CHEBI:75251 - picropodophyllotoxin

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ChEBI Name picropodophyllotoxin
ChEBI ID CHEBI:75251
Definition An organic heterotetracyclic compound that has a furonaphthodioxole skeleton bearing 3,4,5-trimethoxyphenyl and hydroxy substituents.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:8204
Supplier Information
Download Molfile XML SDF
Formula C22H22O8
Net Charge 0
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-HAEOHBJNSA-N
SMILES [H][C@]12COC(=O)[C@@]1([H])[C@H](c1cc(OC)c(OC)c(OC)c1)c1cc3OCOc3cc1[C@@H]2O
Metabolite of Species Details
Podophyllum peltatum (NCBI:txid35933) Found in root (BTO:0001188). See: Book: American Medicinal Plants by Charles F. Millspaugh (Nov. 1974)
Roles Classification
Biological Role(s): tyrosine kinase inhibitor
Any protein kinase inhibitor that interferes with the action of tyrosine kinase.
insulin-like growth factor receptor 1 antagonist
An antagonist at the insulin-like growth factor receptor 1.
plant metabolite
Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
Application(s): antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing picropodophyllotoxin (CHEBI:75251) has role antineoplastic agent (CHEBI:35610)
picropodophyllotoxin (CHEBI:75251) has role insulin-like growth factor receptor 1 antagonist (CHEBI:75252)
picropodophyllotoxin (CHEBI:75251) has role plant metabolite (CHEBI:76924)
picropodophyllotoxin (CHEBI:75251) has role tyrosine kinase inhibitor (CHEBI:38637)
picropodophyllotoxin (CHEBI:75251) is a furonaphthodioxole (CHEBI:50307)
picropodophyllotoxin (CHEBI:75251) is a lignan (CHEBI:25036)
picropodophyllotoxin (CHEBI:75251) is a organic heterotetracyclic compound (CHEBI:38163)
IUPAC Name
(5R,5aS,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
Synonym Source
Picropodophyllin ChemIDplus
Manual Xrefs Databases
C00002619 KNApSAcK
C10871 KEGG COMPOUND
HMDB0031452 HMDB
WO2012047172 Patent
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Registry Numbers Types Sources
477-47-4 CAS Registry Number ChemIDplus
99161 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
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Last Modified
14 August 2016