MiMeDB: Showing metabocard for L-Dopa (MMDBc0000498)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2020-12-10 18:39:08 UTC

Update Date

2024-10-09 19:16:51 UTC

Metabolite ID

MMDBc0000498

Metabolite Identification

Common Name

L-Dopa

Description

L-DOPA, also known as levodopa or 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). 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. The Swedish scientist Arvid Carlsson first showed in the 1950s that administering L-DOPA to animals with drug-induced (reserpine) Parkinsonian symptoms caused a reduction in the intensity of the animals' symptoms. 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. As a result, L-DOPA is a drug that is now used for the treatment of Parkinsonian disorders and DOPA-Responsive Dystonia. It is usually given with agents that inhibit its conversion to dopamine outside of the central nervous system. It is standard clinical practice in treating Parkinsonism 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. Side effects of L-DOPA treatment may include: hypertension, arrhythmias, nausea, gastrointestinal bleeding, disturbed respiration, hair loss, disorientation and confusion. L-DOPA can act as an L-tyrosine mimetic and be incorporated into proteins by mammalian cells in place of L-tyrosine, generating protease-resistant and aggregate-prone proteins in vitro and may contribute to neurotoxicity with chronic L-DOPA administration. L-phenylalanine, L-tyrosine, and L-DOPA are all precursors to the biological pigment melanin. The enzyme tyrosinase catalyzes the oxidation of L-DOPA to the reactive intermediate dopaquinone, which reacts further, eventually leading to melanin oligomers.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI


  Mrv1652309032023562D          

 14 14  0  0  1  0            999 V2000
   -0.7145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5722    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4290   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
 12  2  1  0  0  0  0
 10  3  1  0  0  0  0
  4  3  1  0  0  0  0
  1  5  1  0  0  0  0
  5  3  2  0  0  0  0
  2 13  1  0  0  0  0
 13  4  2  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
 11  6  1  0  0  0  0
  8  9  1  1  0  0  0
  8 10  1  0  0  0  0
 13 14  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0000498

> <DATABASE_NAME>
MIME

> <SMILES>
N[C@@H](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)/t6-/m0/s1

> <INCHI_KEY>
WTDRDQBEARUVNC-LURJTMIESA-N

> <FORMULA>
C9H11NO4

> <MOLECULAR_WEIGHT>
197.1879

> <EXACT_MASS>
197.068807845

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
25

> <JCHEM_AVERAGE_POLARIZABILITY>
18.90987044668941

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-2-amino-3-(3,4-dihydroxyphenyl)propanoic acid

> <JCHEM_LOGP>
-1.7921814507627933

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.686049362161093

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.650696949850563

> <JCHEM_PKA_STRONGEST_BASIC>
9.055027392905787

> <JCHEM_POLAR_SURFACE_AREA>
103.77999999999999

> <JCHEM_REFRACTIVITY>
49.07810000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
levodopa

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 03-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-SEP-20         0                                  
HETATM    1  C   UNK     0      -1.334   0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334   0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       5.335   3.080   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       4.001   0.770   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0       4.001  -0.770   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       6.668   0.770   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      -2.667  -1.540   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       0.000  -1.540   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
CONECT    1    2    5                                                       
CONECT    2    1   12   13                                                  
CONECT    3   10    4    5                                                  
CONECT    4    3   13                                                       
CONECT    5    1    3                                                       
CONECT    6    7    8   11                                                  
CONECT    7    6                                                            
CONECT    8    6    9   10                                                  
CONECT    9    8                                                            
CONECT   10    3    8                                                       
CONECT   11    6                                                            
CONECT   12    2                                                            
CONECT   13    2    4   14                                                  
CONECT   14   13                                                            
MASTER        0    0    0    0    0    0    0    0   14    0   28    0
END

Synonyms

Value	Source
(-)-3-(3,4-Dihydroxyphenyl)-L-alanine	ChEBI
(-)-Dopa	ChEBI
3,4-Dihydroxy-L-phenylalanine	ChEBI
3,4-DIHYDROXYPHENYLALANINE	ChEBI
3-Hydroxy-L-tyrosine	ChEBI
beta-(3,4-Dihydroxyphenyl)-L-alanine	ChEBI
beta-(3,4-Dihydroxyphenyl)alanine	ChEBI
Dihydroxy-L-phenylalanine	ChEBI
Dopar	ChEBI
L-beta-(3,4-Dihydroxyphenyl)alanine	ChEBI
Levodopa	ChEBI
Levodopum	ChEBI
b-(3,4-Dihydroxyphenyl)-L-alanine	Generator
Β-(3,4-dihydroxyphenyl)-L-alanine	Generator
b-(3,4-Dihydroxyphenyl)alanine	Generator
Β-(3,4-dihydroxyphenyl)alanine	Generator
L-b-(3,4-Dihydroxyphenyl)alanine	Generator
L-Β-(3,4-dihydroxyphenyl)alanine	Generator
(2S)-2-Amino-3-(3,4-dihydroxyphenyl)propanoate	HMDB
(2S)-2-Amino-3-(3,4-dihydroxyphenyl)propanoic acid	HMDB
3,4-Dihydroxyphenyl-L-alanine	HMDB
3-(3,4-Dihydroxyphenyl)-L-alanine	HMDB
b-(3,4-Dihydroxyphenyl)-a-L-alanine	HMDB
Bendopa	HMDB
beta-(3,4-Dihydroxyphenyl)-alpha-L-alanine	HMDB
Cidandopa	HMDB
Dihydroxyphenylalanine	HMDB
Dopaflex	HMDB
Dopaidan	HMDB
Dopal	HMDB
Dopalina	HMDB
Doparkine	HMDB
Doparl	HMDB
Dopasol	HMDB
Dopaston	HMDB
Dopastone	HMDB
Dopastral	HMDB
Dopicar	HMDB
Doprin	HMDB
Eldopal	HMDB
Eldopar	HMDB
Eldopatec	HMDB
Eurodopa	HMDB
Helfo-dopa	HMDB
Insulamina	HMDB
L-(-)-Dopa	HMDB
L-3-(3,4-Dihydroxyphenyl)-alanine	HMDB
L-4-5-Dihydroxyphenylalanine	HMDB
L-b-(3,4-Dihydroxyphenyl)-a-alanine	HMDB
L-beta-(3,4-Dihydroxyphenyl)-alpha-alanine	HMDB
L-Dihydroxyphenylalanine	HMDB
Laradopa	HMDB
Larodopa	HMDB
Ledopa	HMDB
Levedopa	HMDB
Levopa	HMDB
Maipedopa	HMDB
Parda	HMDB
Pardopa	HMDB
Prodopa	HMDB
Syndopa	HMDB
Veldopa	HMDB
Weldopa	HMDB
3 Hydroxy L tyrosine	HMDB
Roche brand OF levodopa	HMDB
L 3,4 Dihydroxyphenylalanine	HMDB
L-3,4-Dihydroxyphenylalanine	HMDB
Medphano brand OF levodopa	HMDB
L Dopa	HMDB
Roberts brand OF levodopa	HMDB

Molecular Formula

C₉H₁₁NO₄

Average Mass

197.1879

Monoisotopic Mass

197.068807845

IUPAC Name

(2S)-2-amino-3-(3,4-dihydroxyphenyl)propanoic acid

Traditional Name

levodopa

CAS Registry Number

Not Available

SMILES

N[C@@H](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)/t6-/m0/s1

InChI Key

WTDRDQBEARUVNC-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.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Tyrosine 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 Framework

Aromatic homomonocyclic compounds

External Descriptors

non-proteinogenic L-alpha-amino acid (CHEBI:15765 )
L-tyrosine derivative (CHEBI:15765 )
dopa (CHEBI:15765 )
Other amino acids (C00355 )
Biogenic amines (C00355 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
logP	-1.8	ChemAxon
pKa (Strongest Acidic)	1.65	ChemAxon
pKa (Strongest Basic)	9.06	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	103.78 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	49.08 m³·mol⁻¹	ChemAxon
Polarizability	18.91 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Not Available

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

Biospecimen Locations

Adrenal Medulla
Bladder
Blood
Brain
Cerebrospinal Fluid (CSF)
Epidermis
Feces
Intestine
Neuron
Placenta
Platelet
Skeletal Muscle
Urine

Tissue Locations

Adrenal Medulla
Bladder
Brain
Epidermis
Intestine
Neuron
Placenta
Platelet
Skeletal Muscle

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species
MMDBp0191760	Tyrosinase	Unknown	P14679	Homo sapiens
MMDBp0191942	Catechol O-methyltransferase	Unknown	P21964	Homo sapiens
MMDBp0191943	Tyrosine 3-monooxygenase	Enzyme	P07101	Homo sapiens
MMDBp0191948	Aromatic-L-amino-acid decarboxylase	Enzyme	P20711	Homo sapiens
MMDBp0193103	Cytochrome P450 2D6	Unknown	P10635	Homo sapiens
MMDBp0193233	D(2) dopamine receptor	Enzyme	P14416	Homo sapiens
MMDBp0193569	D(4) dopamine receptor	Enzyme	P21917	Homo sapiens
MMDBp0193661	Solute carrier family 15 member 1	Transporter	P46059	Homo sapiens
MMDBp0193808	4F2 cell-surface antigen heavy chain	Unknown	P08195	Homo sapiens
MMDBp0194001	Monocarboxylate transporter 10	Transporter	Q8TF71	Homo sapiens
MMDBp0196353	D(3) dopamine receptor	Unknown	P35462	Homo sapiens
MMDBp0196354	D(1A) dopamine receptor	Unknown	P21728	Homo sapiens
MMDBp0196359	D(1B) dopamine receptor	Unknown	P21918	Homo sapiens

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference
Alzheimer's disease		Association	Human Blood	HMDB	17031479
Aromatic l-amino acid decarboxylase deficiency	Increased	Association	Human Urine	HMDB	9686366
Sepiapterin reductase deficiency		Association	Human Cerebrospinal Fluid (CSF)	HMDB	18502672
Eosinophilic esophagitis		Association	Human Urine	HMDB	Slae, M., Huynh, H., Wishart, D.S. (2014). Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work)

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Archaea	Euryarchaeota	1	Human feces	Indirect association between microbiota composition and metabolites measured in host biospecimen
Bacteria/Eubacteria	Bacteroidetes	7	Human feces; Human stool	Indirect association between microbiota composition and metabolites measured in host biospecimen; Metabolic reconstruction
Bacteria/Eubacteria	Firmicutes	94	Human feces; Human stool; Pig ; Human ; Cattle	Indirect association between microbiota composition and metabolites measured in host biospecimen; Metabolic reconstruction
Bacteria/Eubacteria	Proteobacteria	198	Human feces; Human sputum; Human ; Human unknown; Pig ; Human pleural fluid plaque; Human dental plaque; Human nasal swab	Metabolic reconstruction
Bacteria/Eubacteria	Actinobacteria	80	Human feces; Human ; Human supragingival plaque	Metabolic reconstruction
Bacteria	Proteobacteria	11	Human feces; Human sputum; Human ; Human unknown; Pig ; Human pleural fluid plaque; Human dental plaque; Human nasal swab	Metabolic reconstruction
Archaea	Euryarchaeota	2		Metabolic reconstruction
Bacteria/Eubacteria	Fusobacteria	2	Human ; Human feces	Metabolic reconstruction
Bacteria	Actinobacteria	10	Human feces; Human ; Human supragingival plaque	Metabolic reconstruction
Bacteria/Eubacteria	Planctomycetes	2	Human feces	Metabolic reconstruction
Bacteria	Firmicutes	1	Human feces; Human stool; Pig ; Human ; Cattle	Indirect association between microbiota composition and metabolites measured in host biospecimen; Metabolic reconstruction
Eukaryota/Fungi	Basidiomycota	2	Human feces
Eukaryota/Fungi	Ascomycota	5	Human feces

Exposure Sources

Food Exposures

Other Exposures

Source Type	Data Source	Reference
Drugs	U.S. Environmental Protection Agency	CompTox
Drugs - Antimicrobial	U.S. Environmental Protection Agency	CompTox
Cosmetics	U.S. Environmental Protection Agency	CompTox
Domestics	U.S. Environmental Protection Agency	CompTox
Cosmetics	U.S. Environmental Protection Agency	CompTox

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected but not Quantified									HMDB
Human Blood	Detected and Quantified	14.0	2.53			uM	Elderly (>65 years old)	Both	Alzheimer's disease	HMDB	17031479
Human Urine	Detected and Quantified	8.683				umol/mmol creatinine	Children (1-13 years old)	Female	Aromatic L-amino acid decarboxylase deficiency	HMDB	9686366
Human Urine	Detected and Quantified	11.38				umol/mmol creatinine	Infant (0-1 year old)	Female	Aromatic L-amino acid decarboxylase deficiency	HMDB	9686366
Human Cerebrospinal fluid (csf)	Detected and Quantified	<0.001				uM	Children (1-13 years old)	Male	sepiapterin reductase deficiency	HMDB	18502672
Human Cerebrospinal fluid (csf)	Detected and Quantified	<0.025				uM	Children (1-13 years old)	Male	Normal	HMDB	18502672
Human Cerebrospinal fluid (csf)	Detected and Quantified	0.0035	0.0009			uM	Adult (>18 years old)	Not Specified	Normal	HMDB	3127089
Human Urine	Detected and Quantified			0.00500	0.217	umol/mmol creatinine	Children (1-13 years old)	Female	Normal	HMDB	9686366
Human Urine	Detected and Quantified			0.01	0.15	umol/mmol creatinine	Newborn (0-30 days old)	Both	Normal	HMDB	32340350
Human Urine	Detected and Quantified	0.02		0.01	0.04	umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	24023812
Human Urine	Detected and Quantified	0.04		0.01	0.08	umol/mmol creatinine	Newborn (0-30 days old)	Female	Normal	HMDB	32340350
Human Urine	Detected and Quantified	0.04		0.02	0.17	umol/mmol creatinine	Newborn (0-30 days old)	Male	Normal	HMDB	32340350
Human Urine	Detected and Quantified	0.094	0.0546			umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Eosinophilic esophagitis	HMDB	Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work)
Human Urine	Detected and Quantified	0.0833	0.0238			umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Normal	HMDB	Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work)
Human Blood	Detected and Quantified	0.00723	0.00097			uM	Adult (>18 years old)	Both	Normal	HMDB	Geigy Scientific Tables, 8th Rev edition, pp. 130. Edited by C. Lentner, West Cadwell, N.J.: Medical education Div., Ciba-Geigy Corp. Basel, Switzerland c1981-1992.
Human Urine	Detected and Quantified	0.008		0.0036	0.0138	umol/mmol creatinine	Children (1-13 years old)	Both	Normal	HMDB	Geigy Scientific Tables, 8th Rev edition, pp. 130. Edited by C. Lentner, West Cadwell, N.J.: Medical education Div., Ciba-Geigy Corp. Basel, Switzerland c1981-1992.
Human Urine	Detected and Quantified	0.0136	0.0033			umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	Geigy Scientific Tables, 8th Rev edition, pp. 130. Edited by C. Lentner, West Cadwell, N.J.: Medical education Div., Ciba-Geigy Corp. Basel, Switzerland c1981-1992.
Human Adrenal medulla	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Bladder	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Brain	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Epidermis	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Intestine	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Neuron	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Placenta	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Platelet	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Skeletal muscle	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	29808030
Human Urine	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	32966057
Human Blood	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	32966057

External Links

HMDB ID

HMDB0000181

DrugBank ID

DB01235

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

L-DIHYDROXY-PHENYLALANINE

BiGG ID

34719

Wikipedia Link

Levodopa

METLIN ID

PubChem Compound

6047

PDB ID

Not Available

ChEBI ID

15765

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Hyland K, Clayton PT: Aromatic L-amino acid decarboxylase deficiency: diagnostic methodology. Clin Chem. 1992 Dec;38(12):2405-10. [PubMed:1281049 ]
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. doi: 10.18926/AMO/32193. [PubMed:1755339 ]
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. doi: 10.1016/S0065-1281(11)80247-3. [PubMed:2113342 ]
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. doi: 10.1016/0009-8981(88)90290-2. [PubMed:3127089 ]
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 ]
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 ]
Streifler M, Avrami E, Rabey JM: L-dopa and the secretion of sebum in Parkinsonian patients. Eur Neurol. 1980;19(1):43-8. doi: 10.1159/000115127. [PubMed:7371653 ]
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. doi: 10.1046/j.1471-4159.1995.64062810.x. [PubMed:7760062 ]
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 ]
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. doi: 10.1016/s0006-8993(00)02758-x. [PubMed:11011012 ]
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. doi: 10.1016/s0960-894x(01)00140-8. [PubMed:11327596 ]
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. doi: 10.1124/jpet.103.049270. Epub 2003 Mar 20. [PubMed:12649306 ]
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. doi: 10.1620/tjem.199.149. [PubMed:12703659 ]
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 (Vienna). 2003 Aug;110(8):899-910. doi: 10.1007/s00702-003-0001-2. [PubMed:12898345 ]
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 (Vienna). 2003 Aug;110(8):911-22. doi: 10.1007/s00702-003-0004-z. [PubMed:12898346 ]
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. doi: 10.1111/j.1523-1755.2004.00722.x. [PubMed:15200428 ]
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 ]
Cools R: Dopaminergic modulation of cognitive function-implications for L-DOPA treatment in Parkinson's disease. Neurosci Biobehav Rev. 2006;30(1):1-23. doi: 10.1016/j.neubiorev.2005.03.024. Epub 2005 Jun 1. [PubMed:15935475 ]
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. doi: 10.1016/j.tips.2005.05.002. [PubMed:15936832 ]
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. doi: 10.1007/s11064-005-2752-7. [PubMed:16176068 ]

Showing metabocard for L-Dopa (MMDBc0000498)

MOL for #<Metabolite:0x00007f925156b068>

3D MOL for #<Metabolite:0x00007f925156b068>

3D SDF for #<Metabolite:0x00007f925156b068>

3D-SDF for #<Metabolite:0x00007f925156b068>

PDB for #<Metabolite:0x00007f925156b068>

3D PDB for #<Metabolite:0x00007f925156b068>

SMILES for #<Metabolite:0x00007f925156b068>

INCHI for #<Metabolite:0x00007f925156b068>

Structure for #<Metabolite:0x00007f925156b068>

3D Structure for #<Metabolite:0x00007f925156b068>