1-((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-ylmethyl)-pyridinium

ID: ALA3559429

PubChem CID: 118753753

Max Phase: Preclinical

Molecular Formula: C19H18N6O5S2

Molecular Weight: 474.52

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[n+]3ccccc3)SC[C@H]12)c1csc(N)n1

Standard InChI:  InChI=1S/C19H18N6O5S2/c1-30-23-13(10-8-32-19(20)21-10)16(26)22-14-11-9-31-12(7-24-5-3-2-4-6-24)15(18(28)29)25(11)17(14)27/h2-6,8,11,14H,7,9H2,1H3,(H3-,20,21,22,26,28,29)/b23-13+/t11-,14+/m1/s1

Standard InChI Key:  VCGHCYUYZBTTOZ-LOSXEJHPSA-N

Molfile:  

     RDKit          2D

 33 36  0  0  1  0  0  0  0  0999 V2000
    3.4171   -3.2354    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5921   -2.4104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1316   -3.6479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5921   -3.2354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4171   -2.4104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8460   -3.2354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8524    0.3501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6389   -0.4468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6226    0.6458    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0087   -1.8270    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2223   -1.0301    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8460   -2.4104    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.5795    1.4696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2750   -3.2354    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1316   -4.4729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3332    0.9913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7826    1.6832    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.1316   -1.9979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5605   -3.6479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8420   -0.6603    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0087   -3.8188    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0192   -0.8166    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4171   -4.8854    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2206    1.9888    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8460   -4.8854    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2587   -0.0769    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9895   -3.6479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2750   -2.4104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5382   -0.2905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9895   -1.9979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7039   -3.2354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7039   -2.4104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2036   -1.6135    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  3  2  0
  7  8  1  0
  8 11  1  0
  9  7  1  0
  2 10  1  1
 11 10  1  0
 12 18  1  0
 13  9  2  0
 14 19  1  0
 15  3  1  0
 16  7  2  0
 17 16  1  0
  5 18  1  0
 19  6  1  0
 20  8  2  0
 21  4  2  0
 22 11  2  0
 23 15  2  0
 24 13  1  0
 25 15  1  0
 26 20  1  0
 27 14  2  0
 28 14  1  0
 29 26  1  0
 30 28  2  0
 31 27  1  0
 32 30  1  0
  2  4  1  0
  6 12  1  0
 31 32  2  0
 17 13  1  0
  5 33  1  6
M  CHG  2  14   1  25  -1
M  END

Alternative Forms

1. Parent:

   

   ALA3559429

   ---

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: 474.52

Molecular Weight (Monoisotopic): 474.0780

AlogP: -1.53

#Rotatable Bonds: 7

Polar Surface Area: 153.92

Molecular Species: ACID

HBA: 10

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 11

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 2.88

CX Basic pKa: 3.50

CX LogP: -4.92

CX LogD: -4.58

Aromatic Rings: 2

Heavy Atoms: 32

QED Weighted: 0.21

Np Likeness Score: -0.34

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