2-(2-(4-chloro-2-oxo-2H-chromen-3-yl)-1H-benzo[d]imidazol-5-yl)-3,4,5,6-tetrahydropyrimidin-1-ium chloride

ID: ALA5286680

Max Phase: Preclinical

Molecular Formula: C20H16Cl2N4O2

Molecular Weight: 378.82

Names and Identifiers

Canonical SMILES:  Cl.O=c1oc2ccccc2c(Cl)c1-c1nc2cc(C3=NCCCN3)ccc2[nH]1

Standard InChI:  InChI=1S/C20H15ClN4O2.ClH/c21-17-12-4-1-2-5-15(12)27-20(26)16(17)19-24-13-7-6-11(10-14(13)25-19)18-22-8-3-9-23-18;/h1-2,4-7,10H,3,8-9H2,(H,22,23)(H,24,25);1H

Standard InChI Key:  JDGYUPJHRMHESI-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 28 31  0  0  0  0  0  0  0  0999 V2000
    2.5111   -0.4826    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.6385    0.9620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0508    1.6766    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8754    1.6766    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2877    0.9620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8754    0.2473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0508    0.2473    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8140    0.9620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4017    0.2473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5770    0.2473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1649    0.9620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6321    0.7971    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7421   -0.0274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0275   -0.3572    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4567   -0.4397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4567   -1.2643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1713   -1.6766    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8859   -1.2643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5731   -1.6766    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2877   -1.2643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2877   -0.4397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5731   -0.0274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8859   -0.4397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1713   -0.0274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1713    0.7971    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.7421   -1.6766    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5770    1.6766    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4017    1.6766    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  2  8  1  0
  9  8  1  0
  9 10  2  0
 11 10  1  0
 12 11  1  0
 13 12  1  0
 10 14  1  0
 13 14  2  0
 13 15  1  0
 16 15  1  0
 16 17  1  0
 18 17  1  0
 19 18  1  0
 20 19  2  0
 21 20  1  0
 22 21  2  0
 23 22  1  0
 23 18  2  0
 15 24  2  0
 24 23  1  0
 24 25  1  0
 16 26  2  0
 27 11  2  0
  8 28  2  0
 28 27  1  0
  6  7  1  0
  2  7  2  0
M  END

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type:

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 378.82

Molecular Weight (Monoisotopic): 378.0884

AlogP: 3.73

#Rotatable Bonds: 2

Polar Surface Area: 83.28

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.42

CX Basic pKa: 8.49

CX LogP: 1.79

CX LogD: 0.60

Aromatic Rings: 4

Heavy Atoms: 27

QED Weighted: 0.52

Np Likeness Score: -0.55

References

1. Beč A, Racané L, Žonja L, Persoons L, Daelemans D, Starčević K, Vianello R, Hranjec M..  (2023)  Biological evaluation of novel amidino substituted coumarin-benzazole hybrids as promising therapeutic agents.,  14  (5): [PMID:37252100] [10.1039/d3md00055a]

Source

Source(1):

• Scientific Literature