1-(4-nitrobenzyl)-5-(2-oxo-2H-chromen-6-yl)-1H-pyrrole-2-carbonitrile

ID: ALA3975442

PubChem CID: 134152665

Max Phase: Preclinical

Molecular Formula: C21H13N3O4

Molecular Weight: 371.35

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  N#Cc1ccc(-c2ccc3oc(=O)ccc3c2)n1Cc1ccc([N+](=O)[O-])cc1

Standard InChI:  InChI=1S/C21H13N3O4/c22-12-18-7-8-19(15-3-9-20-16(11-15)4-10-21(25)28-20)23(18)13-14-1-5-17(6-2-14)24(26)27/h1-11H,13H2

Standard InChI Key:  YWFKGEUMVYHGIM-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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    9.4045  -18.2382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4034  -19.0577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1114  -19.4667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1096  -17.8293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8183  -18.2346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8217  -19.0598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5340  -19.4672    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.2476  -19.0539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2442  -18.2287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5273  -17.8168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9564  -19.4606    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7012  -17.8301    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6154  -17.0178    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.8162  -16.8477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4077  -17.5555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9548  -18.1626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4873  -16.1007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1548  -15.3542    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.3221  -16.6075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3202  -15.7903    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0265  -15.3846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0250  -14.5682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3158  -14.1604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6067  -14.5750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6117  -15.3901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3133  -13.3384    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.6041  -12.9324    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0195  -12.9272    0.0000 O   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
  5 10  1  0
  6  7  1  0
  7  8  1  0
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  9 10  2  0
  8 11  2  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 12  2  0
  1 12  1  0
 17 18  3  0
 14 17  1  0
 13 19  1  0
 19 20  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
 26 27  2  0
 26 28  1  0
 23 26  1  0
M  CHG  2  26   1  28  -1
M  END

Alternative Forms

1. Parent:

   

   ALA3975442

   ---

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: 371.35

Molecular Weight (Monoisotopic): 371.0906

AlogP: 4.09

#Rotatable Bonds: 4

Polar Surface Area: 102.07

Molecular Species: ┄

HBA: 6

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 4.09

CX LogD: 4.09

Aromatic Rings: 4

Heavy Atoms: 28

QED Weighted: 0.31

Np Likeness Score: -0.86

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