(2S,5R)-7-oxo-2-((R)-pyrrolidin-3-ylcarbamoyl)-1,6-diazabicyclo[3.2.1]octan-6-yl hydrogen sulfate

ID: ALA3112743

PubChem CID: 44183769

Max Phase: Preclinical

Molecular Formula: C11H18N4O6S

Molecular Weight: 334.35

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(N[C@@H]1CCNC1)[C@@H]1CC[C@@H]2CN1C(=O)N2OS(=O)(=O)O

Standard InChI:  InChI=1S/C11H18N4O6S/c16-10(13-7-3-4-12-5-7)9-2-1-8-6-14(9)11(17)15(8)21-22(18,19)20/h7-9,12H,1-6H2,(H,13,16)(H,18,19,20)/t7-,8-,9+/m1/s1

Standard InChI Key:  DGAUUFHQTQVNOS-HLTSFMKQSA-N

Molfile:  

     RDKit          2D

 22 24  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
    2.6935    5.8365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9692    6.6256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1139    5.6563    0.0000 N   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
  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  6
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 18  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3112743

   [(2S,5R)-7-oxo-2-[[(3R)-pyrrolidin-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: 334.35

Molecular Weight (Monoisotopic): 334.0947

AlogP: -1.53

#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: -2.01

CX Basic pKa: 10.40

CX LogP: -3.17

CX LogD: -3.17

Aromatic Rings: ┄

Heavy Atoms: 22

QED Weighted: 0.53

Np Likeness Score: -0.48

References

1. Blizzard TA, Chen H, Kim S, Wu J, Bodner R, Gude C, Imbriglio J, Young K, Park YW, Ogawa A, Raghoobar S, Hairston N, Painter RE, Wisniewski D, Scapin G, Fitzgerald P, Sharma N, Lu J, Ha S, Hermes J, Hammond ML..  (2014)  Discovery of MK-7655, a β-lactamase inhibitor for combination with Primaxin®.,  24  (3): [PMID:24433862] [10.1016/j.bmcl.2013.12.101]

2.  (2013)  Œ=-lactamase inhibitors, 

Source

Source(2):

• Scientific Literature
• BindingDB Database