Compounds > 4'-demethylpodophyllotoxin
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4'-demethylpodophyllotoxin

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Description

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. [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]

Cross-References

ID SourceID
PubMed CID122667
CHEMBL ID28941
CHEBI ID1730
SCHEMBL ID12278154

Synonyms (33)

Synonym
furo(3',4':6,7)naphtho(2,3-d)-1,3-dioxol-6(5ah)-one, 5,8,8a,9-tetrahydro-9-hydroxy-5-(4-hydroxy-3,5-dimethoxyphenyl)-, (5r-(5-alpha,5a-beta,8a-alpha,9-alpha))-
brn 0099005
5,8,8a,9,-tetrahydro-9-hydroxy-5-(4-hydroxy-3,5-dimethoxyphenyl)furo[3',4':6,7]naphtho[2,3-d]-1,3-dioxol-6(5ah)-one
(5r,5ar,8ar,9r)-5-hydroxy-9-(4-hydroxy-3,5-dimethoxy-phenyl)-5a,6,8a,9-tetrahydro-5h-isobenzofuro[6,5-f][1,3]benzodioxol-8-one
4'-demethylpodophyllotoxin
40505-27-9
4-demethyl-podophyllotoxin
CHEMBL28941
chebi:1730 ,
4'-demethyl-podophyllotoxin
(5r,5ar,8ar,9r)-5-hydroxy-9-(4-hydroxy-3,5-dimethoxyphenyl)-5a,6,8a,9-tetrahydro-5h-[2]benzofuro[5,6-f][1,3]benzodioxol-8-one
S3908
unii-7n5e50463v
7n5e50463v ,
(5r,5ar,8ar,9r)-9-hydroxy-5-(4-hydroxy-3,5-dimethoxyphenyl)-5,5a,8a,9-tetrahydrofuro[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6(8h)-one
4'-o-demethylpodophyllotoxin
o(4')-demethylpodophyllotoxin
(5r,5ar,8ar,9r)-9-hydroxy-5-(4-hydroxy-3,5-dimethoxyphenyl)-5,8,8a,9-tetrahydrofuro[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6(5ah)-one
AKOS015895546
4-demethylpodophyllotoxin
furo(3',4':6,7)naphtho(2,3-d)-1,3-dioxol-6(5ah)-one, 5,8,8a,9-tetrahydro-9-hydroxy-5-(4-hydroxy-3,5-dimethoxyphenyl)-, (5r,5ar,8ar,9r)-
SCHEMBL12278154
AC-34637
FD10224
J-515253
AS-58706
mfcd01725607
Q27105499
HY-N2323
CS-0020771
CCG-268651
DTXSID201311785
PD088390
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (1)

RoleDescription
metaboliteAny intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
[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 (3)

ClassDescription
furonaphthodioxole
organic heterotetracyclic compound
phenolsOrganic aromatic compounds having one or more hydroxy groups attached to a benzene or other arene ring.
[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]

Protein Targets (1)

Other Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
DNA topoisomerase 2-alphaHomo sapiens (human)ID50100.00005.00007.500010.0000AID335667
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (16)

Processvia Protein(s)Taxonomy
hematopoietic progenitor cell differentiationDNA topoisomerase 2-alphaHomo sapiens (human)
DNA topological changeDNA topoisomerase 2-alphaHomo sapiens (human)
DNA ligationDNA topoisomerase 2-alphaHomo sapiens (human)
DNA damage responseDNA topoisomerase 2-alphaHomo sapiens (human)
chromosome segregationDNA topoisomerase 2-alphaHomo sapiens (human)
female meiotic nuclear divisionDNA topoisomerase 2-alphaHomo sapiens (human)
apoptotic chromosome condensationDNA topoisomerase 2-alphaHomo sapiens (human)
embryonic cleavageDNA topoisomerase 2-alphaHomo sapiens (human)
regulation of circadian rhythmDNA topoisomerase 2-alphaHomo sapiens (human)
positive regulation of apoptotic processDNA topoisomerase 2-alphaHomo sapiens (human)
positive regulation of single stranded viral RNA replication via double stranded DNA intermediateDNA topoisomerase 2-alphaHomo sapiens (human)
positive regulation of transcription by RNA polymerase IIDNA topoisomerase 2-alphaHomo sapiens (human)
rhythmic processDNA topoisomerase 2-alphaHomo sapiens (human)
negative regulation of DNA duplex unwindingDNA topoisomerase 2-alphaHomo sapiens (human)
resolution of meiotic recombination intermediatesDNA topoisomerase 2-alphaHomo sapiens (human)
sister chromatid segregationDNA topoisomerase 2-alphaHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (13)

Processvia Protein(s)Taxonomy
magnesium ion bindingDNA topoisomerase 2-alphaHomo sapiens (human)
DNA bindingDNA topoisomerase 2-alphaHomo sapiens (human)
chromatin bindingDNA topoisomerase 2-alphaHomo sapiens (human)
RNA bindingDNA topoisomerase 2-alphaHomo sapiens (human)
DNA topoisomerase type II (double strand cut, ATP-hydrolyzing) activityDNA topoisomerase 2-alphaHomo sapiens (human)
protein kinase C bindingDNA topoisomerase 2-alphaHomo sapiens (human)
protein bindingDNA topoisomerase 2-alphaHomo sapiens (human)
ATP bindingDNA topoisomerase 2-alphaHomo sapiens (human)
ATP-dependent activity, acting on DNADNA topoisomerase 2-alphaHomo sapiens (human)
DNA binding, bendingDNA topoisomerase 2-alphaHomo sapiens (human)
protein homodimerization activityDNA topoisomerase 2-alphaHomo sapiens (human)
ubiquitin bindingDNA topoisomerase 2-alphaHomo sapiens (human)
protein heterodimerization activityDNA topoisomerase 2-alphaHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (12)

Processvia Protein(s)Taxonomy
nucleolusDNA topoisomerase 2-alphaHomo sapiens (human)
nuclear chromosomeDNA topoisomerase 2-alphaHomo sapiens (human)
centrioleDNA topoisomerase 2-alphaHomo sapiens (human)
chromosome, centromeric regionDNA topoisomerase 2-alphaHomo sapiens (human)
condensed chromosomeDNA topoisomerase 2-alphaHomo sapiens (human)
male germ cell nucleusDNA topoisomerase 2-alphaHomo sapiens (human)
nucleusDNA topoisomerase 2-alphaHomo sapiens (human)
nucleoplasmDNA topoisomerase 2-alphaHomo sapiens (human)
nucleolusDNA topoisomerase 2-alphaHomo sapiens (human)
cytoplasmDNA topoisomerase 2-alphaHomo sapiens (human)
DNA topoisomerase type II (double strand cut, ATP-hydrolyzing) complexDNA topoisomerase 2-alphaHomo sapiens (human)
protein-containing complexDNA topoisomerase 2-alphaHomo sapiens (human)
ribonucleoprotein complexDNA topoisomerase 2-alphaHomo sapiens (human)
nucleusDNA topoisomerase 2-alphaHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (19)

Assay IDTitleYearJournalArticle
AID598808Cytotoxicity against human KB cells after 72 hrs by MTT assay2011Bioorganic & medicinal chemistry letters, Jun-15, Volume: 21, Issue:12
Three new cytotoxic aryltetralin lignans from Sinopodophyllum emodi.
AID404065Antiviral activity against HSV1 infected in human primary amnion cells assessed as inhibition of virus-induced pathogenic effect1998Journal of natural products, Nov, Volume: 61, Issue:11
Antiviral activity of lignans.
AID335669Inhibition of strand rejoining activity of human DNA topoisomerase 2 assessed as protein-DNA complex formation at 10 uM by cell-based assay1992Journal of natural products, Aug, Volume: 55, Issue:8
Antitumor agents, 130, Novel 4 beta-arylamino derivatives of 3',4'-didemethoxy-3',4'-dioxo-4-deoxypodophyllotoxin as potent inhibitors of human DNA topoisomerase II.
AID355595Inhibition of DNA topoisomerase 2 in human KB cells assessed as enzyme-[methyl-3H]thymidine-labeled DNA complex formation at 10 uM after 1 hr by K-SDS precipitation assay
AID211458Compound tested for ability to form a cellular covalent topoisomerase II-DNA complex.1996Journal of medicinal chemistry, Mar-29, Volume: 39, Issue:7
Antitumor agents. 163. Three-dimensional quantitative structure-activity relationship study of 4'-O-demethylepipodophyllotoxin analogs using the modified CoMFA/q2-GRS approach.
AID355594Cytotoxicity against human KB cells assessed as reduction in cell number after 3 days by crystal violet staining
AID277523Cytotoxicity against androgen-independent human PC3 cells2007Journal of natural products, Feb, Volume: 70, Issue:2
Lignans from Dysosma versipellis with inhibitory effects on prostate cancer cell lines.
AID598807Cytotoxicity against human HeLa cells after 72 hrs by MTT assay2011Bioorganic & medicinal chemistry letters, Jun-15, Volume: 21, Issue:12
Three new cytotoxic aryltetralin lignans from Sinopodophyllum emodi.
AID355592Inhibition of human DNA topoisomerase 2 assessed as bacteriophage P4 DNA unknotting at 100 uM after 30 mins by agarose gel electrophoresis
AID73178Cytotoxic effect against GLC4 (human small cell lung carcinoma cell line) using the microculture tetrazolium (MTT) assay based on continuous incubation1995Journal of medicinal chemistry, Jun-09, Volume: 38, Issue:12
Synthesis and cytotoxicity of novel lignans.
AID91560Inhibitory activity against strand transfer by HIV-1 Integrase at 100 uM1996Journal of medicinal chemistry, Jan-05, Volume: 39, Issue:1
(-)-Arctigenin as a lead structure for inhibitors of human immunodeficiency virus type-1 integrase.
AID73177Cytotoxic effect against GLC4 (human small cell lung carcinoma cell line) using the microculture tetrazolium (MTT) assay based on 2 hr incubation1995Journal of medicinal chemistry, Jun-09, Volume: 38, Issue:12
Synthesis and cytotoxicity of novel lignans.
AID277522Cytotoxicity against androgen sensitive human LNCaP cells2007Journal of natural products, Feb, Volume: 70, Issue:2
Lignans from Dysosma versipellis with inhibitory effects on prostate cancer cell lines.
AID91438Inhibitory activity against 3'-processing by HIV-1 Integrase at 100 uM1996Journal of medicinal chemistry, Jan-05, Volume: 39, Issue:1
(-)-Arctigenin as a lead structure for inhibitors of human immunodeficiency virus type-1 integrase.
AID404066Cytotoxicity against human primary amnion cells assessed as morphological changes by microscopic examination1998Journal of natural products, Nov, Volume: 61, Issue:11
Antiviral activity of lignans.
AID403993Antiviral activity against HSV1 infected in monkey CV-1 cells assessed as inhibition of plaque formation1998Journal of natural products, Nov, Volume: 61, Issue:11
Antiviral activity of lignans.
AID335667Inhibition of human DNA topoisomerase 21992Journal of natural products, Aug, Volume: 55, Issue:8
Antitumor agents, 130, Novel 4 beta-arylamino derivatives of 3',4'-didemethoxy-3',4'-dioxo-4-deoxypodophyllotoxin as potent inhibitors of human DNA topoisomerase II.
AID403984Therapeutic index, ratio of MTC for human primary amnion cells to lowest drug level causing inhibition of HSV11998Journal of natural products, Nov, Volume: 61, Issue:11
Antiviral activity of lignans.
AID403994Antiviral activity against VSV infected in BHK cells assessed as inhibition of plaque formation1998Journal of natural products, Nov, Volume: 61, Issue:11
Antiviral activity of lignans.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (7)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's5 (71.43)18.2507
2000's1 (14.29)29.6817
2010's1 (14.29)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: 12.17

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.

MetricThis Compound (vs All)
Research Demand Index12.17 (24.57)
Research Supply Index2.20 (2.92)
Research Growth Index4.36 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.17)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews1 (12.50%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other7 (87.50%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
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.		4.0340furonaphthodioxole;
lignan;
organic heterotetracyclic compound		antimitotic;
antineoplastic agent;
keratolytic drug;
microtubule-destabilising agent;
plant metabolite;
tubulin modulator
etoposide
[no description available]		4.1950beta-D-glucoside;
furonaphthodioxole;
organic heterotetracyclic compound		antineoplastic agent;
DNA synthesis inhibitor
arctigenin
arctigenin: precursor to catechols; in many plants		3.4920lignan
secoisolariciresinol
secoisolariciresinol: RN given refers to ((R-(R*,R*))-isomer); RN for cpd without isomeric designation not available 8/89; precursor of lignans found in human urine; structure given in first source. secoisolariciresinol : A lignan that is butane-1,4-diol in which the 2 and 3 positions are substituted by 4-hydroxy-3-methoxybenzyl groups. (-)-secoisolariciresinol : An enantiomer of secoisolariciresinol having (-)-(2R,3R)-configuration.		1.9910secoisolariciresinolantidepressant;
phytoestrogen;
plant metabolite
picropodophyllin
picropodophyllin: isolated from American May apple (Podophyllum); inhibits IGF-I autophosphorylation without interfering with tyrosine kinase activity. picropodophyllotoxin : An organic heterotetracyclic compound that has a furonaphthodioxole skeleton bearing 3,4,5-trimethoxyphenyl and hydroxy substituents.		3.0910furonaphthodioxole;
lignan;
organic heterotetracyclic compound		antineoplastic agent;
insulin-like growth factor receptor 1 antagonist;
plant metabolite;
tyrosine kinase inhibitor
beta-peltatin
beta-peltatin : An organic heterotetracyclic compound that is alpha-peltatin in which the phenolic hydroxy group of the 4-hydroxy-3,5-dimethoxyphenyl substitutent had been converted into the corresponding methyl ether.		3.4920furonaphthodioxole;
gamma-lactone;
lignan;
organic heterotetracyclic compound;
phenols		antineoplastic agent;
plant metabolite
alpha-peltatin
alpha-peltatin: RN given for (5R-(5alpha,5beta,8aalpha))-isomer. alpha-peltatin : An organic heterotetracyclic compound that is 4'-demethylpodophyllotoxin which is substituted by a hydroxy group at position 10 but which is lacking the hydroxy group at position 9. It is found as a glucoside in the rhizomes of Podophyllum peltatum.		3.4920furonaphthodioxole;
gamma-lactone;
lignan;
organic heterotetracyclic compound;
phenols		antineoplastic agent;
metabolite
diphyllin
diphyllin: extract of Cleistanthus collinus (Roxb), a highly poisonous plant; do not confuse with diphyllin or diphylline which is the main heading AMINOPHYLLINE; do not confuse with the theophylline derivative DYPHYLLINE		3.5120lignan
epipodophyllotoxin
[no description available]		3.0910
matairesinol
matairesinol: lignan that is a central precursor in plants in the biosynthesis of numerous lignans (coordinate with specific); RN refers to (3R-trans)-isomer. (-)-matairesinol : A lignan that is gamma-butyrolactone in which the 3 and 4 positions are substituted by 4-hydroxy-3-methoxybenzyl groups (the 3R,4R-diastereomer).		1.9910gamma-lactone;
lignan;
polyphenol		angiogenesis inhibitor;
anti-asthmatic agent;
phytoestrogen;
plant metabolite
4'-demethylepipodophyllotoxin
4'-demethylepipodophyllotoxin: structure in first source. 4'-demethylepipodophyllotoxin : An organic heterotetracyclic compound that is the 9- epimer of 4'-demethylpodophyllotoxin.		3.7830furonaphthodioxole;
organic heterotetracyclic compound;
phenols		antineoplastic agent
npf-etoposide
NPF-etoposide: RN given refers to (5R-(5alpha,5abeta,8aalpha,9beta))-isomer; structure in first source		2.3920
gl 331
GL 331: structure in first source		2.3920
beta-peltatin a methyl ether
beta-peltatin A methyl ether: isolated from Mexican plant Bursera fagaroides; antitumor agent of podophyllotoxin (III) class; RN given refers to (5alpha,5beta,8aalpha)-isomer		3.0910lactone;
lignan
justicidin a
justicidins: from Justica procumbens		3.0910lignan
4'-demethyldesoxypodophyllotoxin
4'-demethyldesoxypodophyllotoxin: from the root of Bursera tonkinensis Guillaum; structure in first source. 4'-demethyldeoxypodophyllotoxin : 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 4-hydroxy-3,5-dimethoxyphenyl group.		2.4520furonaphthodioxole;
gamma-lactone;
lignan;
methoxybenzenes;
phenols		antineoplastic agent;
antioxidant;
immunosuppressive agent;
plant 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.		2.4220
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).		1.9810aromatic ether;
benzodioxoles;
butan-4-olide;
lignan;
phenols		plant metabolite
rubschisandrin
rubschisandrin: isolated from kernels of Schisandra rubriflora; structure given in first source		3.0910tannin
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.		4.0340furonaphthodioxole;
gamma-lactone;
lignan;
methoxybenzenes		antineoplastic agent;
apoptosis inducer;
plant metabolite
schizandrin c
schizandrin C: from Schizandra chinensis Baill & Fructus schisandrae; protects liver from carbon tetrachloride injury;		3.0910tannin
teniposide
[no description available]		1.9810aromatic 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
trachelogenin
trachelogenin: structure in first source		3.0910lignan
retrojusticidin b
retrojusticidin B: isolated from Phyllanthus myrtifolius; structure in first source		3.0910
gomisin j
gomisin J: a lignan from Schizandra fruits		3.0910
5-methoxypodophyllotoxin
5-methoxypodophyllotoxin: from root culture of Linum flavum; structure given in first source		1.9810furonaphthodioxole
gomisin-g
[no description available]		3.0910
ConditionIndicatedRelationship StrengthStudiesTrials
Carcinoma, Oat Cell
[description not available]		01.9810
Cancer of Lung
[description not available]		01.9810
Lung Neoplasms
Tumors or cancer of the LUNG.		01.9810
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)		01.9810
Cancer of Prostate
[description not available]		02.0310
Prostatic Neoplasms
Tumors or cancer of the PROSTATE.		02.0310