{[(1R,12S,13R,14S,15R,21R,22S,23R)-3-azido-13,14,22,23-tetrahydroxy-18-oxo-17,19,24,25-tetraoxa-2,4,7,9,11-pentaaza-18λ5-phosphapentacyclo[19.2.1.112,15.02,6.05,10]pentacosa-3,5(10),6,8-tetraen-18-yl]oxy}phosphonic acid

• ChemBase ID: 132538
• Molecular Formular: C15H20N8O13P2
• Molecular Mass: 582.312622
• Monoisotopic Mass: 582.062506
• SMILES: c1nc2c3c(n1)n(c(n3)N=[N+]=[N-])[C@H]1[C@@H]([C@@H]([C@H](O1)COP(=O)(OC[C@@H]1[C@H]([C@H]([C@@H](N2)O1)O)O)OP(=O)(O)O)O)O
• Canonical SMILES: [N-]=[N+]=Nc1nc2c3n1[C@@H]1O[C@@H]([C@H]([C@H]1O)O)COP(=O)(OC[C@H]1O[C@H](Nc2ncn3)[C@H](O)[C@@H]1O)OP(=O)(O)O
• InChI: InChI=1S/C15H20N8O13P2/c16-22-21-15-19-6-11-17-3-18-12(6)23(15)14-10(27)8(25)5(35-14)2-33-38(31,36-37(28,29)30)32-1-4-7(24)9(26)13(20-11)34-4/h3-5,7-10,13-14,24-27H,1-2H2,(H,17,18,20)(H2,28,29,30)/t4-,5-,7-,8-,9-,10-,13+,14-,38?/m1/s1
• InChIKey: VZJBHZHVGJAQMW-IDRSVVGJSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: {[(1R,12S,13R,14S,15R,21R,22S,23R)-3-azido-13,14,22,23-tetrahydroxy-18-oxo-17,19,24,25-tetraoxa-2,4,7,9,11-pentaaza-18λ^5-phosphapentacyclo[19.2.1.1^1^2,^1^5.0^2,^6.0^5,^1^0]pentacosa-3,5(10),6,8-tetraen-18-yl]oxy}phosphonic acid
• IUPAC Traditional name: [(1R,12S,13R,14S,15R,21R,22S,23R)-3-azido-13,14,22,23-tetrahydroxy-18-oxo-17,19,24,25-tetraoxa-2,4,7,9,11-pentaaza-18λ^5-phosphapentacyclo[19.2.1.1^1^2,^1^5.0^2,^6.0^5,^1^0]pentacosa-3,5(10),6,8-tetraen-18-yl]oxyphosphonic acid
• Synonyms: Cyclic adenosine diphosphate-ribose 8-azide; 8-Azido-cyclic adenosine diphosphate-ribose

Database IDs

• CAS Number: 150424-94-5
• MDL Number: MFCD01310493
• PubChem SID: 162226815; 24891143
• PubChem CID: 17749230

CALCULATED PROPERTIES

• Acid pKa: -1.4083995
• H Acceptors: 16
• H Donor: 7
• LogD (pH = 5.5): -6.3914585
• LogD (pH = 7.4): -6.968119
• Log P: -5.2061133
• Molar Refractivity: 118.1163 cm^3
• Polarizability: 46.322395 Å^3
• Polar Surface Area: 286.73 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Apperance: lyophilized powder

Safety Information

• German water hazard class: 3
• Storage Temperature: -20°C

Product Information

• Purity: ≥95% (HPLC)

DETAILS

Sigma Aldrich - A6830

Application
Photoaffinity label
Linkage
Analog of cyclic ADP-ribose
Physical form
Lyophilized powder containing approx. 50% sodium chloride.