US8487093, 196

ID: ALA3963657

PubChem CID: 44183039

Max Phase: Preclinical

Molecular Formula: C16H22N6O6S

Molecular Weight: 426.46

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(Nc1ccc(N2CCNCC2)cn1)[C@@H]1CC[C@@H]2CN1C(=O)N2OS(=O)(=O)O

Standard InChI:  InChI=1S/C16H22N6O6S/c23-15(19-14-4-2-11(9-18-14)20-7-5-17-6-8-20)13-3-1-12-10-21(13)16(24)22(12)28-29(25,26)27/h2,4,9,12-13,17H,1,3,5-8,10H2,(H,18,19,23)(H,25,26,27)/t12-,13+/m1/s1

Standard InChI Key:  RWGXEOGYQQYGHG-OLZOCXBDSA-N

Molfile:  

     RDKit          2D

 29 32  0  0  1  0  0  0  0  0999 V2000
   -1.5290   -4.1726    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6608   -3.7738    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5718   -4.5549    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4400   -4.9533    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9361   -2.2985    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8063   -1.3319    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8393    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9488    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8975   -0.8028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6421    0.6933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.6568    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0947    1.4779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6568   -0.6386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2223   -1.4554    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6055    1.8369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7867    1.6253    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0965    3.2488    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0640    4.3961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5574    5.8080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5267    6.9527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0027    6.6857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5094    5.2739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5401    4.1291    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.9725    7.8310    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.4681    9.2437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4392   10.3869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9148   10.1175    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.4193    8.7049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4482    7.5617    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  1
  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  6
 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  2  0
 23 18  1  0
 21 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 29 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3963657

   [(2S,5R)-7-oxo-2-[(5-piperazin-1-ylpyridin-2-yl)carbamoyl]-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: 426.46

Molecular Weight (Monoisotopic): 426.1322

AlogP: -0.57

#Rotatable Bonds: 5

Polar Surface Area: 144.41

Molecular Species: ZWITTERION

HBA: 8

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 12

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 1

CX Acidic pKa: -2.14

CX Basic pKa: 8.84

CX LogP: -1.80

CX LogD: -1.81

Aromatic Rings: 1

Heavy Atoms: 29

QED Weighted: 0.53

Np Likeness Score: -1.13

References

1.  (2013)  Œ=-lactamase inhibitors, 

Source

Source(1):

• BindingDB Database