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

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

ChEBI ID	CHEBI:69248
ChEBI Name	(2S,3S)-2,3-dihydro-3-hydroxymethyl-2-(4-hydroxyphenyl)-5-(E)-propenylbenzofuran
Stars
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.
Last Modified	13 April 2015
Downloads	Molfile

Formula	C18H18O3
Net Charge	0
Average Mass	282.339
Monoisotopic Mass	282.12559
SMILES	C/C=C/c1ccc2c(c1)[C@@H](CO)[C@@H](c1ccc(O)cc1)O2
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

Species of Metabolite	Component	Source	Comments
Krameria lappacea (ncbitaxon:228636)	root (BTO:0001188)	PubMed (21800856)	Methylene dichloride extract of dried and ground roots

Roles Classification

Biological Roles:

NF-kappaB inhibitor An inhibitor of NF-κB (nuclear factor κ-light-chain-enhancer of activated B cells), a protein complex involved in the transcription of DNA.

cyclooxygenase 2 inhibitor A cyclooxygenase inhibitor that interferes with the action of cyclooxygenase 2.

cyclooxygenase 1 inhibitor A cyclooxygenase inhibitor that interferes with the action of cyclooxygenase 1.

plant metabolite Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.

Application:

anti-inflammatory agent Any compound that has anti-inflammatory effects.

ChEBI Ontology

Outgoing Relation(s)
	(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 Numbers	Sources
Reaxys:6419322	Reaxys

Citations