3-(3,4-Dihydroxy-phenyl)-1-phenyl-propenone

ID: ALA129510

Chembl Id: CHEMBL129510

Cas Number: 72704-76-8

PubChem CID: 6474896

Max Phase: Preclinical

Molecular Formula: C15H12O3

Molecular Weight: 240.26

Molecule Type: Small molecule

Associated Items:

Names and Identifiers

Synonyms: 3,4-Dihydroxychalcone | 3,4-DIHYDROXYCHALCONE|Antioxidant agent-1|(E)-3-(3,4-dihydroxyphenyl)-1-phenylprop-2-en-1-one|CHEMBL129510|72704-76-8|136068-43-4|3-(3,4-Dihydroxyphenyl)-1-phenylprop-2-en-1-one|SCHEMBL1878031|SCHEMBL4972250|BDBM50042963|MS-23402|HY-145104|CS-0356367|3-(3,4-Dihydroxy-phenyl)-1-phenyl-propenone|(E)-3-(3,4-Dihydroxy-phenyl)-1-phenyl-propenone|2-Propen-1-one,3-(3,4-dihydroxyphenyl)-1-phenyl-|(E)-3-(3,4-dihydroxyphenyl)-1-phenyl-prop-2-en-1-one

Canonical SMILES:  O=C(/C=C/c1ccc(O)c(O)c1)c1ccccc1

Standard InChI:  InChI=1S/C15H12O3/c16-13(12-4-2-1-3-5-12)8-6-11-7-9-14(17)15(18)10-11/h1-10,17-18H/b8-6+

Standard InChI Key:  HHKVOYUYPYZFHJ-SOFGYWHQSA-N

Alternative Forms

  1. Parent:

Associated Targets(Human)

MT4 (17854 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
KB (17409 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Associated Targets(non-human)

pol Human immunodeficiency virus type 1 integrase (9041 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Alox5 Arachidonate 5-lipoxygenase (2865 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Rattus norvegicus (775804 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
amyS Alpha-amylase (22 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
BMY1 Beta-amylase (20 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Candida albicans (78123 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Staphylococcus aureus (210822 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Escherichia coli (133304 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Saccharomyces cerevisiae (19171 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Ogataea angusta (372 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Kluyveromyces lactis (70 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
MDCK (10148 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Ptgs2 Cyclooxygenase (970 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
XDH Xanthine dehydrogenase (2296 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: 240.26Molecular Weight (Monoisotopic): 240.0786AlogP: 2.99#Rotatable Bonds: 3
Polar Surface Area: 57.53Molecular Species: NEUTRALHBA: 3HBD: 2
#RO5 Violations: HBA (Lipinski): 3HBD (Lipinski): 2#RO5 Violations (Lipinski):
CX Acidic pKa: 9.00CX Basic pKa: CX LogP: 3.28CX LogD: 3.27
Aromatic Rings: 2Heavy Atoms: 18QED Weighted: 0.49Np Likeness Score: 0.51

References

1. Sogawa S, Nihro Y, Ueda H, Izumi A, Miki T, Matsumoto H, Satoh T..  (1993)  3,4-Dihydroxychalcones as potent 5-lipoxygenase and cyclooxygenase inhibitors.,  36  (24): [PMID:8254620] [10.1021/jm00076a019]
2. Artico M, Di Santo R, Costi R, Novellino E, Greco G, Massa S, Tramontano E, Marongiu ME, De Montis A, La Colla P..  (1998)  Geometrically and conformationally restrained cinnamoyl compounds as inhibitors of HIV-1 integrase: synthesis, biological evaluation, and molecular modeling.,  41  (21): [PMID:9767632] [10.1021/jm9707232]
3. Buolamwini JK, Assefa H..  (2002)  CoMFA and CoMSIA 3D QSAR and docking studies on conformationally-restrained cinnamoyl HIV-1 integrase inhibitors: exploration of a binding mode at the active site.,  45  (4): [PMID:11831895] [10.1021/jm010399h]
4. Seo WD, Kim JH, Kang JE, Ryu HW, Curtis-Long MJ, Lee HS, Yang MS, Park KH..  (2005)  Sulfonamide chalcone as a new class of alpha-glucosidase inhibitors.,  15  (24): [PMID:16202584] [10.1016/j.bmcl.2005.08.087]
5. Batovska D, Parushev S, Slavova A, Bankova V, Tsvetkova I, Ninova M, Najdenski H..  (2007)  Study on the substituents' effects of a series of synthetic chalcones against the yeast Candida albicans.,  42  (1): [PMID:17007965] [10.1016/j.ejmech.2006.08.012]
6. Lahtchev KL, Batovska DI, Parushev SP, Ubiyvovk VM, Sibirny AA..  (2008)  Antifungal activity of chalcones: a mechanistic study using various yeast strains.,  43  (10): [PMID:18280009] [10.1016/j.ejmech.2007.12.027]
7. Batovska D, Parushev S, Stamboliyska B, Tsvetkova I, Ninova M, Najdenski H..  (2009)  Examination of growth inhibitory properties of synthetic chalcones for which antibacterial activity was predicted.,  44  (5): [PMID:18584918] [10.1016/j.ejmech.2008.05.010]
8. Fioravanti R, Celestino I, Costi R, Cuzzucoli Crucitti G, Pescatori L, Mattiello L, Novellino E, Checconi P, Palamara AT, Nencioni L, Di Santo R..  (2012)  Effects of polyphenol compounds on influenza A virus replication and definition of their mechanism of action.,  20  (16): [PMID:22743086] [10.1016/j.bmc.2012.05.062]
9. Sharma MC.  (2013)  Molecular modeling studies of substituted 3,4-dihydroxychalcone derivatives as 5-lipoxygenase and cyclooxygenase inhibitors,  [10.1007/s00044-013-0745-7]
10. Hofmann E, Webster J, Do T, Kline R, Snider L, Hauser Q, Higginbottom G, Campbell A, Ma L, Paula S..  (2016)  Hydroxylated chalcones with dual properties: Xanthine oxidase inhibitors and radical scavengers.,  24  (4): [PMID:26762836] [10.1016/j.bmc.2015.12.024]

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