2-((4-Methylpiperazin-1-yl)methyl)-1H-anthra[1,2-d]imidazole-6,11-dione

ID: ALA2336666

PubChem CID: 53372753

Max Phase: Preclinical

Molecular Formula: C21H20N4O2

Molecular Weight: 360.42

Molecule Type: Small molecule

Names and Identifiers

Synonyms: NSC-749235 | CHEMBL2336666|NSC-749235|SCHEMBL710529|BDBM50428823

Canonical SMILES:  CN1CCN(Cc2nc3ccc4c(c3[nH]2)C(=O)c2ccccc2C4=O)CC1

Standard InChI:  InChI=1S/C21H20N4O2/c1-24-8-10-25(11-9-24)12-17-22-16-7-6-15-18(19(16)23-17)21(27)14-5-3-2-4-13(14)20(15)26/h2-7H,8-12H2,1H3,(H,22,23)

Standard InChI Key:  FMYMGQTUHIDMGD-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   23.0862  -28.5281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6511  -28.5285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6551  -27.7035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9466  -27.2897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9385  -28.9397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2253  -28.5214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2254  -27.6980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5163  -27.2884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8027  -27.6978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8026  -28.5212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5161  -28.9352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9522  -26.4624    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.9354  -29.7670    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.3659  -27.2850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0827  -27.6944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.6935  -27.1392    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.3543  -26.3866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.5339  -26.4769    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.7645  -25.6683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.5917  -25.6644    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   25.0064  -26.3812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.8301  -26.3792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.2441  -25.6627    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   25.8284  -24.9465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.9985  -24.9467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.0713  -25.6618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  1  0
  1  2  2  0
  2 16  1  0
 15  4  1  0
  3  4  2  0
  3  6  1  0
  4  5  1  0
  5  8  1  0
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  7  8  2  0
  7 12  1  0
  8  9  1  0
  9 10  2  0
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  5 13  2  0
  6 14  2  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 15  1  0
 18 20  1  0
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 21 22  1  0
 21 26  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 24 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2336666

   2-[(4-methylpiperazin-1-yl)methyl]-3H-naphtho[3,2-e]benzimidazole-6,11-dione

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: 360.42

Molecular Weight (Monoisotopic): 360.1586

AlogP: 2.09

#Rotatable Bonds: 2

Polar Surface Area: 69.30

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.86

CX Basic pKa: 6.76

CX LogP: 2.07

CX LogD: 1.96

Aromatic Rings: 3

Heavy Atoms: 27

QED Weighted: 0.59

Np Likeness Score: -0.70

References

1. Chen CL, Chang DM, Chen TC, Lee CC, Hsieh HH, Huang FC, Huang KF, Guh JH, Lin JJ, Huang HS..  (2013)  Structure-based design, synthesis and evaluation of novel anthra[1,2-d]imidazole-6,11-dione derivatives as telomerase inhibitors and potential for cancer polypharmacology.,  60  [PMID:23279865] [10.1016/j.ejmech.2012.11.032]

Source

Source(1):

• Scientific Literature