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CHEBI:1729 - 4'-demethyldeoxypodophyllotoxin

Default Structure
ChEBI IDCHEBI:1729
ChEBI Name4'-demethyldeoxypodophyllotoxin
Stars
DefinitionA 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.
Last Modified14 July 2016
DownloadsMolfile
FormulaC21H20O7
Net Charge0
Average Mass384.384
Monoisotopic Mass384.12090
SMILES[H][C@]12COC(=O)[C@]1([H])[C@H](c1cc(OC)c(O)c(OC)c1)c1cc3c(cc1C2)OCO3
InChIInChI=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
InChIKeyRFDMNXDDRXVJTM-RQUSPXKASA-N
Species of MetaboliteComponentSourceComments
Dysosma versipellis (ncbitaxon:93611) root (BTO:0001188) PubMed (17256902)
Polygala macradenia (ncbitaxon:174543) - PubMed (853371)
Roles Classification
Chemical Role:
antioxidant  A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides.
Biological Roles:
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.
plant metabolite  Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
Applications:
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.
ChEBI Ontology
Outgoing Relation(s)
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 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)
4'-demethyldeoxypodophyllotoxin (CHEBI:1729) is a γ-lactone (CHEBI:37581)
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  Source
(−)-4'-demethyldeoxypodophyllotoxinChEBI
4'-desmethyldesoxypodophyllotoxinChEBI
A 80198ChemIDplus
UniProt Name  Source
(−)-4'-desmethyl-deoxypodophyllotoxinUniProt
Manual XrefsDatabases
C00002594KNApSAcK
C10552KEGG COMPOUND
CN101647842Patent
CPD-18756MetaCyc
Registry NumbersSources
Reaxys:1356937Reaxys
CAS:3590-93-0KEGG COMPOUND
CAS:3590-93-0ChemIDplus
Citations