N-Hydroxy-4-(1,2,3-trimethoxyacridin-9-ylamino)benzamide

ID: ALA4753795

PubChem CID: 162653917

Max Phase: Preclinical

Molecular Formula: C23H21N3O5

Molecular Weight: 419.44

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COc1cc2nc3ccccc3c(Nc3ccc(C(=O)NO)cc3)c2c(OC)c1OC

Standard InChI:  InChI=1S/C23H21N3O5/c1-29-18-12-17-19(22(31-3)21(18)30-2)20(15-6-4-5-7-16(15)25-17)24-14-10-8-13(9-11-14)23(27)26-28/h4-12,28H,1-3H3,(H,24,25)(H,26,27)

Standard InChI Key:  RXYDUXPNMOBQTR-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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   17.6233  -18.2176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3285  -18.6221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3285  -16.9877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0338  -17.4004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0349  -18.2176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7392  -18.6230    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.7371  -16.9886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4459  -17.3986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4508  -18.2177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   21.1490  -16.9826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7349  -16.1715    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.4415  -15.7610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1514  -16.1698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8559  -15.7628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8579  -14.9452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1493  -14.5363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4386  -14.9450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.5661  -14.5374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.2734  -14.9468    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.5670  -13.7202    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.2752  -13.3124    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.9144  -16.9939    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.9162  -18.6272    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.3285  -16.1705    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.9173  -19.4444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2079  -17.4045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6208  -15.7619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  1  4  1  0
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  3  6  2  0
  5  4  2  0
  5  6  1  0
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  6  7  1  0
  7 10  2  0
  9  8  2  0
  9 10  1  0
  9 14  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
  8 15  1  0
 15 16  1  0
 16 17  2  0
 16 21  1  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 19 22  1  0
 22 23  2  0
 22 24  1  0
 24 25  1  0
  1 26  1  0
  2 27  1  0
  4 28  1  0
 27 29  1  0
 26 30  1  0
 28 31  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4753795

   ---

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: 419.44

Molecular Weight (Monoisotopic): 419.1481

AlogP: 4.28

#Rotatable Bonds: 6

Polar Surface Area: 101.94

Molecular Species: BASE

HBA: 7

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.42

CX Basic pKa: 8.76

CX LogP: 2.86

CX LogD: 1.99

Aromatic Rings: 4

Heavy Atoms: 31

QED Weighted: 0.24

Np Likeness Score: -0.36

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