sandwicensin (CHEBI:66165)

ChEBI > Main

Main

ChEBI Ontology

Automatic Xrefs

Reactions

Pathways

Models

ChEBI Name	sandwicensin

ChEBI ID	CHEBI:66165

Definition	A member of the class of pterocarpans that is (6aR,11aR)-pterocarpan substituted by a hydroxy group at position 3, a methoxy group at position 9 and a prenyl group at position 10. Isolated from Erythrina glauca and Erythrina stricta, it exhibits anti-HIV-1 activity.

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

Supplier Information

Download	Molfile XML SDF

Formula

C21H22O4

Net Charge

Average Mass

338.39700

Monoisotopic Mass

338.15181

InChI

InChI=1S/C21H22O4/c1-12(2)4-6-15-18(23-3)9-8-14-17-11-24-19-10-13(22)5-7-16(19)21(17)25-20(14)15/h4-5,7-10,17,21-22H,6,11H2,1-3H3/t17-,21-/m0/s1

InChIKey

ZFUZIYGRFSXEIQ-UWJYYQICSA-N

SMILES

[H][C@@]12COc3cc(O)ccc3[C@]1([H])Oc1c(CC=C(C)C)c(OC)ccc21

Metabolite of Species	Details
Erythrina × bidwillii (IPNI:494362-1)	See: DOI
Erythrina glauca (IPNI:494436-1)	Found in bark (BTO:0001301). See: PubMed
Erythrina mildbraedii (IPNI:494506-1)	See: DOI
Erythrina stricta (IPNI:494596-1)	Found in root (BTO:0001188). See: PubMed
Erythrina poeppigiana (IPNI:96637-2)	Found in root (BTO:0001188). See: PubMed
Erythrina lysistemon (NCBI:txid347910)	Found in flower (BTO:0000469). See: PROCEEDINGS OF THE 11TH NAPRECA SYMPOSIUM,AUGUST 9-12,ANTANANARIVO,MADAGASCAR,2005,97-109
Erythrina lysistemon (NCBI:txid347910)	Found in aerial part (BTO:0001658). See: PROCEEDINGS OF THE 11TH NAPRECA SYMPOSIUM,AUGUST 9-12,ANTANANARIVO,MADAGASCAR,2005,97-109

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. anti-HIV-1 agent An anti-HIV agent that destroys or inhibits the replication of HIV-1, the more infective and more virulent of the two types of HIV virus.

ChEBI Ontology
Outgoing	sandwicensin (CHEBI:66165) has role anti-HIV-1 agent (CHEBI:64947) sandwicensin (CHEBI:66165) has role metabolite (CHEBI:25212) sandwicensin (CHEBI:66165) is a aromatic ether (CHEBI:35618) sandwicensin (CHEBI:66165) is a phenols (CHEBI:33853) sandwicensin (CHEBI:66165) is a pterocarpans (CHEBI:26377)

IUPAC Name

(6aR,11aR)-9-methoxy-10-(3-methylbut-2-en-1-yl)-6a,11a-dihydro-6H-[1]benzofuro[3,2-c]chromen-3-ol

Synonym	Source
3-hydroxy-9-methoxy-10-prenylpterocarpan	ChEBI

Registry Number	Type	Source
9220627	Reaxys Registry Number	Reaxys

Last Modified

25 April 2013

General Comment
2012-07-27	PROCEEDINGS OF THE 11TH NAPRECA SYMPOSIUM,AUGUST 9-12,ANTANANARIVO,MADAGASCAR,2005,97-109