N-[4-[(1-bromo-2-naphthyl)oxy]-3-chloro-phenyl]-2,3-dihydroxy-benzamide

ID: ALA4792789

PubChem CID: 162671491

Max Phase: Preclinical

Molecular Formula: C23H15BrClNO4

Molecular Weight: 484.73

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C(Nc1ccc(Oc2ccc3ccccc3c2Br)c(Cl)c1)c1cccc(O)c1O

Standard InChI:  InChI=1S/C23H15BrClNO4/c24-21-15-5-2-1-4-13(15)8-10-20(21)30-19-11-9-14(12-17(19)25)26-23(29)16-6-3-7-18(27)22(16)28/h1-12,27-28H,(H,26,29)

Standard InChI Key:  YSMVJDVCDPFJNK-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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   16.2986  -21.2354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0069  -20.8204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0022  -19.9942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2931  -19.5908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7203  -21.2304    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.4306  -20.8149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1412  -21.2293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8509  -20.8145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8482  -19.9923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1298  -19.5867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4230  -19.9997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1416  -22.0506    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   20.5579  -19.5801    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.2718  -19.9850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9815  -19.5727    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2761  -20.8063    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.6898  -19.9798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.3990  -19.5682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.3952  -18.7460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6762  -18.3371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9741  -18.7552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5832  -20.8222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5886  -20.0034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8861  -19.5916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1737  -19.9940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1683  -20.8128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8753  -21.2292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3012  -22.0526    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   22.6915  -20.7969    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.1081  -19.9743    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 22  1  1  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4 23  1  0
  2  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11  6  1  0
  7 12  1  0
  9 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  2  0
 15 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 15  1  0
 22 23  2  0
 22 27  1  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
  1 28  1  0
 17 29  1  0
 18 30  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4792789

   ---

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: 484.73

Molecular Weight (Monoisotopic): 482.9873

AlogP: 6.71

#Rotatable Bonds: 4

Polar Surface Area: 78.79

Molecular Species: NEUTRAL

HBA: 4

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 5

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 8.08

CX Basic pKa: ┄

CX LogP: 6.32

CX LogD: 6.24

Aromatic Rings: 4

Heavy Atoms: 30

QED Weighted: 0.28

Np Likeness Score: -0.80

References

1. Fujii S,Kikuchi E,Watanabe Y,Suzuyama H,Ishigami-Yuasa M,Mori T,Isobe K,Uchida S,Kagechika H.  (2020)  Structural development of N-(4-phenoxyphenyl)benzamide derivatives as novel SPAK inhibitors blocking WNK kinase signaling.,  30  (17): [PMID:32738993] [10.1016/j.bmcl.2020.127408]

Source

Source(1):

• Scientific Literature