2-Amino-6-bromo-8-methoxy-4-(2-oxo-2-phenylethyl)-4H-chromene-3-carbonitrile

ID: ALA4292415

PubChem CID: 145988317

Max Phase: Preclinical

Molecular Formula: C19H15BrN2O3

Molecular Weight: 399.24

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc(Br)cc2c1OC(N)=C(C#N)C2CC(=O)c1ccccc1

Standard InChI:  InChI=1S/C19H15BrN2O3/c1-24-17-8-12(20)7-14-13(15(10-21)19(22)25-18(14)17)9-16(23)11-5-3-2-4-6-11/h2-8,13H,9,22H2,1H3

Standard InChI Key:  WHUYDJLEDNUYMJ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 25 27  0  0  0  0  0  0  0  0999 V2000
   19.8711  -21.5470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8699  -22.3741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5846  -22.7868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5827  -21.1344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2979  -21.5433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3013  -22.3716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0162  -22.7804    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.7325  -22.3656    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.7290  -21.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0095  -21.1240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.4478  -22.7761    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.0049  -20.2993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2885  -19.8908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2839  -19.0662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5765  -20.3071    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.9965  -18.6520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9923  -17.8281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2753  -17.4188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5609  -17.8395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5686  -18.6621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.4426  -21.1205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.1544  -20.7013    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.5851  -23.6115    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.8711  -24.0244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1568  -21.1348    0.0000 Br  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
  8  9  2  0
  9 10  1  0
  8 11  1  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  2  0
 14 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 14  1  0
  9 21  1  0
 21 22  3  0
  3 23  1  0
 23 24  1  0
  1 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4292415

   ---

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: 399.24

Molecular Weight (Monoisotopic): 398.0266

AlogP: 3.90

#Rotatable Bonds: 4

Polar Surface Area: 85.34

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 1.45

CX LogP: 3.39

CX LogD: 3.39

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.79

Np Likeness Score: -0.50

References

1. Pontes O, Costa M, Santos F, Sampaio-Marques B, Dias T, Ludovico P, Baltazar F, Proença F..  (2018)  Exploitation of new chalcones and 4H-chromenes as agents for cancer treatment.,  157  [PMID:30081238] [10.1016/j.ejmech.2018.07.058]

Source

Source(1):

• Scientific Literature