Compound

(R)-normetanephrine

Conjugate acid of L-normetanephrine; major microspecies at pH 7.3.

Definition from ChEBI (CHEBI:189645), read 2026-09-23. CC BY 4.0.

CHEBI:189645ChEBI

Open in the graph

Structure

2D depiction · 3D model shown

Loading the model…

A generated conformer of (R)-normetanephrine — one low-energy arrangement PubChem computed, not a measured structure. Hydrogens are not drawn; the formula counts them.

Class: Organic compound, cation
Formula: C9H14NO3
Mass: 184.215 g/mol
Charge: +1
InChIKey: YNYAYWLBAHXHLL-QMMMGPOBSA-O
SMILES: COc1cc([C@@H](O)C[NH3+])ccc1O
Look it up: ChEBI PubChem By InChIKey

Identity from ChEBI, geometry from PubChem. Not evidence.

What it touches on the way

Mechanistic reach

3 entities

3 entities reached.

0 reported hops3 assembled from the scaffold

What the reference databases state

Statements

4 statements

4 statements · 2 reference databases · Subject: (R)-normetanephrine · Sources: Human-GEM, Rhea

Order

(R)-noradrenaline is converted to (R)-normetanephrineCompoundHuman-GEM MAR06750Inferred only
(R)-normetanephrine is metabolised by MAOAProteinHuman-GEM MAR06751Inferred only
(R)-normetanephrine is metabolised by MAOBProteinHuman-GEM MAR06751Inferred only
(R)-normetanephrine is a substrate of PNMTProteinRhea RHEA:70683Inferred only

Reactions

7 reactions

(R)-noradrenaline+S-adenosyl-L-methionineproton+(R)-normetanephrine+CHEBI:16680
Catalysed by COMT or LRTOMT
Reaction pageLeft to rightBalancedEC 2.1.1.6GO:0005829
Human-GEM MAR06750CC BY 4.0Reference data
water+(R)-normetanephrine+dioxygenMAM00820c+proton+hydrogen peroxide+ammonium
Catalysed by MAOB or MAOA
Reaction pageLeft to rightBalancedEC 1.4.3.4GO:0005829
Human-GEM MAR06751CC BY 4.0Reference data
(R)-normetanephrine(R)-normetanephrine
Reaction pageReversibleBalancedGO:0005615, GO:0005829
Human-GEM MAR10479CC BY 4.0Reference data
(R)-normetanephrine
Reaction pageReversibleBalance undeterminableGO:0005615
Human-GEM MAR10490CC BY 4.0Reference data
2ATP+2water+3(R)-normetanephrine2ADP+2proton+3(R)-normetanephrine+2phosphate(3-)
Reaction pageLeft to rightBalancedGO:0005829, GO:0005615
Human-GEM MAR11314CC BY 4.0Reference data
(R)-normetanephrine+S-adenosyl-L-methionine(R)-metanephrine+S-adenosyl-L-homocysteine+hydron
Catalysed by PNMT
Reaction pageLeft to rightBalance undeterminable
Rhea RHEA:70683CC BY 4.0Reference data
(R)-noradrenaline+S-adenosyl-L-methionine(R)-normetanephrine+S-adenosyl-L-homocysteine+hydron
Reaction pageDirection not assertedBalance undeterminable
Rhea RHEA:72247CC BY 4.0Reference data

Other names

1 name

Resolves to: (R)-normetanephrine

Also called: (2R)-2-hydroxy-2-(4-hydroxy-3-methoxyphenyl)ethanaminium