breynceanothanolic acid (CHEBI:67583)

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CHEBI:67583 - breynceanothanolic acid

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ChEBI ID	CHEBI:67583
ChEBI Name	breynceanothanolic acid
Stars
Definition	A triterpenoid of the nor-ceanothane-type isolated from the roots of Breynia fruticosa and has been shown to exhibit cytotoxicity against human cancer cell lines.
Last Modified	9 January 2014
Downloads	Molfile

Formula	C29H40O5
Net Charge	0
Average Mass	468.634
Monoisotopic Mass	468.28757
SMILES	[H][C@]12CC[C@@]34OC(=O)[C@]1(CC[C@@]1(C(=O)O)CC[C@@H](C(=C)C)[C@@]12[H])[C@]3(C)CC[C@]12O[C@]41[C@@H](C)CC2(C)C
InChI	InChI=1S/C29H40O5/c1-16(2)18-7-9-25(21(30)31)12-13-26-19(20(18)25)8-10-28(33-22(26)32)24(26,6)11-14-27-23(4,5)15-17(3)29(27,28)34-27/h17-20H,1,7-15H2,2-6H3,(H,30,31)/t17-,18-,19+,20+,24-,25-,26+,27+,28+,29-/m0/s1
InChIKey	SNCMVKNGLNUISS-GCWSBASFSA-N

Species of Metabolite	Component	Source	Comments
Breynia fruticosa (ncbitaxon:296042)	root (BTO:0001188)	PubMed (21428418)	90% Methanolic extract of air-dried, crushed roots

Roles Classification

Chemical Role:	Bronsted acid A molecular entity capable of donating a hydron to an acceptor (Brønsted base).
Biological Role:	plant metabolite Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
Application:	antineoplastic agent A substance that inhibits or prevents the proliferation of neoplasms.

ChEBI Ontology

Outgoing Relation(s)
	breynceanothanolic acid (CHEBI:67583) has role antineoplastic agent (CHEBI:35610)
	breynceanothanolic acid (CHEBI:67583) has role plant metabolite (CHEBI:76924)
	breynceanothanolic acid (CHEBI:67583) is a epoxide (CHEBI:32955)
	breynceanothanolic acid (CHEBI:67583) is a monocarboxylic acid (CHEBI:25384)
	breynceanothanolic acid (CHEBI:67583) is a organic heteroheptacyclic compound (CHEBI:52157)
	breynceanothanolic acid (CHEBI:67583) is a terpene lactone (CHEBI:37668)
	breynceanothanolic acid (CHEBI:67583) is a triterpenoid (CHEBI:36615)

IUPAC Name
(1S,3aR,5aS,5bS,7aS,10R,10aR,10bR,12aR,12bS)-1,3,3,5a-tetramethyl-15-oxo-10-(prop-1-en-2-yl)dodecahydro-1H,4H-3a,12b-epoxy-12a,5b-(epoxymethano)dicyclopenta[a,i]phenanthrene-7a(8H)-carboxylic acid

Synonym	Source
5α,10α-epoxy-9α,27α-lactone-25(10→2α)abeo-A(1)-norlup-20(29)-en-28-oic acid	ChEBI

Registry Numbers	Sources
Reaxys:21553370	Reaxys

Citations