regulatory effects of heat on normal human melanocyte growth and melanogenesis: comparative study with UVB. J Invest Dermatol. 1998 Jun;110(6):972-7. [PubMed:9620308 ]
  27. Kawazoe T, Park HK, Iwana S, Tsuge H, Fukui K: Human D-amino acid oxidase: an update and review. Chem Rec. 2007;7(5):305-15. doi: 10.1002/tcr.20129. [PubMed:17924443 ]
  28. Karoum F, Freed WJ, Chuang LW, Cannon-Spoor E, Wyatt RJ, Costa E: D-dopa and L-dopa similarly elevate brain dopamine and produce turning behavior in rats. Brain Res. 1988 Feb 2;440(1):190-4. doi: 10.1016/0006-8993(88)91176-6. [PubMed:3129126 ]
  29. Wu M, Zhou XJ, Konno R, Wang YX: D-dopa is unidirectionally converted to L-dopa by D-amino acid oxidase, followed by dopa transaminase. Clin Exp Pharmacol Physiol. 2006 Nov;33(11):1042-6. doi: 10.1111/j.1440-1681.2006.04484.x. [PubMed:17042912 ]