Glycocyamine
Names
IUPAC name
N -Carbamimidoylglycine
Systematic IUPAC name
2-(Diaminomethylideneamino)acetic acid
Other names
2-Guanidinoacetic acid[citation needed ]
Identifiers
CAS Number
352-97-6 Y
3D model (JSmol)
3DMet
Beilstein Reference
1759179
ChEBI
CHEBI:16344 N
ChEMBL
ChEMBL281593 N
ChemSpider
743 N
DrugBank
DB02751 N
ECHA InfoCard
100.005.936
EC Number
KEGG
C00581 N
MeSH
glycocyamine
UNII
GO52O1A04E Y
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
Properties
Chemical formula
C 3 H 7 N 3 O 2
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 (pK a )
3.414
Basicity (pK b )
10.583
Hazards
GHS labelling:
Pictograms
Signal word
Warning
Hazard statements
H315 , H319 , H335
Precautionary statements
P261 , P305+P351+P338
Related compounds
Related alkanoic acids
Sarcosine Dimethylglycine Creatine N -Methyl-D -aspartic acidbeta -Methylamino-L -alanineGuanidinopropionic acid
Related compounds
Dimethylacetamide
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references
Chemical compound
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.
Last Update: 2024-03-26T12:52:02Z
Glycocyamine (or guanidinoacetate) is a metabolite of glycine in which the amino group has been converted into a guanidine by guanylation (transfer of...
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Last Update: 2023-02-28T17:19:45Z
amino acids — arginine and glycine — into guanidinoacetate (also called glycocyamine or GAA), which is then transported in the blood to the liver. A methyl...
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Last Update: 2024-04-30T20:20:43Z
Creatine is synthesized primarily in the liver from the methylation of glycocyamine (guanidino acetate, synthesized in the kidney from the amino acids arginine...
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glycine→ serine→ 3-Phosphoglyceric acid glycine→creatine: Glycocyamine Phosphocreatine Creatinine...
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glycine→ serine→ 3-Phosphoglyceric acid glycine→creatine: Glycocyamine Phosphocreatine Creatinine...
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glycine→ serine→ 3-Phosphoglyceric acid glycine→creatine: Glycocyamine Phosphocreatine Creatinine...
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glycine→ serine→ 3-Phosphoglyceric acid glycine→creatine: Glycocyamine Phosphocreatine Creatinine...
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glycine→ serine→ 3-Phosphoglyceric acid glycine→creatine: Glycocyamine Phosphocreatine Creatinine...
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P305+P351+P338 Related compounds Related alkanoic acids Sarcosine Dimethylglycine Glycocyamine N-Methyl-D-aspartic acid beta-Methylamino-L-alanine Guanidinopropionic...
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glycine→ serine→ 3-Phosphoglyceric acid glycine→creatine: Glycocyamine Phosphocreatine Creatinine...
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glycine→ serine→ 3-Phosphoglyceric acid glycine→creatine: Glycocyamine Phosphocreatine Creatinine...
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glycine→ serine→ 3-Phosphoglyceric acid glycine→creatine: Glycocyamine Phosphocreatine Creatinine...
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glycine→ serine→ 3-Phosphoglyceric acid glycine→creatine: Glycocyamine Phosphocreatine Creatinine...
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glycine→ serine→ 3-Phosphoglyceric acid glycine→creatine: Glycocyamine Phosphocreatine Creatinine...
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glycine→ serine→ 3-Phosphoglyceric acid glycine→creatine: Glycocyamine Phosphocreatine Creatinine...
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glycine→ serine→ 3-Phosphoglyceric acid glycine→creatine: Glycocyamine Phosphocreatine Creatinine...
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glycine→ serine→ 3-Phosphoglyceric acid glycine→creatine: Glycocyamine Phosphocreatine Creatinine...
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glycine→ serine→ 3-Phosphoglyceric acid glycine→creatine: Glycocyamine Phosphocreatine Creatinine...
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glycine→ serine→ 3-Phosphoglyceric acid glycine→creatine: Glycocyamine Phosphocreatine Creatinine...
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glycine→ serine→ 3-Phosphoglyceric acid glycine→creatine: Glycocyamine Phosphocreatine Creatinine...
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glycine→ serine→ 3-Phosphoglyceric acid glycine→creatine: Glycocyamine Phosphocreatine Creatinine...
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glycine→ serine→ 3-Phosphoglyceric acid glycine→creatine: Glycocyamine Phosphocreatine Creatinine...
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