N-[2-Fluoro-5-(5-oxo-6,7,8,9-tetrahydro-5H-benzocyclohepten-2-ylamino)-phenyl]-benzamide

ID: ALA2177219

PubChem CID: 66557865

Max Phase: Preclinical

Molecular Formula: C24H21FN2O2

Molecular Weight: 388.44

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(Nc1cc(Nc2ccc3c(c2)CCCCC3=O)ccc1F)c1ccccc1

Standard InChI:  InChI=1S/C24H21FN2O2/c25-21-13-11-19(15-22(21)27-24(29)16-6-2-1-3-7-16)26-18-10-12-20-17(14-18)8-4-5-9-23(20)28/h1-3,6-7,10-15,26H,4-5,8-9H2,(H,27,29)

Standard InChI Key:  ATBLOTYVKHVLPU-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 29 32  0  0  0  0  0  0  0  0999 V2000
    9.6908   -8.3382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4070   -8.7478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4104   -9.5728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1265   -9.9824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8393   -9.5669    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8359   -8.7419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1198   -8.3324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6875   -7.5132    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9781   -8.7536    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.2619   -8.3440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5491   -8.7595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8330   -8.3499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8296   -7.5249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5424   -7.1095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2585   -7.5190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1202   -8.7653    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9718   -7.5366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9751   -8.3615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3286   -8.8935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5308   -8.6833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1662   -7.9564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5251   -7.2266    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3206   -7.0099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6913   -8.7711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4041   -8.3557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4007   -7.5307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6845   -7.1211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5274   -6.2253    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9713   -7.1036    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  2  7  2  0
  1  8  2  0
  1  9  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 10 15  2  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 17 23  1  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 17 27  2  0
 18 24  2  0
 23 28  2  0
 16 25  1  0
 12 16  1  0
  9 10  1  0
 15 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2177219

   N-{2-Fluoro-5-[(5-Oxo-6,7,8,9-Tetrahydro-5h-Benzo[7]annulen-2-Yl)amino]phenyl}benzamide

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: 388.44

Molecular Weight (Monoisotopic): 388.1587

AlogP: 5.73

#Rotatable Bonds: 4

Polar Surface Area: 58.20

Molecular Species: NEUTRAL

HBA: 3

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 5.40

CX LogD: 5.40

Aromatic Rings: 3

Heavy Atoms: 29

QED Weighted: 0.56

Np Likeness Score: -1.23

References

1. Martz KE, Dorn A, Baur B, Schattel V, Goettert MI, Mayer-Wrangowski SC, Rauh D, Laufer SA..  (2012)  Targeting the hinge glycine flip and the activation loop: novel approach to potent p38α inhibitors.,  55  (17): [PMID:22897496] [10.1021/jm300951u]

2. Astolfi A, Kudolo M, Brea J, Manni G, Manfroni G, Palazzotti D, Sabatini S, Cecchetti F, Felicetti T, Cannalire R, Massari S, Tabarrini O, Loza MI, Fallarino F, Cecchetti V, Laufer SA, Barreca ML..  (2019)  Discovery of potent p38α MAPK inhibitors through a funnel like workflow combining in silico screening and in vitro validation.,  182  [PMID:31445234] [10.1016/j.ejmech.2019.111624]

3. Carrillo García C, Becker C, Forster M, Lohmann S, Freitag P, Laufer S, Sievers S, Fleischmann BK, Hesse M, Schade D..  (2022)  High-Throughput Screening Platform in Postnatal Heart Cells and Chemical Probe Toolbox to Assess Cardiomyocyte Proliferation.,  65  (2.0): [PMID:34818008] [10.1021/acs.jmedchem.1c01173]

Source

Source(1):

• Scientific Literature