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

• ChemBase ID: 160441
• Molecular Formular: C21H24N2O8
• Molecular Mass: 432.42386
• Monoisotopic Mass: 432.15326574
• SMILES: NCC(COc1cccc2c1c1c([nH]2)cccc1)O[C@H]1[C@H]([C@H]([C@@H]([C@@H](O1)C(=O)O)O)O)O
• Canonical SMILES: 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/C21H24N2O8/c22-8-10(30-21-18(26)16(24)17(25)19(31-21)20(27)28)9-29-14-7-3-6-13-15(14)11-4-1-2-5-12(11)23-13/h1-7,10,16-19,21,23-26H,8-9,22H2,(H,27,28)/t10?,16-,17-,18+,19-,21+/m0/s1
• InChIKey: POYNTLLXNSEZCA-UHSUVFMESA-N

NAMES AND DATABASE IDS

Names

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

Database IDs

• PubChem SID: 162254576
• PubChem CID: 71313344

CALCULATED PROPERTIES

• Acid pKa: 3.0740678
• H Acceptors: 9
• H Donor: 6
• LogD (pH = 5.5): -2.208622
• LogD (pH = 7.4): -2.2135613
• Log P: -2.207874
• Molar Refractivity: 106.1284 cm^3
• Polarizability: 44.85685 Å^3
• Polar Surface Area: 167.49 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Methanol
• Apperance: Yellow Solid

DETAILS

Toronto Research Chemicals - A628095

Intermediate in the preparation of Carvedilol metabolites.