2-(1,1-Dioxido-2,3-dihydro-1,4-benzothiazepin-4(5H)-yl)-6-methyl-N-(piperidin-2-ylmethyl)quinolin-4-amine

ID: ALA4167039

PubChem CID: 145955448

Max Phase: Preclinical

Molecular Formula: C26H31FN4

Molecular Weight: 418.56

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1ccc2nc(N3CCCc4ccc(F)cc4C3)cc(NCC3CCCCN3)c2c1

Standard InChI:  InChI=1S/C26H31FN4/c1-18-7-10-24-23(13-18)25(29-16-22-6-2-3-11-28-22)15-26(30-24)31-12-4-5-19-8-9-21(27)14-20(19)17-31/h7-10,13-15,22,28H,2-6,11-12,16-17H2,1H3,(H,29,30)

Standard InChI Key:  QPQVDWJAVLAHGC-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 31 35  0  0  0  0  0  0  0  0999 V2000
   27.3963  -19.7308    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   28.1059  -19.3214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.1031  -18.4987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.3945  -18.0935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.6882  -19.3219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.6905  -18.5041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.9846  -18.0950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.2759  -18.5026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.2776  -19.3235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.9841  -19.7289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.8143  -19.7289    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   27.3910  -17.2763    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   28.0969  -16.8647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.8064  -17.2702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.5123  -16.8586    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   29.4822  -19.2688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.7513  -20.5442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.3535  -21.0987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.1617  -20.9714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.2629  -19.5062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.5695  -20.2646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.3779  -20.3770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.8805  -19.7319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.5690  -18.9722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.7615  -18.8634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.5681  -18.0941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.0686  -18.3255    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   30.2218  -17.2642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.8099  -18.0874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.5193  -18.4930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.2253  -18.0814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  5  1  1  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  6  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10  5  2  0
  2 11  1  0
  4 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 11 16  1  0
 16 20  1  0
 11 17  1  0
 17 18  1  0
 21 19  1  0
 18 19  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 20  1  0
  8 26  1  0
 24 27  1  0
 15 28  1  0
 14 29  1  0
 29 30  1  0
 28 31  1  0
 30 31  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4167039

   ---

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: 418.56

Molecular Weight (Monoisotopic): 418.2533

AlogP: 5.19

#Rotatable Bonds: 4

Polar Surface Area: 40.19

Molecular Species: BASE

HBA: 4

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 9.81

CX LogP: 5.72

CX LogD: 1.98

Aromatic Rings: 3

Heavy Atoms: 31

QED Weighted: 0.61

Np Likeness Score: -1.16

References

1. Zheng X, Liang C, Wang L, Wang B, Liu Y, Feng S, Wu JZ, Gao L, Feng L, Chen L, Guo T, Shen HC, Yun H..  (2018)  Discovery of Benzoazepinequinoline (BAQ) Derivatives as Novel, Potent, Orally Bioavailable Respiratory Syncytial Virus Fusion Inhibitors.,  61  (22): [PMID:30339388] [10.1021/acs.jmedchem.8b01394]

Source

Source(1):

• Scientific Literature