((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)-trimethyl-ammonium

ID: ALA3559440

PubChem CID: 118753763

Max Phase: Preclinical

Molecular Formula: C17H22N6O5S2

Molecular Weight: 454.53

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

Standard InChI:  InChI=1S/C17H22N6O5S2/c1-23(2,3)5-10-13(16(26)27)22-9(7-29-10)12(15(22)25)20-14(24)11(21-28-4)8-6-30-17(18)19-8/h6,9,12H,5,7H2,1-4H3,(H3-,18,19,20,24,26,27)/b21-11+/t9-,12+/m1/s1

Standard InChI Key:  UOEDPNMRZHOLNZ-GNWUKDCASA-N

Molfile:  

     RDKit          2D

 31 33  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
    5.2792   -4.1292    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
    4.5792   -2.9042    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
    0.8917   -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
    6.0000   -2.9125    0.0000 S   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
    5.2750   -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
    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 N   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
    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
    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
    8.1292   -4.1625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4292   -2.9167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6292   -4.5417    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  3  2  0
  7  8  1  0
  8 11  1  0
  9  7  1  0
  2 10  1  1
 11 10  1  0
 12 17  1  0
 13  9  2  0
 14  3  1  0
 15  7  2  0
 16 15  1  0
  5 17  1  0
 18  6  1  0
 19  8  2  0
 20  4  2  0
 21 18  1  0
 22 11  2  0
 23 14  2  0
 24 13  1  0
 25 14  1  0
 26 19  1  0
 27 21  1  0
 28 21  1  0
 29 21  1  0
 30 26  1  0
  2  4  1  0
  6 12  1  0
 16 13  1  0
  5 31  1  6
M  CHG  2  21   1  25  -1
M  END

Alternative Forms

1. Parent:

   

   ALA3559440

   ---

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: 454.53

Molecular Weight (Monoisotopic): 454.1093

AlogP: -1.81

#Rotatable Bonds: 7

Polar Surface Area: 150.04

Molecular Species: ACID

HBA: 10

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 11

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 3.75

CX Basic pKa: 2.98

CX LogP: -5.24

CX LogD: -4.36

Aromatic Rings: 1

Heavy Atoms: 30

QED Weighted: 0.21

Np Likeness Score: -0.21

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