Compound

N(omega)-hydroxy-L-arginine

Conjugate acid of N5-[(hydroxyamino)(imino)methyl]-L-ornithine having an anionic carboxy group and protonated amiino and guanidino groups. It is the principal microspecies present at pH 7.3.

Definition from ChEBI (CHEBI:60107), read 2026-09-23. CC BY 4.0.

CHEBI:60107ChEBI

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Structure

2D depiction · 3D model shown

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

Class: Organic compound, cation
Formula: C6H15N4O3
Mass: 191.211 g/mol
Charge: +1
InChIKey: FQWRAVYMZULPNK-BYPYZUCNSA-O
SMILES: [NH2+]=C(NO)NCCC[C@H]([NH3+])C(=O)[O-]
Look it up: ChEBI PubChem By InChIKey

Identity from ChEBI, geometry from PubChem. Not evidence.

What it touches on the way

Mechanistic reach

2 entities

2 entities reached.

0 reported hops2 assembled from the scaffold

What the reference databases state

Statements

2 statements

2 statements · 1 reference database · Subject: N(omega)-hydroxy-L-arginine · Sources: Rhea

Order

N(omega)-hydroxy-L-arginine is a substrate of MTARC1ProteinRhea RHEA:61644Inferred only
N(omega)-hydroxy-L-arginine is a substrate of MTARC2ProteinRhea RHEA:61644Inferred only

Reactions

9 reactions

L-arginine+NADPH(4-)+dioxygen+hydronN(omega)-hydroxy-L-arginine+NADP(3-)+water
Reaction pageDirection not assertedBalance undeterminable
Rhea RHEA:24660CC BY 4.0Reference data
2N(omega)-hydroxy-L-arginine+NADPH(4-)+2dioxygen2L-citrulline+2nitric oxide+NADP(3-)+2water+hydron
Reaction pageDirection not assertedBalance undeterminable
Rhea RHEA:24664CC BY 4.0Reference data
2N(omega)-hydroxy-L-arginine+NADH(2-)+2dioxygen2L-citrulline+2nitric oxide+NAD(1-)+2water+hydron
Reaction pageDirection not assertedBalance undeterminable
Rhea RHEA:33935CC BY 4.0Reference data
L-arginine+NADH(2-)+dioxygen+hydronN(omega)-hydroxy-L-arginine+NAD(1-)+water
Reaction pageDirection not assertedBalance undeterminable
Rhea RHEA:33939CC BY 4.0Reference data
N(omega)-hydroxy-L-arginine+waterCHEBI:44423+L-ornithine
Reaction pageDirection not assertedBalance undeterminable
Rhea RHEA:36791CC BY 4.0Reference data
reduced [flavodoxin]+L-arginine+dioxygenN(omega)-hydroxy-L-arginine+oxidized [flavodoxin]+water+hydron
Reaction pageDirection not assertedBalance undeterminable
Rhea RHEA:52328CC BY 4.0Reference data
2N(omega)-hydroxy-L-arginine+reduced [flavodoxin]+2dioxygenoxidized [flavodoxin]+2L-citrulline+2nitric oxide+2water+3hydron
Reaction pageDirection not assertedBalance undeterminable
Rhea RHEA:52332CC BY 4.0Reference data
N(omega)-hydroxy-L-arginine+2Fe(II)-[cytochrome b5]+2hydronL-arginine+2Fe(III)-[cytochrome b5]+water
Catalysed by MTARC1 or MTARC2
Reaction pageLeft to rightBalance undeterminable
Rhea RHEA:61644CC BY 4.0Reference data
L-cysteinyl-[NO transferase protein]+N(omega)-hydroxy-L-arginine+dioxygenS-nitroso-L-cysteinyl-[NO transferase protein]+L-citrulline+water+hydron
Reaction pageDirection not assertedBalance undeterminable
Rhea RHEA:67140CC BY 4.0Reference data

Other names

5 names

Resolves to: N(omega)-hydroxy-L-arginine

Also called: (2S)-2-ammonio-5-{[(hydroxyamino)(iminio)methyl]amino}pentanoateL-hydroxyarginineN(5)-[(hydroxyamino)(imino)methyl]-L-ornithinium cationN5-[(hydroxyamino)(imino)methyl]-L-ornithinium cation
Systematic name: (2S)-2-azaniumyl-5-{[(hydroxyamino)(iminio)methyl]amino}pentanoate