Record Information
Version1.0
Created at2020-04-17 18:39:37 UTC
Updated at2020-12-07 19:11:00 UTC
CannabisDB IDCDB004815
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common 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. L-Dopa is expected to be in Cannabis as all living plants are known to produce and metabolize it.
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 Weight197.19
Monoisotopic Molecular Weight197.0688
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
Disposition

Route of exposure:

Source:

Biological location:

Role

Indirect biological role:

Environmental role:

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point285 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility5 mg/mLNot Available
logP-2.39SANGSTER (1993)
Predicted Properties
PropertyValueSource
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
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MSL-Dopa, 4 TMS, GC-MS Spectrumsplash10-014i-0790000000-b2f7f063a2c8197c7eddSpectrum
GC-MSL-Dopa, non-derivatized, GC-MS Spectrumsplash10-014i-0690000000-622497b3104c6082a45dSpectrum
GC-MSL-Dopa, 4 TMS, GC-MS Spectrumsplash10-00xr-9350000000-b0cc4636931d2de64d81Spectrum
GC-MSL-Dopa, 4 TMS, GC-MS Spectrumsplash10-014i-0590000000-4474e81e4226bb4e1d4cSpectrum
GC-MSL-Dopa, non-derivatized, GC-MS Spectrumsplash10-014i-0790000000-b2f7f063a2c8197c7eddSpectrum
GC-MSL-Dopa, non-derivatized, GC-MS Spectrumsplash10-014i-0690000000-622497b3104c6082a45dSpectrum
GC-MSL-Dopa, non-derivatized, GC-MS Spectrumsplash10-00xr-9350000000-b0cc4636931d2de64d81Spectrum
GC-MSL-Dopa, non-derivatized, GC-MS Spectrumsplash10-014i-0590000000-4474e81e4226bb4e1d4cSpectrum
GC-MSL-Dopa, non-derivatized, GC-MS Spectrumsplash10-014i-1890000000-646d209fa1943582a336Spectrum
GC-MSL-Dopa, non-derivatized, GC-MS Spectrumsplash10-014i-0690000000-720ed87e98a0d9f1721dSpectrum
Predicted GC-MSL-Dopa, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0fk9-3900000000-266d9baeda773fe1fb22Spectrum
Predicted GC-MSL-Dopa, 3 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0002-4193000000-8c76bf85d8a897e9403cSpectrum
Predicted GC-MSL-Dopa, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSL-Dopa, TMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSL-Dopa, TMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSL-Dopa, TMS_1_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSL-Dopa, TMS_1_4, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSL-Dopa, TMS_2_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSL-Dopa, TMS_2_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSL-Dopa, TMS_2_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSL-Dopa, TMS_2_4, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSL-Dopa, TMS_2_5, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSL-Dopa, TMS_2_6, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSL-Dopa, TMS_2_7, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSL-Dopa, TMS_3_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0uea-0900000000-8eb71aa0cc8622f097a22012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0a59-2900000000-bf63b9b719959b82b5432012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-056r-9300000000-a78b0b31dd33fe8479a72012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0f6t-0911000000-15affa616923dfb9c45a2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-000i-0900000000-22d8267801d0eb0b73c22012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-001i-0900000000-2c310034a1a871502b4c2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0udi-0900000000-5e6020c952f741531fcb2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0007-0970100000-49594dae82ce73e734e62012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-001i-0900000000-2183a68f58b951f3f1c72012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-03di-0900000000-0030db588fbd92c5b7612012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0006-0090000000-544615463a975baae9e42012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-0002-0729111000-0a20b01f58fff8ad7ef02012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-004i-0900000000-c8095a31ed4b3dbbc6462012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-03di-0190000000-41515cba3a69297218592012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-0002-0900000000-8074c509ef5bae1129fc2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-0006-0502193020-497bfad7ba247159ca002012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-004i-0900000000-0b0d4b6dcb7f1fa24e1a2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-004i-0029800000-05f40324c8c1fec7963a2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-0006-0000090000-c0cd80185ce47b30e5fe2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-0002-0900000000-df116b84981cf4a1371a2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Positivesplash10-0f6t-0900000000-1c1c39a8880442ea18df2012-08-31View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udj-0900000000-cf54b26df05181b0d2fc2017-07-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0900000000-d506f2673b114b8e38d22017-07-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00di-8900000000-1699873cb7650f62b5bc2017-07-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0900000000-a0d81bfc4868b0d1cbf92017-07-26View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Spectrum
Pathways
Pathways
Protein Targets
Enzymes
Protein NameGene NameLocusUniprot IDDetails
TyrosinaseTYR11q14-q21P14679 details
Catechol O-methyltransferaseCOMT22q11.21P21964 details
Tyrosine 3-monooxygenaseTH11p15.5P07101 details
Aromatic-L-amino-acid decarboxylaseDDC7p12.2P20711 details
D(2) dopamine receptorDRD211q23P14416 details
D(4) dopamine receptorDRD411p15.5P21917 details
Transporters
Protein NameGene NameLocusUniprot IDDetails
Solute carrier family 15 member 1SLC15A113q33-q34P46059 details
Monocarboxylate transporter 10SLC16A106q21-q22Q8TF71 details
Metal Bindings
Protein NameGene NameLocusUniprot IDDetails
Catechol O-methyltransferaseCOMT22q11.21P21964 details
Tyrosine 3-monooxygenaseTH11p15.5P07101 details
Cytochrome P450 2D6CYP2D622q13.1P10635 details
Receptors
Protein NameGene NameLocusUniprot IDDetails
Tyrosine 3-monooxygenaseTH11p15.5P07101 details
D(2) dopamine receptorDRD211q23P14416 details
D(4) dopamine receptorDRD411p15.5P21917 details
D(3) dopamine receptorDRD33q13.3P35462 details
D(1A) dopamine receptorDRD15q35.1P21728 details
D(1B) dopamine receptorDRD54p16.1P21918 details
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0000181
DrugBank IDDB01235
Phenol Explorer Compound IDNot Available
FoodDB 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
General ReferencesNot Available

Only showing the first 10 proteins. There are 17 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
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
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
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
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

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
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

Only showing the first 10 proteins. There are 17 proteins in total.