(5Z)-4-bromo-5-(bromomethylene)-3-butyl-2(5H)-furanone

ID: ALA448241

Max Phase: Preclinical

Molecular Formula: C9H10Br2O2

Molecular Weight: 309.99

Molecule Type: Small molecule

Associated Items:

Representations

Canonical SMILES:  CCCCC1=C(Br)/C(=C/Br)OC1=O

Standard InChI:  InChI=1S/C9H10Br2O2/c1-2-3-4-6-8(11)7(5-10)13-9(6)12/h5H,2-4H2,1H3/b7-5-

Standard InChI Key:  UVJAGAXWVHGYRW-ALCCZGGFSA-N

Associated Targets(Human)

HT-1080 (3966 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Lu1 (576 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
KB (17409 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
A-431 (6446 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
LNCaP (8286 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ZR-75-1 (953 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Associated Targets(non-human)

P388 (20296 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Escherichia coli (133304 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Micrococcus luteus (7463 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Bacillus subtilis (32866 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Penicillium oxalicum (133 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Plasmodium falciparum (966862 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
luxS S-ribosylhomocysteine lyase (18 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Salmonella typhimurium (15756 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Vibrio harveyi (399 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Staphylococcus epidermidis (22802 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Staphylococcus aureus (210822 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Pseudomonas aeruginosa (123386 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
L929 (3802 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: 309.99Molecular Weight (Monoisotopic): 307.9048AlogP: 3.62#Rotatable Bonds: 3
Polar Surface Area: 26.30Molecular Species: HBA: 2HBD: 0
#RO5 Violations: 0HBA (Lipinski): 2HBD (Lipinski): 0#RO5 Violations (Lipinski): 0
CX Acidic pKa: CX Basic pKa: CX LogP: 3.37CX LogD: 3.37
Aromatic Rings: 0Heavy Atoms: 13QED Weighted: 0.74Np Likeness Score: 1.96

References

1. Wright AD, de Nys R, Angerhofer CK, Pezzuto JM, Gurrath M..  (2006)  Biological activities and 3D QSAR studies of a series of Delisea pulchra (cf. fimbriata) derived natural products.,  69  (8): [PMID:16933872] [10.1021/np050510c]
2. Zang T, Lee BW, Cannon LM, Ritter KA, Dai S, Ren D, Wood TK, Zhou ZS..  (2009)  A naturally occurring brominated furanone covalently modifies and inactivates LuxS.,  19  (21): [PMID:19775890] [10.1016/j.bmcl.2009.08.095]
3. Steenackers HP, Levin J, Janssens JC, De Weerdt A, Balzarini J, Vanderleyden J, De Vos DE, De Keersmaecker SC..  (2010)  Structure-activity relationship of brominated 3-alkyl-5-methylene-2(5H)-furanones and alkylmaleic anhydrides as inhibitors of Salmonella biofilm formation and quorum sensing regulated bioluminescence in Vibrio harveyi.,  18  (14): [PMID:20580562] [10.1016/j.bmc.2010.05.055]
4. Kuehl R, Al-Bataineh S, Gordon O, Luginbuehl R, Otto M, Textor M, Landmann R..  (2009)  Furanone at subinhibitory concentrations enhances staphylococcal biofilm formation by luxS repression.,  53  (10): [PMID:19620329] [10.1128/aac.01704-08]
5. Kutty SK, Barraud N, Pham A, Iskander G, Rice SA, Black DS, Kumar N..  (2013)  Design, synthesis, and evaluation of fimbrolide-nitric oxide donor hybrids as antimicrobial agents.,  56  (23): [PMID:24191659] [10.1021/jm400951f]
6. Sabbah M, Bernollin M, Doutheau A, Soulere L, Queneau Y.  (2013)  A new route towards fimbrolide analogues: importance of the exomethylene motif in LuxR dependent quorum sensing inhibition,  (2): [10.1039/C2MD20298K]
7. Husain A, Khan SA, Iram F, Iqbal MA, Asif M..  (2019)  Insights into the chemistry and therapeutic potential of furanones: A versatile pharmacophore.,  171  [PMID:30909021] [10.1016/j.ejmech.2019.03.021]
8. Chen J, Lu Y, Ye X, Emam M, Zhang H, Wang H..  (2020)  Current advances in Vibrio harveyi quorum sensing as drug discovery targets.,  207  [PMID:32871343] [10.1016/j.ejmech.2020.112741]

Source