CHEBI:66484 - silvestrol

Main ChEBI Ontology Automatic Xrefs Reactions Pathways Models
ChEBI Name silvestrol
ChEBI ID CHEBI:66484
Definition An organic heterotricyclic compound that consists of a 2,3,3a,8b-tetrahydro-H-benzo[b]cyclopenta[d]furan framework substituted by hydroxy groups at positions C-1 and C-8b, a methoxycarbonyl group at C-2, a phenyl group at C-3, a 4-methoxyphenyl group at C-3a, a methoxy group at C-8 and a 1,4-dioxan-2-yloxy group at position C-6 which in turn is substituted by a methoxy group at position 3 and a 1,2-dihydroxyethyl group at position 6. Isolated from Aglaia silvestris, it exhibits antineoplastic activity.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
Download Molfile XML SDF
Formula C34H38O13
Net Charge 0
Average Mass 654.65770
Monoisotopic Mass 654.23124
InChI InChI=1S/C34H38O13/c1-40-20-12-10-19(11-13-20)34-27(18-8-6-5-7-9-18)26(30(38)42-3)29(37)33(34,39)28-23(41-2)14-21(15-24(28)47-34)45-32-31(43-4)44-17-25(46-32)22(36)16-35/h5-15,22,25-27,29,31-32,35-37,39H,16-17H2,1-4H3/t22-,25-,26-,27-,29-,31-,32-,33+,34+/m1/s1
InChIKey GVKXFVCXBFGBCD-QKDMMWSPSA-N
SMILES [H][C@@]1(CO[C@@H](OC)[C@H](Oc2cc(OC)c3c(O[C@]4([C@@H]([C@H]([C@@H](O)[C@@]34O)C(=O)OC)c3ccccc3)c3ccc(OC)cc3)c2)O1)[C@H](O)CO
Metabolite of Species Details
Aglaia leptantha (IPNI:577166-1) See: PubMed
Aglaia foveolata (IPNI:968391-1) Found in twig (BTO:0001411). Methanolic extract of dried stem bark See: PubMed
Aglaia foveolata (IPNI:968391-1) Found in leaf (BTO:0000713). Methanolic extract of dried stem bark See: PubMed
Aglaia foveolata (IPNI:968391-1) Found in fruit (BTO:0000486). Methanolic extract of dried stem bark See: PubMed
Aglaia foveolata (IPNI:968391-1) Found in stem (BTO:0001300). Previous component: stem bark; Methanolic extract of dried stem bark See: PubMed
Aglaia silvestris (NCBI:txid306516) Found in twig (BTO:0001411). See: PubMed
Aglaia silvestris (NCBI:txid306516) Found in fruit (BTO:0000486). See: PubMed
Roles Classification
Biological Role(s): metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
Application(s): antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing silvestrol (CHEBI:66484) has role antineoplastic agent (CHEBI:35610)
silvestrol (CHEBI:66484) has role metabolite (CHEBI:25212)
silvestrol (CHEBI:66484) is a dioxanes (CHEBI:46926)
silvestrol (CHEBI:66484) is a ether (CHEBI:25698)
silvestrol (CHEBI:66484) is a methyl ester (CHEBI:25248)
silvestrol (CHEBI:66484) is a organic heterotricyclic compound (CHEBI:26979)
IUPAC Name
methyl (1R,2R,3S,3aR,8bS)-6-({(2S,3R,6R)-6-[(1R)-1,2-dihydroxyethyl]-3-methoxy-1,4-dioxan-2-yl}oxy)-1,8b-dihydroxy-8-methoxy-3a-(4-methoxyphenyl)-3-phenyl-2,3,3a,8b-tetrahydro-1H-benzo[b]cyclopenta[d]furan-2-carboxylate
Synonym Source
(−)-silvestrol ChEBI
Manual Xrefs Databases
US2009186839 Patent
WO2013016658 Patent
View more database links
Registry Number Type Source
9977230 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
15132542 PubMed citation Europe PMC
17695501 PubMed citation Europe PMC
19401772 PubMed citation Europe PMC
19412536 PubMed citation Europe PMC
20939540 PubMed citation Europe PMC
23025805 PubMed citation Europe PMC
23497456 PubMed citation Europe PMC
Last Modified
09 March 2018