Sodium salt (2S,3S,5R)-3-methyl-3-((E)-2-[1,3,4]oxadiazol-2-yl-vinyl)-4,4,7-trioxo-4lambda*6*-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylate

ID: ALA123702

PubChem CID: 44347744

Max Phase: Preclinical

Molecular Formula: C11H10N3NaO6S

Molecular Weight: 313.29

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C[C@]1(/C=C/c2nnco2)[C@H](C(=O)[O-])N2C(=O)C[C@H]2S1(=O)=O.[Na+]

Standard InChI:  InChI=1S/C11H11N3O6S.Na/c1-11(3-2-6-13-12-5-20-6)9(10(16)17)14-7(15)4-8(14)21(11,18)19;/h2-3,5,8-9H,4H2,1H3,(H,16,17);/q;+1/p-1/b3-2+;/t8-,9+,11+;/m1./s1

Standard InChI Key:  WXCAVYPVBXYTTO-UCMHIHBJSA-M

Molfile:  

     RDKit          2D

 23 24  0  0  0  0  0  0  0  0999 V2000
    2.9917   -5.7167    0.0000 Na  0  0  0  0  0 15  0  0  0  0  0  0
    4.5792   -2.7542    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.1667   -3.3292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7917   -3.7917    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7917   -2.9667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5792   -4.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9667   -3.7917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9667   -2.9667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7500   -3.9125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9917   -4.7167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6500   -5.3792    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.2667   -5.9292    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.9875   -4.6250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9917   -2.0292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2750   -1.9042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8042   -4.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5750   -3.9125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9792   -5.5167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3792   -4.3792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8167   -4.7167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5792   -5.4250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7500   -2.7417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7917   -2.1417    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  1  0
  4  5  1  0
  5  2  1  0
  6  3  1  0
  7  8  1  0
  8  5  1  0
  3  9  1  0
  6 10  1  6
 11 13  2  0
 12 11  1  0
 13 17  1  0
 14  2  2  0
 15  2  2  0
 16 13  1  0
 17  9  2  0
 18 16  1  0
 19  7  2  0
 20 10  1  0
 21 10  2  0
  3 22  1  6
  5 23  1  6
  4  6  1  0
  4  7  1  0
 12 18  2  0
M  CHG  2   1   1  20  -1
M  END

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: 313.29

Molecular Weight (Monoisotopic): 313.0369

AlogP: -0.72

#Rotatable Bonds: 3

Polar Surface Area: 130.67

Molecular Species: ACID

HBA: 7

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.22

CX Basic pKa: ┄

CX LogP: -1.71

CX LogD: -5.15

Aromatic Rings: 1

Heavy Atoms: 21

QED Weighted: 0.72

Np Likeness Score: 0.06

References

1. Richter HG, Angehrn P, Hubschwerlen C, Kania M, Page MG, Specklin JL, Winkler FK..  (1996)  Design, synthesis, and evaluation of 2 beta-alkenyl penam sulfone acids as inhibitors of beta-lactamases.,  39  (19): [PMID:8809160] [10.1021/jm9601967]

Source

Source(1):

• Scientific Literature