2',4'-DIHYDROXYCHALCONE

ID: ALA105310

Max Phase: Preclinical

Molecular Formula: C15H12O3

Molecular Weight: 240.26

Molecule Type: Small molecule

Associated Items:

Representations

Synonyms (2): (E)-2',4'-Dihydroxychalcone | 2',4'-Dihydroxychalcone
Synonyms from Alternative Forms(2):

    Canonical SMILES:  O=C(/C=C/c1ccccc1)c1ccc(O)cc1O

    Standard InChI:  InChI=1S/C15H12O3/c16-12-7-8-13(15(18)10-12)14(17)9-6-11-4-2-1-3-5-11/h1-10,16,18H/b9-6+

    Standard InChI Key:  JUMSUVHHUVPSOY-RMKNXTFCSA-N

    Associated Targets(Human)

    MCF7 126967 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    PANC-1 6144 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    A549 127892 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    HeLa 62764 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    HT-1080 3966 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    U-937 7138 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Thyroid hormone receptor beta-1 7926 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Endoplasmic reticulum-associated amyloid beta-peptide-binding protein 20669 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Lysine-specific demethylase 4D-like 40243 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Survival motor neuron protein 34246 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Tyrosyl-DNA phosphodiesterase 1 345557 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Microtubule-associated protein tau 95507 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Aldehyde dehydrogenase 1A1 77053 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Arachidonate 15-lipoxygenase 7108 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    MAP kinase ERK2 25055 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Menin/Histone-lysine N-methyltransferase MLL 48157 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    15-hydroxyprostaglandin dehydrogenase [NAD+] 24926 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Cytochrome P450 3A4 53859 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    PC-3 62116 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    SK-MEL-28 48833 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    LoVo 4724 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Vitamin D receptor 26531 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Ubiquitin carboxyl-terminal hydrolase 1 22556 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    ATP-binding cassette sub-family G member 2 4927 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    P-glycoprotein 1 14716 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Multidrug resistance-associated protein 1 2587 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    78 kDa glucose-regulated protein 3319 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    HEK293 82097 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    MDA-MB-231 73002 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    BJ 6930 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Ca-Ski 420 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Associated Targets(non-human)

    Arachidonate 5-lipoxygenase 2865 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Rattus norvegicus 775804 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Tyrosinase 3884 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Colletotrichum truncatum 198 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Diaporthe longicolla 11 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Mycolicibacterium smegmatis 8003 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Mycobacterium tuberculosis 203094 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Glutathione reductase homolog 5 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Nuclear receptor ROR-gamma 89407 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    3T3-L1 3664 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    RAW264.7 28094 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Macrophomina phaseolina 474 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Fusarium graminearum 1554 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Fusarium equiseti 38 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Alternaria alternata 757 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Aldose reductase 4007 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Cyclooxygenase 970 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Leishmania amazonensis 3813 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Xanthine dehydrogenase 2296 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Streptococcus mutans 2687 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    GroEL/GroES 1042 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    HT-22 3261 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    SARS-CoV-2 38078 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    C2C12 756 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Staphylococcus aureus 210822 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: 240.26Molecular Weight (Monoisotopic): 240.0786AlogP: 2.99#Rotatable Bonds: 3
    Polar Surface Area: 57.53Molecular Species: NEUTRALHBA: 3HBD: 2
    #RO5 Violations: 0HBA (Lipinski): 3HBD (Lipinski): 2#RO5 Violations (Lipinski): 0
    CX Acidic pKa: 7.12CX Basic pKa: CX LogP: 3.93CX LogD: 3.46
    Aromatic Rings: 2Heavy Atoms: 18QED Weighted: 0.64Np Likeness Score: 0.61

    References

    1. Pouget C, Lauthier F, Simon A, Fagnere C, Basly JP, Delage C, Chulia AJ..  (2001)  Flavonoids: structural requirements for antiproliferative activity on breast cancer cells.,  11  (24): [PMID:11720850] [10.1016/s0960-894x(01)00617-5]
    2. 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]
    3. Jun N, Hong G, Jun K..  (2007)  Synthesis and evaluation of 2',4',6'-trihydroxychalcones as a new class of tyrosinase inhibitors.,  15  (6): [PMID:17267225] [10.1016/j.bmc.2007.01.017]
    4. Nowakowska Z..  (2007)  A review of anti-infective and anti-inflammatory chalcones.,  42  (2): [PMID:17112640] [10.1016/j.ejmech.2006.09.019]
    5. Awale S, Li F, Onozuka H, Esumi H, Tezuka Y, Kadota S..  (2008)  Constituents of Brazilian red propolis and their preferential cytotoxic activity against human pancreatic PANC-1 cancer cell line in nutrient-deprived condition.,  16  (1): [PMID:17950610] [10.1016/j.bmc.2007.10.004]
    6. Li F, Awale S, Tezuka Y, Kadota S..  (2008)  Cytotoxic constituents from Brazilian red propolis and their structure-activity relationship.,  16  (10): [PMID:18440233] [10.1016/j.bmc.2008.04.016]
    7. Mativandlela SP, Muthivhi T, Kikuchi H, Oshima Y, Hamilton C, Hussein AA, van der Walt ML, Houghton PJ, Lall N..  (2009)  Antimycobacterial flavonoids from the leaf extract of Galenia africana.,  72  (12): [PMID:20035557] [10.1021/np800778b]
    8. Awale S, Miyamoto T, Linn TZ, Li F, Win NN, Tezuka Y, Esumi H, Kadota S..  (2009)  Cytotoxic constituents of Soymida febrifuga from Myanmar.,  72  (9): [PMID:19689125] [10.1021/np9003323]
    9. PubChem BioAssay data set, 
    10. Bruyère C, Genovese S, Lallemand B, Ionescu-Motatu A, Curini M, Kiss R, Epifano F..  (2011)  Growth inhibitory activities of oxyprenylated and non-prenylated naturally occurring phenylpropanoids in cancer cell lines.,  21  (14): [PMID:21696954] [10.1016/j.bmcl.2011.05.089]
    11. Juvale K, Pape VF, Wiese M..  (2012)  Investigation of chalcones and benzochalcones as inhibitors of breast cancer resistance protein.,  20  (1): [PMID:22112540] [10.1016/j.bmc.2011.10.074]
    12. Hsieh CT, Hsieh TJ, El-Shazly M, Chuang DW, Tsai YH, Yen CT, Wu SF, Wu YC, Chang FR..  (2012)  Synthesis of chalcone derivatives as potential anti-diabetic agents.,  22  (12): [PMID:22608392] [10.1016/j.bmcl.2012.04.108]
    13. Wang SS, Zhang XJ, Que S, Tu GZ, Wan D, Cheng W, Liang H, Ye J, Zhang QY..  (2012)  3-Hydroxy-3-methylglutaryl flavonol glycosides from Oxytropis falcata.,  75  (7): [PMID:22775441] [10.1021/np300292f]
    14. Svetaz L, Tapia A, López SN, Furlán RL, Petenatti E, Pioli R, Schmeda-Hirschmann G, Zacchino SA..  (2004)  Antifungal chalcones and new caffeic acid esters from Zuccagnia punctata acting against soybean infecting fungi.,  52  (11): [PMID:15161186] [10.1021/jf035213x]
    15. Avram SI, Crisan L, Pacureanu LM, Bora A, Seclaman E, Balint M, Kurunczi LG.  (2013)  Challenges in docking 2-hydroxy and 2,4-dihydroxychalcones into the binding site of ALR2,  22  (8): [10.1007/s00044-012-0367-5]
    16. Sharma MC.  (2013)  Molecular modeling studies of substituted 3,4-dihydroxychalcone derivatives as 5-lipoxygenase and cyclooxygenase inhibitors,  [10.1007/s00044-013-0745-7]
    17. Kupcewicz B, Jarzęcki AA, Małecka M, Krajewska U, Rozalski M..  (2014)  Cytotoxic activity of substituted chalcones in terms of molecular electronic properties.,  24  (17): [PMID:25091929] [10.1016/j.bmcl.2014.07.027]
    18. Passalacqua TG, Torres FA, Nogueira CT, de Almeida L, Del Cistia ML, dos Santos MB, Regasini LO, Graminha MA, Marchetto R, Zottis A..  (2015)  The 2',4'-dihydroxychalcone could be explored to develop new inhibitors against the glycerol-3-phosphate dehydrogenase from Leishmania species.,  25  (17): [PMID:26169126] [10.1016/j.bmcl.2015.06.085]
    19. Li H, Jean S, Webster D, Robichaud GA, Calhoun LA, Johnson JA, Gray CA..  (2015)  Dibenz[b,f]oxepin and Antimycobacterial Chalcone Constituents of Empetrum nigrum.,  78  (11): [PMID:26473275] [10.1021/acs.jnatprod.5b00627]
    20. 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]
    21. Peng F, Meng CW, Zhou QM, Chen JP, Xiong L..  (2016)  Cytotoxic Evaluation against Breast Cancer Cells of Isoliquiritigenin Analogues from Spatholobus suberectus and Their Synthetic Derivatives.,  79  (1): [PMID:26690274] [10.1021/acs.jnatprod.5b00774]
    22. Nijampatnam B, Casals L, Zheng R, Wu H, Velu SE..  (2016)  Hydroxychalcone inhibitors of Streptococcus mutans glucosyl transferases and biofilms as potential anticaries agents.,  26  (15): [PMID:27371109] [10.1016/j.bmcl.2016.06.033]
    23. Xie Z, Luo X, Zou Z, Zhang X, Huang F, Li R, Liao S, Liu Y..  (2017)  Synthesis and evaluation of hydroxychalcones as multifunctional non-purine xanthine oxidase inhibitors for the treatment of hyperuricemia.,  27  (15): [PMID:28655421] [10.1016/j.bmcl.2017.01.053]
    24. Liu Y, Zhang X, Kelsang N, Tu G, Kong D, Lu J, Zhang Y, Liang H, Tu P, Zhang Q..  (2018)  Structurally Diverse Cytotoxic Dimeric Chalcones from Oxytropis chiliophylla.,  81  (2): [PMID:29400468] [10.1021/acs.jnatprod.7b00736]
    25. Marquina S, Maldonado-Santiago M, Sánchez-Carranza JN, Antúnez-Mojica M, González-Maya L, Razo-Hernández RS, Alvarez L..  (2019)  Design, synthesis and QSAR study of 2'-hydroxy-4'-alkoxy chalcone derivatives that exert cytotoxic activity by the mitochondrial apoptotic pathway.,  27  (1): [PMID:30482548] [10.1016/j.bmc.2018.10.045]
    26. Kumar A, Jaitak V..  (2019)  Natural products as multidrug resistance modulators in cancer.,  176  [PMID:31103904] [10.1016/j.ejmech.2019.05.027]
    27. Stevens M, Abdeen S, Salim N, Ray AM, Washburn A, Chitre S, Sivinski J, Park Y, Hoang QQ, Chapman E, Johnson SM..  (2019)  HSP60/10 chaperonin systems are inhibited by a variety of approved drugs, natural products, and known bioactive molecules.,  29  (9): [PMID:30852084] [10.1016/j.bmcl.2019.02.028]
    28. Hossain M, Das U, Dimmock JR..  (2019)  Recent advances in α,β-unsaturated carbonyl compounds as mitochondrial toxins.,  183  [PMID:31539776] [10.1016/j.ejmech.2019.111687]
    29. Selvaraj B, Kim DW, Huh G, Lee H, Kang K, Lee JW..  (2020)  Synthesis and biological evaluation of isoliquiritigenin derivatives as a neuroprotective agent against glutamate mediated neurotoxicity in HT22 cells.,  30  (8): [PMID:32122738] [10.1016/j.bmcl.2020.127058]
    30. Ellen Van Damme.  (2021)  Screening of ~5500 FDA-approved drugs and clinical candidates for anti-SARS-CoV-2 activity,  [10.6019/CHEMBL4651402]
    31. Zhang M,Zhang Y,Huang Q,Duan H,Zhao G,Liu L,Li Y.  (2021)  Flavonoids from Sophora alopecuroides L. improve palmitate-induced insulin resistance by inhibiting PTP1B activity in vitro.,  35  [PMID:33412152] [10.1016/j.bmcl.2021.127775]
    32. Dan W, Dai J..  (2020)  Recent developments of chalcones as potential antibacterial agents in medicinal chemistry.,  187  [PMID:31877539] [10.1016/j.ejmech.2019.111980]