3-(2,4-dichlorophenyl)-N1-hydroxy-N5-(4-ethylbenzyl)pentanediamide

ID: ALA4870620

PubChem CID: 164623430

Max Phase: Preclinical

Molecular Formula: C20H22Cl2N2O3

Molecular Weight: 409.31

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CCc1ccc(CNC(=O)CC(CC(=O)NO)c2ccc(Cl)cc2Cl)cc1

Standard InChI:  InChI=1S/C20H22Cl2N2O3/c1-2-13-3-5-14(6-4-13)12-23-19(25)9-15(10-20(26)24-27)17-8-7-16(21)11-18(17)22/h3-8,11,15,27H,2,9-10,12H2,1H3,(H,23,25)(H,24,26)

Standard InChI Key:  VVUBRMMNSWNGBJ-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 27 28  0  0  0  0  0  0  0  0999 V2000
   14.7425  -18.8449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4543  -18.4363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1661  -18.8449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8780  -18.4363    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.5898  -18.8449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2975  -18.4363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0040  -18.8491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7112  -18.4412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7112  -17.6232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9990  -17.2147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2975  -17.6250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1661  -19.6662    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.0306  -18.4363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0306  -17.6139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3245  -17.2013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6117  -17.6141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6117  -18.4396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3259  -18.8444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9035  -17.2023    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   14.7487  -17.2035    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   14.7425  -19.6662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0306  -20.0790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0306  -20.9003    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.3188  -21.3089    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.3188  -19.6662    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.4183  -17.2135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1267  -17.6211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  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
  3 12  2  0
  1 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 13  1  0
 16 19  1  0
 14 20  1  0
  1 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 22 25  2  0
  9 26  1  0
 26 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4870620

   ---

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: 409.31

Molecular Weight (Monoisotopic): 408.1007

AlogP: 4.24

#Rotatable Bonds: 8

Polar Surface Area: 78.43

Molecular Species: NEUTRAL

HBA: 3

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.90

CX Basic pKa: ┄

CX LogP: 3.96

CX LogD: 3.95

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.45

Np Likeness Score: -0.82

References

1. Turner LD, Nielsen AL, Lin L, Campedelli AJ, Silvaggi NR, Chen JS, Wakefield AE, Allen KN, Janda KD..  (2021)  Use of Crystallography and Molecular Modeling for the Inhibition of the Botulinum Neurotoxin A Protease.,  12  (8.0): [PMID:34413962] [10.1021/acsmedchemlett.1c00325]

Source

Source(1):

• Scientific Literature