Ethyl 4-Hydroxy-5-oxo-1-(6-phenoxybenzo[d]thiazol-2-yl)-2-phenyl-2,5-dihydro-1H-pyrrole-3-carboxylate

ID: ALA5220749

PubChem CID: 168299228

Max Phase: Preclinical

Molecular Formula: C26H20N2O5S

Molecular Weight: 472.52

Names and Identifiers

Canonical SMILES:  CCOC(=O)C1=C(O)C(=O)N(c2nc3ccc(Oc4ccccc4)cc3s2)C1c1ccccc1

Standard InChI:  InChI=1S/C26H20N2O5S/c1-2-32-25(31)21-22(16-9-5-3-6-10-16)28(24(30)23(21)29)26-27-19-14-13-18(15-20(19)34-26)33-17-11-7-4-8-12-17/h3-15,22,29H,2H2,1H3

Standard InChI Key:  BMIUGZBLDWZORY-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 34 38  0  0  0  0  0  0  0  0999 V2000
    1.2679    1.5162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0929    1.5162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3430    0.7122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6895    0.2416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0221    0.7334    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6895   -0.5831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1396    0.4987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7228    1.0819    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3531   -0.2978    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5053    2.2304    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8555    2.2304    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5195    0.8685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1026    1.4516    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4036   -0.9957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4029   -1.8179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6884   -2.2304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9769   -1.8214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9722   -0.9972    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2254    0.5200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0120   -0.2765    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8289   -0.3100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1143    0.4427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4667    0.9599    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3370   -0.9313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1319   -0.8022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4175   -0.0539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9124    0.5723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7151   -1.3854    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5117   -1.1720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0951   -1.7550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8891   -1.5415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1026   -0.7446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5235   -0.1632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7261   -0.3720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  5  4  1  0
  1  5  1  0
  4  6  1  0
  3  7  1  0
  7  8  1  0
  7  9  2  0
  2 10  1  0
  1 11  2  0
  8 12  1  0
 12 13  1  0
 14  6  2  0
 15 14  1  0
 16 15  2  0
 17 16  1  0
 18 17  2  0
  6 18  1  0
 19  5  1  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 19 23  2  0
 23 22  1  0
 21 24  1  0
 25 24  2  0
 26 25  1  0
 27 26  2  0
 22 27  1  0
 25 28  1  0
 28 29  1  0
 30 29  2  0
 31 30  1  0
 32 31  2  0
 33 32  1  0
 34 33  2  0
 29 34  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5220749

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type:

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 472.52

Molecular Weight (Monoisotopic): 472.1093

AlogP: 5.55

#Rotatable Bonds: 6

Polar Surface Area: 88.96

Molecular Species: NEUTRAL

HBA: 7

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 7

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 7.55

CX Basic pKa: ┄

CX LogP: 5.22

CX LogD: 4.99

Aromatic Rings: 4

Heavy Atoms: 34

QED Weighted: 0.37

Np Likeness Score: -1.39

References

1. Fathalla RK, Fröhner W, Bader CD, Fischer PD, Dahlem C, Chatterjee D, Mathea S, Kiemer AK, Arthanari H, Müller R, Abdel-Halim M, Ducho C, Engel M..  (2022)  Identification and Biochemical Characterization of Pyrrolidinediones as Novel Inhibitors of the Bacterial Enzyme MurA.,  65  (21.0): [PMID:36269107] [10.1021/acs.jmedchem.2c01275]

Source

Source(1):

• Scientific Literature