disodium {[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl (hydrogen phosphonatomethyl)phosphonate

• ChemBase ID: 132897
• Molecular Formular: C11H16N5Na2O12P3
• Molecular Mass: 549.171863
• Monoisotopic Mass: 548.98036943
• SMILES: c1nc(c2c(n1)n(cn2)[C@H]1[C@@H]([C@@H]([C@H](O1)COP(=O)(O)OP(=O)(CP(=O)(O)[O-])[O-])O)O)N.[Na+].[Na+]
• Canonical SMILES: O[C@@H]1[C@@H](COP(=O)(OP(=O)(CP(=O)(O)[O-])[O-])O)O[C@H]([C@@H]1O)n1cnc2c1ncnc2N.[Na+].[Na+]
• InChI: InChI=1S/C11H18N5O12P3.2Na/c12-9-6-10(14-2-13-9)16(3-15-6)11-8(18)7(17)5(27-11)1-26-31(24,25)28-30(22,23)4-29(19,20)21;;/h2-3,5,7-8,11,17-18H,1,4H2,(H,22,23)(H,24,25)(H2,12,13,14)(H2,19,20,21);;/q;2*+1/p-2/t5-,7-,8-,11-;;/m1../s1
• InChIKey: KZCUOVRMGTZINH-LYYWGVPGSA-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]methoxy}(hydroxy)phosphoryl (hydrogen phosphonatomethyl)phosphonate
• IUPAC Traditional name: disodium [(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy(hydroxy)phosphoryl hydrogen phosphonatomethylphosphonate
• Synonyms: AMP-PCP disodium salt; Adenylylmethylenediphosphonate disodium salt; β,γ-Methyleneadenosine 5′-triphosphate disodium salt

Database IDs

• CAS Number: 7414-56-4
• PubChem SID: 24897166; 162227174
• PubChem CID: 71308607

CALCULATED PROPERTIES

• Acid pKa: 1.3762317
• H Acceptors: 14
• H Donor: 5
• LogD (pH = 5.5): -10.361671
• LogD (pH = 7.4): -10.709088
• Log P: -6.604389
• Molar Refractivity: 95.9246 cm^3
• Polarizability: 39.389294 Å^3
• Polar Surface Area: 275.56 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: H2O: soluble10 mg/mL
• Apperance: white solid

Safety Information

• European Hazard Symbols: Toxic (T)
• German water hazard class: 3
• Risk Statements: 23/24/25-36/37/38
• Safety Statements: 22-26-36-45
• GHS Pictograms: GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H301-H311-H315-H319-H331-H335
• GHS Precautionary statements: P261-P280-P301 + P310-P305 + P351 + P338-P311
• Personal Protective Equipment: Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
• Storage Temperature: -20°C

Product Information

• Purity: ≥95%

DETAILS

Sigma Aldrich - M7510

Physical form
hygroscopic solid
Biochem/physiol Actions
Selective P2X purinoceptor agonist that is more potent than ATP, but less potent than α, β-methylene-L-adenosine 5′-triphosphate.