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

• ChemBase ID: 155213
• Molecular Formular: C20H30N11O16P3
• Molecular Mass: 773.437583
• Monoisotopic Mass: 773.10848383
• SMILES: c1nc(c2c(n1)n(cn2)C1C(C(C(O1)COP(=O)(O)OP(=O)(O)OP(=O)(O)OCC1C(C(C(O1)n1cnc2c1ncnc2N)O)O)O)O)N.N
• Canonical SMILES: OC1C(COP(=O)(OP(=O)(OP(=O)(OCC2OC(C(C2O)O)n2cnc3c2ncnc3N)O)O)O)OC(C1O)n1cnc2c1ncnc2N.N
• InChI: InChI=1S/C20H27N10O16P3.H3N/c21-15-9-17(25-3-23-15)29(5-27-9)19-13(33)11(31)7(43-19)1-41-47(35,36)45-49(39,40)46-48(37,38)42-2-8-12(32)14(34)20(44-8)30-6-28-10-16(22)24-4-26-18(10)30;/h3-8,11-14,19-20,31-34H,1-2H2,(H,35,36)(H,37,38)(H,39,40)(H2,21,23,25)(H2,22,24,26);1H3
• InChIKey: PKSQTRWRSNNYCW-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: {[5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}({[({[5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)phosphinic acid amine
• IUPAC Traditional name: ApppA amine
• Synonyms: A(5′)P3(5′)A; Diadenosine triphosphate; P1,P3-Di(adenosine-5′) triphosphate ammonium salt

Database IDs

• CAS Number: 102783-40-4
• MDL Number: MFCD00058130
• PubChem SID: 162249351; 24893423
• PubChem CID: 16219211

CALCULATED PROPERTIES

• Acid pKa: 0.9007216
• H Acceptors: 20
• H Donor: 9
• LogD (pH = 5.5): -11.065815
• LogD (pH = 7.4): -11.37538
• Log P: -9.487444
• Molar Refractivity: 155.2309 cm^3
• Polarizability: 61.90963 Å^3
• Polar Surface Area: 387.44 Å^2
• Rotatable Bonds: 12
• Lipinski's Rule of Five: false

PROPERTIES

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

• Impurities: Other adenosine phosphates, essentially free
• Linear Formula: C20H24N9O16P3 · NH3

DETAILS

Sigma Aldrich - D1387

Quantity
Approx. 25 A260 units per mg.
Application
P1,P3-Di(adenosine-5′) triphosphate (Ap3A) is a diadenosine oligophosphate (ApnA) family member. ApnAs have been found to act as a signaling molecule.