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
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Formula C22H22O8
Net Charge 0
Average Mass 414.40530
Monoisotopic Mass 414.131
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.
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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 Waiting for Citations Types Sources
15803102 PubMed citation Europe PMC
22621772 PubMed citation Europe PMC
23161544 PubMed citation Europe PMC
23798883 PubMed citation Europe PMC
8112825 PubMed citation Europe PMC
Last Modified
22 February 2017