podophyllotoxin (CHEBI:50305)

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CHEBI:50305 - podophyllotoxin

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ChEBI Name	podophyllotoxin

ChEBI ID	CHEBI:50305

Definition	An organic heterotetracyclic compound that has a furonaphthodioxole skeleton bearing a 3,4,5-trimethoxyphenyl substituent. It is found in the roots and rhizomes of Podophyllum species and is used for the topical treatment of genital warts.

Stars	This entity has been manually annotated by the ChEBI Team.

Secondary ChEBI IDs	CHEBI:45070, CHEBI:8280

Supplier Information	ChemicalBook:CB1147810, eMolecules:29541903, eMolecules:531049, ZINC000003861806

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Wikipedia	License
Podophyllotoxin (PPT) is the active ingredient in Podofilox, a medical cream used to treat genital warts and molluscum contagiosum. It is not recommended for HPV infections without external warts. It can be applied either by a healthcare provider or the patient themselves. Podophyllotoxin is a non-alkaloid lignin extracted from the roots and rhizomes of plants of the genus Podophyllum. A less refined form known as podophyllum resin is also available, but has greater side effects. Podophyllotoxin was first isolated in pure form in 1880 by Valerian Podwyssotzki (1818 – 28 January 1892), a Polish-Russian privatdozent at the University of Dorpat (now Tartu, Estonia) and assistant at the Pharmacological Institute there. PPT is on the World Health Organization's List of Essential Medicines.
Read full article at Wikipedia

Formula

C22H22O8

Net Charge

Average Mass

414.40530

Monoisotopic Mass

414.13147

InChI

InChI=1S/C22H22O8/c1-25-16-4-10(5-17(26-2)21(16)27-3)18-11-6-14-15(30-9-29-14)7-12(11)20(23)13-8-28-22(24)19(13)18/h4-7,13,18-20,23H,8-9H2,1-3H3/t13-,18+,19-,20-/m0/s1

InChIKey

YJGVMLPVUAXIQN-XVVDYKMHSA-N

SMILES

[H][C@]12COC(=O)[C@]1([H])[C@H](c1cc(OC)c(OC)c(OC)c1)c1cc3OCOc3cc1[C@@H]2O

Roles Classification
Biological Role(s):	tubulin modulator Any substance that interacts with tubulin to inhibit or promote polymerisation of microtubules. plant metabolite Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms. microtubule-destabilising agent Any substance that interacts with tubulin to inhibit polymerisation of microtubules. antimitotic Any compound that inhibits cell division (mitosis).

Application(s):	antineoplastic agent A substance that inhibits or prevents the proliferation of neoplasms. keratolytic drug A drug that softens, separates, and causes desquamation of the cornified epithelium or horny layer of skin. Keratolytic drugs are used to expose mycelia of infecting fungi or to treat corns, warts, and certain other skin diseases.

View more via ChEBI Ontology

ChEBI Ontology
Outgoing	podophyllotoxin (CHEBI:50305) has role antimitotic (CHEBI:64911) podophyllotoxin (CHEBI:50305) has role antineoplastic agent (CHEBI:35610) podophyllotoxin (CHEBI:50305) has role keratolytic drug (CHEBI:50176) podophyllotoxin (CHEBI:50305) has role microtubule-destabilising agent (CHEBI:61951) podophyllotoxin (CHEBI:50305) has role plant metabolite (CHEBI:76924) podophyllotoxin (CHEBI:50305) has role tubulin modulator (CHEBI:60832) podophyllotoxin (CHEBI:50305) is a furonaphthodioxole (CHEBI:50307) podophyllotoxin (CHEBI:50305) is a lignan (CHEBI:25036) podophyllotoxin (CHEBI:50305) is a organic heterotetracyclic compound (CHEBI:38163)

Incoming	etoposide (CHEBI:4911) has functional parent podophyllotoxin (CHEBI:50305) teniposide (CHEBI:75988) has functional parent podophyllotoxin (CHEBI:50305)

IUPAC Name

(5R,5aR,8aR,9R)-9-hydroxy-5-(3,4,5-trimethoxyphenyl)-5,8,8a,9-tetrahydrofuro[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6(5aH)-one

Synonyms	Sources
(−)-podophyllotoxin	ChEBI
9-HYDROXY-5-(3,4,5-TRIMETHOXYPHENYL)-5,8,8A,9-TETRAHYDROFURO[3',4':6,7]NAPHTHO[2,3-D][1,3]DIOXOL-6(5AH)-ONE	PDBeChem
Podofilox	ChemIDplus
Podophyllinic acid lactone	ChemIDplus
Podophyllotoxin	KEGG COMPOUND
PPT	ChEBI

Brand Names	Sources
Condylox	KEGG DRUG
Podophyllotoxin 7	DrugBank

Manual Xrefs	Databases
3481	DrugCentral
C00000610	KNApSAcK
C10874	KEGG COMPOUND
D05529	KEGG DRUG
DB01179	DrugBank
HMDB0031452	HMDB
LSM-3055	LINCS
POD	PDBeChem
Podophyllotoxin	Wikipedia
View more database links

Registry Numbers	Types	Sources
518-28-5	CAS Registry Number	KEGG COMPOUND
518-28-5	CAS Registry Number	ChemIDplus
99163	Reaxys Registry Number	Reaxys

Citations

Velóz RA, Cardoso-Taketa A, Villarreal ML (2013)
Production of podophyllotoxin from roots and plantlets of Hyptis suaveolens cultivated in vitro.
Pharmacognosy research 5, 93-102 [PubMed:23798883]
[show Abstract]

Marques JV, Kim KW, Lee C, Costa MA, May GD, Crow JA, Davin LB, Lewis NG (2013)
Next generation sequencing in predicting gene function in podophyllotoxin biosynthesis.
The Journal of biological chemistry 288, 466-479 [PubMed:23161544]
[show Abstract]

Bhattacharyya D, Sinha R, Ghanta S, Chakraborty A, Hazra S, Chattopadhyay S (2012)
Proteins differentially expressed in elicited cell suspension culture of Podophyllum hexandrum with enhanced podophyllotoxin content.
Proteome science 10, 34 [PubMed:22621772]
[show Abstract]

Giorgi-Renault S (2005)
[4-Aza-2,3-didehydropodophyllotoxins: new lignan with antitumor activity obtained from one-step synthesis].
Annales pharmaceutiques francaises 63, 63-68 [PubMed:15803102]
[show Abstract]

Northover AM, Northover BJ (1993)
Possible involvement of microtubules in platelet-activating factor-induced increases in microvascular permeability in vitro.
Inflammation 17, 633-639 [PubMed:8112825]
[show Abstract]

Last Modified

22 February 2017

ChEBI

CHEBI:50305 - podophyllotoxin

Background

Objective

Materials and methods

Results

Conclusion

Unlabelled

Background

Result

Conclusions

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