ID: ALA1801961

Max Phase: Preclinical

Molecular Formula: C16H11F3O

Molecular Weight: 276.26

Molecule Type: Small molecule

Associated Items:

Representations

Canonical SMILES:  O=C(/C=C/c1ccccc1C(F)(F)F)c1ccccc1

Standard InChI:  InChI=1S/C16H11F3O/c17-16(18,19)14-9-5-4-6-12(14)10-11-15(20)13-7-2-1-3-8-13/h1-11H/b11-10+

Standard InChI Key:  NUNGHCGIWAQKCC-ZHACJKMWSA-N

Associated Targets(Human)

Nuclear factor erythroid 2-related factor 2 95332 Activities

Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Androgen Receptor 11781 Activities

Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

HT-29 80576 Activities

Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

SGC-7901 2773 Activities

Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

A2780 11979 Activities

Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

MSTO-211H 316 Activities

Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Associated Targets(non-human)

Mus musculus 284745 Activities

Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Cyclooxygenase 970 Activities

Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Arachidonate 5-lipoxygenase 2865 Activities

Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

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

Properties

Molecular Weight: 276.26Molecular Weight (Monoisotopic): 276.0762AlogP: 4.60#Rotatable Bonds: 3
Polar Surface Area: 17.07Molecular Species: NEUTRALHBA: 1HBD: 0
#RO5 Violations: 0HBA (Lipinski): 1HBD (Lipinski): 0#RO5 Violations (Lipinski): 0
CX Acidic pKa: CX Basic pKa: CX LogP: 4.77CX LogD: 4.77
Aromatic Rings: 2Heavy Atoms: 20QED Weighted: 0.59Np Likeness Score: -0.65

References

1. Kumar V, Kumar S, Hassan M, Wu H, Thimmulappa RK, Kumar A, Sharma SK, Parmar VS, Biswal S, Malhotra SV..  (2011)  Novel chalcone derivatives as potent Nrf2 activators in mice and human lung epithelial cells.,  54  (12): [PMID:21539383] [10.1021/jm2002348]
2. Kim YS, Kumar V, Lee S, Iwai A, Neckers L, Malhotra SV, Trepel JB..  (2012)  Methoxychalcone inhibitors of androgen receptor translocation and function.,  22  (5): [PMID:22310230] [10.1016/j.bmcl.2011.12.141]
3. Wu J, Wang C, Cai Y, Peng J, Liang D, Zhao Y, Yang S, Li X, Wu X, Liang G.  (2012)  Synthesis and crystal structure of chalcones as well as on cytotoxicity and antibacterial properties,  21  (4): [10.1007/s00044-011-9549-9]
4. Sharma MC.  (2013)  Molecular modeling studies of substituted 3,4-dihydroxychalcone derivatives as 5-lipoxygenase and cyclooxygenase inhibitors,  [10.1007/s00044-013-0745-7]
5. Bist G, Pun NT, Magar TB, Shrestha A, Oh HJ, Khakurel A, Park PH, Lee ES..  (2017)  Inhibition of LPS-stimulated ROS production by fluorinated and hydroxylated chalcones in RAW 264.7 macrophages with structure-activity relationship study.,  27  (5): [PMID:28159411] [10.1016/j.bmcl.2017.01.061]
6. Iacovino LG, Pinzi L, Facchetti G, Bortolini B, Christodoulou MS, Binda C, Rastelli G, Rimoldi I, Passarella D, Di Paolo ML, Dalla Via L..  (2021)  Promising Non-cytotoxic Monosubstituted Chalcones to Target Monoamine Oxidase-B.,  12  (7.0): [PMID:34262643] [10.1021/acsmedchemlett.1c00238]

Source