Compounds > 5-methoxypodophyllotoxin

Page last updated: 2024-12-10

5-methoxypodophyllotoxin

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

Description

5-methoxypodophyllotoxin: from root culture of Linum flavum; structure given in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Flora	Rank	Flora Definition	Family	Family Definition
Linum	genus	[no description available]	Linaceae	A plant family in the order Linales. These plants have simple leaves and regular flowers housing a compound ovary. Stamens are usually fused by their filaments.[MeSH]

Cross-References

ID Source	ID
PubMed CID	3035544
CHEMBL ID	292945
CHEBI ID	188507
MeSH ID	M0202191

Synonyms (12)

Synonym
5-methoxypodophyllotoxin
6-methoxypodophyllotoxin
CHEMBL292945
5-methoxy podophyllotoxin
(5r,5ar,8ar,9r)-5-hydroxy-4-methoxy-9-(3,4,5-trimethoxyphenyl)-5a,6,8a,9-tetrahydro-5h-[2]benzofuro[6,5-f][1,3]benzodioxol-8-one
CHEBI:188507
(5r,5ar,8ar,9r)-5-hydroxy-4-methoxy-9-(3,4,5-trimethoxyphenyl)-5a,6,8a,9-tetrahydro-5h-[2]benzouro[6,5-][1,3]benzodioxol-8-one
128443-52-7
(5r-(5alpha,5abeta,8aalpha,9alpha))-5,8,8a,9-tetrahydro-9-hydroxy-10-methoxy-5-(3,4,5-trimethoxyphenyl)furo(3',4':6,7)naphtho(2,3-d)-1,3-dioxol-6(5ah)-one
furo(3',4':6,7)naphtho(2,3-d)-1,3-dioxol-6(5ah)-one, 5,8,8a,9-tetrahydro-9-hydroxy-10-methoxy-5-(3,4,5-trimethoxyphenyl)-, (5r-(5alpha,5abeta,8aalpha,9alpha))-
DTXSID00155903
Q63398578

[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

Class	Description
furonaphthodioxole
[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]

Pathways (2)

Pathway	Proteins	Compounds
podophyllotoxin glucosides metabolism	0	14
6-methoxypodophyllotoxin biosynthesis	0	14
podophyllotoxin glucosides metabolism	0	17

Bioassays (6)

Assay ID	Title	Year	Journal	Article
AID311265	Cytotoxicity against human KB cells by microculture tetrazolium assay	2007	Journal of natural products, Aug, Volume: 70, Issue:8	Sesquiterpenoids and cytotoxic lignans from the bark of Libocedrus chevalieri.
AID73177	Cytotoxic effect against GLC4 (human small cell lung carcinoma cell line) using the microculture tetrazolium (MTT) assay based on 2 hr incubation	1995	Journal of medicinal chemistry, Jun-09, Volume: 38, Issue:12	Synthesis and cytotoxicity of novel lignans.
AID338804	Cytotoxicity against mouse EAT cells after 4 days by trypan blue assay	1992	Journal of natural products, Jan, Volume: 55, Issue:1	Isolation, purification, and cytotoxicity of 5-methoxypodophyllotoxin, a lignan from a root culture of Linum flavum.
AID311266	Inhibition of tubulin polymerization	2007	Journal of natural products, Aug, Volume: 70, Issue:8	Sesquiterpenoids and cytotoxic lignans from the bark of Libocedrus chevalieri.
AID338805	Cytotoxicity against human HeLa cells after 4 days by trypan blue assay	1992	Journal of natural products, Jan, Volume: 55, Issue:1	Isolation, purification, and cytotoxicity of 5-methoxypodophyllotoxin, a lignan from a root culture of Linum flavum.
AID73178	Cytotoxic effect against GLC4 (human small cell lung carcinoma cell line) using the microculture tetrazolium (MTT) assay based on continuous incubation	1995	Journal of medicinal chemistry, Jun-09, Volume: 38, Issue:12	Synthesis and cytotoxicity of novel lignans.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (9)

Timeframe	Studies, This Drug (%)	All Drugs %
pre-1990	0 (0.00)	18.7374
1990's	2 (22.22)	18.2507
2000's	6 (66.67)	29.6817
2010's	1 (11.11)	24.3611
2020's	0 (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: 12.14

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

Metric	This Compound (vs All)
Research Demand Index	12.14 (24.57)
Research Supply Index	2.48 (2.92)
Research Growth Index	4.63 (4.65)
Search Engine Demand Index	0.00 (26.88)
Search Engine Supply Index	0.00 (0.95)

This Compound (12.14)

All Compounds (24.57)

Study Types

Publication Type	This drug (%)	All Drugs (%)
Trials	0 (0.00%)	5.53%
Reviews	0 (0.00%)	6.00%
Case Studies	0 (0.00%)	4.05%
Observational	0 (0.00%)	0.25%
Other	11 (100.00%)	84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Substance	Relationship Strength	Studies	Trials	Classes	Roles
cyclopentane Cyclopentanes: A group of alicyclic hydrocarbons with the general formula R-C5H9.. cyclopentanes : Cyclopentane and its derivatives formed by substitution.	2.02	1	0	cycloalkane; cyclopentanes; volatile organic compound	non-polar solvent
podophyllotoxin Podophyllum: A genus of poisonous American herbs, family BERBERIDACEAE. The roots yield PODOPHYLLOTOXIN and other pharmacologically important agents. The plant was formerly used as a cholagogue and cathartic. It is different from the European mandrake, MANDRAGORA.	8.52	8	0	furonaphthodioxole; lignan; organic heterotetracyclic compound	antimitotic; antineoplastic agent; keratolytic drug; microtubule-destabilising agent; plant metabolite; tubulin modulator
phenyl acetate phenyl acetate: The ester formed between phenol and acetic acid. Don't confuse with phenylacetic acid derivatives listed under PHENYLACETATES.. phenyl acetate : An acetate ester obtained by the formal condensation of phenol with acetic acid.	2.02	1	0	benzenes; phenyl acetates
etoposide [no description available]	2.39	2	0	beta-D-glucoside; furonaphthodioxole; organic heterotetracyclic compound	antineoplastic agent; DNA synthesis inhibitor
4'-demethylpodophyllotoxin 4'-demethylpodophyllotoxin : An organic heterotetracyclic compound that is podophyllotoxin in which the methyl ether group at position 4 of the trimethoxyphenyl group has been cleaved to afford the corresponding phenol.	1.98	1	0	furonaphthodioxole; organic heterotetracyclic compound; phenols	metabolite
prostaglandins b Prostaglandins B: Physiologically active prostaglandins found in many tissues and organs. They are potent pressor substances and have many other physiological activities.	2.39	2	0
pluviatolide pluviatolide: structure. (-)-pluviatolide : A butan-4-olide that is dihydrofuran-2(3H)-one which is substituted by a vanillyl group at position 3 and by a 3,4-methylenedioxybenzyl group at position 4 (the R,R stereoisomer).	1.98	1	0	aromatic ether; benzodioxoles; butan-4-olide; lignan; phenols	plant metabolite
anthricin anthricin: antitumor constituent from Anthriscus sylvestris (L.) Hoffm; structure in first source. deoxypodophyllotoxin : A member of the class of furonaphthodioxoles that is (5R,5aR,8aR)-5,8,8a,9-tetrahydro-2H-furo[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6(5aH)-one substituted at position 5 by a 3,4,5-trimethoxyphenyl group.	2.43	2	0	furonaphthodioxole; gamma-lactone; lignan; methoxybenzenes	antineoplastic agent; apoptosis inducer; plant metabolite
lignans Lignans: A class of dibenzylbutane derivatives which occurs in higher plants and in fluids (bile, serum, urine, etc.) in man and other animals. These compounds, which have a potential anti-cancer role, can be synthesized in vitro by human fecal flora. (From Singleton & Sainsbury, Dictionary of Microbiology and Molecular Biology, 2d ed)	2.96	4	0
teniposide [no description available]	2.39	2	0	aromatic ether; beta-D-glucoside; cyclic acetal; furonaphthodioxole; gamma-lactone; monosaccharide derivative; phenols; thiophenes	antineoplastic agent; EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor
methyl jasmonate [no description available]	2.02	1	0

Condition	Indicated	Relationship Strength	Studies	Trials
Carcinoma, Ehrlich Tumor A transplantable, poorly differentiated malignant tumor which appeared originally as a spontaneous breast carcinoma in a mouse. It grows in both solid and ascitic forms.	0	1.98	1	0
Carcinoma, Oat Cell [description not available]	0	1.98	1	0
Cancer of Lung [description not available]	0	1.98	1	0
Lung Neoplasms Tumors or cancer of the LUNG.	0	1.98	1	0
Carcinoma, Small Cell An anaplastic, highly malignant, and usually bronchogenic carcinoma composed of small ovoid cells with scanty neoplasm. It is characterized by a dominant, deeply basophilic nucleus, and absent or indistinct nucleoli. (From Stedman, 25th ed; Holland et al., Cancer Medicine, 3d ed, p1286-7)	0	1.98	1	0