(2E,5E)-2,5-bis(4-(azidomethyl)benzylidene)cyclopentanone

ID: ALA3104706

PubChem CID: 76317389

Max Phase: Preclinical

Molecular Formula: C21H18N6O

Molecular Weight: 370.42

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  [N-]=[N+]=NCc1ccc(/C=C2\CC/C(=C\c3ccc(CN=[N+]=[N-])cc3)C2=O)cc1

Standard InChI:  InChI=1S/C21H18N6O/c22-26-24-13-17-5-1-15(2-6-17)11-19-9-10-20(21(19)28)12-16-3-7-18(8-4-16)14-25-27-23/h1-8,11-12H,9-10,13-14H2/b19-11+,20-12+

Standard InChI Key:  BJNWGTZVQIDYPT-AYKLPDECSA-N

Molfile:  

     RDKit          2D

 28 30  0  0  0  0  0  0  0  0999 V2000
    7.1610  -28.2204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5138  -28.7228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7917  -29.4935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6105  -29.4675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8387  -28.6806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1349  -27.4016    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6094  -28.4028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2354  -28.9314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0907  -29.7377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7166  -30.2663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4873  -29.9884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6321  -29.1821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0061  -28.6535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1133  -30.5170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8840  -30.2391    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.5100  -30.7677    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.1359  -31.2962    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.7270  -28.4946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1359  -29.0619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3491  -28.8336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7580  -29.4009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9538  -30.1964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7406  -30.4247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3317  -29.8574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3627  -30.7637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5759  -30.5355    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9848  -31.1028    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3938  -31.6701    0.0000 N   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
  1  5  1  0
  1  6  2  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
  8 13  2  0
 15 16  2  0
 16 17  2  0
 14 15  1  0
 11 14  1  0
  5  7  2  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 19 24  2  0
 26 27  2  0
 27 28  2  0
 25 26  1  0
 22 25  1  0
  2 18  2  0
M  CHG  4  16   1  17  -1  27   1  28  -1
M  END

Alternative Forms

1. Parent:

   

   ALA3104706

   (2E,5E)-2,5-bis[[4-(azidomethyl)phenyl]methylidene]cyclopentan-1-one

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: 370.42

Molecular Weight (Monoisotopic): 370.1542

AlogP: 6.14

#Rotatable Bonds: 6

Polar Surface Area: 114.59

Molecular Species: NEUTRAL

HBA: 3

HBD: ┄

#RO5 Violations: 1

HBA (Lipinski): 7

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 5.26

CX LogD: 5.03

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.26

Np Likeness Score: -0.04

References

1. Braga SF, Alves ÉV, Ferreira RS, Fradico JR, Lage PS, Duarte MC, Ribeiro TG, Júnior PA, Romanha AJ, Tonini ML, Steindel M, Coelho EF, de Oliveira RB..  (2014)  Synthesis and evaluation of the antiparasitic activity of bis-(arylmethylidene) cycloalkanones.,  71  [PMID:24321832] [10.1016/j.ejmech.2013.11.011]

Source

Source(1):

• Scientific Literature