7-((6-(4-chlorophenyl)pyridin-3-ylsulfonyl)methyl)-2,3,4,5-tetrahydro-1H-benzo[d]azepine

ID: ALA1078267

PubChem CID: 46882752

Max Phase: Preclinical

Molecular Formula: C22H21ClN2O2S

Molecular Weight: 412.94

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=S(=O)(Cc1ccc2c(c1)CCNCC2)c1ccc(-c2ccc(Cl)cc2)nc1

Standard InChI:  InChI=1S/C22H21ClN2O2S/c23-20-5-3-18(4-6-20)22-8-7-21(14-25-22)28(26,27)15-16-1-2-17-9-11-24-12-10-19(17)13-16/h1-8,13-14,24H,9-12,15H2

Standard InChI Key:  RVCJMLBYBBJSCR-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   10.5624   -9.8185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8495  -10.2345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8543  -11.0624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5701  -11.4681    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.2831  -11.0493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9912   -9.8102    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   12.7124   -7.7449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7111   -8.5689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4294   -8.9822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4274   -7.3315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9405   -8.1609    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.5850   -7.4139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7821   -7.2305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5828   -8.9010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7789   -9.0839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1381   -8.5665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1372   -7.7410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9907   -8.9852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7002   -9.3920    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.3972  -10.5207    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.1419  -11.4802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4255  -11.0678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7138  -11.4849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7191  -12.3117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4419  -12.7196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1509  -12.2999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0072  -12.7306    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  8  9  2  0
  4  5  1  0
 12 13  1  0
 13 14  1  0
 12 15  1  0
 16 17  1  0
 17 18  1  0
 18 14  1  0
 15 16  1  0
  9 10  1  0
  9 19  1  0
 19  7  1  0
  7  1  1  0
 10 17  2  0
  7 20  2  0
  2  3  1  0
  7 21  2  0
 18 11  2  0
  4 22  1  0
 11  8  1  0
 22 23  2  0
  5  6  2  0
 23 24  1  0
  6  1  1  0
 24 25  2  0
  1  2  2  0
 25 26  1  0
  3  4  2  0
 26 27  2  0
 27 22  1  0
 25 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1078267

   7-[[6-(4-chlorophenyl)pyridin-3-yl]sulfonylmethyl]-2,3,4,5-tetrahydro-1H-3-benzazepine

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: 412.94

Molecular Weight (Monoisotopic): 412.1012

AlogP: 4.06

#Rotatable Bonds: 4

Polar Surface Area: 59.06

Molecular Species: BASE

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 9.86

CX LogP: 4.00

CX LogD: 1.60

Aromatic Rings: 3

Heavy Atoms: 28

QED Weighted: 0.70

Np Likeness Score: -1.24

References

1. Bailey JM, Scott JS, Basilla JB, Bolton VJ, Boyfield I, Evans DG, Fleury E, Heightman TD, Jarvie EM, Lawless K, Matthews KL, McKay F, Mok H, Muir A, Orlek BS, Sanger GJ, Stemp G, Stevens AJ, Thompson M, Ward J, Vaidya K, Westaway SM..  (2009)  The discovery and optimisation of benzazepine sulfonamide and sulfones as potent agonists of the motilin receptor.,  19  (22): [PMID:19804969] [10.1016/j.bmcl.2009.09.027]

Source

Source(1):

• Scientific Literature