Isocephem derivative

ID: ALA69997

PubChem CID: 44311150

Max Phase: Preclinical

Molecular Formula: C21H20N6O5S2

Molecular Weight: 500.56

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/c3cc[n+](C)cc3)SC[C@H]12)c1csc(N)n1

Standard InChI:  InChI=1S/C21H20N6O5S2/c1-26-7-5-11(6-8-26)3-4-14-17(20(30)31)27-13(10-33-14)16(19(27)29)24-18(28)15(25-32-2)12-9-34-21(22)23-12/h3-9,13,16H,10H2,1-2H3,(H3-,22,23,24,28,30,31)/b25-15+/t13-,16+/m1/s1

Standard InChI Key:  CJWGVHHUTXFEAZ-YXFSDHRCSA-N

Molfile:  

     RDKit          2D

 35 38  0  0  1  0  0  0  0  0999 V2000
    5.0917   -3.2542    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2750   -2.4375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2750   -3.2625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7917   -3.6667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1000   -2.4375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4042   -2.4292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1250   -2.0167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3542   -3.2542    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5542   -2.0250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8375   -2.4292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5125   -3.2667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5542   -3.4667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7917   -4.4917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5167   -2.4417    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   10.0667   -4.5292    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6375   -2.1292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1125   -2.7667    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.8042   -2.0292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2250   -3.6792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1250   -1.1917    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6917   -3.8500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9417   -3.2792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8375   -3.2542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5042   -4.9125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0750   -4.9042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2542   -4.2375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.3542   -4.9375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0750   -3.7000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6500   -3.6917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4042   -0.7792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7792   -4.9417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3625   -3.2875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6417   -4.5167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4042    0.0458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8403   -1.4718    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  4  1  0
 14 18  1  0
 15 27  2  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 13  1  0
 25 13  2  0
 26 12  1  0
 27 33  1  0
 28 32  2  0
 29 22  1  0
 30 20  1  0
 31 15  1  0
 32 29  1  0
 33 29  2  0
 34 30  1  0
  2  3  1  0
 11 14  1  0
 28 15  1  0
 17 12  1  0
  5 35  1  6
M  CHG  2  15   1  24  -1
M  END

Alternative Forms

1. Parent:

   

   ALA69997

   (6S,7S)-7-[[(2E)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-3-[(E)-2-(1-methylpyridin-1-ium-4-yl)ethenyl]-8-oxo-4-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

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: 500.56

Molecular Weight (Monoisotopic): 500.0937

AlogP: -0.98

#Rotatable Bonds: 7

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: 2.91

CX Basic pKa: 3.52

CX LogP: -4.38

CX LogD: -4.05

Aromatic Rings: 2

Heavy Atoms: 34

QED Weighted: 0.21

Np Likeness Score: -0.20

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