Methyl 2-amino-6-bromo-4-(2-(4-chlorophenyl)-2-oxoethyl)-8-methoxy-4H-chromene-3-carboxylate

ID: ALA4289734

PubChem CID: 145989515

Max Phase: Preclinical

Molecular Formula: C20H17BrClNO5

Molecular Weight: 466.71

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COC(=O)C1=C(N)Oc2c(OC)cc(Br)cc2C1CC(=O)c1ccc(Cl)cc1

Standard InChI:  InChI=1S/C20H17BrClNO5/c1-26-16-8-11(21)7-14-13(9-15(24)10-3-5-12(22)6-4-10)17(20(25)27-2)19(23)28-18(14)16/h3-8,13H,9,23H2,1-2H3

Standard InChI Key:  GAIJIIJTVYDRCS-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 28 30  0  0  0  0  0  0  0  0999 V2000
    3.9026   -6.2498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9015   -7.0771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6163   -7.4900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6145   -5.8370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3298   -6.2462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3332   -7.0747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0484   -7.4836    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7649   -7.0687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7614   -6.2403    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0416   -5.8267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4804   -7.4793    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.0371   -5.0017    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3204   -4.5932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3159   -3.7683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6082   -5.0096    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0286   -3.3540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0245   -2.5298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3072   -2.1203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5927   -2.5412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6003   -3.3641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4752   -5.8232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1909   -6.2334    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4726   -4.9982    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9041   -5.8188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6168   -8.3150    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9026   -8.7280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1881   -5.8375    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    5.3015   -1.2954    0.0000 Cl  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
 21 22  1  0
 21 23  2  0
  9 21  1  0
 22 24  1  0
  3 25  1  0
 25 26  1  0
  1 27  1  0
 18 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4289734

   ---

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: 466.71

Molecular Weight (Monoisotopic): 464.9979

AlogP: 4.20

#Rotatable Bonds: 5

Polar Surface Area: 87.85

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 4.15

CX LogD: 4.15

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.52

Np Likeness Score: -0.33

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