Page last updated: 2024-12-10

gentiacaulein

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

Description

gentiacaulein: structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

gentiacaulein : A member of the class of xanthones that is 9H-xanthen-9-one substituted by hydroxy groups at positions 2 and 8 and methoxy groups at positions 1 and 6. [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]

Cross-References

ID SourceID
PubMed CID5281634
CHEMBL ID467590
CHEBI ID5313
MeSH IDM0456490

Synonyms (22)

Synonym
2,8-dihydroxy-1,6-dimethoxy-xanthen-9-one
2,8-dihydroxy-1,6-dimethoxy-9h-xanthen-9-one
2,6-dimethoxyxanthone
nsc-661743
nsc661743
MLS000563494 ,
smr000232301
15402-27-4
gentiacaulein
2,8-dihydroxy-1,6-dimethoxyxanthone
CHEMBL467590
getiacaulein
chebi:5313 ,
2,8-dihydroxy-1,6-dimethoxyxanthen-9-one
AC1NQYS1 ,
HMS2227I16
HMS3338N03
DTXSID10415161
bdbm174835
us9114126, 2027ba1
1,7-dihydroxy-3,8-dimethoxyxanthone
Q27106712
[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 (3)

ClassDescription
xanthonesAny member of the class of xanthenes based on a xanthone skeleton.
polyphenolMembers of the class of phenols that contain 2 or more benzene rings each of which is substituted by at least one hydroxy group.
aromatic etherAny 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 (16)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Chain A, 2-oxoglutarate OxygenaseHomo sapiens (human)Potency28.18380.177814.390939.8107AID2147
LuciferasePhotinus pyralis (common eastern firefly)Potency19.01150.007215.758889.3584AID588342
glp-1 receptor, partialHomo sapiens (human)Potency14.12540.01846.806014.1254AID624417
ATAD5 protein, partialHomo sapiens (human)Potency20.73290.004110.890331.5287AID504466; AID504467
USP1 protein, partialHomo sapiens (human)Potency8.91250.031637.5844354.8130AID743255
TDP1 proteinHomo sapiens (human)Potency22.72650.000811.382244.6684AID686978; AID686979
Microtubule-associated protein tauHomo sapiens (human)Potency12.58930.180013.557439.8107AID1460
aldehyde dehydrogenase 1 family, member A1Homo sapiens (human)Potency22.38720.011212.4002100.0000AID1030
P53Homo sapiens (human)Potency50.11870.07319.685831.6228AID504706
euchromatic histone-lysine N-methyltransferase 2Homo sapiens (human)Potency79.43280.035520.977089.1251AID504332
15-hydroxyprostaglandin dehydrogenase [NAD(+)] isoform 1Homo sapiens (human)Potency14.12540.001815.663839.8107AID894
nuclear factor erythroid 2-related factor 2 isoform 2Homo sapiens (human)Potency29.09290.00419.984825.9290AID504444
nuclear receptor ROR-gamma isoform 1Mus musculus (house mouse)Potency12.58930.00798.23321,122.0200AID2551
VprHuman immunodeficiency virus 1Potency63.09571.584919.626463.0957AID651644
lamin isoform A-delta10Homo sapiens (human)Potency15.84890.891312.067628.1838AID1487
TAR DNA-binding protein 43Homo sapiens (human)Potency2.81841.778316.208135.4813AID652104
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (18)

Processvia Protein(s)Taxonomy
negative regulation of protein phosphorylationTAR DNA-binding protein 43Homo sapiens (human)
mRNA processingTAR DNA-binding protein 43Homo sapiens (human)
RNA splicingTAR DNA-binding protein 43Homo sapiens (human)
negative regulation of gene expressionTAR DNA-binding protein 43Homo sapiens (human)
regulation of protein stabilityTAR DNA-binding protein 43Homo sapiens (human)
positive regulation of insulin secretionTAR DNA-binding protein 43Homo sapiens (human)
response to endoplasmic reticulum stressTAR DNA-binding protein 43Homo sapiens (human)
positive regulation of protein import into nucleusTAR DNA-binding protein 43Homo sapiens (human)
regulation of circadian rhythmTAR DNA-binding protein 43Homo sapiens (human)
regulation of apoptotic processTAR DNA-binding protein 43Homo sapiens (human)
negative regulation by host of viral transcriptionTAR DNA-binding protein 43Homo sapiens (human)
rhythmic processTAR DNA-binding protein 43Homo sapiens (human)
regulation of cell cycleTAR DNA-binding protein 43Homo sapiens (human)
3'-UTR-mediated mRNA destabilizationTAR DNA-binding protein 43Homo sapiens (human)
3'-UTR-mediated mRNA stabilizationTAR DNA-binding protein 43Homo sapiens (human)
nuclear inner membrane organizationTAR DNA-binding protein 43Homo sapiens (human)
amyloid fibril formationTAR DNA-binding protein 43Homo sapiens (human)
regulation of gene expressionTAR DNA-binding protein 43Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (10)

Processvia Protein(s)Taxonomy
RNA polymerase II cis-regulatory region sequence-specific DNA bindingTAR DNA-binding protein 43Homo sapiens (human)
DNA bindingTAR DNA-binding protein 43Homo sapiens (human)
double-stranded DNA bindingTAR DNA-binding protein 43Homo sapiens (human)
RNA bindingTAR DNA-binding protein 43Homo sapiens (human)
mRNA 3'-UTR bindingTAR DNA-binding protein 43Homo sapiens (human)
protein bindingTAR DNA-binding protein 43Homo sapiens (human)
lipid bindingTAR DNA-binding protein 43Homo sapiens (human)
identical protein bindingTAR DNA-binding protein 43Homo sapiens (human)
pre-mRNA intronic bindingTAR DNA-binding protein 43Homo sapiens (human)
molecular condensate scaffold activityTAR DNA-binding protein 43Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (9)

Processvia Protein(s)Taxonomy
intracellular non-membrane-bounded organelleTAR DNA-binding protein 43Homo sapiens (human)
nucleusTAR DNA-binding protein 43Homo sapiens (human)
nucleoplasmTAR DNA-binding protein 43Homo sapiens (human)
perichromatin fibrilsTAR DNA-binding protein 43Homo sapiens (human)
mitochondrionTAR DNA-binding protein 43Homo sapiens (human)
cytoplasmic stress granuleTAR DNA-binding protein 43Homo sapiens (human)
nuclear speckTAR DNA-binding protein 43Homo sapiens (human)
interchromatin granuleTAR DNA-binding protein 43Homo sapiens (human)
nucleoplasmTAR DNA-binding protein 43Homo sapiens (human)
chromatinTAR DNA-binding protein 43Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (42)

Assay IDTitleYearJournalArticle
AID588499High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set2010Current protocols in cytometry, Oct, Volume: Chapter 13Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588499High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set2006Cytometry. 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.
AID588499High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set2010Assay and drug development technologies, Feb, Volume: 8, Issue:1
High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors.
AID588501High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set2010Current protocols in cytometry, Oct, Volume: Chapter 13Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588501High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set2006Cytometry. 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.
AID588501High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set2010Assay and drug development technologies, Feb, Volume: 8, Issue:1
High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors.
AID1347083qHTS for Inhibitors of the Functional Ribonucleoprotein Complex (vRNP) of Lassa (LASV) Arenavirus: Viability assay - alamar blue signal for LASV Primary Screen2020Antiviral research, 01, Volume: 173A cell-based, infectious-free, platform to identify inhibitors of lassa virus ribonucleoprotein (vRNP) activity.
AID651635Viability Counterscreen for Primary qHTS for Inhibitors of ATXN expression
AID1347086qHTS for Inhibitors of the Functional Ribonucleoprotein Complex (vRNP) of Lymphocytic Choriomeningitis Arenaviruses (LCMV): LCMV Primary Screen - GLuc reporter signal2020Antiviral research, 01, Volume: 173A cell-based, infectious-free, platform to identify inhibitors of lassa virus ribonucleoprotein (vRNP) activity.
AID1347082qHTS for Inhibitors of the Functional Ribonucleoprotein Complex (vRNP) of Lassa (LASV) Arenavirus: LASV Primary Screen - GLuc reporter signal2020Antiviral research, 01, Volume: 173A cell-based, infectious-free, platform to identify inhibitors of lassa virus ribonucleoprotein (vRNP) activity.
AID504812Inverse Agonists of the Thyroid Stimulating Hormone Receptor: HTS campaign2010Endocrinology, Jul, Volume: 151, Issue:7
A small molecule inverse agonist for the human thyroid-stimulating hormone receptor.
AID504810Antagonists of the Thyroid Stimulating Hormone Receptor: HTS campaign2010Endocrinology, Jul, Volume: 151, Issue:7
A small molecule inverse agonist for the human thyroid-stimulating hormone receptor.
AID588497High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set2010Current protocols in cytometry, Oct, Volume: Chapter 13Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588497High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set2006Cytometry. 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.
AID588497High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set2010Assay and drug development technologies, Feb, Volume: 8, Issue:1
High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors.
AID1745845Primary qHTS for Inhibitors of ATXN expression
AID384219Antiproliferative activity against human U251 cells assessed as mitochondrial dehydrogenase activity after 24 hrs by MTT assay2008Bioorganic & medicinal chemistry, May-15, Volume: 16, Issue:10
Antiglioma action of xanthones from Gentiana kochiana: Mechanistic and structure-activity requirements.
AID384240Antiproliferative activity against Albino Oxford rat peritoneal macrophages assessed as mitochondrial respiration after 48 hrs by MTT assay2008Bioorganic & medicinal chemistry, May-15, Volume: 16, Issue:10
Antiglioma action of xanthones from Gentiana kochiana: Mechanistic and structure-activity requirements.
AID384217Antiproliferative activity against rat C6 cells assessed as cell number after 24 hrs by crystal violet assay2008Bioorganic & medicinal chemistry, May-15, Volume: 16, Issue:10
Antiglioma action of xanthones from Gentiana kochiana: Mechanistic and structure-activity requirements.
AID384231Induction apoptosis in rat C6 cells assessed as caspase activation at 50 uM after 36 hrs by flow cytometry relative to control2008Bioorganic & medicinal chemistry, May-15, Volume: 16, Issue:10
Antiglioma action of xanthones from Gentiana kochiana: Mechanistic and structure-activity requirements.
AID384239Antiproliferative activity against Albino Oxford rat peritoneal macrophages assessed as cell number after 48 hrs by crystal violet assay2008Bioorganic & medicinal chemistry, May-15, Volume: 16, Issue:10
Antiglioma action of xanthones from Gentiana kochiana: Mechanistic and structure-activity requirements.
AID384222Antiproliferative activity against rat C6 cells assessed as mitochondrial dehydrogenase activity after 72 hrs by MTT assay2008Bioorganic & medicinal chemistry, May-15, Volume: 16, Issue:10
Antiglioma action of xanthones from Gentiana kochiana: Mechanistic and structure-activity requirements.
AID384225Cell cycle arrest in rat C6 cells assessed as accumulation at S phase at 50 uM after 24 hrs by flow cytometry relative to control2008Bioorganic & medicinal chemistry, May-15, Volume: 16, Issue:10
Antiglioma action of xanthones from Gentiana kochiana: Mechanistic and structure-activity requirements.
AID384235Antiproliferative activity against rat C6 cells assessed as cell number after 48 hrs by crystal violet assay in presence of N-acetyl-cysteine2008Bioorganic & medicinal chemistry, May-15, Volume: 16, Issue:10
Antiglioma action of xanthones from Gentiana kochiana: Mechanistic and structure-activity requirements.
AID384221Antiproliferative activity against human U251 cells assessed as cell number after 72 hrs by crystal violet assay2008Bioorganic & medicinal chemistry, May-15, Volume: 16, Issue:10
Antiglioma action of xanthones from Gentiana kochiana: Mechanistic and structure-activity requirements.
AID384214Antiproliferative activity against human U251 cells assessed as cell number after 24 hrs by crystal violet assay2008Bioorganic & medicinal chemistry, May-15, Volume: 16, Issue:10
Antiglioma action of xanthones from Gentiana kochiana: Mechanistic and structure-activity requirements.
AID384226Cell cycle arrest in rat C6 cells assessed as accumulation at G2/M phase at 50 uM after 24 hrs by flow cytometry relative to control2008Bioorganic & medicinal chemistry, May-15, Volume: 16, Issue:10
Antiglioma action of xanthones from Gentiana kochiana: Mechanistic and structure-activity requirements.
AID384223Antiproliferative activity against human U251 cells assessed as mitochondrial dehydrogenase activity after 72 hrs by MTT assay2008Bioorganic & medicinal chemistry, May-15, Volume: 16, Issue:10
Antiglioma action of xanthones from Gentiana kochiana: Mechanistic and structure-activity requirements.
AID384227Inhibition of bovine brain tubulin by microtubule depolymerization assay2008Bioorganic & medicinal chemistry, May-15, Volume: 16, Issue:10
Antiglioma action of xanthones from Gentiana kochiana: Mechanistic and structure-activity requirements.
AID384234Antiproliferative activity against rat C6 cells assessed as caspase activation at 50 uM after 36 hrs by flow cytometry in presence of N-acetyl-cysteine2008Bioorganic & medicinal chemistry, May-15, Volume: 16, Issue:10
Antiglioma action of xanthones from Gentiana kochiana: Mechanistic and structure-activity requirements.
AID384232Induction of mitochondrial membrane potential depolarization in rat C6 cells assessed as increase in green to red fluorescence ratio at 50 uM after 24 hrs by flow cytometry2008Bioorganic & medicinal chemistry, May-15, Volume: 16, Issue:10
Antiglioma action of xanthones from Gentiana kochiana: Mechanistic and structure-activity requirements.
AID384237Antiproliferative activity against Albino Oxford rat primary astrocytes assessed as mitochondrial respiration after 48 hrs by MTT assay2008Bioorganic & medicinal chemistry, May-15, Volume: 16, Issue:10
Antiglioma action of xanthones from Gentiana kochiana: Mechanistic and structure-activity requirements.
AID384224Cell cycle arrest in rat C6 cells assessed as accumulation at G0/G1 phase at 50 uM after 24 hrs by flow cytometry relative to control2008Bioorganic & medicinal chemistry, May-15, Volume: 16, Issue:10
Antiglioma action of xanthones from Gentiana kochiana: Mechanistic and structure-activity requirements.
AID384238Antiproliferative activity against Albino Oxford rat primary astrocytes assessed as change in morphology by bright field microscopy2008Bioorganic & medicinal chemistry, May-15, Volume: 16, Issue:10
Antiglioma action of xanthones from Gentiana kochiana: Mechanistic and structure-activity requirements.
AID384218Antiproliferative activity against rat C6 cells assessed as mitochondrial dehydrogenase activity after 24 hrs by MTT assay2008Bioorganic & medicinal chemistry, May-15, Volume: 16, Issue:10
Antiglioma action of xanthones from Gentiana kochiana: Mechanistic and structure-activity requirements.
AID384236Antiproliferative activity against Albino Oxford rat primary astrocytes assessed as cell number after 48 hrs by crystal violet assay2008Bioorganic & medicinal chemistry, May-15, Volume: 16, Issue:10
Antiglioma action of xanthones from Gentiana kochiana: Mechanistic and structure-activity requirements.
AID384230Induction apoptosis in rat C6 cells at 50 uM after 36 hrs by flow cytometry relative to control2008Bioorganic & medicinal chemistry, May-15, Volume: 16, Issue:10
Antiglioma action of xanthones from Gentiana kochiana: Mechanistic and structure-activity requirements.
AID384216Antiproliferative activity against human U251 cells assessed as cell number after 48 hrs by crystal violet assay2008Bioorganic & medicinal chemistry, May-15, Volume: 16, Issue:10
Antiglioma action of xanthones from Gentiana kochiana: Mechanistic and structure-activity requirements.
AID384215Antiproliferative activity against rat C6 cells assessed as cell number after 48 hrs by crystal violet assay2008Bioorganic & medicinal chemistry, May-15, Volume: 16, Issue:10
Antiglioma action of xanthones from Gentiana kochiana: Mechanistic and structure-activity requirements.
AID384220Antiproliferative activity against rat C6 cells assessed as cell number after 72 hrs by crystal violet assay2008Bioorganic & medicinal chemistry, May-15, Volume: 16, Issue:10
Antiglioma action of xanthones from Gentiana kochiana: Mechanistic and structure-activity requirements.
AID384233Induction of reactive oxygen species production in rat C6 cells at 50 uM after 36 hrs by flow cytometry2008Bioorganic & medicinal chemistry, May-15, Volume: 16, Issue:10
Antiglioma action of xanthones from Gentiana kochiana: Mechanistic and structure-activity requirements.
AID384229Induction necrosis in rat C6 cells at 50 uM after 36 hrs by flow cytometry relative to control2008Bioorganic & medicinal chemistry, May-15, Volume: 16, Issue:10
Antiglioma action of xanthones from Gentiana kochiana: Mechanistic and structure-activity requirements.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (13)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's5 (38.46)29.6817
2010's6 (46.15)24.3611
2020's2 (15.38)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

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%
Other13 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]