EMBL-EBI | Chemical Biology | ChEBI

Example searches: iron*, InChI=1S/CH4O/c1-2/h2H,1H3, caffeine | Advanced Search

CHEBI:50305 - podophyllotoxin

ChEBI IDCHEBI:50305
ChEBI Namepodophyllotoxin
Stars
DefinitionAn 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.
Secondary ChEBI IDsCHEBI:8280, CHEBI:45070
Last Modified22 February 2017
SubmitterMarcus Ennis
DownloadsMolfile
FormulaC22H22O8
Net Charge0
Average Mass414.410
Monoisotopic Mass414.13147
SMILES[H][C@]12COC(=O)[C@]1([H])[C@H](c1cc(OC)c(OC)c(OC)c1)c1cc3c(cc1[C@@H]2O)OCO3
InChIInChI=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
InChIKeyYJGVMLPVUAXIQN-XVVDYKMHSA-N
Wikipedia
Roles Classification
Biological Roles:
plant metabolite  Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
tubulin modulator  Any substance that interacts with tubulin to inhibit or promote polymerisation of microtubules.
antimitotic  Any compound that inhibits cell division (mitosis).
microtubule-destabilising agent  Any substance that interacts with tubulin to inhibit polymerisation of microtubules.
Applications:
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.
ChEBI Ontology
Outgoing Relation(s)
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 Relation(s)
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  Source
PodophyllotoxinKEGG COMPOUND
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)-ONEPDBeChem
PodofiloxChemIDplus
Podophyllinic acid lactoneChemIDplus
PPTChEBI
(−)-podophyllotoxinChEBI
Brand Names  Source
CondyloxKEGG DRUG
Podophyllotoxin 7DrugBank
Manual XrefsDatabases
C10874KEGG COMPOUND
PODPDBeChem
D05529KEGG DRUG
DB01179DrugBank
PodophyllotoxinWikipedia
HMDB0031452HMDB
C00000610KNApSAcK
LSM-3055LINCS
3481DrugCentral
Registry NumbersSources
Reaxys:99163Reaxys
CAS:518-28-5KEGG COMPOUND
CAS:518-28-5ChemIDplus
Citations