N-(4-chlorobenzyl)-4-(1H-indol-4-yl)piperazine-1-carboxamide

ID: ALA4250509

PubChem CID: 145982672

Max Phase: Preclinical

Molecular Formula: C20H21ClN4O

Molecular Weight: 368.87

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(NCc1ccc(Cl)cc1)N1CCN(c2cccc3[nH]ccc23)CC1

Standard InChI:  InChI=1S/C20H21ClN4O/c21-16-6-4-15(5-7-16)14-23-20(26)25-12-10-24(11-13-25)19-3-1-2-18-17(19)8-9-22-18/h1-9,22H,10-14H2,(H,23,26)

Standard InChI Key:  KAGNBDUHBIQVBQ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 26 29  0  0  0  0  0  0  0  0999 V2000
   31.3545  -16.5089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.1717  -16.5089    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   29.7219  -16.5068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.1349  -17.2168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.9500  -17.2137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.1313  -15.7985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.9457  -15.7946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.1937  -15.0188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.5324  -14.5432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.8759  -15.0252    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   32.5730  -17.2167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.3866  -17.2187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.7990  -16.5128    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   33.3916  -15.8033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.5718  -15.7997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.6162  -16.5159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.0275  -15.8097    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   35.0221  -17.2251    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   35.8393  -17.2282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.2452  -17.9375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.8314  -18.6428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.2366  -19.3515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.0547  -19.3551    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.4658  -18.6439    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.0582  -17.9381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.4615  -20.0638    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  7  1  0
  6  3  1  0
  3  4  2  0
  4  5  1  0
  5  1  2  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10  6  1  0
  2 11  1  0
  2 15  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 13 16  1  0
 16 17  2  0
 16 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 20  1  0
 23 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4250509

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 368.87

Molecular Weight (Monoisotopic): 368.1404

AlogP: 3.85

#Rotatable Bonds: 3

Polar Surface Area: 51.37

Molecular Species: NEUTRAL

HBA: 2

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 2.98

CX LogP: 3.47

CX LogD: 3.47

Aromatic Rings: 3

Heavy Atoms: 26

QED Weighted: 0.74

Np Likeness Score: -1.57

References

1. Anglin J, Zavareh RB, Sander PN, Haldar D, Mullarky E, Cantley LC, Kimmelman AC, Lyssiotis CA, Lairson LL..  (2018)  Discovery and optimization of aspartate aminotransferase 1 inhibitors to target redox balance in pancreatic ductal adenocarcinoma.,  28  (16): [PMID:29731362] [10.1016/j.bmcl.2018.04.061]

Source

Source(1):

• Scientific Literature