US8487093, 104

ID: ALA3959010

PubChem CID: 44184420

Max Phase: Preclinical

Molecular Formula: C16H25N5O7S

Molecular Weight: 431.47

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(N[C@@H]1CCN(C2CCNCC2)C1=O)[C@@H]1CC[C@@H]2CN1C(=O)N2OS(=O)(=O)O

Standard InChI:  InChI=1S/C16H25N5O7S/c22-14(18-12-5-8-19(15(12)23)10-3-6-17-7-4-10)13-2-1-11-9-20(13)16(24)21(11)28-29(25,26)27/h10-13,17H,1-9H2,(H,18,22)(H,25,26,27)/t11-,12-,13+/m1/s1

Standard InChI Key:  WSTRNZBLNKKHSG-UPJWGTAASA-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
    4.5458    4.2681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1139    5.6563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9692    6.6256    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0806    8.1223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3750    8.8703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3734   10.3703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0736   11.1190    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7754   10.3677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7769    8.8677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6935    5.8365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5803    6.2844    0.0000 O   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
 18 17  1  1
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 22  1  0
 21 28  1  0
 28 18  1  0
 28 29  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA3959010

   [(2S,5R)-7-oxo-2-[[(3R)-2-oxo-1-piperidin-4-ylpyrrolidin-3-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: 431.47

Molecular Weight (Monoisotopic): 431.1475

AlogP: -1.54

#Rotatable Bonds: 5

Polar Surface Area: 148.59

Molecular Species: ZWITTERION

HBA: 7

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 12

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 1

CX Acidic pKa: -1.97

CX Basic pKa: 10.02

CX LogP: -3.89

CX LogD: -3.90

Aromatic Rings: ┄

Heavy Atoms: 29

QED Weighted: 0.44

Np Likeness Score: -0.39

References

1.  (2013)  Œ=-lactamase inhibitors, 

Source

Source(1):

• BindingDB Database