Page last updated: 2024-12-11

tazettine

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

Description

tazettine: from Amaryllidaceae [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

FloraRankFlora DefinitionFamilyFamily Definition
AmaryllidaceaefamilyA family of herbaceous plants with bulbs or rhizomes in the order Asparagales.[MeSH]AmaryllidaceaeA family of herbaceous plants with bulbs or rhizomes in the order Asparagales.[MeSH]

Cross-References

ID SourceID
PubMed CID5321780
CHEMBL ID457605
CHEBI ID32185
SCHEMBL ID5792215
MeSH IDM0057610

Synonyms (30)

Synonym
CHEBI:32185 ,
(+)-tazettine
nsc-652297
sekisanolin
nsc-115495
ungernin
sekisanin
ungernine
507-79-9
tazettin
tazettine
tazetine
sekisanoline
CHEMBL457605
unii-76weu12cso
nsc 115495
nsc 652297
76weu12cso ,
SCHEMBL5792215
sekisanine
tazettine [mi]
8h-(1,3)dioxolo(6,7)(2)benzopyrano(3,4-c)indol-6a(3h)-ol, 4,4a,5,6-tetrahydro-3-methoxy-5-methyl-, (3s,4as,6as,13bs)-
tacettine
AKOS030491273
Q27114811
(1s,13s,16s,18s)-18-methoxy-15-methyl-5,7,12-trioxa-15-azapentacyclo[11.7.0.01,16.02,10.04,8]icosa-2,4(8),9,19-tetraen-13-ol
(+)-(3s,4as,6as,13bs)-3-methoxy-5-methyl-4,4a,5,6-tetrahydro-3h,8h-[1,3]dioxolo[ 6,7][2]benzopyrano[3,4-c]indol-6a-ol
DTXSID10878333
STL578169
bdbm50546237

Research Excerpts

Overview

Tazettine is a common Amaryllidaceac alkaloid. It could be used as a model substance for the further development of either analogues or related compounds with better inhibition potency.

ExcerptReferenceRelevance
"Tazettine is a common Amaryllidaceac alkaloid, which could be used as a model substance for the further development of either analogues or related compounds with better inhibition potency."( AKR1C3 Inhibitory Potency of Naturally-occurring Amaryllidaceae Alkaloids of Different Structural Types.
Breiterová, K; Cahliková, L; Hošt'fálková, A; Hulcová, D; Šafratová, M; Siatkac, T; Vaněčková, N; Wsól, V; Zemanová, L, 2017
)
1.18
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (2)

ClassDescription
indole alkaloid fundamental parent
indole alkaloidAn alkaloid containing an indole skeleton.
[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)
Aldo-keto reductase family 1 member C3Homo sapiens (human)IC50 (µMol)15.80000.05002.207010.0000AID1674103
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (30)

Processvia Protein(s)Taxonomy
retinoid metabolic processAldo-keto reductase family 1 member C3Homo sapiens (human)
prostaglandin metabolic processAldo-keto reductase family 1 member C3Homo sapiens (human)
G protein-coupled receptor signaling pathwayAldo-keto reductase family 1 member C3Homo sapiens (human)
response to nutrientAldo-keto reductase family 1 member C3Homo sapiens (human)
steroid metabolic processAldo-keto reductase family 1 member C3Homo sapiens (human)
positive regulation of cell population proliferationAldo-keto reductase family 1 member C3Homo sapiens (human)
male gonad developmentAldo-keto reductase family 1 member C3Homo sapiens (human)
cellular response to starvationAldo-keto reductase family 1 member C3Homo sapiens (human)
farnesol catabolic processAldo-keto reductase family 1 member C3Homo sapiens (human)
cyclooxygenase pathwayAldo-keto reductase family 1 member C3Homo sapiens (human)
keratinocyte differentiationAldo-keto reductase family 1 member C3Homo sapiens (human)
progesterone metabolic processAldo-keto reductase family 1 member C3Homo sapiens (human)
retinol metabolic processAldo-keto reductase family 1 member C3Homo sapiens (human)
retinal metabolic processAldo-keto reductase family 1 member C3Homo sapiens (human)
macromolecule metabolic processAldo-keto reductase family 1 member C3Homo sapiens (human)
daunorubicin metabolic processAldo-keto reductase family 1 member C3Homo sapiens (human)
doxorubicin metabolic processAldo-keto reductase family 1 member C3Homo sapiens (human)
regulation of retinoic acid receptor signaling pathwayAldo-keto reductase family 1 member C3Homo sapiens (human)
positive regulation of phosphatidylinositol 3-kinase/protein kinase B signal transductionAldo-keto reductase family 1 member C3Homo sapiens (human)
testosterone biosynthetic processAldo-keto reductase family 1 member C3Homo sapiens (human)
renal absorptionAldo-keto reductase family 1 member C3Homo sapiens (human)
cellular response to calcium ionAldo-keto reductase family 1 member C3Homo sapiens (human)
cellular response to prostaglandin stimulusAldo-keto reductase family 1 member C3Homo sapiens (human)
cellular response to corticosteroid stimulusAldo-keto reductase family 1 member C3Homo sapiens (human)
cellular response to jasmonic acid stimulusAldo-keto reductase family 1 member C3Homo sapiens (human)
cellular response to prostaglandin D stimulusAldo-keto reductase family 1 member C3Homo sapiens (human)
negative regulation of retinoic acid biosynthetic processAldo-keto reductase family 1 member C3Homo sapiens (human)
regulation of testosterone biosynthetic processAldo-keto reductase family 1 member C3Homo sapiens (human)
positive regulation of endothelial cell apoptotic processAldo-keto reductase family 1 member C3Homo sapiens (human)
positive regulation of reactive oxygen species metabolic processAldo-keto reductase family 1 member C3Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (23)

Processvia Protein(s)Taxonomy
retinal dehydrogenase activityAldo-keto reductase family 1 member C3Homo sapiens (human)
aldose reductase (NADPH) activityAldo-keto reductase family 1 member C3Homo sapiens (human)
aldo-keto reductase (NADPH) activityAldo-keto reductase family 1 member C3Homo sapiens (human)
estradiol 17-beta-dehydrogenase [NAD(P)] activityAldo-keto reductase family 1 member C3Homo sapiens (human)
all-trans-retinol dehydrogenase (NAD+) activityAldo-keto reductase family 1 member C3Homo sapiens (human)
oxidoreductase activity, acting on NAD(P)H, quinone or similar compound as acceptorAldo-keto reductase family 1 member C3Homo sapiens (human)
phenanthrene 9,10-monooxygenase activityAldo-keto reductase family 1 member C3Homo sapiens (human)
dihydrotestosterone 17-beta-dehydrogenase activityAldo-keto reductase family 1 member C3Homo sapiens (human)
prostaglandin H2 endoperoxidase reductase activityAldo-keto reductase family 1 member C3Homo sapiens (human)
prostaglandin D2 11-ketoreductase activityAldo-keto reductase family 1 member C3Homo sapiens (human)
geranylgeranyl reductase activityAldo-keto reductase family 1 member C3Homo sapiens (human)
ketoreductase activityAldo-keto reductase family 1 member C3Homo sapiens (human)
prostaglandin-F synthase activityAldo-keto reductase family 1 member C3Homo sapiens (human)
15-hydroxyprostaglandin-D dehydrogenase (NADP+) activityAldo-keto reductase family 1 member C3Homo sapiens (human)
androsterone dehydrogenase activityAldo-keto reductase family 1 member C3Homo sapiens (human)
5alpha-androstane-3beta,17beta-diol dehydrogenase activityAldo-keto reductase family 1 member C3Homo sapiens (human)
testosterone dehydrogenase (NAD+) activityAldo-keto reductase family 1 member C3Homo sapiens (human)
androstan-3-alpha,17-beta-diol dehydrogenase activityAldo-keto reductase family 1 member C3Homo sapiens (human)
testosterone 17-beta-dehydrogenase (NADP+) activityAldo-keto reductase family 1 member C3Homo sapiens (human)
ketosteroid monooxygenase activityAldo-keto reductase family 1 member C3Homo sapiens (human)
Delta4-3-oxosteroid 5beta-reductase activityAldo-keto reductase family 1 member C3Homo sapiens (human)
all-trans-retinol dehydrogenase (NADP+) activityAldo-keto reductase family 1 member C3Homo sapiens (human)
bile acid bindingAldo-keto reductase family 1 member C3Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (4)

Processvia Protein(s)Taxonomy
nucleusAldo-keto reductase family 1 member C3Homo sapiens (human)
cytoplasmAldo-keto reductase family 1 member C3Homo sapiens (human)
cytosolAldo-keto reductase family 1 member C3Homo sapiens (human)
extracellular exosomeAldo-keto reductase family 1 member C3Homo sapiens (human)
cytosolAldo-keto reductase family 1 member C3Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (26)

Assay IDTitleYearJournalArticle
AID718094Cytotoxicity against human HL60 cells after 48 hrs by MTT assay2012Journal of natural products, Dec-28, Volume: 75, Issue:12
Cytotoxic alkaloids from the whole plants of Zephyranthes candida.
AID335099Cytotoxicity against human ZR-75-1 cells after 3 days by sulforhodamine B assay1993Journal of natural products, Aug, Volume: 56, Issue:8
Cytotoxicity of Hymenocallis expansa alkaloids.
AID491982Cytotoxicity against human SK-MEL cells after 72 hrs by MTT colorimetric assay2010Journal of natural products, Jul-23, Volume: 73, Issue:7
Amaryllidaceae alkaloids belonging to different structural subgroups display activity against apoptosis-resistant cancer cells.
AID501441Inhibition of AChE at 10 uM by Ellman's assay2010Bioorganic & medicinal chemistry letters, Sep-01, Volume: 20, Issue:17
Structure-activity studies on acetylcholinesterase inhibition in the lycorine series of Amaryllidaceae alkaloids.
AID335090Cytotoxicity against human A431 cells after 3 days by sulforhodamine B assay1993Journal of natural products, Aug, Volume: 56, Issue:8
Cytotoxicity of Hymenocallis expansa alkaloids.
AID335091Cytotoxicity against human BC1 cells after 3 days by sulforhodamine B assay1993Journal of natural products, Aug, Volume: 56, Issue:8
Cytotoxicity of Hymenocallis expansa alkaloids.
AID335097Cytotoxicity against human Lu1 cells after 3 days by sulforhodamine B assay1993Journal of natural products, Aug, Volume: 56, Issue:8
Cytotoxicity of Hymenocallis expansa alkaloids.
AID335095Cytotoxicity against human KBV1 cells after 3 days by sulforhodamine B assay1993Journal of natural products, Aug, Volume: 56, Issue:8
Cytotoxicity of Hymenocallis expansa alkaloids.
AID491981Cytotoxicity against human U373 cells after 72 hrs by MTT colorimetric assay2010Journal of natural products, Jul-23, Volume: 73, Issue:7
Amaryllidaceae alkaloids belonging to different structural subgroups display activity against apoptosis-resistant cancer cells.
AID335094Cytotoxicity against human KB cells after 3 days by sulforhodamine B assay1993Journal of natural products, Aug, Volume: 56, Issue:8
Cytotoxicity of Hymenocallis expansa alkaloids.
AID491983Cytotoxicity against mouse B16F10 cells after 72 hrs by MTT colorimetric assay2010Journal of natural products, Jul-23, Volume: 73, Issue:7
Amaryllidaceae alkaloids belonging to different structural subgroups display activity against apoptosis-resistant cancer cells.
AID1674103Inhibition of human AKR1C3 expressed in Escherichia coli preincubated for 15 mins followed by Adion addition and measured after 30 mins by HPLC analysis2020Journal of medicinal chemistry, 10-22, Volume: 63, Issue:20
Overview of AKR1C3: Inhibitor Achievements and Disease Insights.
AID335093Cytotoxicity against human HT cells after 3 days by sulforhodamine B assay1993Journal of natural products, Aug, Volume: 56, Issue:8
Cytotoxicity of Hymenocallis expansa alkaloids.
AID335092Cytotoxicity against human Col2 cells after 3 days by sulforhodamine B assay1993Journal of natural products, Aug, Volume: 56, Issue:8
Cytotoxicity of Hymenocallis expansa alkaloids.
AID335098Cytotoxicity against human SK-MEL-2 cells after 3 days by sulforhodamine B assay1993Journal of natural products, Aug, Volume: 56, Issue:8
Cytotoxicity of Hymenocallis expansa alkaloids.
AID1578099Antiplasmodial activity against Trichomonas vaginalis assessed as reduction in plasmodium viability at 125 ug/ml relative to control2019Bioorganic & medicinal chemistry letters, 10-15, Volume: 29, Issue:20
Antiprotozoal alkaloid principles of the plant family Amaryllidaceae.
AID718093Cytotoxicity against human K562 cells after 48 hrs by MTT assay2012Journal of natural products, Dec-28, Volume: 75, Issue:12
Cytotoxic alkaloids from the whole plants of Zephyranthes candida.
AID492427Antimalarial activity against Plasmodium falciparum K12009Bioorganic & medicinal chemistry, May-01, Volume: 17, Issue:9
Antimalarials from nature.
AID718092Cytotoxicity against human HepG2 cells after 48 hrs by MTT assay2012Journal of natural products, Dec-28, Volume: 75, Issue:12
Cytotoxic alkaloids from the whole plants of Zephyranthes candida.
AID718090Cytotoxicity against human HT-29 cells after 48 hrs by MTT assay2012Journal of natural products, Dec-28, Volume: 75, Issue:12
Cytotoxic alkaloids from the whole plants of Zephyranthes candida.
AID335096Cytotoxicity against human LNCAP cells after 3 days by sulforhodamine B assay1993Journal of natural products, Aug, Volume: 56, Issue:8
Cytotoxicity of Hymenocallis expansa alkaloids.
AID491980Cytotoxicity against human Hs683 cells after 72 hrs by MTT colorimetric assay2010Journal of natural products, Jul-23, Volume: 73, Issue:7
Amaryllidaceae alkaloids belonging to different structural subgroups display activity against apoptosis-resistant cancer cells.
AID718091Cytotoxicity against human A549 cells after 48 hrs by MTT assay2012Journal of natural products, Dec-28, Volume: 75, Issue:12
Cytotoxic alkaloids from the whole plants of Zephyranthes candida.
AID335100Cytotoxicity against mouse P388 cells after 3 days by sulforhodamine B assay1993Journal of natural products, Aug, Volume: 56, Issue:8
Cytotoxicity of Hymenocallis expansa alkaloids.
AID491979Cytotoxicity against human OE21 cells after 72 hrs by MTT colorimetric assay2010Journal of natural products, Jul-23, Volume: 73, Issue:7
Amaryllidaceae alkaloids belonging to different structural subgroups display activity against apoptosis-resistant cancer cells.
AID491978Cytotoxicity against human A549 cells after 72 hrs by MTT colorimetric assay2010Journal of natural products, Jul-23, Volume: 73, Issue:7
Amaryllidaceae alkaloids belonging to different structural subgroups display activity against apoptosis-resistant cancer cells.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (23)

TimeframeStudies, This Drug (%)All Drugs %
pre-19905 (21.74)18.7374
1990's1 (4.35)18.2507
2000's4 (17.39)29.6817
2010's11 (47.83)24.3611
2020's2 (8.70)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 22.21

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 moderate demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index22.21 (24.57)
Research Supply Index3.22 (2.92)
Research Growth Index4.85 (4.65)
Search Engine Demand Index21.17 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (22.21)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews3 (12.50%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other21 (87.50%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]