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Homo sapiens Compound: L-dopa

Synonyms: DOPA, 3-hydroxytyrosine, 3,4-dihydroxy-L-phenylalanine, dihydroxyphenylalanine, L-dihydroxy-phenylalanine, levodopa

Superclasses: an acidall carboxy acidsa carboxylatean amino acidan alpha amino acida non-standard alpha amino acid
an alcohola diola benzenediola catechol
an amino acid or its derivativean amino acidan alpha amino acida non-standard alpha amino acid
an aromatic compounda benzenediola catechol


Chemical Formula: C9H11NO4

Molecular Weight: 197.19 Daltons

Monoisotopic Molecular Weight: 198.07663287879998 Daltons

L-dopa compound structure

SMILES: C(C(CC1(C=CC(O)=C(O)C=1))[N+])(=O)[O-]

InChI: 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

InChIKey: InChIKey=WTDRDQBEARUVNC-LURJTMIESA-N

Unification Links: CAS:59-92-7, ChEBI:57504, HMDB:HMDB00181, KEGG:C00355, MetaboLights:MTBLC57504, NCI:118381, PubChem:6971033

Reactions known to consume the compound:

catecholamine biosynthesis :
L-dopa + H+ → dopamine + CO2

L-dopa degradation :
L-dopa + S-adenosyl-L-methionine → 3-O-methyldopa + S-adenosyl-L-homocysteine + H+

Not in pathways:
L-dopa + 0.5 oxygen → dopaquinone + H2O

Not in pathways:
a catechol + S-adenosyl-L-methionine → a guaiacol + S-adenosyl-L-homocysteine + H+

Not in pathways:
a carboxylate + ATP + coenzyme A → an acyl-CoA + AMP + diphosphate

Reactions known to produce the compound:

(S)-reticuline biosynthesis :
L-tyrosine + 0.5 oxygen → L-dopa

catecholamine biosynthesis :
tetrahydrobiopterin + L-tyrosine + oxygen → 4α-hydroxy-tetrahydrobiopterin + L-dopa

L-dopachrome biosynthesis :
leucodopachrome + dopaquinone → L-dopachrome + L-dopa

Not in pathways:
a protein + H2O → a protein + an α amino acid

Not in pathways:
an L-1-phosphatidyl-inositol + H2O → a 1-acyl-sn-glycero-3-phospho-D-myo-inositol + a carboxylate + H+
an acyl-CoA + H2O → a carboxylate + coenzyme A + H+
an aldehyde + oxygen + H2O → a carboxylate + hydrogen peroxide + H+
a carboxylic ester + H2O → an alcohol + a carboxylate + H+
an acylcholine + H2O → choline + a carboxylate + H+
a 2-acyl 1-lyso-phosphatidylcholine + H2O → a carboxylate + sn-glycero-3-phosphocholine + H+
an N-acyl-L-aspartate + H2O → L-aspartate + a carboxylate

Not in pathways:
RH + a reduced [NADPH-hemoprotein reductase] + oxygen → ROH + an oxidized [NADPH-hemoprotein reductase] + H2O
α-L-fucoside + H2O → L-fucopyranose + an alcohol
a β-D-glucuronoside + H2O → D-glucopyranuronate + an alcohol
an N-acetyl-β-D-hexosaminide + H2O → an N-acetyl-β-D-hexosamine + an alcohol
a phosphate monoester + H2O → an alcohol + phosphate
an organic molecule + H2O + 2 oxygen → an alcohol + 2 superoxide + 2 H+
a carboxylic ester + H2O → an alcohol + a carboxylate + H+
a glycerophosphodiester + H2O → an alcohol + sn-glycerol 3-phosphate + H+
a phosphate monoester + H2O → an alcohol + phosphate

Reactions known to both consume and produce the compound:

(S)-reticuline biosynthesis :
L-dopa + 2-oxoglutarate ↔ 3,4-dihydroxyphenylpyruvate + L-glutamate

In Reactions of unknown directionality:

Not in pathways:
a 5-L-glutamyl-[peptide] + an amino acid = a 5-L-glutamyl-amino acid + a peptide

Not in pathways:
an aldehyde + NAD+ + H2O = a carboxylate + NADH + 2 H+
an aldehyde + NAD(P)+ + H2O = a carboxylate + NAD(P)H + 2 H+
an aldehyde + FAD + H2O = a carboxylate + FADH2
a nitrile + 2 H2O = a carboxylate + ammonium
an aldehyde + NADP+ + H2O = a carboxylate + NADPH + 2 H+
an N-acylated aliphatic-L-amino acid + H2O = a carboxylate + an aliphatic L-amino acid
a triacyl-sn-glycerol + H2O = a carboxylate + a 1,2-diacyl-sn-glycerol + H+
an acyl phosphate + H2O = a carboxylate + phosphate + H+

Not in pathways:
an alcohol + NADP+ = an aldehyde + NADPH + H+
an alcohol + 3'-phosphoadenylyl-sulfate = adenosine 3',5'-bisphosphate + an organosulfate + H+
an alcohol + NAD(P)+ = an aldehyde + NAD(P)H + H+
a reduced thioredoxin + an organic hydroperoxide = an oxidized thioredoxin + an alcohol + H2O
2 protein cysteines + an organic hydroperoxide = a protein disulfide + an alcohol + H2O

This compound has been characterized as an alternative substrate of the following enzymes: L-tryptophan decarboxylase, catechol O-methyltransferase


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Please cite the following article in publications resulting from the use of HumanCyc: Genome Biology 6(1):1-17 2004
Page generated by Pathway Tools version 19.5 (software by SRI International) on Tue Feb 9, 2016, biocyc11.