(2R,3S,4R,5R,6E)-3,4,5-trihydroxy-N-[(3R,6R)-6-hydroxy-2-oxoazepan-3-yl]-2-methoxy-8,8-dimethylnon-6-enamide

• ChemBase ID: 3077
• Molecular Formular: C18H32N2O7
• Molecular Mass: 388.45588
• Monoisotopic Mass: 388.22095137
• SMILES: CO[C@H]([C@@H](O)[C@H](O)[C@H](O)/C=C/C(C)(C)C)C(=O)N[C@@H]1CC[C@@H](O)CNC1=O
• Canonical SMILES: CO[C@H]([C@H]([C@@H]([C@@H](/C=C/C(C)(C)C)O)O)O)C(=O)N[C@@H]1CC[C@H](CNC1=O)O
• InChI: InChI=1S/C18H32N2O7/c1-18(2,3)8-7-12(22)13(23)14(24)15(27-4)17(26)20-11-6-5-10(21)9-19-16(11)25/h7-8,10-15,21-24H,5-6,9H2,1-4H3,(H,19,25)(H,20,26)/b8-7+/t10-,11-,12-,13-,14+,15-/m1/s1
• InChIKey: FVBBTOIQETYGOA-JTPZDHBBSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3S,4R,5R,6E)-3,4,5-trihydroxy-N-[(3R,6R)-6-hydroxy-2-oxoazepan-3-yl]-2-methoxy-8,8-dimethylnon-6-enamide
• IUPAC Traditional name: (2R,3S,4R,5R,6E)-3,4,5-trihydroxy-N-[(3R,6R)-6-hydroxy-2-oxoazepan-3-yl]-2-methoxy-8,8-dimethylnon-6-enamide
• Synonyms: (E)-(2r,3r,4s,5r)-3,4,5-Trihydroxy-2-Methoxy-8,8-Dimethyl-Non-6-Enoic Acid ((3s,6r)-6-Hydroxy-2-Oxo-Azepan-3-Yl)-Amide

Database IDs

• PubChem SID: 160966521; 46507692
• PubChem CID: 46936660

CALCULATED PROPERTIES

JChem

• Acid pKa: 12.151632
• H Acceptors: 7
• H Donor: 6
• LogD (pH = 5.5): -1.6281272
• LogD (pH = 7.4): -1.6281341
• Log P: -1.6281271
• Molar Refractivity: 97.962 cm^3
• Polarizability: 38.6366 Å^3
• Polar Surface Area: 148.35 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: -0.69
• LOG S: -1.55
• Solubility (Water): 1.09e+01 g/l

DETAILS

DrugBank - DB03396

Drug information: experimental