glycocyamine

Also known as Betacyamine, Guanidoacetic acid, Amidinoglycine, N-(aminoiminomethyl)glycine, Guanyl glycine, N-amidinoglycine, Guanidineacetic acid

Glycocyamine (or guanidinoacetate) is a metabolite of glycine in which the amino group has been converted into a guanidine by guanylation (transfer of a guanidine group from arginine). In vertebrate organism it is then transformed into creatine by methylation.

Chemical data

Formula: C3H7N3O2
Molecular weight: 117.11 g/mol
IUPAC name: 2-(diaminomethylideneamino)acetic acid
SMILES: C(C(=O)O)N=C(N)N
InChIKey: BPMFZUMJYQTVII-UHFFFAOYSA-N
XLogP: -1.6
Polar surface area: 102 Å²
H-bond donors: 3
H-bond acceptors: 3
Formal charge: 0

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Drug data · ChEMBL

Molecule type: Small molecule

via ChEMBL · EBI

Research

484 papers

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Wikidata facts

Subclass of: ion
Mass: 117.054

Show 6 more facts

chemical formula: C₃H₇N₃O₂
canonical SMILES: C(C(=O)O)N=C(N)N
found in taxon: Malus domestica
subject has role: primary metabolite
isomeric SMILES: O=C(O)CNC(=N)N
Commons category: Glycocyamine

Sources (3)

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Encyclopedic overview

9 sections

Contents

Production
Biochemical synthesis
Chemical synthesis
Properties
Uses
As a supplement
As a feed additive
References
See also

Glycocyamine is used as a supplement and as a feed additive in poultry farming. However, the metabolism of creatine from glycocyamine in the liver causes a depletion of methyl groups. This causes homocysteine levels to rise, which has been shown to produce cardiovascular and skeletal problems. Glycocyamine plays a role in the metabolism of the amino acids serine, threonine, and proline.

Excerpted from Wikipedia’s “glycocyamine” article, available under the CC BY-SA 4.0 licence.