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

ID: ALA4095865

PubChem CID: 146029989

Max Phase: Preclinical

Molecular Formula: C17H21Cl2FN6O3

Molecular Weight: 374.38

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cl.Cl.N=C(N)NC(=O)OCc1ccc(F)c(-c2cnc(N3CCOCC3)nc2)c1

Standard InChI:  InChI=1S/C17H19FN6O3.2ClH/c18-14-2-1-11(10-27-17(25)23-15(19)20)7-13(14)12-8-21-16(22-9-12)24-3-5-26-6-4-24;;/h1-2,7-9H,3-6,10H2,(H4,19,20,23,25);2*1H

Standard InChI Key:  LFUOTNYKGSAHBA-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 29 29  0  0  0  0  0  0  0  0999 V2000
   11.4947  -10.6317    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   10.9573   -8.4098    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.2424   -8.8217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5317   -8.4098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8168   -8.8217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1019   -8.4098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1019   -7.5859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8168   -7.1740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5317   -7.5859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9614   -9.6456    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9614   -8.8217    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.6763   -8.4098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3912   -8.8217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3912   -9.6456    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6763  -10.0575    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2507  -10.0575    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2507  -10.8814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5359  -11.2933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8210  -10.8814    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8210  -10.0575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5359   -9.6456    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3912   -7.1740    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   11.6704   -8.8223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3843   -8.4110    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.6698   -9.6462    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.0975   -8.8235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8113   -8.4122    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.0968   -9.6474    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.2865  -10.6317    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
  7 22  1  0
  2 23  1  0
 23 24  1  0
 23 25  2  0
 24 26  1  0
 26 27  1  0
 26 28  2  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: 374.38

Molecular Weight (Monoisotopic): 374.1503

AlogP: 1.24

#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: 7.87

CX LogP: 1.47

CX LogD: 0.88

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.54

Np Likeness Score: -1.31

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