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

ID: ALA1259190

PubChem CID: 49782998

Max Phase: Preclinical

Molecular Formula: C24H31N3OS

Molecular Weight: 409.60

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C24H31N3OS/c1-17(2)24(28)25-16-18-8-9-23-20(14-18)21(27-12-10-26(3)11-13-27)15-19-6-4-5-7-22(19)29-23/h4-9,14,17,21H,10-13,15-16H2,1-3H3,(H,25,28)/t21-/m0/s1

Standard InChI Key:  SHVCHMGRIYXVAY-NRFANRHFSA-N

Molfile:  

     RDKit          2D

 29 32  0  0  0  0  0  0  0  0999 V2000
    8.5509  -25.8811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3551  -26.0823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5154  -27.7417    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    7.8973  -27.2176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8867  -26.4177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1899  -26.0286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5031  -26.4383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5176  -27.2412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2149  -27.6266    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6880  -26.8296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2936  -27.5922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7566  -28.3129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6140  -28.2722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0062  -27.5048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5409  -26.7873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3731  -25.0755    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.9849  -24.5214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8098  -23.7189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0242  -23.4659    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.4133  -24.0219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5881  -24.8309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8494  -22.6597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7821  -26.0374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0744  -26.4613    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3550  -26.0604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6469  -26.4837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3425  -25.2355    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9262  -26.0820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6593  -27.3086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  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
 12 13  2  0
 26 28  1  0
  5  6  1  0
 26 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1259190

   2-methyl-N-[[(5S)-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: 409.60

Molecular Weight (Monoisotopic): 409.2188

AlogP: 3.95

#Rotatable Bonds: 4

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: 4.24

CX LogD: 3.52

Aromatic Rings: 2

Heavy Atoms: 29

QED Weighted: 0.83

Np Likeness Score: -0.67

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