[2-chloro-3-(2-morpholinopyrimidin-5-yl)phenyl]methyl N-carbamimidoylcarbamate dihydrochloride

ID: ALA4097484

PubChem CID: 146029690

Max Phase: Preclinical

Molecular Formula: C17H21Cl3N6O3

Molecular Weight: 390.83

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cl.Cl.N=C(N)NC(=O)OCc1cccc(-c2cnc(N3CCOCC3)nc2)c1Cl

Standard InChI:  InChI=1S/C17H19ClN6O3.2ClH/c18-14-11(10-27-17(25)23-15(19)20)2-1-3-13(14)12-8-21-16(22-9-12)24-4-6-26-7-5-24;;/h1-3,8-9H,4-7,10H2,(H4,19,20,23,25);2*1H

Standard InChI Key:  YHAGWBYGXBRHER-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 29 29  0  0  0  0  0  0  0  0999 V2000
   10.8388  -11.2530    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   10.6993   -8.7759    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.9844   -9.1879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2737   -8.7759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5588   -9.1879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8440   -8.7759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8440   -7.9521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5589   -7.5401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2737   -7.9521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7034  -10.0118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7034   -9.1879    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.4183   -8.7759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1332   -9.1879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1332  -10.0118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4183  -10.4237    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9928  -10.4237    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9928  -11.2476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2779  -11.6595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5630  -11.2476    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5630  -10.4237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2779  -10.0118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4125   -9.1885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1263   -8.7772    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.4118  -10.0124    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.8395   -9.1897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5533   -8.7784    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.8388  -10.0136    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.5588  -10.0118    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    9.6307  -11.2185    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  4  9  2  0
  2  3  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
 10 16  1  0
  6 13  1  0
  2 22  1  0
 22 23  1  0
 22 24  2  0
 23 25  1  0
 25 26  1  0
 25 27  2  0
  5 28  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: 390.83

Molecular Weight (Monoisotopic): 390.1207

AlogP: 1.75

#Rotatable Bonds: 4

Polar Surface Area: 126.45

Molecular Species: NEUTRAL

HBA: 7

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.46

CX Basic pKa: 7.83

CX LogP: 1.93

CX LogD: 1.37

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.54

Np Likeness Score: -1.14

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