7-[(E)-3-((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)-allyl]-thieno[2,3-b]pyridin-7-ium

ID: ALA3559439

PubChem CID: 118753762

Max Phase: Preclinical

Molecular Formula: C23H20N6O5S3

Molecular Weight: 556.65

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[n+]3cccc4ccsc43)SC[C@H]12)c1csc(N)n1

Standard InChI:  InChI=1S/C23H20N6O5S3/c1-34-27-16(13-10-37-23(24)25-13)19(30)26-17-14-11-36-15(18(22(32)33)29(14)20(17)31)5-3-8-28-7-2-4-12-6-9-35-21(12)28/h2-7,9-10,14,17H,8,11H2,1H3,(H3-,24,25,26,30,32,33)/b5-3+,27-16+/t14-,17+/m1/s1

Standard InChI Key:  MSYNZYWWMXJIBK-YEORGRHGSA-N

Molfile:  

     RDKit          2D

 38 42  0  0  1  0  0  0  0  0999 V2000
    4.5750   -3.7250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7542   -2.9042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7542   -3.7292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2792   -4.1292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5792   -2.9042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8917   -2.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6042   -2.4875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8375   -3.7250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0375   -2.4917    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3167   -2.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8542   -3.7542    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.5625   -4.1750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0417   -3.9292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9917   -3.7292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0000   -2.9125    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.2750   -4.9625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1167   -2.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4083   -3.2375    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.2917   -2.4917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7292   -4.9792    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.6042   -1.6625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1750   -4.3167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.5417   -5.0667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2792   -3.7667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7042   -4.1500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3167   -3.7250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4250   -3.7417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8875   -4.3167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5542   -5.3667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2625   -4.7042    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.1292   -4.1625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8542   -2.9292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9875   -5.3792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8917   -1.2500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.5667   -2.5250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2792   -2.9417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8917   -0.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3198   -1.9384    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  5  1  0
  3  1  1  0
  4  1  1  0
  5  1  1  0
  6  7  1  0
  7 10  1  0
  8  6  1  0
  2  9  1  1
 10  9  1  0
 11 31  1  0
 12 11  2  0
 13  8  2  0
 14  4  2  0
 15 19  1  0
 16  4  1  0
 17  6  2  0
 18 17  1  0
  5 19  1  0
 20 12  1  0
 21  7  2  0
 22  3  2  0
 23 20  1  0
 24 12  1  0
 25 14  1  0
 26 10  2  0
 27 25  2  0
 28 24  1  0
 29 16  2  0
 30 13  1  0
 31 27  1  0
 32 11  1  0
 33 16  1  0
 34 21  1  0
 35 32  2  0
 36 35  1  0
 37 34  1  0
  2  3  1  0
 14 15  1  0
 18 13  1  0
 24 36  2  0
 23 28  2  0
  5 38  1  6
M  CHG  2  11   1  33  -1
M  END

Alternative Forms

1. Parent:

   

   ALA3559439

   ---

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: 556.65

Molecular Weight (Monoisotopic): 556.0657

AlogP: 0.24

#Rotatable Bonds: 8

Polar Surface Area: 153.92

Molecular Species: ACID

HBA: 11

HBD: 2

#RO5 Violations: 2

HBA (Lipinski): 11

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 2.91

CX Basic pKa: 3.52

CX LogP: -3.22

CX LogD: -2.90

Aromatic Rings: 3

Heavy Atoms: 37

QED Weighted: 0.17

Np Likeness Score: -0.38

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