(2S,3S,5R)-3-Methyl-4,4,7-trioxo-3-((Z)-3-oxo-but-1-enyl)-4lambda*6*-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid

ID: ALA124960

PubChem CID: 44347961

Max Phase: Preclinical

Molecular Formula: C11H13NO6S

Molecular Weight: 287.29

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C11H13NO6S/c1-6(13)3-4-11(2)9(10(15)16)12-7(14)5-8(12)19(11,17)18/h3-4,8-9H,5H2,1-2H3,(H,15,16)/b4-3-/t8-,9+,11+/m1/s1

Standard InChI Key:  YXTACWPFRBTXGO-VPDCVBLDSA-N

Molfile:  

     RDKit          2D

 20 21  0  0  1  0  0  0  0  0999 V2000
    1.4125   -0.4792    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.8375   -0.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8292   -1.2292    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8375   -0.6292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4125   -1.3875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2292   -1.2292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2375   -0.6292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2542   -1.3250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7125   -1.9042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1125    0.0458    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7125    0.0458    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8625   -1.3250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1958   -1.6542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4042   -2.4250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2542   -0.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1625   -0.8042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8625   -0.2792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3125   -1.9042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7625   -0.8042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8292   -0.0292    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  6  2  0
 14  9  2  0
  2 15  1  6
 16 12  1  0
 17 16  2  0
 18  9  1  0
 19 16  1  0
  4 20  1  6
  3  5  1  0
  6  3  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA124960

   (2S,3S,5R)-3-Methyl-4,4,7-trioxo-3-((Z)-3-oxo-but-1-enyl)-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: 287.29

Molecular Weight (Monoisotopic): 287.0464

AlogP: -0.67

#Rotatable Bonds: 3

Polar Surface Area: 108.82

Molecular Species: ACID

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.17

CX Basic pKa: ┄

CX LogP: -0.76

CX LogD: -4.21

Aromatic Rings: ┄

Heavy Atoms: 19

QED Weighted: 0.54

Np Likeness Score: 1.00

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