Page last updated: 2024-11-12

dihydroxanthohumol

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

dihydroxanthohumol : A member of the class of dihydrochalcones that is the alpha,beta-dihydro derivative of xanthohumol. Isolated from Humulus lupulus, it exhibits inhibition of NO production. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

FloraRankFlora DefinitionFamilyFamily Definition
HumulusgenusA plant genus in the CANNABACEAE family. Best known for the buds of Humulus lupulus L. used in BEER.[MeSH]CannabaceaeA plant family of the order Urticales, subclass Hamamelidae, class Magnoliopsida. It is most notable for the members, Cannabis and Hops.[MeSH]
Humulus lupulusspecies[no description available]CannabaceaeA plant family of the order Urticales, subclass Hamamelidae, class Magnoliopsida. It is most notable for the members, Cannabis and Hops.[MeSH]

Cross-References

ID SourceID
PubMed CID10450920
CHEMBL ID510279
CHEBI ID66332
SCHEMBL ID15704299

Synonyms (25)

Synonym
MEGXP0_001797
ACON1_000059
smr000440746
MLS000863606 ,
NCGC00168833-01
alpha,beta-dihydroxanthohumol
4,2',4'-trihydroxy-6'-methoxy-3'-prenyldihydrochalcone
LMPK12120536
BRD-K15951006-001-01-4
1-[2,4-dihydroxy-6-methoxy-3-(3-methylbut-2-enyl)phenyl]-3-(4-hydroxyphenyl)propan-1-one
CHEMBL510279
dihydroxanthohumol
chebi:66332 ,
HMS2267A19
1-[2,4-dihydroxy-6-methoxy-3-(3-methylbut-2-en-1-yl)phenyl]-3-(4-hydroxyphenyl)propan-1-one
cid_10450920
1-[2,4-dihydroxy-6-methoxy-3-(3-methylbut-2-enyl)phenyl]-3-(4-hydroxyphenyl)-1-propanone
3-(4-hydroxyphenyl)-1-[6-methoxy-3-(3-methylbut-2-enyl)-2,4-bis(oxidanyl)phenyl]propan-1-one
bdbm76566
SCHEMBL15704299
a,b-dihydroxanthohumol
2',4,4'-trihydroxy-6'-methoxy-3'-prenyldihydrochalcone
Q27134880
102448-00-0
1-propanone, 1-[2,4-dihydroxy-6-methoxy-3-(3-methyl-2-buten-1-yl)phenyl]-3-(4-hydroxyphenyl)-
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (2)

RoleDescription
metaboliteAny intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
EC 1.14.13.39 (nitric oxide synthase) inhibitorAn EC 1.14.13.* (oxidoreductase acting on paired donors, incorporating 1 atom of oxygen, with NADH or NADPH as one donor) inhibitor that interferes with the action of nitric oxide synthase (EC 1.14.13.39).
[role information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Drug Classes (3)

ClassDescription
dihydrochalconesAny ketone that is 1,3-diphenylpropanone and its derivatives obtained by substitution.
polyphenolMembers of the class of phenols that contain 2 or more benzene rings each of which is substituted by at least one hydroxy group.
aromatic etherAny ether in which the oxygen is attached to at least one aryl substituent.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Protein Targets (20)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Chain A, Beta-lactamaseEscherichia coli K-12Potency44.66840.044717.8581100.0000AID485294
Chain A, JmjC domain-containing histone demethylation protein 3AHomo sapiens (human)Potency79.43280.631035.7641100.0000AID504339
glp-1 receptor, partialHomo sapiens (human)Potency2.51190.01846.806014.1254AID624417
TDP1 proteinHomo sapiens (human)Potency20.59620.000811.382244.6684AID686978; AID686979
Microtubule-associated protein tauHomo sapiens (human)Potency15.84890.180013.557439.8107AID1468
Smad3Homo sapiens (human)Potency22.38720.00527.809829.0929AID588855
nonstructural protein 1Influenza A virus (A/WSN/1933(H1N1))Potency4.46680.28189.721235.4813AID2326
67.9K proteinVaccinia virusPotency18.86770.00018.4406100.0000AID720579; AID720580
nuclear factor erythroid 2-related factor 2 isoform 2Homo sapiens (human)Potency25.92900.00419.984825.9290AID504444
parathyroid hormone/parathyroid hormone-related peptide receptor precursorHomo sapiens (human)Potency35.48133.548119.542744.6684AID743266
gemininHomo sapiens (human)Potency5.08790.004611.374133.4983AID624296; AID624297
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
calpain II, partialSus scrofa (pig)IC50 (µMol)5.00041.77424.93387.7087AID1420
SUMO-1-specific proteaseHomo sapiens (human)IC50 (µMol)10.00000.805019.346187.7000AID488921
SUMO1/sentrin specific peptidase 7Homo sapiens (human)IC50 (µMol)7.82001.64007.264823.9000AID488904
caspase-3 isoform a preproproteinHomo sapiens (human)IC50 (µMol)100.00000.025620.323574.3000AID488901
sentrin-specific protease 8Homo sapiens (human)IC50 (µMol)13.30000.040818.929294.8000AID488903
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Activation Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
delta-type opioid receptorHomo sapiens (human)EC50 (µMol)64.58400.13203.58649.5690AID602264
mu-type opioid receptor isoform MOR-1Homo sapiens (human)EC50 (µMol)64.58400.13203.30049.5690AID602264
streptokinase A precursorStreptococcus pyogenes M1 GASEC50 (µMol)2.75700.06008.9128130.5170AID1902
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (20)

Assay IDTitleYearJournalArticle
AID1745845Primary qHTS for Inhibitors of ATXN expression
AID651635Viability Counterscreen for Primary qHTS for Inhibitors of ATXN expression
AID588501High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set2010Current protocols in cytometry, Oct, Volume: Chapter 13Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588501High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set2006Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5
Microsphere-based protease assays and screening application for lethal factor and factor Xa.
AID588501High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set2010Assay and drug development technologies, Feb, Volume: 8, Issue:1
High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors.
AID588497High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set2010Current protocols in cytometry, Oct, Volume: Chapter 13Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588497High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set2006Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5
Microsphere-based protease assays and screening application for lethal factor and factor Xa.
AID588497High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set2010Assay and drug development technologies, Feb, Volume: 8, Issue:1
High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors.
AID504810Antagonists of the Thyroid Stimulating Hormone Receptor: HTS campaign2010Endocrinology, Jul, Volume: 151, Issue:7
A small molecule inverse agonist for the human thyroid-stimulating hormone receptor.
AID588499High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set2010Current protocols in cytometry, Oct, Volume: Chapter 13Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588499High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set2006Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5
Microsphere-based protease assays and screening application for lethal factor and factor Xa.
AID588499High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set2010Assay and drug development technologies, Feb, Volume: 8, Issue:1
High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors.
AID504812Inverse Agonists of the Thyroid Stimulating Hormone Receptor: HTS campaign2010Endocrinology, Jul, Volume: 151, Issue:7
A small molecule inverse agonist for the human thyroid-stimulating hormone receptor.
AID376753Cytotoxicity against mouse RAW264.7 cells assessed as cell viability at <10 uM after 16 hrs by MTT assay2005Journal of natural products, Jan, Volume: 68, Issue:1
Prenylflavonoids and phloroglucinol derivatives from hops (Humulus lupulus).
AID734220Antioxidant activity assessed as concentration required for 50 % inhibition of micoM DPPH activity after 30 mins by UV-vis spectrophotometry2013Bioorganic & medicinal chemistry, Apr-01, Volume: 21, Issue:7
Fungal metabolites of xanthohumol with potent antiproliferative activity on human cancer cell lines in vitro.
AID376752Inhibition of LPS/IFN-gamma-induced NO production in mouse RAW264.7 cells after 16 hrs2005Journal of natural products, Jan, Volume: 68, Issue:1
Prenylflavonoids and phloroglucinol derivatives from hops (Humulus lupulus).
AID734218Cytotoxicity against human PC3 cells after 72 hrs by SRB assay2013Bioorganic & medicinal chemistry, Apr-01, Volume: 21, Issue:7
Fungal metabolites of xanthohumol with potent antiproliferative activity on human cancer cell lines in vitro.
AID734216Cytotoxicity against human HT-29 cells after 72 hrs by SRB assay2013Bioorganic & medicinal chemistry, Apr-01, Volume: 21, Issue:7
Fungal metabolites of xanthohumol with potent antiproliferative activity on human cancer cell lines in vitro.
AID376754Cytotoxicity against mouse RAW264.7 cells assessed as cell viability at 20 uM after 16 hrs by MTT assay2005Journal of natural products, Jan, Volume: 68, Issue:1
Prenylflavonoids and phloroglucinol derivatives from hops (Humulus lupulus).
AID734217Cytotoxicity against human MCF7 cells after 72 hrs by SRB assay2013Bioorganic & medicinal chemistry, Apr-01, Volume: 21, Issue:7
Fungal metabolites of xanthohumol with potent antiproliferative activity on human cancer cell lines in vitro.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (7)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's2 (28.57)29.6817
2010's4 (57.14)24.3611
2020's1 (14.29)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 12.20

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be weak demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index12.20 (24.57)
Research Supply Index2.08 (2.92)
Research Growth Index4.28 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.20)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other7 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]