9-{2,7-dihydroxy-2-oxo-hexahydro-1,3,5,2λ5-furo[3,2-d][1,3,2λ5]dioxaphosphinin-6-yl}-2,3,6,9-tetrahydro-1H-purine-2,6-dione

• ChemBase ID: 155711
• Molecular Formular: C10H11N4O8P
• Molecular Mass: 346.190101
• Monoisotopic Mass: 346.03144996
• SMILES: c1nc2c(n1C1C(C3C(O1)COP(=O)(O3)O)O)[nH]c(=O)[nH]c2=O
• Canonical SMILES: O=c1[nH]c(=O)c2c([nH]1)n(cn2)C1OC2C(C1O)OP(=O)(OC2)O
• InChI: InChI=1S/C10H11N4O8P/c15-5-6-3(1-20-23(18,19)22-6)21-9(5)14-2-11-4-7(14)12-10(17)13-8(4)16/h2-3,5-6,9,15H,1H2,(H,18,19)(H2,12,13,16,17)
• InChIKey: AAUQFLOPCIXUSK-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 9-{2,7-dihydroxy-2-oxo-hexahydro-1,3,5,2λ^5-furo[3,2-d][1,3,2λ^5]dioxaphosphinin-6-yl}-2,3,6,9-tetrahydro-1H-purine-2,6-dione
• IUPAC Traditional name: 9-{2,7-dihydroxy-2-oxo-tetrahydro-4H-1,3,5,2λ^5-furo[3,2-d][1,3,2λ^5]dioxaphosphinin-6-yl}-1,3-dihydropurine-2,6-dione
• Synonyms: cXMP; Xanthosine 3′,5′-cyclic monophosphate

Database IDs

• CAS Number: 31319-70-7
• MDL Number: MFCD03453038
• PubChem SID: 162249849; 24902139
• PubChem CID: 4139017

CALCULATED PROPERTIES

• Acid pKa: 1.8406738
• H Acceptors: 7
• H Donor: 4
• LogD (pH = 5.5): -3.3883023
• LogD (pH = 7.4): -3.4195073
• Log P: -1.1393197
• Molar Refractivity: 69.3024 cm^3
• Polarizability: 27.178978 Å^3
• Polar Surface Area: 161.24 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Apperance: solid

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Product Information

• Purity: ≥98% (HPLC)
• Packaging: vial of 2 mg
• Mol. Weight: apparent mol wt 367.2

DETAILS

Sigma Aldrich - X3003

Biochem/physiol Actions
cXMP is a an analog of cyclic GMP that is used to evaluate phosphodiesterase activity.