disodium 1-(2-nitrophenyl)ethyl [({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl phosphonato)oxy]phosphonate

• ChemBase ID: 133831
• Molecular Formular: C18H21N6Na2O15P3
• Molecular Mass: 700.291363
• Monoisotopic Mass: 700.00731245
• SMILES: CC(c1ccccc1[N+](=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.[Na+].[Na+]
• Canonical SMILES: O[C@@H]1[C@@H](COP(=O)(OP(=O)(OP(=O)(OC(c2ccccc2[N+](=O)[O-])C)[O-])[O-])O)O[C@H]([C@@H]1O)n1cnc2c1ncnc2N.[Na+].[Na+]
• InChI: InChI=1S/C18H23N6O15P3.2Na/c1-9(10-4-2-3-5-11(10)24(27)28)37-41(31,32)39-42(33,34)38-40(29,30)35-6-12-14(25)15(26)18(36-12)23-8-22-13-16(19)20-7-21-17(13)23;;/h2-5,7-9,12,14-15,18,25-26H,6H2,1H3,(H,29,30)(H,31,32)(H,33,34)(H2,19,20,21);;/q;2*+1/p-2/t9?,12-,14-,15-,18-;;/m1../s1
• InChIKey: DWGOHIKVVKFGGU-DZHDPEGHSA-L

NAMES AND DATABASE IDS

Names

• IUPAC name: disodium 1-(2-nitrophenyl)ethyl [({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl phosphonato)oxy]phosphonate
• IUPAC Traditional name: disodium 1-(2-nitrophenyl)ethyl {[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy(hydroxy)phosphoryl phosphonato}oxyphosphonate
• Synonyms: “Caged” ATP; Adenosine 5′-triphosphate γ-(1-[2-nitrophenyl]ethyl) ester sodium salt

Database IDs

• CAS Number: 171800-68-3
• MDL Number: MFCD00077294
• PubChem SID: 24890911; 162228108
• PubChem CID: 16211021

CALCULATED PROPERTIES

• Acid pKa: 0.8971109
• H Acceptors: 15
• H Donor: 4
• LogD (pH = 5.5): -7.3313107
• LogD (pH = 7.4): -7.7208924
• Log P: -3.523246
• Molar Refractivity: 134.4093 cm^3
• Polarizability: 53.59529 Å^3
• Polar Surface Area: 319.61 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

• Purity: ≥95%

DETAILS

Sigma Aldrich - A4803

Application
Adenosine 5′-triphosphate γ-(1-[2-nitrophenyl]ethyl) ester (“Caged” ATP) is used as a photolyzing substrate of luciferase-mediated firefly bioluminescence and other ATP-dependent photolytic processes. Caged ATP has also been used to study the dynamics of ATP-driven linear molecular motors such as myosin Va.