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]
Related Flora
| Flora | Rank | Flora Definition | Family | Family Definition |
|---|---|---|---|---|
| Humulus | genus | A plant genus in the CANNABACEAE family. Best known for the buds of Humulus lupulus L. used in BEER.[MeSH] | Cannabaceae | A plant family of the order Urticales, subclass Hamamelidae, class Magnoliopsida. It is most notable for the members, Cannabis and Hops.[MeSH] |
| Humulus lupulus | species | [no description available] | Cannabaceae | A plant family of the order Urticales, subclass Hamamelidae, class Magnoliopsida. It is most notable for the members, Cannabis and Hops.[MeSH] |
Cross-References
| ID Source | ID |
|---|---|
| PubMed CID | 10450920 |
| CHEMBL ID | 510279 |
| CHEBI ID | 66332 |
| SCHEMBL ID | 15704299 |
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)
| Role | Description |
|---|---|
| metabolite | Any 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) inhibitor | An 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)
| Class | Description |
|---|---|
| dihydrochalcones | Any ketone that is 1,3-diphenylpropanone and its derivatives obtained by substitution. |
| polyphenol | Members of the class of phenols that contain 2 or more benzene rings each of which is substituted by at least one hydroxy group. |
| aromatic ether | Any 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
| Protein | Taxonomy | Measurement | Average (µ) | Min (ref.) | Avg (ref.) | Max (ref.) | Bioassay(s) |
|---|---|---|---|---|---|---|---|
| Chain A, Beta-lactamase | Escherichia coli K-12 | Potency | 44.6684 | 0.0447 | 17.8581 | 100.0000 | AID485294 |
| Chain A, JmjC domain-containing histone demethylation protein 3A | Homo sapiens (human) | Potency | 79.4328 | 0.6310 | 35.7641 | 100.0000 | AID504339 |
| glp-1 receptor, partial | Homo sapiens (human) | Potency | 2.5119 | 0.0184 | 6.8060 | 14.1254 | AID624417 |
| TDP1 protein | Homo sapiens (human) | Potency | 20.5962 | 0.0008 | 11.3822 | 44.6684 | AID686978; AID686979 |
| Microtubule-associated protein tau | Homo sapiens (human) | Potency | 15.8489 | 0.1800 | 13.5574 | 39.8107 | AID1468 |
| Smad3 | Homo sapiens (human) | Potency | 22.3872 | 0.0052 | 7.8098 | 29.0929 | AID588855 |
| nonstructural protein 1 | Influenza A virus (A/WSN/1933(H1N1)) | Potency | 4.4668 | 0.2818 | 9.7212 | 35.4813 | AID2326 |
| 67.9K protein | Vaccinia virus | Potency | 18.8677 | 0.0001 | 8.4406 | 100.0000 | AID720579; AID720580 |
| nuclear factor erythroid 2-related factor 2 isoform 2 | Homo sapiens (human) | Potency | 25.9290 | 0.0041 | 9.9848 | 25.9290 | AID504444 |
| parathyroid hormone/parathyroid hormone-related peptide receptor precursor | Homo sapiens (human) | Potency | 35.4813 | 3.5481 | 19.5427 | 44.6684 | AID743266 |
| geminin | Homo sapiens (human) | Potency | 5.0879 | 0.0046 | 11.3741 | 33.4983 | AID624296; AID624297 |
| [prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023] | |||||||
Inhibition Measurements
| Protein | Taxonomy | Measurement | Average | Min (ref.) | Avg (ref.) | Max (ref.) | Bioassay(s) |
|---|---|---|---|---|---|---|---|
| calpain II, partial | Sus scrofa (pig) | IC50 (µMol) | 5.0004 | 1.7742 | 4.9338 | 7.7087 | AID1420 |
| SUMO-1-specific protease | Homo sapiens (human) | IC50 (µMol) | 10.0000 | 0.8050 | 19.3461 | 87.7000 | AID488921 |
| SUMO1/sentrin specific peptidase 7 | Homo sapiens (human) | IC50 (µMol) | 7.8200 | 1.6400 | 7.2648 | 23.9000 | AID488904 |
| caspase-3 isoform a preproprotein | Homo sapiens (human) | IC50 (µMol) | 100.0000 | 0.0256 | 20.3235 | 74.3000 | AID488901 |
| sentrin-specific protease 8 | Homo sapiens (human) | IC50 (µMol) | 13.3000 | 0.0408 | 18.9292 | 94.8000 | AID488903 |
| [prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023] | |||||||
Activation Measurements
| Protein | Taxonomy | Measurement | Average | Min (ref.) | Avg (ref.) | Max (ref.) | Bioassay(s) |
|---|---|---|---|---|---|---|---|
| delta-type opioid receptor | Homo sapiens (human) | EC50 (µMol) | 64.5840 | 0.1320 | 3.5864 | 9.5690 | AID602264 |
| mu-type opioid receptor isoform MOR-1 | Homo sapiens (human) | EC50 (µMol) | 64.5840 | 0.1320 | 3.3004 | 9.5690 | AID602264 |
| streptokinase A precursor | Streptococcus pyogenes M1 GAS | EC50 (µMol) | 2.7570 | 0.0600 | 8.9128 | 130.5170 | AID1902 |
| [prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023] | |||||||
Bioassays (20)
| Assay ID | Title | Year | Journal | Article |
|---|---|---|---|---|
| AID1745845 | Primary qHTS for Inhibitors of ATXN expression | |||
| AID651635 | Viability Counterscreen for Primary qHTS for Inhibitors of ATXN expression | |||
| AID588501 | High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set | 2010 | Current protocols in cytometry, Oct, Volume: Chapter 13 | Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening. |
| AID588501 | High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set | 2006 | Cytometry. 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. |
| AID588501 | High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set | 2010 | Assay and drug development technologies, Feb, Volume: 8, Issue:1 | High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors. |
| AID588497 | High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set | 2010 | Current protocols in cytometry, Oct, Volume: Chapter 13 | Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening. |
| AID588497 | High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set | 2006 | Cytometry. 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. |
| AID588497 | High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set | 2010 | Assay and drug development technologies, Feb, Volume: 8, Issue:1 | High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors. |
| AID504810 | Antagonists of the Thyroid Stimulating Hormone Receptor: HTS campaign | 2010 | Endocrinology, Jul, Volume: 151, Issue:7 | A small molecule inverse agonist for the human thyroid-stimulating hormone receptor. |
| AID588499 | High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set | 2010 | Current protocols in cytometry, Oct, Volume: Chapter 13 | Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening. |
| AID588499 | High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set | 2006 | Cytometry. 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. |
| AID588499 | High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set | 2010 | Assay and drug development technologies, Feb, Volume: 8, Issue:1 | High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors. |
| AID504812 | Inverse Agonists of the Thyroid Stimulating Hormone Receptor: HTS campaign | 2010 | Endocrinology, Jul, Volume: 151, Issue:7 | A small molecule inverse agonist for the human thyroid-stimulating hormone receptor. |
| AID376753 | Cytotoxicity against mouse RAW264.7 cells assessed as cell viability at <10 uM after 16 hrs by MTT assay | 2005 | Journal of natural products, Jan, Volume: 68, Issue:1 | Prenylflavonoids and phloroglucinol derivatives from hops (Humulus lupulus). |
| AID734220 | Antioxidant activity assessed as concentration required for 50 % inhibition of micoM DPPH activity after 30 mins by UV-vis spectrophotometry | 2013 | Bioorganic & medicinal chemistry, Apr-01, Volume: 21, Issue:7 | Fungal metabolites of xanthohumol with potent antiproliferative activity on human cancer cell lines in vitro. |
| AID376752 | Inhibition of LPS/IFN-gamma-induced NO production in mouse RAW264.7 cells after 16 hrs | 2005 | Journal of natural products, Jan, Volume: 68, Issue:1 | Prenylflavonoids and phloroglucinol derivatives from hops (Humulus lupulus). |
| AID734218 | Cytotoxicity against human PC3 cells after 72 hrs by SRB assay | 2013 | Bioorganic & medicinal chemistry, Apr-01, Volume: 21, Issue:7 | Fungal metabolites of xanthohumol with potent antiproliferative activity on human cancer cell lines in vitro. |
| AID734216 | Cytotoxicity against human HT-29 cells after 72 hrs by SRB assay | 2013 | Bioorganic & medicinal chemistry, Apr-01, Volume: 21, Issue:7 | Fungal metabolites of xanthohumol with potent antiproliferative activity on human cancer cell lines in vitro. |
| AID376754 | Cytotoxicity against mouse RAW264.7 cells assessed as cell viability at 20 uM after 16 hrs by MTT assay | 2005 | Journal of natural products, Jan, Volume: 68, Issue:1 | Prenylflavonoids and phloroglucinol derivatives from hops (Humulus lupulus). |
| AID734217 | Cytotoxicity against human MCF7 cells after 72 hrs by SRB assay | 2013 | Bioorganic & 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)
| Timeframe | Studies, This Drug (%) | All Drugs % |
|---|---|---|
| pre-1990 | 0 (0.00) | 18.7374 |
| 1990's | 0 (0.00) | 18.2507 |
| 2000's | 2 (28.57) | 29.6817 |
| 2010's | 4 (57.14) | 24.3611 |
| 2020's | 1 (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.
| This Compound (12.20) All Compounds (24.57) |
Study Types
| Publication Type | This drug (%) | All Drugs (%) |
|---|---|---|
| Trials | 0 (0.00%) | 5.53% |
| Reviews | 0 (0.00%) | 6.00% |
| Case Studies | 0 (0.00%) | 4.05% |
| Observational | 0 (0.00%) | 0.25% |
| Other | 7 (100.00%) | 84.16% |
| [information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||