N-Hydroxy-4-(2-benzyloxyacridin-9-ylamino)benzamide

ID: ALA4761847

PubChem CID: 162659066

Max Phase: Preclinical

Molecular Formula: C27H21N3O3

Molecular Weight: 435.48

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C(NO)c1ccc(Nc2c3ccccc3nc3ccc(OCc4ccccc4)cc23)cc1

Standard InChI:  InChI=1S/C27H21N3O3/c31-27(30-32)19-10-12-20(13-11-19)28-26-22-8-4-5-9-24(22)29-25-15-14-21(16-23(25)26)33-17-18-6-2-1-3-7-18/h1-16,32H,17H2,(H,28,29)(H,30,31)

Standard InChI Key:  QJZZSSBITISGGT-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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    9.4342  -16.2984    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4318  -15.4812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1383  -15.0706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    9.4390  -18.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1443  -19.1545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1443  -17.5201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8495  -17.9328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8506  -18.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5549  -19.1554    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.5528  -17.5211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2616  -17.9310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   11.5506  -16.7039    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.2572  -16.2934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9671  -16.7022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6716  -16.2952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6736  -15.4776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9650  -15.0688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2543  -15.4774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3818  -15.0698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0891  -15.4792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.3827  -14.2526    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.0909  -13.8448    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7301  -17.5263    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7277  -16.7091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  6  1  1  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  7  8  2  0
  7 10  1  0
  8  9  1  0
  9 12  2  0
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 11 14  1  0
 12 13  1  0
 13 16  2  0
 15 14  2  0
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 15 20  1  0
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 17 18  2  0
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 19 20  2  0
 14 21  1  0
 21 22  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
 25 28  1  0
 28 29  2  0
 28 30  1  0
 30 31  1  0
  7 32  1  0
 32 33  1  0
 33  2  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4761847

   ---

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: 435.48

Molecular Weight (Monoisotopic): 435.1583

AlogP: 5.83

#Rotatable Bonds: 6

Polar Surface Area: 83.48

Molecular Species: NEUTRAL

HBA: 5

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 9.31

CX Basic pKa: 8.41

CX LogP: 5.05

CX LogD: 4.34

Aromatic Rings: 5

Heavy Atoms: 33

QED Weighted: 0.18

Np Likeness Score: -0.79

References

1. Tseng HJ,Lin MH,Shiao YJ,Yang YC,Chu JC,Chen CY,Chen YY,Lin TE,Su CJ,Pan SL,Chen LC,Wang CY,Hsu KC,Huang WJ.  (2020)  Synthesis and biological evaluation of acridine-based histone deacetylase inhibitors as multitarget agents against Alzheimer's disease.,  192  [PMID:32151835] [10.1016/j.ejmech.2020.112193]

Source

Source(1):

• Scientific Literature