CHEBI:1729 - 4'-demethyldeoxypodophyllotoxin

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ChEBI Name 4'-demethyldeoxypodophyllotoxin
ChEBI ID CHEBI:1729
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 4-hydroxy-3,5-dimethoxyphenyl group.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
Download Molfile XML SDF
Formula C21H20O7
Net Charge 0
Average Mass 384.380
Monoisotopic Mass 384.12090
InChI InChI=1S/C21H20O7/c1-24-16-5-11(6-17(25-2)20(16)22)18-13-7-15-14(27-9-28-15)4-10(13)3-12-8-26-21(23)19(12)18/h4-7,12,18-19,22H,3,8-9H2,1-2H3/t12-,18+,19-/m0/s1
InChIKey RFDMNXDDRXVJTM-RQUSPXKASA-N
SMILES [C@H]1(C2=C(C[C@@]3([C@@]1(C(OC3)=O)[H])[H])C=C4OCOC4=C2)C5=CC(=C(C(=C5)OC)O)OC
Metabolite of Species Details
Polygala macradenia (NCBI:txid174543) See: PubMed
Dysosma versipellis (NCBI:txid93611) Found in root (BTO:0001188). See: PubMed
Roles Classification
Chemical Role(s): antioxidant
A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides.
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.
immunosuppressive agent
An agent that suppresses immune function by one of several mechanisms of action. Classical cytotoxic immunosuppressants act by inhibiting DNA synthesis. Others may act through activation of T-cells or by inhibiting the activation of helper cells. In addition, an immunosuppressive agent is a role played by a compound which is exhibited by a capability to diminish the extent and/or voracity of an immune response.
Application(s): immunosuppressive agent
An agent that suppresses immune function by one of several mechanisms of action. Classical cytotoxic immunosuppressants act by inhibiting DNA synthesis. Others may act through activation of T-cells or by inhibiting the activation of helper cells. In addition, an immunosuppressive agent is a role played by a compound which is exhibited by a capability to diminish the extent and/or voracity of an immune response.
antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 4'-demethyldeoxypodophyllotoxin (CHEBI:1729) has role antineoplastic agent (CHEBI:35610)
4'-demethyldeoxypodophyllotoxin (CHEBI:1729) has role antioxidant (CHEBI:22586)
4'-demethyldeoxypodophyllotoxin (CHEBI:1729) has role immunosuppressive agent (CHEBI:35705)
4'-demethyldeoxypodophyllotoxin (CHEBI:1729) has role plant metabolite (CHEBI:76924)
4'-demethyldeoxypodophyllotoxin (CHEBI:1729) is a γ-lactone (CHEBI:37581)
4'-demethyldeoxypodophyllotoxin (CHEBI:1729) is a furonaphthodioxole (CHEBI:50307)
4'-demethyldeoxypodophyllotoxin (CHEBI:1729) is a lignan (CHEBI:25036)
4'-demethyldeoxypodophyllotoxin (CHEBI:1729) is a methoxybenzenes (CHEBI:51683)
4'-demethyldeoxypodophyllotoxin (CHEBI:1729) is a phenols (CHEBI:33853)
IUPAC Name
(5R,5aR,8aR)-5-(4-hydroxy-3,5-dimethoxyphenyl)-5,8,8a,9-tetrahydro-2H-furo[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6(5aH)-one
Synonyms Sources
(−)-4'-demethyldeoxypodophyllotoxin ChEBI
(−)-4'-desmethyl-deoxypodophyllotoxin UniProt
4'-desmethyldesoxypodophyllotoxin ChEBI
A 80198 ChemIDplus
Manual Xrefs Databases
C00002594 KNApSAcK
C10552 KEGG COMPOUND
CN101647842 Patent
CPD-18756 MetaCyc
View more database links
Registry Numbers Types Sources
1356937 Reaxys Registry Number Reaxys
3590-93-0 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
10680579 PubMed citation Europe PMC
11800394 PubMed citation Europe PMC
12873481 PubMed citation Europe PMC
17256902 PubMed citation Europe PMC
17340533 PubMed citation Europe PMC
21676247 PubMed citation Europe PMC
296709 Chinese Abstracts citation Europe PMC
344537 Chinese Abstracts citation Europe PMC
853371 PubMed citation Europe PMC
8709118 PubMed citation Europe PMC
Last Modified
14 July 2016