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

ID: ALA1259113

PubChem CID: 52942381

Max Phase: Preclinical

Molecular Formula: C20H25N3S

Molecular Weight: 339.51

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CN1CCN(C2Cc3ccccc3Sc3ccc(CN)cc32)CC1

Standard InChI:  InChI=1S/C20H25N3S/c1-22-8-10-23(11-9-22)18-13-16-4-2-3-5-19(16)24-20-7-6-15(14-21)12-17(18)20/h2-7,12,18H,8-11,13-14,21H2,1H3

Standard InChI Key:  JTFHPPAFIYXSHF-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 24 27  0  0  0  0  0  0  0  0999 V2000
   -1.6074   -6.0978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8033   -6.2989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6429   -7.9583    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2611   -7.4342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2716   -6.6344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9684   -6.2453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6552   -6.6550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6408   -7.4578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9434   -7.8433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4703   -7.0462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8648   -7.8088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4017   -8.5295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4557   -8.4889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8479   -7.7215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3826   -7.0039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7852   -5.2922    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1734   -4.7381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3485   -3.9356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1342   -3.6826    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7450   -4.2386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5702   -5.0475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3089   -2.8763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3762   -6.2540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0840   -6.6780    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  4  5  2  0
 11 12  1  0
  1  2  1  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  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
M  END

Alternative Forms

1. Parent:

   

   ALA1259113

   [5-(4-Methylpiperazin-1-yl)-5,6-dihydrobenzo[b][1]benzothiepin-3-yl]methanamine

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: 339.51

Molecular Weight (Monoisotopic): 339.1769

AlogP: 3.14

#Rotatable Bonds: 2

Polar Surface Area: 32.50

Molecular Species: BASE

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 9.24

CX LogP: 3.18

CX LogD: 0.69

Aromatic Rings: 2

Heavy Atoms: 24

QED Weighted: 0.91

Np Likeness Score: -0.34

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