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

ID: ALA71293

PubChem CID: 44310277

Max Phase: Preclinical

Molecular Formula: C13H16NNaO7

Molecular Weight: 299.28

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COC(=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/C13H17NO7.Na/c1-13(2,3)8-6(11(17)18)14-9(16)5(10(14)21-8)7(15)12(19)20-4;/h5,7,10,15H,1-4H3,(H,17,18);/q;+1/p-1/t5-,7-,10+;/m0./s1

Standard InChI Key:  UIADBKOHHFCPGT-PROYFIQGSA-M

Molfile:  

     RDKit          2D

 24 24  0  0  0  0  0  0  0  0999 V2000
    5.3542   -8.0625    0.0000 Na  0  0  0  0  0 15  0  0  0  0  0  0
    6.1542   -6.5750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.9417   -6.8292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1542   -5.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3292   -6.5750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3292   -5.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4167   -6.1542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9292   -5.4917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1917   -7.6125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7417   -5.1667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9417   -5.3792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2417   -6.1542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7417   -7.1625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5417   -8.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0042   -7.7792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3542   -4.7917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9542   -4.3667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7292   -6.1792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6167   -6.9042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3167   -5.3042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0167   -6.2417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9292   -6.3917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4060   -6.1343    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9940   -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  3  1  0
  6 10  1  0
 11 10  1  0
 12  7  1  0
 13  5  2  0
 14  9  1  0
 15  9  2  0
 16 11  2  0
 10 17  1  1
 18 11  1  0
 19 12  1  0
 20 12  1  0
 21 12  1  0
 22 18  1  0
  4  6  1  0
  7  8  1  0
  6 23  1  1
  4 24  1  6
M  CHG  2   1   1  14  -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: 299.28

Molecular Weight (Monoisotopic): 299.1005

AlogP: -0.32

#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: 3.88

CX Basic pKa: ┄

CX LogP: -0.53

CX LogD: -3.75

Aromatic Rings: ┄

Heavy Atoms: 21

QED Weighted: 0.54

Np Likeness Score: 0.78

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