2-(2-(7-(diethylamino)-2-oxo-2H-chromen-3-yl)-1H-benzo[d]imidazol-5-yl)-4,5-dihydro-1H-imidazol-3-ium chloride

ID: ALA5284601

Max Phase: Preclinical

Molecular Formula: C23H24ClN5O2

Molecular Weight: 401.47

Names and Identifiers

Canonical SMILES:  CCN(CC)c1ccc2cc(-c3nc4cc(C5=NCCN5)ccc4[nH]3)c(=O)oc2c1.Cl

Standard InChI:  InChI=1S/C23H23N5O2.ClH/c1-3-28(4-2)16-7-5-14-11-17(23(29)30-20(14)13-16)22-26-18-8-6-15(12-19(18)27-22)21-24-9-10-25-21;/h5-8,11-13H,3-4,9-10H2,1-2H3,(H,24,25)(H,26,27);1H

Standard InChI Key:  UIOIAAZYDYFLLF-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 31 34  0  0  0  0  0  0  0  0999 V2000
    3.8504    0.1759    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.6324   -1.6128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1093   -0.9396    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9227   -1.1921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9227   -2.0336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1093   -2.2860    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7909   -1.6128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3701   -0.8835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5287   -0.8835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1079   -1.6128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2664   -1.4444    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1823   -0.6030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9677   -0.2664    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5469   -0.1823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5469    0.6591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2762    1.0799    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0055    0.6591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7348    1.0799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4641    0.6591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4641   -0.1823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7348   -0.6030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0055   -0.1823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2762   -0.6030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1933    1.0799    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9227    0.6591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9227   -0.1823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1933    1.9214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4641    2.3421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1823    1.0799    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5287   -2.3421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3701   -2.3421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  4  5  1  0
  5  6  1  0
  2  6  1  0
  2  7  1  0
  8  7  1  0
  8  9  2  0
 10  9  1  0
 11 10  1  0
 12 11  1  0
  9 13  1  0
 12 13  2  0
 12 14  1  0
 15 14  1  0
 15 16  1  0
 17 16  1  0
 18 17  1  0
 19 18  2  0
 20 19  1  0
 21 20  2  0
 22 21  1  0
 22 17  2  0
 14 23  2  0
 23 22  1  0
 19 24  1  0
 24 25  1  0
 25 26  1  0
 24 27  1  0
 27 28  1  0
 15 29  2  0
 30 10  2  0
  7 31  2  0
 31 30  1  0
  2  3  2  0
  3  4  1  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: 401.47

Molecular Weight (Monoisotopic): 401.1852

AlogP: 3.53

#Rotatable Bonds: 5

Polar Surface Area: 86.52

Molecular Species: BASE

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.84

CX Basic pKa: 8.62

CX LogP: 2.67

CX LogD: 1.76

Aromatic Rings: 4

Heavy Atoms: 30

QED Weighted: 0.50

Np Likeness Score: -0.82

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