N-(3,5-dichlorophenyl)-4-(1H-indol-4-yl)piperazine-1-carboxamide

ID: ALA4249741

PubChem CID: 145983378

Max Phase: Preclinical

Molecular Formula: C19H18Cl2N4O

Molecular Weight: 389.29

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(Nc1cc(Cl)cc(Cl)c1)N1CCN(c2cccc3[nH]ccc23)CC1

Standard InChI:  InChI=1S/C19H18Cl2N4O/c20-13-10-14(21)12-15(11-13)23-19(26)25-8-6-24(7-9-25)18-3-1-2-17-16(18)4-5-22-17/h1-5,10-12,22H,6-9H2,(H,23,26)

Standard InChI Key:  HVHNADUKFDFWLM-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 26 29  0  0  0  0  0  0  0  0999 V2000
    4.1685  -14.8085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9857  -14.8085    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5359  -14.8064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9489  -15.5164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7640  -15.5133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3931  -15.5180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2067  -15.5200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6191  -14.8141    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.2117  -14.1046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3919  -14.1009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9453  -14.0981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7597  -14.0987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0119  -13.3243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3533  -12.8451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6942  -13.3235    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.4363  -14.8172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8422  -15.5264    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.8476  -14.1110    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6594  -15.5295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0616  -16.2388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8780  -16.2422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2901  -15.5355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8798  -14.8239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0648  -14.8240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2836  -16.9517    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   10.2886  -14.1163    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  1 12  1  0
 11  3  1  0
  3  4  2  0
  4  5  1  0
  5  1  2  0
  2  6  1  0
  2 10  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 11  1  0
  8 16  1  0
 16 17  1  0
 16 18  2  0
 17 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 19  1  0
 21 25  1  0
 23 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4249741

   ---

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: 389.29

Molecular Weight (Monoisotopic): 388.0858

AlogP: 4.83

#Rotatable Bonds: 2

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: 12.80

CX Basic pKa: 2.98

CX LogP: 4.37

CX LogD: 4.37

Aromatic Rings: 3

Heavy Atoms: 26

QED Weighted: 0.66

Np Likeness Score: -1.64

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