Compounds > genistein-8-c-glucoside
Page last updated: 2024-11-10

genistein-8-c-glucoside

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

Description

genistein 8-C-glucoside : A C-glycosyl compound that is genistein substituted by a beta-D-glucopyranosyl residue at position 8 via a C-glucosidic linkage. [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
LupinusgenusA plant genus of the family FABACEAE that is a source of SPARTEINE, lupanine and other lupin alkaloids.[MeSH]FabaceaeThe 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]
Lupinus luteusspecies[no description available]FabaceaeThe 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 SourceID
PubMed CID5281757
CHEMBL ID1945734
CHEBI ID5304
SCHEMBL ID15241300
MeSH IDM0372452

Synonyms (15)

Synonym
C10420 ,
genistein 8-c-glucoside
66026-80-0
5,7-dihydroxy-3-(4-hydroxyphenyl)-8-[(2s,3r,4r,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]chromen-4-one
chebi:5304 ,
CHEMBL1945734 ,
(1s)-1,5-anhydro-1-[5,7-dihydroxy-3-(4-hydroxyphenyl)-4-oxo-4h-1-benzopyran-8-yl]-d-glucitol
SCHEMBL15241300
DTXSID10415186
HY-N6882
Q27106711
g8cg
CS-0100476
MS-27705
AKOS040740791

Research Excerpts

Compound-Compound Interactions

ExcerptReferenceRelevance
"The crude methanol extract of Pueraria lobata was investigated by dual high-resolution α-glucosidase inhibition and radical scavenging profiling combined with hyphenated HPLC-HRMS-SPE-NMR."( Dual high-resolution α-glucosidase and radical scavenging profiling combined with HPLC-HRMS-SPE-NMR for identification of minor and major constituents directly from the crude extract of Pueraria lobata.
Jäger, AK; Kongstad, KT; Liu, B; Nyberg, NT; Qinglei, S; Staerk, D, 2015)		0.42
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (1)

RoleDescription
plant metaboliteAny 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 (2)

ClassDescription
C-glycosyl compoundA glycosyl compound arising formally from the elimination of water from a glycosidic hydroxy group and an H atom bound to a carbon atom, thus creating a C-C bond.
7-hydroxyisoflavonesA hydroxyisoflavone compound having a hydroxy group at the 7-position.
[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 (23)

Assay IDTitleYearJournalArticle
AID1169952Antidiabetic activity in STZ-induced diabetic Wistar rat model assessed as normalization of fasting hyperglycemia at 4 mg/kg/day, ip for 7 days by intragastric glucose tolerance test2014Journal of medicinal chemistry, Nov-26, Volume: 57, Issue:22
Exploiting the therapeutic potential of 8-β-d-glucopyranosylgenistein: synthesis, antidiabetic activity, and molecular interaction with islet amyloid polypeptide and amyloid β-peptide (1-42).
AID1676909Octanol/water partition coefficient, log D of compound at pH 7.4 at 1 uM incubated for 2 hrs by LC-MS analysis2020Journal of medicinal chemistry, 10-22, Volume: 63, Issue:20
Glucosylpolyphenols as Inhibitors of Aβ-Induced Fyn Kinase Activation and Tau Phosphorylation: Synthesis, Membrane Permeability, and Exploratory Target Assessment within the Scope of Type 2 Diabetes and Alzheimer's Disease.
AID1676892Inhibition of natural amyloid beta (1 to 42) monomers (unknown origin) stably expressed in CHO cells co-expressing APP751 with Val717Phe mutation/prion protein interaction in HEK293 cells assessed as residual amyloid beta-cellular prion protein level at 12020Journal of medicinal chemistry, 10-22, Volume: 63, Issue:20
Glucosylpolyphenols as Inhibitors of Aβ-Induced Fyn Kinase Activation and Tau Phosphorylation: Synthesis, Membrane Permeability, and Exploratory Target Assessment within the Scope of Type 2 Diabetes and Alzheimer's Disease.
AID1169957Inhibition of human IAPP fibril formation at 50 uM at 25 degC measured after 6 hrs by ThT fluorescence assay2014Journal of medicinal chemistry, Nov-26, Volume: 57, Issue:22
Exploiting the therapeutic potential of 8-β-d-glucopyranosylgenistein: synthesis, antidiabetic activity, and molecular interaction with islet amyloid polypeptide and amyloid β-peptide (1-42).
AID1169956Inhibition of human IAPP fibril formation at 50 uM at 25 degC measured after 6 hrs by atomic force microscopy2014Journal of medicinal chemistry, Nov-26, Volume: 57, Issue:22
Exploiting the therapeutic potential of 8-β-d-glucopyranosylgenistein: synthesis, antidiabetic activity, and molecular interaction with islet amyloid polypeptide and amyloid β-peptide (1-42).
AID1169955Antidiabetic activity in STZ-induced diabetic Wistar rat model assessed as increase in beta-cell sensitivity at 4 mg/kg/day, ip for 7 days2014Journal of medicinal chemistry, Nov-26, Volume: 57, Issue:22
Exploiting the therapeutic potential of 8-β-d-glucopyranosylgenistein: synthesis, antidiabetic activity, and molecular interaction with islet amyloid polypeptide and amyloid β-peptide (1-42).
AID1169961Cytotoxicity against mouse HII4E cells after 24 hrs by MTT cell viability assay2014Journal of medicinal chemistry, Nov-26, Volume: 57, Issue:22
Exploiting the therapeutic potential of 8-β-d-glucopyranosylgenistein: synthesis, antidiabetic activity, and molecular interaction with islet amyloid polypeptide and amyloid β-peptide (1-42).
AID1676908Effective permeability of compound at pH 7.4 by incubated for 16 hrs by PAMPA2020Journal of medicinal chemistry, 10-22, Volume: 63, Issue:20
Glucosylpolyphenols as Inhibitors of Aβ-Induced Fyn Kinase Activation and Tau Phosphorylation: Synthesis, Membrane Permeability, and Exploratory Target Assessment within the Scope of Type 2 Diabetes and Alzheimer's Disease.
AID1169960Binding affinity to amyloid beta (1 to 42) (unknown origin) at 2 mM by 2D-NOESY spectroscopy2014Journal of medicinal chemistry, Nov-26, Volume: 57, Issue:22
Exploiting the therapeutic potential of 8-β-d-glucopyranosylgenistein: synthesis, antidiabetic activity, and molecular interaction with islet amyloid polypeptide and amyloid β-peptide (1-42).
AID1676894Inhibition of basal Fyn activation in hiPSC neural progenitor cells assessed as reduction in pFyn levels in absence of amyloid beta at 10 uM by DAPI staining based immunofluorescence assay2020Journal of medicinal chemistry, 10-22, Volume: 63, Issue:20
Glucosylpolyphenols as Inhibitors of Aβ-Induced Fyn Kinase Activation and Tau Phosphorylation: Synthesis, Membrane Permeability, and Exploratory Target Assessment within the Scope of Type 2 Diabetes and Alzheimer's Disease.
AID1169953Antidiabetic activity in STZ-induced diabetic Wistar rat model assessed as reduction in excessive postprandial glucose excursion at 4 mg/kg/day, ip for 7 days by intragastric glucose tolerance test2014Journal of medicinal chemistry, Nov-26, Volume: 57, Issue:22
Exploiting the therapeutic potential of 8-β-d-glucopyranosylgenistein: synthesis, antidiabetic activity, and molecular interaction with islet amyloid polypeptide and amyloid β-peptide (1-42).
AID1676904Inhibition of equine serum BuChE at 100 uM using butyrylthiocholine iodide as substrate by Ellman's colorimetric analysis relative to control2020Journal of medicinal chemistry, 10-22, Volume: 63, Issue:20
Glucosylpolyphenols as Inhibitors of Aβ-Induced Fyn Kinase Activation and Tau Phosphorylation: Synthesis, Membrane Permeability, and Exploratory Target Assessment within the Scope of Type 2 Diabetes and Alzheimer's Disease.
AID1676902Inhibition of almond beta-glucosidase at 100 uM using p-nitrophenyl glycosides as substrate measured for 125 secs by spectrophotometry analysis relative to control2020Journal of medicinal chemistry, 10-22, Volume: 63, Issue:20
Glucosylpolyphenols as Inhibitors of Aβ-Induced Fyn Kinase Activation and Tau Phosphorylation: Synthesis, Membrane Permeability, and Exploratory Target Assessment within the Scope of Type 2 Diabetes and Alzheimer's Disease.
AID1169962Ratio of compound IC50 to chloramphenicol IC50 for mouse HII4E cells after 24 hrs by MTT cell viability assay2014Journal of medicinal chemistry, Nov-26, Volume: 57, Issue:22
Exploiting the therapeutic potential of 8-β-d-glucopyranosylgenistein: synthesis, antidiabetic activity, and molecular interaction with islet amyloid polypeptide and amyloid β-peptide (1-42).
AID1204997Antioxidant activity of the compound assessed as inhibition of ABTS radicals after 20 mins by spectrophotometric analysis2015Journal of natural products, Feb-27, Volume: 78, Issue:2
Dual high-resolution α-glucosidase and radical scavenging profiling combined with HPLC-HRMS-SPE-NMR for identification of minor and major constituents directly from the crude extract of Pueraria lobata.
AID1676901Inhibition of Saccharomyces cerevisiae alpha-glucosidase at 100 uM using p-nitrophenyl glycosides as substrate measured for 125 secs by spectrophotometry analysis relative to control2020Journal of medicinal chemistry, 10-22, Volume: 63, Issue:20
Glucosylpolyphenols as Inhibitors of Aβ-Induced Fyn Kinase Activation and Tau Phosphorylation: Synthesis, Membrane Permeability, and Exploratory Target Assessment within the Scope of Type 2 Diabetes and Alzheimer's Disease.
AID1169959Binding affinity to amyloid beta (1 to 42) (unknown origin) at 2 mM by saturation transfer difference NMR analysis2014Journal of medicinal chemistry, Nov-26, Volume: 57, Issue:22
Exploiting the therapeutic potential of 8-β-d-glucopyranosylgenistein: synthesis, antidiabetic activity, and molecular interaction with islet amyloid polypeptide and amyloid β-peptide (1-42).
AID493896Glucose uptake enhancing activity in insulin-stimulated mouse 3T3L1 cells at 10 uM after 4 days by FLIPR based 2-DG uptake assay relative to control2010Bioorganic & medicinal chemistry letters, Aug-01, Volume: 20, Issue:15
Glucose uptake enhancing activity of puerarin and the role of C-glucoside suggested from activity of related compounds.
AID1169958Binding affinity to human IAPP fibril at 2 mM by saturation transfer difference NMR analysis2014Journal of medicinal chemistry, Nov-26, Volume: 57, Issue:22
Exploiting the therapeutic potential of 8-β-d-glucopyranosylgenistein: synthesis, antidiabetic activity, and molecular interaction with islet amyloid polypeptide and amyloid β-peptide (1-42).
AID1676899Cytotoxicity against hiPSC neural cells assessed as reduction in cell viability at 10 uM incubated for 24 hrs by MTT assay2020Journal of medicinal chemistry, 10-22, Volume: 63, Issue:20
Glucosylpolyphenols as Inhibitors of Aβ-Induced Fyn Kinase Activation and Tau Phosphorylation: Synthesis, Membrane Permeability, and Exploratory Target Assessment within the Scope of Type 2 Diabetes and Alzheimer's Disease.
AID643972Osteogenic activity in rat primary calvarial osteoblasts assessed as induction of ALP activity at 1 pM to 1 uM after 10 days by colorimetry2012Bioorganic & medicinal chemistry letters, Jan-15, Volume: 22, Issue:2
Constituents of Dalbergia sissoo Roxb. leaves with osteogenic activity.
AID1169954Antidiabetic activity in STZ-induced diabetic Wistar rat model assessed as increase in circulating insulin at 4 mg/kg/day, ip for 7 days by intragastric tolerance test2014Journal of medicinal chemistry, Nov-26, Volume: 57, Issue:22
Exploiting the therapeutic potential of 8-β-d-glucopyranosylgenistein: synthesis, antidiabetic activity, and molecular interaction with islet amyloid polypeptide and amyloid β-peptide (1-42).
AID1676903Inhibition of electric eel AChE at 100 uM using acetylthiocholine iodide as substrate by Ellman's colorimetric analysis relative to control2020Journal of medicinal chemistry, 10-22, Volume: 63, Issue:20
Glucosylpolyphenols as Inhibitors of Aβ-Induced Fyn Kinase Activation and Tau Phosphorylation: Synthesis, Membrane Permeability, and Exploratory Target Assessment within the Scope of Type 2 Diabetes and Alzheimer's Disease.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (5)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's0 (0.00)29.6817
2010's4 (80.00)24.3611
2020's1 (20.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 13.28

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 Index13.28 (24.57)
Research Supply Index1.79 (2.92)
Research Growth Index5.08 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (13.28)

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%
Other5 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
chloramphenicol
Amphenicol: Chloramphenicol and its derivatives.		2.110C-nitro compound;
carboxamide;
diol;
organochlorine compound		antibacterial drug;
antimicrobial agent;
Escherichia coli metabolite;
geroprotector;
Mycoplasma genitalium metabolite;
protein synthesis inhibitor
daidzin
daidzin: a potent, selective, and reversible inhibitor of human mitochondrial aldehyde dehydrogenase. daidzein 7-O-beta-D-glucoside : A glycosyloxyisoflavone that is daidzein attached to a beta-D-glucopyranosyl residue at position 7 via a glycosidic linkage. It is used in the treatment of alcohol dependency (antidipsotropic).		2.48207-hydroxyisoflavones 7-O-beta-D-glucoside;
hydroxyisoflavone;
monosaccharide derivative		plant metabolite
ononin
[no description available]		2.11104'-methoxyisoflavones;
7-hydroxyisoflavones 7-O-beta-D-glucoside;
monosaccharide derivative		plant metabolite
acanthoside b
acanthoside B: isolated from the herb Huanghuaren; RN given refers to (1S-(1alpha,3aalpha,4alpha,6aalpha))-isomer		2.0710beta-D-glucosidemetabolite
ketoconazole
(2R,4S)-ketoconazole : A cis-1-acetyl-4-(4-{[2-(2,4-dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy}phenyl)piperazine which dioxolane moiety has (2R,4S)-configuration.		2.2510cis-1-acetyl-4-(4-{[2-(2,4-dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy}phenyl)piperazine
biochanin a
[no description available]		2.07104'-methoxyisoflavones;
7-hydroxyisoflavones		antineoplastic agent;
EC 3.5.1.99 (fatty acid amide hydrolase) inhibitor;
phytoestrogen;
plant metabolite;
tyrosine kinase inhibitor
formononetin
[no description available]		2.11104'-methoxyisoflavones;
7-hydroxyisoflavones		phytoestrogen;
plant metabolite
vitexin
[no description available]		2.0510C-glycosyl compound;
trihydroxyflavone		antineoplastic agent;
EC 3.2.1.20 (alpha-glucosidase) inhibitor;
plant metabolite;
platelet aggregation inhibitor
quercetin 3-o-glucopyranoside
quercetin 3-O-glucopyranoside: structure in first source. quercetin 3-O-beta-D-glucopyranoside : A quercetin O-glucoside that is quercetin with a beta-D-glucosyl residue attached at position 3. Isolated from Lepisorus contortus, it exhibits antineoplastic activityand has been found to decrease the rate of polymerization and sickling of red blood cells		2.0710beta-D-glucoside;
monosaccharide derivative;
quercetin O-glucoside;
tetrahydroxyflavone		antineoplastic agent;
antioxidant;
antipruritic drug;
bone density conservation agent;
geroprotector;
histamine antagonist;
osteogenesis regulator;
plant metabolite
rutin
Hydroxyethylrutoside: Monohydroxyethyl derivative of rutin. Peripheral circulation stimulant used in treatment of venous disorders.		2.0710disaccharide derivative;
quercetin O-glucoside;
rutinoside;
tetrahydroxyflavone		antioxidant;
metabolite
genistein
[no description available]		2.81307-hydroxyisoflavonesantineoplastic agent;
EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor;
geroprotector;
human urinary metabolite;
phytoestrogen;
plant metabolite;
tyrosine kinase inhibitor
genistin
genistin: glycoside of soy bean isoflavone, gentistein		2.49207-hydroxyisoflavones 7-O-beta-D-glucoside
daidzein
[no description available]		2.48207-hydroxyisoflavonesantineoplastic agent;
EC 2.7.7.7 (DNA-directed DNA polymerase) inhibitor;
EC 3.2.1.20 (alpha-glucosidase) inhibitor;
phytoestrogen;
plant metabolite
4'-methoxy-3',5,7-trihydroxyisoflavone
4'-methoxy-3',5,7-trihydroxyisoflavone: structure in first source. pratensein : A member of the class of 7-hydroxyisoflavones in which isoflavone is substituted by hydroxy groups at the 5, 7, and 3' positions, and by a methoxy group at the 4' position.		2.07104'-methoxyisoflavones;
7-hydroxyisoflavones
puerarin
[no description available]		2.4820C-glycosyl compound;
hydroxyisoflavone		plant metabolite
astragalin
kaempferol-3-O-glucoside: isolated from the pit of Mahkota dewa; structure in first source. kaempferol 3-O-beta-D-glucoside : A kaempferol O-glucoside in which a glucosyl residue is attached at position 3 of kaempferol via a beta-glycosidic linkage.		2.0710beta-D-glucoside;
kaempferol O-glucoside;
monosaccharide derivative;
trihydroxyflavone		plant metabolite;
trypanocidal drug
kaempferol-3-o-rutinoside
kaempferol-3-O-rutinoside: isolated from the methanolic extract of the whole plants of Diodia teres through repeated silica gel and Sephadex LH-20 column chromatography; structure in first source. kaempferol-3-rutinoside : A kaempferol O-glucoside that is kaempferol attached to a rutinosyl [6-deoxy-alpha-L-mannosyl-(1->6)-beta-D-glucosyl] residue at position 3 via a glycosidic linkage. It has been isolated from the leaves of Solanum campaniforme.		2.0710disaccharide derivative;
kaempferol O-glucoside;
rutinoside;
trihydroxyflavone		metabolite;
plant metabolite;
radical scavenger
caviunin
caviunin: from the stems of Dalbergia vietnamensis; structure in first source		2.0710
6''-o-malonyldaidzin
6''-O-malonyldaidzin: structure in first source. malonyldaidzin : A glycosyloxyisoflavone that is daidzein substituted by a 6-O-(carboxyacetyl)-beta-D-glucopyranosyl residue at position 7 via a glycosidic linkage.		2.1110glycosyloxyisoflavone;
hydroxyisoflavone;
malonate ester;
monosaccharide derivative		plant metabolite
malonylgenistin
malonylgenistin: structure in first source. malonylgenistin : A glycosyloxyisoflavone that is genistin in which the hydroxy hydrogen at position 6'' has been replaced by a malonyl group.		2.1110beta-D-glucoside;
glycosyloxyisoflavone;
hydroxyisoflavone;
malonate ester;
monosaccharide derivative		plant metabolite
ConditionIndicatedRelationship StrengthStudiesTrials
Diabetes Mellitus
A heterogeneous group of disorders characterized by HYPERGLYCEMIA and GLUCOSE INTOLERANCE.		02.0510
Acute Confusional Senile Dementia
[description not available]		02.5520
Alloxan Diabetes
[description not available]		02.110
Hyperglycemia, Postprandial
Abnormally high BLOOD GLUCOSE level after a meal.		02.110
Alzheimer Disease
A degenerative disease of the BRAIN characterized by the insidious onset of DEMENTIA. Impairment of MEMORY, judgment, attention span, and problem solving skills are followed by severe APRAXIAS and a global loss of cognitive abilities. The condition primarily occurs after age 60, and is marked pathologically by severe cortical atrophy and the triad of SENILE PLAQUES; NEUROFIBRILLARY TANGLES; and NEUROPIL THREADS. (From Adams et al., Principles of Neurology, 6th ed, pp1049-57)		02.5520
Hyperglycemia
Abnormally high BLOOD GLUCOSE level.		02.110
Diabetes Mellitus, Adult-Onset
[description not available]		02.2510
Diabetes Mellitus, Type 2
A subclass of DIABETES MELLITUS that is not INSULIN-responsive or dependent (NIDDM). It is characterized initially by INSULIN RESISTANCE and HYPERINSULINEMIA; and eventually by GLUCOSE INTOLERANCE; HYPERGLYCEMIA; and overt diabetes. Type II diabetes mellitus is no longer considered a disease exclusively found in adults. Patients seldom develop KETOSIS but often exhibit OBESITY.		02.2510