1,5-bis(3-bromophenyl)penta-1,4-dien-3-one

ID: ALA1088987

PubChem CID: 15426009

Max Phase: Preclinical

Molecular Formula: C17H12Br2O

Molecular Weight: 392.09

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(/C=C/c1cccc(Br)c1)/C=C/c1cccc(Br)c1

Standard InChI:  InChI=1S/C17H12Br2O/c18-15-5-1-3-13(11-15)7-9-17(20)10-8-14-4-2-6-16(19)12-14/h1-12H/b9-7+,10-8+

Standard InChI Key:  UCKYBKCMYSGBTI-FIFLTTCUSA-N

Molfile:  

     RDKit          2D

 20 21  0  0  0  0  0  0  0  0999 V2000
   -1.5322   -9.4445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2475   -9.0334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9612   -9.4470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6760   -9.0340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3892   -9.4470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3882  -10.2729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6681  -10.6838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9579  -10.2685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1042   -9.0355    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -0.1014   -9.4413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8171   -9.0257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6078   -9.0243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3238   -9.4340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3246  -10.2598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0397  -10.6694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7536  -10.2542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7478   -9.4249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0320   -9.0191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4591   -9.0073    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -0.8186   -8.2007    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0
  1 11  1  0
 10 11  1  0
  5  6  2  0
 10 12  2  0
  1  2  2  0
 12 13  1  0
  6  7  1  0
 13 14  2  0
  3  4  2  0
 14 15  1  0
  7  8  2  0
 15 16  2  0
  8  3  1  0
 16 17  1  0
 17 18  2  0
 18 13  1  0
  5  9  1  0
 17 19  1  0
  4  5  1  0
 11 20  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA1088987

   1,5-Bis(3-bromophenyl)penta-1,4-dien-3-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: 392.09

Molecular Weight (Monoisotopic): 389.9255

AlogP: 5.51

#Rotatable Bonds: 4

Polar Surface Area: 17.07

Molecular Species: NEUTRAL

HBA: 1

HBD: ┄

#RO5 Violations: 1

HBA (Lipinski): 1

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 6.36

CX LogD: 6.36

Aromatic Rings: 2

Heavy Atoms: 20

QED Weighted: 0.63

Np Likeness Score: -0.08

References

1. Hu GX, Liang G, Chu Y, Li X, Lian QQ, Lin H, He Y, Huang Y, Hardy DO, Ge RS..  (2010)  Curcumin derivatives inhibit testicular 17beta-hydroxysteroid dehydrogenase 3.,  20  (8): [PMID:20346654] [10.1016/j.bmcl.2010.02.089]

2. Francisco KR, Monti L, Yang W, Park H, Liu LJ, Watkins K, Amarasinghe DK, Nalli M, Roberto Polaquini C, Regasini LO, Eduardo Miller Crotti A, Silvestri R, Guidi Magalhães L, Caffrey CR..  (2023)  Structure-activity relationship of dibenzylideneacetone analogs against the neglected disease pathogen, Trypanosoma brucei.,  81  [PMID:36608774] [10.1016/j.bmcl.2023.129123]

Source

Source(1):

• Scientific Literature