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Record Information
Version1.0
Creation Date2016-09-30 22:20:35 UTC
Update Date2020-05-20 23:10:21 UTC
BMDB IDBMDB0000181
Secondary Accession Numbers
  • BMDB00181
Metabolite Identification
Common NameL-Dopa
DescriptionL-Dopa, also known as l-dopa or l-dopa, 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 drug which is used for the treatment of idiopathic parkinson's disease (paralysis agitans), postencephalitic parkinsonism, symptomatic parkinsonism which may follow injury to the nervous system by carbon monoxide intoxication, and manganese intoxication. L-Dopa exists as a solid, possibly soluble (in water), and a very strong basic compound (based on its pKa) molecule. L-Dopa exists in all living organisms, ranging from bacteria to humans. L-Dopa participates in a number of enzymatic reactions, within cattle. In particular, L-Dopa and tetrahydrobiopterin can be converted into dopamine and 4a-hydroxytetrahydrobiopterin through the action of the enzyme aromatic-L-amino-acid decarboxylase. In addition, L-Dopa can be converted into dopaquinone through its interaction with the enzyme tyrosinase. In cattle, L-dopa is involved in the metabolic pathway called the tyrosine metabolism pathway. L-Dopa is a potentially toxic compound.
Structure
Thumb
Synonyms
ValueSource
(-)-3-(3,4-Dihydroxyphenyl)-L-alanineChEBI
(-)-DopaChEBI
3,4-Dihydroxy-L-phenylalanineChEBI
3,4-DIHYDROXYPHENYLALANINEChEBI
3-Hydroxy-L-tyrosineChEBI
beta-(3,4-Dihydroxyphenyl)-L-alanineChEBI
beta-(3,4-Dihydroxyphenyl)alanineChEBI
Dihydroxy-L-phenylalanineChEBI
DoparChEBI
L-beta-(3,4-Dihydroxyphenyl)alanineChEBI
LevodopaChEBI
LevodopumChEBI
b-(3,4-Dihydroxyphenyl)-L-alanineGenerator
Β-(3,4-dihydroxyphenyl)-L-alanineGenerator
b-(3,4-Dihydroxyphenyl)alanineGenerator
Β-(3,4-dihydroxyphenyl)alanineGenerator
L-b-(3,4-Dihydroxyphenyl)alanineGenerator
L-Β-(3,4-dihydroxyphenyl)alanineGenerator
(2S)-2-Amino-3-(3,4-dihydroxyphenyl)propanoateHMDB
(2S)-2-Amino-3-(3,4-dihydroxyphenyl)propanoic acidHMDB
3,4-Dihydroxyphenyl-L-alanineHMDB
3-(3,4-Dihydroxyphenyl)-L-alanineHMDB
b-(3,4-Dihydroxyphenyl)-a-L-alanineHMDB
BendopaHMDB
beta-(3,4-Dihydroxyphenyl)-alpha-L-alanineHMDB
CidandopaHMDB
DihydroxyphenylalanineHMDB
DopaflexHMDB
DopaidanHMDB
DopalHMDB
DopalinaHMDB
DoparkineHMDB
DoparlHMDB
DopasolHMDB
DopastonHMDB
DopastoneHMDB
DopastralHMDB
DopicarHMDB
DoprinHMDB
EldopalHMDB
EldoparHMDB
EldopatecHMDB
EurodopaHMDB
Helfo-dopaHMDB
InsulaminaHMDB
L-(-)-DopaHMDB
L-3-(3,4-Dihydroxyphenyl)-alanineHMDB
L-4-5-DihydroxyphenylalanineHMDB
L-b-(3,4-Dihydroxyphenyl)-a-alanineHMDB
L-beta-(3,4-Dihydroxyphenyl)-alpha-alanineHMDB
L-DihydroxyphenylalanineHMDB
LaradopaHMDB
LarodopaHMDB
LedopaHMDB
LevedopaHMDB
LevopaHMDB
MaipedopaHMDB
PardaHMDB
PardopaHMDB
ProdopaHMDB
SyndopaHMDB
VeldopaHMDB
WeldopaHMDB
3 Hydroxy L tyrosineHMDB
Roche brand OF levodopaHMDB
L 3,4 DihydroxyphenylalanineHMDB
L-3,4-DihydroxyphenylalanineHMDB
Medphano brand OF levodopaHMDB
L DopaHMDB
Roberts brand OF levodopaHMDB
Chemical FormulaC9H11NO4
Average Molecular Weight197.1879
Monoisotopic Molecular Weight197.068807845
IUPAC NameNot Available
Traditional NameNot Available
CAS Registry Number59-92-7
SMILESNot Available
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
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
Ontology
StatusDetected but not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm
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 PropertiesNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Adrenal Medulla
  • Bladder
  • Brain
  • Epidermis
  • Intestine
  • Liver
  • Neuron
  • Placenta
  • Platelet
  • Skeletal Muscle
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
Adrenal MedullaExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
BladderExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
BrainExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
EpidermisExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
IntestineExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
LiverDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
LiverDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
NeuronExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
PlacentaExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
PlateletExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
Skeletal MuscleExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
Abnormal Concentrations
Not Available
HMDB IDHMDB0000181
DrugBank IDDB01235
Phenol Explorer Compound IDNot Available
FooDB IDFDB000567
KNApSAcK IDC00001357
Chemspider ID5824
KEGG Compound IDC00355
BioCyc IDL-DIHYDROXY-PHENYLALANINE
BiGG ID34719
Wikipedia LinkLevodopa
METLIN ID42
PubChem Compound6047
PDB IDNot Available
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 ReferencesNot Available

Enzymes

General function:
Amino acid transport and metabolism
Specific function:
Plays an important role in the physiology of adrenergic neurons.
Gene Name:
TH
Uniprot ID:
P17289
Molecular weight:
55123.0
General function:
Involved in copper ion binding
Specific function:
This is a copper-containing oxidase that functions in the formation of pigments such as melanins and other polyphenolic compounds. Catalyzes the initial and rate limiting step in the cascade of reactions leading to melanin production from tyrosine. In addition to hydroxylating tyrosine to DOPA (3,4-dihydroxyphenylalanine), also catalyzes the oxidation of DOPA to DOPA-quinone, and possibly the oxidation of DHI (5,6-dihydroxyindole) to indole-5,6 quinone.
Gene Name:
TYR
Uniprot ID:
Q8MIU0
Molecular weight:
60304.0
Reactions
2 L-Dopa + Oxygen →2 Dopaquinone +2 Waterdetails
Tyramine + Oxygen → L-Dopa + Waterdetails
General function:
Amino acid transport and metabolism
Specific function:
Catalyzes the decarboxylation of L-3,4-dihydroxyphenylalanine (DOPA) to dopamine, L-5-hydroxytryptophan to serotonin and L-tryptophan to tryptamine.
Gene Name:
DDC
Uniprot ID:
P27718
Molecular weight:
54294.0