(2E,5E)-2,5-bis(2-bromobenzylidene)cyclopentanone

ID: ALA476847

PubChem CID: 12033869

Max Phase: Preclinical

Molecular Formula: C19H14Br2O

Molecular Weight: 418.13

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C1/C(=C/c2ccccc2Br)CC/C1=C\c1ccccc1Br

Standard InChI:  InChI=1S/C19H14Br2O/c20-17-7-3-1-5-13(17)11-15-9-10-16(19(15)22)12-14-6-2-4-8-18(14)21/h1-8,11-12H,9-10H2/b15-11+,16-12+

Standard InChI Key:  VRZWMEJYNBXWDD-JOBJLJCHSA-N

Molfile:  

     RDKit          2D

 22 24  0  0  0  0  0  0  0  0999 V2000
   12.0458   -0.2834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8708   -0.2834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1276    0.5008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4583    0.9875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7933    0.5008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9126    0.7546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5249    0.2017    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0085    0.7554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3957    0.2030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6118    0.4601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9993   -0.0914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1709   -0.8993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9605   -1.1526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5697   -0.5994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3499   -0.6031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9614   -1.1557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7474   -0.9020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9183   -0.0906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3055    0.4585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4570    1.8125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.4414    1.2673    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   15.4745    1.2660    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
 10 11  1  0
  1  2  1  0
 11 12  2  0
  3  6  2  0
 12 13  1  0
 13 14  2  0
 14  9  1  0
  6  7  1  0
  7 15  2  0
  2  3  1  0
 15 16  1  0
  5  8  2  0
 16 17  2  0
  3  4  1  0
 17 18  1  0
  8  9  1  0
 18 19  2  0
 19  7  1  0
  4  5  1  0
  4 20  2  0
  9 10  2  0
 10 21  1  0
  5  1  1  0
 19 22  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA476847

   (2E,5E)-2,5-bis(2-bromobenzylidene)cyclopentanone

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: 418.13

Molecular Weight (Monoisotopic): 415.9411

AlogP: 6.04

#Rotatable Bonds: 2

Polar Surface Area: 17.07

Molecular Species: ┄

HBA: 1

HBD: ┄

#RO5 Violations: 1

HBA (Lipinski): 1

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 6.69

CX LogD: 6.69

Aromatic Rings: 2

Heavy Atoms: 22

QED Weighted: 0.54

Np Likeness Score: -0.46

References

1. Liang G, Shao L, Wang Y, Zhao C, Chu Y, Xiao J, Zhao Y, Li X, Yang S..  (2009)  Exploration and synthesis of curcumin analogues with improved structural stability both in vitro and in vivo as cytotoxic agents.,  17  (6): [PMID:19243951] [10.1016/j.bmc.2008.10.044]

2. Lin H, Hu GX, Guo J, Ge Y, Liang G, Lian QQ, Chu Y, Yuan X, Huang P, Ge RS..  (2013)  Mono-carbonyl curcumin analogues as 11β-hydroxysteroid dehydrogenase 1 inhibitors.,  23  (15): [PMID:23800686] [10.1016/j.bmcl.2013.05.080]

3. Moreira J, Durães F, Freitas-Silva J, Szemerédi N, Resende DISP, Pinto E, da Costa PM, Pinto M, Spengler G, Cidade H, Sousa E..  (2022)  New diarylpentanoids and chalcones as potential antimicrobial adjuvants.,  67  [PMID:35447343] [10.1016/j.bmcl.2022.128743]

Source

Source(1):

• Scientific Literature