{[(4aR,6R,7R,7aS)-6-{4-amino-1H-imidazo[4,5-c]pyridin-1-yl}-7-hydroxy-2-oxo-hexahydro-1,3,5,2λ5-furo[3,2-d][1,3,2λ5]dioxaphosphinin-2-yl]oxy}({[(2S,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy})phosphinic acid

• ChemBase ID: 156068
• Molecular Formular: C16H22N4O13P2
• Molecular Mass: 540.312402
• Monoisotopic Mass: 540.06586004
• SMILES: c1cnc(c2c1n(cn2)[C@H]1[C@@H]([C@H]2[C@H](O1)COP(=O)(O2)OP(=O)(O)O[C@H]1[C@@H]([C@@H]([C@H](O1)CO)O)O)O)N
• Canonical SMILES: OC[C@H]1O[C@H]([C@@H]([C@@H]1O)O)OP(=O)(OP1(=O)OC[C@@H]2[C@@H](O1)[C@@H](O)[C@@H](O2)n1cnc2c1ccnc2N)O
• InChI: InChI=1S/C16H22N4O13P2/c17-14-9-6(1-2-18-14)20(5-19-9)15-12(24)13-8(29-15)4-28-35(27,31-13)33-34(25,26)32-16-11(23)10(22)7(3-21)30-16/h1-2,5,7-8,10-13,15-16,21-24H,3-4H2,(H2,17,18)(H,25,26)/t7-,8-,10-,11-,12-,13-,15-,16+,35?/m1/s1
• InChIKey: OQRDOVWETUSZCW-NDRVCTFCSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: {[(4aR,6R,7R,7aS)-6-{4-amino-1H-imidazo[4,5-c]pyridin-1-yl}-7-hydroxy-2-oxo-hexahydro-1,3,5,2λ^5-furo[3,2-d][1,3,2λ^5]dioxaphosphinin-2-yl]oxy}({[(2S,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy})phosphinic acid
• IUPAC Traditional name: [(4aR,6R,7R,7aS)-6-{4-aminoimidazo[4,5-c]pyridin-1-yl}-7-hydroxy-2-oxo-tetrahydro-4H-1,3,5,2λ^5-furo[3,2-d][1,3,2λ^5]dioxaphosphinin-2-yl]oxy[(2S,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxyphosphinic acid
• Synonyms: 3-Deaza-cADP-ribose; 3-Deaza-cyclic adenosine 5′-diphosphate ribose; Cyclic 3-deaza-adenosine diphosphate-ribose

Database IDs

• MDL Number: MFCD03427796
• PubChem SID: 162250206
• PubChem CID: 71312267

CALCULATED PROPERTIES

• Acid pKa: -0.09011466
• H Acceptors: 12
• H Donor: 6
• LogD (pH = 5.5): -5.1748395
• LogD (pH = 7.4): -5.183376
• Log P: -4.9221673
• Molar Refractivity: 108.5705 cm^3
• Polarizability: 45.491837 Å^3
• Polar Surface Area: 247.4 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: H2O: freely soluble
• Apperance: light yellow oil

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% (HPLC)
• Shipped in: wet ice
• Empirical Formula (Hill Notation): C16H22N4O13P2

DETAILS

Sigma Aldrich - D7939

Biochem/physiol Actions
Heat and hydrolysis resistant cyclic ADP ribose agonist.
Legal Information
US Patent No. 6,593,307