tetrasodium {[(2R,3S,5R)-5-(6-amino-9H-purin-9-yl)-2-methyloxolan-3-yl phosphonato]oxy}(phosphonatooxy)phosphinate

• ChemBase ID: 133728
• Molecular Formular: C10H12N5Na4O11P3
• Molecular Mass: 563.109543
• Monoisotopic Mass: 562.93369324
• SMILES: C[C@@H]1[C@H](C[C@@H](O1)n1cnc2c1ncnc2N)OP(=O)([O-])OP(=O)([O-])OP(=O)([O-])[O-].[Na+].[Na+].[Na+].[Na+]
• Canonical SMILES: C[C@H]1O[C@H](C[C@@H]1OP(=O)(OP(=O)(OP(=O)([O-])[O-])[O-])[O-])n1cnc2c1ncnc2N.[Na+].[Na+].[Na+].[Na+]
• InChI: InChI=1S/C10H16N5O11P3.4Na/c1-5-6(24-28(19,20)26-29(21,22)25-27(16,17)18)2-7(23-5)15-4-14-8-9(11)12-3-13-10(8)15;;;;/h3-7H,2H2,1H3,(H,19,20)(H,21,22)(H2,11,12,13)(H2,16,17,18);;;;/q;4*+1/p-4/t5-,6+,7-;;;;/m1..../s1
• InChIKey: BKMXLPGGJURCPM-DNGRLYOHSA-J

NAMES AND DATABASE IDS

Names

• IUPAC name: tetrasodium {[(2R,3S,5R)-5-(6-amino-9H-purin-9-yl)-2-methyloxolan-3-yl phosphonato]oxy}(phosphonatooxy)phosphinate
• IUPAC Traditional name: tetrasodium [(2R,3S,5R)-5-(6-aminopurin-9-yl)-2-methyloxolan-3-yl phosphonato]oxy(phosphonatooxy)phosphinate
• Synonyms: 2′,5′-Dideoxy-3′-ATP; 2′,5′-Dideoxyadenosine 3′-triphosphate; 2′,5′-Dideoxyadenosine 3′-triphosphate tetrasodium salt

Database IDs

• MDL Number: MFCD11044462
• PubChem SID: 24724456; 162228005
• PubChem CID: 16078966

CALCULATED PROPERTIES

• Acid pKa: 0.89300984
• H Acceptors: 12
• H Donor: 1
• LogD (pH = 5.5): -7.894003
• LogD (pH = 7.4): -8.5225115
• Log P: -4.0546308
• Molar Refractivity: 88.2731 cm^3
• Polarizability: 36.698494 Å^3
• Polar Surface Area: 249.99 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: H2O: soluble24 mg/mL
• Apperance: off-white, 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: >91% (HPLC)

DETAILS

Sigma Aldrich - D0939

Biochem/physiol Actions
Potent inhibitor of adenylyl cyclase. Not cell-permeable. IC50 = 40 nM in detergent-dispersed rat brain preparation.