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

ID: ALA2207940

PubChem CID: 71456067

Max Phase: Preclinical

Molecular Formula: C22H18N2O3S

Molecular Weight: 390.46

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C1CC(c2ccccc2)Sc2ccccc2N1Cc1ccccc1[N+](=O)[O-]

Standard InChI:  InChI=1S/C22H18N2O3S/c25-22-14-21(16-8-2-1-3-9-16)28-20-13-7-6-12-19(20)23(22)15-17-10-4-5-11-18(17)24(26)27/h1-13,21H,14-15H2

Standard InChI Key:  JRGHTWHRFQCWSR-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 28 31  0  0  0  0  0  0  0  0999 V2000
   13.4554  -20.7161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4542  -21.5431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1687  -21.9558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1669  -20.3035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8830  -21.5385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8820  -20.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5298  -20.1909    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   15.5352  -22.0546    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.3390  -20.3684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3447  -21.8658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6995  -21.1146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8628  -22.5074    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.8496  -19.7215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6665  -19.8420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1774  -19.1957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8724  -18.4284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0518  -18.3115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5446  -18.9590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3552  -22.8594    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5681  -23.1058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9643  -22.5474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1779  -22.7932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9971  -23.5987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6090  -24.1580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3930  -23.9092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0031  -24.4645    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.7889  -24.2145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.8268  -25.2701    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  5  2  0
  6  4  2  0
  4  1  1  0
  5  6  1  0
  6  7  1  0
  5  8  1  0
  7  9  1  0
  8 10  1  0
  9 11  1  0
 10 11  1  0
 10 12  2  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 13  1  0
  9 13  1  0
  8 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
 26 27  2  0
 26 28  1  0
 25 26  1  0
M  CHG  2  26   1  28  -1
M  END

Alternative Forms

1. Parent:

   

   ALA2207940

   5-[(2-Nitrophenyl)methyl]-2-phenyl-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: 390.46

Molecular Weight (Monoisotopic): 390.1038

AlogP: 5.37

#Rotatable Bonds: 4

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: 4.88

CX LogD: 4.88

Aromatic Rings: 3

Heavy Atoms: 28

QED Weighted: 0.44

Np Likeness Score: -1.23

References

1. Zhang P, Hu HR, Huang ZH, Lei JY, Chu Y, Ye DY..  (2012)  Identification of novel scaffold of benzothiazepinones as non-ATP competitive glycogen synthase kinase-3β inhibitors through virtual screening.,  22  (23): [PMID:23099099] [10.1016/j.bmcl.2012.09.043]

2. 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