2-carbamimidamidoacetic acid

• ChemBase ID: 2469
• Molecular Formular: C3H7N3O2
• Molecular Mass: 117.10658
• Monoisotopic Mass: 117.05382648
• SMILES: NC(=N)NCC(=O)O
• Canonical SMILES: NC(=N)NCC(=O)O
• InChI: InChI=1S/C3H7N3O2/c4-3(5)6-1-2(7)8/h1H2,(H,7,8)(H4,4,5,6)
• InChIKey: BPMFZUMJYQTVII-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-carbamimidamidoacetic acid
• IUPAC Traditional name: N-[amino(imino)methyl]glycine; glycocyamine
• Synonyms: GLYCOCYAMINE; Glycocyamine; N-Amidinoglycine; N-Guanylglycine; GUANIDOACETIC ACID; N-[Amino(Imino)Methyl]Glycine; 2-{[amino(imino)methyl]amino}acetic acid; Guanidineacetic acid; 2-Guanidinoacetic acid; N-(Aminoiminomethyl)-glycine; 2-[[Amino(imino)methyl]amino]acetic Acid; NSC 26360; NSC 227847; NSC 1901; Betacyamine; Guanidinoacetic Acid; N-脒基甘氨酸; 甘氨酸氰胺; 胍基乙酸; 乙酸胍; 胍乙酸

Database IDs

• CAS Number: 352-97-6
• EC Number: 206-529-5
• MDL Number: MFCD00004278
• Beilstein Number: 1759179
• Merck Index: 144495
• PubChem SID: 46506215; 24895047; 160965919
• PubChem CID: 763
• CHEBI ID: 16344
• CHEMBL: 281593
• Chemspider ID: 743
• DrugBank ID: DB02751
• KEGG ID: C00581
• MeSH Name: glycocyamine
• Unique Ingredient Identifier: GO52O1A04E
• Wikipedia Title: Glycocyamine

CALCULATED PROPERTIES

JChem

• Acid pKa: 3.3686965
• H Acceptors: 5
• H Donor: 4
• LogD (pH = 5.5): -3.1288266
• LogD (pH = 7.4): -3.1262124
• Log P: -3.1262057
• Molar Refractivity: 36.718 cm^3
• Polarizability: 9.945617 Å^3
• Polar Surface Area: 99.2 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: -1.76
• LOG S: -1.45
• Solubility (Water): 4.19e+00 g/l

PROPERTIES

Physical Property

• Apperance: White crystals
• Melting Point: 300 °C(lit.); 300°C; ca 280°C dec.
• Partition Coefficient: -1.11
• pKa: 3.414
• pKb: 10.583
• Odor: Odourless

Safety Information

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38; r36/37/38
• Safety Statements: 26-36; 26-37; s26, s36
• TSCA Listed: 否
• GHS Pictograms: GHS exclamation mark; GHS07
• GHS Signal Word: WARNING; Warning
• GHS Hazard statements: 315, 319, 335; H315-H319-H335
• GHS Precautionary statements: 261, 305+351+338; P261-P305 + P351 + P338; P261-P305+P351+P338-P302+P352-P321-P405-P501A
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Purity: 99%; 99+%
• Linear Formula: H2NC(=NH)NHCH2CO2H

DETAILS

MP Biomedicals - 05203408

MP Biomedicals Rare Chemical collection

MP Biomedicals - 02101918

Crystalline

DrugBank - DB02751

Drug information: experimental

Sigma Aldrich - G11608

Packaging
25, 100 g in poly bottle
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. G11608.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Toronto Research Chemicals - G821250

An important marker for renal failure, in kidney transplantation, and for the renal metabolic activity.

REFERENCES

• Zugno, A., et al.: Neurochem. Res., 33, 1804 (2008)
• Debray, F., et al.: Neurol., 71, 44 (2008)
• da Silva, R., et al.: Am. J. Physiol., 296, E256 (2008)