3-[4-(Pyridin-4-yl)piperazin-1-yl]benzyl-N-carbamimidoylcarbamate trihydrochloride

ID: ALA4087881

PubChem CID: 146029991

Max Phase: Preclinical

Molecular Formula: C18H25Cl3N6O2

Molecular Weight: 354.41

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cl.Cl.Cl.N=C(N)NC(=O)OCc1cccc(N2CCN(c3ccncc3)CC2)c1

Standard InChI:  InChI=1S/C18H22N6O2.3ClH/c19-17(20)22-18(25)26-13-14-2-1-3-16(12-14)24-10-8-23(9-11-24)15-4-6-21-7-5-15;;;/h1-7,12H,8-11,13H2,(H4,19,20,22,25);3*1H

Standard InChI Key:  XJGOXNXEWPGPSL-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 29 28  0  0  0  0  0  0  0  0999 V2000
   11.9920  -11.3143    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   13.2007   -9.8661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9098   -9.4575    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.2007  -10.6833    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.4958   -9.4575    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.6189   -9.8661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3280   -9.4575    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.6189  -10.6833    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.7867   -9.8661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0776   -9.4575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3726   -9.8661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6635   -9.4575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6635   -8.6404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3726   -8.2318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0776   -8.6404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9544   -9.8661    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.9544  -10.6833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2495  -11.0919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5404  -10.6833    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.5404   -9.8661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2495   -9.4575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4173  -11.0919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1263  -10.6833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8313  -11.0919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8313  -11.9091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1263  -12.3177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4173  -11.9091    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.2830  -11.3437    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   11.1080  -11.3437    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0
  2  4  2  0
  2  5  1  0
  6  7  1  0
  6  8  2  0
  3  6  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 10 15  2  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 16 21  1  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 22 27  2  0
 19 24  1  0
 12 16  1  0
  5  9  1  0
M  END

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: 354.41

Molecular Weight (Monoisotopic): 354.1804

AlogP: 1.53

#Rotatable Bonds: 4

Polar Surface Area: 107.57

Molecular Species: BASE

HBA: 6

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.32

CX Basic pKa: 8.76

CX LogP: 1.50

CX LogD: 0.16

Aromatic Rings: 2

Heavy Atoms: 26

QED Weighted: 0.57

Np Likeness Score: -1.03

References

1. Yamaki S, Yamada H, Nagashima A, Kondo M, Shimada Y, Kadono K, Yoshihara K..  (2017)  Synthesis and structure activity relationships of carbamimidoylcarbamate derivatives as novel vascular adhesion protein-1 inhibitors.,  25  (21): [PMID:28988626] [10.1016/j.bmc.2017.09.036]

Source

Source(1):

• Scientific Literature