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

ID: ALA5274153

Max Phase: Preclinical

Molecular Formula: C21H18Cl2N4O2

Molecular Weight: 392.85

Names and Identifiers

Canonical SMILES:  Cc1ccc2oc(=O)c(-c3nc4cc(C5=NCCCN5)ccc4[nH]3)c(Cl)c2c1.Cl

Standard InChI:  InChI=1S/C21H17ClN4O2.ClH/c1-11-3-6-16-13(9-11)18(22)17(21(27)28-16)20-25-14-5-4-12(10-15(14)26-20)19-23-7-2-8-24-19;/h3-6,9-10H,2,7-8H2,1H3,(H,23,24)(H,25,26);1H

Standard InChI Key:  SRDROSOAMPBSPJ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 29 32  0  0  0  0  0  0  0  0999 V2000
    2.9024   -0.6835    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.0093    0.9618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4216    1.6765    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2461    1.6765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6584    0.9618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2461    0.2473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4216    0.2473    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1849    0.9618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7726    0.2473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9481    0.2473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5359    0.9618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2885    0.7969    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3710   -0.0275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3985   -0.3573    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0855   -0.4397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0855   -1.2642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8001   -1.6765    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5147   -1.2642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2292   -1.6765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9438   -1.2642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9438   -0.4397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2292   -0.0275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5147   -0.4397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8001   -0.0275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8001    0.7969    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -4.6584   -0.0275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3710   -1.6765    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9481    1.6765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7726    1.6765    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
 21 26  1  0
 16 27  2  0
 28 11  2  0
  8 29  2  0
 29 28  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: 392.85

Molecular Weight (Monoisotopic): 392.1040

AlogP: 4.04

#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: 2.30

CX LogD: 1.11

Aromatic Rings: 4

Heavy Atoms: 28

QED Weighted: 0.50

Np Likeness Score: -0.61

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