AFCDB: L-DOPA (FDB000567)

Record Information

Version

1.0

Creation date

2010-04-08 22:04:37 UTC

Update date

2020-09-17 15:38:25 UTC

Primary ID

FDB000567

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

L-DOPA

Description

L-Dopa, also known as dopar or dopaston, belongs to the class of organic compounds known as tyrosine and derivatives. Tyrosine and derivatives are compounds containing tyrosine or a derivative thereof resulting from reaction of tyrosine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. L-Dopa is a very strong basic compound (based on its pKa). L-Dopa exists in all living organisms, ranging from bacteria to humans. Within humans, L-dopa participates in a number of enzymatic reactions. In particular, L-dopa and tetrahydrobiopterin can be converted into dopamine and 4a-hydroxytetrahydrobiopterin through its interaction with the enzyme aromatic-L-amino-acid decarboxylase. In addition, L-dopa can be converted into dopaquinone; which is catalyzed by the enzyme tyrosinase. In humans, L-dopa is involved in the metabolic disorder called hawkinsinuria. L-Dopa is an odorless tasting compound. Outside of the human body, L-Dopa is found, on average, in the highest concentration within a few different foods, such as broad beans, swiss chards, and yellow wax beans and in a lower concentration in spinachs, garden onions, and green beans. L-Dopa has also been detected, but not quantified in, several different foods, such as chicory roots, bitter gourds, mustard spinachs, pistachio, and savoy cabbages. This could make L-dopa a potential biomarker for the consumption of these foods. L-Dopa is a potentially toxic compound. L-Dopa, with regard to humans, has been found to be associated with several diseases such as eosinophilic esophagitis and alzheimer's disease; L-dopa has also been linked to several inborn metabolic disorders including aromatic l-amino acid decarboxylase deficiency and sepiapterin reductase deficiency. An optically active form of dopa having L-configuration.

CAS Number

59-92-7

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Synonym	Source
Not Available	Not Available

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

Chemical Formula

C9H11NO4

IUPAC name

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

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

Isomeric SMILES

N[C@@H](CC1=CC(O)=C(O)C=C1)C(O)=O

Average Molecular Weight

197.1879

Monoisotopic Molecular Weight

197.068807845

Classification

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 )

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Environmental:

Wastewater

Biological:

Animal

Plant:

Biological location:

Role

Indirect biological role:

Neurotoxin

Environmental role:

Environmental contaminant

Industrial application:

Prodrug

Pharmaceutical industry:

Pharmaceutical

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Solid
Physical Description	Not Available
Mass Composition	C 54.82%; H 5.62%; N 7.10%; O 32.45%	DFC
Melting Point	Mp 285.5° dec.	DFC
Boiling Point	Not Available
Experimental Water Solubility	5 mg/mL at 20 oC	YALKOWSKY,SH & DANNENFELSER,RM (1992)
Experimental logP	-2.39	SANGSTER (1993)
Experimental pKa	2.32
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	[a]20D -12.15 (c, 4 in 1N HCl)	DFC
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
GC-MS	L-DOPA, 4 TMS, GC-MS Spectrum	splash10-014i-0790000000-b2f7f063a2c8197c7edd	Spectrum
GC-MS	L-DOPA, non-derivatized, GC-MS Spectrum	splash10-014i-0690000000-622497b3104c6082a45d	Spectrum
GC-MS	L-DOPA, 4 TMS, GC-MS Spectrum	splash10-00xr-9350000000-b0cc4636931d2de64d81	Spectrum
GC-MS	L-DOPA, 4 TMS, GC-MS Spectrum	splash10-014i-0590000000-4474e81e4226bb4e1d4c	Spectrum
GC-MS	L-DOPA, non-derivatized, GC-MS Spectrum	splash10-014i-0790000000-b2f7f063a2c8197c7edd	Spectrum
GC-MS	L-DOPA, non-derivatized, GC-MS Spectrum	splash10-014i-0690000000-622497b3104c6082a45d	Spectrum
GC-MS	L-DOPA, non-derivatized, GC-MS Spectrum	splash10-00xr-9350000000-b0cc4636931d2de64d81	Spectrum
GC-MS	L-DOPA, non-derivatized, GC-MS Spectrum	splash10-014i-0590000000-4474e81e4226bb4e1d4c	Spectrum
GC-MS	L-DOPA, non-derivatized, GC-MS Spectrum	splash10-014i-1890000000-646d209fa1943582a336	Spectrum
GC-MS	L-DOPA, non-derivatized, GC-MS Spectrum	splash10-014i-0690000000-720ed87e98a0d9f1721d	Spectrum
Predicted GC-MS	L-DOPA, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0fk9-3900000000-266d9baeda773fe1fb22	Spectrum
Predicted GC-MS	L-DOPA, 3 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0002-4193000000-8c76bf85d8a897e9403c	Spectrum
Predicted GC-MS	L-DOPA, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	L-DOPA, TMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	L-DOPA, TMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	L-DOPA, TMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	L-DOPA, TMS_1_4, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	L-DOPA, TMS_2_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	L-DOPA, TMS_2_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	L-DOPA, TMS_2_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	L-DOPA, TMS_2_4, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	L-DOPA, TMS_2_5, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	L-DOPA, TMS_2_6, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	L-DOPA, TMS_2_7, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	L-DOPA, TMS_3_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-0uea-0900000000-8eb71aa0cc8622f097a2	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-0a59-2900000000-bf63b9b719959b82b543	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-056r-9300000000-a78b0b31dd33fe8479a7	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-0f6t-0911000000-15affa616923dfb9c45a	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-000i-0900000000-22d8267801d0eb0b73c2	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-001i-0900000000-2c310034a1a871502b4c	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-0udi-0900000000-5e6020c952f741531fcb	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-0007-0970100000-49594dae82ce73e734e6	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-001i-0900000000-2183a68f58b951f3f1c7	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-03di-0900000000-0030db588fbd92c5b761	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-0006-0090000000-544615463a975baae9e4	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-0002-0729111000-0a20b01f58fff8ad7ef0	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-004i-0900000000-c8095a31ed4b3dbbc646	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-03di-0190000000-41515cba3a6929721859	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-0002-0900000000-8074c509ef5bae1129fc	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-0006-0502193020-497bfad7ba247159ca00	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-004i-0900000000-0b0d4b6dcb7f1fa24e1a	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-004i-0029800000-05f40324c8c1fec7963a	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-0006-0000090000-c0cd80185ce47b30e5fe	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive	splash10-0002-0900000000-df116b84981cf4a1371a	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Positive	splash10-0f6t-0900000000-1c1c39a8880442ea18df	2012-08-31	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udj-0900000000-cf54b26df05181b0d2fc	2017-07-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0udi-0900000000-d506f2673b114b8e38d2	2017-07-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00di-8900000000-1699873cb7650f62b5bc	2017-07-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-0900000000-a0d81bfc4868b0d1cbf9	2017-07-26	View Spectrum

NMR

Type	Description	View
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Spectrum

External Links

ChemSpider ID

ChEMBL ID

KEGG Compound ID

Pubchem Compound ID

Pubchem Substance ID

Not Available

ChEBI ID

15765

Phenol-Explorer ID

Not Available

DrugBank ID

DB01235

HMDB ID

HMDB00181

CRC / DFC (Dictionary of Food Compounds) ID

HHZ68-O:BDR85-N

EAFUS ID

Not Available

Dr. Duke ID

BIGG ID

KNApSAcK ID

HET ID

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

rw1253531

SuperScent ID

Not Available

Wikipedia ID

L-Dopa

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

Food	Content Range	Average	Reference
Food			Reference

Biological Effects and Interactions

Health Effects / Bioactivities

Descriptor	ID	Definition	Reference
analgesic	35480	An agent capable of relieving pain without the loss of consciousness or without producing anaesthesia. In addition, analgesic is a role played by a compound which is exhibited by a capability to cause a reduction of pain symptoms.	DUKE
anorexic	50780	An agent which regulates the physiologic mechanisms that control the appetite and food intake.	DUKE
antidote	50247	Any protective agent counteracting or neutralizing the action of poisons.	DUKE
anti encephalopathic	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti feedant			DUKE
anti morphinic			DUKE
anti neuroleptic	35470	A class of drugs producing both physiological and psychological effects through a variety of mechanisms involving the central nervous system.	DUKE
anti Parkinsonian	48407	A drug used in the treatment of Parkinson's disease.	DUKE
anti reserpine			DUKE
anti tremor	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
aphrodisiac			DUKE
arrhythmigenic	38070	A drug used for the treatment or prevention of cardiac arrhythmias. Anti-arrhythmia drugs may affect the polarisation-repolarisation phase of the action potential, its excitability or refractoriness, or impulse conduction or membrane responsiveness within cardiac fibres.	DUKE
cardiovascular	38070	A drug used for the treatment or prevention of cardiac arrhythmias. Anti-arrhythmia drugs may affect the polarisation-repolarisation phase of the action potential, its excitability or refractoriness, or impulse conduction or membrane responsiveness within cardiac fibres.	DUKE
central nervous system active	35470	A class of drugs producing both physiological and psychological effects through a variety of mechanisms involving the central nervous system.	DUKE
depressant			DUKE
diuretic	35498	An agent that promotes the excretion of urine through its effects on kidney function.	DUKE
dopaminergic	48560	A drug used for its effects on dopamine receptors, on the life cycle of dopamine, or on the survival of dopaminergic neurons.	DUKE
emetic			DUKE
hallucinogen	35499	Drugs capable of inducing illusions, hallucinations, delusions, paranoid ideations and other alterations of mood and thinking.	DUKE
hypertensive			DUKE
hypotensive			DUKE
insectifuge	24852	Strictly, a substance intended to kill members of the class Insecta. In common usage, any substance used for preventing, destroying, repelling or controlling insects.	DUKE
miotic	51068	Aa agent causing contraction of the pupil of the eye. Because the size of the pupil is under the antagonistic control of the sympathetic and parasympathetic systems, drugs affecting either system can cause miosis. Drugs that mimic or potentiate the parasympathetic input to the circular constrictor muscle and drugs that inhibit sympathetic input to the radial dilator muscle tend to contract the pupils.	DUKE
natriuretic			DUKE
neurotoxic	50910	A poison that interferes with the functions of the nervous system.	CHEBI

Enzymes

Name	Gene Name	UniProt ID
Aromatic-L-amino-acid decarboxylase	DDC	P20711
Tyrosine 3-monooxygenase	TH	P07101
D(2) dopamine receptor	DRD2	P14416
D(4) dopamine receptor	DRD4	P21917

Pathways

Name	SMPDB Link	KEGG Link
Catecholamine Biosynthesis	SMP00012	map00350
Tyrosine Metabolism	SMP00006	map00350

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Flavor	Citations
odorless	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.

Files

MSDS

show

References

Synthesis Reference

Not Available

General Reference

Not Available

Content Reference

— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.
— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).

L-DOPA (FDB000567)

Structure for FDB000567 (L-DOPA)