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

ID: ALA71465

PubChem CID: 44310738

Max Phase: Preclinical

Molecular Formula: C17H18NNaO6

Molecular Weight: 333.34

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)(C)C1=C(C(=O)[O-])N2C(=O)[C@H]([C@@H](O)c3ccc(O)cc3)[C@H]2O1.[Na+]

Standard InChI:  InChI=1S/C17H19NO6.Na/c1-17(2,3)13-11(16(22)23)18-14(21)10(15(18)24-13)12(20)8-4-6-9(19)7-5-8;/h4-7,10,12,15,19-20H,1-3H3,(H,22,23);/q;+1/p-1/t10-,12-,15+;/m0./s1

Standard InChI Key:  WZTWQJZRCWQREE-XMUWTWQESA-M

Molfile:  

     RDKit          2D

 27 28  0  0  0  0  0  0  0  0999 V2000
    6.3375   -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
    7.9250   -6.8292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1375   -5.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3125   -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
    6.3125   -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
    5.7250   -5.1667    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
    5.7250   -7.1625    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
    7.4500   -8.3292    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
    4.3375   -4.7917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7125   -6.1750    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
    3.3375   -5.8042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9250   -6.3917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5500   -5.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5375   -6.0167    0.0000 O   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
    9.6000   -6.9042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3893   -6.1343    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9773   -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  3  2  0
  7  5  1  0
  4  8  1  0
  9  3  1  0
  7 10  1  0
 11  6  1  0
 12  5  2  0
 13 10  1  0
 14  9  1  0
 15  9  2  0
 16 13  2  0
 17 13  1  0
 10 18  1  6
 19 20  1  0
 20 17  2  0
 21 16  1  0
 22 19  1  0
 23 11  1  0
 24 11  1  0
 25 11  1  0
  4  7  1  0
  6  8  1  0
 21 19  2  0
  7 26  1  1
  4 27  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: 333.34

Molecular Weight (Monoisotopic): 333.1212

AlogP: 1.58

#Rotatable Bonds: 3

Polar Surface Area: 107.30

Molecular Species: ACID

HBA: 5

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.97

CX Basic pKa: ┄

CX LogP: 1.12

CX LogD: -2.07

Aromatic Rings: 1

Heavy Atoms: 24

QED Weighted: 0.73

Np Likeness Score: 0.74

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