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Convallatoxin

PubChem CID
441852
Structure
Convallatoxin_small.png
Convallatoxin_3D_Structure.png
Molecular Formula
Synonyms
  • Convallatoxin
  • 508-75-8
  • Corglycone
  • Convallotoxin
  • Convallaton
Molecular Weight
550.6 g/mol
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Dates
  • Create:
    2005-06-24
  • Modify:
    2025-02-01
Description
Convallatoxin is a cardenolide glycoside that consists of strophanthidin having a 6-deoxy-alpha-L-mannopyranosyl (L-rhamnosyl) group attached at position 3. It has a role as a vasodilator agent and a metabolite. It is an alpha-L-rhamnoside, a 19-oxo steroid, a 14beta-hydroxy steroid, a 5beta-hydroxy steroid, a steroid lactone and a steroid aldehyde. It is functionally related to a strophanthidin.
Convallatoxin has been reported in Convallaria majalis, Saussurea stella, and other organisms with data available.
Convallatoxin is a glycoside extracted from Convallaria majalis. Convallatoxin is also isolated from the trunk bark of Antiaris toxicaria (A15340).
A15340: Yang SY, Kim NH, Cho YS, Lee H, Kwon HJ: Convallatoxin, a dual inducer of autophagy and apoptosis, inhibits angiogenesis in vitro and in vivo. PLoS One. 2014 Mar 24;9(3):e91094. doi: 10.1371/journal.pone.0091094. eCollection 2014. PMID:24663328

1 Structures

1.1 2D Structure

Chemical Structure Depiction
Convallatoxin.png

1.2 3D Conformer

2 Names and Identifiers

2.1 Computed Descriptors

2.1.1 IUPAC Name

(3S,5S,8R,9S,10S,13R,14S,17R)-5,14-dihydroxy-13-methyl-17-(5-oxo-2H-furan-3-yl)-3-[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy-2,3,4,6,7,8,9,11,12,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-10-carbaldehyde
Computed by Lexichem TK 2.7.0 (PubChem release 2021.10.14)

2.1.2 InChI

InChI=1S/C29H42O10/c1-15-22(32)23(33)24(34)25(38-15)39-17-3-8-27(14-30)19-4-7-26(2)18(16-11-21(31)37-13-16)6-10-29(26,36)20(19)5-9-28(27,35)12-17/h11,14-15,17-20,22-25,32-36H,3-10,12-13H2,1-2H3/t15-,17-,18+,19-,20+,22-,23+,24+,25-,26+,27-,28-,29-/m0/s1
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.3 InChIKey

HULMNSIAKWANQO-JQKSAQOKSA-N
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.4 SMILES

C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)O[C@H]2CC[C@@]3([C@H]4CC[C@@]5([C@H](CC[C@@]5([C@@H]4CC[C@@]3(C2)O)O)C6=CC(=O)OC6)C)C=O)O)O)O
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)

2.2 Molecular Formula

C29H42O10
Computed by PubChem 2.2 (PubChem release 2021.10.14)

2.3 Other Identifiers

2.3.1 CAS

2.3.2 European Community (EC) Number

2.3.3 UNII

2.3.4 ChEBI ID

2.3.5 ChEMBL ID

2.3.6 DSSTox Substance ID

2.3.7 KEGG ID

2.3.8 Lipid Maps ID (LM_ID)

2.3.9 Metabolomics Workbench ID

2.3.10 Nikkaji Number

2.3.11 Wikidata

2.3.12 Wikipedia

2.4 Synonyms

2.4.1 MeSH Entry Terms

  • convallatoxin
  • corglycon
  • corglycone
  • korglycon
  • strophanthidin-alpha-L-rhamnoside

2.4.2 Depositor-Supplied Synonyms

3 Chemical and Physical Properties

3.1 Computed Properties

Property Name
Molecular Weight
Property Value
550.6 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
XLogP3
Property Value
-0.7
Reference
Computed by XLogP3 3.0 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Donor Count
Property Value
5
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Acceptor Count
Property Value
10
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Rotatable Bond Count
Property Value
4
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Exact Mass
Property Value
550.27779753 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Monoisotopic Mass
Property Value
550.27779753 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Topological Polar Surface Area
Property Value
163 Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Heavy Atom Count
Property Value
39
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
1050
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Isotope Atom Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Atom Stereocenter Count
Property Value
13
Reference
Computed by PubChem
Property Name
Undefined Atom Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Undefined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Covalently-Bonded Unit Count
Property Value
1
Reference
Computed by PubChem
Property Name
Compound Is Canonicalized
Property Value
Yes
Reference
Computed by PubChem (release 2021.10.14)

3.2 Experimental Properties

3.2.1 Physical Description

Solid; [Merck Index]

3.2.2 Color / Form

Prisms from methanol + ether
O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Cambridge, UK: Royal Society of Chemistry, 2013., p. 448
Crystals or prisms from methanol or ether
Lewis, R.J. Sr. (ed) Sax's Dangerous Properties of Industrial Materials. 12th Edition. Wiley-Interscience, Wiley & Sons, Inc. Hoboken, NJ. 2012., p. V1: 203

3.2.3 Melting Point

235-242 °C
O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Cambridge, UK: Royal Society of Chemistry, 2013., p. 448

3.2.4 Solubility

Slightly soluble in water
Lewis, R.J. Sr. (ed) Sax's Dangerous Properties of Industrial Materials. 12th Edition. Wiley-Interscience, Wiley & Sons, Inc. Hoboken, NJ. 2012., p. V1: 1203
Soluble in alcohol, acetone; slightly soluble in chloroform, ethyl acetate; practically insoluble in ether, petroleum ether
O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Cambridge, UK: Royal Society of Chemistry, 2013., p. 448

3.2.5 LogP

log Kow = -0.28
Sangster J; LOGKOW Databank. Sangster Res. Lab., Montreal Quebec, Canada (1993)

3.2.6 Stability / Shelf Life

Stable under recommended storage conditions.
Sigma-Aldrich; Safety Data Sheet for Convallatoxin, Product Number: PHL80834, Version 5.0 (Revision Date 09/07/2018). Available from, as of September 11, 2018: https://www.sigmaaldrich.com/safety-center.html

3.2.7 Optical Rotation

Specific optical rotation: -1.7 deg deg at 22 °C/D (c = 0.65 in methanol); -9.4 deg 3 deg at 25 °C/D (c = 0.65 in dioxane)
O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Cambridge, UK: Royal Society of Chemistry, 2013., p. 448

3.2.8 Decomposition

Hazardous decomposition products formed under fire conditions. - Carbon oxides
Sigma-Aldrich; Safety Data Sheet for Convallatoxin, Product Number: PHL80834, Version 5.0 (Revision Date 09/07/2018). Available from, as of September 11, 2018: https://www.sigmaaldrich.com/safety-center.html
When heated to decomposition it emits acrid smoke ans fumes.
Lewis, R.J. Sr. (ed) Sax's Dangerous Properties of Industrial Materials. 11th Edition. Wiley-Interscience, Wiley & Sons, Inc. Hoboken, NJ. 2004., p. 985

3.2.9 Collision Cross Section

238.97 Ų [M+Na]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

244.38 Ų [M+K]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

216.57 Ų [M+H-H2O]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

Ross et al. JASMS 2022; 33; 1061-1072. DOI:10.1021/jasms.2c00111
238.1 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

3.2.10 Other Experimental Properties

/Tests positive for/ Legal's Reaction /SRP: "Legal's test for acetone consists of adding the the liquid a few drops of a solution of sodium nitroprusside, followed by caustic alkali; a red coloration is produced, and gradually diminishes, but deepens to carmine on treatment with excess glacial acetic acid" J Chem Soc (London) 72 Part 2. Analytical Chemistry, page 467. Jan 1, 1897/
O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Cambridge, UK: Royal Society of Chemistry, 2013., p. 448
Needles from acetone + ether, MP: 215-239 °C. Specific optical rotation: -5.5 deg at 25 °C/D (c = 0.962 in chloroform) /Tri-O-acetyl-convallatoxin/
O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Cambridge, UK: Royal Society of Chemistry, 2013., p. 448

3.3 Chemical Classes

Biological Agents -> Plant Toxins

3.3.1 Lipids

Lipids -> Sterol Lipids [ST] -> Sterols [ST01] -> Cardanolides and derivatives [ST0112]

4 Spectral Information

4.1 1D NMR Spectra

4.1.1 13C NMR Spectra

1 of 2
Copyright
Copyright © 2016-2024 W. Robien, Inst. of Org. Chem., Univ. of Vienna. All Rights Reserved.
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Copyright
Copyright © 2016-2024 W. Robien, Inst. of Org. Chem., Univ. of Vienna. All Rights Reserved.
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4.2 Mass Spectrometry

4.2.1 LC-MS

1 of 3
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MoNA ID
MS Category
Experimental
MS Type
LC-MS
MS Level
MS1
Instrument
ZQ, Waters
Instrument Type
LC-ESI-Q
Ionization
ESI
Ionization Mode
negative
Retention Time
12.870 min
Top 5 Peaks

595 100

585 29.03

596 27.43

612 21.52

549 20.82

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License
CC BY-NC
2 of 3
View All
MoNA ID
MS Category
Experimental
MS Type
LC-MS
MS Level
MS1
Instrument
ZQ, Waters
Instrument Type
LC-ESI-Q
Ionization
ESI
Ionization Mode
positive
Retention Time
12.870 min
Top 5 Peaks

568 100

551 88.59

163 58.46

405 38.44

552 30.63

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License
CC BY-NC

4.2.2 Other MS

1 of 3
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MoNA ID
MS Category
Experimental
MS Type
Other
MS Level
MS2
Precursor Type
[M+Na]+
Precursor m/z
573.2670155
Ionization Mode
positive
Retention Time
1.375453568716623
Top 5 Peaks

91.05501136331621 0.08

77.03834836331622 0.06

65.03846936331622 0.04

55.05344436331622 0.02

51.022718363316216 0.02

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2 of 3
View All
MoNA ID
MS Category
Experimental
MS Type
Other
MS Level
MS2
Precursor Type
[M+NH4]+
Precursor m/z
568.3116205
Ionization Mode
positive
Retention Time
1.3778780756121518
Top 5 Peaks

369.199189685717 0.09

341.21128734802784 0.08

359.2218851976562 0.07

323.2039390513423 0.06

405.22768273057693 0.05

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6 Chemical Vendors

7 Drug and Medication Information

7.1 Therapeutic Uses

Vasodilator Agents
National Library of Medicine's Medical Subject Headings online file (MeSH, 2018)
/EXPL THER/ Convallatoxin improved myocardial relaxation and elevated the rate and force of systolic heart contraction in dogs in the initial stages of cor pulmonale (in chronic pneumonia). The positive inotropic effect in experimental cor pulmonale with high pulmonary blood pressures was accompanied by increased overload on the right ventricle and further elevation of pulmonary blood pressures.
Frantsuzova SB, Antonenko LI; Farmakol Toksikol (Moscow) 44 (6): 688 (1981)
/EXPL THER/ Convallotoxin had no effect on left ventricular hemodynamics in intact dogs, but decreased right intraventricular pressure and increased dp/dt max and dp/dt minimum. In animals with surgical stenosis of the pulmonary trunk, an increase in pressure and dp/dt max of the right ventricle, a decrease in left ventricular end-diastolic pressure, and an increase in left dp/dt max were observed. Administration of convallotoxin to dogs 1 month following stenosis did not improve cardiohemodynamics.
Frantsuzova SB et al; Farmakol Toksikol (Moscow) 43 (6): 674 (1980)
/EXPL THER/ Cytomegalovirus (CMV) is a ubiquitous human pathogen that increases the morbidity and mortality of immunocompromised individuals. The current FDA-approved treatments for CMV infection are intended to be virus specific, yet they have significant adverse side effects, including nephrotoxicity and hematological toxicity. Thus, there is a medical need for safer and more effective CMV therapeutics. Using a high-content screen, we identified the cardiac glycoside convallatoxin as an effective compound that inhibits CMV infection. Using a panel of cardiac glycoside variants, we assessed the structural elements critical for anti-CMV activity by both experimental and in silico methods. Analysis of the antiviral effects, toxicities, and pharmacodynamics of different variants of cardiac glycosides identified the mechanism of inhibition as reduction of methionine import, leading to decreased immediate-early gene translation without significant toxicity. Also, convallatoxin was found to dramatically reduce the proliferation of clinical CMV strains, implying that its mechanism of action is an effective strategy to block CMV dissemination. Our study has uncovered the mechanism and structural elements of convallatoxin, which are important for effectively inhibiting CMV infection by targeting the expression of immediate-early genes. IMPORTANCE: Cytomegalovirus is a highly prevalent virus capable of causing severe disease in certain populations. The current FDA-approved therapeutics all target the same stage of the viral life cycle and induce toxicity and viral resistance. We identified convallatoxin, a novel cell-targeting antiviral that inhibits CMV infection by decreasing the synthesis of viral proteins. At doses low enough for cells to tolerate, convallatoxin was able to inhibit primary isolates of CMV, including those resistant to the anti-CMV drug ganciclovir. In addition to identifying convallatoxin as a novel antiviral, limiting mRNA translation has a dramatic impact on CMV infection and proliferation.
Cohen T et al; J Virol 90 (23): 10715-10727 (2016)

8 Pharmacology and Biochemistry

8.1 MeSH Pharmacological Classification

Vasodilator Agents
Drugs used to cause dilation of the blood vessels. (See all compounds classified as Vasodilator Agents.)

8.2 Absorption, Distribution and Excretion

The intestinal absorption of 15 cardenolides was examined after the (3)H-labeled substances were injected intraluminally into ligated duodenal loops of cats. Concentrations of (3)H were followed in the portal circulation and in the bile.
Hempelmann FW et al; Arzneim-Forsch 28 (12): 2182 (1978)
Isolated, everted rat jejunal preparations absorbed convallatoxin by an active transport mechanism. No relation was observed between the amount of cardiotonic glycoside actively transported and the oxygen consumption of the tissue.
Mentz P et al; Arch Int Pharmacodyn Ther 200 (1): 126 (1972)
Digitalis-like compounds (DLCs), such as digoxin and digitoxin that are derived from digitalis species, are currently used to treat heart failure and atrial fibrillation, but have a narrow therapeutic index. Drug-drug interactions at the transporter level are frequent causes of DLCs toxicity. P-glycoprotein (P-gp, ABCB1) is the primary transporter of digoxin and its inhibitors influence pharmacokinetics and disposition of digoxin in the human body; however, the involvement of P-gp in the disposition of other DLCs is currently unknown. In present study, the transport of fourteen DLCs by human P-gp was studied using membrane vesicles originating from human embryonic kidney (HEK293) cells overexpressing P-gp. DLCs were quantified by liquid chromatography-mass spectrometry (LC-MS). The Lily of the Valley toxin, convallatoxin, was identified as a P-gp substrate (Km: 1.1+/-0.2 mM) in the vesicular assay. Transport of convallatoxin by P-gp was confirmed in rat in vivo, in which co-administration with the P-gp inhibitor elacridar, resulted in increased concentrations in brain and kidney cortex. To address the interaction of convallatoxin with P-gp on a molecular level, the effect of nine alanine mutations was compared with the substrate N-methyl quinidine (NMQ). Phe343 appeared to be more important for transport of NMQ than convallatoxin, while Val982 was particularly relevant for convallatoxin transport. We identified convallatoxin as a new P-gp substrate and recognized Val982 as an important amino acid involved in its transport. ...
Gozalpour E et al; Eur J Pharmacol 744: 18-27 (2014)

8.3 Metabolism / Metabolites

Helveticoside and convallatoxin were converted hydrolytically into strophanthidine during perfusion through an isolated rat small intestine segment. Also, the C10-aldehyde group of these compounds was reduced enzymatically to helveticosol, convallatoxol, and strophanthidol. This reduction of strophanthidine cardenolides, beside the hydrolysis reaction, appeared to be the most important biotransformation reaction in the rat small intestine.
Zathurecky L et al; Sci Pharm 37 (2): 135 (1969)

8.4 Mechanism of Action

The inhibitory activity of glycosides and related compounds toward Na+-K+-ATPase was determined and related to their cardiotonic activity in cats. It appeared that the active site of Na+-K+-ATPase consists of 2 sections; 1 section binds the cardiosteroids to the receptor and orients the molecules relative to the 2nd or catalytic section. The relation of these results to the cardiotonic activity of strophanthidol analogs is discussed.
Mirsalikhova NM et al; NIH Publ NIH-80-2017, Energy Transp Protein Synth Horm Control Heart Metab 269 (1980)

9 Use and Manufacturing

9.1 Uses

Sources/Uses
Naturally occurring in lily of the valley blossoms; Used as a cardiotonic and veterinary diuretic; [Merck Index]
Merck Index - O'Neil MJ, Heckelman PE, Dobbelaar PH, Roman KJ (eds). The Merck Index, An Encyclopedia of Chemicals, Drugs, and Biologicals, 15th Ed. Cambridge, UK: The Royal Society of Chemistry, 2013.
MEDICATION
Convallatoxin is a glycoside extracted from Convallaria majalis. Convallatoxin is also isolated from the trunk bark of Antiaris toxicaria (A15340).
A15340: Yang SY, Kim NH, Cho YS, Lee H, Kwon HJ: Convallatoxin, a dual inducer of autophagy and apoptosis, inhibits angiogenesis in vitro and in vivo. PLoS One. 2014 Mar 24;9(3):e91094. doi: 10.1371/journal.pone.0091094. eCollection 2014. PMID:24663328

9.2 Methods of Manufacturing

Synthesis from strophanthidin and acetobromrhamnose: Reyle et al., Helv Chim Acta 33, 1541 (1950); Haede et al., German patent 1933090 (1971 to Hoechst).
O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Cambridge, UK: Royal Society of Chemistry, 2013., p. 448

9.3 Impurities

Convallatoxin batches made in Switzerland, West Germany, and Britain contained periguloside, convallatoxol, aglycons, and noncardenolides. The impurities were removed by column chromatography on neutral aluminum oxide-silica gel (1:1) by elution with CHCl3-ethanol (4:1).
BUCHVAROV Y ET AL; FARMATSIYA (SOFIA) 31(2) 44 (1981)

9.4 General Manufacturing Information

... Convallaria majalis (Lily of the Valley), yields cardiac glycoside, convallatoxin, which is not employed clinically but which possesses potent characteristic digitalis-like activity.
Gilman, A. G., L. S. Goodman, and A. Gilman. (eds.). Goodman and Gilman's The Pharmacological Basis of Therapeutics. 6th ed. New York: Macmillan Publishing Co., Inc. 1980., p. 730
A phytotoxin from the flowers of Adonis vernalis, convallaria majalis, ornthogalum umbellatum and antiaris toxicaria. The aglycone is convallatoxigenin and the sugar is a rhamnose.
Larranaga, M.D., Lewis, R.J. Sr., Lewis, R.A.; Hawley's Condensed Chemical Dictionary 16th Edition. John Wiley & Sons, Inc. Hoboken, NJ 2016., p. 367

10 Identification

10.1 Analytic Laboratory Methods

Determination of cardenolides in Convallaria majalis l by high-performance liquid chromatography.
Jurenitsch J et al; J Chromatogr 240 (1): 235 (1982)

10.2 Clinical Laboratory Methods

CONTEXT: Cardiac glycosides of plant origin are implicated in toxic ingestions that may result in hospitalization and are potentially lethal. The utility of commonly available digoxin serum assays for detecting foxglove and oleander ingestion has been demonstrated, but no studies have evaluated the structurally similar convallatoxin found in Convallaria majalis (lily of the valley) for rapid laboratory screening, nor has digoxin immune Fab been tested as an antidote for this ingestion. OBJECTIVE: We aimed to (1) evaluate multiple digoxin assays for cross-reactivity to convallatoxin, (2) identify whether convallatoxin could be detected in vivo at clinically significant doses, and (3) determine whether digoxin immune Fab could be an effective antidote to convallatoxin. MATERIALS AND METHODS: Cross-reactivities of purified convallatoxin and oleandrin with five common digoxin immunoassays were determined. Serum from mice challenged with convallatoxin was tested for apparent digoxin levels. Binding of convallatoxin to digoxin immune Fab was determined in vitro. RESULTS: Both convallatoxin and oleandrin were detectable by a panel of commonly used digoxin immunoassays, but cross-reactivity was variable between individual assays. We observed measurable apparent digoxin levels in serum of convallatoxin intoxicated mice at sublethal doses. Convallatoxin demonstrated no binding by digoxin immune Fab. CONCLUSION: Multiple digoxin immunoassays detect botanical cardiac glycosides including convallatoxin and thus may be useful for rapid determination of severe exposures, but neutralization of convallatoxin by digoxin immune Fab is unlikely to provide therapeutic benefit.
Fink SL et al; Clin Toxicol (Phila) 52 (7): 659-63 (2014)
Plant poisonings have left their mark on history and still cause many deaths, whether intentional or accidental. The means to show toxicological evidence of such poisonings should be implemented with great care. This article presents a technique for measuring thirty-nine toxic principles of plant origin in the blood, covering a large amount of toxins from local or exotic plants: a-lobeline, a-solanine, aconitine, ajmaline, atropine, brucine, cephalomannine, colchicine, convallatoxin, cymarine, cytisine, digitoxin, digoxin, emetine, gelsemine, ibogaine, jervine, kavain, lanatoside C, lupanine, mitragynine, neriifolin, oleandrin, ouabain, paclitaxel, physostigmine, pilocarpine, podophyllotoxin, proscillaridin A, reserpine, retrorsine, ricinine, scopolamine, senecionine, sparteine, strophanthidin, strychnine, veratridine and yohimbine. Analysis was carried out using an original ultra-high performance liquid chromatography separation coupled with tandem mass spectrometry detection. Extraction was a standard solid phase extraction performed on Oasis() HLB cartridge. Thirty-four of the thirty-nine compounds were put through a validation procedure. The assay was linear in the calibration curve range from 0.5 or 5 ug/L to 1000 ug/L according to the compounds. The method is sensitive (LOD from 0.1 to 1.6 ug/L). The within-day precision of the assay was less than 22.5% at the LLOQ, and the between-day precision was less than 21.5% for 10 ug/L for all the compounds included. The assay accuracy was in the range of 87.4 to 119.8% for the LLOQ. The extraction recovery and matrix effect ranged from 30 to 106% and from -30 to 14%, respectively. It has proven useful and effective in several difficult forensic cases.
Carlier J et al; J Chromatogr B Analyt Technol Biomed Life Sci 975: 65-76 (2015)
OBJECTIVE: Lily of the valley is a poisonous plant due to the presence of the cardiac glycoside convallatoxin. We compared two immunoassays (LOCI digoxin assay and iDigoxin assay) for rapid detection of convallatoxin if present in human serum. MATERIALS AND METHODS: Aliquots of a drug free serum pool and a digoxin serum pool were supplemented with microliter amounts of lily of the valley extract or nanogram to microgram quantities of convallatoxin, followed by measurement of apparent digoxin concentrations using the LOCI and iDigxoin assays. RESULTS: Apparent digoxin concentrations were observed when aliquots of a drug free serum pool were supplemented with convallatoxin or lily of the valley extract using both assays but apparent digoxin concentrations were significantly higher using the iDigoxin assay. In addition, the interference of convallatoxin in serum digoxin measurement was also significantly higher using iDigxoin assay compared to the LOCI digoxin assay. CONCLUSIONS: The iDigxoin assay is more sensitive in detecting convallatoxin in human serum.
Everett JM et al; Ann Clin Lab Sci 45 (3): 323-6 (2015)

11 Safety and Hazards

11.1 Hazards Identification

11.1.1 GHS Classification

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Pictogram(s)
Acute Toxic
Signal
Danger
GHS Hazard Statements

H301 (100%): Toxic if swallowed [Danger Acute toxicity, oral]

H311 (100%): Toxic in contact with skin [Danger Acute toxicity, dermal]

H331 (100%): Toxic if inhaled [Danger Acute toxicity, inhalation]

Precautionary Statement Codes

P261, P262, P264, P270, P271, P280, P301+P316, P302+P352, P304+P340, P316, P321, P330, P361+P364, P403+P233, P405, and P501

(The corresponding statement to each P-code can be found at the GHS Classification page.)

ECHA C&L Notifications Summary
The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.

11.1.2 Hazard Classes and Categories

Acute Tox. 3 (100%)

Acute Tox. 3 (100%)

Acute Tox. 3 (100%)

11.1.3 Hazards Summary

Emergency treatment: Cardiac glycosides; [HSDB] A review of 2693 lily of the valley exposures (93% children) found no fatalities with only 3 patients suffering a major outcome.[Ford, p. 924] Acute overdose of cardiac glycosides can cause vomiting, hyperkalemia, and arrhythmias. Chronic poisoning can cause visual disturbances, weakness, and arrhythmias. [Olson, p. 222-3] Oral LD50 (mouse) >2000 mg/kg; [RTECS] May cause irritation; Targets the cardiovascular system; [MSDSonline]
Ford - Ford MD, Delaney KA, Ling LJ, Erickson T (eds). Clinical Toxicology. Philadelphia: W.B. Saunders, 2001., p. 924
Olson - Olson KR (ed). Poisoning & Drug Overdose, 7th Ed. New York: Lange Medical Books/McGraw-Hill, 2018., p. 222-3

11.2 Fire Fighting

11.2.1 Fire Fighting Procedures

Suitable extinguishing media: Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide. Advice for firefighters: Wear self-contained breathing apparatus for firefighting if necessary
Sigma-Aldrich; Safety Data Sheet for Convallatoxin, Product Number: PHL80834, Version 5.0 (Revision Date 09/07/2018). Available from, as of September 11, 2018: https://www.sigmaaldrich.com/safety-center.html

11.3 Accidental Release Measures

11.3.1 Cleanup Methods

ACCIDENTAL RELEASE MEASURES; Personal precautions, protective equipment and emergency procedures: Wear respiratory protection. Avoid dust formation. Avoid breathing vapors, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust. Environmental precautions: Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Methods and materials for containment and cleaning up: Pick up and arrange disposal without creating dust. Sweep up and shovel. Keep in suitable, closed containers for disposal.
Sigma-Aldrich; Safety Data Sheet for Convallatoxin, Product Number: PHL80834, Version 5.0 (Revision Date 09/07/2018). Available from, as of September 11, 2018: https://www.sigmaaldrich.com/safety-center.html

11.3.2 Disposal Methods

SRP: Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in air, soil or water; effects on animal, aquatic and plant life; and conformance with environmental and public health regulations. If it is possible or reasonable use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity or environmental contamination.
Product: Offer surplus and non-recyclable solutions to a licensed disposal company. Contaminated packaging: Dispose of as unused product.
Sigma-Aldrich; Safety Data Sheet for Convallatoxin, Product Number: PHL80834, Version 5.0 (Revision Date 09/07/2018). Available from, as of September 11, 2018: https://www.sigmaaldrich.com/safety-center.html

11.3.3 Preventive Measures

Gloves must be inspected prior to use. Use proper glove removal technique (without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands.
Sigma-Aldrich; Safety Data Sheet for Convallatoxin, Product Number: PHL80834, Version 5.0 (Revision Date 09/07/2018). Available from, as of September 11, 2018: https://www.sigmaaldrich.com/safety-center.html
Avoid contact with skin and eyes. Avoid formation of dust and aerosols. Further processing of solid materials may result in the formation of combustible dusts. The potential for combustible dust formation should be taken into consideration before additional processing occurs. Provide appropriate exhaust ventilation at places where dust is formed.
Sigma-Aldrich; Safety Data Sheet for Convallatoxin, Product Number: PHL80834, Version 5.0 (Revision Date 09/07/2018). Available from, as of September 11, 2018: https://www.sigmaaldrich.com/safety-center.html
ACCIDENTAL RELEASE MEASURES; Personal precautions, protective equipment and emergency procedures: Wear respiratory protection. Avoid dust formation. Avoid breathing vapors, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust. Environmental precautions: Prevent further leakage or spillage if safe to do so. Do not let product enter drains.
Sigma-Aldrich; Safety Data Sheet for Convallatoxin, Product Number: PHL80834, Version 5.0 (Revision Date 09/07/2018). Available from, as of September 11, 2018: https://www.sigmaaldrich.com/safety-center.html
Avoid contact with skin, eyes and clothing. Wash hands before breaks and immediately after handling the product.
Sigma-Aldrich; Safety Data Sheet for Convallatoxin, Product Number: PHL80834, Version 5.0 (Revision Date 09/07/2018). Available from, as of September 11, 2018: https://www.sigmaaldrich.com/safety-center.html
SRP: Local exhaust ventilation should be applied wherever there is an incidence of point source emissions or dispersion of regulated contaminants in the work area. Ventilation control of the contaminant as close to its point of generation is both the most economical and safest method to minimize personnel exposure to airborne contaminants. Ensure that the local ventilation moves the contaminant away from the worker.

11.4 Handling and Storage

11.4.1 Storage Conditions

Keep container tightly closed in a dry and well-ventilated place. Storage class (TRGS 510): 6.1D: Non-combustible, acute toxic Cat.3 / toxic hazardous materials or hazardous materials causing chronic effects
Sigma-Aldrich; Safety Data Sheet for Convallatoxin, Product Number: PHL80834, Version 5.0 (Revision Date 09/07/2018). Available from, as of September 11, 2018: https://www.sigmaaldrich.com/safety-center.html

11.5 Exposure Control and Personal Protection

11.5.1 Personal Protective Equipment (PPE)

Eye/face protection: Face shield and safety glasses Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU).
Sigma-Aldrich; Safety Data Sheet for Convallatoxin, Product Number: PHL80834, Version 5.0 (Revision Date 09/07/2018). Available from, as of September 11, 2018: https://www.sigmaaldrich.com/safety-center.html
Skin protection: Handle with gloves.
Sigma-Aldrich; Safety Data Sheet for Convallatoxin, Product Number: PHL80834, Version 5.0 (Revision Date 09/07/2018). Available from, as of September 11, 2018: https://www.sigmaaldrich.com/safety-center.html
Body Protection: Complete suit protecting against chemicals. The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace.
Sigma-Aldrich; Safety Data Sheet for Convallatoxin, Product Number: PHL80834, Version 5.0 (Revision Date 09/07/2018). Available from, as of September 11, 2018: https://www.sigmaaldrich.com/safety-center.html
Respiratory protection: Where risk assessment shows air-purifying respirators are appropriate use a full-face particle respirator type N99 (US) or type P2 (EN 143) respirator cartridges as a backup to engineering controls. If the respirator is the sole means of protection, use a full-face supplied air respirator. Use respirators and components tested and approved under appropriate government standards such as NIOSH (US) or CEN (EU).
Sigma-Aldrich; Safety Data Sheet for Convallatoxin, Product Number: PHL80834, Version 5.0 (Revision Date 09/07/2018). Available from, as of September 11, 2018: https://www.sigmaaldrich.com/safety-center.html

11.6 Stability and Reactivity

11.6.1 Hazardous Reactivities and Incompatibilities

Incompatible materials: Strong acids, strong bases, strong oxidizing agents.
Sigma-Aldrich; Safety Data Sheet for Convallatoxin, Product Number: PHL80834, Version 5.0 (Revision Date 09/07/2018). Available from, as of September 11, 2018: https://www.sigmaaldrich.com/safety-center.html

12 Toxicity

12.1 Toxicological Information

12.1.1 Toxicity Summary

IDENTIFICATION AND USE: Convallotoxin is a cardiac glycoside. A phytotoxin from the flowers of Adonis vernalis, Convallaria majalis (Lily of the Valley), Ornthogalum umbellatum and Antiaris toxicaria. The aglycone is convallatoxigenin and the sugar is a rhamnose. Convallatoxin is used in acute and chronic congestive heart-failure and paroxysmal tachycardia. HUMAN STUDIES: Convallotoxin induced cytostatic and cytotoxic effects in human lung A549 cells. Convallotoxin inhibited the Na,K-ATPase in A549 cells at nM concentrations. ANIMAL STUDIES: When administered in a single iv injection at minute to lethal doses to rats or cats, convallatoxin caused vascular disorders in the heart, liver, and kidneys. When injected daily at doses corresponding to 0.2 to 0.4 LD100 for 15 days, it caused dystrophic changes and increased the infiltration and proliferation processes. When injected iv into mice, the LD50 value of convallatoxin was 6.3 mg/kg. The glycoside caused tremor, convulsions, and paralysis of the limbs and affected respiration. The preparation caused disorders in the cardiac activity and a transient coronary insufficiency. The effects of a single or repeated ip injections of convallatoxin on the histology of the heart, liver, kidney, spleen, and lungs was studied in mice, rats, and cats. A single injection dilated blood vessels in the heart, liver, and kidneys, caused hemorrhage in the liver, and caused an infiltrative-proliferative effect in the heart and liver. After chronic injections, the infiltrative-proliferative effect was more pronounced than after the acute administration, and dystrophic changes were observed in the liver. ECOTOXICITY STUDIES: Convallatoxin (20 uM) could significantly prolong the lifespan of wild-type Caenorhabditis elegans up to 16.3% through daf-16, but not sir-2.1 signalling and increased thermotolerance and resistance to paraquat-induced oxidative stress. Convallatoxin also improved pharyngeal pumping, locomotion, reduced lipofuscin accumulation and reactive oxygen species levels in C. elegans, which were attributed to hormesis, free radical-scavenging effects in vivo, and up-regulation of stress resistance-related proteins, such as SOD-3 and HSP-16.1. Furthermore, aging-associated genes daf-16, sod-3, and ctl-2 also appeared to contribute to the stress-resistance effect of convallatoxin.
Convallatoxin (CNT) is classified as a cardiac glycoside. Cardiac glycosides are well known Na+/K+-ATPase inhibitors, and some of them are used to treat congestive heart failure and atrial arrhythmias. Recent studies have reported that cardiac glycosides have potential as anticancer agents. CNT exerts cytotoxic effects on a number of cancer and normal cell lines and induces apoptosis by increasing caspase-3 and poly ADP ribose polymerase (PARP) cleavage. Moreover, dose- and time-dependent autophagic activity was detected in CNT-treated cells, and mammalian target of rapamycin (mTOR)/p70S6K signal pathway inhibition was observed. Notably, CNT inhibits human umbilical vein endothelial cell (HUVEC) growth and exerts anti-angiogenic activity in vitro and in vivo. (A15340)
A15340: Yang SY, Kim NH, Cho YS, Lee H, Kwon HJ: Convallatoxin, a dual inducer of autophagy and apoptosis, inhibits angiogenesis in vitro and in vivo. PLoS One. 2014 Mar 24;9(3):e91094. doi: 10.1371/journal.pone.0091094. eCollection 2014. PMID:24663328

12.1.2 Carcinogen Classification

Carcinogen Classification
No indication of carcinogenicity to humans (not listed by IARC).

12.1.3 Acute Effects

12.1.4 Antidote and Emergency Treatment

/SRP:/ Immediate first aid: Ensure that adequate decontamination has been carried out. If patient is not breathing, start artificial respiration, preferably with a demand valve resuscitator, bag-valve-mask device, or pocket mask, as trained. Perform CPR if necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on left side (head-down position, if possible) to maintain an open airway and prevent aspiration. Keep patient quiet and maintain normal body temperature. Obtain medical attention. /Poisons A and B/
Currance, P.L. Clements, B., Bronstein, A.C. (Eds).; Emergency Care For Hazardous Materials Exposure. 3rd revised edition, Elsevier Mosby, St. Louis, MO 2007, p. 160
/SRP:/ Basic treatment: Establish a patent airway (oropharyngeal or nasopharyngeal airway, if needed). Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if needed. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with 0.9% saline (NS) during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 mL/kg up to 200 mL of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool ... . Cover skin burns with dry sterile dressings after decontamination ... . /Poisons A and B/
Currance, P.L. Clements, B., Bronstein, A.C. (Eds).; Emergency Care For Hazardous Materials Exposure. 3rd revised edition, Elsevier Mosby, St. Louis, MO 2007, p. 160
/SRP:/ Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in severe respiratory distress. Positive-pressure ventilation techniques with a bag valve mask device may be beneficial. Consider drug therapy for pulmonary edema ... . Consider administering a beta agonist such as albuterol for severe bronchospasm ... . Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start IV administration of D5W TKO /SRP: "To keep open", minimal flow rate/. Use 0.9% saline (NS) or lactated Ringer's (LR) if signs of hypovolemia are present. For hypotension with signs of hypovolemia, administer fluid cautiously. Watch for signs of fluid overload ... . Treat seizures with diazepam (Valium) or lorazepam (Ativan) ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Poisons A and B/
Currance, P.L. Clements, B., Bronstein, A.C. (Eds).; Emergency Care For Hazardous Materials Exposure. 3rd revised edition, Elsevier Mosby, St. Louis, MO 2007, p. 160-1

12.1.5 Human Toxicity Excerpts

/ALTERNATIVE and IN VITRO TESTS/ Convallatoxin showed potent cytotoxic activity when assayed against Eagle's KB strain of human epidermoid carcinoma and in a disk-plate assay against kb cells. The results suggested that cytotoxicity is associated with an unsaturated lactone either attached to position 17 by a carbon-carbon bond or fused to ring d across the 16,17-position. Thus, the cardiac principles have either a cardenolide ring or a bufadienolide ring attached to position 17. The data also shows that the glycosides were more active than the corresponding aglycones and that the cardenolide and bufadienolide rings were equally effective in confering activity.
Kelley RB et al; J Med Chem 8 (4): 547 (1965)
/ALTERNATIVE and IN VITRO TESTS/ Cardiac glycosides consist of a large family of naturally derived compounds that are clinically used to treat congestive heart failure, and also present anticancer properties. In this study, the cytotoxic effects of two cardenolides, digitoxigenin monodigitoxoside (DGX) and convallatoxin (CON) were screened in four human tumor cell lines. Both compounds showed anti-proliferative effects in all tumor cells, at nanomolar concentrations. Since the human lung cancer cell line A549 was the most sensitive, we investigated the anti-proliferative, anti-migratory and anti-invasive effects of these cardenolides. DGX and CON reduced A549 cell migration, being able to reduce more than 90% of cell invasion. Their effects on the expression of key regulators of metastatic mechanism showed decreased levels of MMP-2, MMP-9 and p-FAK. Both compounds also presented low toxicity for healthy cells. Finally, this work provides the first insights into the effects of these cardenolides on key steps of lung cancer metastasis.
Schneider NF et al; Nat Prod Res 30 (11): 1327-31 (2016)
/ALTERNATIVE and IN VITRO TESTS/ Autophagy and apoptosis are important processes that control cellular homeostasis and have been highlighted as promising targets for novel cancer therapies. Here, we identified convallatoxin (CNT), isolated from Antiaris toxicaria, as a dual inducer of autophagy and apoptosis. CNT exerts cytotoxic effects on a number of cancer and normal cell lines and induces apoptosis by increasing caspase-3 and poly ADP ribose polymerase (PARP) cleavage. Moreover, dose- and time-dependent autophagic activity was detected in CNT-treated cells, and mammalian target of rapamycin (mTOR)/p70S6K signal pathway inhibition was observed. Notably, CNT inhibits human umbilical vein endothelial cell (HUVEC) growth and exerts anti-angiogenic activity in vitro and in vivo. Collectively, these results demonstrate that the naturally occurring compound, CNT, is a novel anti-angiogenic compound via dual inducing of autophagy and apoptosis.
Yang SY et al; PLoS One 9 (3): e91094 (2014)
/ALTERNATIVE and IN VITRO TESTS/ Cardenolides are cardiac glycosides, mostly obtained from natural sources. They are well known for their inhibitory action on the Na,K-ATPase, an effect that regulates cardiovascular alterations such as congestive heart failure and atrial arrhythmias. In recent years, they have also sparked new interest in their anticancer potential. In the present study, the cytotoxic effects of the natural cardenolide convallatoxin (CON) were evaluated on non-small cell lung cancer (A549) cells. It was found that CON induced cytostatic and cytotoxic effects in A549 cells, showing essentially apoptotic cell death, as detected by annexin V-propidium iodide double-staining, as well as changes in cell form. In addition, it prompted cell cycle arrest in G2/M and reduced cyclin B1 expression. This compound also increased the number of cells in subG1 in a concentration- and time-dependent manner. At a long term, the reduction of cumulative population doubling was shown along with an increase of beta-galactosidase positive cells and larger nucleus, indicative of senescence. Subsequently, CON inhibited the Na,K-ATPase in A549 cells at nM concentrations. Interestingly, at the same concentrations, CON was unable to directly inhibit the Na,K-ATPase, either in pig kidney or in red blood cells. Additionally, results of docking calculations showed that CON binds with high efficiency to the Na,K-ATPase. Taken together, our data highlight the potent anticancer effects of CON in A549 cells, and their possible link with non-classical inhibition of Na,K-ATPase.
Schneider NFZ et al; Mol Cell Biochem 428 (1-2): 23-39 (2017)
/OTHER TOXICITY INFORMATION/ None of the cardiac glycosides tested affected total blood serum calcium levels in patients with cardiac insufficiency, but all increased ionic Ca2+ levels.
Merzon KA, Kolomiets VV; Kardiologiya 19 (10): 110 (1979)

12.1.6 Non-Human Toxicity Excerpts

/LABORATORY ANIMALS: Acute Exposure/ When administered in a single iv injection at minute to lethal doses to rats or cats, convallatoxin caused vascular disorders in the heart, liver, and kidneys. When injected daily at doses corresponding to 0.2 to 0.4 LD100 for 15 days, it caused dystrophic changes and increased the infiltration and proliferation processes.
Belova LF; Mater Vses Konf Issled Lek Rast Perspekt Ikh Ispol'z Proizvod Lek Prep: 12 (1972)
/LABORATORY ANIMALS: Acute Exposure/ The effects of a single or repeated ip injections of convallatoxin on the histology of the heart, liver, kidney, spleen, and lungs was studied in mice, rats, and cats. A single injection dilated blood vessels in the heart, liver, and kidneys, caused hemorrhage in the liver, and caused an infiltrative-proliferative effect in the heart and liver. After chronic injections, the infiltrative-proliferative effect was more pronounced than after the acute administration, and dystrophic changes were observed in the liver.
Belova LF; Tr Vses Nauch-Issled Inst Lek Rast 14: 29 (1971)
/LABORATORY ANIMALS: Acute Exposure/ When injected iv into mice, the LD50 value of convallatoxin was 6.3 mg/kg. The glycoside caused tremor, convulsions, and paralysis of the limbs and affected respiration. The preparation caused disorders in the cardiac activity and a transient coronary insufficiency.
Belova LF, Turova AD; Mater Vses Konf Issled Lek Rast Perspekt Ikh Ispol'z Proizvod Lek Prep: 7 (1972)
/LABORATORY ANIMALS: Neurotoxicity/ Iv injection of convallatoxin at 0.1 mg/kg induced a hyperbaric slow-wave sleep in the cerebral cortex of rabbits. The brain content of 5-hydroxytryptamine did not change markedly. It increased slightly following iv injection of convallatoxin at 0.15 mg/kg. The possible mechanisms of the CNS-inhibitory and central arrhythmic effects of convallatoxin is discussed.
Gu Z et al; Zhongcaoyao 14 (7): 317 (1983)
For more Non-Human Toxicity Excerpts (Complete) data for Convallatoxin (7 total), please visit the HSDB record page.

12.1.7 Non-Human Toxicity Values

LD50 Mice ip 10 mg/kg
Lewis, R.J. Sr. (ed) Sax's Dangerous Properties of Industrial Materials. 11th Edition. Wiley-Interscience, Wiley & Sons, Inc. Hoboken, NJ. 2004., p. 985
LD50 Rat iv 15 mg/kg
Lewis, R.J. Sr. (ed) Sax's Dangerous Properties of Industrial Materials. 11th Edition. Wiley-Interscience, Wiley & Sons, Inc. Hoboken, NJ. 2004., p. 985
LD50 Mice sc 15 mg/kg
Lewis, R.J. Sr. (ed) Sax's Dangerous Properties of Industrial Materials. 11th Edition. Wiley-Interscience, Wiley & Sons, Inc. Hoboken, NJ. 2004., p. 985
LD50 Mice iv 1 mg/kg
Lewis, R.J. Sr. (ed) Sax's Dangerous Properties of Industrial Materials. 11th Edition. Wiley-Interscience, Wiley & Sons, Inc. Hoboken, NJ. 2004., p. 985
For more Non-Human Toxicity Values (Complete) data for Convallatoxin (6 total), please visit the HSDB record page.

12.2 Ecological Information

12.2.1 Natural Pollution Sources

Convallatoxin is found in the blossoms of lily of valley (Convallaria majalis L, Liliaceae), from Ornithogalum umbellatum L, Liliaceae and from Antiaris toxicaria Lesch, Moraceae(1).
(1) O'Neil MJ, ed; The Merck Index. 15th ed., Cambridge, UK: Royal Society of Chemistry, p. 448 (2013)

12.2.2 Plant Concentrations

Convallatoxin was reported in Lilly-of-the-Valley (Convallaria majalis (Lilaceae)(1).
(1) US Dept Agric; US Dept Agric, Agric Res Service. 1992-2018. Dr. Duke's Phytochemical and Ethnobotanical Databases. Convallatoxin. Available from, as of Jan 23, 2019: https://phytochem.nal.usda.gov/phytochem/search

13 Associated Disorders and Diseases

14 Literature

14.1 Consolidated References

14.2 NLM Curated PubMed Citations

14.3 Springer Nature References

14.4 Chemical Co-Occurrences in Literature

14.5 Chemical-Gene Co-Occurrences in Literature

14.6 Chemical-Disease Co-Occurrences in Literature

15 Patents

15.1 Depositor-Supplied Patent Identifiers

15.2 WIPO PATENTSCOPE

15.3 Chemical Co-Occurrences in Patents

15.4 Chemical-Disease Co-Occurrences in Patents

15.5 Chemical-Gene Co-Occurrences in Patents

16 Interactions and Pathways

16.1 Chemical-Target Interactions

17 Biological Test Results

17.1 BioAssay Results

18 Taxonomy

The LOTUS Initiative for Open Natural Products Research: frozen dataset union wikidata (with metadata) | DOI:10.5281/zenodo.5794106
S29 | PHYTOTOXINS | Toxic Plant Phytotoxin (TPPT) Database | DOI:10.5281/zenodo.2652993

19 Classification

19.1 MeSH Tree

19.2 ChEBI Ontology

19.3 LIPID MAPS Classification

19.4 KEGG: Lipid

19.5 KEGG: Phytochemical Compounds

19.6 KEGG: Natural Toxins

19.7 KEGG : Glycosides

19.8 ChemIDplus

19.9 ChEMBL Target Tree

19.10 UN GHS Classification

19.11 NORMAN Suspect List Exchange Classification

19.12 CCSBase Classification

19.13 EPA DSSTox Classification

19.14 LOTUS Tree

19.15 MolGenie Organic Chemistry Ontology

20 Information Sources

  1. CAS Common Chemistry
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    https://creativecommons.org/licenses/by-nc/4.0/
  2. ChemIDplus
    ChemIDplus Chemical Information Classification
    https://pubchem.ncbi.nlm.nih.gov/source/ChemIDplus
  3. EPA DSSTox
    CompTox Chemicals Dashboard Chemical Lists
    https://comptox.epa.gov/dashboard/chemical-lists/
  4. European Chemicals Agency (ECHA)
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    https://echa.europa.eu/web/guest/legal-notice
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    https://www.fda.gov/about-fda/about-website/website-policies#linking
  6. Hazardous Substances Data Bank (HSDB)
  7. CCSbase
    CCSbase Classification
    https://ccsbase.net/
  8. ChEBI
  9. LOTUS - the natural products occurrence database
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    The code for LOTUS is released under the GNU General Public License v3.0.
    https://lotus.nprod.net/
  10. Toxin and Toxin Target Database (T3DB)
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    http://www.t3db.ca/downloads
  11. ChEMBL
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    http://www.ebi.ac.uk/Information/termsofuse.html
  12. Comparative Toxicogenomics Database (CTD)
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    http://ctdbase.org/about/legal.jsp
  13. Haz-Map, Information on Hazardous Chemicals and Occupational Diseases
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    https://haz-map.com/About
  14. Japan Chemical Substance Dictionary (Nikkaji)
  15. KEGG
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    https://www.kegg.jp/kegg/legal.html
  16. LIPID MAPS
    Lipid Classification
    https://www.lipidmaps.org/
  17. Natural Product Activity and Species Source (NPASS)
  18. NORMAN Suspect List Exchange
    LICENSE
    Data: CC-BY 4.0; Code (hosted by ECI, LCSB): Artistic-2.0
    https://creativecommons.org/licenses/by/4.0/
    Convallatoxin
    NORMAN Suspect List Exchange Classification
    https://www.norman-network.com/nds/SLE/
  19. MassBank of North America (MoNA)
    LICENSE
    The content of the MoNA database is licensed under CC BY 4.0.
    https://mona.fiehnlab.ucdavis.edu/documentation/license
  20. Metabolomics Workbench
  21. SpectraBase
  22. Springer Nature
  23. Therapeutic Target Database (TTD)
  24. Wikidata
  25. Wikipedia
  26. PubChem
  27. Medical Subject Headings (MeSH)
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    https://www.nlm.nih.gov/copyright.html
  28. GHS Classification (UNECE)
  29. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
  30. PATENTSCOPE (WIPO)
CONTENTS