(E)-2-((2-Chloro-1-cinnamyl-1H-indol-3-yl)methylene)hydrazine-1-carboximidamide Hydrochloride

ID: ALA4475806

PubChem CID: 155537961

Max Phase: Preclinical

Molecular Formula: C19H19Cl2N5

Molecular Weight: 351.84

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Cl.N=C(N)N/N=C/c1c(Cl)n(C/C=C/c2ccccc2)c2ccccc12

Standard InChI:  InChI=1S/C19H18ClN5.ClH/c20-18-16(13-23-24-19(21)22)15-10-4-5-11-17(15)25(18)12-6-9-14-7-2-1-3-8-14;/h1-11,13H,12H2,(H4,21,22,24);1H/b9-6+,23-13+;

Standard InChI Key:  JDGOYUVQDRZNOQ-JNDHEHSGSA-N

Molfile:  

     RDKit          2D

 26 27  0  0  0  0  0  0  0  0999 V2000
    5.8730  -18.0277    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    4.2414  -14.9694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2402  -15.7890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9483  -16.1979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9465  -14.5606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6551  -14.9658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6554  -15.7844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4340  -16.0372    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.9150  -15.3747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4336  -14.7127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6859  -13.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4851  -13.7652    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.7374  -12.9879    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.5367  -12.8178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7889  -12.0405    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.0837  -13.4249    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.7322  -15.3744    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    6.6868  -16.8143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4861  -16.9840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7389  -17.7611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5383  -17.9308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7890  -18.7075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5876  -18.8773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1351  -18.2695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8786  -17.4892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0806  -17.3230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  2  0
  3  4  1  0
  4  7  2  0
  6  5  2  0
  5  2  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10  6  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  2  0
  9 17  1  0
  8 18  1  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 21  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: 351.84

Molecular Weight (Monoisotopic): 351.1251

AlogP: 3.83

#Rotatable Bonds: 5

Polar Surface Area: 79.19

Molecular Species: NEUTRAL

HBA: 3

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 8.01

CX LogP: 3.94

CX LogD: 3.25

Aromatic Rings: 3

Heavy Atoms: 25

QED Weighted: 0.37

Np Likeness Score: -0.90

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