({[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3-(4-benzoylbenzoyloxy)-4-hydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)phosphonic acid; triethylamine

• ChemBase ID: 132416
• Molecular Formular: C30H39N6O15P3
• Molecular Mass: 816.583143
• Monoisotopic Mass: 816.16862447
• SMILES: CCN(CC)CC.c1ccc(cc1)C(=O)c1ccc(cc1)C(=O)O[C@@H]1[C@H](O[C@H]([C@@H]1O)n1cnc2c1ncnc2N)COP(=O)(O)OP(=O)(O)OP(=O)(O)O
• Canonical SMILES: O[C@@H]1[C@H](OC(=O)c2ccc(cc2)C(=O)c2ccccc2)[C@H](O[C@H]1n1cnc2c1ncnc2N)COP(=O)(OP(=O)(OP(=O)(O)O)O)O.CCN(CC)CC
• InChI: InChI=1S/C24H24N5O15P3.C6H15N/c25-21-17-22(27-11-26-21)29(12-28-17)23-19(31)20(16(41-23)10-40-46(36,37)44-47(38,39)43-45(33,34)35)42-24(32)15-8-6-14(7-9-15)18(30)13-4-2-1-3-5-13;1-4-7(5-2)6-3/h1-9,11-12,16,19-20,23,31H,10H2,(H,36,37)(H,38,39)(H2,25,26,27)(H2,33,34,35);4-6H2,1-3H3/t16-,19-,20-,23-;/m1./s1
• InChIKey: HVOVBTNCGADRTH-WBLDMZOZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: ({[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3-(4-benzoylbenzoyloxy)-4-hydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)phosphonic acid; triethylamine
• IUPAC Traditional name: BzATP; triethylamine
• Synonyms: Benzoylbenzoyl-ATP; Bz-ATP; 2′(3′)-O-(4-Benzoylbenzoyl)adenosine 5′-triphosphate triethylammonium salt

Database IDs

• CAS Number: 112898-15-4
• MDL Number: MFCD00058547
• PubChem SID: 162226693
• PubChem CID: 71308559

CALCULATED PROPERTIES

• Acid pKa: 0.89524955
• H Acceptors: 15
• H Donor: 6
• LogD (pH = 5.5): -5.8753133
• LogD (pH = 7.4): -6.51515
• Log P: -2.0429828
• Molar Refractivity: 156.2118 cm^3
• Polarizability: 61.393444 Å^3
• Polar Surface Area: 302.27 Å^2
• Rotatable Bonds: 16
• 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

• Purity: ~95%

DETAILS

Sigma Aldrich - B6396

Application
Useful as a photoaffinity label for proteins and enzymes that bind ATP.1
Biochem/physiol Actions
Selective P2X purinergic agonist. It is more potent than ATP at homodimeric P2X7 receptors.
Other Notes
Mixed isomers