7-((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)-thieno[2,3-b]pyridin-7-ium

ID: ALA3559436

PubChem CID: 118753759

Max Phase: Preclinical

Molecular Formula: C21H18N6O5S3

Molecular Weight: 530.61

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+]3cccc4ccsc43)SC[C@H]12)c1csc(N)n1

Standard InChI:  InChI=1S/C21H18N6O5S3/c1-32-25-14(11-8-35-21(22)23-11)17(28)24-15-12-9-34-13(16(20(30)31)27(12)18(15)29)7-26-5-2-3-10-4-6-33-19(10)26/h2-6,8,12,15H,7,9H2,1H3,(H3-,22,23,24,28,30,31)/b25-14+/t12-,15+/m1/s1

Standard InChI Key:  PANLALCDUYIQBY-ZGBRBAIOSA-N

Molfile:  

     RDKit          2D

 36 40  0  0  1  0  0  0  0  0999 V2000
    3.6374   -2.3818    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.7644   -2.0798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9230   -2.7943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0499   -1.6673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3519   -2.7943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9230   -3.6193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2085   -4.8568    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.5249   -2.8195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9415   -2.2361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3958   -3.6344    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.5613   -1.8663    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.1447   -2.4497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4940   -5.2693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6374   -4.0318    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    8.1309   -4.0089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2085   -4.0318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2085   -2.3818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    8.7143   -3.4255    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.3519   -3.6193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7094   -5.0144    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    7.1551   -1.4393    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8364   -0.8704    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2245   -5.6818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4940   -6.0943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9311   -3.2466    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7094   -6.3492    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4940   -2.7943    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2600   -4.8237    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9230   -5.2693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2085   -1.5568    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9520   -1.2257    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9230   -6.0943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2085   -6.5068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1655   -0.4288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1488   -3.0078    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 16  1  0
  8  9  1  0
  9 12  1  0
 10  8  1  0
  2 11  1  1
 12 11  1  0
 13  7  2  0
 14 20  1  0
 15 10  2  0
 16  6  1  0
 17  3  1  0
 18  8  2  0
 19 18  1  0
  5 20  1  0
 21 13  1  0
 22  9  2  0
 23  4  2  0
 24 21  1  0
 25 13  1  0
 26 12  2  0
 27 25  1  0
 28 17  2  0
 29 15  1  0
 30  7  1  0
 31 17  1  0
 32 22  1  0
 33 30  2  0
 34 33  1  0
 35 32  1  0
  2  4  1  0
  6 14  1  0
 25 34  2  0
 24 27  2  0
 19 15  1  0
  5 36  1  6
M  CHG  2   7   1  31  -1
M  END

Alternative Forms

1. Parent:

   

   ALA3559436

   ---

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: 530.61

Molecular Weight (Monoisotopic): 530.0501

AlogP: -0.32

#Rotatable Bonds: 7

Polar Surface Area: 153.92

Molecular Species: ACID

HBA: 11

HBD: 2

#RO5 Violations: 2

HBA (Lipinski): 11

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 2.92

CX Basic pKa: 3.53

CX LogP: -3.75

CX LogD: -3.42

Aromatic Rings: 3

Heavy Atoms: 35

QED Weighted: 0.18

Np Likeness Score: -0.49

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