erybraedin A (CHEBI:65862)

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CHEBI:65862 - erybraedin A

ChEBI ID	CHEBI:65862
ChEBI Name	erybraedin A
Stars
Definition	A member of the class of pterocarpans that is 3,9-dihydroxypterocarpan substituted with prenyl groups at positions 4 and 10 (the 6aR,11aR stereoisomer). Isolated from Erythrina stricta and Erythrina zeyheri, it exhibits antibacterial, antimycobacterial, antiplasmodial and cytotoxic activities.
Last Modified	16 January 2014
Downloads	Molfile

Formula	C25H28O4
Net Charge	0
Average Mass	392.495
Monoisotopic Mass	392.19876
SMILES	[H][C@@]12COc3c(ccc(O)c3CC=C(C)C)[C@]1([H])Oc1c2ccc(O)c1CC=C(C)C
InChI	InChI=1S/C25H28O4/c1-14(2)5-7-17-21(26)12-10-19-23(17)28-13-20-16-9-11-22(27)18(8-6-15(3)4)24(16)29-25(19)20/h5-6,9-12,20,25-27H,7-8,13H2,1-4H3/t20-,25-/m0/s1
InChIKey	HOGHBEDTLGAJAS-CPJSRVTESA-N

Species of Metabolite	Component	Source	Comments
Erythrina mildbraedii (IPNI:494506-1)	-	DOI (10.1016/0031-9422(88)80746-5)
Erythrina stricta (IPNI:494596-1)	root (BTO:0001188)	PubMed (18087807)
Erythrina subumbrans (IPNI:494601-1)
	bark (BTO:0001301)	PubMed (17055201)
	stem (BTO:0001300)	PubMed (17055201)
Erythrina zeyheri (ncbitaxon:347911)	root (BTO:0001188)	PubMed (15597305)
Erythrina burttii (IPNI:494372-1)	root (BTO:0001188)	DOI (10.1016/S0031-9422(01)00459-9)	Previous component: root bark;
Erythrina eriotricha (IPNI:494416-1)	root (BTO:0001188)	PubMed (8590641)	Previous component: root bark;

Roles Classification

Biological Roles:

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

antibacterial agent A substance (or active part thereof) that kills or slows the growth of bacteria.

antiplasmodial drug An antiparasitic drug which is effective against Apicomplexan parasites in the genus Plasmodium. The genus contains over 200 species and includes those responsible for malaria.

Applications:

antineoplastic agent A substance that inhibits or prevents the proliferation of neoplasms.

antiplasmodial drug An antiparasitic drug which is effective against Apicomplexan parasites in the genus Plasmodium. The genus contains over 200 species and includes those responsible for malaria.

ChEBI Ontology

Outgoing Relation(s)
	erybraedin A (CHEBI:65862) has functional parent (6aR,11aR)-3,9-dihydroxypterocarpan (CHEBI:15648)
	erybraedin A (CHEBI:65862) has role antibacterial agent (CHEBI:33282)
	erybraedin A (CHEBI:65862) has role antineoplastic agent (CHEBI:35610)
	erybraedin A (CHEBI:65862) has role antiplasmodial drug (CHEBI:64915)
	erybraedin A (CHEBI:65862) has role plant metabolite (CHEBI:76924)
	erybraedin A (CHEBI:65862) is a phenols (CHEBI:33853)
	erybraedin A (CHEBI:65862) is a pterocarpans (CHEBI:26377)

IUPAC Name
(6aR,11aR)-4,10-bis(3-methylbut-2-en-1-yl)-6a,11a-dihydro-6H-[1]benzofuro[3,2-c]chromene-3,9-diol

Synonyms	Source
(6aR,11aR-cis)-6a,11a-dihydro-4,10-bis(3-methyl-2-butenyl)-6H-benzofuro(3,2-c)(1)benzopyran-3,9-diol	ChemIDplus
4-prenylphaseollidin	ChEBI

Manual Xrefs	Databases
LMPK12070044	LIPID MAPS

Registry Numbers	Sources
Reaxys:9090260	Reaxys
CAS:119269-76-0	ChemIDplus

Citations