US8487093, 16

ID: ALA3956247

PubChem CID: 71699860

Max Phase: Preclinical

Molecular Formula: C16H20N4O6S

Molecular Weight: 396.43

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(Nc1ccc2c(c1)CCNC2)[C@@H]1CCC2CN1C(=O)N2OS(=O)(=O)O

Standard InChI:  InChI=1S/C16H20N4O6S/c21-15(18-12-2-1-11-8-17-6-5-10(11)7-12)14-4-3-13-9-19(14)16(22)20(13)26-27(23,24)25/h1-2,7,13-14,17H,3-6,8-9H2,(H,18,21)(H,23,24,25)/t13?,14-/m0/s1

Standard InChI Key:  XXIFWUYINSCSPL-KZUDCZAMSA-N

Molfile:  

     RDKit          2D

 27 30  0  0  1  0  0  0  0  0999 V2000
    8.4999   -7.2184    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.4256   -6.4548    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   10.5496   -6.8751    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.6238   -7.6383    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.1770   -4.9747    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7837   -4.4555    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.4177   -3.5373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7387   -4.1520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1238   -5.2320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8933   -3.7570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4038   -3.2090    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.1495   -2.0617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4659   -4.1997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9212   -5.2689    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5951   -3.0039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5548   -3.6021    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5973   -1.5031    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5981    1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8971    0.7500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8971   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5981   -1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  2  0
  2  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12  7  1  0
 11 13  1  0
 13  6  1  0
 13 14  2  0
 10 15  1  1
 15 16  2  0
 15 17  1  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 21  1  0
 26 27  2  0
 27 18  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3956247

   [(2S)-7-oxo-2-(1,2,3,4-tetrahydroisoquinolin-6-ylcarbamoyl)-1,6-diazabicyclo[3.2.1]octan-6-yl] hydrogen sulfate

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 396.43

Molecular Weight (Monoisotopic): 396.1104

AlogP: 0.27

#Rotatable Bonds: 4

Polar Surface Area: 128.28

Molecular Species: ZWITTERION

HBA: 6

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 10

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: -2.06

CX Basic pKa: 8.96

CX LogP: -1.14

CX LogD: -1.15

Aromatic Rings: 1

Heavy Atoms: 27

QED Weighted: 0.62

Np Likeness Score: -0.67

References

1.  (2013)  Œ=-lactamase inhibitors, 

Source

Source(1):

• BindingDB Database