2-(2-Methyl-5-nitro-1H-imidazol-1-yl)ethyl (2,2,2-trichloro-1-(isoquinolin-3-ylamino)ethyl)carbamate

ID: ALA4525670

PubChem CID: 155543266

Max Phase: Preclinical

Molecular Formula: C18H17Cl3N6O4

Molecular Weight: 487.73

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Cc1ncc([N+](=O)[O-])n1CCOC(=O)NC(Nc1cc2ccccc2cn1)C(Cl)(Cl)Cl

Standard InChI:  InChI=1S/C18H17Cl3N6O4/c1-11-22-10-15(27(29)30)26(11)6-7-31-17(28)25-16(18(19,20)21)24-14-8-12-4-2-3-5-13(12)9-23-14/h2-5,8-10,16H,6-7H2,1H3,(H,23,24)(H,25,28)

Standard InChI Key:  QAUXBDQGNSEMTD-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 31 33  0  0  0  0  0  0  0  0999 V2000
   35.0817  -18.4613    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.3657  -18.8716    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   33.6505  -18.4602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.9346  -18.8705    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   32.2192  -18.4591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.5034  -18.8693    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.2199  -17.6335    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.7922  -18.4580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.0763  -18.8682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.3610  -18.4569    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   29.2780  -17.6336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.4704  -17.4622    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   28.0549  -18.1775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.6084  -18.7883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.8898  -17.0812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.4361  -19.6014    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   29.0460  -20.1561    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.6504  -19.8585    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   33.6512  -17.6346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.3670  -17.2202    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   32.9358  -17.2191    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   33.6445  -16.8077    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   35.7937  -18.8758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.7899  -17.2244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.0775  -17.6405    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   36.5102  -17.6398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.5089  -18.4655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.2187  -18.8756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.9344  -18.4652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.9317  -17.6364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.2172  -17.2258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  5  7  2  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 10  1  0
 11 15  1  0
 16 17  2  0
 16 18  1  0
 14 16  1  0
  3 19  1  0
 19 20  1  0
 19 21  1  0
 19 22  1  0
  1 23  2  0
 23 27  1  0
 26 24  1  0
 24 25  2  0
 25  1  1  0
 26 27  1  0
 27 28  2  0
 28 29  1  0
 29 30  2  0
 30 31  1  0
 31 26  2  0
M  CHG  2  16   1  18  -1
M  END

Alternative Forms

1. Parent:

   

   ALA4525670

   ---

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: 487.73

Molecular Weight (Monoisotopic): 486.0377

AlogP: 4.18

#Rotatable Bonds: 7

Polar Surface Area: 124.21

Molecular Species: NEUTRAL

HBA: 8

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 10

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.19

CX Basic pKa: 6.46

CX LogP: 3.41

CX LogD: 3.37

Aromatic Rings: 3

Heavy Atoms: 31

QED Weighted: 0.22

Np Likeness Score: -1.29

References

1. Huang P, Le X, Huang F, Yang J, Yang H, Ma J, Hu G, Li Q, Chen Z..  (2020)  Discovery of a Dual Tubulin Polymerization and Cell Division Cycle 20 Homologue Inhibitor via Structural Modification on Apcin.,  63  (9): [PMID:32290657] [10.1021/acs.jmedchem.9b02097]

Source

Source(1):

• Scientific Literature