N1-benzyl-3-(2,4-dichlorophenyl)-N5-hydroxypentanediamide

ID: ALA4866455

PubChem CID: 164620133

Max Phase: Preclinical

Molecular Formula: C18H18Cl2N2O3

Molecular Weight: 381.26

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C(CC(CC(=O)NCc1ccccc1)c1ccc(Cl)cc1Cl)NO

Standard InChI:  InChI=1S/C18H18Cl2N2O3/c19-14-6-7-15(16(20)10-14)13(9-18(24)22-25)8-17(23)21-11-12-4-2-1-3-5-12/h1-7,10,13,25H,8-9,11H2,(H,21,23)(H,22,24)

Standard InChI Key:  RDRNDOZRQYURNN-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 25 26  0  0  0  0  0  0  0  0999 V2000
   14.9901  -12.1423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7019  -11.7337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4138  -12.1423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1256  -11.7337    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.8374  -12.1423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5451  -11.7337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2516  -12.1465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9589  -11.7386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9589  -10.9205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2466  -10.5121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5451  -10.9224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4138  -12.9636    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.2783  -11.7337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2783  -10.9113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5722  -10.4987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8594  -10.9115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8594  -11.7370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5736  -12.1418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1511  -10.4997    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   14.9963  -10.5009    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   14.9901  -12.9636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2783  -13.3763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2783  -14.1977    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.5664  -14.6063    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.5664  -12.9636    0.0000 O   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
M  END

Alternative Forms

1. Parent:

   

   ALA4866455

   ---

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: 381.26

Molecular Weight (Monoisotopic): 380.0694

AlogP: 3.68

#Rotatable Bonds: 7

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: 3.01

CX LogD: 2.99

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.51

Np Likeness Score: -0.79

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