Compound

5-amino-1-(5-phospho-beta-D-ribosyl)imidazole

An organophosphate oxoanion obtained by deprotonation of the phosphate OH groups as well as protonation of the endocyclic nitrogen at position 3 in the imidazole ring of 5-amino-1-(5-phospho-β-D-ribosyl)imidazole. It is the major microspecies at pH 7.3 (according to Marvin v 6.2.0.).

Definition from ChEBI (CHEBI:137981), read 2026-09-23. CC BY 4.0.

CHEBI:137981ChEBI

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Structure

2D depiction · 3D model shown

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A generated conformer of 5-amino-1-(5-phospho-beta-D-ribosyl)imidazole — one low-energy arrangement PubChem computed, not a measured structure. Hydrogens are not drawn; the formula counts them.

Class: Organic compound, anion
Formula: C8H13N3O7P
Mass: 294.18 g/mol
Charge: -1
InChIKey: PDACUKOKVHBVHJ-XVFCMESISA-M
SMILES: Nc1c[nH+]cn1[C@@H]1O[C@H](COP(=O)([O-])[O-])[C@@H](O)[C@H]1O
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

6 statements

6 statements · 1 reference database · Subject: 5-amino-1-(5-phospho-beta-D-ribosyl)imidazole · Sources: Rhea

Order

5-amino-1-(5-phospho-beta-D-ribosyl)imidazole is converted to 2-formamido-N(1)-(5-O-phospho-beta-D-ribosyl)acetamidineCompoundRhea RHEA:23032Inferred only
2-formamido-N(1)-(5-O-phospho-beta-D-ribosyl)acetamidine is converted to 5-amino-1-(5-phospho-beta-D-ribosyl)imidazoleCompoundRhea RHEA:23032Inferred only
5-amino-1-(5-phospho-beta-D-ribosyl)imidazole is converted to 5-amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxylateCompoundRhea RHEA:10792Inferred only
5-amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxylate is converted to 5-amino-1-(5-phospho-beta-D-ribosyl)imidazoleCompoundRhea RHEA:10792Inferred only
5-amino-1-(5-phospho-beta-D-ribosyl)imidazole is a substrate of GARTProteinRhea RHEA:23032Inferred only
5-amino-1-(5-phospho-beta-D-ribosyl)imidazole is a substrate of PAICSProteinRhea RHEA:10792Inferred only

Reactions

6 reactions

5-amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxylate+hydron5-amino-1-(5-phospho-beta-D-ribosyl)imidazole+carbon dioxide
Catalysed by PAICS
Reaction pageRight to leftBalance undeterminable
Rhea RHEA:10792CC BY 4.0Reference data
5-amino-1-(5-phospho-beta-D-ribosyl)imidazole+hydrogencarbonate+ATP(4-)CHEBI:58730+ADP(3-)+hydrogenphosphate+2hydron
Reaction pageDirection not assertedBalance undeterminable
Rhea RHEA:19317CC BY 4.0Reference data
2-formamido-N(1)-(5-O-phospho-beta-D-ribosyl)acetamidine+ATP(4-)5-amino-1-(5-phospho-beta-D-ribosyl)imidazole+ADP(3-)+hydrogenphosphate+hydron
Catalysed by GART
Reaction pageLeft to rightBalance undeterminable
Rhea RHEA:23032CC BY 4.0Reference data
5-amino-1-(5-phospho-beta-D-ribosyl)imidazole+S-adenosyl-L-methionineCHEBI:58354+CO+5'-deoxyadenosine+formate+L-methionine+3hydron
Reaction pageDirection not assertedBalance undeterminable
Rhea RHEA:24840CC BY 4.0Reference data
CHEBI:142407+ATP(4-)5-amino-1-(5-phospho-beta-D-ribosyl)imidazole+ADP(3-)+hydron
Reaction pageDirection not assertedBalance undeterminable
Rhea RHEA:44748CC BY 4.0Reference data
5-amino-1-(5-phospho-beta-D-ribosyl)imidazole+AH2+S-adenosyl-L-methionineCHEBI:137404+5'-deoxyadenosine+formate+L-methionine+A+ammonium+hydrogenphosphate+2hydron
Reaction pageDirection not assertedBalance undeterminable
Rhea RHEA:53504CC BY 4.0Reference data

Other names

2 names

Resolves to: 5-amino-1-(5-phospho-beta-D-ribosyl)imidazole

Systematic name: 5-amino-1-(5-O-phosphonato-beta-D-ribofuranosyl)-1H-imidazol-3-ium5-amino-1-(5-O-phosphonato-β-D-ribofuranosyl)-1H-imidazol-3-ium