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

ID: ALA423306

PubChem CID: 44310211

Max Phase: Preclinical

Molecular Formula: C12H17N2NaO6S

Molecular Weight: 318.35

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C12H18N2O6S.Na/c1-12(2,3)8-7(11(16)17)14-9(15)6(10(14)20-8)5-13-21(4,18)19;/h6,10,13H,5H2,1-4H3,(H,16,17);/q;+1/p-1/t6-,10+;/m0./s1

Standard InChI Key:  IZXJLFBUCUQHFY-FXWROEHUSA-M

Molfile:  

     RDKit          2D

 23 23  0  0  0  0  0  0  0  0999 V2000
    4.7417   -8.5542    0.0000 Na  0  0  0  0  0 15  0  0  0  0  0  0
    5.7917   -7.0292    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.5917   -7.2792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7917   -6.2042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9667   -7.0292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0667   -6.6167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9667   -6.2042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5792   -5.9417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0167   -4.2417    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    6.8417   -8.0667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3917   -5.6167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8917   -6.6042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6042   -4.8292    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3917   -7.6167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7292   -3.8292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3042   -4.6542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3292   -8.8625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6542   -8.2292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4292   -3.6667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9667   -5.7542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6667   -6.6917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2667   -7.3667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6315   -5.2171    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 10  1  0
 18 10  2  0
 19  9  1  0
 20 12  1  0
 21 12  1  0
 22 12  1  0
  4  7  1  0
  6  8  1  0
  4 23  1  6
M  CHG  2   1   1  17  -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: 318.35

Molecular Weight (Monoisotopic): 318.0886

AlogP: -0.31

#Rotatable Bonds: 4

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: 3.75

CX Basic pKa: ┄

CX LogP: -1.16

CX LogD: -4.44

Aromatic Rings: ┄

Heavy Atoms: 21

QED Weighted: 0.69

Np Likeness Score: -0.08

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