7-((4-tert-butylphenylsulfonyl)methyl)-2,3,4,5-tetrahydro-1H-benzo[d]azepine

ID: ALA1078342

PubChem CID: 46882710

Max Phase: Preclinical

Molecular Formula: C21H27NO2S

Molecular Weight: 357.52

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)(C)c1ccc(S(=O)(=O)Cc2ccc3c(c2)CCNCC3)cc1

Standard InChI:  InChI=1S/C21H27NO2S/c1-21(2,3)19-6-8-20(9-7-19)25(23,24)15-16-4-5-17-10-12-22-13-11-18(17)14-16/h4-9,14,22H,10-13,15H2,1-3H3

Standard InChI Key:  VSEFZWVBYMRIEE-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 25 27  0  0  0  0  0  0  0  0999 V2000
    2.7623    0.4353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0458    0.8441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3332    0.4284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3379   -0.3992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0535   -0.8048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7663   -0.3860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4740    0.8526    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.1949    2.9169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1936    2.0933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9115    1.6802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9096    3.3299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4215    2.5010    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.0661    3.2476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2635    3.4310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0640    1.7613    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2603    1.5784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6201    2.0956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6191    2.9209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4735    1.6770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1827    1.2704    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8800    0.1422    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6259   -0.8168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0919   -0.4090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6316   -1.6424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0917   -1.2245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  3  4  2  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  1  0
  5  6  2  0
 22 24  1  0
  6  1  1  0
 22 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1078342

   7-[(4-tert-butylphenyl)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: 357.52

Molecular Weight (Monoisotopic): 357.1763

AlogP: 3.65

#Rotatable Bonds: 3

Polar Surface Area: 46.17

Molecular Species: BASE

HBA: 3

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 9.86

CX LogP: 4.12

CX LogD: 1.73

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.91

Np Likeness Score: -1.09

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