{[(Z)-(2-phenyl-1-{[(1R,2R,3S,4R,5R)-2,3,4-trihydroxy-5-(hydroxymethyl)cyclohexyl]sulfanyl}ethylidene)amino]oxy}sulfonic acid

• ChemBase ID: 4219
• Molecular Formular: C15H21NO8S2
• Molecular Mass: 407.45914
• Monoisotopic Mass: 407.07085864
• SMILES: OC[C@H]1C[C@@H](S/C(=N\OS(=O)(=O)O)/Cc2ccccc2)[C@H](O)[C@@H](O)[C@@H]1O
• Canonical SMILES: OC[C@H]1C[C@@H](S/C(=N\OS(=O)(=O)O)/Cc2ccccc2)[C@@H]([C@H]([C@@H]1O)O)O
• InChI: InChI=1S/C15H21NO8S2/c17-8-10-7-11(14(19)15(20)13(10)18)25-12(16-24-26(21,22)23)6-9-4-2-1-3-5-9/h1-5,10-11,13-15,17-20H,6-8H2,(H,21,22,23)/b16-12-/t10-,11-,13-,14+,15+/m1/s1
• InChIKey: LZDZCEOFJWRJIA-GGASBGQWSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: {[(Z)-(2-phenyl-1-{[(1R,2R,3S,4R,5R)-2,3,4-trihydroxy-5-(hydroxymethyl)cyclohexyl]sulfanyl}ethylidene)amino]oxy}sulfonic acid
• IUPAC Traditional name: [(Z)-(2-phenyl-1-{[(1R,2R,3S,4R,5R)-2,3,4-trihydroxy-5-(hydroxymethyl)cyclohexyl]sulfanyl}ethylidene)amino]oxysulfonic acid
• Synonyms: (1S,2S,3R,4S,5S)-2,3,4-TRIHYDROXY-5-(HYDROXYMETHYL)CYCLOHEXYL (1E)-2-PHENYL-N-(SULFOOXY)ETHANIMIDOTHIOATE

Database IDs

• PubChem SID: 160967651; 46507070
• PubChem CID: 9600408

CALCULATED PROPERTIES

JChem

• Acid pKa: -3.4175625
• H Acceptors: 8
• H Donor: 5
• LogD (pH = 5.5): -2.8397288
• LogD (pH = 7.4): -2.839748
• Log P: -1.9876566
• Molar Refractivity: 93.8195 cm^3
• Polarizability: 38.007442 Å^3
• Polar Surface Area: 156.88 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: -1.02
• LOG S: -2.33
• Solubility (Water): 1.90e+00 g/l

DETAILS

DrugBank - DB04659

Drug information: experimental