5-bromo-N-(2,3-dihydroxypropoxy)-2-((2,4-dimethylphenyl)amino)-3,4-dimethylbenzamide

ID: ALA5290294

Max Phase: Preclinical

Molecular Formula: C20H25BrN2O4

Molecular Weight: 437.33

Names and Identifiers

Canonical SMILES:  Cc1ccc(Nc2c(C(=O)NOCC(O)CO)cc(Br)c(C)c2C)c(C)c1

Standard InChI:  InChI=1S/C20H25BrN2O4/c1-11-5-6-18(12(2)7-11)22-19-14(4)13(3)17(21)8-16(19)20(26)23-27-10-15(25)9-24/h5-8,15,22,24-25H,9-10H2,1-4H3,(H,23,26)

Standard InChI Key:  AFFQWGYHTUODJN-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 27 28  0  0  0  0  0  0  0  0999 V2000
   -2.8450   -0.8210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8450   -1.6460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1316   -2.0523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4246   -1.6423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4246   -0.8206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1334   -0.4104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1334    0.4112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7129   -0.4097    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7129    0.4119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4237    0.8229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4237    1.6422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7119    2.0531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0017    1.6457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0017    0.8245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7132    0.4136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7119    2.8749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7129   -2.0531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0013   -1.6423    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7102   -2.0531    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4218   -1.6423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1334   -2.0531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8450   -1.6423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5566   -2.0531    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1334   -2.8749    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7129   -2.8749    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5566   -2.0568    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -3.5566   -0.4102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  1  2  0
  6  7  1  0
  5  8  1  0
  8  9  1  0
 10  9  2  0
 11 10  1  0
 12 11  2  0
 13 12  1  0
 14 13  2  0
  9 14  1  0
 14 15  1  0
 12 16  1  0
  4 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 21 24  1  0
 17 25  2  0
  2 26  1  0
  1 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5290294

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type:

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 437.33

Molecular Weight (Monoisotopic): 436.0998

AlogP: 3.44

#Rotatable Bonds: 7

Polar Surface Area: 90.82

Molecular Species: NEUTRAL

HBA: 5

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.70

CX Basic pKa: ┄

CX LogP: 5.44

CX LogD: 5.44

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.50

Np Likeness Score: -0.73

References

1. Phull MS, Jadav SS, Gundla R, Mainkar PS..  (2021)  A perspective on medicinal chemistry approaches towards adenomatous polyposis coli and Wnt signal based colorectal cancer inhibitors.,  212  [PMID:33445154] [10.1016/j.ejmech.2020.113149]

Source

Source(1):

• Scientific Literature