8-(2,4-Difluoro-phenylamino)-5-oxo-10,11-dihydro-5H-dibenzo[a,d]cycloheptene-3-carboxylic acid(2,3-dihydroxy-propyl)-amide

ID: ALA2316479

PubChem CID: 71546184

Max Phase: Preclinical

Molecular Formula: C25H22F2N2O4

Molecular Weight: 452.46

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(NCC(O)CO)c1ccc2c(c1)C(=O)c1ccc(Nc3ccc(F)cc3F)cc1CC2

Standard InChI:  InChI=1S/C25H22F2N2O4/c26-17-5-8-23(22(27)11-17)29-18-6-7-20-15(9-18)3-1-14-2-4-16(10-21(14)24(20)32)25(33)28-12-19(31)13-30/h2,4-11,19,29-31H,1,3,12-13H2,(H,28,33)

Standard InChI Key:  NELOPHGKEYQQOV-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 33 36  0  0  0  0  0  0  0  0999 V2000
   15.1253   -0.7378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9521   -0.7636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4795   -2.5597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7675   -2.1794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5891   -1.3920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8194   -1.1544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2276   -1.7031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4105   -2.4925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1799   -2.7266    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4340   -1.4278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2057   -2.2534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8059   -2.8616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6346   -2.6457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8596   -1.8159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2578   -1.2112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4418   -3.3838    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.6571   -1.6046    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.2389   -2.1896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0198   -2.9840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6007   -3.5687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3992   -3.3576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6135   -2.5565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0310   -1.9752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9817   -3.9418    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   18.2218   -3.1933    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   12.8078   -3.0559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0185   -2.8156    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.9944   -3.8596    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.4159   -3.3791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6266   -3.1388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4400   -2.3351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6509   -2.0948    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0239   -3.7021    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  5  1  0
  1  2  1  0
 11  3  1  0
  3  4  1  0
  2 10  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9  4  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 10  1  0
  3 16  2  0
 14 17  1  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 18  1  0
 21 24  1  0
 19 25  1  0
  8 26  1  0
 26 27  1  0
 26 28  2  0
 27 29  1  0
 29 30  1  0
 30 31  1  0
 31 32  1  0
 30 33  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2316479

   13-(2,4-difluoroanilino)-N-(2,3-dihydroxypropyl)-2-oxotricyclo[9.4.0.03,8]pentadeca-1(11),3(8),4,6,12,14-hexaene-5-carboxamide

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: 452.46

Molecular Weight (Monoisotopic): 452.1548

AlogP: 3.12

#Rotatable Bonds: 6

Polar Surface Area: 98.66

Molecular Species: NEUTRAL

HBA: 5

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.90

CX Basic pKa: ┄

CX LogP: 3.47

CX LogD: 3.47

Aromatic Rings: 3

Heavy Atoms: 33

QED Weighted: 0.46

Np Likeness Score: -0.89

References

1. Fischer S, Wentsch HK, Mayer-Wrangowski SC, Zimmermann M, Bauer SM, Storch K, Niess R, Koeberle SC, Grütter C, Boeckler FM, Rauh D, Laufer SA..  (2013)  Dibenzosuberones as p38 mitogen-activated protein kinase inhibitors with low ATP competitiveness and outstanding whole blood activity.,  56  (1): [PMID:23270382] [10.1021/jm301539x]

2. 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