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

ID: ALA70288

PubChem CID: 44310722

Max Phase: Preclinical

Molecular Formula: C14H17N4NaO5

Molecular Weight: 322.32

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cn1cc([C@H](O)[C@H]2C(=O)N3C(C(=O)[O-])=C(C(C)(C)C)O[C@H]23)nn1.[Na+]

Standard InChI:  InChI=1S/C14H18N4O5.Na/c1-14(2,3)10-8(13(21)22)18-11(20)7(12(18)23-10)9(19)6-5-17(4)16-15-6;/h5,7,9,12,19H,1-4H3,(H,21,22);/q;+1/p-1/t7-,9-,12+;/m0./s1

Standard InChI Key:  DHISLSCRTLKEKY-ZLYHIZNPSA-M

Molfile:  

     RDKit          2D

 26 27  0  0  0  0  0  0  0  0999 V2000
    5.6667   -8.0625    0.0000 Na  0  0  0  0  0 15  0  0  0  0  0  0
    6.4667   -6.5750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.2542   -6.8292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4667   -5.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6417   -6.5750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6417   -5.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7292   -6.1542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2542   -5.3792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2417   -5.4917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6167   -4.8667    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9292   -5.3167    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9667   -6.1542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0542   -5.1667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5042   -7.6125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1417   -6.1125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.5542   -6.1542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0542   -7.1625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9167   -8.2667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3167   -7.7792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2667   -4.3667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6167   -6.7542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9292   -6.9042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6292   -5.3042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3292   -6.2417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7185   -6.1343    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3065   -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
  8 13  1  0
  4  9  1  0
 10  8  1  0
 11 10  2  0
 12  8  2  0
  6 13  1  0
 14  3  1  0
 15 12  1  0
 16  7  1  0
 17  5  2  0
 18 14  1  0
 19 14  2  0
 13 20  1  6
 21 15  1  0
 22 16  1  0
 23 16  1  0
 24 16  1  0
  4  6  1  0
  7  9  1  0
 11 15  1  0
  6 25  1  1
  4 26  1  6
M  CHG  2   1   1  18  -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: 322.32

Molecular Weight (Monoisotopic): 322.1277

AlogP: 0.01

#Rotatable Bonds: 3

Polar Surface Area: 117.78

Molecular Species: ACID

HBA: 7

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.57

CX Basic pKa: ┄

CX LogP: -0.30

CX LogD: -3.65

Aromatic Rings: 1

Heavy Atoms: 23

QED Weighted: 0.75

Np Likeness Score: -0.08

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