(2S,3S,5R)-3-((Z)-2-Carbamoyl-vinyl)-3-methyl-4,4,7-trioxo-4lambda*6*-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid

ID: ALA124961

PubChem CID: 10755764

Max Phase: Preclinical

Molecular Formula: C10H12N2O6S

Molecular Weight: 288.28

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C[C@]1(/C=C\C(N)=O)[C@H](C(=O)O)N2C(=O)C[C@H]2S1(=O)=O

Standard InChI:  InChI=1S/C10H12N2O6S/c1-10(3-2-5(11)13)8(9(15)16)12-6(14)4-7(12)19(10,17)18/h2-3,7-8H,4H2,1H3,(H2,11,13)(H,15,16)/b3-2-/t7-,8+,10+/m1/s1

Standard InChI Key:  JISMAMQZHUQTJZ-BJTZKDDDSA-N

Molfile:  

     RDKit          2D

 20 21  0  0  1  0  0  0  0  0999 V2000
   -1.7125    0.4583    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2875    0.0333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2958   -0.3000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2875    0.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7125   -0.4542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8958   -0.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8875    0.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8625   -0.3917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4125   -0.9750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0125    0.9833    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4125    0.9833    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2625   -0.3917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0375    0.1333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3208   -0.7250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7208   -1.4917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2625    0.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8625    0.4583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6375    0.1333    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8125   -0.9750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4208    0.9250    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  4  1  0
  4  1  1  0
  5  2  1  0
  6  7  1  0
  7  4  1  0
  2  8  1  0
  5  9  1  6
 10  1  2  0
 11  1  2  0
 12  8  2  0
 13 12  1  0
 14  6  2  0
 15  9  2  0
 16 13  2  0
  2 17  1  6
 18 13  1  0
 19  9  1  0
  4 20  1  6
  3  5  1  0
  6  3  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA124961

   (2S,3S,5R)-3-((Z)-2-Carbamoyl-vinyl)-3-methyl-4,4,7-trioxo-4lambda*6*-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid

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: 288.28

Molecular Weight (Monoisotopic): 288.0416

AlogP: -1.77

#Rotatable Bonds: 3

Polar Surface Area: 134.84

Molecular Species: ACID

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.12

CX Basic pKa: ┄

CX LogP: -1.90

CX LogD: -5.36

Aromatic Rings: ┄

Heavy Atoms: 19

QED Weighted: 0.47

Np Likeness Score: 0.66

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