7-[(2E,4E)-5-((6S,7S)-7-{2-(2-Amino-thiazol-4-yl)-2-[(E)-methoxyimino]-acetylamino}-2-carboxy-8-oxo-4-thia-1-aza-bicyclo[4.2.0]oct-2-en-3-yl)-penta-2,4-dienyl]-thieno[2,3-b]pyridin-7-ium; Trifluoro actetate

ID: ALA612122

PubChem CID: 46877429

Max Phase: Preclinical

Molecular Formula: C27H23F3N6O7S3

Molecular Weight: 583.70

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CO/N=C(/C(=O)N[C@@H]1C(=O)N2C(C(=O)O)=C(/C=C/C=C/C[n+]3cccc4ccsc43)SC[C@H]12)c1csc(N)n1.O=C([O-])C(F)(F)F

Standard InChI:  InChI=1S/C25H22N6O5S3.C2HF3O2/c1-36-29-18(15-12-39-25(26)27-15)21(32)28-19-16-13-38-17(20(24(34)35)31(16)22(19)33)7-3-2-4-9-30-10-5-6-14-8-11-37-23(14)30;3-2(4,5)1(6)7/h2-8,10-12,16,19H,9,13H2,1H3,(H3-,26,27,28,32,34,35);(H,6,7)/b4-2+,7-3+,29-18+;/t16-,19+;/m1./s1

Standard InChI Key:  LJYZLOJYKCDMAQ-KPILZWMUSA-N

Molfile:  

     RDKit          2D

 47 50  0  0  0  0  0  0  0  0999 V2000
   -0.4333   -6.6917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4250   -5.8667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2875   -5.4542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1375   -5.4542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2583   -6.6917    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    0.3917   -6.6917    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4375   -7.5167    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    2.5250   -2.8917    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7000   -2.0667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7000   -2.8917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2250   -3.2917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5250   -2.0667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1625   -2.0667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4500   -1.6542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2125   -2.8917    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9875   -1.6542    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2625   -2.0667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2250   -2.9292    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.9375   -3.3417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0125   -3.0917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9375   -2.8917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9500   -2.0792    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.2250   -4.1292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9375   -1.7667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4625   -2.4042    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.2375   -1.6542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1000   -4.1542    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4500   -0.8292    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1250   -3.4792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.9250   -4.2417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6500   -2.9417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2625   -2.8917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6500   -3.3167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2625   -3.4917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5000   -4.5292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3750   -2.9042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0750   -3.3292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3125   -3.8667    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.8000   -2.9167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5125   -3.3292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2250   -2.1042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9375   -4.5417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1625   -0.4167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9375   -1.6917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6625   -2.1167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1625    0.4208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2656   -1.1009    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  1  0
  4  2  2  0
  5  1  1  0
  6  1  1  0
  7  1  1  0
  9 12  1  0
 10  8  1  0
 11  8  1  0
 12  8  1  0
 13 14  1  0
 14 17  1  0
 15 13  1  0
  9 16  1  1
 17 16  1  0
 18 40  1  0
 19 18  2  0
 20 15  2  0
 21 11  2  0
 22 26  1  0
 23 11  1  0
 24 13  2  0
 25 24  1  0
 12 26  1  0
 27 19  1  0
 28 14  2  0
 29 10  2  0
 30 27  1  0
 31 19  1  0
 32 17  2  0
 33 21  1  0
 34 31  1  0
 35 23  2  0
 36 33  2  0
 37 36  1  0
 38 20  1  0
 39 37  2  0
 40 39  1  0
 41 18  1  0
 42 23  1  0
 43 28  1  0
 44 41  2  0
 45 44  1  0
 46 43  1  0
 10  9  1  0
 21 22  1  0
 25 20  1  0
 31 45  2  0
 30 34  2  0
 12 47  1  6
M  CHG  2   3  -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: 583.70

Molecular Weight (Monoisotopic): 583.0887

AlogP: 2.13

#Rotatable Bonds: 9

Polar Surface Area: 151.09

Molecular Species: ACID

HBA: 10

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 11

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 3.44

CX Basic pKa: 2.98

CX LogP: -2.66

CX LogD: -2.37

Aromatic Rings: 3

Heavy Atoms: 39

QED Weighted: 0.11

Np Likeness Score: -0.14

References

1. Aszodi J, Bonnet A, Chantot J, Costerousse G, Didierlaurent S, Teutsch G.  (1993)  Vinylogous vs arylogous isocephems,  3  (11): [10.1016/S0960-894X(01)80930-6]

Source

Source(1):

• Scientific Literature