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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (11)transporters (2) Show 13 proteins XML

enzymes (11)transporters (2) Show 13 proteins

Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2023-07-07 20:53:56 UTC

HMDB ID

HMDB0000181

Secondary Accession Numbers

HMDB00181

Metabolite Identification

Common Name

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>
HMDB0000181

> <DATABASE_NAME>
hmdb

> <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

View in JSmol View NMR Assignments View Stereo Labels

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

59-92-7

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 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

Physiological effect

Health effect

Digestive system disorder

Hepatobiliary disorder

Hepatic disorder

Liver damage (PMID: 31434538)

Nervous system disorder

Nerve damage (PMID: 31434538)

Organoleptic effect

Odor

Odorless

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 17031479)
Cerebrospinal Fluid (CSF) (PMID: 3127089)
Cerebrospinal fluid (HMDB: HMDB0000181)

Tissue substructure

Muscle (HMDB: HMDB0000181)

Cell

Hematocyte

Platelet (HMDB: HMDB0000181)

Organ substructure

Adrenal medulla (HMDB: HMDB0000181)

Organ

Tissue

Epithelium

Epidermis (HMDB: HMDB0000181)

Muscle tissue

Skeletal muscle (HMDB: HMDB0000181)

Excreta

Biofluid or Excreta

Urine (PMID: 24023812)
Feces (PMID: 29808030)

Cellular substructure

Cytoplasm (HMDB: HMDB0000181)
Extracellular (HMDB: HMDB0000181)

Striatum (HMDB: HMDB0000181)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0000181)

Source

Exogenous

Exogenous (HMDB: HMDB0000181)

Food

Food (HMDB: HMDB0000181)

Animal origin

Poultry

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Herb and spice mixture

Curry powder (FooDB: FOOD00678)

Herbs and Spices (FooDB: FOOD00866)

Vegetable

Cabbage

Onion-family vegetable

Allium (FooDB: FOOD00005)
Garden onion (FooDB: FOOD00006)
Leek (FooDB: FOOD00007)
Garden onion (var.) (FooDB: FOOD00226)
Shallot (FooDB: FOOD00243)
Wild leek (FooDB: FOOD00396)
Red onion (FooDB: FOOD00962)
Green onion (FooDB: FOOD00963)
Onion-family vegetables (FooDB: FOOD00855)

Root vegetable

Shoot vegetable

Leaf vegetable

Common beet (FooDB: FOOD00025)
Endive (FooDB: FOOD00048)
Rocket salad (ssp.) (FooDB: FOOD00077)
Swamp cabbage (FooDB: FOOD00091)
Lettuce (FooDB: FOOD00095)
Garden cress (FooDB: FOOD00099)
Spinach (FooDB: FOOD00178)
Swiss chard (FooDB: FOOD00237)
Chicory leaves (FooDB: FOOD00250)
Garland chrysanthemum (FooDB: FOOD00333)
Corn salad (FooDB: FOOD00340)
Jute (FooDB: FOOD00389)
Lambsquarters (FooDB: FOOD00394)
Malabar spinach (FooDB: FOOD00404)
New Zealand spinach (FooDB: FOOD00415)
Yautia (FooDB: FOOD00510)
Ostrich fern (FooDB: FOOD00556)
Romaine lettuce (FooDB: FOOD00888)
Iceberg lettuce (FooDB: FOOD00973)
Pea shoots (FooDB: FOOD00975)
Yau choy (FooDB: FOOD00976)
Water spinach (FooDB: FOOD00977)
Rocket salad (FooDB: FOOD00244)
Green vegetables (FooDB: FOOD00872)

Fruit vegetable

Pepper (FooDB: FOOD00040)
Olive (FooDB: FOOD00121)
Avocado (FooDB: FOOD00130)
Garden tomato (FooDB: FOOD00171)
Cherry tomato (FooDB: FOOD00172)
Garden tomato (var.) (FooDB: FOOD00173)
Eggplant (FooDB: FOOD00174)
Pepper (C. baccatum) (FooDB: FOOD00231)
Pepper (C. chinense) (FooDB: FOOD00232)
Pepper (Capsicum) (FooDB: FOOD00233)
Groundcherry (FooDB: FOOD00371)
Pepper (C. frutescens) (FooDB: FOOD00428)
Mexican groundcherry (FooDB: FOOD00491)
Pepper (C. pubescens) (FooDB: FOOD00849)
Green bell pepper (FooDB: FOOD00877)
Yellow bell pepper (FooDB: FOOD00878)
Orange bell pepper (FooDB: FOOD00879)
Red bell pepper (FooDB: FOOD00880)
Italian sweet red pepper (FooDB: FOOD00881)
Jalapeno pepper (FooDB: FOOD00955)
Cubanelle pepper (FooDB: FOOD00971)

Tuber

Stalk vegetable

Other vegetable

Giant butterbur (FooDB: FOOD00314)
Carob (FooDB: FOOD00321)
Chinese water chestnut (FooDB: FOOD00332)
Horseradish tree (FooDB: FOOD00379)
Sacred lotus (FooDB: FOOD00402)
Nopal (FooDB: FOOD00416)
Okra (FooDB: FOOD00420)
Sesbania flower (FooDB: FOOD00469)
Agave (FooDB: FOOD00563)
Narrowleaf cattail (FooDB: FOOD00564)
Heart of palm (FooDB: FOOD00718)
Tree fern (FooDB: FOOD00797)

Mushroom

Castanospermum australe (FooDB: FOOD00893)
Gentiana lutea (FooDB: FOOD00894)
Juniperus communis (FooDB: FOOD00895)
Albizia gummifera (FooDB: FOOD00896)

Brassica

Brassicas (FooDB: FOOD00857)

Fruit

Tropical fruit

Citrus

Lime (FooDB: FOOD00053)
Lemon (FooDB: FOOD00054)
Pummelo (FooDB: FOOD00055)
Mandarin orange (Clementine, Tangerine) (FooDB: FOOD00056)
Sweet orange (FooDB: FOOD00057)
Grapefruit/Pummelo hybrid (FooDB: FOOD00255)
Grapefruit (FooDB: FOOD00256)
Persian lime (FooDB: FOOD00543)
Sour orange (FooDB: FOOD00918)
Mikan (FooDB: FOOD00932)
Clementine (FooDB: FOOD00959)
Citrus (FooDB: FOOD00859)

Pome

Berry

Black crowberry (FooDB: FOOD00075)
Strawberry (FooDB: FOOD00083)
Black huckleberry (FooDB: FOOD00084)
Sea-buckthornberry (FooDB: FOOD00087)
Mulberry (FooDB: FOOD00116)
Black mulberry (FooDB: FOOD00117)
Black chokeberry (FooDB: FOOD00136)
Blackcurrant (FooDB: FOOD00155)
Redcurrant (FooDB: FOOD00156)
Gooseberry (FooDB: FOOD00157)
Cloudberry (FooDB: FOOD00161)
Red raspberry (FooDB: FOOD00162)
Black raspberry (FooDB: FOOD00163)
Black elderberry (FooDB: FOOD00166)
Rowanberry (FooDB: FOOD00176)
Vaccinium (Blueberry, Cranberry, Huckleberry) (FooDB: FOOD00188)
Lowbush blueberry (FooDB: FOOD00189)
Sparkleberry (FooDB: FOOD00190)
Highbush blueberry (FooDB: FOOD00191)
American cranberry (FooDB: FOOD00192)
Bilberry (FooDB: FOOD00193)
Lingonberry (FooDB: FOOD00194)
Muscadine grape (FooDB: FOOD00203)
Common grape (FooDB: FOOD00204)
Arctic blackberry (FooDB: FOOD00207)
Bayberry (FooDB: FOOD00209)
Elliott's blueberry (FooDB: FOOD00210)
Canada blueberry (FooDB: FOOD00211)
Bog bilberry (FooDB: FOOD00212)
Buffalo currant (FooDB: FOOD00213)
European cranberry (FooDB: FOOD00217)
Deerberry (FooDB: FOOD00218)
Cascade huckleberry (FooDB: FOOD00220)
Oval-leaf huckleberry (FooDB: FOOD00221)
Evergreen huckleberry (FooDB: FOOD00222)
Red huckleberry (FooDB: FOOD00223)
Summer grape (FooDB: FOOD00227)
Fox grape (FooDB: FOOD00228)
Half-highbush blueberry (FooDB: FOOD00248)
Jostaberry (FooDB: FOOD00257)
Sweet rowanberry (FooDB: FOOD00265)
Skunk currant (FooDB: FOOD00267)
Squashberry (FooDB: FOOD00344)
Elderberry (FooDB: FOOD00358)
Grape (FooDB: FOOD00369)
Alaska blueberry (FooDB: FOOD00380)
Loganberry (FooDB: FOOD00400)
Ohelo berry (FooDB: FOOD00419)
Salmonberry (FooDB: FOOD00456)
Strawberry guava (FooDB: FOOD00482)
Boysenberry (FooDB: FOOD00542)
Chinese bayberry (FooDB: FOOD00852)
Saskatoon berry (FooDB: FOOD00884)
Nanking cherry (FooDB: FOOD00885)
Rabbiteye blueberry (FooDB: FOOD00898)
Blackberry (FooDB: FOOD00906)
Partridge berry (FooDB: FOOD00931)
Green grape (FooDB: FOOD00964)
Red grape (FooDB: FOOD00965)
Black plum (FooDB: FOOD00966)
Black raisin (FooDB: FOOD00968)
Chinese plum (FooDB: FOOD00978)
Green plum (FooDB: FOOD00979)
Wampee (FooDB: FOOD00980)
Goji (FooDB: FOOD00982)
Monk fruit (FooDB: FOOD00983)
Hawthorn (FooDB: FOOD00985)
Lantern fruit (FooDB: FOOD00986)
Cape gooseberry (FooDB: FOOD00988)
Rubus (Blackberry, Raspberry) (FooDB: FOOD00160)

Other fruit

Fig (FooDB: FOOD00081)
Date (FooDB: FOOD00135)
Jujube (FooDB: FOOD00388)

Drupe

Prunus (Cherry, Plum) (FooDB: FOOD00143)
Apricot (FooDB: FOOD00144)
Sweet cherry (FooDB: FOOD00145)
Sour cherry (FooDB: FOOD00146)
European plum (FooDB: FOOD00147)
Peach (FooDB: FOOD00149)
Nectarine (FooDB: FOOD00229)
Peach (var.) (FooDB: FOOD00230)
Common chokecherry (FooDB: FOOD00562)

Fruits (FooDB: FOOD00871)

Nut

Cashew nut (FooDB: FOOD00011)
Peanut (FooDB: FOOD00016)
Brazil nut (FooDB: FOOD00024)
Pecan nut (FooDB: FOOD00044)
Chestnut (FooDB: FOOD00045)
Common hazelnut (FooDB: FOOD00062)
Black walnut (FooDB: FOOD00093)
Common walnut (FooDB: FOOD00094)
Pine nut (FooDB: FOOD00138)
Pistachio (FooDB: FOOD00140)
Almond (FooDB: FOOD00148)
Macadamia nut (M. tetraphylla) (FooDB: FOOD00225)
Japanese walnut (FooDB: FOOD00240)
Acorn (FooDB: FOOD00282)
Beech nut (FooDB: FOOD00299)
Butternut (FooDB: FOOD00316)
Chinese chestnut (FooDB: FOOD00331)
European chestnut (FooDB: FOOD00363)
Hazelnut (FooDB: FOOD00376)
Hickory nut (FooDB: FOOD00377)
Japanese chestnut (FooDB: FOOD00385)
Pili nut (FooDB: FOOD00432)
Colorado pinyon (FooDB: FOOD00433)
Macadamia nut (FooDB: FOOD00525)
Walnut (FooDB: FOOD00608)
Mixed nuts (FooDB: FOOD00771)
Nuts (FooDB: FOOD00869)

Cereal and cereal product

Cereal

Cereal product

Dough

Sourdough (FooDB: FOOD00275)

Leavened bread

Flat bread

Other bread

Potato bread (FooDB: FOOD00811)
Other bread (FooDB: FOOD00269)

Sweet bread

Raisin bread (FooDB: FOOD00817)

Cereals and cereal products (FooDB: FOOD00858)

Pulse

Pea

Lentil

Lentils (FooDB: FOOD00098)

Other pulse

Lupine (FooDB: FOOD00104)
White lupine (FooDB: FOOD00403)

Bean

Green lentil (FooDB: FOOD00970)
Pulses (FooDB: FOOD00867)

Gourd

Watermelon (FooDB: FOOD00052)
Muskmelon (FooDB: FOOD00064)
Cucumber (FooDB: FOOD00065)
Cucurbita (FooDB: FOOD00066)
Bitter gourd (FooDB: FOOD00115)
Winter squash (FooDB: FOOD00283)
Butternut squash (FooDB: FOOD00317)
Calabash (FooDB: FOOD00318)
Chayote (FooDB: FOOD00325)
Towel gourd (FooDB: FOOD00492)
Wax gourd (FooDB: FOOD00499)
Tinda (FooDB: FOOD00559)
Horned melon (FooDB: FOOD00761)
Sunburst squash (pattypan squash) (FooDB: FOOD00874)
Green zucchini (FooDB: FOOD00875)
Yellow zucchini (FooDB: FOOD00876)
Japanese pumpkin (FooDB: FOOD00886)
Acorn squash (FooDB: FOOD00972)
Cantaloupe melon (FooDB: FOOD00984)

Coffee and coffee product

Coffee

Arabica coffee (FooDB: FOOD00059)
Robusta coffee (FooDB: FOOD00060)

Soy

Soy bean (FooDB: FOOD00085)

Soy product

Dish

Other dish

Taco shell (FooDB: FOOD00991)
Tostada shell (FooDB: FOOD00992)

Tea

Herbal tea

Hibiscus tea (FooDB: FOOD00723)
Greenthread tea (FooDB: FOOD00820)

Baking good

Wrapper

Wonton wrapper (FooDB: FOOD00818)

Abalone (FooDB: FOOD00279)
Conch (FooDB: FOOD00611)

Cocoa and cocoa product

Cocoa

Cocoa bean (FooDB: FOOD00182)

Environmental

Wastewater (HMDB: HMDB0000181)

Endogenous

Endogenous (HMDB: HMDB0000181)

Plant

Animal

Animal (HMDB: HMDB0000181)

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Tryptophan Metabolism (HMDB: HMDB0000181)
Tyrosine Metabolism (HMDB: HMDB0000181)
Catecholamine Biosynthesis (HMDB: HMDB0000181)
Catecholamine Biosynthesis (HMDB: HMDB0000181)
Isoquinoline Alkaloid Biosynthesis (PathBank: SMP0063471)

Disease pathway

Aromatic L-Aminoacid Decarboxylase Deficiency (HMDB: HMDB0000181)
Tyrosinemia, Transient, of the Newborn (PathBank: SMP0120779)
Tyrosine Hydroxylase Deficiency (PathBank: SMP0120562)
Hawkinsinuria (PathBank: SMP0120711)
Tyrosinemia Type I (PathBank: SMP0120729)
Alkaptonuria (PathBank: SMP0120453)
Dopamine beta-Hydroxylase Deficiency (PathBank: SMP0120563)
Monoamine Oxidase-A Deficiency (MAO-A) (PathBank: SMP0120817)

Drug action pathway

Disulfiram Action Pathway (HMDB: HMDB0000181)
Disulfiram Action Pathway (PathBank: SMP0000429)

Role

Industrial application

Pharmaceutical industry

Biomarker

Alzheimer's Disease (MarkerDB: MDB00000086)

Antidyskinesia agent (HMDB: HMDB0000181)
Miotic (HMDB: HMDB0000181)

Agriculture

Growth agent

Plant growth retardant (HMDB: HMDB0000181)

Manufacturing industry

Material processing agent

Coloring agent

Fluorescent agent

Biological role

Human metabolite (HMDB: HMDB0000181)
Hapten (HMDB: HMDB0000181)
Dopaminergic agent (HMDB: HMDB0000181)
Allelochemical (HMDB: HMDB0000181)
Waste product (PMID: 35448883)
Anorexic (HMDB: HMDB0000181)
Anti encephalopathic (HMDB: HMDB0000181)
Anti feedant (HMDB: HMDB0000181)
Anti morphinic (HMDB: HMDB0000181)
Anti neuroleptic (HMDB: HMDB0000181)
Anti Parkinsonian (HMDB: HMDB0000181)
Anti reserpine (HMDB: HMDB0000181)
Anti tremor (HMDB: HMDB0000181)
Aphrodisiac (HMDB: HMDB0000181)
Arrhythmigenic (HMDB: HMDB0000181)
Cardiovascular (HMDB: HMDB0000181)
Central nervous system active (HMDB: HMDB0000181)
Depressant (HMDB: HMDB0000181)
Emetic (HMDB: HMDB0000181)
Hypertensive (HMDB: HMDB0000181)
Hypotensive (HMDB: HMDB0000181)
Insectifuge (HMDB: HMDB0000181)
Natriuretic (HMDB: HMDB0000181)

Indirect biological role

Metabotoxin

Neurotoxin (HMDB: HMDB0000181)
Neurotoxin (HMDB: HMDB0000181)

Environmental role

Environmental contaminant (HMDB: HMDB0000181)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	285 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	5 mg/mL	Not Available
LogP	-2.39	SANGSTER (1993)

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M-H]-	Not Available	140.3	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000007
[M+H]+	Not Available	147.1	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000007

Predicted Molecular Properties

Property	Value	Source
Water Solubility	3.3 g/L	ALOGPS
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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	146.425	31661259
DarkChem	[M-H]-	142.582	31661259
AllCCS	[M+H]+	143.995	32859911
AllCCS	[M-H]-	141.185	32859911
DeepCCS	[M+H]+	142.17	30932474
DeepCCS	[M-H]-	139.774	30932474
DeepCCS	[M-2H]-	173.823	30932474
DeepCCS	[M+Na]+	148.433	30932474
AllCCS	[M+H]+	144.0	32859911
AllCCS	[M+H-H2O]+	140.0	32859911
AllCCS	[M+NH4]+	147.8	32859911
AllCCS	[M+Na]+	148.8	32859911
AllCCS	[M-H]-	141.2	32859911
AllCCS	[M+Na-2H]-	141.8	32859911
AllCCS	[M+HCOO]-	142.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
L-Dopa	N[C@@H](CC1=CC=C(O)C(O)=C1)C(O)=O	3369.5	Standard polar	33892256
L-Dopa	N[C@@H](CC1=CC=C(O)C(O)=C1)C(O)=O	2121.4	Standard non polar	33892256
L-Dopa	N[C@@H](CC1=CC=C(O)C(O)=C1)C(O)=O	2029.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
L-Dopa,1TMS,isomer #1	C[Si](C)(C)OC1=CC=C(C[C@H](N)C(=O)O)C=C1O	2078.4	Semi standard non polar	33892256
L-Dopa,1TMS,isomer #2	C[Si](C)(C)OC1=CC(C[C@H](N)C(=O)O)=CC=C1O	2081.8	Semi standard non polar	33892256
L-Dopa,1TMS,isomer #3	C[Si](C)(C)OC(=O)[C@@H](N)CC1=CC=C(O)C(O)=C1	2090.3	Semi standard non polar	33892256
L-Dopa,1TMS,isomer #4	C[Si](C)(C)N[C@@H](CC1=CC=C(O)C(O)=C1)C(=O)O	2168.5	Semi standard non polar	33892256
L-Dopa,2TMS,isomer #1	C[Si](C)(C)OC(=O)[C@@H](N)CC1=CC=C(O[Si](C)(C)C)C(O)=C1	2016.4	Semi standard non polar	33892256
L-Dopa,2TMS,isomer #2	C[Si](C)(C)OC1=CC=C(C[C@H](N)C(=O)O)C=C1O[Si](C)(C)C	2078.3	Semi standard non polar	33892256
L-Dopa,2TMS,isomer #3	C[Si](C)(C)N[C@@H](CC1=CC=C(O[Si](C)(C)C)C(O)=C1)C(=O)O	2110.6	Semi standard non polar	33892256
L-Dopa,2TMS,isomer #4	C[Si](C)(C)OC(=O)[C@@H](N)CC1=CC=C(O)C(O[Si](C)(C)C)=C1	2020.1	Semi standard non polar	33892256
L-Dopa,2TMS,isomer #5	C[Si](C)(C)N[C@@H](CC1=CC=C(O)C(O[Si](C)(C)C)=C1)C(=O)O	2109.7	Semi standard non polar	33892256
L-Dopa,2TMS,isomer #6	C[Si](C)(C)N[C@@H](CC1=CC=C(O)C(O)=C1)C(=O)O[Si](C)(C)C	2113.0	Semi standard non polar	33892256
L-Dopa,2TMS,isomer #7	C[Si](C)(C)N([C@@H](CC1=CC=C(O)C(O)=C1)C(=O)O)[Si](C)(C)C	2300.0	Semi standard non polar	33892256
L-Dopa,3TMS,isomer #1	C[Si](C)(C)OC(=O)[C@@H](N)CC1=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C1	2054.8	Semi standard non polar	33892256
L-Dopa,3TMS,isomer #2	C[Si](C)(C)N[C@@H](CC1=CC=C(O[Si](C)(C)C)C(O)=C1)C(=O)O[Si](C)(C)C	2067.8	Semi standard non polar	33892256
L-Dopa,3TMS,isomer #3	C[Si](C)(C)N[C@@H](CC1=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C1)C(=O)O	2106.7	Semi standard non polar	33892256
L-Dopa,3TMS,isomer #4	C[Si](C)(C)OC1=CC=C(C[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)C=C1O	2248.2	Semi standard non polar	33892256
L-Dopa,3TMS,isomer #5	C[Si](C)(C)N[C@@H](CC1=CC=C(O)C(O[Si](C)(C)C)=C1)C(=O)O[Si](C)(C)C	2047.1	Semi standard non polar	33892256
L-Dopa,3TMS,isomer #6	C[Si](C)(C)OC1=CC(C[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)=CC=C1O	2240.2	Semi standard non polar	33892256
L-Dopa,3TMS,isomer #7	C[Si](C)(C)OC(=O)[C@H](CC1=CC=C(O)C(O)=C1)N([Si](C)(C)C)[Si](C)(C)C	2262.9	Semi standard non polar	33892256
L-Dopa,4TMS,isomer #1	C[Si](C)(C)N[C@@H](CC1=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C1)C(=O)O[Si](C)(C)C	2108.8	Semi standard non polar	33892256
L-Dopa,4TMS,isomer #1	C[Si](C)(C)N[C@@H](CC1=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C1)C(=O)O[Si](C)(C)C	2133.4	Standard non polar	33892256
L-Dopa,4TMS,isomer #1	C[Si](C)(C)N[C@@H](CC1=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C1)C(=O)O[Si](C)(C)C	2175.1	Standard polar	33892256
L-Dopa,4TMS,isomer #2	C[Si](C)(C)OC(=O)[C@H](CC1=CC=C(O[Si](C)(C)C)C(O)=C1)N([Si](C)(C)C)[Si](C)(C)C	2257.1	Semi standard non polar	33892256
L-Dopa,4TMS,isomer #2	C[Si](C)(C)OC(=O)[C@H](CC1=CC=C(O[Si](C)(C)C)C(O)=C1)N([Si](C)(C)C)[Si](C)(C)C	2259.3	Standard non polar	33892256
L-Dopa,4TMS,isomer #2	C[Si](C)(C)OC(=O)[C@H](CC1=CC=C(O[Si](C)(C)C)C(O)=C1)N([Si](C)(C)C)[Si](C)(C)C	2277.6	Standard polar	33892256
L-Dopa,4TMS,isomer #3	C[Si](C)(C)OC1=CC=C(C[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)C=C1O[Si](C)(C)C	2271.0	Semi standard non polar	33892256
L-Dopa,4TMS,isomer #3	C[Si](C)(C)OC1=CC=C(C[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)C=C1O[Si](C)(C)C	2215.0	Standard non polar	33892256
L-Dopa,4TMS,isomer #3	C[Si](C)(C)OC1=CC=C(C[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)C=C1O[Si](C)(C)C	2314.0	Standard polar	33892256
L-Dopa,4TMS,isomer #4	C[Si](C)(C)OC(=O)[C@H](CC1=CC=C(O)C(O[Si](C)(C)C)=C1)N([Si](C)(C)C)[Si](C)(C)C	2250.3	Semi standard non polar	33892256
L-Dopa,4TMS,isomer #4	C[Si](C)(C)OC(=O)[C@H](CC1=CC=C(O)C(O[Si](C)(C)C)=C1)N([Si](C)(C)C)[Si](C)(C)C	2282.7	Standard non polar	33892256
L-Dopa,4TMS,isomer #4	C[Si](C)(C)OC(=O)[C@H](CC1=CC=C(O)C(O[Si](C)(C)C)=C1)N([Si](C)(C)C)[Si](C)(C)C	2326.3	Standard polar	33892256
L-Dopa,5TMS,isomer #1	C[Si](C)(C)OC(=O)[C@H](CC1=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C1)N([Si](C)(C)C)[Si](C)(C)C	2347.9	Semi standard non polar	33892256
L-Dopa,5TMS,isomer #1	C[Si](C)(C)OC(=O)[C@H](CC1=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C1)N([Si](C)(C)C)[Si](C)(C)C	2238.7	Standard non polar	33892256
L-Dopa,5TMS,isomer #1	C[Si](C)(C)OC(=O)[C@H](CC1=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C1)N([Si](C)(C)C)[Si](C)(C)C	2155.9	Standard polar	33892256
L-Dopa,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C(C[C@H](N)C(=O)O)C=C1O	2337.1	Semi standard non polar	33892256
L-Dopa,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC(C[C@H](N)C(=O)O)=CC=C1O	2338.8	Semi standard non polar	33892256
L-Dopa,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=O)[C@@H](N)CC1=CC=C(O)C(O)=C1	2337.7	Semi standard non polar	33892256
L-Dopa,1TBDMS,isomer #4	CC(C)(C)[Si](C)(C)N[C@@H](CC1=CC=C(O)C(O)=C1)C(=O)O	2418.5	Semi standard non polar	33892256
L-Dopa,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)[C@@H](N)CC1=CC=C(O[Si](C)(C)C(C)(C)C)C(O)=C1	2555.0	Semi standard non polar	33892256
L-Dopa,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC=C(C[C@H](N)C(=O)O)C=C1O[Si](C)(C)C(C)(C)C	2582.0	Semi standard non polar	33892256
L-Dopa,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N[C@@H](CC1=CC=C(O[Si](C)(C)C(C)(C)C)C(O)=C1)C(=O)O	2645.6	Semi standard non polar	33892256
L-Dopa,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC(=O)[C@@H](N)CC1=CC=C(O)C(O[Si](C)(C)C(C)(C)C)=C1	2517.0	Semi standard non polar	33892256
L-Dopa,2TBDMS,isomer #5	CC(C)(C)[Si](C)(C)N[C@@H](CC1=CC=C(O)C(O[Si](C)(C)C(C)(C)C)=C1)C(=O)O	2621.4	Semi standard non polar	33892256
L-Dopa,2TBDMS,isomer #6	CC(C)(C)[Si](C)(C)N[C@@H](CC1=CC=C(O)C(O)=C1)C(=O)O[Si](C)(C)C(C)(C)C	2583.1	Semi standard non polar	33892256
L-Dopa,2TBDMS,isomer #7	CC(C)(C)[Si](C)(C)N([C@@H](CC1=CC=C(O)C(O)=C1)C(=O)O)[Si](C)(C)C(C)(C)C	2725.3	Semi standard non polar	33892256
L-Dopa,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)[C@@H](N)CC1=CC=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C1	2751.1	Semi standard non polar	33892256
L-Dopa,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N[C@@H](CC1=CC=C(O[Si](C)(C)C(C)(C)C)C(O)=C1)C(=O)O[Si](C)(C)C(C)(C)C	2803.0	Semi standard non polar	33892256
L-Dopa,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N[C@@H](CC1=CC=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C1)C(=O)O	2854.5	Semi standard non polar	33892256
L-Dopa,3TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC1=CC=C(C[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1O	2996.0	Semi standard non polar	33892256
L-Dopa,3TBDMS,isomer #5	CC(C)(C)[Si](C)(C)N[C@@H](CC1=CC=C(O)C(O[Si](C)(C)C(C)(C)C)=C1)C(=O)O[Si](C)(C)C(C)(C)C	2767.2	Semi standard non polar	33892256
L-Dopa,3TBDMS,isomer #6	CC(C)(C)[Si](C)(C)OC1=CC(C[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=CC=C1O	2971.8	Semi standard non polar	33892256
L-Dopa,3TBDMS,isomer #7	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CC1=CC=C(O)C(O)=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2911.8	Semi standard non polar	33892256
L-Dopa,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N[C@@H](CC1=CC=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C1)C(=O)O[Si](C)(C)C(C)(C)C	3007.9	Semi standard non polar	33892256
L-Dopa,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N[C@@H](CC1=CC=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C1)C(=O)O[Si](C)(C)C(C)(C)C	2876.1	Standard non polar	33892256
L-Dopa,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N[C@@H](CC1=CC=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C1)C(=O)O[Si](C)(C)C(C)(C)C	2659.6	Standard polar	33892256
L-Dopa,4TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CC1=CC=C(O[Si](C)(C)C(C)(C)C)C(O)=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3181.1	Semi standard non polar	33892256
L-Dopa,4TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CC1=CC=C(O[Si](C)(C)C(C)(C)C)C(O)=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3011.2	Standard non polar	33892256
L-Dopa,4TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CC1=CC=C(O[Si](C)(C)C(C)(C)C)C(O)=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2678.2	Standard polar	33892256
L-Dopa,4TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=CC=C(C[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1O[Si](C)(C)C(C)(C)C	3214.9	Semi standard non polar	33892256
L-Dopa,4TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=CC=C(C[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1O[Si](C)(C)C(C)(C)C	2942.8	Standard non polar	33892256
L-Dopa,4TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=CC=C(C[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1O[Si](C)(C)C(C)(C)C	2695.7	Standard polar	33892256
L-Dopa,4TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CC1=CC=C(O)C(O[Si](C)(C)C(C)(C)C)=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3150.8	Semi standard non polar	33892256
L-Dopa,4TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CC1=CC=C(O)C(O[Si](C)(C)C(C)(C)C)=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3034.3	Standard non polar	33892256
L-Dopa,4TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CC1=CC=C(O)C(O[Si](C)(C)C(C)(C)C)=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2715.4	Standard polar	33892256
L-Dopa,5TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CC1=CC=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3418.3	Semi standard non polar	33892256
L-Dopa,5TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CC1=CC=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3118.7	Standard non polar	33892256
L-Dopa,5TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CC1=CC=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2684.7	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - DOPA GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (4 TMS)	splash10-014i-0790000000-b2f7f063a2c8197c7edd	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - DOPA GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-014i-0690000000-622497b3104c6082a45d	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - DOPA GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (4 TMS)	splash10-00xr-9350000000-b0cc4636931d2de64d81	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - DOPA GC-MS (4 TMS)	splash10-014i-0590000000-4474e81e4226bb4e1d4c	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - DOPA GC-EI-TOF (Non-derivatized)	splash10-014i-0790000000-b2f7f063a2c8197c7edd	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - DOPA GC-EI-TOF (Non-derivatized)	splash10-014i-0690000000-622497b3104c6082a45d	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - DOPA GC-EI-TOF (Non-derivatized)	splash10-00xr-9350000000-b0cc4636931d2de64d81	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - DOPA GC-MS (Non-derivatized)	splash10-014i-0590000000-4474e81e4226bb4e1d4c	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - DOPA GC-EI-TOF (Non-derivatized)	splash10-014i-1890000000-646d209fa1943582a336	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - DOPA GC-EI-TOF (Non-derivatized)	splash10-014i-0690000000-720ed87e98a0d9f1721d	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - DOPA GC-MS (Non-derivatized) - 70eV, Positive	splash10-0fk9-3900000000-266d9baeda773fe1fb22	2017-08-28	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - DOPA GC-MS (3 TMS) - 70eV, Positive	splash10-0002-4193000000-8c76bf85d8a897e9403c	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - DOPA GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - DOPA GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - DOPA GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - DOPA GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - DOPA GC-MS (TMS_1_4) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - DOPA GC-MS (TMS_2_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - DOPA GC-MS (TMS_2_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - DOPA GC-MS (TMS_2_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - DOPA GC-MS (TMS_2_4) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - DOPA GC-MS (TMS_2_5) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - DOPA GC-MS (TMS_2_6) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - DOPA GC-MS (TMS_2_7) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - DOPA GC-MS (TMS_3_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum

MS/MS Spectra

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

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Experimental 1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	2012-12-04	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Experimental 2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	2012-12-05	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-03	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

Biospecimen Locations

Blood
Cerebrospinal Fluid (CSF)
Feces
Urine

Tissue Locations

Adrenal Medulla
Bladder
Brain
Epidermis
Intestine
Neuron
Placenta
Platelet
Skeletal Muscle

Pathways

Name	SMPDB/PathBank	KEGG
Tyrosine metabolism	Not Available
Tyrosine metabolism	Not Available
Aromatic L-Aminoacid Decarboxylase Deficiency		Not Available
Tyrosine hydroxylase deficiency		Not Available
Alkaptonuria		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.00723 +/- 0.00097 uM	Adult (>18 years old)	Both	Normal	Geigy Scientific ...	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.0035 +/- 0.0009 uM	Adult (>18 years old)	Not Specified	Normal	3127089	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	<0.025 uM	Children (1-13 years old)	Male	Normal	18502672	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	29808030	details
Urine	Detected and Quantified	0.01-0.15 umol/mmol creatinine	Newborn (0-30 days old)	Both	Normal	32340350	details
Urine	Detected and Quantified	0.04(0.01-0.08) umol/mmol creatinine	Newborn (0-30 days old)	Female	Normal	32340350	details
Urine	Detected and Quantified	0.04(0.02-0.17) umol/mmol creatinine	Newborn (0-30 days old)	Male	Normal	32340350	details
Urine	Detected and Quantified	0.0833 +/- 0.0238 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Normal	Analysis of 30 no...	details
Urine	Detected and Quantified	0.02 (0.01-0.04) umol/mmol creatinine	Adult (>18 years old)	Both	Normal	24023812	details
Urine	Detected and Quantified	0.00500-0.217 umol/mmol creatinine	Children (1-13 years old)	Female	Normal	9686366	details
Urine	Detected and Quantified	0.008 (0.0036-0.0138) umol/mmol creatinine	Children (1-13 years old)	Both	Normal	Geigy Scientific ... West Cadwell, N.J... Basel, Switzerlan...	details
Urine	Detected and Quantified	0.0136 +/- 0.0033 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	Geigy Scientific ... West Cadwell, N.J... Basel, Switzerlan...	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	14.0 +/- 2.53 uM	Elderly (>65 years old)	Both	Alzheimer's disease	17031479	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	<0.001 uM	Children (1-13 years old)	Male	sepiapterin reductase deficiency	18502672	details
Urine	Detected and Quantified	0.094 +/- 0.0546 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Eosinophilic esophagitis	Analysis of 30 no...	details
Urine	Detected and Quantified	0.1135 +/- 0.1355 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Gastroesophageal reflux disease	Analysis of 30 no...	details
Urine	Detected and Quantified	8.683 umol/mmol creatinine	Children (1-13 years old)	Female	Aromatic L-amino acid decarboxylase deficiency	9686366	details
Urine	Detected and Quantified	11.38 umol/mmol creatinine	Infant (0-1 year old)	Female	Aromatic L-amino acid decarboxylase deficiency	9686366	details

Associated Disorders and Diseases

Disease References

Alzheimer's disease
Fonteh AN, Harrington RJ, Tsai A, Liao P, Harrington MG: Free amino acid and dipeptide changes in the body fluids from Alzheimer's disease subjects. Amino Acids. 2007 Feb;32(2):213-24. Epub 2006 Oct 10. [PubMed:17031479 ]
Sepiapterin reductase deficiency
Verbeek MM, Willemsen MA, Wevers RA, Lagerwerf AJ, Abeling NG, Blau N, Thony B, Vargiami E, Zafeiriou DI: Two Greek siblings with sepiapterin reductase deficiency. Mol Genet Metab. 2008 Aug;94(4):403-9. doi: 10.1016/j.ymgme.2008.04.003. Epub 2008 May 27. [PubMed:18502672 ]
Eosinophilic esophagitis
Slae, M., Huynh, H., Wishart, D.S. (2014). Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work). NA.
Aromatic L-amino acid decarboxylase deficiency
Abeling NG, van Gennip AH, Barth PG, van Cruchten A, Westra M, Wijburg FA: Aromatic L-amino acid decarboxylase deficiency: a new case with a mild clinical presentation and unexpected laboratory findings. J Inherit Metab Dis. 1998 Jun;21(3):240-2. [PubMed:9686366 ]

Associated OMIM IDs

104300 (Alzheimer's disease)
182125 (Sepiapterin reductase deficiency)
610247 (Eosinophilic esophagitis)
608643 (Aromatic L-amino acid decarboxylase deficiency)

External Links

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

VMH ID

34DHPHE

MarkerDB ID

MDB00000086

Good Scents ID

Not Available

References

Synthesis Reference

Haneda, Katsuji; Watanabe, Shiro; Takeda, Isao. Synthesis ofL-3,4-dihydroxyphenylalanine from L-tyrosine by microorganisms. Applied Microbiology (1971), 22(4), 721-2.

Material Safety Data Sheet (MSDS)

Not Available

General References

Goldstein DS, Eisenhofer G, Kopin IJ: Sources and significance of plasma levels of catechols and their metabolites in humans. J Pharmacol Exp Ther. 2003 Jun;305(3):800-11. Epub 2003 Mar 20. [PubMed:12649306 ]
Cools R: Dopaminergic modulation of cognitive function-implications for L-DOPA treatment in Parkinson's disease. Neurosci Biobehav Rev. 2006;30(1):1-23. Epub 2005 Jun 1. [PubMed:15935475 ]
de Jong AP, Kok RM, Cramers CA, Wadman SK, Haan E: A new method for the determination of L-dopa and 3-O-methyldopa in plasma and cerebrospinal fluid using gas chromatography and electron capture negative ion mass spectrometry. Clin Chim Acta. 1988 Jan 15;171(1):49-61. [PubMed:3127089 ]
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 ]
Mercuri NB, Bernardi G: The 'magic' of L-dopa: why is it the gold standard Parkinson's disease therapy? Trends Pharmacol Sci. 2005 Jul;26(7):341-4. [PubMed:15936832 ]
Goldstein DS, Hahn SH, Holmes C, Tifft C, Harvey-White J, Milstien S, Kaufman S: Monoaminergic effects of folinic acid, L-DOPA, and 5-hydroxytryptophan in dihydropteridine reductase deficiency. J Neurochem. 1995 Jun;64(6):2810-3. [PubMed:7760062 ]
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 ]
Dousa MK, Weinshilboum RM, Muenter MD, Offord KP, Decker PA, Tyce GM: L-DOPA biotransformation: correlations of dosage, erythrocyte catechol O-methyltransferase and platelet SULT1A3 activities with metabolic pathways in Parkinsonian patients. J Neural Transm (Vienna). 2003 Aug;110(8):899-910. [PubMed:12898345 ]
Di Stefano A, Mosciatti B, Cingolani GM, Giorgioni G, Ricciutelli M, Cacciatore I, Sozio P, Claudi F: Dimeric L-dopa derivatives as potential prodrugs. Bioorg Med Chem Lett. 2001 Apr 23;11(8):1085-8. [PubMed:11327596 ]
Tada K, Kudo T, Kishimoto Y: Effects of L-dopa or dopamine on human decidual prostaglandin synthesis. Acta Med Okayama. 1991 Oct;45(5):333-8. [PubMed:1755339 ]
Crivellato E, Damiani D, Mallardi F: Comparison between the L-DOPA histofluorescence procedure and the indirect immunofluorescence with anti-T6 and -HLA-DR monoclonal antibodies in visualizing Langerhans cells of human epidermis. Acta Histochem. 1990;88(1):59-64. [PubMed:2113342 ]
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. [PubMed:7371653 ]
Hyland K, Clayton PT: Aromatic L-amino acid decarboxylase deficiency: diagnostic methodology. Clin Chem. 1992 Dec;38(12):2405-10. [PubMed:1281049 ]
Vassiliou AG, Vassilacopoulou D, Fragoulis EG: Purification of an endogenous inhibitor of L-Dopa decarboxylase activity from human serum. Neurochem Res. 2005 May;30(5):641-9. [PubMed:16176068 ]
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 ]
Blandini F, Nappi G, Fancellu R, Mangiagalli A, Samuele A, Riboldazzi G, Calandrella D, Pacchetti C, Bono G, Martignoni E: Modifications of plasma and platelet levels of L-DOPA and its direct metabolites during treatment with tolcapone or entacapone in patients with Parkinson's disease. J Neural Transm (Vienna). 2003 Aug;110(8):911-22. [PubMed:12898346 ]
Shen H, Kannari K, Yamato H, Arai A, Matsunaga M: Effects of benserazide on L-DOPA-derived extracellular dopamine levels and aromatic L-amino acid decarboxylase activity in the striatum of 6-hydroxydopamine-lesioned rats. Tohoku J Exp Med. 2003 Mar;199(3):149-59. [PubMed:12703659 ]
Kageyama T, Nakamura M, Matsuo A, Yamasaki Y, Takakura Y, Hashida M, Kanai Y, Naito M, Tsuruo T, Minato N, Shimohama S: The 4F2hc/LAT1 complex transports L-DOPA across the blood-brain barrier. Brain Res. 2000 Oct 6;879(1-2):115-21. [PubMed:11011012 ]
Pinho MJ, Serrao MP, Gomes P, Hopfer U, Jose PA, Soares-da-Silva P: Over-expression of renal LAT1 and LAT2 and enhanced L-DOPA uptake in SHR immortalized renal proximal tubular cells. Kidney Int. 2004 Jul;66(1):216-26. [PubMed:15200428 ]

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

Show all enzymes and transporters

Enzymes

Enzyme Details

1. Tyrosinase

General function:: Involved in oxidoreductase activity
Specific function:: This is a copper-containing oxidase that functions in the formation of pigments such as melanins and other polyphenolic compounds. Catalyzes the rate-limiting conversions of tyrosine to DOPA, DOPA to DOPA-quinone and possibly 5,6-dihydroxyindole to indole-5,6 quinone.
Gene Name:: TYR
Uniprot ID:: P14679
Molecular weight:: 60392.69

Reactions

DOPA + Oxygen → Dopaquinone + Water	details
L-Tyrosine + Oxygen → DOPA + Water	details
DOPA + L-Tyrosine + Oxygen → Dopaquinone + DOPA + Water	details

Enzyme Details

2. Catechol O-methyltransferase

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

Enzyme Details

3. Tyrosine 3-monooxygenase

General function:: Involved in monooxygenase activity
Specific function:: Plays an important role in the physiology of adrenergic neurons.
Gene Name:: TH
Uniprot ID:: P07101
Molecular weight:: 55611.26

Reactions

L-Tyrosine + Tetrahydrobiopterin + Oxygen → DOPA + 4a-Hydroxytetrahydrobiopterin	details
Tetrahydrobiopterin + L-Tyrosine + Oxygen → DOPA + 4a-Carbinolamine tetrahydrobiopterin + Water	details

Enzyme Details

4. Aromatic-L-amino-acid decarboxylase

General function:: Involved in carboxy-lyase activity
Specific function:: Catalyzes the decarboxylation of L-3,4-dihydroxyphenylalanine (DOPA) to dopamine, L-5-hydroxytryptophan to serotonin and L-tryptophan to tryptamine.
Gene Name:: DDC
Uniprot ID:: P20711
Molecular weight:: 53893.755

Reactions

DOPA → Dopamine + CO(2)	details
DOPA → Dopamine + Carbon dioxide	details

References

BIRKMAYER W, HORNYKIEWICZ O: [The L-3,4-dioxyphenylalanine (DOPA)-effect in Parkinson-akinesia]. Wien Klin Wochenschr. 1961 Nov 10;73:787-8. [PubMed:13869404 ]

Enzyme Details

5. Cytochrome P450 2D6

General function:: Involved in monooxygenase activity
Specific function:: Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic antidepressants.
Gene Name:: CYP2D6
Uniprot ID:: P10635
Molecular weight:: 55768.94

References

Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Enzyme Details

6. D(2) dopamine receptor

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: This is one of the five types (D1 to D5) of receptors for dopamine. The activity of this receptor is mediated by G proteins which inhibit adenylyl cyclase
Gene Name:: DRD2
Uniprot ID:: P14416
Molecular weight:: 50618.9

References

Dupre KB, Eskow KL, Negron G, Bishop C: The differential effects of 5-HT(1A) receptor stimulation on dopamine receptor-mediated abnormal involuntary movements and rotations in the primed hemiparkinsonian rat. Brain Res. 2007 Jul 16;1158:135-43. Epub 2007 May 8. [PubMed:17553470 ]
Mori A, Ohashi S, Nakai M, Moriizumi T, Mitsumoto Y: Neural mechanisms underlying motor dysfunction as detected by the tail suspension test in MPTP-treated C57BL/6 mice. Neurosci Res. 2005 Mar;51(3):265-74. Epub 2005 Jan 8. [PubMed:15710490 ]
Zappia M, Annesi G, Nicoletti G, Arabia G, Annesi F, Messina D, Pugliese P, Spadafora P, Tarantino P, Carrideo S, Civitelli D, De Marco EV, Ciro-Candiano IC, Gambardella A, Quattrone A: Sex differences in clinical and genetic determinants of levodopa peak-dose dyskinesias in Parkinson disease: an exploratory study. Arch Neurol. 2005 Apr;62(4):601-5. [PubMed:15824260 ]
Kovoor A, Seyffarth P, Ebert J, Barghshoon S, Chen CK, Schwarz S, Axelrod JD, Cheyette BN, Simon MI, Lester HA, Schwarz J: D2 dopamine receptors colocalize regulator of G-protein signaling 9-2 (RGS9-2) via the RGS9 DEP domain, and RGS9 knock-out mice develop dyskinesias associated with dopamine pathways. J Neurosci. 2005 Feb 23;25(8):2157-65. [PubMed:15728856 ]
Onofrj M, Bonanni L, Thomas A: An expert opinion on safinamide in Parkinson's disease. Expert Opin Investig Drugs. 2008 Jul;17(7):1115-25. doi: 10.1517/13543784.17.7.1115 . [PubMed:18549347 ]
Deleu D, Northway MG, Hanssens Y: Clinical pharmacokinetic and pharmacodynamic properties of drugs used in the treatment of Parkinson's disease. Clin Pharmacokinet. 2002;41(4):261-309. [PubMed:11978145 ]
Koller WC, Rueda MG: Mechanism of action of dopaminergic agents in Parkinson's disease. Neurology. 1998 Jun;50(6 Suppl 6):S11-4; discussion S44-8. [PubMed:9633680 ]

Enzyme Details

7. D(4) dopamine receptor

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: This is one of the five types (D1 to D5) of receptors for dopamine. The activity of this receptor is mediated by G proteins which inhibit adenylyl cyclase
Gene Name:: DRD4
Uniprot ID:: P21917
Molecular weight:: 48359.9

References

Onofrj M, Bonanni L, Thomas A: An expert opinion on safinamide in Parkinson's disease. Expert Opin Investig Drugs. 2008 Jul;17(7):1115-25. doi: 10.1517/13543784.17.7.1115 . [PubMed:18549347 ]
Deleu D, Northway MG, Hanssens Y: Clinical pharmacokinetic and pharmacodynamic properties of drugs used in the treatment of Parkinson's disease. Clin Pharmacokinet. 2002;41(4):261-309. [PubMed:11978145 ]
Koller WC, Rueda MG: Mechanism of action of dopaminergic agents in Parkinson's disease. Neurology. 1998 Jun;50(6 Suppl 6):S11-4; discussion S44-8. [PubMed:9633680 ]

Enzyme Details

8. 4F2 cell-surface antigen heavy chain

General function:: Involved in catalytic activity
Specific function:: Required for the function of light chain amino-acid transporters. Involved in sodium-independent, high-affinity transport of large neutral amino acids such as phenylalanine, tyrosine, leucine, arginine and tryptophan. Involved in guiding and targeting of LAT1 and LAT2 to the plasma membrane. When associated with SLC7A6 or SLC7A7 acts as an arginine/glutamine exchanger, following an antiport mechanism for amino acid transport, influencing arginine release in exchange for extracellular amino acids. Plays a role in nitric oxide synthesis in human umbilical vein endothelial cells (HUVECs) via transport of L-arginine. Required for normal and neoplastic cell growth. When associated with SLC7A5/LAT1, is also involved in the transport of L-DOPA across the blood-brain barrier, and that of thyroid hormones triiodothyronine (T3) and thyroxine (T4) across the cell membrane in tissues such as placenta. Involved in the uptake of methylmercury (MeHg) when administered as the L-cysteine or D,L-homocysteine complexes, and hence plays a role in metal ion homeostasis and toxicity. When associated with SLC7A5 or SLC7A8, involved in the cellular activity of small molecular weight nitrosothiols, via the stereoselective transport of L- nitrosocysteine (L-CNSO) across the transmembrane. Together with ICAM1, regulates the transport activity LAT2 in polarized intestinal cells, by generating and delivering intracellular signals. When associated with SLC7A5, plays an important role in transporting L-leucine from the circulating blood to the retina across the inner blood-retinal barrier
Gene Name:: SLC3A2
Uniprot ID:: P08195
Molecular weight:: 67993.3

Enzyme Details

9. D(3) dopamine receptor

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: This is one of the five types (D1 to D5) of receptors for dopamine. The activity of this receptor is mediated by G proteins which inhibit adenylyl cyclase. Promotes cell proliferation
Gene Name:: DRD3
Uniprot ID:: P35462
Molecular weight:: 44224.3

References

Onofrj M, Bonanni L, Thomas A: An expert opinion on safinamide in Parkinson's disease. Expert Opin Investig Drugs. 2008 Jul;17(7):1115-25. doi: 10.1517/13543784.17.7.1115 . [PubMed:18549347 ]
Deleu D, Northway MG, Hanssens Y: Clinical pharmacokinetic and pharmacodynamic properties of drugs used in the treatment of Parkinson's disease. Clin Pharmacokinet. 2002;41(4):261-309. [PubMed:11978145 ]
Koller WC, Rueda MG: Mechanism of action of dopaminergic agents in Parkinson's disease. Neurology. 1998 Jun;50(6 Suppl 6):S11-4; discussion S44-8. [PubMed:9633680 ]

Enzyme Details

10. D(1A) dopamine receptor

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: This is one of the five types (D1 to D5) of receptors for dopamine. The activity of this receptor is mediated by G proteins which activate adenylyl cyclase
Gene Name:: DRD1
Uniprot ID:: P21728
Molecular weight:: 49292.8

References

Onofrj M, Bonanni L, Thomas A: An expert opinion on safinamide in Parkinson's disease. Expert Opin Investig Drugs. 2008 Jul;17(7):1115-25. doi: 10.1517/13543784.17.7.1115 . [PubMed:18549347 ]
Deleu D, Northway MG, Hanssens Y: Clinical pharmacokinetic and pharmacodynamic properties of drugs used in the treatment of Parkinson's disease. Clin Pharmacokinet. 2002;41(4):261-309. [PubMed:11978145 ]
Koller WC, Rueda MG: Mechanism of action of dopaminergic agents in Parkinson's disease. Neurology. 1998 Jun;50(6 Suppl 6):S11-4; discussion S44-8. [PubMed:9633680 ]

Transporters

Enzyme Details

1. Solute carrier family 15 member 1

General function:: Involved in transporter activity
Specific function:: Proton-coupled intake of oligopeptides of 2 to 4 amino acids with a preference for dipeptides. May constitute a major route for the absorption of protein digestion end-products
Gene Name:: SLC15A1
Uniprot ID:: P46059
Molecular weight:: 78805.3

References

Han HK, Rhie JK, Oh DM, Saito G, Hsu CP, Stewart BH, Amidon GL: CHO/hPEPT1 cells overexpressing the human peptide transporter (hPEPT1) as an alternative in vitro model for peptidomimetic drugs. J Pharm Sci. 1999 Mar;88(3):347-50. [PubMed:10052994 ]

Enzyme Details

2. Monocarboxylate transporter 10

General function:: Involved in transmembrane transport
Specific function:: Sodium-independent transporter that mediates the update of aromatic acid. Can function as a net efflux pathway for aromatic amino acids in the basosolateral epithelial cells
Gene Name:: SLC16A10
Uniprot ID:: Q8TF71
Molecular weight:: 55492.1

References

Kim DK, Kanai Y, Chairoungdua A, Matsuo H, Cha SH, Endou H: Expression cloning of a Na+-independent aromatic amino acid transporter with structural similarity to H+/monocarboxylate transporters. J Biol Chem. 2001 May 18;276(20):17221-8. Epub 2001 Feb 20. [PubMed:11278508 ]

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

Show all enzymes and transporters

Showing metabocard for DOPA (HMDB0000181)

MOL for HMDB0000181 (DOPA)

3D MOL for HMDB0000181 (DOPA)

3D SDF for HMDB0000181 (DOPA)

3D-SDF for HMDB0000181 (DOPA)

PDB for HMDB0000181 (DOPA)

3D PDB for HMDB0000181 (DOPA)

SMILES for HMDB0000181 (DOPA)

INCHI for HMDB0000181 (DOPA)

Structure for HMDB0000181 (DOPA)

3D Structure for HMDB0000181 (DOPA)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra

Enzymes

Reactions

Reactions

Reactions

References

References

References

References

References

References

Transporters

References

References