4-((2,6-Difluorophenyl)ethynyl)-1-(4-methylpiperazin-1-yl)isoquinoline hydrochloride salt

ID: ALA4294532

PubChem CID: 145993549

Max Phase: Preclinical

Molecular Formula: C22H20ClF2N3

Molecular Weight: 363.41

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CN1CCN(c2ncc(C#Cc3c(F)cccc3F)c3ccccc23)CC1.Cl

Standard InChI:  InChI=1S/C22H19F2N3.ClH/c1-26-11-13-27(14-12-26)22-18-6-3-2-5-17(18)16(15-25-22)9-10-19-20(23)7-4-8-21(19)24;/h2-8,15H,11-14H2,1H3;1H

Standard InChI Key:  HZRWLVXBRZDKBB-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 28 30  0  0  0  0  0  0  0  0999 V2000
   26.9304  -26.9009    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   24.4951  -25.6751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.0865  -26.3842    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.2652  -26.3842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8525  -25.6751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.2652  -24.9619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8525  -24.2528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.2652  -23.5437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.0865  -23.5437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.4951  -24.2528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.0865  -24.9619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.3164  -25.6751    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   25.7291  -24.9619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.5505  -24.9619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.9591  -25.6751    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   26.5505  -26.3842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.7291  -26.3842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.7804  -25.6751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0311  -25.6751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2098  -25.6751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3885  -25.6751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9799  -26.3842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1586  -26.3842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7459  -25.6751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1586  -24.9619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9799  -24.9619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3885  -24.2528    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   20.3885  -27.0974    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
  2 11  1  0
  6 11  2  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 12 17  1  0
 15 18  1  0
  2 12  1  0
 19 20  3  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 21 26  2  0
 26 27  1  0
 22 28  1  0
 20 21  1  0
  5 19  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: 363.41

Molecular Weight (Monoisotopic): 363.1547

AlogP: 3.66

#Rotatable Bonds: 1

Polar Surface Area: 19.37

Molecular Species: NEUTRAL

HBA: 3

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 7.69

CX LogP: 4.70

CX LogD: 4.23

Aromatic Rings: 3

Heavy Atoms: 27

QED Weighted: 0.62

Np Likeness Score: -1.26

References

1. Sviripa VM, Kril LM, Zhang W, Xie Y, Wyrebek P, Ponomareva L, Liu X, Yuan Y, Zhan CG, Watt DS, Liu C..  (2018)  Phenylethynyl-substituted Heterocycles Inhibit Cyclin D1 and Induce the Expression of Cyclin-dependent Kinase Inhibitor p21Wif1/Cip1 in Colorectal Cancer Cells.,  9  (1): [PMID:29527286] [10.1039/C7MD00393E]

Source

Source(1):

• Scientific Literature