1-{3-[(E)-2-((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)-vinyl]-benzyl}-pyridinium

ID: ALA3559432

PubChem CID: 118753756

Max Phase: Preclinical

Molecular Formula: C27H24N6O5S2

Molecular Weight: 576.66

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/c3cccc(C[n+]4ccccc4)c3)SC[C@H]12)c1csc(N)n1

Standard InChI:  InChI=1S/C27H24N6O5S2/c1-38-31-21(18-14-40-27(28)29-18)24(34)30-22-19-15-39-20(23(26(36)37)33(19)25(22)35)9-8-16-6-5-7-17(12-16)13-32-10-3-2-4-11-32/h2-12,14,19,22H,13,15H2,1H3,(H3-,28,29,30,34,36,37)/b9-8+,31-21+/t19-,22+/m1/s1

Standard InChI Key:  YREYAITURYEAMQ-LLBLETOXSA-N

Molfile:  

     RDKit          2D

 41 45  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
    5.9917   -3.7292    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
    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
   10.9875   -4.1667    0.0000 N   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
    6.7042   -4.1500    0.0000 C   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
    7.4250   -3.7417    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
   10.2667   -3.7542    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
    9.5542   -4.1667    0.0000 C   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
    5.9875   -5.3792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8417   -3.7542    0.0000 C   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
   10.9792   -4.9917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6917   -3.7542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8375   -5.4042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5542   -4.9917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1250   -4.9875    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
   12.4042   -4.1667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6917   -5.4042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4042   -5.0000    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  4  2  0
 12  8  2  0
 13 18  1  0
 14  4  1  0
 15 24  1  0
 16  6  2  0
 17 16  1  0
  5 18  1  0
 19 11  1  0
 20  7  2  0
 21  3  2  0
 22 19  2  0
 23 10  2  0
 24 27  1  0
 25 14  2  0
 26 12  1  0
 27 30  2  0
 28 22  1  0
 29 14  1  0
 30 28  1  0
 31 20  1  0
 32 15  2  0
 33 15  1  0
 34 36  1  0
 35 34  2  0
 36 28  2  0
 37 31  1  0
 38 33  2  0
 39 32  1  0
 40 38  1  0
  3  2  1  0
 11 13  1  0
 17 12  1  0
 27 35  1  0
 39 40  2  0
  5 41  1  6
M  CHG  2  15   1  29  -1
M  END

Alternative Forms

1. Parent:

   

   ALA3559432

   ---

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: 576.66

Molecular Weight (Monoisotopic): 576.1250

AlogP: 0.53

#Rotatable Bonds: 9

Polar Surface Area: 153.92

Molecular Species: ACID

HBA: 10

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 11

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 3.51

CX Basic pKa: 3.02

CX LogP: -2.60

CX LogD: -2.32

Aromatic Rings: 3

Heavy Atoms: 40

QED Weighted: 0.16

Np Likeness Score: -0.25

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