tert-Butyl 4-((3-chloro-4-(5-chloro-2-hydroxybenzamido)-phenyl)amino)piperidine-1-carboxylate

ID: ALA4755440

PubChem CID: 162655178

Max Phase: Preclinical

Molecular Formula: C23H27Cl2N3O4

Molecular Weight: 480.39

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CC(C)(C)OC(=O)N1CCC(Nc2ccc(NC(=O)c3cc(Cl)ccc3O)c(Cl)c2)CC1

Standard InChI:  InChI=1S/C23H27Cl2N3O4/c1-23(2,3)32-22(31)28-10-8-15(9-11-28)26-16-5-6-19(18(25)13-16)27-21(30)17-12-14(24)4-7-20(17)29/h4-7,12-13,15,26,29H,8-11H2,1-3H3,(H,27,30)

Standard InChI Key:  AXTMDONCGOKNOT-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 32 34  0  0  0  0  0  0  0  0999 V2000
   16.8874  -10.1416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4790   -9.4290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0661  -10.1390    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0549   -7.7824    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.0549   -6.9574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3391   -6.5449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6274   -6.9574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6274   -7.7824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3391   -8.1949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7667   -8.1949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4825   -7.7824    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.7667   -9.0199    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.9116   -6.5449    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.1957   -6.9574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4798   -6.5449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7681   -6.9574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7681   -7.7824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4798   -8.1949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1957   -7.7824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3406   -7.7824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6247   -8.1949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9089   -7.7824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1930   -8.1949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1930   -9.0199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9089   -9.4324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6247   -9.0199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3406   -6.9574    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0523   -8.1949    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.9089   -6.9574    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9089  -10.2574    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   10.0523   -6.5449    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   17.1966   -9.0193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  4  9  1  0
 10 11  2  0
 10 12  1  0
  4 10  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 14 19  2  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 21 26  2  0
 20 27  2  0
 20 28  1  0
 22 29  1  0
 25 30  1  0
 17 28  1  0
 16 31  1  0
 13 14  1  0
  7 13  1  0
 12  2  1  0
  2 32  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4755440

   ---

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: 480.39

Molecular Weight (Monoisotopic): 479.1379

AlogP: 5.76

#Rotatable Bonds: 4

Polar Surface Area: 90.90

Molecular Species: NEUTRAL

HBA: 5

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 7.39

CX Basic pKa: 4.23

CX LogP: 4.37

CX LogD: 4.07

Aromatic Rings: 2

Heavy Atoms: 32

QED Weighted: 0.52

Np Likeness Score: -1.57

References

1. Xu J,Berastegui-Cabrera J,Ye N,Carretero-Ledesma M,Pachón-Díaz J,Chen H,Pachón-Ibáñez ME,Sánchez-Céspedes J,Zhou J.  (2020)  Discovery of Novel Substituted N-(4-Amino-2-chlorophenyl)-5-chloro-2-hydroxybenzamide Analogues as Potent Human Adenovirus Inhibitors.,  63  (21): [PMID:33112138] [10.1021/acs.jmedchem.0c01226]

Source

Source(1):

• Scientific Literature