Compounds > convalloside
Page last updated: 2024-12-07

convalloside

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Description

Convalloside is a cardiac glycoside found in the lily of the valley (Convallaria majalis). It has a complex structure consisting of a steroid nucleus, a sugar moiety (glucose), and a lactone ring. It is synthesized by the plant via a series of enzymatic reactions involving precursors like digitoxin and strophanthidin. Convalloside exerts a potent positive inotropic effect, meaning it strengthens the heart muscle contractions. It is also known to have a negative chronotropic effect, slowing down the heart rate. This compound has been used traditionally in herbal medicine for treating heart conditions. However, due to its narrow therapeutic index and potential for toxicity, its use is limited. Researchers are studying convalloside to understand its mechanism of action and to explore its potential for developing new therapeutic agents for heart failure and other cardiovascular diseases. Its ability to interact with the Na+/K+ ATPase pump in cardiac muscle cells is of particular interest. Convalloside is also being investigated for its potential anti-inflammatory and anticancer properties.'

convalloside: neoconvalloside is the stereoisomer of convalloside; RN refers to (3beta,5beta)-isomer; structure given in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID114652
CHEMBL ID1169677
CHEBI ID176297
MeSH IDM0230411

Synonyms (14)

Synonym
CHEBI:176297
(3s,5s,8r,9s,10s,13r,14s,17r)-3-[(2r,3r,4s,5r,6s)-3,4-dihydroxy-6-methyl-5-[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-5,14-dihydroxy-13-methyl-17-(5-oxo-2h-uran-3-yl)-2,3,4,6,7,8,9,11,12,15,16,17-dodecahydro-1h-cyclopen
13473-51-3
einecs 236-749-7
card-20(22)-enolide, 3-((6-deoxy-4-o-beta-d-glucopyranosyl-alpha-l-mannopyranosyl)oxy)-5,14-dihydroxy-19-oxo-, (3beta,5alpha)-
bogoroside
(3beta,5beta)-3-((6-deoxy-4-o-beta-d-glucopyranosyl-alpha-l-mannopyranosyl)oxy)-5,14-dihydroxy-19-oxocard-20(22)-enolide
convallosid [german]
convalloside
CHEMBL1169677
3-[3,4-dihydroxy-6-methyl-5-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-5,14-dihydroxy-13-methyl-17-(5-oxo-2h-furan-3-yl)-2,3,4,6,7,8,9,11,12,15,16,17-dodecahydro-1h-cyclopenta[a]phenanthrene-10-carbaldehyde
(3s,5s,8r,9s,10s,13r,14s,17r)-3-[(2r,3r,4s,5r,6s)-3,4-dihydroxy-6-methyl-5-[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-5,14-dihydroxy-13-methyl-17-(5-oxo-2h-furan-3-yl)-2,3,4,6,7,8,9,11,12,15,16,17-dodecahydro-1h-cyclope
C19986
DTXSID40928734
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

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 (16)

Assay IDTitleYearJournalArticle
AID492117Cardiotonic activity in guinea pig right ventricular muscles assessed as maximum positive inotropic effective concentration causing myocardial contraction relative to basal level2010Journal of natural products, Jul-23, Volume: 73, Issue:7
Cardiac glycosides from Antiaris toxicaria with potent cardiotonic activity.
AID1072825Cytotoxicity against human SK-MEL-2 cells assessed as growth inhibition after 72 hrs by SRB assay2014Bioorganic & medicinal chemistry, Mar-15, Volume: 22, Issue:6
Cytotoxic cardiac glycosides and coumarins from Antiaris toxicaria.
AID492119Safety index, ratio of arrhythmogenic concentration to minimum positive inotropic effective concentration causing myocardial contraction in guinea pig right ventricular muscles2010Journal of natural products, Jul-23, Volume: 73, Issue:7
Cardiac glycosides from Antiaris toxicaria with potent cardiotonic activity.
AID492118Safety index, ratio of arrhythmogenic concentration to minimum positive inotropic effective concentration causing myocardial contraction in guinea pig left atrial muscles2010Journal of natural products, Jul-23, Volume: 73, Issue:7
Cardiac glycosides from Antiaris toxicaria with potent cardiotonic activity.
AID1072830Cytotoxicity against human U87MG cells assessed as growth inhibition after 72 hrs by SRB assay2014Bioorganic & medicinal chemistry, Mar-15, Volume: 22, Issue:6
Cytotoxic cardiac glycosides and coumarins from Antiaris toxicaria.
AID1072831Cytotoxicity against human MCF7 cells assessed as growth inhibition after 72 hrs by SRB assay2014Bioorganic & medicinal chemistry, Mar-15, Volume: 22, Issue:6
Cytotoxic cardiac glycosides and coumarins from Antiaris toxicaria.
AID492115Cardiotonic activity in guinea pig right ventricular muscles assessed as minimum positive inotropic effective concentration causing myocardial contraction2010Journal of natural products, Jul-23, Volume: 73, Issue:7
Cardiac glycosides from Antiaris toxicaria with potent cardiotonic activity.
AID1072834Cytotoxicity against human KB cells assessed as growth inhibition after 72 hrs by SRB assay2014Bioorganic & medicinal chemistry, Mar-15, Volume: 22, Issue:6
Cytotoxic cardiac glycosides and coumarins from Antiaris toxicaria.
AID1072833Cytotoxicity against human KBVIN cells assessed as growth inhibition after 72 hrs by SRB assay2014Bioorganic & medicinal chemistry, Mar-15, Volume: 22, Issue:6
Cytotoxic cardiac glycosides and coumarins from Antiaris toxicaria.
AID1072827Cytotoxicity against human CAKI-1 cells assessed as growth inhibition after 72 hrs by SRB assay2014Bioorganic & medicinal chemistry, Mar-15, Volume: 22, Issue:6
Cytotoxic cardiac glycosides and coumarins from Antiaris toxicaria.
AID492114Cardiotonic activity in guinea pig left atrial muscles assessed as minimum positive inotropic effective concentration causing myocardial contraction2010Journal of natural products, Jul-23, Volume: 73, Issue:7
Cardiac glycosides from Antiaris toxicaria with potent cardiotonic activity.
AID1072832Cytotoxicity against human A549 cells assessed as growth inhibition after 72 hrs by SRB assay2014Bioorganic & medicinal chemistry, Mar-15, Volume: 22, Issue:6
Cytotoxic cardiac glycosides and coumarins from Antiaris toxicaria.
AID1072828Cytotoxicity against human 1A9 cells assessed as growth inhibition after 72 hrs by SRB assay2014Bioorganic & medicinal chemistry, Mar-15, Volume: 22, Issue:6
Cytotoxic cardiac glycosides and coumarins from Antiaris toxicaria.
AID492116Cardiotonic activity in guinea pig left atrial muscles assessed as maximum positive inotropic effective concentration causing myocardial contraction relative to basal level2010Journal of natural products, Jul-23, Volume: 73, Issue:7
Cardiac glycosides from Antiaris toxicaria with potent cardiotonic activity.
AID1072829Cytotoxicity against human PC3 cells assessed as growth inhibition after 72 hrs by SRB assay2014Bioorganic & medicinal chemistry, Mar-15, Volume: 22, Issue:6
Cytotoxic cardiac glycosides and coumarins from Antiaris toxicaria.
AID1072826Cytotoxicity against human HCT9 cells assessed as growth inhibition after 72 hrs by SRB assay2014Bioorganic & medicinal chemistry, Mar-15, Volume: 22, Issue:6
Cytotoxic cardiac glycosides and coumarins from Antiaris toxicaria.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (5)

TimeframeStudies, This Drug (%)All Drugs %
pre-19901 (20.00)18.7374
1990's1 (20.00)18.2507
2000's0 (0.00)29.6817
2010's3 (60.00)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: 20.29

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 Index20.29 (24.57)
Research Supply Index2.08 (2.92)
Research Growth Index4.73 (4.65)
Search Engine Demand Index15.26 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (20.29)

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%
Other7 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
strophanthidin
Strophanthidin: 3 beta,5,14-Trihydroxy-19-oxo-5 beta-card-20(22)-enolide. The aglycone cardioactive agent isolated from Strophanthus Kombe, S. gratus and other species; it is a very toxic material formerly used as digitalis. Synonyms: Apocymarin; Corchorin; Cynotoxin; Corchorgenin.		2.482014beta-hydroxy steroid;
19-oxo steroid;
3beta-hydroxy steroid;
5beta-hydroxy steroid;
cardenolides;
steroid aldehyde
periplogenin
periplogenin: structure		1.9810
marmesin
marmesin: RN given refers to (S)-isomer; nodakenetin is the (R)-isomer		2.110marmesin
ouabain
Ouabain: A cardioactive glycoside consisting of rhamnose and ouabagenin, obtained from the seeds of Strophanthus gratus and other plants of the Apocynaceae; used like DIGITALIS. It is commonly used in cell biological studies as an inhibitor of the NA(+)-K(+)-EXCHANGING ATPASE.. cardiac glycoside : Steroid lactones containing sugar residues that act on the contractile force of the cardiac muscles.. ouabain : A steroid hormone that is a multi-hydroxylated alpha-L-rhamnosyl cardenoloide. It binds to and inhibits the plasma membrane Na(+)/K(+)-ATPase (sodium pump). It has been isolated naturally from Strophanthus gratus.		2.051011alpha-hydroxy steroid;
14beta-hydroxy steroid;
5beta-hydroxy steroid;
alpha-L-rhamnoside;
cardenolide glycoside;
steroid hormone		anti-arrhythmia drug;
cardiotonic drug;
EC 2.3.3.1 [citrate (Si)-synthase] inhibitor;
EC 3.1.3.41 (4-nitrophenylphosphatase) inhibitor;
EC 3.6.3.10 (H(+)/K(+)-exchanging ATPase) inhibitor;
EC 3.6.3.9 (Na(+)/K(+)-transporting ATPase) inhibitor;
ion transport inhibitor;
plant metabolite
convallatoxin
convallatoxin: PI: *CONVALLARIA (73-79). convallatoxin : A cardenolide glycoside that consists of strophanthidin having a 6-deoxy-alpha-L-mannopyranosyl (L-rhamnosyl) group attached at position 3.		2.773014beta-hydroxy steroid;
19-oxo steroid;
5beta-hydroxy steroid;
alpha-L-rhamnoside;
steroid aldehyde;
steroid lactone		metabolite;
vasodilator agent
glycosides
[no description available]		2.6630
digitoxigenin
Digitoxigenin: 3 beta,14-Dihydroxy-5 beta-card-20(22)enolide. A cardenolide which is the aglycon of digitoxin. Synonyms: Cerberigenin; Echujetin; Evonogenin; Thevetigenin.. digitoxigenin : A 5beta-cardenolide that is 5beta-cardanolide with hydroxy substituents at the 3beta- and 14beta-positions and double bond unsaturation at C(20)-C(22).		1.981014beta-hydroxy steroid;
3beta-hydroxy steroid
ConditionIndicatedRelationship StrengthStudiesTrials
Food Poisoning
[description not available]		02.110
Cardiac Failure
[description not available]		01.9310
Heart Failure
A heterogeneous condition in which the heart is unable to pump out sufficient blood to meet the metabolic need of the body. Heart failure can be caused by structural defects, functional abnormalities (VENTRICULAR DYSFUNCTION), or a sudden overload beyond its capacity. Chronic heart failure is more common than acute heart failure which results from sudden insult to cardiac function, such as MYOCARDIAL INFARCTION.		01.9310
Goldblatt Syndrome
[description not available]		01.9810
Hypertension, Renovascular
Hypertension due to RENAL ARTERY OBSTRUCTION or compression.		01.9810