5-Chloro-3-((E)-3-((E)-(2-(4,5-dihydro-1H-imidazol-2-yl)hydrazineylidene)methyl)benzylidene)indolin-2-one Hydrochloride

ID: ALA4517447

PubChem CID: 155540979

Max Phase: Preclinical

Molecular Formula: C19H17Cl2N5O

Molecular Weight: 365.82

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Cl.O=C1Nc2ccc(Cl)cc2/C1=C\c1cccc(/C=N/NC2=NCCN2)c1

Standard InChI:  InChI=1S/C19H16ClN5O.ClH/c20-14-4-5-17-15(10-14)16(18(26)24-17)9-12-2-1-3-13(8-12)11-23-25-19-21-6-7-22-19;/h1-5,8-11H,6-7H2,(H,24,26)(H2,21,22,25);1H/b16-9+,23-11+;

Standard InChI Key:  YDYQYABGEIVPOI-VASAINNFSA-N

Molfile:  

     RDKit          2D

 27 29  0  0  0  0  0  0  0  0999 V2000
    6.7728   -7.4249    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    5.8386   -4.8783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8375   -5.7020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5455   -6.1110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2593   -5.7015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2565   -4.8747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5437   -4.4654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9718   -6.1090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6830   -5.6993    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.3954   -6.1068    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.1253   -6.1100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4138   -5.7009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1108   -5.4185    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6613   -6.0302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4895   -6.8333    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5241   -4.7069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3265   -4.8820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8716   -4.2727    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6197   -3.4924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1066   -5.6971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2677   -3.9353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8154   -3.3264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1653   -2.8840    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   10.8517   -6.0328    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.4015   -5.4234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9917   -4.7122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1888   -4.8822    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  2  0
 19 23  1  0
 20 24  2  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 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: 365.82

Molecular Weight (Monoisotopic): 365.1043

AlogP: 2.72

#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: 11.29

CX Basic pKa: 5.94

CX LogP: 3.19

CX LogD: 3.18

Aromatic Rings: 2

Heavy Atoms: 26

QED Weighted: 0.44

Np Likeness Score: -0.99

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