1-(3,5-difluorobenzyl)-5-(2-oxo-2H-chromen-6-yl)-1H-pyrrole-2-carbonitrile

ID: ALA3983437

PubChem CID: 134157750

Max Phase: Preclinical

Molecular Formula: C21H12F2N2O2

Molecular Weight: 362.33

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  N#Cc1ccc(-c2ccc3oc(=O)ccc3c2)n1Cc1cc(F)cc(F)c1

Standard InChI:  InChI=1S/C21H12F2N2O2/c22-16-7-13(8-17(23)10-16)12-25-18(11-24)3-4-19(25)14-1-5-20-15(9-14)2-6-21(26)27-20/h1-10H,12H2

Standard InChI Key:  NIDQVGMQJYGJEB-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   20.8399  -18.9339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5480  -19.3429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5462  -17.7055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2548  -18.1108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2582  -18.9360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9706  -19.3434    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.6841  -18.9301    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.6808  -18.1049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9638  -17.6930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.3930  -19.3368    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.1378  -17.7062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0519  -16.8940    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.2527  -16.7238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8443  -17.4317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3913  -18.0388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9239  -15.9769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5913  -15.2304    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.7587  -16.4837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7568  -15.6665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4631  -15.2608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4615  -14.4444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7523  -14.0366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0433  -14.4512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0483  -15.2663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1685  -14.0345    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   19.3332  -14.0468    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  6  2  0
  5  4  2  0
  4  1  1  0
  5  6  1  0
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  6  7  1  0
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  8 11  2  0
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  1 12  1  0
 17 18  3  0
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 20 21  2  0
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 23 24  1  0
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 24 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3983437

   ---

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: 362.33

Molecular Weight (Monoisotopic): 362.0867

AlogP: 4.46

#Rotatable Bonds: 3

Polar Surface Area: 58.93

Molecular Species: ┄

HBA: 4

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 4.44

CX LogD: 4.44

Aromatic Rings: 4

Heavy Atoms: 27

QED Weighted: 0.51

Np Likeness Score: -0.84

References

1. Kinoshita M, Negishi M, Sakai H, Hirano T, Mori S, Fujii S, Kagechika H, Tanatani A..  (2016)  Development of 6-arylcoumarins as nonsteroidal progesterone antagonists. Structure-activity relationships and fluorescence properties.,  24  (21): [PMID:27665178] [10.1016/j.bmc.2016.09.020]

Source

Source(1):

• Scientific Literature