2-(2-iminoimidazolidin-1-yl)acetic acid

• ChemBase ID: 92963
• Molecular Formular: C5H9N3O2
• Molecular Mass: 143.14386
• Monoisotopic Mass: 143.06947654
• SMILES: N1CCN(C1=N)CC(=O)O
• Canonical SMILES: OC(=O)CN1CCNC1=N
• InChI: InChI=1S/C5H9N3O2/c6-5-7-1-2-8(5)3-4(9)10/h1-3H2,(H2,6,7)(H,9,10)
• InChIKey: AMHZIUVRYRVYBA-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-(2-iminoimidazolidin-1-yl)acetic acid
• IUPAC Traditional name: (2-iminoimidazolidin-1-yl)acetic acid
• Synonyms: 2-Amino-4,5-dihydro-1H-Imidazole-1-acetic Acid; Cyclocreatine; 1-Carboxymethyl-2-iminoimidazolidine; 2-Imino-1-imidazolidineacetic acid; Cyclocreatine; 1-(Carboxymethyl)-2-iminoimidazolidine; (2-Iminoimidazolidin-1-yl)acetic acid; 环肌酸; 2-亚氨基-1-咪唑啉乙酸

Database IDs

• CAS Number: 35404-50-3
• MDL Number: MFCD00134455
• PubChem SID: 24863514; 162079661
• PubChem CID: 2896

CALCULATED PROPERTIES

• Acid pKa: 3.3714743
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): -2.760783
• LogD (pH = 7.4): -2.7581584
• Log P: -2.758171
• Molar Refractivity: 44.8183 cm^3
• Polarizability: 12.861022 Å^3
• Polar Surface Area: 76.42 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Water
• Apperance: White Solid
• Melting Point: >300°C (dec.); 300(dec.)°C

Safety Information

• Storage Condition: -20°C Freezer
• Storage Warning: Irritant/Store at -20°C
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-37/39
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Purity: 98%
• Empirical Formula (Hill Notation): C5H9N3O2

DETAILS

Apollo Scientific Ltd - OR9822T

Regulates creatine biosynthesis by suppressing the level of arginine:glycine aminotransferase.

Sigma Aldrich - 377627

Packaging
1, 5 g in glass bottle
Application
Protectant against inhibition of cardiac mitochondrial respiration by methylglyoxal1Growth inhibition of Hodgkin disease-derived cell lines2Investigations into effects in rat hepatocarcinogenesis model3
Biochem/physiol Actions
Creatine analog that protects tissues from ischemic damage; decreases the rate of ATP production via creatine kinase and reduces the proliferation of tumor cell lines that are characterized by high levels of creatine kinase expression.

Toronto Research Chemicals - C982200

Can regulate creatine biosynthesis by suppressing the level of arginine:glycine amidinotransferase in chick liver.

REFERENCES

• McGilvery, R.W. et al.: J. Biol. Chem., 249, 1417 (1974)