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

ID: ALA71330

PubChem CID: 44310462

Max Phase: Preclinical

Molecular Formula: C19H22NNaO5

Molecular Weight: 345.40

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)(C)C1=C(C(=O)[O-])N2C(=O)[C@H]([C@H](O)CCc3ccccc3)[C@H]2O1.[Na+]

Standard InChI:  InChI=1S/C19H23NO5.Na/c1-19(2,3)15-14(18(23)24)20-16(22)13(17(20)25-15)12(21)10-9-11-7-5-4-6-8-11;/h4-8,12-13,17,21H,9-10H2,1-3H3,(H,23,24);/q;+1/p-1/t12-,13+,17-;/m1./s1

Standard InChI Key:  IQEVCFYTZYLNSC-GNKAQWJKSA-M

Molfile:  

     RDKit          2D

 28 29  0  0  0  0  0  0  0  0999 V2000
    6.3292   -8.0625    0.0000 Na  0  0  0  0  0 15  0  0  0  0  0  0
    7.1375   -6.5750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.9167   -6.8292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1292   -5.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3042   -6.5750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4000   -6.1542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3042   -5.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9125   -5.4917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1750   -7.6125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2250   -6.1542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7167   -7.1625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7167   -5.1667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4792   -8.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9875   -7.7792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9250   -5.3792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3375   -4.7917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9375   -4.3667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5417   -5.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6000   -6.9042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3000   -5.3042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0000   -6.2417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9625   -4.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3375   -5.8042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5417   -6.0167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1667   -4.6375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9500   -5.4375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3810   -6.1343    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9706   -4.7627    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  3  1  0
 10  6  1  0
 11  5  2  0
  7 12  1  0
 13  9  1  0
 14  9  2  0
 15 12  1  0
 16 15  1  0
 12 17  1  1
 18 16  1  0
 19 10  1  0
 20 10  1  0
 21 10  1  0
 22 18  2  0
 23 18  1  0
 24 23  2  0
 25 22  1  0
 26 25  2  0
  4  7  1  0
  6  8  1  0
 24 26  1  0
  7 27  1  1
  4 28  1  6
M  CHG  2   1   1  13  -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: 345.40

Molecular Weight (Monoisotopic): 345.1576

AlogP: 2.14

#Rotatable Bonds: 5

Polar Surface Area: 87.07

Molecular Species: ACID

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 4.10

CX Basic pKa: ┄

CX LogP: 2.15

CX LogD: -0.95

Aromatic Rings: 1

Heavy Atoms: 25

QED Weighted: 0.80

Np Likeness Score: 0.71

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