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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2023-07-07 20:53:56 UTC
HMDB IDHMDB0000181
Secondary Accession Numbers
  • HMDB00181
Metabolite Identification
Common NameDOPA
DescriptionL-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
Data?1676999675
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 Name(2S)-2-amino-3-(3,4-dihydroxyphenyl)propanoic acid
Traditional Namelevodopa
CAS Registry Number59-92-7
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 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
Physiological effect
Disposition
Biological locationRoute of exposureSource
Process
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point285 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility5 mg/mLNot Available
LogP-2.39SANGSTER (1993)
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M-H]-Not Available140.3http://allccs.zhulab.cn/database/detail?ID=AllCCS00000007
[M+H]+Not Available147.1http://allccs.zhulab.cn/database/detail?ID=AllCCS00000007
Predicted Molecular Properties
PropertyValueSource
Water Solubility3.3 g/LALOGPS
logP-1.8ChemAxon
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
Polarizability18.91 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+146.42531661259
DarkChem[M-H]-142.58231661259
AllCCS[M+H]+143.99532859911
AllCCS[M-H]-141.18532859911
DeepCCS[M+H]+142.1730932474
DeepCCS[M-H]-139.77430932474
DeepCCS[M-2H]-173.82330932474
DeepCCS[M+Na]+148.43330932474
AllCCS[M+H]+144.032859911
AllCCS[M+H-H2O]+140.032859911
AllCCS[M+NH4]+147.832859911
AllCCS[M+Na]+148.832859911
AllCCS[M-H]-141.232859911
AllCCS[M+Na-2H]-141.832859911
AllCCS[M+HCOO]-142.632859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
L-DopaN[C@@H](CC1=CC=C(O)C(O)=C1)C(O)=O3369.5Standard polar33892256
L-DopaN[C@@H](CC1=CC=C(O)C(O)=C1)C(O)=O2121.4Standard non polar33892256
L-DopaN[C@@H](CC1=CC=C(O)C(O)=C1)C(O)=O2029.5Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
L-Dopa,1TMS,isomer #1C[Si](C)(C)OC1=CC=C(C[C@H](N)C(=O)O)C=C1O2078.4Semi standard non polar33892256
L-Dopa,1TMS,isomer #2C[Si](C)(C)OC1=CC(C[C@H](N)C(=O)O)=CC=C1O2081.8Semi standard non polar33892256
L-Dopa,1TMS,isomer #3C[Si](C)(C)OC(=O)[C@@H](N)CC1=CC=C(O)C(O)=C12090.3Semi standard non polar33892256
L-Dopa,1TMS,isomer #4C[Si](C)(C)N[C@@H](CC1=CC=C(O)C(O)=C1)C(=O)O2168.5Semi standard non polar33892256
L-Dopa,2TMS,isomer #1C[Si](C)(C)OC(=O)[C@@H](N)CC1=CC=C(O[Si](C)(C)C)C(O)=C12016.4Semi standard non polar33892256
L-Dopa,2TMS,isomer #2C[Si](C)(C)OC1=CC=C(C[C@H](N)C(=O)O)C=C1O[Si](C)(C)C2078.3Semi standard non polar33892256
L-Dopa,2TMS,isomer #3C[Si](C)(C)N[C@@H](CC1=CC=C(O[Si](C)(C)C)C(O)=C1)C(=O)O2110.6Semi standard non polar33892256
L-Dopa,2TMS,isomer #4C[Si](C)(C)OC(=O)[C@@H](N)CC1=CC=C(O)C(O[Si](C)(C)C)=C12020.1Semi standard non polar33892256
L-Dopa,2TMS,isomer #5C[Si](C)(C)N[C@@H](CC1=CC=C(O)C(O[Si](C)(C)C)=C1)C(=O)O2109.7Semi standard non polar33892256
L-Dopa,2TMS,isomer #6C[Si](C)(C)N[C@@H](CC1=CC=C(O)C(O)=C1)C(=O)O[Si](C)(C)C2113.0Semi standard non polar33892256
L-Dopa,2TMS,isomer #7C[Si](C)(C)N([C@@H](CC1=CC=C(O)C(O)=C1)C(=O)O)[Si](C)(C)C2300.0Semi standard non polar33892256
L-Dopa,3TMS,isomer #1C[Si](C)(C)OC(=O)[C@@H](N)CC1=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C12054.8Semi standard non polar33892256
L-Dopa,3TMS,isomer #2C[Si](C)(C)N[C@@H](CC1=CC=C(O[Si](C)(C)C)C(O)=C1)C(=O)O[Si](C)(C)C2067.8Semi standard non polar33892256
L-Dopa,3TMS,isomer #3C[Si](C)(C)N[C@@H](CC1=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C1)C(=O)O2106.7Semi standard non polar33892256
L-Dopa,3TMS,isomer #4C[Si](C)(C)OC1=CC=C(C[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)C=C1O2248.2Semi standard non polar33892256
L-Dopa,3TMS,isomer #5C[Si](C)(C)N[C@@H](CC1=CC=C(O)C(O[Si](C)(C)C)=C1)C(=O)O[Si](C)(C)C2047.1Semi standard non polar33892256
L-Dopa,3TMS,isomer #6C[Si](C)(C)OC1=CC(C[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)=CC=C1O2240.2Semi standard non polar33892256
L-Dopa,3TMS,isomer #7C[Si](C)(C)OC(=O)[C@H](CC1=CC=C(O)C(O)=C1)N([Si](C)(C)C)[Si](C)(C)C2262.9Semi standard non polar33892256
L-Dopa,4TMS,isomer #1C[Si](C)(C)N[C@@H](CC1=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C1)C(=O)O[Si](C)(C)C2108.8Semi standard non polar33892256
L-Dopa,4TMS,isomer #1C[Si](C)(C)N[C@@H](CC1=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C1)C(=O)O[Si](C)(C)C2133.4Standard non polar33892256
L-Dopa,4TMS,isomer #1C[Si](C)(C)N[C@@H](CC1=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C1)C(=O)O[Si](C)(C)C2175.1Standard polar33892256
L-Dopa,4TMS,isomer #2C[Si](C)(C)OC(=O)[C@H](CC1=CC=C(O[Si](C)(C)C)C(O)=C1)N([Si](C)(C)C)[Si](C)(C)C2257.1Semi standard non polar33892256
L-Dopa,4TMS,isomer #2C[Si](C)(C)OC(=O)[C@H](CC1=CC=C(O[Si](C)(C)C)C(O)=C1)N([Si](C)(C)C)[Si](C)(C)C2259.3Standard non polar33892256
L-Dopa,4TMS,isomer #2C[Si](C)(C)OC(=O)[C@H](CC1=CC=C(O[Si](C)(C)C)C(O)=C1)N([Si](C)(C)C)[Si](C)(C)C2277.6Standard polar33892256
L-Dopa,4TMS,isomer #3C[Si](C)(C)OC1=CC=C(C[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)C=C1O[Si](C)(C)C2271.0Semi standard non polar33892256
L-Dopa,4TMS,isomer #3C[Si](C)(C)OC1=CC=C(C[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)C=C1O[Si](C)(C)C2215.0Standard non polar33892256
L-Dopa,4TMS,isomer #3C[Si](C)(C)OC1=CC=C(C[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)C=C1O[Si](C)(C)C2314.0Standard polar33892256
L-Dopa,4TMS,isomer #4C[Si](C)(C)OC(=O)[C@H](CC1=CC=C(O)C(O[Si](C)(C)C)=C1)N([Si](C)(C)C)[Si](C)(C)C2250.3Semi standard non polar33892256
L-Dopa,4TMS,isomer #4C[Si](C)(C)OC(=O)[C@H](CC1=CC=C(O)C(O[Si](C)(C)C)=C1)N([Si](C)(C)C)[Si](C)(C)C2282.7Standard non polar33892256
L-Dopa,4TMS,isomer #4C[Si](C)(C)OC(=O)[C@H](CC1=CC=C(O)C(O[Si](C)(C)C)=C1)N([Si](C)(C)C)[Si](C)(C)C2326.3Standard polar33892256
L-Dopa,5TMS,isomer #1C[Si](C)(C)OC(=O)[C@H](CC1=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C1)N([Si](C)(C)C)[Si](C)(C)C2347.9Semi standard non polar33892256
L-Dopa,5TMS,isomer #1C[Si](C)(C)OC(=O)[C@H](CC1=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C1)N([Si](C)(C)C)[Si](C)(C)C2238.7Standard non polar33892256
L-Dopa,5TMS,isomer #1C[Si](C)(C)OC(=O)[C@H](CC1=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C1)N([Si](C)(C)C)[Si](C)(C)C2155.9Standard polar33892256
L-Dopa,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC=C(C[C@H](N)C(=O)O)C=C1O2337.1Semi standard non polar33892256
L-Dopa,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CC(C[C@H](N)C(=O)O)=CC=C1O2338.8Semi standard non polar33892256
L-Dopa,1TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC(=O)[C@@H](N)CC1=CC=C(O)C(O)=C12337.7Semi standard non polar33892256
L-Dopa,1TBDMS,isomer #4CC(C)(C)[Si](C)(C)N[C@@H](CC1=CC=C(O)C(O)=C1)C(=O)O2418.5Semi standard non polar33892256
L-Dopa,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)[C@@H](N)CC1=CC=C(O[Si](C)(C)C(C)(C)C)C(O)=C12555.0Semi standard non polar33892256
L-Dopa,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CC=C(C[C@H](N)C(=O)O)C=C1O[Si](C)(C)C(C)(C)C2582.0Semi standard non polar33892256
L-Dopa,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)N[C@@H](CC1=CC=C(O[Si](C)(C)C(C)(C)C)C(O)=C1)C(=O)O2645.6Semi standard non polar33892256
L-Dopa,2TBDMS,isomer #4CC(C)(C)[Si](C)(C)OC(=O)[C@@H](N)CC1=CC=C(O)C(O[Si](C)(C)C(C)(C)C)=C12517.0Semi standard non polar33892256
L-Dopa,2TBDMS,isomer #5CC(C)(C)[Si](C)(C)N[C@@H](CC1=CC=C(O)C(O[Si](C)(C)C(C)(C)C)=C1)C(=O)O2621.4Semi standard non polar33892256
L-Dopa,2TBDMS,isomer #6CC(C)(C)[Si](C)(C)N[C@@H](CC1=CC=C(O)C(O)=C1)C(=O)O[Si](C)(C)C(C)(C)C2583.1Semi standard non polar33892256
L-Dopa,2TBDMS,isomer #7CC(C)(C)[Si](C)(C)N([C@@H](CC1=CC=C(O)C(O)=C1)C(=O)O)[Si](C)(C)C(C)(C)C2725.3Semi standard non polar33892256
L-Dopa,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)[C@@H](N)CC1=CC=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C12751.1Semi standard non polar33892256
L-Dopa,3TBDMS,isomer #2CC(C)(C)[Si](C)(C)N[C@@H](CC1=CC=C(O[Si](C)(C)C(C)(C)C)C(O)=C1)C(=O)O[Si](C)(C)C(C)(C)C2803.0Semi standard non polar33892256
L-Dopa,3TBDMS,isomer #3CC(C)(C)[Si](C)(C)N[C@@H](CC1=CC=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C1)C(=O)O2854.5Semi standard non polar33892256
L-Dopa,3TBDMS,isomer #4CC(C)(C)[Si](C)(C)OC1=CC=C(C[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1O2996.0Semi standard non polar33892256
L-Dopa,3TBDMS,isomer #5CC(C)(C)[Si](C)(C)N[C@@H](CC1=CC=C(O)C(O[Si](C)(C)C(C)(C)C)=C1)C(=O)O[Si](C)(C)C(C)(C)C2767.2Semi standard non polar33892256
L-Dopa,3TBDMS,isomer #6CC(C)(C)[Si](C)(C)OC1=CC(C[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=CC=C1O2971.8Semi standard non polar33892256
L-Dopa,3TBDMS,isomer #7CC(C)(C)[Si](C)(C)OC(=O)[C@H](CC1=CC=C(O)C(O)=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2911.8Semi standard non polar33892256
L-Dopa,4TBDMS,isomer #1CC(C)(C)[Si](C)(C)N[C@@H](CC1=CC=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C1)C(=O)O[Si](C)(C)C(C)(C)C3007.9Semi standard non polar33892256
L-Dopa,4TBDMS,isomer #1CC(C)(C)[Si](C)(C)N[C@@H](CC1=CC=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C1)C(=O)O[Si](C)(C)C(C)(C)C2876.1Standard non polar33892256
L-Dopa,4TBDMS,isomer #1CC(C)(C)[Si](C)(C)N[C@@H](CC1=CC=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C1)C(=O)O[Si](C)(C)C(C)(C)C2659.6Standard polar33892256
L-Dopa,4TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=O)[C@H](CC1=CC=C(O[Si](C)(C)C(C)(C)C)C(O)=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3181.1Semi standard non polar33892256
L-Dopa,4TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=O)[C@H](CC1=CC=C(O[Si](C)(C)C(C)(C)C)C(O)=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3011.2Standard non polar33892256
L-Dopa,4TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=O)[C@H](CC1=CC=C(O[Si](C)(C)C(C)(C)C)C(O)=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2678.2Standard polar33892256
L-Dopa,4TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC1=CC=C(C[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1O[Si](C)(C)C(C)(C)C3214.9Semi standard non polar33892256
L-Dopa,4TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC1=CC=C(C[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1O[Si](C)(C)C(C)(C)C2942.8Standard non polar33892256
L-Dopa,4TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC1=CC=C(C[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1O[Si](C)(C)C(C)(C)C2695.7Standard polar33892256
L-Dopa,4TBDMS,isomer #4CC(C)(C)[Si](C)(C)OC(=O)[C@H](CC1=CC=C(O)C(O[Si](C)(C)C(C)(C)C)=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3150.8Semi standard non polar33892256
L-Dopa,4TBDMS,isomer #4CC(C)(C)[Si](C)(C)OC(=O)[C@H](CC1=CC=C(O)C(O[Si](C)(C)C(C)(C)C)=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3034.3Standard non polar33892256
L-Dopa,4TBDMS,isomer #4CC(C)(C)[Si](C)(C)OC(=O)[C@H](CC1=CC=C(O)C(O[Si](C)(C)C(C)(C)C)=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2715.4Standard polar33892256
L-Dopa,5TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)[C@H](CC1=CC=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3418.3Semi standard non polar33892256
L-Dopa,5TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)[C@H](CC1=CC=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3118.7Standard non polar33892256
L-Dopa,5TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)[C@H](CC1=CC=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2684.7Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - DOPA GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (4 TMS)splash10-014i-0790000000-b2f7f063a2c8197c7edd2014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - DOPA GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-014i-0690000000-622497b3104c6082a45d2014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - DOPA GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (4 TMS)splash10-00xr-9350000000-b0cc4636931d2de64d812014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - DOPA GC-MS (4 TMS)splash10-014i-0590000000-4474e81e4226bb4e1d4c2014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - DOPA GC-EI-TOF (Non-derivatized)splash10-014i-0790000000-b2f7f063a2c8197c7edd2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - DOPA GC-EI-TOF (Non-derivatized)splash10-014i-0690000000-622497b3104c6082a45d2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - DOPA GC-EI-TOF (Non-derivatized)splash10-00xr-9350000000-b0cc4636931d2de64d812017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - DOPA GC-MS (Non-derivatized)splash10-014i-0590000000-4474e81e4226bb4e1d4c2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - DOPA GC-EI-TOF (Non-derivatized)splash10-014i-1890000000-646d209fa1943582a3362017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - DOPA GC-EI-TOF (Non-derivatized)splash10-014i-0690000000-720ed87e98a0d9f1721d2017-09-12HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - DOPA GC-MS (Non-derivatized) - 70eV, Positivesplash10-0fk9-3900000000-266d9baeda773fe1fb222017-08-28Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - DOPA GC-MS (3 TMS) - 70eV, Positivesplash10-0002-4193000000-8c76bf85d8a897e9403c2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - DOPA GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - DOPA GC-MS (TMS_1_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - DOPA GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - DOPA GC-MS (TMS_1_3) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - DOPA GC-MS (TMS_1_4) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - DOPA GC-MS (TMS_2_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - DOPA GC-MS (TMS_2_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - DOPA GC-MS (TMS_2_3) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - DOPA GC-MS (TMS_2_4) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - DOPA GC-MS (TMS_2_5) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - DOPA GC-MS (TMS_2_6) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - DOPA GC-MS (TMS_2_7) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - DOPA GC-MS (TMS_3_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - DOPA Quattro_QQQ 10V, Positive-QTOF (Annotated)splash10-0uea-0900000000-8eb71aa0cc8622f097a22012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - DOPA Quattro_QQQ 25V, Positive-QTOF (Annotated)splash10-0a59-2900000000-bf63b9b719959b82b5432012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - DOPA Quattro_QQQ 40V, Positive-QTOF (Annotated)splash10-056r-9300000000-a78b0b31dd33fe8479a72012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - DOPA LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive-QTOFsplash10-0f6t-0911000000-15affa616923dfb9c45a2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - DOPA LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive-QTOFsplash10-000i-0900000000-22d8267801d0eb0b73c22012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - DOPA LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive-QTOFsplash10-001i-0900000000-2c310034a1a871502b4c2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - DOPA LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive-QTOFsplash10-0udi-0900000000-5e6020c952f741531fcb2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - DOPA LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive-QTOFsplash10-0007-0970100000-49594dae82ce73e734e62012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - DOPA LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive-QTOFsplash10-001i-0900000000-2183a68f58b951f3f1c72012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - DOPA LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive-QTOFsplash10-03di-0900000000-0030db588fbd92c5b7612012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - DOPA LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive-QTOFsplash10-0006-0090000000-544615463a975baae9e42012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - DOPA LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative-QTOFsplash10-0002-0729111000-0a20b01f58fff8ad7ef02012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - DOPA LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative-QTOFsplash10-004i-0900000000-c8095a31ed4b3dbbc6462012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - DOPA LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative-QTOFsplash10-03di-0190000000-41515cba3a69297218592012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - DOPA LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative-QTOFsplash10-0002-0900000000-8074c509ef5bae1129fc2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - DOPA LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative-QTOFsplash10-0006-0502193020-497bfad7ba247159ca002012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - DOPA LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative-QTOFsplash10-004i-0900000000-0b0d4b6dcb7f1fa24e1a2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - DOPA LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative-QTOFsplash10-004i-0029800000-05f40324c8c1fec7963a2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - DOPA LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative-QTOFsplash10-0006-0000090000-c0cd80185ce47b30e5fe2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - DOPA LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive-QTOFsplash10-0002-0900000000-df116b84981cf4a1371a2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - DOPA LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Positive-QTOFsplash10-0f6t-0900000000-1c1c39a8880442ea18df2012-08-31HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - DOPA 10V, Positive-QTOFsplash10-0udj-0900000000-cf54b26df05181b0d2fc2017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - DOPA 20V, Positive-QTOFsplash10-0udi-0900000000-d506f2673b114b8e38d22017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - DOPA 40V, Positive-QTOFsplash10-00di-8900000000-1699873cb7650f62b5bc2017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - DOPA 10V, Negative-QTOFsplash10-0002-0900000000-a0d81bfc4868b0d1cbf92017-07-26Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Experimental 1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)2012-12-04Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)2012-12-05Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-03FELIX labView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Feces
  • Urine
Tissue Locations
  • Adrenal Medulla
  • Bladder
  • Brain
  • Epidermis
  • Intestine
  • Neuron
  • Placenta
  • Platelet
  • Skeletal Muscle
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.00723 +/- 0.00097 uMAdult (>18 years old)BothNormal
    • Geigy Scientific ...
details
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified0.0035 +/- 0.0009 uMAdult (>18 years old)Not SpecifiedNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified<0.025 uMChildren (1-13 years old)MaleNormal details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified0.01-0.15 umol/mmol creatinineNewborn (0-30 days old)BothNormal details
UrineDetected and Quantified0.04(0.01-0.08) umol/mmol creatinineNewborn (0-30 days old)FemaleNormal details
UrineDetected and Quantified0.04(0.02-0.17) umol/mmol creatinineNewborn (0-30 days old)MaleNormal details
UrineDetected and Quantified0.0833 +/- 0.0238 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Normal
    • Analysis of 30 no...
details
UrineDetected and Quantified0.02 (0.01-0.04) umol/mmol creatinineAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified0.00500-0.217 umol/mmol creatinineChildren (1-13 years old)Female
Normal
details
UrineDetected and Quantified0.008 (0.0036-0.0138) umol/mmol creatinineChildren (1-13 years old)BothNormal
    • Geigy Scientific ...
    • West Cadwell, N.J...
    • Basel, Switzerlan...
details
UrineDetected and Quantified0.0136 +/- 0.0033 umol/mmol creatinineAdult (>18 years old)BothNormal
    • Geigy Scientific ...
    • West Cadwell, N.J...
    • Basel, Switzerlan...
details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified14.0 +/- 2.53 uMElderly (>65 years old)BothAlzheimer's disease details
Cerebrospinal Fluid (CSF)Detected and Quantified<0.001 uMChildren (1-13 years old)Malesepiapterin reductase deficiency details
UrineDetected and Quantified0.094 +/- 0.0546 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Eosinophilic esophagitis
    • Analysis of 30 no...
details
UrineDetected and Quantified0.1135 +/- 0.1355 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Gastroesophageal reflux disease
    • Analysis of 30 no...
details
UrineDetected and Quantified8.683 umol/mmol creatinineChildren (1-13 years old)Female
Aromatic L-amino acid decarboxylase deficiency
details
UrineDetected and Quantified11.38 umol/mmol creatinineInfant (0-1 year old)Female
Aromatic L-amino acid decarboxylase deficiency
details
Associated Disorders and Diseases
Disease References
Alzheimer's disease
  1. 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 ]
Sepiapterin reductase deficiency
  1. Verbeek MM, Willemsen MA, Wevers RA, Lagerwerf AJ, Abeling NG, Blau N, Thony B, Vargiami E, Zafeiriou DI: Two Greek siblings with sepiapterin reductase deficiency. Mol Genet Metab. 2008 Aug;94(4):403-9. doi: 10.1016/j.ymgme.2008.04.003. Epub 2008 May 27. [PubMed:18502672 ]
Eosinophilic esophagitis
  1. Slae, M., Huynh, H., Wishart, D.S. (2014). Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work). NA.
Aromatic L-amino acid decarboxylase deficiency
  1. Abeling NG, van Gennip AH, Barth PG, van Cruchten A, Westra M, Wijburg FA: Aromatic L-amino acid decarboxylase deficiency: a new case with a mild clinical presentation and unexpected laboratory findings. J Inherit Metab Dis. 1998 Jun;21(3):240-2. [PubMed:9686366 ]
Associated OMIM IDs
  • 104300 (Alzheimer's disease)
  • 182125 (Sepiapterin reductase deficiency)
  • 610247 (Eosinophilic esophagitis)
  • 608643 (Aromatic L-amino acid decarboxylase deficiency)
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
Food Biomarker OntologyNot Available
VMH ID34DHPHE
MarkerDB IDMDB00000086
Good Scents IDNot Available
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)Download (PDF)
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. 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 ]
  3. 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 ]
  4. 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 ]
  5. 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 ]
  6. 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 ]
  7. 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 ]
  8. 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. [PubMed:12898345 ]
  9. 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 ]
  10. 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 ]
  11. 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 ]
  12. 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 ]
  13. 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 ]
  14. Hyland K, Clayton PT: Aromatic L-amino acid decarboxylase deficiency: diagnostic methodology. Clin Chem. 1992 Dec;38(12):2405-10. [PubMed:1281049 ]
  15. 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 ]
  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 ]
  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 (Vienna). 2003 Aug;110(8):911-22. [PubMed:12898346 ]
  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 ]
  19. 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. [PubMed:11011012 ]
  20. 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. [PubMed:15200428 ]

Only showing the first 10 proteins. There are 13 proteins in total.

Enzymes

General function:
Involved in oxidoreductase activity
Specific function:
This is a copper-containing oxidase that functions in the formation of pigments such as melanins and other polyphenolic compounds. Catalyzes the rate-limiting conversions of tyrosine to DOPA, DOPA to DOPA-quinone and possibly 5,6-dihydroxyindole to indole-5,6 quinone.
Gene Name:
TYR
Uniprot ID:
P14679
Molecular weight:
60392.69
Reactions
DOPA + Oxygen → Dopaquinone + Waterdetails
L-Tyrosine + Oxygen → DOPA + Waterdetails
DOPA + L-Tyrosine + Oxygen → Dopaquinone + DOPA + Waterdetails
General function:
Involved in magnesium ion binding
Specific function:
Catalyzes the O-methylation, and thereby the inactivation, of catecholamine neurotransmitters and catechol hormones. Also shortens the biological half-lives of certain neuroactive drugs, like L-DOPA, alpha-methyl DOPA and isoproterenol.
Gene Name:
COMT
Uniprot ID:
P21964
Molecular weight:
30036.77
General function:
Involved in monooxygenase activity
Specific function:
Plays an important role in the physiology of adrenergic neurons.
Gene Name:
TH
Uniprot ID:
P07101
Molecular weight:
55611.26
Reactions
L-Tyrosine + Tetrahydrobiopterin + Oxygen → DOPA + 4a-Hydroxytetrahydrobiopterindetails
Tetrahydrobiopterin + L-Tyrosine + Oxygen → DOPA + 4a-Carbinolamine tetrahydrobiopterin + Waterdetails
General function:
Involved in carboxy-lyase activity
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:
P20711
Molecular weight:
53893.755
Reactions
DOPA → Dopamine + CO(2)details
DOPA → Dopamine + Carbon dioxidedetails
References
  1. BIRKMAYER W, HORNYKIEWICZ O: [The L-3,4-dioxyphenylalanine (DOPA)-effect in Parkinson-akinesia]. Wien Klin Wochenschr. 1961 Nov 10;73:787-8. [PubMed:13869404 ]
General function:
Involved in monooxygenase activity
Specific function:
Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic antidepressants.
Gene Name:
CYP2D6
Uniprot ID:
P10635
Molecular weight:
55768.94
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
This is one of the five types (D1 to D5) of receptors for dopamine. The activity of this receptor is mediated by G proteins which inhibit adenylyl cyclase
Gene Name:
DRD2
Uniprot ID:
P14416
Molecular weight:
50618.9
References
  1. Dupre KB, Eskow KL, Negron G, Bishop C: The differential effects of 5-HT(1A) receptor stimulation on dopamine receptor-mediated abnormal involuntary movements and rotations in the primed hemiparkinsonian rat. Brain Res. 2007 Jul 16;1158:135-43. Epub 2007 May 8. [PubMed:17553470 ]
  2. Mori A, Ohashi S, Nakai M, Moriizumi T, Mitsumoto Y: Neural mechanisms underlying motor dysfunction as detected by the tail suspension test in MPTP-treated C57BL/6 mice. Neurosci Res. 2005 Mar;51(3):265-74. Epub 2005 Jan 8. [PubMed:15710490 ]
  3. Zappia M, Annesi G, Nicoletti G, Arabia G, Annesi F, Messina D, Pugliese P, Spadafora P, Tarantino P, Carrideo S, Civitelli D, De Marco EV, Ciro-Candiano IC, Gambardella A, Quattrone A: Sex differences in clinical and genetic determinants of levodopa peak-dose dyskinesias in Parkinson disease: an exploratory study. Arch Neurol. 2005 Apr;62(4):601-5. [PubMed:15824260 ]
  4. Kovoor A, Seyffarth P, Ebert J, Barghshoon S, Chen CK, Schwarz S, Axelrod JD, Cheyette BN, Simon MI, Lester HA, Schwarz J: D2 dopamine receptors colocalize regulator of G-protein signaling 9-2 (RGS9-2) via the RGS9 DEP domain, and RGS9 knock-out mice develop dyskinesias associated with dopamine pathways. J Neurosci. 2005 Feb 23;25(8):2157-65. [PubMed:15728856 ]
  5. Onofrj M, Bonanni L, Thomas A: An expert opinion on safinamide in Parkinson's disease. Expert Opin Investig Drugs. 2008 Jul;17(7):1115-25. doi: 10.1517/13543784.17.7.1115 . [PubMed:18549347 ]
  6. Deleu D, Northway MG, Hanssens Y: Clinical pharmacokinetic and pharmacodynamic properties of drugs used in the treatment of Parkinson's disease. Clin Pharmacokinet. 2002;41(4):261-309. [PubMed:11978145 ]
  7. Koller WC, Rueda MG: Mechanism of action of dopaminergic agents in Parkinson's disease. Neurology. 1998 Jun;50(6 Suppl 6):S11-4; discussion S44-8. [PubMed:9633680 ]
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
This is one of the five types (D1 to D5) of receptors for dopamine. The activity of this receptor is mediated by G proteins which inhibit adenylyl cyclase
Gene Name:
DRD4
Uniprot ID:
P21917
Molecular weight:
48359.9
References
  1. Onofrj M, Bonanni L, Thomas A: An expert opinion on safinamide in Parkinson's disease. Expert Opin Investig Drugs. 2008 Jul;17(7):1115-25. doi: 10.1517/13543784.17.7.1115 . [PubMed:18549347 ]
  2. Deleu D, Northway MG, Hanssens Y: Clinical pharmacokinetic and pharmacodynamic properties of drugs used in the treatment of Parkinson's disease. Clin Pharmacokinet. 2002;41(4):261-309. [PubMed:11978145 ]
  3. Koller WC, Rueda MG: Mechanism of action of dopaminergic agents in Parkinson's disease. Neurology. 1998 Jun;50(6 Suppl 6):S11-4; discussion S44-8. [PubMed:9633680 ]
General function:
Involved in catalytic activity
Specific function:
Required for the function of light chain amino-acid transporters. Involved in sodium-independent, high-affinity transport of large neutral amino acids such as phenylalanine, tyrosine, leucine, arginine and tryptophan. Involved in guiding and targeting of LAT1 and LAT2 to the plasma membrane. When associated with SLC7A6 or SLC7A7 acts as an arginine/glutamine exchanger, following an antiport mechanism for amino acid transport, influencing arginine release in exchange for extracellular amino acids. Plays a role in nitric oxide synthesis in human umbilical vein endothelial cells (HUVECs) via transport of L-arginine. Required for normal and neoplastic cell growth. When associated with SLC7A5/LAT1, is also involved in the transport of L-DOPA across the blood-brain barrier, and that of thyroid hormones triiodothyronine (T3) and thyroxine (T4) across the cell membrane in tissues such as placenta. Involved in the uptake of methylmercury (MeHg) when administered as the L-cysteine or D,L-homocysteine complexes, and hence plays a role in metal ion homeostasis and toxicity. When associated with SLC7A5 or SLC7A8, involved in the cellular activity of small molecular weight nitrosothiols, via the stereoselective transport of L- nitrosocysteine (L-CNSO) across the transmembrane. Together with ICAM1, regulates the transport activity LAT2 in polarized intestinal cells, by generating and delivering intracellular signals. When associated with SLC7A5, plays an important role in transporting L-leucine from the circulating blood to the retina across the inner blood-retinal barrier
Gene Name:
SLC3A2
Uniprot ID:
P08195
Molecular weight:
67993.3
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
This is one of the five types (D1 to D5) of receptors for dopamine. The activity of this receptor is mediated by G proteins which inhibit adenylyl cyclase. Promotes cell proliferation
Gene Name:
DRD3
Uniprot ID:
P35462
Molecular weight:
44224.3
References
  1. Onofrj M, Bonanni L, Thomas A: An expert opinion on safinamide in Parkinson's disease. Expert Opin Investig Drugs. 2008 Jul;17(7):1115-25. doi: 10.1517/13543784.17.7.1115 . [PubMed:18549347 ]
  2. Deleu D, Northway MG, Hanssens Y: Clinical pharmacokinetic and pharmacodynamic properties of drugs used in the treatment of Parkinson's disease. Clin Pharmacokinet. 2002;41(4):261-309. [PubMed:11978145 ]
  3. Koller WC, Rueda MG: Mechanism of action of dopaminergic agents in Parkinson's disease. Neurology. 1998 Jun;50(6 Suppl 6):S11-4; discussion S44-8. [PubMed:9633680 ]
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
This is one of the five types (D1 to D5) of receptors for dopamine. The activity of this receptor is mediated by G proteins which activate adenylyl cyclase
Gene Name:
DRD1
Uniprot ID:
P21728
Molecular weight:
49292.8
References
  1. Onofrj M, Bonanni L, Thomas A: An expert opinion on safinamide in Parkinson's disease. Expert Opin Investig Drugs. 2008 Jul;17(7):1115-25. doi: 10.1517/13543784.17.7.1115 . [PubMed:18549347 ]
  2. Deleu D, Northway MG, Hanssens Y: Clinical pharmacokinetic and pharmacodynamic properties of drugs used in the treatment of Parkinson's disease. Clin Pharmacokinet. 2002;41(4):261-309. [PubMed:11978145 ]
  3. Koller WC, Rueda MG: Mechanism of action of dopaminergic agents in Parkinson's disease. Neurology. 1998 Jun;50(6 Suppl 6):S11-4; discussion S44-8. [PubMed:9633680 ]

Transporters

General function:
Involved in transporter activity
Specific function:
Proton-coupled intake of oligopeptides of 2 to 4 amino acids with a preference for dipeptides. May constitute a major route for the absorption of protein digestion end-products
Gene Name:
SLC15A1
Uniprot ID:
P46059
Molecular weight:
78805.3
References
  1. Han HK, Rhie JK, Oh DM, Saito G, Hsu CP, Stewart BH, Amidon GL: CHO/hPEPT1 cells overexpressing the human peptide transporter (hPEPT1) as an alternative in vitro model for peptidomimetic drugs. J Pharm Sci. 1999 Mar;88(3):347-50. [PubMed:10052994 ]
General function:
Involved in transmembrane transport
Specific function:
Sodium-independent transporter that mediates the update of aromatic acid. Can function as a net efflux pathway for aromatic amino acids in the basosolateral epithelial cells
Gene Name:
SLC16A10
Uniprot ID:
Q8TF71
Molecular weight:
55492.1
References
  1. Kim DK, Kanai Y, Chairoungdua A, Matsuo H, Cha SH, Endou H: Expression cloning of a Na+-independent aromatic amino acid transporter with structural similarity to H+/monocarboxylate transporters. J Biol Chem. 2001 May 18;276(20):17221-8. Epub 2001 Feb 20. [PubMed:11278508 ]

Only showing the first 10 proteins. There are 13 proteins in total.