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

ID: ALA4873243

PubChem CID: 164623571

Max Phase: Preclinical

Molecular Formula: C18H19Cl2N3O3

Molecular Weight: 396.27

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Nc1ccc(CNC(=O)CC(CC(=O)NO)c2ccc(Cl)cc2Cl)cc1

Standard InChI:  InChI=1S/C18H19Cl2N3O3/c19-13-3-6-15(16(20)9-13)12(8-18(25)23-26)7-17(24)22-10-11-1-4-14(21)5-2-11/h1-6,9,12,26H,7-8,10,21H2,(H,22,24)(H,23,25)

Standard InChI Key:  PVMMXAMWTPZLAF-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 26 27  0  0  0  0  0  0  0  0999 V2000
   34.2065  -28.0528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.9183  -27.6442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.6301  -28.0528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.3420  -27.6442    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   37.0538  -28.0528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.7615  -27.6442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.4680  -28.0570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.1752  -27.6491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.1752  -26.8310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.4630  -26.4226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.7615  -26.8328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.6301  -28.8741    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   33.4946  -27.6442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.4946  -26.8218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.7886  -26.4091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.0757  -26.8219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.0757  -27.6475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.7900  -28.0523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.3675  -26.4101    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   34.2127  -26.4114    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   34.2065  -28.8741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.4946  -29.2868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.4946  -30.1081    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   32.7828  -30.5167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.7828  -28.8741    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   39.8824  -26.4214    0.0000 N   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
M  END

Alternative Forms

1. Parent:

   

   ALA4873243

   ---

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: 396.27

Molecular Weight (Monoisotopic): 395.0803

AlogP: 3.26

#Rotatable Bonds: 7

Polar Surface Area: 104.45

Molecular Species: NEUTRAL

HBA: 4

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.90

CX Basic pKa: 4.25

CX LogP: 2.18

CX LogD: 2.16

Aromatic Rings: 2

Heavy Atoms: 26

QED Weighted: 0.33

Np Likeness Score: -0.71

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