2-(2-Methyl-5-nitro-1H-imidazol-1-yl)ethyl (2,2,2-trichloro-1-(6-chloro-2-fluoro-9H-purin-9-yl)ethyl)carbamate

ID: ALA4476033

PubChem CID: 155538057

Max Phase: Preclinical

Molecular Formula: C14H11Cl4FN8O4

Molecular Weight: 516.10

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Cc1ncc([N+](=O)[O-])n1CCOC(=O)NC(n1cnc2c(Cl)nc(F)nc21)C(Cl)(Cl)Cl

Standard InChI:  InChI=1S/C14H11Cl4FN8O4/c1-6-20-4-7(27(29)30)25(6)2-3-31-13(28)24-11(14(16,17)18)26-5-21-8-9(15)22-12(19)23-10(8)26/h4-5,11H,2-3H2,1H3,(H,24,28)

Standard InChI Key:  WCFPPFOJGUJESL-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 31 33  0  0  0  0  0  0  0  0999 V2000
   35.2773  -26.5812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.5615  -26.9914    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   33.8462  -26.5801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.1304  -26.9903    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   33.8469  -25.7545    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.4153  -26.5790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.6994  -26.9891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.9883  -26.5779    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   30.9053  -25.7546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.0978  -25.5833    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   29.6824  -26.2985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.2357  -26.9093    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.5170  -25.2023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.0594  -27.7224    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   30.6733  -28.2769    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.2779  -27.9793    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   35.2780  -25.7557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.9938  -25.3414    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   34.5627  -25.3402    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   35.2714  -24.9289    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   35.9925  -26.9925    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   36.1605  -27.8026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.9831  -27.8960    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   36.7112  -26.5837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.3170  -27.1411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.1010  -26.8885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.2763  -26.0830    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   37.6655  -25.5307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.8838  -25.7820    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   38.7095  -27.4403    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   37.8384  -24.7277    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
 21  1  1  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  3  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12  8  1  0
  9 13  1  0
 14 15  2  0
 14 16  1  0
 12 14  1  0
  1 17  1  0
 17 18  1  0
 17 19  1  0
 17 20  1  0
 24 21  1  0
 21 22  1  0
 22 23  2  0
 23 25  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 29 24  1  0
 26 30  1  0
 28 31  1  0
M  CHG  2  14   1  16  -1
M  END

Alternative Forms

1. Parent:

   

   ALA4476033

   ---

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: 516.10

Molecular Weight (Monoisotopic): 513.9641

AlogP: 3.33

#Rotatable Bonds: 6

Polar Surface Area: 142.89

Molecular Species: NEUTRAL

HBA: 10

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 12

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 10.93

CX Basic pKa: 3.27

CX LogP: 2.97

CX LogD: 2.97

Aromatic Rings: 3

Heavy Atoms: 31

QED Weighted: 0.17

Np Likeness Score: -1.30

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