3-((E)-3-((E)-(2-(4,5-Dihydro-1H-imidazol-2-yl)hydrazineylidene)methyl)benzylidene)-1,3-dihydro-2H-benzo[g]indol-2-one Hydrochloride

ID: ALA4548133

PubChem CID: 155554043

Max Phase: Preclinical

Molecular Formula: C23H20ClN5O

Molecular Weight: 381.44

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Cl.O=C1Nc2c(ccc3ccccc23)/C1=C\c1cccc(/C=N/NC2=NCCN2)c1

Standard InChI:  InChI=1S/C23H19N5O.ClH/c29-22-20(19-9-8-17-6-1-2-7-18(17)21(19)27-22)13-15-4-3-5-16(12-15)14-26-28-23-24-10-11-25-23;/h1-9,12-14H,10-11H2,(H,27,29)(H2,24,25,28);1H/b20-13+,26-14+;

Standard InChI Key:  XMJCZUISYKRUGY-CRDAMREUSA-N

Molfile:  

     RDKit          2D

 30 33  0  0  0  0  0  0  0  0999 V2000
   20.1574  -28.3582    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   19.6896  -25.9974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6884  -26.8210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3965  -27.2300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1103  -26.8206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1074  -25.9938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3947  -25.5844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8228  -27.2281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.5339  -26.8183    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.2464  -27.2258    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.9763  -27.2291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2648  -26.8199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9618  -26.5375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.5123  -27.1493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3405  -27.9523    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.3751  -25.8260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1774  -26.0010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7226  -25.3918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4707  -24.6114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.9576  -26.8161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1187  -25.0543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6663  -24.4454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4125  -23.6688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6114  -23.4999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0647  -24.1138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3214  -24.8880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.7045  -27.1477    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   25.2543  -26.5383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.8446  -25.8270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.0416  -25.9970    0.0000 N   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  2  0
  7  2  1  0
  5  8  1  0
  8  9  2  0
  9 10  1  0
  3 11  1  0
 11 12  2  0
 12 17  1  0
 16 13  1  0
 13 14  1  0
 14 12  1  0
 14 15  2  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 22  1  0
 21 16  1  0
 10 20  1  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 21  2  0
 20 27  2  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 30 20  1  0
M  END

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 381.44

Molecular Weight (Monoisotopic): 381.1590

AlogP: 3.22

#Rotatable Bonds: 3

Polar Surface Area: 77.88

Molecular Species: NEUTRAL

HBA: 5

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.81

CX Basic pKa: 5.53

CX LogP: 3.58

CX LogD: 3.57

Aromatic Rings: 3

Heavy Atoms: 29

QED Weighted: 0.37

Np Likeness Score: -0.61

References

1. Amato J, Miglietta G, Morigi R, Iaccarino N, Locatelli A, Leoni A, Novellino E, Pagano B, Capranico G, Randazzo A..  (2020)  Monohydrazone Based G-Quadruplex Selective Ligands Induce DNA Damage and Genome Instability in Human Cancer Cells.,  63  (6): [PMID:32142285] [10.1021/acs.jmedchem.9b01866]

Source

Source(1):

• Scientific Literature