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

ID: ALA4077021

PubChem CID: 89600723

Max Phase: Preclinical

Molecular Formula: C17H20ClFN6O3

Molecular Weight: 374.38

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cl.N=C(N)NC(=O)OCc1cccc(-c2cnc(N3CCOCC3)nc2)c1F

Standard InChI:  InChI=1S/C17H19FN6O3.ClH/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);1H

Standard InChI Key:  AJIQJXLVMAPAKX-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 28 29  0  0  0  0  0  0  0  0999 V2000
   10.8031  -10.7341    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   11.8215   -8.6211    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.1068   -9.0330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3961   -8.6211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6813   -9.0330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9664   -8.6211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9664   -7.7973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6813   -7.3854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3961   -7.7973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8262   -9.8568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8262   -9.0330    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.5410   -8.6211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2559   -9.0330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2559   -9.8568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5410  -10.2687    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.1155  -10.2687    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.1155  -11.0925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4007  -11.5044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6859  -11.0925    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6859  -10.2687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4007   -9.8568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5346   -9.0336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2484   -8.6223    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.5339   -9.8574    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.9614   -9.0348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6752   -8.6235    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.9607   -9.8586    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.6813   -9.8568    0.0000 F   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: 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: -1.26

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