Page last updated: 2024-12-07

daphnetoxin

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

Description

daphnetoxin: RN given for (2S-(2alpha,3abeta,3bbeta,3cbeta,4abeta,5beta,5abeta,8aalpha,8balpha,9alpha,10abeta))-isomer; a PKCalpha activator; isolated from the bark of Daphne gnidium; structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

daphnetoxin : A daphnane-type orthoester diterpene with potential cholesterol-lowering activity, found exclusively in plants of the family Thymelaeaceae. [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
DaphnegenusA plant genus of the family THYMELAEACEAE. They are evergreen shrubs much cultivated in garden borders and rock gardens in mild climates. Members contain mezerein, flavonoids, and COUMARINS such as daphnetin and daphnin.[MeSH]ThymelaeaceaeA plant family of the order Myrtales, subclass Rosidae, class Magnoliopsida. They are mainly trees and shrubs. Many members contain mucilage and COUMARINS.[MeSH]

Cross-References

ID SourceID
PubMed CID119454
CHEMBL ID2023369
CHEBI ID4321
MeSH IDM0421733

Synonyms (8)

Synonym
6h-2,8b-epoxyoxireno(6,7)azuleno(5,4-e)-1,3-benzodioxol-6-one, 3a,3b,3c,4a,5,5a,8a,9,10,10a-decahydro-5,5a-dihydroxy-4a-(hydroxymethyl)-7,9-dimethyl-10a-(1-methylethenyl)-2-phenyl-, (2s,3ar,3bs,3cs,4ar,5s,5as,8ar,9r,10ar)-
daphnetoxin
(2s,3ar,3bs,3cs,4ar,5s,5as,8ar,8br,9r,10ar)-5,5a-dihydroxy-4a-(hydroxymethyl)-10a-isopropenyl-7,9-dimethyl-2-phenyl-3a,3b,3c,4a,5,5a,8a,9,10,10a-decahydro-6h-2,8b-epoxyoxireno[6,7]azuleno[5,4-e][1,3]benzodioxol-6-one
(2s)-3abeta,3bbeta,3cbeta,4a,5,5a,8aalpha,9,10,10a-decahydro-5beta,5abeta-dihydroxy-4abeta-hydroxymethyl-7,9alpha-dimethyl-10abeta-(1-methylethenyl)-2-phenyl-6h-2,8balpha-epoxyoxireno[6,7]azuleno[5,4-e]-1,3-benzodioxol-6-one
CHEBI:4321 ,
A5463
CHEMBL2023369
Q27106336

Research Excerpts

Overview

Daphnetoxin is a daphnane type orthoester diterpene found exclusively in plants of the family Thymelaeaceae. Daphnoretin is a bis-coumarin derivative that is the major constituent of the bark of some plants of this family.

ExcerptReferenceRelevance
"Daphnetoxin is a daphnane type orthoester diterpene found exclusively in plants of the family Thymelaeaceae while daphnoretin, a bis-coumarin derivative that is the major constituent of the bark of some plants of this family, can also be found in Leguminosae and Rutaceae. "( Mitochondrial toxicity of the phyotochemicals daphnetoxin and daphnoretin--relevance for possible anti-cancer application.
Barbosa, IA; Burgeiro, A; Carvalho, MJ; Diogo, CV; Félix, L; Oliveira, PJ; Peixoto, FP; Vilela, S, 2009
)
2.05

Toxicity

ExcerptReferenceRelevance
" The results indicate that both test compounds are toxic to isolated mitochondrial fractions, especially when used at concentrations higher than 100 microM."( Mitochondrial toxicity of the phyotochemicals daphnetoxin and daphnoretin--relevance for possible anti-cancer application.
Barbosa, IA; Burgeiro, A; Carvalho, MJ; Diogo, CV; Félix, L; Oliveira, PJ; Peixoto, FP; Vilela, S, 2009
)
0.61
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (4)

ClassDescription
diterpene alkaloid
ortho esterAny organooxygen compound that has the general formula RC(OR(1))(OR(2))(OR(3)), where R(1), R(2), R(3) =/= H.
epoxideAny cyclic ether in which the oxygen atom forms part of a 3-membered ring.
tertiary alpha-hydroxy ketoneAn alpha-hydroxy ketone in which the carbonyl group and the hydroxy group are linked by a carbon bearing two organyl groups.
[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 (12)

Assay IDTitleYearJournalArticle
AID658567Resistance factor, ratio of EC50 for multidrug-resistant HIV1 106-PR infected in HEK293T cells to wildtype HIV1 infected in HEK293T cells2012Journal of natural products, Mar-23, Volume: 75, Issue:3
Library-based discovery and characterization of daphnane diterpenes as potent and selective HIV inhibitors in Daphne gnidium.
AID658570Upregulation of CD69 expression in PHA- and IL-2-stimulated human PBMC membranes at 20 nM after 48 hrs by flow cytometric analysis2012Journal of natural products, Mar-23, Volume: 75, Issue:3
Library-based discovery and characterization of daphnane diterpenes as potent and selective HIV inhibitors in Daphne gnidium.
AID658563Cytotoxicity against human HEK293T cells after 4 days by Alamar blue assay2012Journal of natural products, Mar-23, Volume: 75, Issue:3
Library-based discovery and characterization of daphnane diterpenes as potent and selective HIV inhibitors in Daphne gnidium.
AID658568Down-regulation of CXCR4 expression in PHA- and IL-2-stimulated human PBMC membranes at 20 nM after 48 hrs by flow cytometric analysis2012Journal of natural products, Mar-23, Volume: 75, Issue:3
Library-based discovery and characterization of daphnane diterpenes as potent and selective HIV inhibitors in Daphne gnidium.
AID658569Down-regulation of CCR5 expression in PHA- and IL-2-stimulated human PBMC membranes at 20 nM after 48 hrs by flow cytometric analysis2012Journal of natural products, Mar-23, Volume: 75, Issue:3
Library-based discovery and characterization of daphnane diterpenes as potent and selective HIV inhibitors in Daphne gnidium.
AID658565Antiviral activity against multidrug-resistant HIV1 106-PR infected in HEK293T cells assessed as inhibition of viral replication after 4 days by beta-galactosidase reporter gene assay2012Journal of natural products, Mar-23, Volume: 75, Issue:3
Library-based discovery and characterization of daphnane diterpenes as potent and selective HIV inhibitors in Daphne gnidium.
AID658683Antiviral activity against wild type Human immunodeficiency virus 1 NL4-3 pseudotyped with VSV envelope infected in human HeLa-SxR5 cells assessed as inhibition of viral replication after 3 days by beta-galactosidase assay2012Journal of natural products, Mar-23, Volume: 75, Issue:3
Library-based discovery and characterization of daphnane diterpenes as potent and selective HIV inhibitors in Daphne gnidium.
AID658562Antiviral activity against CCR5-tropic HIV1 NL-AD87 infected in HEK293T cells assessed as inhibition of viral replication after 4 days by beta-galactosidase reporter gene assay2012Journal of natural products, Mar-23, Volume: 75, Issue:3
Library-based discovery and characterization of daphnane diterpenes as potent and selective HIV inhibitors in Daphne gnidium.
AID658564Antiviral activity against multidrug-resistant HIV1 695-RT infected in HEK293T cells assessed as inhibition of viral replication after 4 days by beta-galactosidase reporter gene assay2012Journal of natural products, Mar-23, Volume: 75, Issue:3
Library-based discovery and characterization of daphnane diterpenes as potent and selective HIV inhibitors in Daphne gnidium.
AID658566Resistance factor, ratio of EC50 for multidrug-resistant HIV1 695-RT infected in HEK293T cells to wildtype HIV1 infected in HEK293T cells2012Journal of natural products, Mar-23, Volume: 75, Issue:3
Library-based discovery and characterization of daphnane diterpenes as potent and selective HIV inhibitors in Daphne gnidium.
AID658561Antiviral activity against CXCR4-tropic HIV1 NL4-3 infected in HEK293T cells assessed as inhibition of viral replication after 4 days by beta-galactosidase reporter gene assay2012Journal of natural products, Mar-23, Volume: 75, Issue:3
Library-based discovery and characterization of daphnane diterpenes as potent and selective HIV inhibitors in Daphne gnidium.
AID658684Antiviral activity against wild type Human immunodeficiency virus 1 NL4-3 pseudotyped with HIV envelope infected in human HeLa-SxR5 cells assessed as inhibition of viral replication after 3 days by beta-galactosidase assay2012Journal of natural products, Mar-23, Volume: 75, Issue:3
Library-based discovery and characterization of daphnane diterpenes as potent and selective HIV inhibitors in Daphne gnidium.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (6)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's5 (83.33)29.6817
2010's1 (16.67)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: 25.67

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 Index25.67 (24.57)
Research Supply Index1.95 (2.92)
Research Growth Index4.28 (4.65)
Search Engine Demand Index26.67 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (25.67)

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%
Other6 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]