4-Amino-N-(3-{2-[(4-oxo-4H-chromen-7-yl)oxy]-acetamido}phenyl)benzamide

ID: ALA4475912

PubChem CID: 155537848

Max Phase: Preclinical

Molecular Formula: C24H19N3O5

Molecular Weight: 429.43

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Nc1ccc(C(=O)Nc2cccc(NC(=O)COc3ccc4c(=O)ccoc4c3)c2)cc1

Standard InChI:  InChI=1S/C24H19N3O5/c25-16-6-4-15(5-7-16)24(30)27-18-3-1-2-17(12-18)26-23(29)14-32-19-8-9-20-21(28)10-11-31-22(20)13-19/h1-13H,14,25H2,(H,26,29)(H,27,30)

Standard InChI Key:  TUXYVYLWAGBIGZ-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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    6.0048  -14.4447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0048  -15.2692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2965  -15.6766    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5879  -15.2698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    5.2939  -14.0391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8798  -14.0381    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.7129  -15.6768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7129  -16.4963    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4210  -15.2692    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.1331  -15.6768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1331  -16.4969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8437  -16.9023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5453  -16.4957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5453  -15.6762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2575  -15.2686    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.9656  -15.6762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9656  -16.4957    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   12.3818  -15.6762    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.0939  -15.2686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8022  -15.6788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5104  -15.2656    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2188  -15.6725    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.9206  -15.2618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9206  -14.4481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2142  -14.0412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2142  -13.2217    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.5104  -14.4520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7998  -14.0400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0939  -14.4491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8411  -15.2696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  2  0
  4  3  1  0
  5  4  2  0
  6  5  1  0
  1  6  2  0
  5  7  1  0
  8  2  1  0
  8  9  2  0
 10  8  1  0
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 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 29 27  1  0
 23 29  1  0
 29 30  2  0
 30 31  1  0
 31 21  2  0
 15 32  1  0
 32 11  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4475912

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 429.43

Molecular Weight (Monoisotopic): 429.1325

AlogP: 3.65

#Rotatable Bonds: 6

Polar Surface Area: 123.66

Molecular Species: NEUTRAL

HBA: 6

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.48

CX Basic pKa: 2.81

CX LogP: 2.69

CX LogD: 2.69

Aromatic Rings: 4

Heavy Atoms: 32

QED Weighted: 0.40

Np Likeness Score: -0.97

References

1. Zhao L, Li Y, Wang Y, Qiao Z, Miao Z, Yang J, Huang L, Tian C, Li L, Chen D, Yang S..  (2019)  Discovery of 4H-Chromen-4-one Derivatives as a New Class of Selective Rho Kinase (ROCK) Inhibitors, which Showed Potent Activity in ex Vivo Diabetic Retinopathy Models.,  62  (23): [PMID:31693351] [10.1021/acs.jmedchem.9b01143]

Source

Source(1):

• Scientific Literature