4-({6-[6-(3-carboxypropanamido)-9H-purin-9-yl]-2-hydroxy-2-oxo-hexahydro-1,3,5,2λ5-furo[3,2-d][1,3,2λ5]dioxaphosphinin-7-yl}oxy)-4-oxobutanoic acid sodium

• ChemBase ID: 132139
• Molecular Formular: C18H20N5NaO12P
• Molecular Mass: 552.341231
• Monoisotopic Mass: 552.07437702
• SMILES: c1nc(c2c(n1)n(cn2)C1C(C2C(O1)COP(=O)(O2)O)OC(=O)CCC(=O)O)NC(=O)CCC(=O)O.[Na]
• Canonical SMILES: OC(=O)CCC(=O)OC1C2OP(=O)(O)OCC2OC1n1cnc2c1ncnc2NC(=O)CCC(=O)O.[Na]
• InChI: InChI=1S/C18H20N5O12P.Na/c24-9(1-2-10(25)26)22-16-13-17(20-6-19-16)23(7-21-13)18-15(34-12(29)4-3-11(27)28)14-8(33-18)5-32-36(30,31)35-14;/h6-8,14-15,18H,1-5H2,(H,25,26)(H,27,28)(H,30,31)(H,19,20,22,24)
• InChIKey: JZQVPHUIEVDOIX-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-({6-[6-(3-carboxypropanamido)-9H-purin-9-yl]-2-hydroxy-2-oxo-hexahydro-1,3,5,2λ^5-furo[3,2-d][1,3,2λ^5]dioxaphosphinin-7-yl}oxy)-4-oxobutanoic acid sodium
• IUPAC Traditional name: 4-({6-[6-(3-carboxypropanamido)purin-9-yl]-2-hydroxy-2-oxo-tetrahydro-4H-1,3,5,2λ^5-furo[3,2-d][1,3,2λ^5]dioxaphosphinin-7-yl}oxy)-4-oxobutanoic acid sodium
• Synonyms: Disuccinyl-cAMP; N6,2′-O-Disuccinyladenosine 3′:5′-cyclic monophosphate sodium salt

Database IDs

• CAS Number: 102783-27-7
• MDL Number: MFCD00057109
• PubChem SID: 162226416; 24893281
• PubChem CID: 16219197

CALCULATED PROPERTIES

• Acid pKa: 1.8155
• H Acceptors: 12
• H Donor: 4
• LogD (pH = 5.5): -7.022614
• LogD (pH = 7.4): -10.09495
• Log P: -3.1178758
• Molar Refractivity: 111.3902 cm^3
• Polarizability: 44.232506 Å^3
• Polar Surface Area: 238.59 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

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

Product Information

• Purity: ~98%

DETAILS

Sigma Aldrich - D0635

Application
Starting material for synthesis of a wide range of cyclic-AMP derivatives: chemiluminescent conjugates, affinity matrices, etc.1