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

ID: ALA302541

PubChem CID: 44310272

Max Phase: Preclinical

Molecular Formula: C17H18NNaO5

Molecular Weight: 317.34

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)(C)C1=C(C(=O)[O-])N2C(=O)[C@H]([C@@H](O)c3ccccc3)[C@H]2O1.[Na+]

Standard InChI:  InChI=1S/C17H19NO5.Na/c1-17(2,3)13-11(16(21)22)18-14(20)10(15(18)23-13)12(19)9-7-5-4-6-8-9;/h4-8,10,12,15,19H,1-3H3,(H,21,22);/q;+1/p-1/t10-,12-,15+;/m0./s1

Standard InChI Key:  RQIMLMBSRGJWHU-XMUWTWQESA-M

Molfile:  

     RDKit          2D

 26 27  0  0  0  0  0  0  0  0999 V2000
    5.6375   -8.0417    0.0000 Na  0  0  0  0  0 15  0  0  0  0  0  0
    6.4417   -6.5542    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.2250   -6.8125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4375   -5.7292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6125   -6.5542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7042   -6.1375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6125   -5.7292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2167   -5.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4792   -7.5917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0250   -5.1500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5292   -6.1375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0250   -7.1417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9792   -8.2417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2917   -7.7625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2292   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2417   -4.3500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9042   -6.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6042   -5.2875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3042   -6.2250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0167   -6.1542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6417   -4.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8500   -4.9917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2250   -6.3750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6375   -5.7875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6900   -6.1152    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2805   -4.7416    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  9  1  0
 14  9  2  0
 15 10  1  0
 10 16  1  6
 17 11  1  0
 18 11  1  0
 19 11  1  0
 20 15  1  0
 21 15  2  0
 22 21  1  0
 23 20  2  0
 24 23  1  0
  4  7  1  0
  6  8  1  0
 22 24  2  0
  7 25  1  1
  4 26  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: 317.34

Molecular Weight (Monoisotopic): 317.1263

AlogP: 1.88

#Rotatable Bonds: 3

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: 1.42

CX LogD: -1.68

Aromatic Rings: 1

Heavy Atoms: 23

QED Weighted: 0.83

Np Likeness Score: 0.52

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