Sodium salt (5R,6S)-3-butoxy-6-((R)-1-hydroxy-ethyl)-7-oxo-4-thia-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylate

ID: ALA317678

PubChem CID: 44327122

Max Phase: Preclinical

Molecular Formula: C12H16NNaO5S

Molecular Weight: 287.34

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCCOC1=C(C(=O)[O-])N2C(=O)[C@H]([C@@H](C)O)[C@H]2S1.[Na+]

Standard InChI:  InChI=1S/C12H17NO5S.Na/c1-3-4-5-18-12-8(11(16)17)13-9(15)7(6(2)14)10(13)19-12;/h6-7,10,14H,3-5H2,1-2H3,(H,16,17);/q;+1/p-1/t6-,7+,10-;/m1./s1

Standard InChI Key:  SZTKZBXMHPVBGZ-OFVIFIGMSA-M

Molfile:  

     RDKit          2D

 22 22  0  0  0  0  0  0  0  0999 V2000
    4.8667   -5.5375    0.0000 Na  0  0  0  0  0 15  0  0  0  0  0  0
    3.9292   -2.6000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9417   -1.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7167   -2.8625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1042   -2.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7167   -1.5250    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.2042   -2.1917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1042   -1.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9667   -3.6417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5292   -3.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4042   -4.2542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5292   -1.1917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7667   -3.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0292   -2.2000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7417   -0.3917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7292   -1.4042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4417   -2.9125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2667   -2.9167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6667   -3.6375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4917   -3.6375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1790   -2.1544    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7863   -0.7871    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
  3  6  1  0
  7  4  2  0
  8  5  1  0
  9  4  1  0
 10  5  2  0
 11  9  1  0
  8 12  1  0
 13  9  2  0
 14  7  1  0
 12 15  1  1
 16 12  1  0
 17 14  1  0
 18 17  1  0
 19 18  1  0
 20 19  1  0
  8  3  1  0
  6  7  1  0
  8 21  1  1
  3 22  1  6
M  CHG  2   1   1  11  -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: 287.34

Molecular Weight (Monoisotopic): 287.0827

AlogP: 0.97

#Rotatable Bonds: 6

Polar Surface Area: 87.07

Molecular Species: ACID

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.97

CX Basic pKa: ┄

CX LogP: 0.83

CX LogD: -2.35

Aromatic Rings: ┄

Heavy Atoms: 19

QED Weighted: 0.56

Np Likeness Score: 0.37

References

1. Afonso A, Hon F, Fett N, Weinstein J, Ganguly AK, Naples L, Hare RS, Miller GH..  (1998)  Synthesis and antibacterial activity of 2-alkoxy penems.,  8  (19): [PMID:9873624] [10.1016/s0960-894x(98)00502-2]

Source

Source(1):

• Scientific Literature