2-{[(2R,4S,5S)-4-{[(2R,3S,4S,5R,6R)-3-acetamido-4-hydroxy-6-(hydroxymethyl)-5-(sulfooxy)oxan-2-yl]oxy}-5-(hydroxymethyl)pyrrolidin-2-yl]formamido}ethane-1-sulfonic acid

• ChemBase ID: 2323
• Molecular Formular: C16H29N3O14S2
• Molecular Mass: 551.54316
• Monoisotopic Mass: 551.10909462
• SMILES: CC(=O)N[C@H]1[C@H](O)[C@@H](OS(=O)(=O)O)[C@@H](CO)O[C@H]1O[C@H]1C[C@@H](N[C@H]1CO)C(=O)NCCS(=O)(=O)O
• Canonical SMILES: OC[C@@H]1N[C@H](C[C@@H]1O[C@@H]1O[C@H](CO)[C@@H]([C@H]([C@@H]1NC(=O)C)O)OS(=O)(=O)O)C(=O)NCCS(=O)(=O)O
• InChI: InChI=1S/C16H29N3O14S2/c1-7(22)18-12-13(23)14(33-35(28,29)30)11(6-21)32-16(12)31-10-4-8(19-9(10)5-20)15(24)17-2-3-34(25,26)27/h8-14,16,19-21,23H,2-6H2,1H3,(H,17,24)(H,18,22)(H,25,26,27)(H,28,29,30)/t8-,9+,10+,11-,12+,13+,14+,16-/m1/s1
• InChIKey: RPNZWZDLNYCCIG-RWQOYFMZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-{[(2R,4S,5S)-4-{[(2R,3S,4S,5R,6R)-3-acetamido-4-hydroxy-6-(hydroxymethyl)-5-(sulfooxy)oxan-2-yl]oxy}-5-(hydroxymethyl)pyrrolidin-2-yl]formamido}ethane-1-sulfonic acid
• IUPAC Traditional name: 2-{[(2R,4S,5S)-4-{[(2R,3S,4S,5R,6R)-3-acetamido-4-hydroxy-6-(hydroxymethyl)-5-(sulfooxy)oxan-2-yl]oxy}-5-(hydroxymethyl)pyrrolidin-2-yl]formamido}ethanesulfonic acid
• Synonyms: Bulgecin A

Database IDs

• CAS Number: 92953-54-3
• PubChem SID: 160965775; 46507352
• PubChem CID: 46936433; 46936434

CALCULATED PROPERTIES

JChem

• Acid pKa: -1.8683052
• H Acceptors: 14
• H Donor: 8
• LogD (pH = 5.5): -9.03717
• LogD (pH = 7.4): -9.063531
• Log P: -7.6956887
• Molar Refractivity: 110.2563 cm^3
• Polarizability: 46.670795 Å^3
• Polar Surface Area: 267.35 Å^2
• Rotatable Bonds: 11
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: -1.26
• LOG S: -2.02
• Solubility (Water): 5.61e+00 g/l

DETAILS

DrugBank - DB02595

Drug information: experimental