2-Amino-6-bromo-4-(2-(3-methoxyphenyl)-2-oxoethyl)-4H-chromene-3-carbonitrile

ID: ALA4281455

PubChem CID: 145982409

Max Phase: Preclinical

Molecular Formula: C19H15BrN2O3

Molecular Weight: 399.24

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cccc(C(=O)CC2C(C#N)=C(N)Oc3ccc(Br)cc32)c1

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

Standard InChI Key:  XVJMYUVVURVVCI-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 25 27  0  0  0  0  0  0  0  0999 V2000
    3.6268   -5.5651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6257   -6.3923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3403   -6.8050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3384   -5.1525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0536   -5.5615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0571   -6.3898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7720   -6.7987    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4883   -6.3840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4849   -5.5556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7653   -5.1422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2037   -6.7943    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.7607   -4.3174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0442   -3.9090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0397   -3.0842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3322   -4.3252    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7523   -2.6700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7481   -1.8460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0310   -1.4367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3166   -1.8575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3243   -2.6801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1985   -5.1387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9103   -4.7194    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9124   -5.1529    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    6.4603   -1.4301    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1767   -1.8388    0.0000 C   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
  1 23  1  0
 17 24  1  0
 24 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4281455

   ---

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: 1.57

CX LogP: 3.39

CX LogD: 3.39

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.79

Np Likeness Score: -0.87

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