3-O-methyldopa (CHEBI:82913)

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CHEBI:82913 - 3-O-methyldopa

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ChEBI Name	3-O-methyldopa

ChEBI ID	CHEBI:82913

ChEBI ASCII Name	3-O-methyldopa

Definition	A L-tyrosine derivative that is the 3-methoxy derivative of L-dopa.

Stars	This entity has been manually annotated by the ChEBI Team.

Supplier Information	eMolecules:5747897, ZINC000012495043

Download	Molfile XML SDF

more structures >>

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3YM - Ideal conformer

RDKit 3D

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Time for openFile(3YM - Ideal conformer

RDKit 3D

28 28 0 0 0 0 0 0 0 0999 V2000

-2.5970 2.7950 -0.1690 C 0 0 0 0 0 0 0 0 0 0 0 0

-3.1400 1.4740 -0.2270 O 0 0 0 0 0 0 0 0 0 0 0 0

-2.2870 0.4450 0.0200 C 0 0 0 0 0 0 0 0 0 0 0 0

-0.9560 0.7000 0.3120 C 0 0 0 0 0 0 0 0 0 0 0 0

-2.7490 -0.8670 -0.0140 C 0 0 0 0 0 0 0 0 0 0 0 0

-4.0530 -1.1230 -0.3010 O 0 0 0 0 0 0 0 0 0 0 0 0

-1.8770 -1.9130 0.2440 C 0 0 0 0 0 0 0 0 0 0 0 0

-0.5510 -1.6510 0.5350 C 0 0 0 0 0 0 0 0 0 0 0 0

-0.0900 -0.3480 0.5630 C 0 0 0 0 0 0 0 0 0 0 0 0

1.3560 -0.0680 0.8810 C 0 0 0 0 0 0 0 0 0 0 0 0

2.1700 -0.0580 -0.4150 C 0 0 1 0 0 0 0 0 0 0 0 0

3.5910 0.3420 -0.1130 C 0 0 0 0 0 0 0 0 0 0 0 0

4.4490 -0.5030 -0.0210 O 0 0 0 0 0 0 0 0 0 0 0 0

2.1550 -1.3990 -1.0140 N 0 0 0 0 0 0 0 0 0 0 0 0

-2.1960 2.9800 0.8280 H 0 0 0 0 0 0 0 0 0 0 0 0

-1.7990 2.8930 -0.9050 H 0 0 0 0 0 0 0 0 0 0 0 0

-3.3810 3.5200 -0.3850 H 0 0 0 0 0 0 0 0 0 0 0 0

-0.5960 1.7180 0.3440 H 0 0 0 0 0 0 0 0 0 0 0 0

-4.2320 -1.2440 -1.2430 H 0 0 0 0 0 0 0 0 0 0 0 0

-2.2340 -2.9320 0.2230 H 0 0 0 0 0 0 0 0 0 0 0 0

0.1280 -2.4670 0.7360 H 0 0 0 0 0 0 0 0 0 0 0 0

1.4400 0.9020 1.3700 H 0 0 0 0 0 0 0 0 0 0 0 0

1.7390 -0.8440 1.5440 H 0 0 0 0 0 0 0 0 0 0 0 0

1.7320 0.6560 -1.1130 H 0 0 0 0 0 0 0 0 0 0 0 0

2.5560 -2.0790 -0.3860 H 0 0 0 0 0 0 0 0 0 0 0 0

1.2200 -1.6640 -1.2850 H 0 0 0 0 0 0 0 0 0 0 0 0

3.9020 1.6370 0.0540 O 0 0 0 0 0 0 0 0 0 0 0 0

4.8270 1.8450 0.2460 H 0 0 0 0 0 0 0 0 0 0 0 0

7 8 2 0

7 5 1 0

8 9 1 0

13 12 2 0

11 12 1 0

11 14 1 0

11 10 1 0

6 5 1 0

5 3 2 0

9 10 1 0

9 4 2 0

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1 15 1 0

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4 18 1 0

6 19 1 0

7 20 1 0

8 21 1 0

10 22 1 0

10 23 1 0

11 24 1 6

14 25 1 0

14 26 1 0

12 27 1 0

27 28 1 0

M END): 30 ms

reading 28 atoms

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28 atoms created

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Wikipedia	License
3-O-Methyldopa (3-OMD) is one of the most important metabolites of L-DOPA, a drug used in the treatment of the Parkinson's disease. 3-O-methyldopa is produced by the methylation of L-DOPA by the enzyme catechol-O-methyltransferase. The necessary cofactor for this enzymatic reaction is s-adenosyl methionine (SAM). Its half-life (approximately 15 hours) is longer than L-DOPA's half-life, which is about one hour. This means that it is accumulated in the plasma and the brain of chronic L-DOPA therapy patients such as people suffering from Parkinson's disease. 3-OMD is often elevated in the plasma and cerebrospinal fluid of Parkinson's disease patients taking L-DOPA. It's serum levels are also elevated in patients with AADC deficit, making it a useful marker for screening of this disease.
Read full article at Wikipedia

Formula

C10H13NO4

Net Charge

Average Mass

211.217

Monoisotopic Mass

211.08446

InChI

InChI=1S/C10H13NO4/c1-15-9-5-6(2-3-8(9)12)4-7(11)10(13)14/h2-3,5,7,12H,4,11H2,1H3,(H,13,14)/t7-/m0/s1

InChIKey

PFDUUKDQEHURQC-ZETCQYMHSA-N

SMILES

O=C(O)[C@@H](N)CC=1C=C(C(=CC1)O)OC

Metabolite of Species	Details
Homo sapiens (NCBI:txid9606)	See: PubMed

Roles Classification
Chemical Role(s):	Bronsted base A molecular entity capable of accepting a hydron from a donor (Bronsted acid). (via organic amino compound ) Bronsted acid A molecular entity capable of donating a hydron to an acceptor (Bronsted base). (via oxoacid )

Biological Role(s):	human metabolite Any mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens).

View more via ChEBI Ontology

ChEBI Ontology
Outgoing	3-O-methyldopa (CHEBI:82913) has functional parent L-dopa (CHEBI:15765) 3-O-methyldopa (CHEBI:82913) has role human metabolite (CHEBI:77746) 3-O-methyldopa (CHEBI:82913) is a L-tyrosine derivative (CHEBI:27177) 3-O-methyldopa (CHEBI:82913) is a monomethoxybenzene (CHEBI:25235) 3-O-methyldopa (CHEBI:82913) is a non-proteinogenic L-α-amino acid (CHEBI:83822) 3-O-methyldopa (CHEBI:82913) is tautomer of 3-O-methyldopa zwitterion (CHEBI:133668)

Incoming	3-O-methyldopa zwitterion (CHEBI:133668) is tautomer of 3-O-methyldopa (CHEBI:82913)

IUPAC Name

3-methoxy-L-tyrosine

Synonym	Source
L-3-(4-hydroxy-3-methoxyphenyl)-alanine	ChEBI

Manual Xrefs	Databases
3-O-Methyldopa	Wikipedia
3YM	PDBeChem
HMDB0001434	HMDB
View more database links

Registry Numbers	Types	Sources
2379987	Reaxys Registry Number	Reaxys
300-48-1	CAS Registry Number	ChemIDplus

Citations	Types	Sources
23503547	PubMed citation	Europe PMC
24513538	PubMed citation	Europe PMC

Last Modified

25 November 2019

CHEBI:82913 - 3-O-methyldopa

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