pentasodium ({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl phosphonato}oxy)[({[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl phosphonato}oxy)phosphinato]oxy}phosphinato)oxy]phosphinate

• ChemBase ID: 155104
• Molecular Formular: C20H24N10Na5O22P5
• Molecular Mass: 1026.276015
• Monoisotopic Mass: 1025.92431701
• 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-])OP(=O)([O-])OC[C@@H]1[C@H]([C@H]([C@@H](O1)n1cnc2c1ncnc2N)O)O)O)O)N.[Na+].[Na+].[Na+].[Na+].[Na+]
• Canonical SMILES: O[C@@H]1[C@@H](COP(=O)(OP(=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-])O[C@H]([C@@H]1O)n1cnc2c1ncnc2N.[Na+].[Na+].[Na+].[Na+].[Na+]
• InChI: InChI=1S/C20H29N10O22P5.5Na/c21-15-9-17(25-3-23-15)29(5-27-9)19-13(33)11(31)7(47-19)1-45-53(35,36)49-55(39,40)51-57(43,44)52-56(41,42)50-54(37,38)46-2-8-12(32)14(34)20(48-8)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)(H,43,44)(H2,21,23,25)(H2,22,24,26);;;;;/q;5*+1/p-5/t7-,8-,11-,12-,13-,14-,19-,20-;;;;;/m1...../s1
• InChIKey: NNMFUJJMJIYTSP-CSMIRWGRSA-I

NAMES AND DATABASE IDS

Names

• IUPAC name: pentasodium ({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl phosphonato}oxy)[({[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl phosphonato}oxy)phosphinato]oxy}phosphinato)oxy]phosphinate
• IUPAC Traditional name: pentasodium Ap5A
• Synonyms: A(5′)P5(5′)A; Diadenosine pentaphosphate pentasodium salt; P1,P5-Di(adenosine-5′) pentaphosphate pentasodium salt

Database IDs

• CAS Number: 4097-04-5
• EC Number: 223-852-7
• MDL Number: MFCD00077718
• Beilstein Number: 4949216
• PubChem SID: 162249242; 24893808
• PubChem CID: 16219241

CALCULATED PROPERTIES

• Acid pKa: 0.4076155
• H Acceptors: 24
• H Donor: 6
• LogD (pH = 5.5): -16.54053
• LogD (pH = 7.4): -16.970062
• Log P: -10.989128
• Molar Refractivity: 171.3682 cm^3
• Polarizability: 70.863716 Å^3
• Polar Surface Area: 494.65 Å^2
• Rotatable Bonds: 16
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: H2O: soluble50 mg/mL; H2O: soluble50 mg/mL, clear, slightly yellow
• Apperance: white to white with yellow cast powder

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

• Purity: ≥95% (HPLC); ≥96.0% (HPLC)
• Linear Formula: C20H29N10O22P5 · 5 Na

DETAILS

Sigma Aldrich - D4022

Biochem/physiol Actions
A diadenosine polyphosphate 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. In the nervous system it acts through various purinergic receptors. It also activates 5′-nucleotidase and inhibits adenosine kinase activity in vitro. Ap5A is metabolized by soluble enzymes in the blood plasma and by membrane-bound ectoenzymes of a number of cell types including endothelial and smooth muscle cells. In cardiac muscle, pM to nM concentrations significantly increase the open-probability of ryanodine-receptor (RyR2) gates, with prolonged action due to slow dissociation from the receptor.1

Sigma Aldrich - 31588

Biochem/physiol Actions
A diadenosine polyphosphate 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. In the nervous system it acts through various purinergic receptors. It also activates 5′-nucleotidase and inhibits adenosine kinase activity in vitro. Ap5A is metabolized by soluble enzymes in the blood plasma and by membrane-bound ectoenzymes of a number of cell types including endothelial and smooth muscle cells. In cardiac muscle, pM to nM concentrations significantly increase the open-probability of ryanodine-receptor (RyR2) gates, with prolonged action due to slow dissociation from the receptor.1