5-o-methyllicoricidin

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

Description

5-O-methyllicoricidin: structure given in first source; a new and potent benzodiazepine-binding stimulator from glycyrrhiza uralensis [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

licorisoflavan A : A member of the class of hydroxyisoflavans that is the 7-O-methyl derivative of licoricidin. Isolated from Glycyrrhiza uralensis, it exhibits antibacterial activity. [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]

Flora	Rank	Flora Definition	Family	Family Definition
Glycyrrhiza	genus	A genus of leguminous herbs or shrubs whose roots yield GLYCYRRHETINIC ACID and its derivative, CARBENOXOLONE.[MeSH]	Fabaceae	The large family of plants characterized by pods. Some are edible and some cause LATHYRISM or FAVISM and other forms of poisoning. Other species yield useful materials like gums from ACACIA and various LECTINS like PHYTOHEMAGGLUTININS from PHASEOLUS. Many of them harbor NITROGEN FIXATION bacteria on their roots. Many but not all species of beans belong to this family.[MeSH]
Glycyrrhiza uralensis	species	A plant species of the family FABACEAE.[MeSH]	Fabaceae	The large family of plants characterized by pods. Some are edible and some cause LATHYRISM or FAVISM and other forms of poisoning. Other species yield useful materials like gums from ACACIA and various LECTINS like PHYTOHEMAGGLUTININS from PHASEOLUS. Many of them harbor NITROGEN FIXATION bacteria on their roots. Many but not all species of beans belong to this family.[MeSH]
Glycyrrhiza uralensis	species	A plant species of the family FABACEAE.[MeSH]	Fabaceae	The large family of plants characterized by pods. Some are edible and some cause LATHYRISM or FAVISM and other forms of poisoning. Other species yield useful materials like gums from ACACIA and various LECTINS like PHYTOHEMAGGLUTININS from PHASEOLUS. Many of them harbor NITROGEN FIXATION bacteria on their roots. Many but not all species of beans belong to this family.[MeSH]

Cross-References

ID Source	ID
PubMed CID	196831
CHEMBL ID	4635007
CHEBI ID	69083
MeSH ID	M0206349

Synonyms (25)

Synonym
4-[(r)-5,7-dimethoxy-6-(3-methyl-but-2-enyl)-1-benzopyran-3-yl]-2-((e)-3-methyl-but-2-enyl)-benzene-1,3-diol
4-[(3r)-5,7-dimethoxy-6-(3-methylbut-2-enyl)chroman-3-yl]-2-(3-methylbut-2-enyl)benzene-1,3-diol
licoriisoflavan a
129314-37-0
licorisoflavan a
7-o-methyllicoricidin
4-[(3r)-5,7-dimethoxy-6-(3-methylbut-2-enyl)-3,4-dihydro-2h-chromen-3-yl]-2-(3-methylbut-2-enyl)benzene-1,3-diol
unii-jw8u2yd8jl
jw8u2yd8jl ,
5-o-methyllicoricidin
CHEBI:69083 ,
4-[(3r)-5,7-dimethoxy-6-(3-methylbut-2-en-1-yl)-3,4-dihydro-2h-chromen-3-yl]-2-(3-methylbut-2-en-1-yl)benzene-1,3-diol
DTXSID40156136
NCGC00385627-01
AKOS032949052
Q27137422
1,3-benzenediol, 4-((3r)-3,4-dihydro-5,7-dimethoxy-6-(3-methyl-2-buten-1-yl)-2h-1-benzopyran-3-yl)-2-(3-methyl-2-buten-1-yl)-
(+)-7-o-methyllicoricidin
4-((3r)-3,4-dihydro-5,7-dimethoxy-6-(3-methyl-2-buten-1-yl)-2h-1-benzopyran-3-yl)-2-(3-methyl-2-buten-1-yl)-1,3-benzenediol
7-o-methyllicorisoflavan b
CHEMBL4635007
HY-N3385
CS-0024064
licorisoflavana
4-((3r)-5,7-dimethoxy-6-(3-methylbut-2-en-1-yl)-3,4-dihydro-2h-chromen-3-yl)-2-(3-methylbut-2-en-1-yl)benzene-1,3-diol

Research Excerpts

Bioavailability

Excerpt	Reference	Relevance
"The ATP-binding cassette transporter P-glycoprotein (P-gp) is known to limit both brain penetration and oral bioavailability of many chemotherapy drugs."	( A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein. Ambudkar, SV; Brimacombe, KR; Chen, L; Gottesman, MM; Guha, R; Hall, MD; Klumpp-Thomas, C; Lee, OW; Lee, TD; Lusvarghi, S; Robey, RW; Shen, M; Tebase, BG, 2019)	0.51

[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (2)

Role	Description
antibacterial agent	A substance (or active part thereof) that kills or slows the growth of bacteria.
plant metabolite	Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
[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
aromatic ether	Any ether in which the oxygen is attached to at least one aryl substituent.
hydroxyisoflavans	A member of the class of isoflavans in which one or more ring hydrogens are replaced by hydroxy groups.
methoxyisoflavan	Any member of the class of isoflavans in which one or more ring hydrogens are replaced by methoxy groups.
[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]

Bioassays (8)

Assay ID	Title	Year	Journal	Article
AID1296008	Cytotoxic Profiling of Annotated Libraries Using Quantitative High-Throughput Screening	2020	SLAS discovery : advancing life sciences R & D, 01, Volume: 25, Issue:1	Cytotoxic Profiling of Annotated and Diverse Chemical Libraries Using Quantitative High-Throughput Screening.
AID1346987	P-glycoprotein substrates identified in KB-8-5-11 adenocarcinoma cell line, qHTS therapeutic library screen	2019	Molecular pharmacology, 11, Volume: 96, Issue:5	A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.
AID1346986	P-glycoprotein substrates identified in KB-3-1 adenocarcinoma cell line, qHTS therapeutic library screen	2019	Molecular pharmacology, 11, Volume: 96, Issue:5	A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.
AID1347159	Primary screen GU Rhodamine qHTS for Zika virus inhibitors: Unlinked NS2B-NS3 protease assay	2020	Proceedings of the National Academy of Sciences of the United States of America, 12-08, Volume: 117, Issue:49	Therapeutic candidates for the Zika virus identified by a high-throughput screen for Zika protease inhibitors.
AID1347160	Primary screen NINDS Rhodamine qHTS for Zika virus inhibitors	2020	Proceedings of the National Academy of Sciences of the United States of America, 12-08, Volume: 117, Issue:49	Therapeutic candidates for the Zika virus identified by a high-throughput screen for Zika protease inhibitors.
AID1651899	Cytotoxicity against human insulin resistant HepG2 cells assessed as cell viability at 10 uM by CCK8 assay relative to control
AID1651898	Inhibition of alpha-Glucosidase (unknown origin) at 10 uM using pNPG as substrate incubated for 30 mins relative to control
AID1651897	Inhibition of recombinant human PTP1B (1 to 321 residues) expressed in Escherichia coli at 10 uM using p-nitrophenyl phosphate as substrate incubated for 30 mins relative to control
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (10)

Timeframe	Studies, This Drug (%)	All Drugs %
pre-1990	0 (0.00)	18.7374
1990's	1 (10.00)	18.2507
2000's	0 (0.00)	29.6817
2010's	6 (60.00)	24.3611
2020's	3 (30.00)	2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 11.92

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.

Metric	This Compound (vs All)
Research Demand Index	11.92 (24.57)
Research Supply Index	2.40 (2.92)
Research Growth Index	4.32 (4.65)
Search Engine Demand Index	0.00 (26.88)
Search Engine Supply Index	0.00 (0.95)

This Compound (11.92)

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	10 (100.00%)	84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Substance	Relationship Strength	Studies	Classes	Roles
thiazoles [no description available]	2.11	1	1,3-thiazoles; mancude organic heteromonocyclic parent; monocyclic heteroarene
gentian violet Gentian Violet: A dye that is a mixture of violet rosanilinis with antibacterial, antifungal, and anthelmintic properties.. crystal violet : An organic chloride salt that is the monochloride salt of crystal violet cation. It has been used in creams for the topical treatment of bacterial and fungal infections, being effective against some Gram-positive bacteria (notably Staphylococcus species) and some pathogenic fungi (including Candida species) but use declined following reports of animal carcinogenicity. It has also been used for dying wood, silk, and paper, as well as a histological stain.	2.11	1	organic chloride salt	anthelminthic drug; antibacterial agent; antifungal agent; antiseptic drug; histological dye
thiazolyl blue thiazolyl blue: RN & II refers to bromide. 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide : The bromide salt of 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium.	2.11	1	organic bromide salt	colorimetric reagent; dye
benzofurans Benzofurans: Compounds that contain a BENZENE ring fused to a furan ring.	2.11	1
6,8-diprenylgenistein 6,8-diprenylgenistein: a lysoPAF acetyltransferase inhibitor isolated from licorice root; structure in first source. 5,7,4'-trihydroxy-6,8-diprenylisoflavone : A member of the class of 7-hydroxyisoflavones that is genistein substituted by prenyl groups at positions 6 and 8. It has been isolated from Derris scandens and Glycyrrhiza uralensis.	2.11	1	7-hydroxyisoflavones	antibacterial agent; plant metabolite
licoricidin licoricidin: a lysoPAF acetyltransferase inhibitor isolated from licorice root; structure in first source. licoricidin : A member of the class of hydroxyisoflavans that is R-isoflavan with hydroxy groups at positions 7, 2' and 4', a methoxy group at position 5 and prenyl groups at positions 6 and 3'. Isolated from Glycyrrhiza uralensis, it exhibits antibacterial activity.	2.76	3	aromatic ether; hydroxyisoflavans; methoxyisoflavan	antibacterial agent; plant metabolite
genistein [no description available]	2.11	1	7-hydroxyisoflavones	antineoplastic agent; EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor; geroprotector; human urinary metabolite; phytoestrogen; plant metabolite; tyrosine kinase inhibitor
sulfur Sulfur: An element that is a member of the chalcogen family. It has an atomic symbol S, atomic number 16, and atomic weight [32.059; 32.076]. It is found in the amino acids cysteine and methionine.	2.07	1	chalcogen; nonmetal atom	macronutrient
chlorhexidine Chlorhexidine: A disinfectant and topical anti-infective agent used also as mouthwash to prevent oral plaque.. chlorhexidine : A bisbiguanide compound with a structure consisting of two (p-chlorophenyl)guanide units linked by a hexamethylene bridge.	2.11	1	biguanides; monochlorobenzenes	antibacterial agent; antiinfective agent
interleukin-8 Interleukin-8: A member of the CXC chemokine family that plays a role in the regulation of the acute inflammatory response. It is secreted by variety of cell types and induces CHEMOTAXIS of NEUTROPHILS and other inflammatory cells.	2.06	1
warfarin Warfarin: An anticoagulant that acts by inhibiting the synthesis of vitamin K-dependent coagulation factors. Warfarin is indicated for the prophylaxis and/or treatment of venous thrombosis and its extension, pulmonary embolism, and atrial fibrillation with embolization. It is also used as an adjunct in the prophylaxis of systemic embolism after myocardial infarction. Warfarin is also used as a rodenticide.. warfarin : A racemate comprising equal amounts of (R)- and (S)-warfarin. Extensively used as both an anticoagulant drug and as a pesticide against rats and mice.. 4-hydroxy-3-(3-oxo-1-phenylbutyl)-1-benzopyran-2-one : A member of the class of coumarins that is 4-hydroxycoumarin which is substituted at position 3 by a 1-phenyl-3-oxo-1-butyl group.	2.06	1	benzenes; hydroxycoumarin; methyl ketone

Condition	Relationship Strength	Studies
Congenital Zika Syndrome [description not available]	2.25	1
Disease Models, Animal Naturally-occurring or experimentally-induced animal diseases with pathological processes analogous to human diseases.	2.25	1
Zika Virus Infection A viral disease transmitted by the bite of AEDES mosquitoes infected with ZIKA VIRUS. Its mild DENGUE-like symptoms include fever, rash, headaches and ARTHRALGIA. The viral infection during pregnancy, in rare cases, is associated with congenital brain and ocular abnormalities, called Congenital Zika Syndrome, including MICROCEPHALY and may also lead to GUILLAIN-BARRE SYNDROME.	2.25	1
Depression Depressive states usually of moderate intensity in contrast with MAJOR DEPRESSIVE DISORDER present in neurotic and psychotic disorders.	2.21	1
Halitosis An offensive, foul breath odor resulting from a variety of causes such as poor oral hygiene, dental or oral infections, or the ingestion of certain foods.	2.07	1

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