2-((E)-3-(((E)-5-Hydroxy-6-methyl-2-oxoindolin-3-ylidene)methyl)benzylidene)hydrazine-1-carboximidamide Hydrochloride

ID: ALA4535658

PubChem CID: 155547639

Max Phase: Preclinical

Molecular Formula: C18H18ClN5O2

Molecular Weight: 335.37

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Cc1cc2c(cc1O)/C(=C\c1cccc(/C=N/NC(=N)N)c1)C(=O)N2.Cl

Standard InChI:  InChI=1S/C18H17N5O2.ClH/c1-10-5-15-13(8-16(10)24)14(17(25)22-15)7-11-3-2-4-12(6-11)9-21-23-18(19)20;/h2-9,24H,1H3,(H,22,25)(H4,19,20,23);1H/b14-7+,21-9+;

Standard InChI Key:  XGXMHIFRLKVTTL-FBKASXLCSA-N

Molfile:  

     RDKit          2D

 26 27  0  0  0  0  0  0  0  0999 V2000
   19.2329   -7.5487    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   17.7333   -4.9072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7321   -5.7309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4402   -6.1399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1540   -5.7304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1511   -4.9036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4384   -4.4942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8664   -6.1379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5776   -5.7282    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.2901   -6.1357    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.0200   -6.1389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3085   -5.7298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0055   -5.4474    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.5560   -6.0591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3842   -6.8622    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.4188   -4.7358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2211   -4.9109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7662   -4.3016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5144   -3.5213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0013   -5.7260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.7138   -6.1335    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.0000   -4.9047    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.1624   -3.9642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7100   -3.3553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0600   -2.9129    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.4550   -2.5789    0.0000 C   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 24  1  0
 23 16  1  0
 10 20  1  0
 20 21  1  0
 20 22  2  0
 23 24  2  0
 19 25  1  0
 24 26  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: 335.37

Molecular Weight (Monoisotopic): 335.1382

AlogP: 2.01

#Rotatable Bonds: 3

Polar Surface Area: 123.59

Molecular Species: NEUTRAL

HBA: 4

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 9.54

CX Basic pKa: 6.70

CX LogP: 2.47

CX LogD: 2.39

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.19

Np Likeness Score: -0.54

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