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

• ChemBase ID: 134343
• Molecular Formular: C15H23N5NaO14P2
• Molecular Mass: 582.305512
• Monoisotopic Mass: 582.06144298
• SMILES: c1nc(c2c(n1)n(cn2)C1C(C(C(O1)COP(=O)(O)OP(=O)(O)OCC(C(C(C=O)O)O)O)O)O)N.[Na]
• Canonical SMILES: O=CC(C(C(COP(=O)(OP(=O)(OCC1OC(C(C1O)O)n1cnc2c1ncnc2N)O)O)O)O)O.[Na]
• InChI: InChI=1S/C15H23N5O14P2.Na/c16-13-9-14(18-4-17-13)20(5-19-9)15-12(26)11(25)8(33-15)3-32-36(29,30)34-35(27,28)31-2-7(23)10(24)6(22)1-21;/h1,4-8,10-12,15,22-26H,2-3H2,(H,27,28)(H,29,30)(H2,16,17,18)
• InChIKey: LVIWKNSMPKNKBI-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: {[5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}({hydroxy[(2,3,4-trihydroxy-5-oxopentyl)oxy]phosphoryl}oxy)phosphinic acid sodium
• IUPAC Traditional name: [5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy[hydroxy(2,3,4-trihydroxy-5-oxopentyl)oxyphosphoryl]oxyphosphinic acid sodium
• Synonyms: ADP-Ribose; Adenosine 5′-diphosphoribose sodium salt

Database IDs

• CAS Number: 68414-18-6
• MDL Number: MFCD00136017
• PubChem SID: 162228619; 24890449
• PubChem CID: 16218837

CALCULATED PROPERTIES

• Acid pKa: 1.8570358
• H Acceptors: 15
• H Donor: 8
• LogD (pH = 5.5): -9.13408
• LogD (pH = 7.4): -9.424441
• Log P: -7.5406756
• Molar Refractivity: 112.5455 cm^3
• Polarizability: 45.401363 Å^3
• Polar Surface Area: 299.36 Å^2
• Rotatable Bonds: 12
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36
• 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
• Storage Temperature: -20°C

Product Information

• Purity: ≥93%

DETAILS

Sigma Aldrich - A0752

Application
ADP-Ribose is used as the basic building block used as a substrate in the formation of poly(ADP-ribose) by members of the poly(ADP-ribose) polymerase (PARP) family. Poly(ADP-ribose) formation and degradation are an important components of DNA repair and apoptosis signaling.