CHEBI:4429 - deoxypodophyllotoxin

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ChEBI Name deoxypodophyllotoxin
ChEBI ID CHEBI:4429
Definition 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.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C22H22O7
Net Charge 0
Average Mass 398.407
Monoisotopic Mass 398.13655
InChI InChI=1S/C22H22O7/c1-24-17-6-12(7-18(25-2)21(17)26-3)19-14-8-16-15(28-10-29-16)5-11(14)4-13-9-27-22(23)20(13)19/h5-8,13,19-20H,4,9-10H2,1-3H3/t13-,19+,20-/m0/s1
InChIKey ZGLXUQQMLLIKAN-SVIJTADQSA-N
SMILES [C@H]1(C2=C(C[C@@]3([C@@]1(C(OC3)=O)[H])[H])C=C4OCOC4=C2)C5=CC(=C(OC)C(=C5)OC)OC
Metabolite of Species Details
Anthriscus sylvestris (NCBI:txid48027) See: PubMed
Juniperus communis (NCBI:txid58039) See: PubMed
Dysosma versipellis (NCBI:txid93611) See: PubMed
Roles Classification
Biological Role(s): plant metabolite
Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
apoptosis inducer
Any substance that induces the process of apoptosis (programmed cell death) in multi-celled organisms.
Application(s): antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing deoxypodophyllotoxin (CHEBI:4429) has role antineoplastic agent (CHEBI:35610)
deoxypodophyllotoxin (CHEBI:4429) has role apoptosis inducer (CHEBI:68495)
deoxypodophyllotoxin (CHEBI:4429) has role plant metabolite (CHEBI:76924)
deoxypodophyllotoxin (CHEBI:4429) is a γ-lactone (CHEBI:37581)
deoxypodophyllotoxin (CHEBI:4429) is a furonaphthodioxole (CHEBI:50307)
deoxypodophyllotoxin (CHEBI:4429) is a lignan (CHEBI:25036)
deoxypodophyllotoxin (CHEBI:4429) is a methoxybenzenes (CHEBI:51683)
IUPAC Name
(5R,5aR,8aR)-5-(3,4,5-trimethoxyphenyl)-5,8,8a,9-tetrahydro-2H-furo[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6(5aH)-one
Synonyms Sources
(−)-deoxypodophyllotoxin UniProt
(-)-Anthricin ChemIDplus
(-)-Desoxypodophyllotoxin ChemIDplus
4-Deoxypodophyllotoxin ChemIDplus
Anthricin KNApSAcK
Desoxypodophyllotoxin ChemIDplus
Hernandin ChemIDplus
Hernandion ChemIDplus
Silicicolin KNApSAcK
Manual Xrefs Databases
C00002597 KNApSAcK
C10556 KEGG COMPOUND
CPD-8958 MetaCyc
View more database links
Registry Numbers Types Sources
19186-35-7 CAS Registry Number NIST Chemistry WebBook
19186-35-7 CAS Registry Number ChemIDplus
98060 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
24176745 PubMed citation Europe PMC
24913660 PubMed citation Europe PMC
25608854 PubMed citation Europe PMC
25712646 PubMed citation Europe PMC
25720974 PubMed citation Europe PMC
26470595 PubMed citation Europe PMC
26573436 PubMed citation Europe PMC
26683770 PubMed citation Europe PMC
Last Modified
14 July 2016