2-Amino-6-bromo-8-methoxy-4-(2-(3-methoxyphenyl)-2-oxoethyl)-4H-chromene-3-carbonitrile

ID: ALA4287063

PubChem CID: 145990454

Max Phase: Preclinical

Molecular Formula: C20H17BrN2O4

Molecular Weight: 429.27

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cccc(C(=O)CC2C(C#N)=C(N)Oc3c(OC)cc(Br)cc32)c1

Standard InChI:  InChI=1S/C20H17BrN2O4/c1-25-13-5-3-4-11(6-13)17(24)9-14-15-7-12(21)8-18(26-2)19(15)27-20(23)16(14)10-22/h3-8,14H,9,23H2,1-2H3

Standard InChI Key:  IDUWPNGPJLPBOS-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   29.2139  -13.0869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.2128  -13.9142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.9275  -14.3271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.9257  -12.6741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.6410  -13.0832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.6445  -13.9116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.3597  -14.3207    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.0760  -13.9058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.0726  -13.0774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.3528  -12.6638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.7916  -14.3164    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   31.3483  -11.8388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.6316  -11.4303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.6271  -10.6053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.9194  -11.8467    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.3398  -10.1911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.3357   -9.3668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.6184   -8.9575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.9039   -9.3783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.9117  -10.2012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.7863  -12.6603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.4983  -12.2410    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   29.9280  -15.1520    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.2139  -15.5649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.4994  -12.6746    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   32.0481   -8.9508    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.7645   -9.3598    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
  3 23  1  0
 23 24  1  0
  1 25  1  0
 17 26  1  0
 26 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4287063

   ---

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: 429.27

Molecular Weight (Monoisotopic): 428.0372

AlogP: 3.91

#Rotatable Bonds: 5

Polar Surface Area: 94.57

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 1.45

CX LogP: 3.23

CX LogD: 3.23

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.72

Np Likeness Score: -0.62

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