[({[5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)methyl]phosphonic acid sodium

• ChemBase ID: 132381
• Molecular Formular: C11H17N5NaO9P2
• Molecular Mass: 448.218072
• Monoisotopic Mass: 448.03991969
• SMILES: c1nc(c2c(n1)n(cn2)C1C(C(C(O1)COP(=O)(CP(=O)(O)O)O)O)O)N.[Na]
• Canonical SMILES: OC1C(COP(=O)(CP(=O)(O)O)O)OC(C1O)n1cnc2c1ncnc2N.[Na]
• InChI: InChI=1S/C11H17N5O9P2.Na/c12-9-6-10(14-2-13-9)16(3-15-6)11-8(18)7(17)5(25-11)1-24-27(22,23)4-26(19,20)21;/h2-3,5,7-8,11,17-18H,1,4H2,(H,22,23)(H2,12,13,14)(H2,19,20,21)
• InChIKey: GOSSLHVOVYFOAJ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [({[5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)methyl]phosphonic acid sodium
• IUPAC Traditional name: {[5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy(hydroxy)phosphoryl}methylphosphonic acid sodium
• Synonyms: AMP-CP; α,β-Methyleneadenosine 5′-diphosphate sodium salt

Database IDs

• CAS Number: 104835-70-3
• MDL Number: MFCD00070019
• PubChem SID: 24897249; 162226658
• PubChem CID: 16219694

CALCULATED PROPERTIES

• Acid pKa: 0.98112744
• H Acceptors: 12
• H Donor: 6
• LogD (pH = 5.5): -8.182416
• LogD (pH = 7.4): -8.16192
• Log P: -5.8846297
• Molar Refractivity: 87.2951 cm^3
• Polarizability: 34.85279 Å^3
• Polar Surface Area: 223.37 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• German water hazard class: 3
• Storage Temperature: -20°C

DETAILS

Sigma Aldrich - M8386

Application
α,β-Methyleneadenosine 5′-diphosphate (AMP-CP) is a CD73 inhibitor and is used to study adenosinergic signaling regulation via CD73/ecto-5′-nucleotidase.