3-chloro-1-(phenylsulfonyl)-1,5,6,7,8,9-hexahydroazepino[4,5-f]indole

ID: ALA515624

PubChem CID: 25110703

Max Phase: Preclinical

Molecular Formula: C18H17ClN2O2S

Molecular Weight: 360.87

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=S(=O)(c1ccccc1)n1cc(Cl)c2cc3c(cc21)CCNCC3

Standard InChI:  InChI=1S/C18H17ClN2O2S/c19-17-12-21(24(22,23)15-4-2-1-3-5-15)18-11-14-7-9-20-8-6-13(14)10-16(17)18/h1-5,10-12,20H,6-9H2

Standard InChI Key:  KVICYPUXGNRQCI-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 24 27  0  0  0  0  0  0  0  0999 V2000
    7.9670   -7.4188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9670   -9.0688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6815   -7.8313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6815   -8.6563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3265   -9.1707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3265   -7.3170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1308   -8.9871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1308   -7.5005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4888   -8.2438    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.2526   -7.8313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2526   -8.6563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4679   -8.9113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9830   -8.2438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4679   -7.5764    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.2130   -6.7918    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.9581   -6.0071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9976   -6.5368    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4284   -7.0467    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1511   -5.8356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8961   -5.0510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4482   -4.4379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2552   -4.6094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5101   -5.3941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2130   -9.6959    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  4  5  1  0
  4  2  2  0
  3  6  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 10  1  0
  2 11  1  0
 14 15  1  0
  5  7  1  0
 15 16  1  0
 10  1  1  0
 15 17  2  0
  6  8  1  0
 15 18  2  0
  1  3  2  0
 16 19  2  0
  7  9  1  0
 19 20  1  0
  8  9  1  0
 20 21  2  0
 10 11  2  0
 21 22  1  0
  3  4  1  0
 22 23  2  0
 23 16  1  0
 12 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA515624

   3-Chloro-1-(phenylsulfonyl)-1,5,6,7,8,9-hexahydroazepino[4,5-f]indole

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: 360.87

Molecular Weight (Monoisotopic): 360.0699

AlogP: 3.22

#Rotatable Bonds: 2

Polar Surface Area: 51.10

Molecular Species: BASE

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 9.93

CX LogP: 3.49

CX LogD: 1.04

Aromatic Rings: 3

Heavy Atoms: 24

QED Weighted: 0.76

Np Likeness Score: -0.88

References

1. Trani G, Baddeley SM, Briggs MA, Chuang TT, Deeks NJ, Johnson CN, Khazragi AA, Mead TL, Medhurst AD, Milner PH, Quinn LP, Ray AM, Rivers DA, Stean TO, Stemp G, Trail BK, Witty DR..  (2008)  Tricyclic azepine derivatives as selective brain penetrant 5-HT6 receptor antagonists.,  18  (20): [PMID:18793848] [10.1016/j.bmcl.2008.08.010]

Source

Source(1):

• Scientific Literature