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

ID: ALA302083

PubChem CID: 44310225

Max Phase: Preclinical

Molecular Formula: C19H22NNaO6

Molecular Weight: 361.39

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)(C)C1=C(C(=O)[O-])N2C(=O)[C@H]([C@@H](O)CCc3ccc(O)cc3)[C@H]2O1.[Na+]

Standard InChI:  InChI=1S/C19H23NO6.Na/c1-19(2,3)15-14(18(24)25)20-16(23)13(17(20)26-15)12(22)9-6-10-4-7-11(21)8-5-10;/h4-5,7-8,12-13,17,21-22H,6,9H2,1-3H3,(H,24,25);/q;+1/p-1/t12-,13-,17+;/m0./s1

Standard InChI Key:  XGPLZIOCXILJCX-BMMKQCRMSA-M

Molfile:  

     RDKit          2D

 29 30  0  0  0  0  0  0  0  0999 V2000
    6.7750   -8.0917    0.0000 Na  0  0  0  0  0 15  0  0  0  0  0  0
    7.8250   -6.5667    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.6125   -6.8167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8250   -5.7417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0000   -6.5667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1000   -6.1542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0000   -5.7417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6000   -5.4792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8750   -7.6042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9125   -6.1417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4125   -7.1542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4125   -5.1542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2000   -8.3917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.6750   -7.7667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6125   -5.3792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2375   -5.0042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6500   -5.4292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0375   -4.7917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8625   -4.6292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2375   -6.0167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6625   -4.4167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0250   -5.7917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6250   -4.3667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8500   -5.6417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.2875   -6.9042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9875   -5.2917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6875   -6.2292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0761   -6.1244    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6624   -4.7550    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 18  1  0
 17 20  1  0
 18 15  1  0
 19 21  1  0
 20 22  2  0
 21 16  2  0
 22 16  1  0
 12 23  1  6
 24 17  1  0
 25 10  1  0
 26 10  1  0
 27 10  1  0
  4  7  1  0
  6  8  1  0
 19 17  2  0
  7 28  1  1
  4 29  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: 361.39

Molecular Weight (Monoisotopic): 361.1525

AlogP: 1.84

#Rotatable Bonds: 5

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: 4.09

CX Basic pKa: ┄

CX LogP: 1.85

CX LogD: -1.26

Aromatic Rings: 1

Heavy Atoms: 26

QED Weighted: 0.69

Np Likeness Score: 0.90

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