N-((11-(4-Methylpiperazin-1-yl)-10,11-dihydrodibenzo[b,f]thiepin-2-yl)methyl)pivalamide

ID: ALA1259158

PubChem CID: 49781894

Max Phase: Preclinical

Molecular Formula: C25H33N3OS

Molecular Weight: 423.63

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CN1CCN(C2Cc3ccccc3Sc3ccc(CNC(=O)C(C)(C)C)cc32)CC1

Standard InChI:  InChI=1S/C25H33N3OS/c1-25(2,3)24(29)26-17-18-9-10-23-20(15-18)21(28-13-11-27(4)12-14-28)16-19-7-5-6-8-22(19)30-23/h5-10,15,21H,11-14,16-17H2,1-4H3,(H,26,29)

Standard InChI Key:  CKLAPTDGXNWXQT-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 30 33  0  0  0  0  0  0  0  0999 V2000
   18.2259  -13.1978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0301  -13.3989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1904  -15.0583    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   17.5723  -14.5342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5617  -13.7344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8649  -13.3453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1781  -13.7550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1926  -14.5578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8899  -14.9433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3630  -14.1462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9686  -14.9088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4316  -15.6295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2890  -15.5889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6812  -14.8215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2159  -14.1039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0481  -12.3922    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.6599  -11.8381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4848  -11.0356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6992  -10.7826    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.0883  -11.3386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2631  -12.1475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5244   -9.9763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4571  -13.3540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7494  -13.7780    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.0300  -13.3771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3219  -13.8003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0175  -12.5522    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.6012  -13.3987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3343  -14.6252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6042  -14.2083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 11  3  1  0
 14 15  2  0
 15 10  1  0
  6  7  2  0
  1 16  1  0
 16 17  1  0
  3  4  1  0
  7  8  1  0
  2 10  1  0
  8  9  2  0
  9  4  1  0
 16 21  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 19 22  1  0
  1  5  1  0
  7 23  1  0
 10 11  2  0
 23 24  1  0
  4  5  2  0
 24 25  1  0
 11 12  1  0
 25 26  1  0
  1  2  1  0
 25 27  2  0
 12 13  2  0
 26 28  1  0
  5  6  1  0
 26 29  1  0
 13 14  1  0
 26 30  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1259158

   2,2-dimethyl-N-[[5-(4-methylpiperazin-1-yl)-5,6-dihydrobenzo[b][1]benzothiepin-3-yl]methyl]propanamide

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: 423.63

Molecular Weight (Monoisotopic): 423.2344

AlogP: 4.34

#Rotatable Bonds: 3

Polar Surface Area: 35.58

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 8.03

CX LogP: 4.79

CX LogD: 4.08

Aromatic Rings: 2

Heavy Atoms: 30

QED Weighted: 0.80

Np Likeness Score: -0.74

References

1. Kristensen JL, Püschl A, Jensen M, Risgaard R, Christoffersen CT, Bang-Andersen B, Balle T..  (2010)  Exploring the neuroleptic substituent in octoclothepin: potential ligands for positron emission tomography with subnanomolar affinity for α(1)-adrenoceptors.,  53  (19): [PMID:20857909] [10.1021/jm100652h]

Source

Source(1):

• Scientific Literature