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MetaCyc Compound: (R)-noradrenaline

Synonyms: (R)-norepinephrine, (-)-noradrenaline, (-)-norepinephrine, (-)-arterenol, (R)-(-)-norepinephrine, (R)-4-(2-amino-1-hydroxyethyl)-1,2-benzenediol, (2R)-2-(3,4-dihydroxyphenyl)-2-hydroxyethanaminium

Superclasses: an alcohol a diol a benzenediol a catechol
an aromatic compound a benzenediol a catechol

Chemical Formula: C8H12NO3

Molecular Weight: 170.19 Daltons

Monoisotopic Molecular Weight: 169.0738932246 Daltons

(R)-noradrenaline compound structure

SMILES: C1(C=C(O)C(=CC=1C(C[N+])O)O)

InChI: InChI=1S/C8H11NO3/c9-4-8(12)5-1-2-6(10)7(11)3-5/h1-3,8,10-12H,4,9H2/p+1/t8-/m0/s1

InChIKey: InChIKey=SFLSHLFXELFNJZ-QMMMGPOBSA-O

Unification Links: ChEBI:72587 , ChemSpider:3037559 , DrugBank:DB00368 , HMDB:HMDB00216 , KEGG:C00547 , PubChem:6921840

Standard Gibbs Free Energy of Change Formation (ΔfG in kcal/mol): 34.531376 Inferred by computational analysis [Latendresse13]

Reactions known to consume the compound:

catecholamine biosynthesis :
S-adenosyl-L-methionine + (R)-noradrenalineS-adenosyl-L-homocysteine + (R)-adrenaline + H+

noradrenaline and adrenaline degradation :
(R)-noradrenaline + H2O + oxygen → 3,4-dihydroxyphenylglycolaldehyde + ammonium + hydrogen peroxide
(R)-noradrenaline + S-adenosyl-L-methionine → normetanephrine + S-adenosyl-L-homocysteine + H+
S-adenosyl-L-methionine + (R)-noradrenalineS-adenosyl-L-homocysteine + (R)-adrenaline + H+

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

Not in pathways:
4 a benzenediol + oxygen → 4 a benzosemiquinone + 2 H2O

Reactions known to produce the compound:

catecholamine biosynthesis :
dopamine + L-ascorbate + H+ + oxygen → L-dehydro-ascorbate + (R)-noradrenaline + H2O

β-D-glucuronide and D-glucuronate degradation :
a β-D-glucuronoside + H2O → D-glucopyranuronate + an alcohol

glycerophosphodiester degradation :
a glycerophosphodiester + H2O → an alcohol + sn-glycerol 3-phosphate + H+

phosphate acquisition , phosphate utilization in cell wall regeneration :
a phosphate monoester + H2O → an alcohol + phosphate

Not in pathways:
an organic hydroperoxide + NADH + H+an alcohol + NAD+ + H2O
an α-D-glucuronoside + H2O → D-glucopyranuronate + an alcohol
an α amino acid ester + H2O → an alcohol + an α amino acid + H+
a phosphate monoester + H2O → an alcohol + phosphate
RH + a reduced [NADPH-hemoprotein reductase] + oxygen → ROH + an oxidized [NADPH-hemoprotein reductase] + H2O
an oligosaccharide with β-L-arabinopyranose at the non-reducing end + H2O → β-L-arabinopyranose + an alcohol
an N-acetyl-β-D-hexosaminide + H2O → an N-acetyl-β-D-hexosamine + an alcohol
a carboxylic ester + H2O → an alcohol + a carboxylate + H+
an acetic ester + H2O → an alcohol + acetate + H+
a reduced thioredoxin + an organic hydroperoxide → an oxidized thioredoxin + an alcohol + H2O
a 6-O-(β-D-xylopyranosyl)-β-D-glucopyranoside + H2O → β-primeverose + an alcohol
an organic molecule + H2O + 2 oxygen → an alcohol + 2 superoxide + 2 H+
an N5-acyl-L-ornithine-ester + H2O → an N5-acyl-L-ornithine + an alcohol
α-L-fucoside + H2O → L-fucopyranose + an alcohol
a 2-deoxy-α-D-glucoside + H2O → 2-deoxy-D-glucose + an alcohol
a 6-phospho-β-D-galactoside + H2O → α-D-galactose 6-phosphate + an alcohol

In Reactions of unknown directionality:

Not in pathways:
an alcohol + 3'-phosphoadenylyl-sulfate = adenosine 3',5'-bisphosphate + an organosulfate + H+
an alcohol + NAD(P)+ = an aldehyde + NAD(P)H + H+
an alcohol + NADP+ = an aldehyde + NADPH + H+
trans-cinnamoyl-β-D-glucoside + an alcohol = β-D-glucopyranose + alkyl cinnamate
an alcohol + acetyl-CoA = an acetic ester + coenzyme A
2 protein cysteines + an organic hydroperoxide = a protein disulfide + an alcohol + H2O
an organic molecule + an organic hydroperoxide = 2 an alcohol
an organic molecule + hydrogen peroxide = an alcohol + H2O

Enzymes inhibited by (R)-noradrenaline, sorted by the type of inhibition, are:

Inhibitor (Mechanism unknown) of: γ-glutamylhistamine synthetase [Stein82]

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

Credits:
Revised 11-Dec-2012 by Caspi R , SRI International


References

Latendresse13: Latendresse M. (2013). "Computing Gibbs Free Energy of Compounds and Reactions in MetaCyc."

Stein82: Stein C, Weinreich D (1982). "An in vitro characterization of gamma-glutamylhistamine synthetase: a novel enzyme catalyzing histamine metabolism in the central nervous system of the marine mollusk, Aplysia californica." J Neurochem 38(1);204-14. PMID: 6125565


Report Errors or Provide Feedback
Please cite the following article in publications resulting from the use of MetaCyc: Caspi et al, Nucleic Acids Research 42:D459-D471 2014
Page generated by SRI International Pathway Tools version 19.0 on Sat Aug 29, 2015, biocyc13.