25-O-methoxycimigenol 3-O-alpha-L-arabinopyranoside (CHEBI:66702)

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CHEBI:66702 - 25-O-methoxycimigenol 3-O-α-L-arabinopyranoside

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ChEBI ID	CHEBI:66702
ChEBI Name	25-O-methoxycimigenol 3-O-α-L-arabinopyranoside
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ASCII Name	25-O-methoxycimigenol 3-O-alpha-L-arabinopyranoside
Definition	A triterpene glycoside that consists of 25-O-methoxycimigenol attached to a α-L-arabinopyranosyl residue at position 3 via a glycosidic linkage. Isolated from the rhizomes of Cimicifuga racemosa, it exhibits cytotoxic activities.
Last Modified	20 January 2014
Downloads	Molfile

Formula	C36H58O9
Net Charge	0
Average Mass	634.851
Monoisotopic Mass	634.40808
SMILES	[H][C@@]1(O[C@H]2CC[C@]34C[C@]35CC[C@]3(C)[C@@]6([H])[C@H](C)C[C@@]7([H])O[C@@]6(O[C@@H]7C(C)(C)OC)[C@H](O)[C@@]3(C)[C@]5([H])CC[C@@]4([H])C2(C)C)OC[C@H](O)[C@H](O)[C@H]1O
InChI	InChI=1S/C36H58O9/c1-18-15-20-27(31(4,5)41-8)45-36(44-20)26(18)32(6)13-14-35-17-34(35)12-11-23(43-28-25(39)24(38)19(37)16-42-28)30(2,3)21(34)9-10-22(35)33(32,7)29(36)40/h18-29,37-40H,9-17H2,1-8H3/t18-,19+,20-,21+,22+,23+,24+,25-,26-,27+,28+,29-,32-,33-,34-,35+,36+/m1/s1
InChIKey	LAOCOVISLMUJNC-NORDHZMASA-N

Species of Metabolite	Component	Source	Comments
Actaea racemosa (ncbitaxon:64040)	rhizome (BTO:0001181)	PubMed (11824572)

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. metabolite Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
Application:	antineoplastic agent A substance that inhibits or prevents the proliferation of neoplasms.

ChEBI Ontology

Outgoing Relation(s)
	25-O-methoxycimigenol 3-O-α-L-arabinopyranoside (CHEBI:66702) has functional parent cimigenol (CHEBI:37777)
	25-O-methoxycimigenol 3-O-α-L-arabinopyranoside (CHEBI:66702) has parent hydride cycloartane (CHEBI:37778)
	25-O-methoxycimigenol 3-O-α-L-arabinopyranoside (CHEBI:66702) has role antineoplastic agent (CHEBI:35610)
	25-O-methoxycimigenol 3-O-α-L-arabinopyranoside (CHEBI:66702) has role plant metabolite (CHEBI:76924)
	25-O-methoxycimigenol 3-O-α-L-arabinopyranoside (CHEBI:66702) is a bridged compound (CHEBI:35990)
	25-O-methoxycimigenol 3-O-α-L-arabinopyranoside (CHEBI:66702) is a cyclic ether (CHEBI:37407)
	25-O-methoxycimigenol 3-O-α-L-arabinopyranoside (CHEBI:66702) is a monosaccharide derivative (CHEBI:63367)
	25-O-methoxycimigenol 3-O-α-L-arabinopyranoside (CHEBI:66702) is a secondary alcohol (CHEBI:35681)
	25-O-methoxycimigenol 3-O-α-L-arabinopyranoside (CHEBI:66702) is a triterpenoid saponin (CHEBI:61778)
	25-O-methoxycimigenol 3-O-α-L-arabinopyranoside (CHEBI:66702) is a α-L-arabinopyranoside (CHEBI:37782)

IUPAC Name
(2S,4aR,5aS,7aR,7bR,8R,10R,11S,12aS,13R,13aS,13bR,15aR)-13-hydroxy-11-(2-methoxypropan-2-yl)-1,1,7a,8,13a-pentamethyloctadecahydro-10,12a-epoxycyclopropa[1',8a']naphtho[2',1':4,5]indeno[2,1-b]oxepin-2-yl α-L-arabinopyranoside

Registry Numbers	Sources
Reaxys:8890135	Reaxys

Citations