(2S,3S)-2,3-dihydro-3-hydroxymethyl-2-(4-hydroxyphenyl)-5-(E)-propenylbenzofuran (CHEBI:69248)

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ChEBI Name	(2S,3S)-2,3-dihydro-3-hydroxymethyl-2-(4-hydroxyphenyl)-5-(E)-propenylbenzofuran

ChEBI ID	CHEBI:69248

ChEBI ASCII Name	(2S,3S)-2,3-dihydro-3-hydroxymethyl-2-(4-hydroxyphenyl)-5-(E)-propenylbenzofuran

Definition	A member of the class of benzofurans that is 2,3-dihydro-1-benzofuran substituted by a hydroxymethyl group at position 3, a prop-1-en-1-yl group at position 5 and a 4-hydroxyphenyl group at position 2. It is a lignan derivative isolated from the roots of Krameria lappacea.

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

Supplier Information

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Formula

C18H18O3

Net Charge

Average Mass

282.33370

Monoisotopic Mass

282.12559

InChI

InChI=1S/C18H18O3/c1-2-3-12-4-9-17-15(10-12)16(11-19)18(21-17)13-5-7-14(20)8-6-13/h2-10,16,18-20H,11H2,1H3/b3-2+/t16-,18-/m1/s1

InChIKey

OGRAMAAKQPETEE-OTUKTJHOSA-N

SMILES

C\C=C\c1ccc2O[C@@H]([C@H](CO)c2c1)c1ccc(O)cc1

Metabolite of Species	Details
Krameria lappacea (NCBI:txid228636)	Found in root (BTO:0001188). Methylene dichloride extract of dried and ground roots See: PubMed

Roles Classification
Biological Role(s):	cyclooxygenase 1 inhibitor A cyclooxygenase inhibitor that interferes with the action of cyclooxygenase 1. cyclooxygenase 2 inhibitor A cyclooxygenase inhibitor that interferes with the action of cyclooxygenase 2. NF-kappaB inhibitor An inhibitor of NF-kappaB (nuclear factor kappa-light-chain-enhancer of activated B cells), a protein complex involved in the transcription of DNA. plant metabolite Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.

Application(s):	anti-inflammatory agent Any compound that has anti-inflammatory effects.

ChEBI Ontology
Outgoing	(2S,3S)-2,3-dihydro-3-hydroxymethyl-2-(4-hydroxyphenyl)-5-(E)-propenylbenzofuran (CHEBI:69248) has role anti-inflammatory agent (CHEBI:67079) (2S,3S)-2,3-dihydro-3-hydroxymethyl-2-(4-hydroxyphenyl)-5-(E)-propenylbenzofuran (CHEBI:69248) has role cyclooxygenase 1 inhibitor (CHEBI:50630) (2S,3S)-2,3-dihydro-3-hydroxymethyl-2-(4-hydroxyphenyl)-5-(E)-propenylbenzofuran (CHEBI:69248) has role cyclooxygenase 2 inhibitor (CHEBI:50629) (2S,3S)-2,3-dihydro-3-hydroxymethyl-2-(4-hydroxyphenyl)-5-(E)-propenylbenzofuran (CHEBI:69248) has role NF-κB inhibitor (CHEBI:73240) (2S,3S)-2,3-dihydro-3-hydroxymethyl-2-(4-hydroxyphenyl)-5-(E)-propenylbenzofuran (CHEBI:69248) has role plant metabolite (CHEBI:76924) (2S,3S)-2,3-dihydro-3-hydroxymethyl-2-(4-hydroxyphenyl)-5-(E)-propenylbenzofuran (CHEBI:69248) is a benzofurans (CHEBI:35259) (2S,3S)-2,3-dihydro-3-hydroxymethyl-2-(4-hydroxyphenyl)-5-(E)-propenylbenzofuran (CHEBI:69248) is a phenols (CHEBI:33853) (2S,3S)-2,3-dihydro-3-hydroxymethyl-2-(4-hydroxyphenyl)-5-(E)-propenylbenzofuran (CHEBI:69248) is a primary alcohol (CHEBI:15734)

IUPAC Name

4-{(2S,3S)-3-(hydroxymethyl)-5-[(1E)-prop-1-en-1-yl]-2,3-dihydro-1-benzofuran-2-yl}phenol

Registry Number	Type	Source
6419322	Reaxys Registry Number	Reaxys

Citation	Type	Source
21800856	PubMed citation	Europe PMC

Last Modified

13 April 2015