2-hydroxy-N-(2-(4-(3-(hydroxyamino)-3-oxoprop-1-enyl)-2-methoxyphenoxy)ethyl)-N-methylbenzamide

ID: ALA4465947

PubChem CID: 155531688

Max Phase: Preclinical

Molecular Formula: C20H22N2O6

Molecular Weight: 386.40

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COc1cc(/C=C/C(=O)NO)ccc1OCCN(C)C(=O)c1ccccc1O

Standard InChI:  InChI=1S/C20H22N2O6/c1-22(20(25)15-5-3-4-6-16(15)23)11-12-28-17-9-7-14(13-18(17)27-2)8-10-19(24)21-26/h3-10,13,23,26H,11-12H2,1-2H3,(H,21,24)/b10-8+

Standard InChI Key:  SJRQWJPPQGTGSY-CSKARUKUSA-N

Molfile:  

 
     RDKit          2D

 28 29  0  0  0  0  0  0  0  0999 V2000
   34.5682   -8.2627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.5671   -9.0822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.2751   -9.4912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.9848   -9.0817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.9820   -8.2591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.2734   -7.8538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.8591   -9.4902    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   33.8604   -7.8542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   33.8602   -7.0371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.6881   -7.8478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.3974   -8.2537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.1036   -7.8425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.8128   -8.2484    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   38.1005   -7.0253    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   39.5190   -7.8371    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   33.1517   -9.0811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.4437   -9.4891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.7363   -9.0800    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   31.0282   -9.4880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.3209   -9.0788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.0276  -10.3052    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.3265   -8.2637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.6199   -7.8546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.9109   -8.2627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.9129   -9.0841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.6200   -9.4895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.6239  -10.3067    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.7369   -8.2628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  1  1  0
  2  7  1  0
  1  8  1  0
  8  9  1  0
  5 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 12 14  2  0
 13 15  1  0
  7 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 19 21  2  0
 20 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 20  1  0
 26 27  1  0
 18 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4465947

   ---

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: 386.40

Molecular Weight (Monoisotopic): 386.1478

AlogP: 2.07

#Rotatable Bonds: 8

Polar Surface Area: 108.33

Molecular Species: NEUTRAL

HBA: 6

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.16

CX Basic pKa: ┄

CX LogP: 2.46

CX LogD: 2.39

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.36

Np Likeness Score: -0.58

References

1. Sangwan R, Rajan R, Mandal PK..  (2018)  HDAC as onco target: Reviewing the synthetic approaches with SAR study of their inhibitors.,  158  [PMID:30245394] [10.1016/j.ejmech.2018.08.073]

Source

Source(1):

• Scientific Literature