Page last updated: 2024-12-08

neriifolin

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

Description

neriifolin: structure in first source; RN given refers to alpha-L-glucopyranosyl(3beta,5beta)-isomer [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

neriifolin : A cardenolide glycoside that is digitoxigenin in which the hydroxy goup at position 3 has been converted to its (6-deoxy-3-O-methyl-alpha-L-glucopyranoside derivative. Found in the seeds of Cerbera odollamand in Thevetia ahouia and Thevitia neriifolia. [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
ThevetiagenusA plant genus of the family APOCYNACEAE. Members contain thevetin.[MeSH]ApocynaceaeThe dogbane family of the order Gentianales. Members of the family have milky, often poisonous juice, smooth-margined leaves, and flowers in clusters.[MeSH]
CerberagenusA plant genus of the family APOCYNACEAE. Members contain CARDENOLIDES.[MeSH]ApocynaceaeThe dogbane family of the order Gentianales. Members of the family have milky, often poisonous juice, smooth-margined leaves, and flowers in clusters.[MeSH]

Cross-References

ID SourceID
PubMed CID441867
CHEMBL ID501533
CHEBI ID7522
SCHEMBL ID644057
MeSH IDM0121014

Synonyms (31)

Synonym
brn 0100752
5-beta-card-20(22)-enolide, 3-beta-((6-deoxy-3-o-methyl-beta-l-glucopyranosyl)oxy)-14-hydroxy-
digitoxigenin + thevetose [german]
(5beta)-3beta-((6-deoxy-3-o-methyl-alpha-l-glucopyranosyl)oxy)-14-hydroxycard-20(22)-enolide
nsc 123976
einecs 207-372-5
CHEBI:7522 ,
3beta-(6-deoxy-3-o-methyl-alpha-l-glucopyranosyloxy)-14-hydroxy-5beta-card-20(22)-enolide
466-07-9
digitoxigenin 3-(alpha-l-thevetoside)
neriifolin
C08876
3-[(3s,5r,8r,9s,10s,13r,14s,17r)-3-[(2r,3s,4r,5s,6s)-3,5-dihydroxy-4-methoxy-6-methyloxan-2-yl]oxy-14-hydroxy-10,13-dimethyl-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl]-2h-furan-5-one
CHEMBL501533
LMST01120021
unii-5rd2ads9wv
digitoxigenin + thevetose
5rd2ads9wv ,
SCHEMBL644057
17.beta.-neriifolin
neriifolin [mi]
card-20(22)-enolide, 3-((6-deoxy-3-o-methyl-.alpha.-l-glucopyranosyl)oxy)-14-hydroxy-, (3.beta.,5.beta.)-
mfcd00869436
DTXSID40881390
Q27107523
MS-29886
E88654
17beta-neriifolin
CS-0144224
HY-N8441
(3beta,5beta)-3-[(6-deoxy-3-o-methyl-alpha-l-glucopyranosyl)oxy]card-20(22)-enolide

Research Excerpts

Actions

ExcerptReferenceRelevance
"17βH-neriifolin had shown to cause apoptotic cell death in the respective cancer cell lines.17βH-neriifolin and ouabain both bound at α-subunit in Na+, K+-ATPase and their binding energy were -8.16 ± 0.74 kcal/mol and -8.18 ± 0.48 kcal/mol respectively."( The In Vitro Anti-Cancer Activities of 17βH-Neriifolin Isolated from Cerbera odollam and its Binding Activity on Na+, K+-ATPase.
Jauri, MH; Mutalip, SSM; Osman, A; Sallehudin, NJ; Yunos, NM, 2020
)
1.27

Toxicity

ExcerptReferenceRelevance
" It has been shown that the mutant protein is toxic in cell culture and triggers an apoptotic cascade resulting in activation of caspase-3."( A screen for drugs that protect against the cytotoxicity of polyglutamine-expanded androgen receptor.
Fischbeck, KH; Piccioni, F; Roman, BR; Taylor, JP, 2004
)
0.32

Compound-Compound Interactions

ExcerptReferenceRelevance
" Selected cardiac glycosides were tested in combination with four clinically relevant cytotoxic drugs (5-fluorouracil, oxaliplatin, cisplatin, irinotecan)."( Cytotoxic effects of cardiac glycosides in colon cancer cells, alone and in combination with standard chemotherapeutic drugs.
Bohlin, L; Felth, J; Fryknäs, M; Gullbo, J; Lindskog, M; Rickardson, L; Rosén, J; Wickström, M, 2009
)
0.35
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (3)

RoleDescription
cardiotonic drugA drug that has a strengthening effect on the heart or that can increase cardiac output.
toxinPoisonous substance produced by a biological organism such as a microbe, animal or plant.
neuroprotective agentAny compound that can be used for the treatment of neurodegenerative disorders.
[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 (1)

ClassDescription
cardenolide glycosideAny member of the class of cardenolides with glycosyl residues attached to position 3.
[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 (19)

Assay IDTitleYearJournalArticle
AID467917Cytotoxicity against human TRAIL-resistant AGS cells at 29.2 nM after 24 hrs by FMCA in absence of TRAIL2009Journal of natural products, Aug, Volume: 72, Issue:8
Cardenolide glycosides of Thevetia peruviana and triterpenoid saponins of Sapindus emarginatus as TRAIL resistance-overcoming compounds.
AID127351Binding affinity against human monoclonal antibody (mAb)-5C22002Journal of medicinal chemistry, Jul-18, Volume: 45, Issue:15
Three-dimensional quantitative structure-activity relationship analysis of ligand binding to human sequence antidigoxin monoclonal antibodies using comparative molecular field analysis.
AID335137DNA damaging activity against DNA repair-deficient Saccharomyces cerevisiae W303-1A RS188N mutant assessed as drug concentration required to produce 12 mm zone of inhibition up to 800 ug/well by agar diffusion assay1993Journal of natural products, Sep, Volume: 56, Issue:9
A screen for inhibitors of DNA recombination: identification of two new spirostanol glycosides from Chamaedorea linearis.
AID977602Inhibition of sodium fluorescein uptake in OATP1B3-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM2013Molecular pharmacology, Jun, Volume: 83, Issue:6
Structure-based identification of OATP1B1/3 inhibitors.
AID977599Inhibition of sodium fluorescein uptake in OATP1B1-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM2013Molecular pharmacology, Jun, Volume: 83, Issue:6
Structure-based identification of OATP1B1/3 inhibitors.
AID471509Cytotoxicity against human HCT116 cells assessed as survival index at 10 uM after 72 hrs by FMCA method2009Journal of natural products, Nov, Volume: 72, Issue:11
Cytotoxic effects of cardiac glycosides in colon cancer cells, alone and in combination with standard chemotherapeutic drugs.
AID127349Binding affinity against human monoclonal antibody (mAb)-11E62002Journal of medicinal chemistry, Jul-18, Volume: 45, Issue:15
Three-dimensional quantitative structure-activity relationship analysis of ligand binding to human sequence antidigoxin monoclonal antibodies using comparative molecular field analysis.
AID467915Cytotoxicity against human TRAIL-resistant AGS cells at 29.2 nM after 24 hrs by FMCA in presence of TRAIL2009Journal of natural products, Aug, Volume: 72, Issue:8
Cardenolide glycosides of Thevetia peruviana and triterpenoid saponins of Sapindus emarginatus as TRAIL resistance-overcoming compounds.
AID1293285Induction of apoptosis in human MGC803 cells after 24 hrs by annexin V-FITC/propidium iodide staining-based flow cytometry2016Journal of natural products, Jan-22, Volume: 79, Issue:1
Cardiac Glycosides from the Seeds of Thevetia peruviana.
AID1293284Cytotoxicity against human LO2 cells after 48 hrs by MTT assay2016Journal of natural products, Jan-22, Volume: 79, Issue:1
Cardiac Glycosides from the Seeds of Thevetia peruviana.
AID1293281Cytotoxicity against human P15 cells after 48 hrs by MTT assay2016Journal of natural products, Jan-22, Volume: 79, Issue:1
Cardiac Glycosides from the Seeds of Thevetia peruviana.
AID1293282Cytotoxicity against human MGC803 cells after 48 hrs by MTT assay2016Journal of natural products, Jan-22, Volume: 79, Issue:1
Cardiac Glycosides from the Seeds of Thevetia peruviana.
AID127352Binding affinity against human monoclonal antibody (mAb)-7F22002Journal of medicinal chemistry, Jul-18, Volume: 45, Issue:15
Three-dimensional quantitative structure-activity relationship analysis of ligand binding to human sequence antidigoxin monoclonal antibodies using comparative molecular field analysis.
AID421891Insecticidal activity against Ostrinia nubilalis2009Journal of natural products, Mar-27, Volume: 72, Issue:3
Plant seeds as sources of potential industrial chemicals, pharmaceuticals, and pest control agents.
AID127350Binding affinity against human monoclonal antibody (mAb)-1B32002Journal of medicinal chemistry, Jul-18, Volume: 45, Issue:15
Three-dimensional quantitative structure-activity relationship analysis of ligand binding to human sequence antidigoxin monoclonal antibodies using comparative molecular field analysis.
AID1293283Cytotoxicity against human SW1990 cells after 48 hrs by MTT assay2016Journal of natural products, Jan-22, Volume: 79, Issue:1
Cardiac Glycosides from the Seeds of Thevetia peruviana.
AID471508Cytotoxicity against human CC20 cells assessed as survival index at 10 uM after 72 hrs by FMCA method2009Journal of natural products, Nov, Volume: 72, Issue:11
Cytotoxic effects of cardiac glycosides in colon cancer cells, alone and in combination with standard chemotherapeutic drugs.
AID471510Cytotoxicity against human HT-29 cells assessed as survival index at 10 uM after 72 hrs by FMCA method2009Journal of natural products, Nov, Volume: 72, Issue:11
Cytotoxic effects of cardiac glycosides in colon cancer cells, alone and in combination with standard chemotherapeutic drugs.
AID127479Binding affinity against murine monoclonal antibody (mAb)-40-502002Journal of medicinal chemistry, Jul-18, Volume: 45, Issue:15
Three-dimensional quantitative structure-activity relationship analysis of ligand binding to human sequence antidigoxin monoclonal antibodies using comparative molecular field analysis.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (29)

TimeframeStudies, This Drug (%)All Drugs %
pre-19908 (27.59)18.7374
1990's2 (6.90)18.2507
2000's6 (20.69)29.6817
2010's9 (31.03)24.3611
2020's4 (13.79)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 24.83

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 Index24.83 (24.57)
Research Supply Index3.40 (2.92)
Research Growth Index4.90 (4.65)
Search Engine Demand Index26.67 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (24.83)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews1 (3.45%)6.00%
Case Studies2 (6.90%)4.05%
Observational0 (0.00%)0.25%
Other26 (89.66%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]