CHEBI:65399 - alvaradoin N

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ChEBI Name alvaradoin N
ChEBI ID CHEBI:65399
Definition A C-glycosyl compound that is 1,8,10-trihydroxy-3-methylanthracen-9(10H)-one substituted by a 1-O-acetyl-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 C22H24O10
Net Charge 0
Average Mass 448.42000
Monoisotopic Mass 448.13695
InChI InChI=1S/C22H24O10/c1-8-6-11-15(13(25)7-8)16(26)14-10(4-3-5-12(14)24)22(11,30)20-18(28)17(27)19(29)21(32-20)31-9(2)23/h4,6-7,17-21,24-25,27-30H,3,5H2,1-2H3/t17-,18-,19-,20-,21-,22+/m1/s1
InChIKey SORBFYNXEINFLY-ILHTXMRTSA-N
SMILES [H][C@]1(O[C@@H](OC(C)=O)[C@H](O)[C@H](O)[C@H]1O)[C@]1(O)C2=CCCC(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 N (CHEBI:65399) has role antineoplastic agent (CHEBI:35610)
alvaradoin N (CHEBI:65399) has role metabolite (CHEBI:25212)
alvaradoin N (CHEBI:65399) is a C-glycosyl compound (CHEBI:20857)
alvaradoin N (CHEBI:65399) is a acetate ester (CHEBI:47622)
alvaradoin N (CHEBI:65399) is a anthracenes (CHEBI:46955)
alvaradoin N (CHEBI:65399) is a polyphenol (CHEBI:26195)
IUPAC Name
(5R)-1-O-acetyl-5-[(9S)-4,5,9-trihydroxy-2-methyl-10-oxo-9,10-dihydroanthracen-9-yl]-α-L-lyxopyranose
Synonym Source
(10S)-C-(1-O-acetyl)-β-L-lyxopyranosyl-1,8,10-trihydroxy-3-methylanthracen-9(10H)-one
Note: (2012-11-26) Note that this synonym is a misnomer; alvaradoin N is an α-L-lyxopyranose derivative.
 ChEBI
Registry Number Type Source
11184546 Reaxys Registry Number Reaxys
Citation Waiting for Citations Type Source
17552563 PubMed citation Europe PMC
Last Modified
26 November 2012