Livestock Metabolome Database: Showing metabocard for Dihydroxyphenylalanine (LMDB00710)

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-07-13 19:55:59 UTC

Update Date

2018-04-30 22:34:24 UTC

Lmdb

LMDB00710

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Dihydroxyphenylalanine

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.

Structure

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

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

Chemical Formula

C₉H₁₁NO₄

Average Molecular Weight

197.1879

Monoisotopic Molecular Weight

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(O)=C(O)C=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 )

Ontology

Status

Detected and Quantified

Origin

Not Available

Biofunction

Not Available

Application

Not Available

Cellular locations

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	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	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (4 TMS)	splash10-014i-0790000000-b2f7f063a2c8197c7edd	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-014i-0690000000-622497b3104c6082a45d	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (4 TMS)	splash10-00xr-9350000000-b0cc4636931d2de64d81	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (4 TMS)	splash10-014i-0590000000-4474e81e4226bb4e1d4c	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-014i-0790000000-b2f7f063a2c8197c7edd	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-014i-0690000000-622497b3104c6082a45d	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00xr-9350000000-b0cc4636931d2de64d81	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-014i-0590000000-4474e81e4226bb4e1d4c	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-014i-1890000000-646d209fa1943582a336	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-014i-0690000000-720ed87e98a0d9f1721d	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0fk9-3900000000-266d9baeda773fe1fb22	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positive	splash10-0002-4193000000-8c76bf85d8a897e9403c	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_4) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_4) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_5) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_6) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_7) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_3_2) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-0uea-0900000000-8eb71aa0cc8622f097a2	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-0a59-2900000000-bf63b9b719959b82b543	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-056r-9300000000-a78b0b31dd33fe8479a7	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-0f6t-0911000000-15affa616923dfb9c45a	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-000i-0900000000-22d8267801d0eb0b73c2	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-001i-0900000000-2c310034a1a871502b4c	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-0udi-0900000000-5e6020c952f741531fcb	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-0007-0970100000-49594dae82ce73e734e6	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-001i-0900000000-2183a68f58b951f3f1c7	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-03di-0900000000-0030db588fbd92c5b761	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-0006-0090000000-544615463a975baae9e4	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-0002-0729111000-0a20b01f58fff8ad7ef0	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-004i-0900000000-c8095a31ed4b3dbbc646	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-03di-0190000000-41515cba3a6929721859	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-0002-0900000000-8074c509ef5bae1129fc	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-0006-0502193020-497bfad7ba247159ca00	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-004i-0900000000-0b0d4b6dcb7f1fa24e1a	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-004i-0029800000-05f40324c8c1fec7963a	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-0006-0000090000-c0cd80185ce47b30e5fe	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive	splash10-0002-0900000000-df116b84981cf4a1371a	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Positive	splash10-0f6t-0900000000-1c1c39a8880442ea18df	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udj-0900000000-cf54b26df05181b0d2fc	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0udi-0900000000-d506f2673b114b8e38d2	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00di-8900000000-1699873cb7650f62b5bc	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-0900000000-a0d81bfc4868b0d1cbf9	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	Spectrum