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

• ChemBase ID: 155171
• Molecular Formular: C20H31N11O19P4
• Molecular Mass: 853.417484
• Monoisotopic Mass: 853.07481435
• SMILES: c1nc(c2c(n1)n(cn2)[C@H]1[C@@H]([C@@H]([C@H](O1)COP(=O)(O)OP(=O)(O)OP(=O)(O)OP(=O)(O)OC[C@@H]1[C@H]([C@H]([C@@H](O1)n1cnc2c1ncnc2N)O)O)O)O)N.N
• Canonical SMILES: O[C@@H]1[C@@H](COP(=O)(OP(=O)(OP(=O)(OP(=O)(OC[C@H]2O[C@H]([C@@H]([C@@H]2O)O)n2cnc3c2ncnc3N)O)O)O)O)O[C@H]([C@@H]1O)n1cnc2c1ncnc2N.N
• InChI: InChI=1S/C20H28N10O19P4.H3N/c21-15-9-17(25-3-23-15)29(5-27-9)19-13(33)11(31)7(45-19)1-43-50(35,36)47-52(39,40)49-53(41,42)48-51(37,38)44-2-8-12(32)14(34)20(46-8)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)(H,41,42)(H2,21,23,25)(H2,22,24,26);1H3/t7-,8-,11-,12-,13-,14-,19-,20-;/m1./s1
• InChIKey: JTLRVYSRZSPJKJ-AHKIGRPSSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: {[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}({[({[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)(hydroxy)phosphoryl]oxy})phosphinic acid amine
• IUPAC Traditional name: appppa amine
• Synonyms: A(5′)p4(5′)A; Diadenosine tetraphosphate ammonium salt; P1,P4-Di(adenosine-5′) tetraphosphate ammonium salt

Database IDs

• CAS Number: 102783-36-8
• MDL Number: MFCD00058622
• PubChem SID: 24277711; 162249309
• PubChem CID: 71312091

CALCULATED PROPERTIES

• Acid pKa: 0.58866066
• H Acceptors: 22
• H Donor: 10
• LogD (pH = 5.5): -13.802533
• LogD (pH = 7.4): -14.172774
• Log P: -10.018653
• Molar Refractivity: 166.1038 cm^3
• Polarizability: 66.67729 Å^3
• Polar Surface Area: 433.97 Å^2
• Rotatable Bonds: 14
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: H2O: soluble50 mg/mL
• Apperance: white powder

Safety Information

• RTECS: AU7411600
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Pharmacology Properties

• Gene Information: human ... PLD1(5337), PLD2(5338), PLD3(23646), PLD4(122618), PLD5(200150)

Product Information

• Purity: ≥95% (HPLC)
• Empirical Formula (Hill Notation): C20H28N10O19P4 · xNH3

DETAILS

Sigma Aldrich - D1262

Biochem/physiol Actions
Diadenosine polyphosphate functions as a second messenger in pancreatic cells, stimulates phospholipase D, changes intracellular calcium levels, induces nitric oxide release, activates 5′-nucleotidase, and inhibits adenosine kinase activity in vitro.
Diadenosine polyphosphate is stored in secretory granules of thrombocytes, chromaffin, and neuronal cells. After release into the extracellular space, it affects a variety of biological activities in a wide range of target tissues. It appears to function as a second messenger in pancreatic cells. In rat liver cells. it stimulates phospholipase D and changes intracellular calcium levels. It has been shown to induce nitric oxide release from endothelial cells. In the nervous system it acts through various purinoceptors. It also activates 5′-nucleotidase and inhibits adenosine kinase activity in vitro. Ap4A is metabolized by soluble enzymes in the blood plasma and by membrane-bound ectoenzymes of a number of cell types including endothelial cells, smooth muscle cell.