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L-DOPA (PC000210)

Record Information
Version1.0
Creation date2015-10-09 22:29:13 UTC
Update date2017-01-19 02:36:16 UTC
FoodComEx IDPC000210
FoodDB RecordFDB000567
Chemical Information
NameL-DOPA
DescriptionL-Dopa, also known as dopar or dopaston, 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. L-Dopa is a very strong basic compound (based on its pKa). L-Dopa exists in all living organisms, ranging from bacteria to humans. Within humans, L-dopa participates in a number of enzymatic reactions. In particular, L-dopa and tetrahydrobiopterin can be converted into dopamine and 4a-hydroxytetrahydrobiopterin through its interaction with the enzyme aromatic-L-amino-acid decarboxylase. In addition, L-dopa can be converted into dopaquinone; which is catalyzed by the enzyme tyrosinase. In humans, L-dopa is involved in the metabolic disorder called hawkinsinuria. L-Dopa is an odorless tasting compound. Outside of the human body, L-Dopa is found, on average, in the highest concentration within a few different foods, such as broad beans, swiss chards, and yellow wax beans and in a lower concentration in spinachs, garden onions, and green beans. L-Dopa has also been detected, but not quantified in, several different foods, such as chicory roots, bitter gourds, mustard spinachs, pistachio, and savoy cabbages. This could make L-dopa a potential biomarker for the consumption of these foods. L-Dopa is a potentially toxic compound. L-Dopa, with regard to humans, has been found to be associated with several diseases such as eosinophilic esophagitis and alzheimer's disease; L-dopa has also been linked to several inborn metabolic disorders including aromatic l-amino acid decarboxylase deficiency and sepiapterin reductase deficiency. An optically active form of dopa having L-configuration.
CAS Number59-92-7
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
SynonymSource
(-)-(3,4-Dihydroxyphenyl)alaninebiospider
(-)-3-(3,4-dihydroxyphenyl)-L-alaninebiospider
(-)-DOPAbiospider
(2S)-2-amino-3-(3,4-dihydroxyphenyl)propanoatebiospider
(2S)-2-amino-3-(3,4-dihydroxyphenyl)propanoic acidbiospider
β-(3,4-Dihydroxyphenyl)-L-alaninebiospider
β-(3,4-Dihydroxyphenyl)alaninebiospider
2-Amino-3-(3,4-dihydroxyphenyl)propanoic acid; L-formdb_source
3-(3,4-Dihydroxyphenyl)-L-alaninebiospider
3-Hydroxy-L-tyrosinebiospider
3,4-Dihydroxy-L-phenylalaninebiospider
3,4-Dihydroxyphenyl-L-alaninebiospider
Alanine, 3-(3,4-dihydroxyphenyl)-, (-)-biospider
Alanine, 3-(3,4-dihydroxyphenyl)-, L-biospider
b-(3,4-Dihydroxyphenyl)-a-L-alaninebiospider
b-(3,4-Dihydroxyphenyl)-L-alaninebiospider
b-(3,4-Dihydroxyphenyl)alanineGenerator
Bendopadb_source
beta-(3,4-Dihydroxyphenyl)-alpha-L-alanineHMDB
beta-(3,4-Dihydroxyphenyl)-L-alanineChEBI
beta-(3,4-Dihydroxyphenyl)alanineChEBI
Cidandopabiospider
Dihydroxy-L-phenylalaninebiospider
DihydroxyphenylalanineHMDB
DOPAbiospider
Dopaflexbiospider
Dopaidanbiospider
Dopalbiospider
Dopalinabiospider
Dopardb_source
Doparkinebiospider
Doparlbiospider
Dopasolbiospider
Dopastonbiospider
DopastoneHMDB
Dopastralbiospider
Dopicarbiospider
Doprinbiospider
Eldopalbiospider
Eldoparbiospider
Eldopatecbiospider
Eurodopabiospider
Helfo-dopabiospider
Insulaminabiospider
L-(-)-DOPAbiospider
L-(3, 4-Dihydroxyphenyl)alaninebiospider
L-(3,4-Dihydroxyphenyl)-α-alaninebiospider
L-(3,4-Dihydroxyphenyl)alaninebiospider
L-β-(3,4-Dihydroxyphenyl)alaninebiospider
L-3-(3,4-dihydroxyphenyl)-Alaninebiospider
L-3-(3,4-Dihydroxyphenyl)alaninebiospider
L-3-Hydroxytyrosinebiospider
L-4-5-Dihydroxyphenylalaninebiospider
L-b-(3,4-Dihydroxyphenyl)-a-alanineHMDB
L-b-(3,4-Dihydroxyphenyl)alanineGenerator
L-beta-(3,4-Dihydroxyphenyl)-alpha-alanineHMDB
L-beta-(3,4-Dihydroxyphenyl)alanineChEBI
L-dihydroxyphenylalaninebiospider
L-DOPAbiospider
L-Tyrosine, 3-hydroxy-biospider
L-β-(3,4-dihydroxyphenyl)alanineGenerator
Laradopabiospider
Larodopadb_source
Ledopabiospider
LevedopaHMDB
LevodopaChEBI
Levodopa, BAN, INN, JAN, USANdb_source
LevodopumChEBI
Levopadb_source
Maipedopabiospider
Pardabiospider
Pardopabiospider
ProdopaHMDB
Syndopabiospider
Veldopadb_source
Weldopabiospider
β-(3,4-dihydroxyphenyl)-L-alanineGenerator
β-(3,4-dihydroxyphenyl)alanineGenerator
Chemical FormulaC9H11NO4
IUPAC name(2S)-2-amino-3-(3,4-dihydroxyphenyl)propanoic acid
InChI IdentifierInChI=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
Isomeric SMILESN[C@@H](CC1=CC(O)=C(O)C=C1)C(O)=O
Average Molecular Weight197.1879
Monoisotopic Molecular Weight197.068807845
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
  • 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 FrameworkAromatic homomonocyclic compounds
External Descriptors
Physico-Chemical Properties - Experimental
PropertyValueReference
Experimental logP-2.39SANGSTER (1993)
Experimental Water Solubility5 mg/mL at 20 oCYALKOWSKY,SH & DANNENFELSER,RM (1992)
Melting PointMp 285.5° dec.DFC
Foods of Origin
FoodContent Range AverageReference
FoodReference
Production Data
Production Methodcommercial
Production Method ReferenceNot Available
Production Method Reference FileNot Available
Quantity AvailableProduction upon request, up to 2 g
Delivery TimeNot Available
Storage Formsolid
Storage Conditions-80°C
StabilityNot Available
PurityNot Available
Spectra
Spectral Data Upon RequestNot Available
Provider Information
Contact NameContact InstitutionContact Email
Rosa Vazquez Fresnovazquezf@ualberta.ca
Commercial Vendors
AKSci H813
AKSci J10404
AKSci J90768
Cayman Chemical 13248
Cayman Chemical HMDB0000181
Glentham GM9724
MetaSci HMDB0000181
Toronto Research Chemicals D533751