MiMeDB: Showing metabocard for L-Dopa (MMDBc0000498)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2020-12-10 18:39:08 UTC

Update Date

2024-10-09 19:16:51 UTC

Metabolite ID

MMDBc0000498

Metabolite Identification

Common Name

L-Dopa

Description

L-DOPA, also known as levodopa or 3,4-dihydroxyphenylalanine is an alpha amino acid. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon). L-DOPA is found naturally in both animals and plants. It is made via biosynthesis from the amino acid L-tyrosine by the enzyme tyrosine hydroxylase.. L-DOPA is the precursor to the neurotransmitters dopamine, norepinephrine (noradrenaline), and epinephrine (adrenaline), which are collectively known as catecholamines. The Swedish scientist Arvid Carlsson first showed in the 1950s that administering L-DOPA to animals with drug-induced (reserpine) Parkinsonian symptoms caused a reduction in the intensity of the animals' symptoms. Unlike dopamine itself, L-DOPA can be taken orally and crosses the blood-brain barrier. It is rapidly taken up by dopaminergic neurons and converted to dopamine. In particular, it is metabolized to dopamine by aromatic L-amino acid decarboxylase. Pyridoxal phosphate (vitamin B6) is a required cofactor for this decarboxylation, and may be administered along with levodopa, usually as pyridoxine. As a result, L-DOPA is a drug that is now used for the treatment of Parkinsonian disorders and DOPA-Responsive Dystonia. It is usually given with agents that inhibit its conversion to dopamine outside of the central nervous system. It is standard clinical practice in treating Parkinsonism to co-administer a peripheral DOPA decarboxylase inhibitor - carbidopa or benserazide - and often a catechol-O-methyl transferase (COMT) inhibitor, to prevent synthesis of dopamine in peripheral tissue. Side effects of L-DOPA treatment may include: hypertension, arrhythmias, nausea, gastrointestinal bleeding, disturbed respiration, hair loss, disorientation and confusion. L-DOPA can act as an L-tyrosine mimetic and be incorporated into proteins by mammalian cells in place of L-tyrosine, generating protease-resistant and aggregate-prone proteins in vitro and may contribute to neurotoxicity with chronic L-DOPA administration. L-phenylalanine, L-tyrosine, and L-DOPA are all precursors to the biological pigment melanin. The enzyme tyrosinase catalyzes the oxidation of L-DOPA to the reactive intermediate dopaquinone, which reacts further, eventually leading to melanin oligomers.

Structure

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


  Mrv1652309032023562D          

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

> <DATABASE_NAME>
MIME

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

> <INCHI_IDENTIFIER>
InChI=1S/C9H11NO4/c10-6(9(13)14)3-5-1-2-7(11)8(12)4-5/h1-2,4,6,11-12H,3,10H2,(H,13,14)/t6-/m0/s1

> <INCHI_KEY>
WTDRDQBEARUVNC-LURJTMIESA-N

> <FORMULA>
C9H11NO4

> <MOLECULAR_WEIGHT>
197.1879

> <EXACT_MASS>
197.068807845

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
25

> <JCHEM_AVERAGE_POLARIZABILITY>
18.90987044668941

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <JCHEM_LOGP>
-1.7921814507627933

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.686049362161093

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.650696949850563

> <JCHEM_PKA_STRONGEST_BASIC>
9.055027392905787

> <JCHEM_POLAR_SURFACE_AREA>
103.77999999999999

> <JCHEM_REFRACTIVITY>
49.07810000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
levodopa

> <JCHEM_VEBER_RULE>
0

$$$$

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

Synonyms

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

Molecular Formula

C₉H₁₁NO₄

Average Mass

197.1879

Monoisotopic Mass

197.068807845

IUPAC Name

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

Traditional Name

levodopa

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C9H11NO4/c10-6(9(13)14)3-5-1-2-7(11)8(12)4-5/h1-2,4,6,11-12H,3,10H2,(H,13,14)/t6-/m0/s1

InChI Key

WTDRDQBEARUVNC-LURJTMIESA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as tyrosine and derivatives. Tyrosine and derivatives are compounds containing tyrosine or a derivative thereof resulting from reaction of tyrosine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Tyrosine and derivatives

Alternative Parents

Substituents

Tyrosine or derivatives
Phenylalanine or derivatives
3-phenylpropanoic-acid
Alpha-amino acid
Amphetamine or derivatives
L-alpha-amino acid
Catechol
1-hydroxy-4-unsubstituted benzenoid
Aralkylamine
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Benzenoid
Amino acid
Carboxylic acid
Monocarboxylic acid or derivatives
Organic oxide
Organooxygen compound
Organonitrogen compound
Primary amine
Primary aliphatic amine
Organic nitrogen compound
Organic oxygen compound
Carbonyl group
Hydrocarbon derivative
Organopnictogen compound
Amine
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

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

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

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

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	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	2014-06-16	View 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	2014-06-16	View 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	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (4 TMS)	splash10-014i-0590000000-4474e81e4226bb4e1d4c	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-014i-0790000000-b2f7f063a2c8197c7edd	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-014i-0690000000-622497b3104c6082a45d	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00xr-9350000000-b0cc4636931d2de64d81	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-014i-0590000000-4474e81e4226bb4e1d4c	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-014i-1890000000-646d209fa1943582a336	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-014i-0690000000-720ed87e98a0d9f1721d	2017-09-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0fk9-3900000000-266d9baeda773fe1fb22	2017-08-28	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positive	splash10-0002-4193000000-8c76bf85d8a897e9403c	2017-10-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_4) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_4) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_5) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_6) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_7) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_3_2) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-0uea-0900000000-8eb71aa0cc8622f097a2	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-0a59-2900000000-bf63b9b719959b82b543	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-056r-9300000000-a78b0b31dd33fe8479a7	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-0f6t-0911000000-15affa616923dfb9c45a	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-000i-0900000000-22d8267801d0eb0b73c2	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-001i-0900000000-2c310034a1a871502b4c	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-0udi-0900000000-5e6020c952f741531fcb	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-0007-0970100000-49594dae82ce73e734e6	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-001i-0900000000-2183a68f58b951f3f1c7	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-03di-0900000000-0030db588fbd92c5b761	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-0006-0090000000-544615463a975baae9e4	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-0002-0729111000-0a20b01f58fff8ad7ef0	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-004i-0900000000-c8095a31ed4b3dbbc646	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-03di-0190000000-41515cba3a6929721859	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-0002-0900000000-8074c509ef5bae1129fc	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-0006-0502193020-497bfad7ba247159ca00	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-004i-0900000000-0b0d4b6dcb7f1fa24e1a	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-004i-0029800000-05f40324c8c1fec7963a	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-0006-0000090000-c0cd80185ce47b30e5fe	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive	splash10-0002-0900000000-df116b84981cf4a1371a	2012-08-31	View Spectrum
LC-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 LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udj-0900000000-cf54b26df05181b0d2fc	2017-07-26	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0udi-0900000000-d506f2673b114b8e38d2	2017-07-26	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00di-8900000000-1699873cb7650f62b5bc	2017-07-26	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-0900000000-a0d81bfc4868b0d1cbf9	2017-07-26	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)		2012-12-04	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-16	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)		2012-12-05	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

Biospecimen Locations

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

Tissue Locations

Adrenal Medulla
Bladder
Brain
Epidermis
Intestine
Neuron
Placenta
Platelet
Skeletal Muscle

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

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

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Data Source	Reference
MMDBr0000067	L-Dopa	Dopamine	Not Available	VMH	30371894
MMDBr0002295	L-erythro-tetrahydrobiopterin	L-Dopa	tyrosine hydroxylase	VMH	10727395 9920892
MMDBr0002298	L-Tyrosine	L-Dopa	tyrosinase	VMH	5294951
MMDBr0002299	L-Dopa	Dopaquinone	tyrosinase	VMH	5294951
MMDBr0004123	5-S-Cysteinyldopa	L-Dopa	Not Available	VMH	10903891
MMDBr0004175	L-Dopa	S-Adenosylhomocysteine	Not Available	VMH	12075857
MMDBr0010407	L-erythro-tetrahydrobiopterin	L-Dopa	tyrosine hydroxylase	VMH; KEGG	30371894
MMDBr0010408	L-Tyrosine	L-Dopa	tyrosinase	VMH; KEGG	30371894
MMDBr0010439	Leucodopachrome	L-Dopa	Not Available	VMH; KEGG	30371894

Health Effects and Bioactivity

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

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Archaea	Euryarchaeota	1	Human feces	Indirect association between microbiota composition and metabolites measured in host biospecimen
Bacteria	Bacteroidetes	7	Human feces; Human stool	Indirect association between microbiota composition and metabolites measured in host biospecimen; Metabolic reconstruction
Bacteria	Firmicutes	95	Human feces; Human stool; Pig ; Human ; Cattle	Indirect association between microbiota composition and metabolites measured in host biospecimen; Metabolic reconstruction
Bacteria	Proteobacteria	209	Human feces; Human sputum; Human ; Human unknown; Pig ; Human pleural fluid plaque; Human dental plaque; Human nasal swab	Metabolic reconstruction
Bacteria	Actinobacteria	90	Human feces; Human ; Human supragingival plaque	Metabolic reconstruction
Archaea	Euryarchaeota	2		Metabolic reconstruction
Bacteria	Fusobacteria	2	Human ; Human feces	Metabolic reconstruction
Bacteria	Planctomycetes	2	Human feces	Metabolic reconstruction
Eukaryota/Fungi	Basidiomycota	2	Human feces
Eukaryota/Fungi	Ascomycota	5	Human feces

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference
Animal		Haliotis	FooDB	31437929
Animal		Strombidae	FooDB	31437929
Animal		Clupea harengus harengus	FooDB	31437929
Animal		Undaria pinnatifida	FooDB	31437929
Animal		Peprilus triacanthus	FooDB	31437929
Animal		Rhodophyta	FooDB	31437929
Animal		Myoxocephalus	FooDB	31437929
Animal		Eucheuma	FooDB	31437929
Animal		Saccharina japonica	FooDB	31437929
Animal		Spirulina	FooDB	31437929
Animal		Lota lota	FooDB	31437929
Animal		Porphyra umbilicalis	FooDB	31437929
Animal		Chondrus crispus	FooDB	31437929
Animal		Laminaria	FooDB	31437929
Plant		Apium graveolens var. dulce	FooDB	31437929
Plant		Beta vulgaris	FooDB	31437929
Plant		Annona squamosa	FooDB	31437929
Plant		Xanthosoma sagittifolium	FooDB	31437929
Plant		Basella alba	FooDB	31437929
Plant		Vitis	FooDB	31437929
Plant		Capsicum baccatum var. baccatum	FooDB	31437929
Plant			FooDB	31437929
Plant		Cucurbita pepo var. cylindrica	FooDB	31437929
Plant		Capsicum annuum	FooDB	31437929
Plant		Citrus latifolia	FooDB	31437929
Plant		Byrsonima crassifolia	FooDB	31437929
Plant		Capsicum pubescens	FooDB	31437929
Plant		Carya illinoinensis	FooDB	31437929
Plant		Crateva religiosa	FooDB	31437929
Plant		Vitis aestivalis	FooDB	31437929
Plant		Eugenia javanica	FooDB	31437929
Plant		Mentha arvensis	FooDB	31437929
Plant			FooDB	31437929
Plant		Vaccinium stamineum	FooDB	31437929
Plant		Brassica rapa var. chinensis	FooDB	31437929
Plant		Cinnamomum aromaticum	FooDB	31437929
Plant		Ribes rubrum	FooDB	31437929
Plant		Psophocarpus tetragonolobus	FooDB	31437929
Plant		Ipomoea batatas	FooDB	31437929
Plant		Solanum lycopersicum var. cerasiforme	FooDB	31437929
Plant		Chenopodium album	FooDB	31437929
Plant		Beta vulgaris ssp. cicla	FooDB	31437929
Plant		Pastinaca sativa	FooDB	31437929
Plant		Allium ampeloprasum	FooDB	31437929
Plant		Grataegosorbus mitschurinii	FooDB	31437929
Plant		Sechium edule	FooDB	31437929
Plant		Brassica oleracea	FooDB	31437929
Plant		Solanum tuberosum	FooDB	31437929
Plant		Allium cepa	FooDB	31437929
Plant		Diospyros virginiana	FooDB	31437929
Plant		Origanum x majoricum	FooDB	31437929
Plant		Lactuca sativa l. var. longifolia	FooDB	31437929
Plant		Rumex	FooDB	31437929
Plant		Rubus x loganobaccus	FooDB	31437929
Plant		Tragopogon porrifolius	FooDB	31437929
Plant		Allium ascalonicum	FooDB	31437929
Plant		Citrullus lanatus var. fistulosus	FooDB	31437929
Plant		Taraxacum officinale	FooDB	31437929
Plant		Rubus chamaemorus	FooDB	31437929
Plant		Amelanchier alnifolia	FooDB	31437929
Plant		Eugenia uniflora	FooDB	31437929
Plant		Cucurbita pepo var. cylindrica	FooDB	31437929
Plant		Curcuma longa	FooDB	31437929
Plant		Annona reticulata	FooDB	31437929
Plant		Sesbania bispinosa	FooDB	31437929
Plant		Elettaria cardamomum	FooDB	31437929
Plant		Ananas comosus	FooDB	31437929
Plant		Persea americana	FooDB	31437929
Plant		Ribes x nidigrolaria	FooDB	31437929
Plant		Garcinia mangostana	FooDB	31437929
Plant		Lathyrus sativus	FooDB	31437929
Plant		Dioscorea pentaphylla	FooDB	31437929
Plant		Allium tuberosum	FooDB	31437929
Plant		Brassica oleracea var. botrytis	FooDB	31437929
Plant		Chenopodium quinoa	FooDB	31437929
Plant		Cichorium intybus	FooDB	31437929
Plant		Corchorus olitorius	FooDB	31437929
Plant		Cucumis melo	FooDB	31437929
Plant		Juglans nigra	FooDB	31437929
Plant		Gaylussacia baccata	FooDB	31437929
Plant		Petasites japonicus	FooDB	31437929
Plant		Prunus tomentosa	FooDB	31437929
Plant		Brassica oleracea l. var. capitata l. f. alba dc.	FooDB	31437929
Plant		Maranta arundinacea	FooDB	31437929
Plant		Mentha x piperita	FooDB	31437929
Plant		Cinnamomum verum	FooDB	31437929
Plant		Matteuccia struthiopteris	FooDB	31437929
Plant		Glycine max	FooDB	31437929
Plant		Cucurbita moschata	FooDB	31437929
Plant		Vaccinium myrtilloides	FooDB	31437929
Plant		Ocimum basilicum	FooDB	31437929
Plant		Macadamia	FooDB	31437929
Plant		Tilia	FooDB	31437929
Plant		Beta vulgaris ssp. cicla	FooDB	31437929
Plant		Nelumbo	FooDB	31437929
Plant		Papaver	FooDB	31437929
Plant		Rosa	FooDB	31437929
Plant		Brassica oleracea var. conica	FooDB	31437929
Plant		Citrus limon	FooDB	31437929
Plant		Apium graveolens var. rapaceum	FooDB	31437929
Plant		Capsicum annuum var. annuum	FooDB	31437929
Plant		Lippia graveolens	FooDB	31437929
Plant		Annona cherimola	FooDB	31437929
Plant		Sesamum orientale	FooDB	31437929
Plant		Brassica rapa var. pekinensis	FooDB	31437929
Plant		Brassica rapa	FooDB	31437929
Plant		Prunus	FooDB	31437929
Plant		Cucurbita pepo var. clypeata	FooDB	31437929
Plant		Capparis spinosa	FooDB	31437929
Plant		Vaccinium deliciosum	FooDB	31437929
Plant		Citrus sinensis	FooDB	31437929
Plant		Lens culinaris	FooDB	31437929
Plant		Phaseolus lunatus	FooDB	31437929
Plant		Artocarpus heterophyllus	FooDB	31437929
Plant		Prunus virginiana	FooDB	31437929
Plant		Musa acuminata	FooDB	31437929
Plant		Spinacia oleracea	FooDB	31437929
Plant		Macadamia tetraphylla	FooDB	31437929
Plant		Vigna unguiculata ssp. unguiculata	FooDB	31437929
Plant		Citrullus lanatus	FooDB	31437929
Plant		Lagenaria siceraria	FooDB	31437929
Plant		Linum usitatissimum	FooDB	31437929
Plant		Carissa macrocarpa	FooDB	31437929
Plant		Phyllostachys edulis	FooDB	31437929
Plant		Satureja hortensis	FooDB	31437929
Plant		Averrhoa carambola	FooDB	31437929
Plant		Prunus domestica	FooDB	31437929
Plant		Prunus armeniaca	FooDB	31437929
Plant		Sorbus aucuparia	FooDB	31437929
Plant		Carum carvi	FooDB	31437929
Plant		Allium schoenoprasum	FooDB	31437929
Plant		Citrus reticulata	FooDB	31437929
Plant		Brassica oleracea var. costata	FooDB	31437929
Plant		Panax	FooDB	31437929
Plant		Nelumbo nucifera	FooDB	31437929
Plant		Bertholletia excelsa	FooDB	31437929
Plant		Cymbopogon citratus	FooDB	31437929
Plant		Ceratonia siliqua	FooDB	31437929
Plant		Coriandrum sativum	FooDB	31437929
Plant		Luffa aegyptiaca	FooDB	31437929
Plant		Vigna umbellata	FooDB	31437929
Plant	Fruit	Persea americana	FooDB	31437929
Plant		Rubus occidentalis	FooDB	31437929
Plant		Allium fistulosum	FooDB	31437929
Plant		Capsicum	FooDB	31437929
Plant		Carthamus tinctorius	FooDB	31437929
Plant		Cicer arietinum	FooDB	31437929
Plant		Tilia cordata	FooDB	31437929
Plant		Vaccinium alaskaense	FooDB	31437929
Plant		Anacardium occidentale	FooDB	31437929
Plant		Durio zibethinus	FooDB	31437929
Plant		Prunus persica var. nucipersica	FooDB	31437929
Plant		Eriobotrya japonica	FooDB	31437929
Plant		Ribes glandulosum	FooDB	31437929
Plant		Brassica napus var. pabularia	FooDB	31437929
Plant		Verbena officinalis	FooDB	31437929
Plant		Diospyros kaki	FooDB	31437929
Plant		Oenothera biennis	FooDB	31437929
Plant		Camellia sinensis	FooDB	31437929
Plant		Vaccinium oxycoccos	FooDB	31437929
Plant		Virola surinamensis	FooDB	31437929
Plant		Rumex acetosa	FooDB	31437929
Plant		Theobroma cacao	FooDB	31437929
Plant		Solanum lycopersicum var. lycopersicum	FooDB	31437929
Plant		Aloysia triphylla	FooDB	31437929
Plant		Vaccinium parvifolium	FooDB	31437929
Plant		Capsicum chinense	FooDB	31437929
Plant		Pyrus pyrifolia	FooDB	31437929
Plant		Phaseolus vulgaris	FooDB	31437929
Plant		Brassica oleracea var. capitata	FooDB	31437929
Plant		Vaccinium reticulatum	FooDB	31437929
Plant		Solanum quitoense	FooDB	31437929
Plant		Vaccinium myrtillus	FooDB	31437929
Plant		Theobroma grandiflorum	FooDB	31437929
Plant		Syzygium aromaticum	FooDB	31437929
Plant		Ginkgo biloba	FooDB	31437929
Plant		Vigna unguiculata ssp. cylindrica	FooDB	31437929
Plant			FooDB	31437929
Plant		Flammulina velutipes	FooDB	31437929
Plant		Satureja montana	FooDB	31437929
Plant		Perideridia oregana	FooDB	31437929
Plant		Citrus japonica	FooDB	31437929
Plant		Vaccinium arboreum	FooDB	31437929
Plant		Wasabia japonica	FooDB	31437929
Plant		Origanum onites	FooDB	31437929
Plant		Prunus avium	FooDB	31437929
Plant		Pouteria sapota	FooDB	31437929
Plant		Beta vulgaris var. rubra	FooDB	31437929
Plant		Phaseolus vulgaris	FooDB	31437929
Plant		Piper nigrum	FooDB	31437929
Plant		Viburnum edule	FooDB	31437929
Plant		Vitis vinifera	FooDB	31437929
Plant		Origanum vulgare	FooDB	31437929
Plant		Dioscorea	FooDB	31437929
Plant		Vaccinium uliginosum	FooDB	31437929
Plant		Momordica charantia	FooDB	31437929
Plant		Rubus ursinus x idaeus	FooDB	31437929
Plant		Castanea	FooDB	31437929
Plant		Cirsium	FooDB	31437929
Plant		Raphanus sativus var. sativus	FooDB	31437929
Plant		Pleurotus ostreatus	FooDB	31437929
Plant		Opuntia	FooDB	31437929
Plant		Colocasia esculenta	FooDB	31437929
Plant		Prunus persica var. persica	FooDB	31437929
Plant		Anthriscus cerefolium	FooDB	31437929
Plant		Solanum melongena	FooDB	31437929
Plant		Cucumis sativus	FooDB	31437929
Plant		Nuphar lutea	FooDB	31437929
Plant		Pachyrhizus erosus	FooDB	31437929
Plant		Lupinus albus	FooDB	31437929
Plant	Plant	Portulaca oleracea	FooDB	31437929
Plant		Cichorium endivia	FooDB	31437929
Plant		Myristica fragrans	FooDB	31437929
Plant		Elaeis	FooDB	31437929
Plant		Dysphania ambrosioides	FooDB	31437929
Plant		Raphanus sativus var. niger	FooDB	31437929
Plant		Cinnamomum	FooDB	31437929
Plant		Photinia melanocarpa	FooDB	31437929
Plant		Ribes uva-crispa	FooDB	31437929
Plant		Feijoa sellowiana	FooDB	31437929
Plant		Apium graveolens	FooDB	31437929
Plant		Vaccinium	FooDB	31437929
Plant		Lablab purpureus	FooDB	31437929
Plant		Rheum rhabarbarum	FooDB	31437929
Plant		Crocus sativus	FooDB	31437929
Plant		Syzygium jambos	FooDB	31437929
Plant		Salix pulchra	FooDB	31437929
Plant		Citrus maxima	FooDB	31437929
Plant		Fagus	FooDB	31437929
Plant		Salvia officinalis	FooDB	31437929
Plant		Castanea sativa	FooDB	31437929
Plant		Cydonia oblonga	FooDB	31437929
Plant		Cucurbita maxima	FooDB	31437929
Plant		Opuntia cochenillifera	FooDB	31437929
Plant		Annona muricata	FooDB	31437929
Plant		Vaccinium ovatum	FooDB	31437929
Plant		Thymus pulegioides	FooDB	31437929
Plant		Phaseolus coccineus	FooDB	31437929
Plant		Cucurbita	FooDB	31437929
Plant		Mespilus germanica	FooDB	31437929
Plant		Cocos nucifera	FooDB	31437929
Plant		Tamarindus indica	FooDB	31437929
Plant		Brassica rapa var. perviridis	FooDB	31437929
Plant		Mentha aquatica	FooDB	31437929
Plant		Salvia elegans	FooDB	31437929
Plant		Mentha	FooDB	31437929
Plant	Flower	Vicia faba	FooDB	31437929
Plant		Sagittaria latifolia	FooDB	31437929
Plant		Sambucus	FooDB	31437929
Plant		Syzygium cumini	FooDB	31437929
Plant		Psidium guajava	FooDB	31437929
Plant		Typha angustifolia	FooDB	31437929
Plant		Pinus	FooDB	31437929
Plant		Tilia tomentosa	FooDB	31437929
Plant		Empetrum nigrum	FooDB	31437929
Plant		Olea europaea	FooDB	31437929
Plant		Myrica rubra	FooDB	31437929
Plant		Valerianella locusta	FooDB	31437929
Plant	Fruit	Vicia faba	FooDB	31437929
Plant		Cucurbita maxima	FooDB	31437929
Plant		Vaccinium angustifolium x vaccinium corymbosum	FooDB	31437929
Plant		Sisymbrium	FooDB	31437929
Plant		Vaccinium vitis-idaea	FooDB	31437929
Plant		Vanilla	FooDB	31437929
Plant		Daucus carota	FooDB	31437929
Plant	Fruit	Solanum melongena	FooDB	31437929
Plant		Carya	FooDB	31437929
Plant		Physalis philadelphica var. immaculata	FooDB	31437929
Plant		Borago officinalis	FooDB	31437929
Plant		Hyssopus officinalis	FooDB	31437929
Plant		Manihot esculenta	FooDB	31437929
Plant		Raphanus sativus	FooDB	31437929
Plant		Scorzonera hispanica	FooDB	31437929
Plant		Vigna unguiculata ssp. sesquipedalis	FooDB	31437929
Plant		Angelica keiskei	FooDB	31437929
Plant		Vigna radiata	FooDB	31437929
Plant		Prunus dulcis	FooDB	31437929
Plant		Ipomoea aquatica	FooDB	31437929
Plant		Rubus spectabilis	FooDB	31437929
Plant		Cuminum cyminum	FooDB	31437929
Plant		Allium sativum	FooDB	31437929
Plant		Sinapis alba	FooDB	31437929
Plant		Cantharellus cibarius	FooDB	31437929
Plant		Fragaria x ananassa	FooDB	31437929
Plant		Brassica ruvo	FooDB	31437929
Plant		Arachis hypogaea	FooDB	31437929
Plant		Pyrus communis	FooDB	31437929
Plant		Rubus idaeus	FooDB	31437929
Plant		Morus nigra	FooDB	31437929
Plant		Apium graveolens var. secalinum	FooDB	31437929
Plant		Pinus edulis	FooDB	31437929
Plant		Abelmoschus esculentus	FooDB	31437929
Plant		Solanum lycopersicum	FooDB	31437929
Plant		Opuntia macrorhiza	FooDB	31437929
Plant		Moringa oleifera	FooDB	31437929
Plant		Passiflora edulis	FooDB	31437929
Plant		Vigna angularis	FooDB	31437929
Plant		Manilkara zapota	FooDB	31437929
Plant	Seed	Vicia faba	FooDB	31437929
Plant		Allium cepa	FooDB	31437929
Plant		Capsicum annuum	FooDB	31437929
Plant		Mentha spicata	FooDB	31437929
Plant		Malus	FooDB	31437929
Plant		Corylus	FooDB	31437929
Plant		Juglans	FooDB	31437929
Plant		Capsicum annuum	FooDB	31437929
Plant		Sambucus nigra	FooDB	31437929
Plant		Helianthus annuus	FooDB	31437929
Plant		Mangifera indica	FooDB	31437929
Plant		Anethum graveolens	FooDB	31437929
Plant			FooDB	31437929
Plant	Stem	Vicia faba	FooDB	31437929
Plant		Brassica rapa var. rapa	FooDB	31437929
Plant		Ribes nigrum	FooDB	31437929
Plant		Illicium verum	FooDB	31437929
Plant		Zingiber officinale	FooDB	31437929
Plant		Chamaemelum nobile	FooDB	31437929
Plant		Auricularia auricula-judae	FooDB	31437929
Plant		Petroselinum crispum	FooDB	31437929
Plant		Pisum sativum	FooDB	31437929
Plant		Laurus nobilis	FooDB	31437929
Plant		Attalea speciosa	FooDB	31437929
Plant		Juglans ailanthifolia	FooDB	31437929
Plant		Lupinus	FooDB	31437929
Plant		Polygonum alpinum	FooDB	31437929
Plant		Melissa officinalis	FooDB	31437929
Plant		Hippophae rhamnoides	FooDB	31437929
Plant		Pediomelum esculentum	FooDB	31437929
Plant		Brassica juncea	FooDB	31437929
Plant		Auricularia polytricha	FooDB	31437929
Plant		Camellia oleifera	FooDB	31437929
Plant		Vaccinium corymbosum	FooDB	31437929
Plant		Chrysanthemum coronarium	FooDB	31437929
Plant		Eleocharis dulcis	FooDB	31437929
Plant		Actinidia chinensis	FooDB	31437929
Plant		Carica papaya	FooDB	31437929
Plant		Thymus vulgaris	FooDB	31437929
Plant		Rubus arcticus	FooDB	31437929
Plant		Medicago sativa	FooDB	31437929
Plant		Phaseolus vulgaris	FooDB	31437929
Plant		Pimenta dioica	FooDB	31437929
Plant		Rumex articus	FooDB	31437929
Plant		Vigna mungo	FooDB	31437929
Plant		Agaricus bisporus	FooDB	31437929
Plant		Cajanus cajan	FooDB	31437929
Plant		Hibiscus sabdariffa	FooDB	31437929
Plant		Capsicum annuum	FooDB	31437929
Plant		Canarium ovatum	FooDB	31437929
Plant		Benincasa hispida	FooDB	31437929
Plant		Ribes aureum var. villosum	FooDB	31437929
Plant		Brassica oleracea var. italica	FooDB	31437929
Plant		Origanum majorana	FooDB	31437929
Plant		Armoracia rusticana	FooDB	31437929
Plant		Prunus persica	FooDB	31437929
Plant		Cucurbita pepo var. cylindrica	FooDB	31437929
Plant		Brassica oleracea var. gemmifera	FooDB	31437929
Plant		Vaccinium macrocarpon	FooDB	31437929
Plant		Brassica oleracea var. gongylodes	FooDB	31437929
Plant		Eruca vesicaria ssp. sativa	FooDB	31437929
Plant		Foeniculum vulgare	FooDB	31437929
Plant		Arctium lappa	FooDB	31437929
Plant		Juglans cinerea	FooDB	31437929
Plant		Phoenix dactylifera	FooDB	31437929
Plant		Artocarpus altilis	FooDB	31437929
Plant		Metroxylon sagu	FooDB	31437929
Plant		Capsicum annuum	FooDB	31437929
Plant		Vitis rotundifolia	FooDB	31437929
Plant			FooDB	31437929
Plant		Prunus cerasus	FooDB	31437929
Plant		Vigna unguiculata	FooDB	31437929
Plant		Cynara scolymus	FooDB	31437929
Plant		Psidium cattleianum	FooDB	31437929
Plant		Cyathea	FooDB	31437929
Plant		Brosimum alicastrum	FooDB	31437929
Plant		Citrus x paradisi	FooDB	31437929
Plant		Rosmarinus officinalis	FooDB	31437929
Plant		Castanea mollissima	FooDB	31437929
Plant		Lentinus edodes	FooDB	31437929
Plant		Capsicum annuum	FooDB	31437929
Plant		Ficus carica	FooDB	31437929
Plant		Morus	FooDB	31437929
Plant		Vitis labrusca	FooDB	31437929
Plant		Lepidium sativum	FooDB	31437929
Plant		Daucus carota ssp. sativus	FooDB	31437929
Plant		Phytolacca americana	FooDB	31437929
Plant		Helianthus tuberosus	FooDB	31437929
Plant		Grifola frondosa	FooDB	31437929
Plant		Tetragonia tetragonioides	FooDB	31437929
Plant		Cucumis metuliferus	FooDB	31437929
Plant		Myrica	FooDB	31437929
Plant		Nephelium lappaceum	FooDB	31437929
Plant		Vicia faba	FooDB	31437929
Plant		Artemisia vulgaris	FooDB	31437929
Plant		Castanea crenata	FooDB	31437929
Plant		Litchi chinensis	FooDB	31437929
Plant		Quercus	FooDB	31437929
Plant		Corylus avellana	FooDB	31437929
Plant		Vaccinium angustifolium	FooDB	31437929
Plant	Fruit	Musa x paradisiaca	FooDB	31437929
Plant		Malpighia emarginata	FooDB	31437929
Plant		Juglans regia	FooDB	31437929
Plant		Trigonella foenum-graecum	FooDB	31437929
Plant		Physalis	FooDB	31437929
Plant			FooDB	31437929
Plant		Thelesperma	FooDB	31437929
Plant		Brassica oleracea var. sabauda	FooDB	31437929
Plant		Chamerion angustifolium	FooDB	31437929
Plant		Brassica napus	FooDB	31437929
Plant		Vaccinium elliottii	FooDB	31437929
Plant		Asparagus officinalis	FooDB	31437929
Plant		Levisticum officinale	FooDB	31437929
Plant		Ziziphus zizyphus	FooDB	31437929
Plant		Dimocarpus longan	FooDB	31437929
Plant		Citrus aurantiifolia	FooDB	31437929
Plant		Salvia hispanica	FooDB	31437929
Plant		Matricaria recutita	FooDB	31437929
Plant		Cynara cardunculus	FooDB	31437929
Plant		Pangium edule	FooDB	31437929
Plant		Lactuca sativa	FooDB	31437929
Plant		Pimpinella anisum	FooDB	31437929
Plant		Artemisia dracunculus	FooDB	31437929
Plant		Vitellaria paradoxa	FooDB	31437929
Plant		Allium	FooDB	31437929
Plant		Brassica oleracea var. viridis	FooDB	31437929
Plant		Eragrostis tef	FooDB	31437929
Plant		Agave	FooDB	31437929
Plant		Pistacia vera	FooDB	31437929
Plant		Hedysarum alpinum	FooDB	31437929
Plant		Vigna aconitifolia	FooDB	31437929
Plant		Malus pumila	FooDB	31437929
Plant		Diospyros	FooDB	31437929
Plant		Amaranthus	FooDB	31437929
Plant		Punica granatum	FooDB	31437929
Plant		Mammea americana	FooDB	31437929
Plant		Gossypium	FooDB	31437929
Plant		Brassica alboglabra	FooDB	31437929

Host Biospecimen and Location

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

External Links

HMDB ID

HMDB0000181

DrugBank ID

DB01235

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

L-DIHYDROXY-PHENYLALANINE

BiGG ID

34719

Wikipedia Link

Levodopa

METLIN ID

PubChem Compound

6047

PDB ID

Not Available

ChEBI ID

15765

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Hyland K, Clayton PT: Aromatic L-amino acid decarboxylase deficiency: diagnostic methodology. Clin Chem. 1992 Dec;38(12):2405-10. [PubMed:1281049 ]
Tada K, Kudo T, Kishimoto Y: Effects of L-dopa or dopamine on human decidual prostaglandin synthesis. Acta Med Okayama. 1991 Oct;45(5):333-8. doi: 10.18926/AMO/32193. [PubMed:1755339 ]
Crivellato E, Damiani D, Mallardi F: Comparison between the L-DOPA histofluorescence procedure and the indirect immunofluorescence with anti-T6 and -HLA-DR monoclonal antibodies in visualizing Langerhans cells of human epidermis. Acta Histochem. 1990;88(1):59-64. doi: 10.1016/S0065-1281(11)80247-3. [PubMed:2113342 ]
de Jong AP, Kok RM, Cramers CA, Wadman SK, Haan E: A new method for the determination of L-dopa and 3-O-methyldopa in plasma and cerebrospinal fluid using gas chromatography and electron capture negative ion mass spectrometry. Clin Chim Acta. 1988 Jan 15;171(1):49-61. doi: 10.1016/0009-8981(88)90290-2. [PubMed:3127089 ]
Kagedal B, Pettersson A: Liquid-chromatographic determination of 5-S-L-cysteinyl-L-dopa with electrochemical detection in urine prepurified with a phenylboronate affinity gel. Clin Chem. 1983 Dec;29(12):2031-4. [PubMed:6416708 ]
Michel H, Solere M, Granier P, Cauvet G, Bali JP, Pons F, Bellet-Hermann H: Treatment of cirrhotic hepatic encephalopathy with L-dopa. A controlled trial. Gastroenterology. 1980 Aug;79(2):207-11. [PubMed:6995221 ]
Streifler M, Avrami E, Rabey JM: L-dopa and the secretion of sebum in Parkinsonian patients. Eur Neurol. 1980;19(1):43-8. doi: 10.1159/000115127. [PubMed:7371653 ]
Goldstein DS, Hahn SH, Holmes C, Tifft C, Harvey-White J, Milstien S, Kaufman S: Monoaminergic effects of folinic acid, L-DOPA, and 5-hydroxytryptophan in dihydropteridine reductase deficiency. J Neurochem. 1995 Jun;64(6):2810-3. doi: 10.1046/j.1471-4159.1995.64062810.x. [PubMed:7760062 ]
Dutton J, Copeland LG, Playfer JR, Roberts NB: Measuring L-dopa in plasma and urine to monitor therapy of elderly patients with Parkinson disease treated with L-dopa and a dopa decarboxylase inhibitor. Clin Chem. 1993 Apr;39(4):629-34. [PubMed:8472357 ]
Kageyama T, Nakamura M, Matsuo A, Yamasaki Y, Takakura Y, Hashida M, Kanai Y, Naito M, Tsuruo T, Minato N, Shimohama S: The 4F2hc/LAT1 complex transports L-DOPA across the blood-brain barrier. Brain Res. 2000 Oct 6;879(1-2):115-21. doi: 10.1016/s0006-8993(00)02758-x. [PubMed:11011012 ]
Di Stefano A, Mosciatti B, Cingolani GM, Giorgioni G, Ricciutelli M, Cacciatore I, Sozio P, Claudi F: Dimeric L-dopa derivatives as potential prodrugs. Bioorg Med Chem Lett. 2001 Apr 23;11(8):1085-8. doi: 10.1016/s0960-894x(01)00140-8. [PubMed:11327596 ]
Goldstein DS, Eisenhofer G, Kopin IJ: Sources and significance of plasma levels of catechols and their metabolites in humans. J Pharmacol Exp Ther. 2003 Jun;305(3):800-11. doi: 10.1124/jpet.103.049270. Epub 2003 Mar 20. [PubMed:12649306 ]
Shen H, Kannari K, Yamato H, Arai A, Matsunaga M: Effects of benserazide on L-DOPA-derived extracellular dopamine levels and aromatic L-amino acid decarboxylase activity in the striatum of 6-hydroxydopamine-lesioned rats. Tohoku J Exp Med. 2003 Mar;199(3):149-59. doi: 10.1620/tjem.199.149. [PubMed:12703659 ]
Dousa MK, Weinshilboum RM, Muenter MD, Offord KP, Decker PA, Tyce GM: L-DOPA biotransformation: correlations of dosage, erythrocyte catechol O-methyltransferase and platelet SULT1A3 activities with metabolic pathways in Parkinsonian patients. J Neural Transm (Vienna). 2003 Aug;110(8):899-910. doi: 10.1007/s00702-003-0001-2. [PubMed:12898345 ]
Blandini F, Nappi G, Fancellu R, Mangiagalli A, Samuele A, Riboldazzi G, Calandrella D, Pacchetti C, Bono G, Martignoni E: Modifications of plasma and platelet levels of L-DOPA and its direct metabolites during treatment with tolcapone or entacapone in patients with Parkinson's disease. J Neural Transm (Vienna). 2003 Aug;110(8):911-22. doi: 10.1007/s00702-003-0004-z. [PubMed:12898346 ]
Pinho MJ, Serrao MP, Gomes P, Hopfer U, Jose PA, Soares-da-Silva P: Over-expression of renal LAT1 and LAT2 and enhanced L-DOPA uptake in SHR immortalized renal proximal tubular cells. Kidney Int. 2004 Jul;66(1):216-26. doi: 10.1111/j.1523-1755.2004.00722.x. [PubMed:15200428 ]
Chalimoniuk M, Stepien A: Influence of the therapy with pergolide mesylate plus L-DOPA and with L-DOPA alone on serum cGMP level in PD patients. Pol J Pharmacol. 2004 Sep-Oct;56(5):647-50. [PubMed:15591656 ]
Cools R: Dopaminergic modulation of cognitive function-implications for L-DOPA treatment in Parkinson's disease. Neurosci Biobehav Rev. 2006;30(1):1-23. doi: 10.1016/j.neubiorev.2005.03.024. Epub 2005 Jun 1. [PubMed:15935475 ]
Mercuri NB, Bernardi G: The 'magic' of L-dopa: why is it the gold standard Parkinson's disease therapy? Trends Pharmacol Sci. 2005 Jul;26(7):341-4. doi: 10.1016/j.tips.2005.05.002. [PubMed:15936832 ]
Vassiliou AG, Vassilacopoulou D, Fragoulis EG: Purification of an endogenous inhibitor of L-Dopa decarboxylase activity from human serum. Neurochem Res. 2005 May;30(5):641-9. doi: 10.1007/s11064-005-2752-7. [PubMed:16176068 ]

Showing metabocard for L-Dopa (MMDBc0000498)

MOL for #<Metabolite:0x00007f46bb331608>

3D MOL for #<Metabolite:0x00007f46bb331608>

3D SDF for #<Metabolite:0x00007f46bb331608>

3D-SDF for #<Metabolite:0x00007f46bb331608>

PDB for #<Metabolite:0x00007f46bb331608>

3D PDB for #<Metabolite:0x00007f46bb331608>

SMILES for #<Metabolite:0x00007f46bb331608>

INCHI for #<Metabolite:0x00007f46bb331608>

Structure for #<Metabolite:0x00007f46bb331608>

3D Structure for #<Metabolite:0x00007f46bb331608>