(2S,3S,4S,5R,6R)-6-{[1-azido-3-(9H-carbazol-4-yloxy)propan-2-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid

• ChemBase ID: 161039
• Molecular Formular: C21H22N4O8
• Molecular Mass: 458.42138
• Monoisotopic Mass: 458.14376368
• SMILES: C(C(COc1cccc2c1c1c([nH]2)cccc1)O[C@H]1[C@H]([C@H]([C@@H]([C@@H](O1)C(=O)O)O)O)O)N=[N+]=[N-]
• Canonical SMILES: [N-]=[N+]=NCC(O[C@@H]1O[C@@H](C(=O)O)[C@H]([C@@H]([C@@H]1O)O)O)COc1cccc2c1c1ccccc1[nH]2
• InChI: InChI=1S/C21H22N4O8/c22-25-23-8-10(32-21-18(28)16(26)17(27)19(33-21)20(29)30)9-31-14-7-3-6-13-15(14)11-4-1-2-5-12(11)24-13/h1-7,10,16-19,21,24,26-28H,8-9H2,(H,29,30)/t10?,16-,17-,18+,19-,21+/m0/s1
• InChIKey: YQBUSJUVRBZOFQ-UHSUVFMESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5R,6R)-6-{[1-azido-3-(9H-carbazol-4-yloxy)propan-2-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
• IUPAC Traditional name: (2S,3S,4S,5R,6R)-6-{[1-azido-3-(9H-carbazol-4-yloxy)propan-2-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
• Synonyms: 2-(9H-Carbazol-4-yloxy)-1-[azidomethyl]ethyl β-D-Glucopyranosiduronic Acid; 4-[1'-(3'-Azido-1',2'-propanediol)]carbazole 2'-O-β-D-Glucuronide

Database IDs

• PubChem SID: 162255174
• PubChem CID: 71313593

CALCULATED PROPERTIES

• Acid pKa: 3.1360288
• H Acceptors: 10
• H Donor: 5
• LogD (pH = 5.5): -1.4686322
• LogD (pH = 7.4): -2.5875254
• Log P: 0.9825608
• Molar Refractivity: 110.7634 cm^3
• Polarizability: 45.64085 Å^3
• Polar Surface Area: 170.9 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Methanol
• Apperance: Brown Solid

DETAILS

Toronto Research Chemicals - A856300

Intermediate in the preparation of Carvedilol metabolites.