{[3,4-dihydroxy-5-(6-oxo-6,9-dihydro-3H-purin-9-yl)oxolan-2-yl]methoxy}phosphonic acid

• ChemBase ID: 132470
• Molecular Formular: C10H13N4O8P
• Molecular Mass: 348.205981
• Monoisotopic Mass: 348.04710003
• SMILES: c1[nH]c2c(c(=O)n1)ncn2C1C(C(C(O1)COP(=O)(O)O)O)O
• Canonical SMILES: OC1C(O)C(OC1n1cnc2c1[nH]cnc2=O)COP(=O)(O)O
• InChI: InChI=1S/C10H13N4O8P/c15-6-4(1-21-23(18,19)20)22-10(7(6)16)14-3-13-5-8(14)11-2-12-9(5)17/h2-4,6-7,10,15-16H,1H2,(H,11,12,17)(H2,18,19,20)
• InChIKey: GRSZFWQUAKGDAV-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: {[3,4-dihydroxy-5-(6-oxo-6,9-dihydro-3H-purin-9-yl)oxolan-2-yl]methoxy}phosphonic acid
• IUPAC Traditional name: inosinic acid
• Synonyms: I-5′-P; IMP; Inosinic Acid; Inosine 5′-monophosphate from Saccharomyces cerevisiae

Database IDs

• CAS Number: 131-99-7
• EC Number: 205-045-1
• MDL Number: MFCD00066754
• PubChem SID: 24896014; 162226747
• PubChem CID: 797

CALCULATED PROPERTIES

• Acid pKa: 1.211522
• H Acceptors: 10
• H Donor: 5
• LogD (pH = 5.5): -4.5417647
• LogD (pH = 7.4): -6.146004
• Log P: -3.5082972
• Molar Refractivity: 71.7713 cm^3
• Polarizability: 27.93058 Å^3
• Polar Surface Area: 175.73 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

• German water hazard class: 2
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Product Information

• Purity: ≥98%
• Type: Grade V

DETAILS

Sigma Aldrich - I2879

Application
Inosine 5′-monophosphate (IMP) is used as a substrate to study the distribution, specificity and kinetics of inosine-5′-monophosphate dehydrogenase (IMPDH).