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

ID: ALA432534

PubChem CID: 44310270

Max Phase: Preclinical

Molecular Formula: C16H22NNaO7

Molecular Weight: 341.36

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)(C)OC(=O)[C@H](O)[C@H]1C(=O)N2C(C(=O)[O-])=C(C(C)(C)C)O[C@H]12.[Na+]

Standard InChI:  InChI=1S/C16H23NO7.Na/c1-15(2,3)10-8(13(20)21)17-11(19)7(12(17)23-10)9(18)14(22)24-16(4,5)6;/h7,9,12,18H,1-6H3,(H,20,21);/q;+1/p-1/t7-,9+,12+;/m0./s1

Standard InChI Key:  DZJYERSNAGACBN-TTWAZCPVSA-M

Molfile:  

     RDKit          2D

 27 27  0  0  0  0  0  0  0  0999 V2000
    5.6042   -8.1250    0.0000 Na  0  0  0  0  0 15  0  0  0  0  0  0
    6.4417   -6.5750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.2292   -6.8292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4417   -5.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6167   -6.5750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6167   -5.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7042   -6.1542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2167   -5.4917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2292   -5.3792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4792   -7.6125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0292   -5.1667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5292   -6.1542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0167   -6.1792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0292   -7.1625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6417   -4.7917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8542   -8.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2917   -7.7792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2167   -6.3917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2417   -4.3667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6042   -5.3042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3042   -6.2417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9042   -6.9042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0042   -7.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6417   -5.8042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9292   -6.8042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6935   -6.1343    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2815   -4.7629    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  5  1  0
  7  3  2  0
  4  8  1  0
  9 11  1  0
 10  3  1  0
  6 11  1  0
 12  7  1  0
 13  9  1  0
 14  5  2  0
 15  9  2  0
 16 10  1  0
 17 10  2  0
 18 13  1  0
 11 19  1  6
 20 12  1  0
 21 12  1  0
 22 12  1  0
 23 18  1  0
 24 18  1  0
 25 18  1  0
  4  6  1  0
  7  8  1  0
  6 26  1  1
  4 27  1  6
M  CHG  2   1   1  16  -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: 341.36

Molecular Weight (Monoisotopic): 341.1475

AlogP: 0.85

#Rotatable Bonds: 3

Polar Surface Area: 113.37

Molecular Species: ACID

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.65

CX Basic pKa: ┄

CX LogP: 0.52

CX LogD: -2.80

Aromatic Rings: ┄

Heavy Atoms: 24

QED Weighted: 0.58

Np Likeness Score: 0.51

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