Compounds > Kushenol A
Page last updated: 2024-11-13

Kushenol A

Description

kushenol A: a tyrosinase inhibitor derived from Sophora flavescens [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID44563121
CHEMBL ID455679
CHEBI ID197206

Synonyms (17)

Synonym
kushenol a
CHEMBL455679
(2s)-5,7-dihydroxy-2-(2-hydroxyphenyl)-8-[(2r)-5-methyl-2-prop-1-en-2-ylhex-4-enyl]-2,3-dihydrochromen-4-one
CHEBI:197206
bdbm50377945
99217-63-7
AKOS032948966
HY-N2278
CS-0019607
MS-27020
DTXSID701318374
kushenola
(2s)-2,3-dihydro-5,7-dihydroxy-2-(2-hydroxyphenyl)-8-[(2r)-5-methyl-2-(1-methylethenyl)-4-hexen-1-yl]-4h-1-benzopyran-4-one
4h-1-benzopyran-4-one, 2,3-dihydro-5,7-dihydroxy-2-(2-hydroxyphenyl)-8-[(2r)-5-methyl-2-(1-methylethenyl)-4-hexen-1-yl]-, (2s)-
S7LW4HSS6R
4h-1-benzopyran-4-one, 2,3-dihydro-5,7-dihydroxy-2-(2-hydroxyphenyl)-8-[5-methyl-2-(1-methylethenyl)-4-hexenyl]-, [s-(r*,s*)]-
(-)-kushenol a
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
flavanonesMembers of the class of flavans with a 3,4-dihydro-2-aryl-2H-1-benzopyran-4-one skeleton and its substituted derivatives.
[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 (1)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Beta-secretase 1Homo sapiens (human)IC50 (µMol)2.60000.00061.619410.0000AID344054
Beta-secretase 1Homo sapiens (human)Ki3.00000.00031.35248.0000AID344054
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (16)

Processvia Protein(s)Taxonomy
proteolysisBeta-secretase 1Homo sapiens (human)
membrane protein ectodomain proteolysisBeta-secretase 1Homo sapiens (human)
response to lead ionBeta-secretase 1Homo sapiens (human)
protein processingBeta-secretase 1Homo sapiens (human)
amyloid-beta formationBeta-secretase 1Homo sapiens (human)
amyloid precursor protein catabolic processBeta-secretase 1Homo sapiens (human)
positive regulation of neuron apoptotic processBeta-secretase 1Homo sapiens (human)
amyloid-beta metabolic processBeta-secretase 1Homo sapiens (human)
detection of mechanical stimulus involved in sensory perception of painBeta-secretase 1Homo sapiens (human)
prepulse inhibitionBeta-secretase 1Homo sapiens (human)
cellular response to copper ionBeta-secretase 1Homo sapiens (human)
cellular response to manganese ionBeta-secretase 1Homo sapiens (human)
presynaptic modulation of chemical synaptic transmissionBeta-secretase 1Homo sapiens (human)
signaling receptor ligand precursor processingBeta-secretase 1Homo sapiens (human)
cellular response to amyloid-betaBeta-secretase 1Homo sapiens (human)
amyloid fibril formationBeta-secretase 1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (8)

Processvia Protein(s)Taxonomy
amyloid-beta bindingBeta-secretase 1Homo sapiens (human)
endopeptidase activityBeta-secretase 1Homo sapiens (human)
aspartic-type endopeptidase activityBeta-secretase 1Homo sapiens (human)
protein bindingBeta-secretase 1Homo sapiens (human)
peptidase activityBeta-secretase 1Homo sapiens (human)
beta-aspartyl-peptidase activityBeta-secretase 1Homo sapiens (human)
enzyme bindingBeta-secretase 1Homo sapiens (human)
protein serine/threonine kinase bindingBeta-secretase 1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (20)

Processvia Protein(s)Taxonomy
lysosomeBeta-secretase 1Homo sapiens (human)
endosomeBeta-secretase 1Homo sapiens (human)
early endosomeBeta-secretase 1Homo sapiens (human)
late endosomeBeta-secretase 1Homo sapiens (human)
multivesicular bodyBeta-secretase 1Homo sapiens (human)
endoplasmic reticulum lumenBeta-secretase 1Homo sapiens (human)
Golgi apparatusBeta-secretase 1Homo sapiens (human)
trans-Golgi networkBeta-secretase 1Homo sapiens (human)
plasma membraneBeta-secretase 1Homo sapiens (human)
synaptic vesicleBeta-secretase 1Homo sapiens (human)
cell surfaceBeta-secretase 1Homo sapiens (human)
endosome membraneBeta-secretase 1Homo sapiens (human)
membraneBeta-secretase 1Homo sapiens (human)
axonBeta-secretase 1Homo sapiens (human)
dendriteBeta-secretase 1Homo sapiens (human)
neuronal cell bodyBeta-secretase 1Homo sapiens (human)
membrane raftBeta-secretase 1Homo sapiens (human)
recycling endosomeBeta-secretase 1Homo sapiens (human)
Golgi-associated vesicle lumenBeta-secretase 1Homo sapiens (human)
hippocampal mossy fiber to CA3 synapseBeta-secretase 1Homo sapiens (human)
endosomeBeta-secretase 1Homo sapiens (human)
plasma membraneBeta-secretase 1Homo sapiens (human)
trans-Golgi networkBeta-secretase 1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (5)

Assay IDTitleYearJournalArticle
AID344054Inhibition of human BACE12008Bioorganic & medicinal chemistry, Jul-15, Volume: 16, Issue:14
BACE1 inhibitory effects of lavandulyl flavanones from Sophora flavescens.
AID344052Inhibition of human BACE1 expressed in HEK293 cells assessed as reduction in soluble APPalpha level after 4 hrs by Western blot analysis2008Bioorganic & medicinal chemistry, Jul-15, Volume: 16, Issue:14
BACE1 inhibitory effects of lavandulyl flavanones from Sophora flavescens.
AID410031Inhibition of Clostridium perfringens neuraminidase2008Bioorganic & medicinal chemistry letters, Dec-01, Volume: 18, Issue:23
Pterocarpans and flavanones from Sophora flavescens displaying potent neuraminidase inhibition.
AID410032Inhibition of Clostridium perfringens neuraminidase by Lineweaver-Burke plot2008Bioorganic & medicinal chemistry letters, Dec-01, Volume: 18, Issue:23
Pterocarpans and flavanones from Sophora flavescens displaying potent neuraminidase inhibition.
AID344053Inhibition of human BACE1 expressed in HEK293 cells assessed as reduction in soluble APPbeta level after 4 hrs by Western blot analysis2008Bioorganic & medicinal chemistry, Jul-15, Volume: 16, Issue:14
BACE1 inhibitory effects of lavandulyl flavanones from Sophora flavescens.
[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's2 (40.00)29.6817
2010's1 (20.00)24.3611
2020's2 (40.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 13.16

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 Index13.16 (24.57)
Research Supply Index1.79 (2.92)
Research Growth Index4.95 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (13.16)

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
glucose, (beta-d)-isomer
beta-D-glucose : D-Glucopyranose with beta configuration at the anomeric centre.. (1->4)-beta-D-glucan : A beta-D-glucan in which the glucose units are connected by (1->4) linkages.. (1->3)-beta-D-glucan : A beta-D-glucan in which the glucose units are connected by (1->3) linkages.		2.3110D-glucopyranoseepitope;
mouse metabolite
vexibinol
vexibinol: flavanol from Sophora; structure in first source; RN given refers to (S-(R*,S*))-isomer. sophoraflavanone G : A tetrahydroxyflavanone having a structure of naringenin bearing an additional hydroxyl substituent at position 2' as well as a (2R)-5-methyl-2-(prop-1-en-2-yl)hex-4-en-1-yl (lavandulyl) substituent at position 8'.		2.4420(2S)-flavan-4-one;
4'-hydroxyflavanones;
tetrahydroxyflavanone		antimalarial;
antimicrobial agent;
antioxidant;
plant metabolite
inermin
inermin: phytoalexin produced in plants after injection with fungi; RN given refers to (cis-(+-))-isomer; RN for cpd without isomeric designation; structure. (-)-maackiain : The (-)-enantiomer of maackiain.		2.5120maackiain
trifolirhizin
trifolirhizin: from Sophora flavescens; has inhibitory effect on tyrosinase and melanin synthesis; structure in first source		2.5120pterocarpans
isoxanthohumol
isoxanthohumol: structure in first source		2.0410flavanones
mangiferin
shamimin: isolated from the leaves of Bombax ceiba; structure in first source		2.0410C-glycosyl compound;
xanthones		anti-inflammatory agent;
antioxidant;
hypoglycemic agent;
plant metabolite
desmethylicaritin
desmethylicaritin: structure in first source		2.1710
2'-methoxykurarinone
2'-methoxykurarinone: cytotoxic lavandulyl flavanone from Sophora flavescens; structure in first source. (2S)-2'-methoxykurarinone : A dimethoxyflavanone that is (2S)-(-)-kurarinone in which the hydroxy group at position 2' is replaced by a methoxy group. Isolated from the roots of Sophora flavescens, it exhibits cytotoxicity against human myeloid leukemia HL-60 cells.		2.04104'-hydroxyflavanones;
dihydroxyflavanone;
dimethoxyflavanone		antineoplastic agent;
metabolite
oxymatrine
oxymatrine: structure in first source; has anti-apoptosis effects		2.3110
kurarinol
kurarinol: from Sophora flavescens; has inhibitory effect on tyrosinase and melanin synthesis; structure in first source. kurarinol : A trihydroxyflavanone that is (2S)-flavanone substituted by hydroxy groups at positions 7, 2' and 4' , a methoxy group at position 5 and a (2S)-5-hydroxy-5-methyl-2-(prop-1-en-2-yl)hexyl group at position 8 respectively.		2.44204'-hydroxyflavanones;
monomethoxyflavanone;
trihydroxyflavanone		anti-inflammatory agent;
antioxidant;
plant metabolite
leachianone a
leachianone A: isolated from the Chinese herbal medicine Radix Sophorae; structure in first source. leachianone A : A trihydroxyflavanone that is (2S)-flavanone substituted by a lavandulyl group at position 8, hydroxy groups at positions 5, 7 and 4' and a methoxy group at position 2'. Isolated from the roots of Sophora flavescens and Sophora leachiana, it exhibits antineoplastic and antimalarial activity.		2.44204'-hydroxyflavanones;
monomethoxyflavanone;
trihydroxyflavanone		antimalarial;
antineoplastic agent;
metabolite
ConditionIndicatedRelationship StrengthStudiesTrials
Acute Confusional Senile Dementia
[description not available]		02.0410
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)		02.0410
Breast Cancer
[description not available]		07.610
Breast Neoplasms
Tumors or cancer of the human BREAST.		02.610
chemdatabank.com