2-Amino-6-chloro-4-(4-cyanophenyl)-4H-benzo[h]chromene-3-carbonitrile

ID: ALA4558563

PubChem CID: 155557684

Max Phase: Preclinical

Molecular Formula: C21H12ClN3O

Molecular Weight: 357.80

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  N#CC1=C(N)Oc2c(cc(Cl)c3ccccc23)C1c1ccc(C#N)cc1

Standard InChI:  InChI=1S/C21H12ClN3O/c22-18-9-16-19(13-7-5-12(10-23)6-8-13)17(11-24)21(25)26-20(16)15-4-2-1-3-14(15)18/h1-9,19H,25H2

Standard InChI Key:  FINJHAQGTBPEME-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 26 29  0  0  0  0  0  0  0  0999 V2000
   13.5843  -11.4430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2923  -11.8519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5854  -10.6234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2895  -10.2158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2875   -9.4041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5821   -8.9991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8774   -9.4117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8829  -10.2221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9992  -10.6198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9980  -11.4405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7042  -11.8495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4161  -11.4425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4172  -10.6219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7065  -10.2083    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.1259  -10.2150    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.1220  -11.8479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8285  -12.2584    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.7005  -12.6637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9900  -13.0697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9874  -13.8861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6945  -14.2975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4057  -13.8865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4048  -13.0714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8762  -11.8510    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   15.6942  -15.1130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6930  -15.9301    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  2  0
  1  2  1  0
  2 10  2  0
  9  4  2  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  3  1  0
  9 10  1  0
  9 14  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 13 15  1  0
 16 17  3  0
 12 16  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
 11 18  1  0
  1 24  1  0
 25 26  3  0
 21 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4558563

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 357.80

Molecular Weight (Monoisotopic): 357.0669

AlogP: 4.58

#Rotatable Bonds: 1

Polar Surface Area: 82.83

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 1.68

CX LogP: 4.48

CX LogD: 4.48

Aromatic Rings: 3

Heavy Atoms: 26

QED Weighted: 0.69

Np Likeness Score: -1.02

References

1. Schmitt F, Gold M, Rothemund M, Andronache I, Biersack B, Schobert R, Mueller T..  (2019)  New naphthopyran analogues of LY290181 as potential tumor vascular-disrupting agents.,  163  [PMID:30503940] [10.1016/j.ejmech.2018.11.055]

Source

Source(1):

• Scientific Literature