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

ID: ALA123029

Cas Number: 180323-79-9

PubChem CID: 10639238

Max Phase: Preclinical

Molecular Formula: C11H14N2O7S

Molecular Weight: 318.31

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C11H14N2O7S/c1-11(3-2-4-20-10(12)17)8(9(15)16)13-6(14)5-7(13)21(11,18)19/h2-3,7-8H,4-5H2,1H3,(H2,12,17)(H,15,16)/b3-2+/t7-,8+,11+/m1/s1

Standard InChI Key:  SSPXJFPHCWPEHF-DXXCBAFQSA-N

Molfile:  

     RDKit          2D

 22 23  0  0  1  0  0  0  0  0999 V2000
    4.5292   -3.2250    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.7417   -4.2375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.1000   -3.7917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7542   -3.4292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5292   -4.4542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9292   -4.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9292   -3.4292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9292   -5.1542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3042   -2.4292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2167   -2.8042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4125   -5.1000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6792   -4.3667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3542   -4.8167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5167   -5.8542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2042   -5.8917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6792   -3.2125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4667   -4.1500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2042   -4.8792    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.7500   -5.1542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8417   -4.5167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0417   -4.7292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7417   -2.6167    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  4  1  0
  3  1  1  0
  4  1  1  0
  5  3  1  0
  6  7  1  0
  7  4  1  0
  5  8  1  6
  9  1  2  0
 10  1  2  0
 11 20  1  0
  3 12  1  0
 13  6  2  0
 14  8  2  0
 15 11  2  0
  3 16  1  6
 17 12  2  0
 18 11  1  0
 19  8  1  0
 20 21  1  0
 21 17  1  0
  4 22  1  6
  2  5  1  0
  2  6  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA123029

   (2S,3S,5R)-3-((E)-3-Carbamoyloxy-propenyl)-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: 318.31

Molecular Weight (Monoisotopic): 318.0522

AlogP: -1.16

#Rotatable Bonds: 4

Polar Surface Area: 144.07

Molecular Species: ACID

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.14

CX Basic pKa: ┄

CX LogP: -1.30

CX LogD: -4.76

Aromatic Rings: ┄

Heavy Atoms: 21

QED Weighted: 0.49

Np Likeness Score: 0.80

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