3-[4-(Morpholin-4-yl)piperidin-1-yl]benzyl-N-carbamimidoylcarbamate trihydrochloride

ID: ALA4060583

PubChem CID: 146029983

Max Phase: Preclinical

Molecular Formula: C18H30Cl3N5O3

Molecular Weight: 361.45

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cl.Cl.Cl.N=C(N)NC(=O)OCc1cccc(N2CCC(N3CCOCC3)CC2)c1

Standard InChI:  InChI=1S/C18H27N5O3.3ClH/c19-17(20)21-18(24)26-13-14-2-1-3-16(12-14)22-6-4-15(5-7-22)23-8-10-25-11-9-23;;;/h1-3,12,15H,4-11,13H2,(H4,19,20,21,24);3*1H

Standard InChI Key:  WNISZOQHYUHFJD-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 29 28  0  0  0  0  0  0  0  0999 V2000
   11.0951  -12.2818    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   11.7996  -10.0751    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.5177  -10.4906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9460  -10.4918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2322  -10.0764    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.9453  -11.3128    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.3727   -9.2498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6606  -10.0776    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.9414   -9.2498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5170  -11.3116    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.6571  -10.4899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3727  -10.0751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6571   -8.8392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2300  -10.4899    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.9414  -10.0751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0840  -10.4899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5177  -10.0778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8084  -10.4890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8077  -11.3129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5224  -11.7238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2379  -11.3109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0989  -11.7224    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.3862  -11.3090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6760  -11.7173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6721  -12.5404    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3847  -12.9537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1012  -12.5438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1075  -12.2818    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   10.0568  -12.2818    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0
  4  6  2  0
 11 15  2  0
 15  9  1  0
  4  8  1  0
 13  7  1  0
 12  7  2  0
 12 11  1  0
  9 13  2  0
 16 12  1  0
  3  5  1  0
  5  4  1  0
  3 10  2  0
  2 16  1  0
 15 14  1  0
 14 17  1  0
 14 21  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 22 23  1  0
 22 27  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 19 22  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: 361.45

Molecular Weight (Monoisotopic): 361.2114

AlogP: 1.11

#Rotatable Bonds: 4

Polar Surface Area: 103.91

Molecular Species: NEUTRAL

HBA: 6

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.31

CX Basic pKa: 8.16

CX LogP: 0.95

CX LogD: -0.20

Aromatic Rings: 1

Heavy Atoms: 26

QED Weighted: 0.55

Np Likeness Score: -1.13

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