2,2-bis(carbamoylamino)acetic acid

• ChemBase ID: 107684
• Molecular Formular: C4H8N4O4
• Molecular Mass: 176.13072
• Monoisotopic Mass: 176.05455476
• SMILES: NC(=O)NC(NC(=O)N)C(=O)O
• Canonical SMILES: OC(=O)C(NC(=O)N)NC(=O)N
• InChI: InChI=1S/C4H8N4O4/c5-3(11)7-1(2(9)10)8-4(6)12/h1H,(H,9,10)(H3,5,7,11)(H3,6,8,12)
• InChIKey: NUCLJNSWZCHRKL-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2,2-bis(carbamoylamino)acetic acid
• IUPAC Systematic name: 2,2-Bis(carbamoylamino)acetic acid
• IUPAC Traditional name: allantoic acid
• Synonyms: 2,2-Di[(aminocarbonyl)amino]acetic acid; Diureidoacetate; ALLANTOIC ACID; 2,2-Bis[(aminocarbonyl)amino]acetic Acid; Diureido-acetic Acid

Database IDs

• CAS Number: 99-16-1
• EC Number: 202-735-4
• Beilstein Number: 1790227
• PubChem SID: 162094092
• PubChem CID: 203
• CHEBI ID: 30837
• Chemspider ID: 198
• Gmelin ID: 240954
• KEGG ID: C00499
• MeSH Name: allantoic+acid
• Wikipedia Title: Allantoic_acid

CALCULATED PROPERTIES

• Acid pKa: 3.2398093
• H Acceptors: 4
• H Donor: 5
• LogD (pH = 5.5): -4.8123093
• LogD (pH = 7.4): -6.010664
• Log P: -2.572495
• Molar Refractivity: 35.1003 cm^3
• Polarizability: 13.726167 Å^3
• Polar Surface Area: 147.54 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Flash Point: 219.4 °C
• Density: 1.618 g mL^-1

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - A541500

An metabolic intermediate in nucleic acid metabolism.

REFERENCES

• Yoon, K., et al.: Nat. Prod. Sci., 14, 254 (2008)
• Ramazzina, I., et al.: J. Biol. Chem., 283, 23295 (2008)
• Kim, K., et al.: J. Mol. Biol., 387, 1067 (2008)