taiwanin C (CHEBI:191411)

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ChEBI Name	taiwanin C

ChEBI ID	CHEBI:191411

Definition	A furonaphthodioxole that is furo[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6(8H)-one substituted by a 1,3-benzodioxol-5-yl group at position 5. It is a naturally occurring lignan extracted from Taiwania cryptomerioides and found to be a potential inhibitor of COX2 expression.

Stars	This entity has been manually annotated by the ChEBI Team.

Submitter	Stan Laulederkind

Supplier Information

Download	Molfile XML SDF

Formula

C20H12O6

Net Charge

Average Mass

348.310

Monoisotopic Mass

348.06339

InChI

InChI=1S/C20H12O6/c21-20-19-12(7-22-20)3-11-5-16-17(26-9-25-16)6-13(11)18(19)10-1-2-14-15(4-10)24-8-23-14/h1-6H,7-9H2

InChIKey

YMGOOHXUOWZQOE-UHFFFAOYSA-N

SMILES

O=C1OCC2=CC3=C(C=C4OCOC4=C3)C(=C12)C1=CC2=C(OCO2)C=C1

Metabolite of Species	Details
Cleistanthus patulus (IPNI:341431-1)	See: PubMed
Acanthopanax henryi (IPNI:89458-1)	See: PubMed
Taiwania cryptomerioides (NCBI:txid50187)	See: PubMed
Justicia procumbens (NCBI:txid859317)	See: PubMed
Eleutherococcus divaricatus var. chiisanensis (NCBI:txid96666)	Found in Root (BTO:0001188). Species also known as Acanthopanax chiisanensis. 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.

Application(s):	antineoplastic agent A substance that inhibits or prevents the proliferation of neoplasms. platelet aggregation inhibitor A drug or agent which antagonizes or impairs any mechanism leading to blood platelet aggregation, whether during the phases of activation and shape change or following the dense-granule release reaction and stimulation of the prostaglandin-thromboxane system.

ChEBI Ontology
Outgoing	taiwanin C (CHEBI:191411) has role antineoplastic agent (CHEBI:35610) taiwanin C (CHEBI:191411) has role plant metabolite (CHEBI:76924) taiwanin C (CHEBI:191411) has role platelet aggregation inhibitor (CHEBI:50427) taiwanin C (CHEBI:191411) is a benzodioxoles (CHEBI:38298) taiwanin C (CHEBI:191411) is a furonaphthodioxole (CHEBI:50307) taiwanin C (CHEBI:191411) is a lignan (CHEBI:25036)

IUPAC Name

5-(1,3-benzodioxol-5-yl)furo[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6(8H)-one

Synonyms	Sources
5-(1,3-benzodioxol-5-yl)-8H-[2]benzofuro[5,6-f][1,3]benzodioxol-6-one	SUBMITTER
5-(2H-1,3-benzodioxol-5-yl)-2H-furo[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6(8H)-one	IUPAC
6,7-(epoxymethanoxy)-9-(1,3-benzodioxole-5-yl)-1,3-dihydronaphtho[2,3-c]furan-1-one	SUBMITTER

Registry Number	Type	Source
14944-34-4	CAS Registry Number	SUBMITTER

Last Modified

02 June 2023