{[(2R,3S,5R)-5-(6-amino-9H-purin-9-yl)-2-methyloxolan-3-yl]oxy}phosphonic acid

• ChemBase ID: 4499
• Molecular Formular: C10H14N5O5P
• Molecular Mass: 315.222421
• Monoisotopic Mass: 315.0732552
• SMILES: P(=O)(O)(O)O[C@@H]1[C@@H](C)O[C@H](C1)n1cnc2c(N)ncnc12
• Canonical SMILES: C[C@H]1O[C@H](C[C@@H]1OP(=O)(O)O)n1cnc2c1ncnc2N
• InChI: InChI=1S/C10H14N5O5P/c1-5-6(20-21(16,17)18)2-7(19-5)15-4-14-8-9(11)12-3-13-10(8)15/h3-7H,2H2,1H3,(H2,11,12,13)(H2,16,17,18)/t5-,6+,7-/m1/s1
• InChIKey: NFGZMOICZSFFLB-DSYKOEDSSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: {[(2R,3S,5R)-5-(6-amino-9H-purin-9-yl)-2-methyloxolan-3-yl]oxy}phosphonic acid
• IUPAC Traditional name: [(2R,3S,5R)-5-(6-aminopurin-9-yl)-2-methyloxolan-3-yl]oxyphosphonic acid
• Synonyms: 2',5'-DIDEOXY-ADENOSINE 3'-MONOPHOSPHATE; 2′,5′-Dideoxy-3′-AMP; 2′,5′-dd-3′-AMP; 2′,5′-Dideoxyadenosine 3′-monophosphate

Database IDs

• CAS Number: 121878-11-3
• MDL Number: MFCD03095619
• PubChem SID: 160967931; 99443314; 24893287
• PubChem CID: 444894

CALCULATED PROPERTIES

JChem

• Acid pKa: 1.1620734
• H Acceptors: 8
• H Donor: 3
• LogD (pH = 5.5): -2.8164861
• LogD (pH = 7.4): -3.851142
• Log P: -3.264551
• Molar Refractivity: 71.0141 cm^3
• Polarizability: 27.667725 Å^3
• Polar Surface Area: 145.61 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: -1.78
• LOG S: -2.13
• Solubility (Water): 2.35e+00 g/l

PROPERTIES

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

DETAILS

DrugBank - DB06843

Drug information: experimental

Sigma Aldrich - D0689

Biochem/physiol Actions
Potent inhibitor of adenylyl cyclase. Not cell-permeable. Precursor to 2′,5′-Dideoxyadenosine 3′-triphosphate (Prod. No. D0939). IC50 = 460 nM in detergent-dispersed rat brain preparation.