2,3-Dihydro-2-benzyl-5-(2-nitrobenzyl)-1,5-benzothiazepin-4(5H)-one

ID: ALA2334795

PubChem CID: 71578377

Max Phase: Preclinical

Molecular Formula: C23H20N2O3S

Molecular Weight: 404.49

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C1CC(Cc2ccccc2)Sc2ccccc2N1Cc1ccccc1[N+](=O)[O-]

Standard InChI:  InChI=1S/C23H20N2O3S/c26-23-15-19(14-17-8-2-1-3-9-17)29-22-13-7-6-12-21(22)24(23)16-18-10-4-5-11-20(18)25(27)28/h1-13,19H,14-16H2

Standard InChI Key:  JWGACCWJXAJASM-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   10.4869  -17.7113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3049  -17.7355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7330  -17.0403    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3443  -16.3205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5231  -16.3002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0987  -16.9961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9954  -18.0236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9943  -18.8431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7023  -19.2521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7006  -17.6147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4084  -18.8423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4092  -18.0200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0552  -17.5021    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    8.0568  -19.3574    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.8613  -17.6796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8628  -19.1712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2177  -18.4242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3749  -19.8081    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0512  -20.1746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3408  -20.5784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6373  -20.1611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9273  -20.5642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9213  -21.3823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6313  -21.7955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3383  -21.3900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2824  -16.9793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0460  -21.8010    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.7549  -21.3945    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0436  -22.6181    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  1  1  0
  7  8  2  0
  8  9  1  0
  9 11  2  0
 12 10  2  0
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 11 12  1  0
 12 13  1  0
 11 14  1  0
 13 15  1  0
 14 16  1  0
 15 17  1  0
 16 17  1  0
 16 18  2  0
 14 19  1  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 20  1  0
 15 26  1  0
 26  6  1  0
 27 28  2  0
 27 29  1  0
 25 27  1  0
M  CHG  2  27   1  29  -1
M  END

Alternative Forms

1. Parent:

   

   ALA2334795

   2-Benzyl-5-[(2-nitrophenyl)methyl]-2,3-dihydro-1,5-benzothiazepin-4-one

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: 404.49

Molecular Weight (Monoisotopic): 404.1195

AlogP: 5.24

#Rotatable Bonds: 5

Polar Surface Area: 63.45

Molecular Species: NEUTRAL

HBA: 4

HBD: ┄

#RO5 Violations: 1

HBA (Lipinski): 5

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 5.17

CX LogD: 5.17

Aromatic Rings: 3

Heavy Atoms: 29

QED Weighted: 0.43

Np Likeness Score: -1.01

References

1. Zhang P, Hu HR, Bian SH, Huang ZH, Chu Y, Ye DY..  (2013)  Design, synthesis and biological evaluation of benzothiazepinones (BTZs) as novel non-ATP competitive inhibitors of glycogen synthase kinase-3β (GSK-3β).,  61  [PMID:23047001] [10.1016/j.ejmech.2012.09.021]

Source

Source(1):

• Scientific Literature