(S)-N-((11-(4-methylpiperazin-1-yl)-10,11-dihydrodibenzo[b,f]thiepin-2-yl)methyl)acetamide

ID: ALA1259174

PubChem CID: 49782792

Max Phase: Preclinical

Molecular Formula: C22H27N3OS

Molecular Weight: 381.55

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(=O)NCc1ccc2c(c1)[C@@H](N1CCN(C)CC1)Cc1ccccc1S2

Standard InChI:  InChI=1S/C22H27N3OS/c1-16(26)23-15-17-7-8-22-19(13-17)20(25-11-9-24(2)10-12-25)14-18-5-3-4-6-21(18)27-22/h3-8,13,20H,9-12,14-15H2,1-2H3,(H,23,26)/t20-/m0/s1

Standard InChI Key:  YBCFDDCJLZVHPZ-FQEVSTJZSA-N

Molfile:  

     RDKit          2D

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   21.2551  -19.2311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0592  -19.4323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2196  -21.0917    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   20.6014  -20.5676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5909  -19.7677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8941  -19.3786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2073  -19.7883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2217  -20.5912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9191  -20.9766    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3922  -20.1796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9977  -20.9422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4608  -21.6629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.3182  -21.6222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.7104  -20.8548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.2451  -20.1373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0773  -18.4255    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.6891  -17.8714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5140  -17.0689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7283  -16.8159    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.1175  -17.3719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2923  -18.1809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5536  -16.0097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4863  -19.3874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7785  -19.8113    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.0592  -19.4104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3510  -19.8337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0467  -18.5855    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 12 13  2  0
  5  6  1  0
 13 14  1  0
 11  3  1  0
 14 15  2  0
 15 10  1  0
  6  7  2  0
  1 16  1  1
 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
M  END

Alternative Forms

1. Parent:

   

   ALA1259174

   N-[[(5S)-5-(4-methylpiperazin-1-yl)-5,6-dihydrobenzo[b][1]benzothiepin-3-yl]methyl]acetamide

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: 381.55

Molecular Weight (Monoisotopic): 381.1875

AlogP: 3.32

#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: 2.99

CX LogD: 2.28

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.88

Np Likeness Score: -0.64

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