[(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]-trimethyl-ammonium

ID: ALA3559437

PubChem CID: 118753760

Max Phase: Preclinical

Molecular Formula: C19H24N6O5S2

Molecular Weight: 480.57

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

Standard InChI:  InChI=1S/C19H24N6O5S2/c1-25(2,3)7-5-6-12-15(18(28)29)24-11(9-31-12)14(17(24)27)22-16(26)13(23-30-4)10-8-32-19(20)21-10/h5-6,8,11,14H,7,9H2,1-4H3,(H3-,20,21,22,26,28,29)/b6-5+,23-13+/t11-,14+/m1/s1

Standard InChI Key:  AYTVKFGRFVPYNC-QRSUITQKSA-N

Molfile:  

     RDKit          2D

 33 35  0  0  1  0  0  0  0  0999 V2000
    3.8483   -4.7095    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0233   -3.8845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0233   -4.7095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5628   -5.1220    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8483   -3.8845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2836   -1.1240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701   -1.9209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0538   -0.8284    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4399   -3.3011    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6535   -2.5043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0107   -0.0045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2772   -4.7095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2772   -3.8845    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.5628   -5.9470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7644   -0.4829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2138    0.2090    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.5628   -3.4720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2732   -2.1344    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4399   -5.2929    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1351   -4.7095    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.9917   -5.1220    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4504   -2.2907    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7062   -4.7095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2772   -6.3595    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6518    0.5147    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8483   -6.3595    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4207   -5.1220    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6899   -1.5511    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8496   -4.2970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5476   -5.4240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7226   -3.9950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1070   -1.7646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6348   -3.0876    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  8  2  0
 12  4  2  0
 13 17  1  0
 14  4  1  0
 15  6  2  0
 16 15  1  0
  5 17  1  0
 18  7  2  0
 19  3  2  0
 20 27  1  0
 21 12  1  0
 22 10  2  0
 23 21  2  0
 24 14  2  0
 25 11  1  0
 26 14  1  0
 27 23  1  0
 28 18  1  0
 29 20  1  0
 30 20  1  0
 31 20  1  0
 32 28  1  0
  2  3  1  0
 12 13  1  0
 16 11  1  0
  5 33  1  6
M  CHG  2  20   1  26  -1
M  END

Alternative Forms

1. Parent:

   

   ALA3559437

   ---

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: 480.57

Molecular Weight (Monoisotopic): 480.1250

AlogP: -1.26

#Rotatable Bonds: 8

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: 3.79

CX Basic pKa: 3.03

CX LogP: -4.74

CX LogD: -3.84

Aromatic Rings: 1

Heavy Atoms: 32

QED Weighted: 0.20

Np Likeness Score: -0.08

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