(2E,5E)-2,5-Bis(2-fluorobenzylidene)cyclopentanone

ID: ALA517667

PubChem CID: 20416677

Max Phase: Preclinical

Molecular Formula: C20H16F2O

Molecular Weight: 310.34

Molecule Type: Small molecule

Associated Items:

This compound is not in our inventory system

Names and Identifiers

Synonyms: 2,6-Bis(2-Fluorobenzylidene)Cyclohexanone | 2,6-Bis(2-Fluorobenzylidene)Cyclohexanone|CHEMBL517667|AKOS001493635|(2E,6E)-2,6-bis[(2-fluorophenyl)methylidene]cyclohexan-1-one

Canonical SMILES:  O=C1/C(=C/c2ccccc2F)CCC/C1=C\c1ccccc1F

Standard InChI:  InChI=1S/C20H16F2O/c21-18-10-3-1-6-14(18)12-16-8-5-9-17(20(16)23)13-15-7-2-4-11-19(15)22/h1-4,6-7,10-13H,5,8-9H2/b16-12+,17-13+

Standard InChI Key:  WIDDWATUDMOWCU-UNZYHPAISA-N

Molfile:  

     RDKit          2D

 23 25  0  0  0  0  0  0  0  0999 V2000
    1.7604  -19.4767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4747  -19.8806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0843  -19.4647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7903  -19.8640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4965  -19.4448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2103  -19.8455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2286  -20.6719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5196  -21.0950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8015  -20.6914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4811  -20.7055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1946  -21.1094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9075  -20.6809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9010  -19.8706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1810  -19.4636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3475  -18.6536    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3451  -19.4643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3739  -19.8801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3733  -20.7061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3446  -21.1225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0637  -20.7067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0648  -19.8745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4866  -18.6203    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    3.1733  -18.6390    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
 10 11  1  0
 21  1  2  0
 11 12  2  0
  5  6  1  0
 12 13  1  0
 17  3  2  0
 13 14  2  0
 14  2  1  0
  6  7  2  0
 16 15  2  0
 16 17  1  0
  7  8  1  0
  3  4  1  0
  8  9  2  0
  9  4  1  0
  1  2  1  0
 16 21  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
  2 10  2  0
  5 22  1  0
  4  5  2  0
 14 23  1  0
M  END

Alternative Forms

Associated Targets(Human)

CNE (323 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HL-60 (67320 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
PC-3 (62116 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HeLa (62764 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
TYR Tclin Tyrosinase (717 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
U2OS (164939 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
A549 (127892 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
NCI-H460 (60772 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Associated Targets(non-human)

RAW264.7 (28094 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Molecule Features

Natural Product: NoOral: NoChemical Probe: NoParenteral: No
Molecule Type: Small moleculeTopical: NoFirst In Class: NoBlack Box: No
Chirality: NoAvailability: NoProdrug: No

Drug Indications

MESH IDMESH Heading EFO IDsEFO TermsMax Phase for IndicationReferences

Mechanisms of Action

Mechanism of ActionAction Typetarget IDTarget NameTarget TypeTarget OrganismBinding Site NameReferences

Calculated Properties

Molecular Weight: 310.34Molecular Weight (Monoisotopic): 310.1169AlogP: 5.18#Rotatable Bonds: 2
Polar Surface Area: 17.07Molecular Species: HBA: 1HBD:
#RO5 Violations: 1HBA (Lipinski): 1HBD (Lipinski): #RO5 Violations (Lipinski): 1
CX Acidic pKa: CX Basic pKa: CX LogP: 5.88CX LogD: 5.88
Aromatic Rings: 2Heavy Atoms: 23QED Weighted: 0.70Np Likeness Score: -0.75

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. Lee KH, Ab Aziz FH, Syahida A, Abas F, Shaari K, Israf DA, Lajis NH..  (2009)  Synthesis and biological evaluation of curcumin-like diarylpentanoid analogues for anti-inflammatory, antioxidant and anti-tyrosinase activities.,  44  (8): [PMID:19359068] [10.1016/j.ejmech.2009.03.020]
3. Leow PC, Bahety P, Boon CP, Lee CY, Tan KL, Yang T, Ee PL..  (2014)  Functionalized curcumin analogs as potent modulators of the Wnt/β-catenin signaling pathway.,  71  [PMID:24275249] [10.1016/j.ejmech.2013.10.073]
4. Tan KL, Ali A, Du Y, Fu H, Jin HX, Chin TM, Khan M, Go ML..  (2014)  Synthesis and evaluation of bisbenzylidenedioxotetrahydrothiopranones as activators of endoplasmic reticulum (ER) stress signaling pathways and apoptotic cell death in acute promyelocytic leukemic cells.,  57  (14): [PMID:24960549] [10.1021/jm401352a]
5. Moreira J, Saraiva L, Pinto MM, Cidade H..  (2020)  Diarylpentanoids with antitumor activity: A critical review of structure-activity relationship studies.,  192  [PMID:32172081] [10.1016/j.ejmech.2020.112177]

Source