silvestrol (CHEBI:66484)

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CHEBI:66484 - silvestrol

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ChEBI ID	CHEBI:66484
ChEBI Name	silvestrol
Stars
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.
Last Modified	9 March 2018
Downloads	Molfile

Formula	C34H38O13
Net Charge	0
Average Mass	654.665
Monoisotopic Mass	654.23124
SMILES	[H][C@]1([C@H](O)CO)CO[C@@H](OC)[C@H](Oc2cc(OC)c3c(c2)O[C@@]2(c4ccc(OC)cc4)[C@H](c4ccccc4)[C@@H](C(=O)OC)[C@@H](O)[C@@]32O)O1
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

Species of Metabolite	Component	Source	Comments
Aglaia foveolata (IPNI:968391-1)
	leaf (BTO:0000713)	PubMed (20939540)	Methanolic extract of dried stem bark
	twig (BTO:0001411)	PubMed (20939540)	Methanolic extract of dried stem bark
	fruit (BTO:0000486)	PubMed (20939540)	Methanolic extract of dried stem bark
	stem (BTO:0001300)	PubMed (20939540)	Previous component: stem bark; Methanolic extract of dried stem bark
Aglaia leptantha (IPNI:577166-1)	-	PubMed (20939540)
Aglaia silvestris (ncbitaxon:306516)
	fruit (BTO:0000486)	PubMed (15132542)
	twig (BTO:0001411)	PubMed (15132542)

Roles Classification

Biological Role:	metabolite Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
Application:	antineoplastic agent A substance that inhibits or prevents the proliferation of neoplasms.

ChEBI Ontology

Outgoing Relation(s)
	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

Registry Numbers	Sources
Reaxys:9977230	Reaxys

Citations