trisodium (2R,3S,5R)-5-(6-amino-9H-purin-9-yl)-2-methyloxolan-3-yl (phosphonatooxy)phosphonate

• ChemBase ID: 153305
• Molecular Formular: C10H12N5Na3O8P2
• Molecular Mass: 461.147812
• Monoisotopic Mass: 460.98541847
• SMILES: C[C@@H]1[C@H](C[C@@H](O1)n1cnc2c1ncnc2N)OP(=O)([O-])OP(=O)([O-])[O-].[Na+].[Na+].[Na+]
• Canonical SMILES: C[C@H]1O[C@H](C[C@@H]1OP(=O)(OP(=O)([O-])[O-])[O-])n1cnc2c1ncnc2N.[Na+].[Na+].[Na+]
• InChI: InChI=1S/C10H15N5O8P2.3Na/c1-5-6(22-25(19,20)23-24(16,17)18)2-7(21-5)15-4-14-8-9(11)12-3-13-10(8)15;;;/h3-7H,2H2,1H3,(H,19,20)(H2,11,12,13)(H2,16,17,18);;;/q;3*+1/p-3/t5-,6+,7-;;;/m1.../s1
• InChIKey: DIRFRXIQHKVAEX-RRQIASHOSA-K

NAMES AND DATABASE IDS

Names

• IUPAC name: trisodium (2R,3S,5R)-5-(6-amino-9H-purin-9-yl)-2-methyloxolan-3-yl (phosphonatooxy)phosphonate
• IUPAC Traditional name: trisodium (2R,3S,5R)-5-(6-aminopurin-9-yl)-2-methyloxolan-3-yl phosphonatooxyphosphonate
• Synonyms: 2′,5′-Dideoxy-3′-ADP; 2′,5′-dd-3′-ADP; 2′,5′-Dideoxyadenosine 3′-diphosphate trisodium salt

Database IDs

• MDL Number: MFCD11044461
• PubChem SID: 162247444; 24893301
• PubChem CID: 16219203

CALCULATED PROPERTIES

• Acid pKa: 1.7613425
• H Acceptors: 10
• H Donor: 1
• LogD (pH = 5.5): -5.1975346
• LogD (pH = 7.4): -5.7245727
• Log P: -3.0420845
• Molar Refractivity: 78.5219 cm^3
• Polarizability: 32.045715 Å^3
• Polar Surface Area: 200.63 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: H2O: soluble
• Apperance: off-white

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

• Empirical Formula (Hill Notation): C10H12Na3N5O8P2

DETAILS

Sigma Aldrich - D0814

Application
Potent inhibitor of adenylyl cyclase. Not cell-permeable. Precursor to 2′,5′-Dideoxyadenosine 3′-triphosphate (Prod. No. D0939). IC50 = 100 nM in detergent-dispersed rat brain preparation.