{[2-(6-amino-9H-purin-9-yl)-4-hydroxy-5-[(phosphonooxy)methyl]oxolan-3-yl]oxy}phosphonic acid sodium

• ChemBase ID: 133455
• Molecular Formular: C10H15N5NaO10P2
• Molecular Mass: 450.190892
• Monoisotopic Mass: 450.01918425
• SMILES: c1nc(c2c(n1)n(cn2)C1C(C(C(O1)COP(=O)(O)O)O)OP(=O)(O)O)N.[Na]
• Canonical SMILES: OC1C(COP(=O)(O)O)OC(C1OP(=O)(O)O)n1cnc2c1ncnc2N.[Na]
• InChI: InChI=1S/C10H15N5O10P2.Na/c11-8-5-9(13-2-12-8)15(3-14-5)10-7(25-27(20,21)22)6(16)4(24-10)1-23-26(17,18)19;/h2-4,6-7,10,16H,1H2,(H2,11,12,13)(H2,17,18,19)(H2,20,21,22)
• InChIKey: OHPUPSOOFQPMRP-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: {[2-(6-amino-9H-purin-9-yl)-4-hydroxy-5-[(phosphonooxy)methyl]oxolan-3-yl]oxy}phosphonic acid sodium
• IUPAC Traditional name: [2-(6-aminopurin-9-yl)-4-hydroxy-5-[(phosphonooxy)methyl]oxolan-3-yl]oxyphosphonic acid sodium
• Synonyms: 2′-Phosphoadenosine 5′-phosphate sodium salt; Adenosine 2′,5′-diphosphate sodium salt

Database IDs

• CAS Number: 154146-84-6
• PubChem SID: 24891005; 162227732
• PubChem CID: 16218927

CALCULATED PROPERTIES

• Acid pKa: 0.57364166
• H Acceptors: 12
• H Donor: 6
• LogD (pH = 5.5): -7.4545074
• LogD (pH = 7.4): -9.858249
• Log P: -4.936711
• Molar Refractivity: 84.9414 cm^3
• Polarizability: 33.697124 Å^3
• Polar Surface Area: 232.6 Å^2
• Rotatable Bonds: 6
• 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 - A5638

Application
Adenosine 2′,5′-diphosphate is a competitive antagonist of P2Y1 receptor and a non-selective antagonist of the platelet P2X1 ion channel and it may be used to study the mechanisms and activities of these components. Adenosine 2′,5′-diphosphate may be used to prepare adenosine 2′,5′-diphosphate agarose for affinity chromatography purification of enzymes such as NADPH-cytochrome P450 reductase and glutathione reductase.