Glycocyamine

Glycocyamine
Skeletal formula of a glycocyamine minor tautomer
Ball and stick model of a glycocyamine minor tautomer
Spacefill model of a glycocyamine minor tautomer
Names
IUPAC name
N-Carbamimidoylglycine
Systematic IUPAC name
2-(Diaminomethylideneamino)acetic acid
Other names
2-Guanidinoacetic acid[citation needed]
Identifiers
3D model (JSmol)
3DMet
1759179
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.005.936 Edit this at Wikidata
EC Number
  • 206-529-5
KEGG
MeSH glycocyamine
UNII
  • InChI=1S/C3H7N3O2/c4-3(5)6-1-2(7)8/h1H2,(H,7,8)(H4,4,5,6) ☒N
    Key: BPMFZUMJYQTVII-UHFFFAOYSA-N ☒N
  • NC(=N)NCC(O)=O
Properties
C3H7N3O2
Molar mass 117.108 g·mol−1
Appearance White crystals
Odor Odourless
Melting point 300 °C (572 °F; 573 K)
log P −1.11
Acidity (pKa) 3.414
Basicity (pKb) 10.583
Hazards
GHS labelling:
GHS07: Exclamation mark
Warning
H315, H319, H335
P261, P305+P351+P338
Related compounds
Related alkanoic acids
Related compounds
 Dimethylacetamide
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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.

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.[citation needed] Glycocyamine plays a role in the metabolism of the amino acids serine, threonine, and proline.