Sodium salt (5R,6R)-3-tert-butyl-7-oxo-6-(phenylmethanesulfonylamino-methyl)-4-oxa-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylate

ID: ALA305428

PubChem CID: 44310328

Max Phase: Preclinical

Molecular Formula: C18H21N2NaO6S

Molecular Weight: 394.45

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)(C)C1=C(C(=O)[O-])N2C(=O)[C@H](CNS(=O)(=O)Cc3ccccc3)[C@H]2O1.[Na+]

Standard InChI:  InChI=1S/C18H22N2O6S.Na/c1-18(2,3)14-13(17(22)23)20-15(21)12(16(20)26-14)9-19-27(24,25)10-11-7-5-4-6-8-11;/h4-8,12,16,19H,9-10H2,1-3H3,(H,22,23);/q;+1/p-1/t12-,16+;/m0./s1

Standard InChI Key:  BDUBHKVXYWKPAP-CVHDTDHSSA-M

Molfile:  

     RDKit          2D

 29 30  0  0  0  0  0  0  0  0999 V2000
    4.8667   -9.7500    0.0000 Na  0  0  0  0  0 15  0  0  0  0  0  0
    5.9167   -8.2292    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.7042   -8.4792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9167   -7.4042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0917   -8.2292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1917   -7.8125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0917   -7.4042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6917   -7.1417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1417   -5.4417    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    6.9667   -9.2667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5042   -6.8167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0042   -7.8042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7167   -6.0250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5042   -8.8167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8417   -5.0250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4167   -5.8500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5542   -4.8625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3542  -10.0417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7667   -9.4292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7542   -4.0667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7792   -7.8917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3792   -8.5625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0792   -6.9542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5542   -3.8500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1667   -3.4917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3792   -2.6917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7667   -3.0500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1792   -2.4667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7541   -6.4175    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  1  0
  4  2  1  0
  5  2  1  0
  6  3  2  0
  7  5  1  0
  4  8  1  0
  9 13  1  0
 10  3  1  0
  7 11  1  6
 12  6  1  0
 13 11  1  0
 14  5  2  0
 15  9  2  0
 16  9  2  0
 17  9  1  0
 18 10  1  0
 19 10  2  0
 20 17  1  0
 21 12  1  0
 22 12  1  0
 23 12  1  0
 24 20  2  0
 25 20  1  0
 26 25  2  0
 27 24  1  0
 28 27  2  0
  4  7  1  0
  6  8  1  0
 26 28  1  0
  4 29  1  6
M  CHG  2   1   1  18  -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: 394.45

Molecular Weight (Monoisotopic): 394.1199

AlogP: 1.26

#Rotatable Bonds: 6

Polar Surface Area: 113.01

Molecular Species: ACID

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.69

CX Basic pKa: ┄

CX LogP: 0.72

CX LogD: -2.59

Aromatic Rings: 1

Heavy Atoms: 27

QED Weighted: 0.70

Np Likeness Score: -0.39

References

1. Wild H, Metzger K.  (1993)  Substituted 6-alkyloxapenems: potent -lactamase inhibitors: synthesis and biological characterization,  3  (11): [10.1016/S0960-894X(01)80926-4]

Source

Source(1):

• Scientific Literature