CHEBI:65398 - alvaradoin M

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ChEBI Name alvaradoin M
ChEBI ID CHEBI:65398
Definition A C-glycosyl compound that is 1,8-dihydroxy-3-methylanthracen-9(10H)-one substituted by a 3-O-senecioyl-α-L-lyxopyranosyl moiety at position 10 via a C-glycosidic linkage (the 10S stereoisomer). It is isolated from the leaves of Alvaradoa haitiensis and exhibits cytotoxicity against human oral epidermoid carcinoma.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C25H26O9
Net Charge 0
Average Mass 470.46850
Monoisotopic Mass 470.15768
InChI InChI=1S/C25H26O9/c1-10(2)7-16(28)33-24-21(30)23(34-25(32)22(24)31)17-12-5-4-6-14(26)18(12)20(29)19-13(17)8-11(3)9-15(19)27/h4-9,17,21-27,30-32H,1-3H3/t17-,21-,22+,23-,24+,25+/m0/s1
InChIKey XVEVCPOACUOIOH-AEPXPHGDSA-N
SMILES [H][C@]1(O[C@@H](O)[C@H](O)[C@H](OC(=O)C=C(C)C)[C@H]1O)[C@@]1([H])c2cccc(O)c2C(=O)c2c(O)cc(C)cc12
Metabolite of Species Details
Alvaradoa haitiensis (IPNI:10503-2) Found in leaf (BTO:0000713). See: PubMed
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.
Application(s): antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing alvaradoin M (CHEBI:65398) has functional parent 3-methylbut-2-enoic acid (CHEBI:37127)
alvaradoin M (CHEBI:65398) has role antineoplastic agent (CHEBI:35610)
alvaradoin M (CHEBI:65398) has role metabolite (CHEBI:25212)
alvaradoin M (CHEBI:65398) is a C-glycosyl compound (CHEBI:20857)
alvaradoin M (CHEBI:65398) is a anthracenes (CHEBI:46955)
alvaradoin M (CHEBI:65398) is a polyphenol (CHEBI:26195)
IUPAC Name
(5R)-5-[(9S)-4,5-dihydroxy-2-methyl-10-oxo-9,10-dihydroanthracen-9-yl]-3-O-(3-methylbut-2-enoyl)-α-L-lyxopyranose
Synonym Source
(10S)-C-(3-O-senecioyl)-β-L-lyxopyranosyl-1,8-dihydroxy-3-methylanthracen-9(10H)-one
Note: (2012-11-26) Note that this synonym is a misnomer; alvaradoin M is an α-L-lyxopyranose derivative.
 ChEBI
Registry Number Type Source
11184545 Reaxys Registry Number Reaxys
Citation Waiting for Citations Type Source
17552563 PubMed citation Europe PMC
Last Modified
26 November 2012