1-(4-(pyridin-2-ylmethoxy)-3-(2,3,4,5-tetrahydro-1H-benzo[d]azepin-7-yl)phenyl)ethanone

ID: ALA4280620

PubChem CID: 70665386

Max Phase: Preclinical

Molecular Formula: C24H24N2O2

Molecular Weight: 372.47

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(=O)c1ccc(OCc2ccccn2)c(-c2ccc3c(c2)CCNCC3)c1

Standard InChI:  InChI=1S/C24H24N2O2/c1-17(27)19-7-8-24(28-16-22-4-2-3-11-26-22)23(15-19)21-6-5-18-9-12-25-13-10-20(18)14-21/h2-8,11,14-15,25H,9-10,12-13,16H2,1H3

Standard InChI Key:  SMCVDPXIAQLLPB-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 28 31  0  0  0  0  0  0  0  0999 V2000
    1.1212  -27.1654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1200  -27.9849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8281  -28.3939    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5377  -27.9844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5349  -27.1618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8263  -26.7565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2461  -28.3919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9532  -27.9822    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6615  -28.3897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6582  -29.2053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3657  -29.6128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0737  -29.2030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0698  -28.3816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3617  -27.9779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3534  -27.1629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0599  -26.7502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6365  -25.9469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6452  -26.7619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7826  -29.6095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7850  -30.4267    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4891  -29.1989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0525  -25.9326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3448  -25.5308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2141  -24.7218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8123  -25.6259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7606  -24.1156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0453  -24.8408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5752  -24.1708    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  1  1  0
  4  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14  9  1  0
 15 16  2  0
 16 22  1  0
 23 17  1  0
 17 18  2  0
 18 15  1  0
 14 15  1  0
 12 19  1  0
 19 20  2  0
 19 21  1  0
 22 23  2  0
 23 24  1  0
 22 25  1  0
 24 26  1  0
 25 27  1  0
 26 28  1  0
 27 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4280620

   1-[4-(pyridin-2-ylmethoxy)-3-(2,3,4,5-tetrahydro-1H-3-benzazepin-7-yl)phenyl]ethanone

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: 372.47

Molecular Weight (Monoisotopic): 372.1838

AlogP: 4.22

#Rotatable Bonds: 5

Polar Surface Area: 51.22

Molecular Species: BASE

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 9.92

CX LogP: 3.50

CX LogD: 1.05

Aromatic Rings: 3

Heavy Atoms: 28

QED Weighted: 0.68

Np Likeness Score: -0.84

References

1. Barker MD, Liddle J, Atkinson FL, Wilson DM, Dickson MC, Ramirez-Molina C, Lewis H, Davis RP, Somers DO, Neu M, Jones E, Watson R..  (2018)  Discovery of potent and selective Spleen Tyrosine Kinase inhibitors for the topical treatment of inflammatory skin disease.,  28  (21): [PMID:30249354] [10.1016/j.bmcl.2018.09.022]

Source

Source(1):

• Scientific Literature