disodium [(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl (hydrogen phosphonatooxy)phosphonate

• ChemBase ID: 159568
• Molecular Formular: C10H13N5Na2O10P2
• Molecular Mass: 471.164782
• Monoisotopic Mass: 470.99330346
• SMILES: n1cnc2c(c1N)ncn2[C@H]1[C@@H]([C@@H]([C@H](O1)COP(=O)(OP(=O)(O)[O-])[O-])O)O.[Na+].[Na+]
• Canonical SMILES: O[C@@H]1[C@@H](COP(=O)(OP(=O)(O)[O-])[O-])O[C@H]([C@@H]1O)n1cnc2c1ncnc2N.[Na+].[Na+]
• InChI: InChI=1S/C10H15N5O10P2.2Na/c11-8-5-9(13-2-12-8)15(3-14-5)10-7(17)6(16)4(24-10)1-23-27(21,22)25-26(18,19)20;;/h2-4,6-7,10,16-17H,1H2,(H,21,22)(H2,11,12,13)(H2,18,19,20);;/q;2*+1/p-2/t4-,6-,7-,10-;;/m1../s1
• InChIKey: ORKSTPSQHZNDSC-IDIVVRGQSA-L

NAMES AND DATABASE IDS

Names

• IUPAC name: disodium [(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl (hydrogen phosphonatooxy)phosphonate
• IUPAC Traditional name: disodium [(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl hydrogen phosphonatooxyphosphonate
• Synonyms: Adenosine 5'-(Trihydrogen Diphosphate) Disodium Salt Hydrate; Adenosine-5'-(Trihydrogen Pyrophosphate) Disodium Salt Hydrate; ADP Disodium Salt Hydrate; Disodium 5'-ADP Hydrate; Disodium ADP Hydrate; Disodium Adenosine 5'-Diphosphate Hydrate; Trinosin S Hydrate; Adenosine 5'-Diphosphate Disodium Salt Hydrate

Database IDs

• PubChem SID: 162253703
• PubChem CID: 85315

CALCULATED PROPERTIES

• Acid pKa: 1.7714783
• H Acceptors: 12
• H Donor: 4
• LogD (pH = 5.5): -7.1348915
• LogD (pH = 7.4): -7.671735
• Log P: -4.982523
• Molar Refractivity: 82.698 cm^3
• Polarizability: 33.615604 Å^3
• Polar Surface Area: 238.26 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - A281700

A nucleoside diphosphate that interacts with a family of ADP receptors found on platelets (P2Y1, P2Y12 and P2X1), to induce platelet activation. ADP in the blood is converted to adenosine by the action of ecto-ADPases, inhibiting further platelet activati

REFERENCES

• Gamba, G. et al.: Haematologia, 58, 1215 (1973)
• Dejana, E. et al.: Thromb. Haemost., 39, 135 (1973)