Compounds > 2,3-dehydrosilybin
Page last updated: 2024-11-11

2,3-dehydrosilybin

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

Description

dehydrosilybin: inhibits cytochrome P450 1A1 catalytic activity; structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID5467200
CHEMBL ID38464
CHEBI ID172705
SCHEMBL ID936621
MeSH IDM0500595

Synonyms (16)

Synonym
3,5,7-trihydroxy-2-[3-(4-hydroxy-3-methoxyphenyl)-2-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl]chromen-4-one
CHEBI:172705
NCI60_016767
quercetin 3',4'-coniferyl
nsc648334
nsc-648334
2,3-dehydrosilybin
bdbm50084979
3,5,7-trihydroxy-2-[3-(4-hydroxy-3-methoxy-phenyl)-2-hydroxymethyl-2,3-dihydro-benzo[1,4]dioxin-6-yl]-chromen-4-one
dehydrosilybin
CHEMBL38464 ,
dehydrosilylbin
SCHEMBL936621
3,5,7-trihydroxy-2-[3-(4-hydroxy-3-methoxyphenyl)-2-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl]-4h-chromen-4-one
25166-14-7
2,3-dehydrosilybin a
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
flavonolignanAny lignan condensed with a 2-aryl-1-benzopyran 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 (3)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Xanthine dehydrogenase/oxidase [Includes: Xanthine dehydrogenase Rattus norvegicus (Norway rat)IC50 (µMol)80.30000.00402.25236.0000AID449301
Multidrug resistance-associated protein 1 Homo sapiens (human)IC50 (µMol)1.10000.00153.71109.6600AID421553
[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)
ATP-dependent translocase ABCB1Mus musculus (house mouse)Kd2.20002.20005.18336.8000AID150738
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (23)

Processvia Protein(s)Taxonomy
leukotriene metabolic processMultidrug resistance-associated protein 1 Homo sapiens (human)
xenobiotic metabolic processMultidrug resistance-associated protein 1 Homo sapiens (human)
response to xenobiotic stimulusMultidrug resistance-associated protein 1 Homo sapiens (human)
cobalamin transportMultidrug resistance-associated protein 1 Homo sapiens (human)
sphingolipid biosynthetic processMultidrug resistance-associated protein 1 Homo sapiens (human)
cellular response to oxidative stressMultidrug resistance-associated protein 1 Homo sapiens (human)
heme catabolic processMultidrug resistance-associated protein 1 Homo sapiens (human)
xenobiotic transportMultidrug resistance-associated protein 1 Homo sapiens (human)
phospholipid translocationMultidrug resistance-associated protein 1 Homo sapiens (human)
positive regulation of inflammatory responseMultidrug resistance-associated protein 1 Homo sapiens (human)
transmembrane transportMultidrug resistance-associated protein 1 Homo sapiens (human)
cell chemotaxisMultidrug resistance-associated protein 1 Homo sapiens (human)
transepithelial transportMultidrug resistance-associated protein 1 Homo sapiens (human)
cyclic nucleotide transportMultidrug resistance-associated protein 1 Homo sapiens (human)
leukotriene transportMultidrug resistance-associated protein 1 Homo sapiens (human)
monoatomic anion transmembrane transportMultidrug resistance-associated protein 1 Homo sapiens (human)
sphingolipid translocationMultidrug resistance-associated protein 1 Homo sapiens (human)
export across plasma membraneMultidrug resistance-associated protein 1 Homo sapiens (human)
transport across blood-brain barrierMultidrug resistance-associated protein 1 Homo sapiens (human)
cellular response to amyloid-betaMultidrug resistance-associated protein 1 Homo sapiens (human)
carboxylic acid transmembrane transportMultidrug resistance-associated protein 1 Homo sapiens (human)
xenobiotic transport across blood-brain barrierMultidrug resistance-associated protein 1 Homo sapiens (human)
glutathione transmembrane transportMultidrug resistance-associated protein 1 Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (14)

Processvia Protein(s)Taxonomy
ATPase-coupled transmembrane transporter activityATP-dependent translocase ABCB1Mus musculus (house mouse)
ATP bindingMultidrug resistance-associated protein 1 Homo sapiens (human)
ABC-type vitamin B12 transporter activityMultidrug resistance-associated protein 1 Homo sapiens (human)
ABC-type glutathione S-conjugate transporter activityMultidrug resistance-associated protein 1 Homo sapiens (human)
efflux transmembrane transporter activityMultidrug resistance-associated protein 1 Homo sapiens (human)
ATP hydrolysis activityMultidrug resistance-associated protein 1 Homo sapiens (human)
ATPase-coupled lipid transmembrane transporter activityMultidrug resistance-associated protein 1 Homo sapiens (human)
glutathione transmembrane transporter activityMultidrug resistance-associated protein 1 Homo sapiens (human)
ATPase-coupled transmembrane transporter activityMultidrug resistance-associated protein 1 Homo sapiens (human)
xenobiotic transmembrane transporter activityMultidrug resistance-associated protein 1 Homo sapiens (human)
ATPase-coupled inorganic anion transmembrane transporter activityMultidrug resistance-associated protein 1 Homo sapiens (human)
sphingolipid transporter activityMultidrug resistance-associated protein 1 Homo sapiens (human)
carboxylic acid transmembrane transporter activityMultidrug resistance-associated protein 1 Homo sapiens (human)
ABC-type transporter activityMultidrug resistance-associated protein 1 Homo sapiens (human)
ABC-type xenobiotic transporter activityMultidrug resistance-associated protein 1 Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (7)

Processvia Protein(s)Taxonomy
plasma membraneATP-dependent translocase ABCB1Mus musculus (house mouse)
plasma membraneMultidrug resistance-associated protein 1 Homo sapiens (human)
basal plasma membraneMultidrug resistance-associated protein 1 Homo sapiens (human)
membraneMultidrug resistance-associated protein 1 Homo sapiens (human)
basolateral plasma membraneMultidrug resistance-associated protein 1 Homo sapiens (human)
apical plasma membraneMultidrug resistance-associated protein 1 Homo sapiens (human)
lateral plasma membraneMultidrug resistance-associated protein 1 Homo sapiens (human)
extracellular exosomeMultidrug resistance-associated protein 1 Homo sapiens (human)
basolateral plasma membraneMultidrug resistance-associated protein 1 Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (58)

Assay IDTitleYearJournalArticle
AID1306208Induction of apoptosis in human PC3 cells assessed as viable cells at 40 uM after 15 to 16 hrs by F2N12S and SYTOX AADvanced double staining based flow cytometry (Rvb = 94 %)2016Bioorganic & medicinal chemistry letters, 07-15, Volume: 26, Issue:14
3-O-Alkyl-2,3-dehydrosilibinins: Two synthetic approaches and in vitro effects toward prostate cancer cells.
AID1306213Induction of apoptosis in human PC3 cells assessed as late apoptotic/necrotic cells at 60 uM after 15 to 16 hrs by F2N12S and SYTOX AADvanced double staining based flow cytometry (Rvb = 3 %)2016Bioorganic & medicinal chemistry letters, 07-15, Volume: 26, Issue:14
3-O-Alkyl-2,3-dehydrosilibinins: Two synthetic approaches and in vitro effects toward prostate cancer cells.
AID1306209Induction of apoptosis in human PC3 cells assessed as early apoptotic cells at 40 uM after 15 to 16 hrs by F2N12S and SYTOX AADvanced double staining based flow cytometry (Rvb = 2 to 3 %)2016Bioorganic & medicinal chemistry letters, 07-15, Volume: 26, Issue:14
3-O-Alkyl-2,3-dehydrosilibinins: Two synthetic approaches and in vitro effects toward prostate cancer cells.
AID449299Neuroprotective activity against H2O2-induced injury in rat PC12 cells treated 2 hrs before H2O2 challenge measured after 4 hrs by MTT assay2009Journal of medicinal chemistry, Dec-10, Volume: 52, Issue:23
Design, synthesis, and examination of neuron protective properties of alkenylated and amidated dehydro-silybin derivatives.
AID1306211Induction of apoptosis in human PC3 cells assessed as viable cells at 60 uM after 15 to 16 hrs by F2N12S and SYTOX AADvanced double staining based flow cytometry (Rvb = 94 %)2016Bioorganic & medicinal chemistry letters, 07-15, Volume: 26, Issue:14
3-O-Alkyl-2,3-dehydrosilibinins: Two synthetic approaches and in vitro effects toward prostate cancer cells.
AID1306212Induction of apoptosis in human PC3 cells assessed as early apoptotic cells at 60 uM after 15 to 16 hrs by F2N12S and SYTOX AADvanced double staining based flow cytometry (Rvb = 2 to 3 %)2016Bioorganic & medicinal chemistry letters, 07-15, Volume: 26, Issue:14
3-O-Alkyl-2,3-dehydrosilibinins: Two synthetic approaches and in vitro effects toward prostate cancer cells.
AID1635053Antimigratory activity in HUVEC assessed as inhibition of cell migration measured after 16 to 20 hrs by crystal violet staining-based microscopic analysis2016Journal of natural products, Apr-22, Volume: 79, Issue:4
Effects of 2,3-Dehydrosilybin and Its Galloyl Ester and Methyl Ether Derivatives on Human Umbilical Vein Endothelial Cells.
AID1306224Potency index, ratio of silibinin IC50 to compound IC50 for human DU145 cells2016Bioorganic & medicinal chemistry letters, 07-15, Volume: 26, Issue:14
3-O-Alkyl-2,3-dehydrosilibinins: Two synthetic approaches and in vitro effects toward prostate cancer cells.
AID1306207Induction of apoptosis in human PC3 cells assessed as late apoptotic/necrotic cells at 20 uM after 15 to 16 hrs by F2N12S and SYTOX AADvanced double staining based flow cytometry (Rvb = 3 %)2016Bioorganic & medicinal chemistry letters, 07-15, Volume: 26, Issue:14
3-O-Alkyl-2,3-dehydrosilibinins: Two synthetic approaches and in vitro effects toward prostate cancer cells.
AID1635057Antimigratory activity in HUVEC assessed as inhibition of cell migration at 10 uM measured after 16 to 20 hrs by crystal violet staining-based microscopic analysis2016Journal of natural products, Apr-22, Volume: 79, Issue:4
Effects of 2,3-Dehydrosilybin and Its Galloyl Ester and Methyl Ether Derivatives on Human Umbilical Vein Endothelial Cells.
AID1306222Antiproliferative activity against human PC3 cells assessed as reduction in cell viability after 3 days by WST-1 assay2016Bioorganic & medicinal chemistry letters, 07-15, Volume: 26, Issue:14
3-O-Alkyl-2,3-dehydrosilibinins: Two synthetic approaches and in vitro effects toward prostate cancer cells.
AID1428434Cytotoxicity against human MCF7 cells at 0.0003 to 100 uM after 48 hrs by ATPlite assay2016Journal of natural products, Dec-23, Volume: 79, Issue:12
Silychristin: Skeletal Alterations and Biological Activities.
AID1428431Cytotoxicity against human K562 cells at 0.0003 to 100 uM after 48 hrs by ATPlite assay2016Journal of natural products, Dec-23, Volume: 79, Issue:12
Silychristin: Skeletal Alterations and Biological Activities.
AID1306226Cell cycle arrest in human PC3 cells assessed as accumulation at G0/G1 phase at 50 uM after 16 hrs by propidium iodide staining based flow cytometry (Rvb = 48 %)2016Bioorganic & medicinal chemistry letters, 07-15, Volume: 26, Issue:14
3-O-Alkyl-2,3-dehydrosilibinins: Two synthetic approaches and in vitro effects toward prostate cancer cells.
AID1428436Cytotoxicity against human primary prostate mesenchymal cells at 0.0003 to 100 uM after 48 hrs by ATPlite assay2016Journal of natural products, Dec-23, Volume: 79, Issue:12
Silychristin: Skeletal Alterations and Biological Activities.
AID1428426Antioxidant activity against tert-butyl hydroperoxide-induced lipoperoxidation in rat liver microsomal membranes incubated for 60 mins by TBARS assay2016Journal of natural products, Dec-23, Volume: 79, Issue:12
Silychristin: Skeletal Alterations and Biological Activities.
AID1306219Induction of apoptosis in human PC3 cells assessed as late apoptotic/necrotic cells at 100 uM after 15 to 16 hrs by F2N12S and SYTOX AADvanced double staining based flow cytometry (Rvb = 3 %)2016Bioorganic & medicinal chemistry letters, 07-15, Volume: 26, Issue:14
3-O-Alkyl-2,3-dehydrosilibinins: Two synthetic approaches and in vitro effects toward prostate cancer cells.
AID1428433Cytotoxicity against human MDA-MB-231 cells at 0.0003 to 100 uM after 48 hrs by ATPlite assay2016Journal of natural products, Dec-23, Volume: 79, Issue:12
Silychristin: Skeletal Alterations and Biological Activities.
AID1428432Cytotoxicity against human HL60 cells at 0.0003 to 100 uM after 48 hrs by ATPlite assay2016Journal of natural products, Dec-23, Volume: 79, Issue:12
Silychristin: Skeletal Alterations and Biological Activities.
AID1428424Antioxidant activity assessed as trolox equivalent of ABTS radical scavenging activity at 100 uM incubated for >= 5 mins2016Journal of natural products, Dec-23, Volume: 79, Issue:12
Silychristin: Skeletal Alterations and Biological Activities.
AID1306229Cell cycle arrest in human PC3 cells assessed as accumulation at G2 phase at 50 uM after 24 hrs by propidium iodide staining based flow cytometry (Rvb = 21 %)2016Bioorganic & medicinal chemistry letters, 07-15, Volume: 26, Issue:14
3-O-Alkyl-2,3-dehydrosilibinins: Two synthetic approaches and in vitro effects toward prostate cancer cells.
AID1428435Cytotoxicity against human CAL51 at 0.0003 to 100 uM after 48 hrs by ATPlite assay2016Journal of natural products, Dec-23, Volume: 79, Issue:12
Silychristin: Skeletal Alterations and Biological Activities.
AID1306228Cell cycle arrest in human PC3 cells assessed as accumulation at G0/G1 phase at 50 uM after 24 hrs by propidium iodide staining based flow cytometry (Rvb = 60 %)2016Bioorganic & medicinal chemistry letters, 07-15, Volume: 26, Issue:14
3-O-Alkyl-2,3-dehydrosilibinins: Two synthetic approaches and in vitro effects toward prostate cancer cells.
AID609843Octanol-water partition coefficient, log P of the compound at pH 7.4 by stir-flask method2011Bioorganic & medicinal chemistry letters, Aug-01, Volume: 21, Issue:15
New C-23 modified of silybin and 2,3-dehydrosilybin: synthesis and preliminary evaluation of antioxidant properties.
AID449287Antioxidant activity assessed as DPPH radical scavenging activity at 50 uM after 30 mins by spectrophotometry2009Journal of medicinal chemistry, Dec-10, Volume: 52, Issue:23
Design, synthesis, and examination of neuron protective properties of alkenylated and amidated dehydro-silybin derivatives.
AID609844Cytotoxicity against rat immortalized Rat1 cells after 48 hrs by MTT assay2011Bioorganic & medicinal chemistry letters, Aug-01, Volume: 21, Issue:15
New C-23 modified of silybin and 2,3-dehydrosilybin: synthesis and preliminary evaluation of antioxidant properties.
AID1306220Antiproliferative activity against human LNCAP cells assessed as reduction in cell viability after 3 days by WST-1 assay2016Bioorganic & medicinal chemistry letters, 07-15, Volume: 26, Issue:14
3-O-Alkyl-2,3-dehydrosilibinins: Two synthetic approaches and in vitro effects toward prostate cancer cells.
AID1306215Induction of apoptosis in human PC3 cells assessed as early apoptotic cells at 80 uM after 15 to 16 hrs by F2N12S and SYTOX AADvanced double staining based flow cytometry (Rvb = 2 to 3 %)2016Bioorganic & medicinal chemistry letters, 07-15, Volume: 26, Issue:14
3-O-Alkyl-2,3-dehydrosilibinins: Two synthetic approaches and in vitro effects toward prostate cancer cells.
AID449298Neuroprotective activity against H2O2-induced injury in rat PC12 cells assessed as increase in cell viability at 50 uM treated 2 hrs before H2O2 challenge measured after 4 hrs by MTT assay2009Journal of medicinal chemistry, Dec-10, Volume: 52, Issue:23
Design, synthesis, and examination of neuron protective properties of alkenylated and amidated dehydro-silybin derivatives.
AID1635051Cytotoxicity in HUVEC assessed as reduction in cell viability measured after 24 hrs by MTT assay2016Journal of natural products, Apr-22, Volume: 79, Issue:4
Effects of 2,3-Dehydrosilybin and Its Galloyl Ester and Methyl Ether Derivatives on Human Umbilical Vein Endothelial Cells.
AID1306227Cell cycle arrest in human PC3 cells assessed as accumulation at G2 phase at 50 uM after 16 hrs by propidium iodide staining based flow cytometry (Rvb = 31 %)2016Bioorganic & medicinal chemistry letters, 07-15, Volume: 26, Issue:14
3-O-Alkyl-2,3-dehydrosilibinins: Two synthetic approaches and in vitro effects toward prostate cancer cells.
AID1428428Cytotoxicity against human BJ cells at 0.0003 to 100 uM after 48 hrs by ATPlite assay2016Journal of natural products, Dec-23, Volume: 79, Issue:12
Silychristin: Skeletal Alterations and Biological Activities.
AID1306223Potency index, ratio of silibinin IC50 to compound IC50 for human LNCAP cells2016Bioorganic & medicinal chemistry letters, 07-15, Volume: 26, Issue:14
3-O-Alkyl-2,3-dehydrosilibinins: Two synthetic approaches and in vitro effects toward prostate cancer cells.
AID449291Inhibition of lipid peroxidation in Sprague-Dawley rat liver homogenate assessed as malondialdehyde formation after 1 hr by TBARS assay2009Journal of medicinal chemistry, Dec-10, Volume: 52, Issue:23
Design, synthesis, and examination of neuron protective properties of alkenylated and amidated dehydro-silybin derivatives.
AID1306217Induction of apoptosis in human PC3 cells assessed as viable cells at 100 uM after 15 to 16 hrs by F2N12S and SYTOX AADvanced double staining based flow cytometry (Rvb = 94 %)2016Bioorganic & medicinal chemistry letters, 07-15, Volume: 26, Issue:14
3-O-Alkyl-2,3-dehydrosilibinins: Two synthetic approaches and in vitro effects toward prostate cancer cells.
AID1306206Induction of apoptosis in human PC3 cells assessed as early apoptotic cells at 20 uM after 15 to 16 hrs by F2N12S and SYTOX AADvanced double staining based flow cytometry (Rvb = 2 to 3 %)2016Bioorganic & medicinal chemistry letters, 07-15, Volume: 26, Issue:14
3-O-Alkyl-2,3-dehydrosilibinins: Two synthetic approaches and in vitro effects toward prostate cancer cells.
AID1306214Induction of apoptosis in human PC3 cells assessed as viable cells at 80 uM after 15 to 16 hrs by F2N12S and SYTOX AADvanced double staining based flow cytometry (Rvb = 94 %)2016Bioorganic & medicinal chemistry letters, 07-15, Volume: 26, Issue:14
3-O-Alkyl-2,3-dehydrosilibinins: Two synthetic approaches and in vitro effects toward prostate cancer cells.
AID1306210Induction of apoptosis in human PC3 cells assessed as late apoptotic/necrotic cells at 40 uM after 15 to 16 hrs by F2N12S and SYTOX AADvanced double staining based flow cytometry (Rvb = 3 %)2016Bioorganic & medicinal chemistry letters, 07-15, Volume: 26, Issue:14
3-O-Alkyl-2,3-dehydrosilibinins: Two synthetic approaches and in vitro effects toward prostate cancer cells.
AID1428430Cytotoxicity against human HepG2 cells at 0.0003 to 100 uM after 48 hrs by ATPlite assay2016Journal of natural products, Dec-23, Volume: 79, Issue:12
Silychristin: Skeletal Alterations and Biological Activities.
AID1306221Antiproliferative activity against human DU145 cells assessed as reduction in cell viability after 3 days by WST-1 assay2016Bioorganic & medicinal chemistry letters, 07-15, Volume: 26, Issue:14
3-O-Alkyl-2,3-dehydrosilibinins: Two synthetic approaches and in vitro effects toward prostate cancer cells.
AID1428422Antiradical activity assessed as gallic acid equivalents of Foline-Ciocalteu reagent reducing capacity at 1 mM preincubated for 5 mins followed by Na2CO3 addition measured after 90 mins2016Journal of natural products, Dec-23, Volume: 79, Issue:12
Silychristin: Skeletal Alterations and Biological Activities.
AID449296Iron chelating activity assessed as inhibition of ferrozine-Fe2+ complex formation after 10 mins by spectrophotometry2009Journal of medicinal chemistry, Dec-10, Volume: 52, Issue:23
Design, synthesis, and examination of neuron protective properties of alkenylated and amidated dehydro-silybin derivatives.
AID1428427Cytotoxicity against human RPE1 cells at 0.0003 to 100 uM after 48 hrs by ATPlite assay2016Journal of natural products, Dec-23, Volume: 79, Issue:12
Silychristin: Skeletal Alterations and Biological Activities.
AID150738Compound was tested for the binding affinity towards recombinant NBD2 C-terminal cytotoxic nucleotide-binding domain of mouse P-Glycoprotein2000Bioorganic & medicinal chemistry letters, Jan-17, Volume: 10, Issue:2
The flavanolignan silybin and its hemisynthetic derivatives, a novel series of potential modulators of P-glycoprotein.
AID1306216Induction of apoptosis in human PC3 cells assessed as late apoptotic/necrotic cells at 80 uM after 15 to 16 hrs by F2N12S and SYTOX AADvanced double staining based flow cytometry (Rvb = 3 %)2016Bioorganic & medicinal chemistry letters, 07-15, Volume: 26, Issue:14
3-O-Alkyl-2,3-dehydrosilibinins: Two synthetic approaches and in vitro effects toward prostate cancer cells.
AID1635052Antiproliferative activity in HUVEC assessed as reduction in cell viability measured after 72 hrs by MTT assay2016Journal of natural products, Apr-22, Volume: 79, Issue:4
Effects of 2,3-Dehydrosilybin and Its Galloyl Ester and Methyl Ether Derivatives on Human Umbilical Vein Endothelial Cells.
AID1428425Partition coefficient, logP of the compound in octan-1-ol and phosphate buffer at pH 7.4 at 25 degC after 2 hrs by UV-vis spectrometer2016Journal of natural products, Dec-23, Volume: 79, Issue:12
Silychristin: Skeletal Alterations and Biological Activities.
AID1306225Potency index, ratio of silibinin IC50 to compound IC50 for human PC3 cells2016Bioorganic & medicinal chemistry letters, 07-15, Volume: 26, Issue:14
3-O-Alkyl-2,3-dehydrosilibinins: Two synthetic approaches and in vitro effects toward prostate cancer cells.
AID1428423Antioxidant activity assessed as DPPH radical scavenging activity after 30 mins2016Journal of natural products, Dec-23, Volume: 79, Issue:12
Silychristin: Skeletal Alterations and Biological Activities.
AID449295Iron chelating activity assessed as inhibition of ferrozine-Fe2+ complex formation at 150 uM after 10 mins by spectrophotometry2009Journal of medicinal chemistry, Dec-10, Volume: 52, Issue:23
Design, synthesis, and examination of neuron protective properties of alkenylated and amidated dehydro-silybin derivatives.
AID609872Cytotoxicity against rat immortalized Rat1 cells assessed as reduction of cell viability at 30 uM after 48 hrs by MTT assay2011Bioorganic & medicinal chemistry letters, Aug-01, Volume: 21, Issue:15
New C-23 modified of silybin and 2,3-dehydrosilybin: synthesis and preliminary evaluation of antioxidant properties.
AID1306205Induction of apoptosis in human PC3 cells assessed as viable cells at 20 uM after 15 to 16 hrs by F2N12S and SYTOX AADvanced double staining based flow cytometry (Rvb = 94 %)2016Bioorganic & medicinal chemistry letters, 07-15, Volume: 26, Issue:14
3-O-Alkyl-2,3-dehydrosilibinins: Two synthetic approaches and in vitro effects toward prostate cancer cells.
AID233143Change in Fmax was determined2000Bioorganic & medicinal chemistry letters, Jan-17, Volume: 10, Issue:2
The flavanolignan silybin and its hemisynthetic derivatives, a novel series of potential modulators of P-glycoprotein.
AID421553Inhibition of MRP12009Journal of medicinal chemistry, Aug-13, Volume: 52, Issue:15
Aromatic 2-(thio)ureidocarboxylic acids as a new family of modulators of multidrug resistance-associated protein 1: synthesis, biological evaluation, and structure-activity relationships.
AID609842Antioxidant activity in rat immortalized Rat1 cells assessed as inhibition of hydrogen peroxide-induced reactive oxygen species production by measuring conversion of 2',7'-dichlorofluorescin diacetate into 2',7'-dichlorofluorescein at 30 uM treated 48 hrs2011Bioorganic & medicinal chemistry letters, Aug-01, Volume: 21, Issue:15
New C-23 modified of silybin and 2,3-dehydrosilybin: synthesis and preliminary evaluation of antioxidant properties.
AID449301Inhibition of rat liver xanthine oxidase after 2 hrs by spectrophotometry2009Journal of medicinal chemistry, Dec-10, Volume: 52, Issue:23
Design, synthesis, and examination of neuron protective properties of alkenylated and amidated dehydro-silybin derivatives.
AID1428429Cytotoxicity against human PC3 cells at 0.0003 to 100 uM after 48 hrs by ATPlite assay2016Journal of natural products, Dec-23, Volume: 79, Issue:12
Silychristin: Skeletal Alterations and Biological Activities.
AID1306218Induction of apoptosis in human PC3 cells assessed as early apoptotic cells at 100 uM after 15 to 16 hrs by F2N12S and SYTOX AADvanced double staining based flow cytometry (Rvb = 2 to 3 %)2016Bioorganic & medicinal chemistry letters, 07-15, Volume: 26, Issue:14
3-O-Alkyl-2,3-dehydrosilibinins: Two synthetic approaches and in vitro effects toward prostate cancer cells.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (25)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's7 (28.00)29.6817
2010's18 (72.00)24.3611
2020's0 (0.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 12.12

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 Index12.12 (24.57)
Research Supply Index3.26 (2.92)
Research Growth Index5.38 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.12)

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%
Other25 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
gallic acid
gallate : A trihydroxybenzoate that is the conjugate base of gallic acid.		2.1310trihydroxybenzoic acidantineoplastic agent;
antioxidant;
apoptosis inducer;
astringent;
cyclooxygenase 2 inhibitor;
EC 1.13.11.33 (arachidonate 15-lipoxygenase) inhibitor;
geroprotector;
human xenobiotic metabolite;
plant metabolite
1-anilino-8-naphthalenesulfonate
1-anilino-8-naphthalenesulfonate: RN given refers to parent cpd. 8-anilinonaphthalene-1-sulfonic acid : A naphthalenesulfonic acid that is naphthalene-1-sulfonic acid substituted by a phenylamino group at position 8.		2.110aminonaphthalene;
naphthalenesulfonic acid		fluorescent probe
carbon tetrachloride
Carbon Tetrachloride: A solvent for oils, fats, lacquers, varnishes, rubber waxes, and resins, and a starting material in the manufacturing of organic compounds. Poisoning by inhalation, ingestion or skin absorption is possible and may be fatal. (Merck Index, 11th ed). tetrachloromethane : A chlorocarbon that is methane in which all the hydrogens have been replaced by chloro groups.		2.0610chlorocarbon;
chloromethanes		hepatotoxic agent;
refrigerant
carbostyril
Quinolones: A group of derivatives of naphthyridine carboxylic acid, quinoline carboxylic acid, or NALIDIXIC ACID.. quinolin-2(1H)-one : A quinolone that is 1,2-dihydroquinoline substituted by an oxo group at position 2.		2.0410monohydroxyquinoline;
quinolone		bacterial xenobiotic metabolite
rotenone
Derris: A plant genus of the family FABACEAE. The root is a source of rotenoids (ROTENONE) and flavonoids. Some species of Pongamia have been reclassified to this genus and some to MILLETTIA. Some species of Deguelia have been reclassified to this genus.. rotenoid : Members of the class of tetrahydrochromenochromene that consists of a cis-fused tetrahydrochromeno[3,4-b]chromene skeleton and its substituted derivatives. The term was originally restricted to natural products, but is now also used to describe semi-synthetic and fully synthetic compounds.		2.0510organic heteropentacyclic compound;
rotenones		antineoplastic agent;
metabolite;
mitochondrial NADH:ubiquinone reductase inhibitor;
phytogenic insecticide;
piscicide;
toxin
quinoxalines
quinoxaline : A naphthyridine in which the nitrogens are at positions 1 and 4.		2.0410mancude organic heterobicyclic parent;
naphthyridine;
ortho-fused heteroarene
pyrroles
1H-pyrrole : A tautomer of pyrrole that has the double bonds at positions 2 and 4.. pyrrole : A five-membered monocyclic heteroarene comprising one NH and four CH units which forms the parent compound of the pyrrole group of compounds. Its five-membered ring structure has three tautomers. A 'closed class'.. azole : Any monocyclic heteroarene consisting of a five-membered ring containing nitrogen. Azoles can also contain one or more other non-carbon atoms, such as nitrogen, sulfur or oxygen.		2.0410pyrrole;
secondary amine
thiophenes
Thiophenes: A monocyclic heteroarene furan in which the oxygen atom is replaced by a sulfur.. thiophenes : Compounds containing at least one thiophene ring.		2.0410mancude organic heteromonocyclic parent;
monocyclic heteroarene;
thiophenes;
volatile organic compound		non-polar solvent
isoxazoles
Isoxazoles: Azoles with an OXYGEN and a NITROGEN next to each other at the 1,2 positions, in contrast to OXAZOLES that have nitrogens at the 1,3 positions.. isoxazole : A monocyclic heteroarene with a structure consisting of a 5-membered ring containing three carbon atoms and an oxygen and nitrogen atom adjacent to each other. It is the parent of the class of isoxazoles.. isoxazoles : Oxazoles in which the N and O atoms are adjacent.		2.0410isoxazoles;
mancude organic heteromonocyclic parent;
monocyclic heteroarene
3-hydroxyflavone
3-hydroxyflavone: structure given in first source. flavonol : A monohydroxyflavone that is the 3-hydroxy derivative of flavone.		2.0310flavonols;
monohydroxyflavone
camptothecin
NSC 100880: carboxylate (opened lactone) form of camptothecin; RN refers to (S)-isomer; structure given in first source		2.1310delta-lactone;
pyranoindolizinoquinoline;
quinoline alkaloid;
tertiary alcohol		antineoplastic agent;
EC 5.99.1.2 (DNA topoisomerase) inhibitor;
genotoxin;
plant metabolite
silybin
silibinin : A flavonolignan isolated from milk thistle, Silybum marianum, that has been shown to exhibit antioxidant and antineoplastic activities.		2.1310aromatic ether;
benzodioxine;
flavonolignan;
polyphenol;
secondary alpha-hydroxy ketone		antineoplastic agent;
antioxidant;
hepatoprotective agent;
plant metabolite
alkenes
[no description available]		2.0510
mifepristone
Mifepristone: A progestational and glucocorticoid hormone antagonist. Its inhibition of progesterone induces bleeding during the luteal phase and in early pregnancy by releasing endogenous prostaglandins from the endometrium or decidua. As a glucocorticoid receptor antagonist, the drug has been used to treat hypercortisolism in patients with nonpituitary CUSHING SYNDROME.		2103-oxo-Delta(4) steroid;
acetylenic compound;
tertiary amino compound		abortifacient;
contraceptive drug;
hormone antagonist;
synthetic oral contraceptive
deoxyglucose
Deoxyglucose: 2-Deoxy-D-arabino-hexose. An antimetabolite of glucose with antiviral activity.. deoxyglucose : A deoxyhexose comprising glucose having at least one hydroxy group replaced by hydrogen.		2.0610
naringenin
(S)-naringenin : The (S)-enantiomer of naringenin.		210(2S)-flavan-4-one;
naringenin		expectorant;
plant metabolite
taxifolin
(+)-taxifolin : A taxifolin that has (2R,3R)-configuration.		2.4220taxifolinmetabolite
silychristin
silychristin : A flavonolignan isolated from Silybum marianum and has been shown to exhibit inhibitory activities against lipoxygenase and prostaglandin synthetase.		7.86301-benzofurans;
aromatic ether;
flavonolignan;
polyphenol;
secondary alpha-hydroxy ketone		lipoxygenase inhibitor;
metabolite;
prostaglandin antagonist;
radical scavenger
1,1-diphenyl-2-picrylhydrazyl
1,1-diphenyl-2-picrylhydrazyl: A diphenyl picrate; the ability to decolorize this stable radical indicates reactivity of tested compounds (Banda, Anal Chem 46:1772-7 1974)		2.110
silybin
[no description available]		8.1650
quercetin
[no description available]		2.99407-hydroxyflavonol;
pentahydroxyflavone		antibacterial agent;
antineoplastic agent;
antioxidant;
Aurora kinase inhibitor;
chelator;
EC 1.10.99.2 [ribosyldihydronicotinamide dehydrogenase (quinone)] inhibitor;
geroprotector;
phytoestrogen;
plant metabolite;
protein kinase inhibitor;
radical scavenger
luteolin
[no description available]		2.13103'-hydroxyflavonoid;
tetrahydroxyflavone		angiogenesis inhibitor;
anti-inflammatory agent;
antineoplastic agent;
apoptosis inducer;
c-Jun N-terminal kinase inhibitor;
EC 2.3.1.85 (fatty acid synthase) inhibitor;
immunomodulator;
nephroprotective agent;
plant metabolite;
radical scavenger;
vascular endothelial growth factor receptor antagonist
amphotericin b
Amphotericin B: Macrolide antifungal antibiotic produced by Streptomyces nodosus obtained from soil of the Orinoco river region of Venezuela.. amphotericin B : A macrolide antibiotic used to treat potentially life-threatening fungal infections.		2.1710antibiotic antifungal drug;
macrolide antibiotic;
polyene antibiotic		antiamoebic agent;
antiprotozoal drug;
bacterial metabolite
kaempferide
kaempferide: structure in first source. kaempferide : A monomethoxyflavone that is the 4'-O-methyl derivative of kaempferol.		2107-hydroxyflavonol;
monomethoxyflavone;
trihydroxyflavone		antihypertensive agent;
metabolite
l 660,711
[no description available]		2.0510quinolines
5,5',6,6'-tetrachloro-1,1',3,3'-tetraethylbenzimidazolocarbocyanine
5,5',6,6'-tetrachloro-1,1',3,3'-tetraethylbenzimidazolocarbocyanine: structure given in first source. 1,1',3,3'-tetraethyl-5,5',6,6'-tetrachloroimidacarbocyanine : The cationic form of a C3 cyanine dye having 1,3-diethyl-5,6-dichloroindoleinine units at each end.		2.0510cyanine dye;
indolium ion		fluorochrome
carbocyanines
Carbocyanines: Compounds that contain three methine groups. They are frequently used as cationic dyes used for differential staining of biological materials.		2.0510cyanine dye;
organic iodide salt		fluorochrome
isosilybin a
isosilybin A: has antineoplastic activity; structure in first source		2.1710
silidianin
[no description available]		2.2110
isosilybin
isosilybin: flavanolignan from Silybum marianum. isosilybin : A flavonolignan isolated from Silybum marianum.		2.2110
ascorbic acid
Ascorbic Acid: A six carbon compound related to glucose. It is found naturally in citrus fruits and many vegetables. Ascorbic acid is an essential nutrient in human diets, and necessary to maintain connective tissue and bone. Its biologically active form, vitamin C, functions as a reducing agent and coenzyme in several metabolic pathways. Vitamin C is considered an antioxidant.. L-ascorbic acid : The L-enantiomer of ascorbic acid and conjugate acid of L-ascorbate.. L-ascorbate : The L-enantiomer of ascorbate and conjugate base of L-ascorbic acid, arising from selective deprotonation of the 3-hydroxy group. Required for a range of essential metabolic reactions in all animals and plants.. vitamin C : Any member of a group of vitamers that belong to the chemical structural class called butenolides that exhibit biological activity against vitamin C deficiency in animals. The vitamers include L-ascorbic acid and its salt, ionized and oxidized forms.		2.0510ascorbic acid;
vitamin C		coenzyme;
cofactor;
flour treatment agent;
food antioxidant;
food colour retention agent;
geroprotector;
plant metabolite;
skin lightening agent
silybin
Silybin: The major active component of silymarin flavonoids extracted from seeds of the MILK THISTLE, Silybum marianum; it is used in the treatment of HEPATITIS; LIVER CIRRHOSIS; and CHEMICAL AND DRUG INDUCED LIVER INJURY, and has antineoplastic activity; silybins A and B are diastereomers.		4.16150
digitonin
Digitonin: A glycoside obtained from Digitalis purpurea; the aglycone is digitogenin which is bound to five sugars. Digitonin solubilizes lipids, especially in membranes and is used as a tool in cellular biochemistry, and reagent for precipitating cholesterol. It has no cardiac effects.. digitonin : A spirostanyl glycoside that is digitogenin in which the 3-hydroxy group is substituted by a beta-D-glucopyranosyl-(1->3)-beta-D-galactopyranosyl-(1->2)-[beta-D-xylopyranosyl-(1->3)]-beta-D-glucopyranosyl-(1->4)-beta-D-galactopyranosyl group. It is a steroidal saponin isolated from the foxglove plant, Digitalis purpurea. It is used extensively as a mild non-ionic detergent for extracting proteins from membranes for structure and function studies.		2.1510
allopurinol
Allopurinol: A XANTHINE OXIDASE inhibitor that decreases URIC ACID production. It also acts as an antimetabolite on some simpler organisms.. allopurinol : A bicyclic structure comprising a pyrazole ring fused to a hydroxy-substituted pyrimidine ring.		2.0510nucleobase analogue;
organic heterobicyclic compound		antimetabolite;
EC 1.17.3.2 (xanthine oxidase) inhibitor;
gout suppressant;
radical scavenger
ConditionIndicatedRelationship StrengthStudiesTrials
Acute Confusional Senile Dementia
[description not available]		02.0510
Idiopathic Parkinson Disease
[description not available]		02.0510
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)		02.0510
Parkinson Disease
A progressive, degenerative neurologic disease characterized by a TREMOR that is maximal at rest, retropulsion (i.e. a tendency to fall backwards), rigidity, stooped posture, slowness of voluntary movements, and a masklike facial expression. Pathologic features include loss of melanin containing neurons in the substantia nigra and other pigmented nuclei of the brainstem. LEWY BODIES are present in the substantia nigra and locus coeruleus but may also be found in a related condition (LEWY BODY DISEASE, DIFFUSE) characterized by dementia in combination with varying degrees of parkinsonism. (Adams et al., Principles of Neurology, 6th ed, p1059, pp1067-75)		02.0510
Cancer of Prostate
[description not available]		02.1310
Prostatic Neoplasms
Tumors or cancer of the PROSTATE.		02.1310
Black Fever
[description not available]		02.1710
Leishmaniasis, Visceral
A chronic disease caused by LEISHMANIA DONOVANI and transmitted by the bite of several sandflies of the genera Phlebotomus and Lutzomyia. It is commonly characterized by fever, chills, vomiting, anemia, hepatosplenomegaly, leukopenia, hypergammaglobulinemia, emaciation, and an earth-gray color of the skin. The disease is classified into three main types according to geographic distribution: Indian, Mediterranean (or infantile), and African.		02.1710
Cardiovascular Stroke
[description not available]		02.2110
Injury, Ischemia-Reperfusion
[description not available]		02.2110
Myocardial Infarction
NECROSIS of the MYOCARDIUM caused by an obstruction of the blood supply to the heart (CORONARY CIRCULATION).		02.2110
Reperfusion Injury
Adverse functional, metabolic, or structural changes in tissues that result from the restoration of blood flow to the tissue (REPERFUSION) following ISCHEMIA.		02.2110
Anoxemia
[description not available]		02.1710
Hypoxia
Sub-optimal OXYGEN levels in the ambient air of living organisms.		02.1710
Hepatocellular Carcinoma
[description not available]		02.0310
Cancer of Liver
[description not available]		02.0310
Carcinoma, Hepatocellular
A primary malignant neoplasm of epithelial liver cells. It ranges from a well-differentiated tumor with EPITHELIAL CELLS indistinguishable from normal HEPATOCYTES to a poorly differentiated neoplasm. The cells may be uniform or markedly pleomorphic, or form GIANT CELLS. Several classification schemes have been suggested.		02.0310
Liver Neoplasms
Tumors or cancer of the LIVER.		02.0310