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CHEBI:65394 - alvaradoin I

ChEBI IDCHEBI:65394
ChEBI Namealvaradoin I
Stars
DefinitionA C-glycosyl compound that is 1,8,10-trihydroxy-3-methylanthracen-9-one substituted by a 1-O-acetyl-3-O-senecioyl-α-L-lyxopyranosyl moiety at position 10 via a C-glycosidic linkage (the 10R stereoisomer). It is isolated from the leaves of Alvaradoa haitiensis and exhibits cytotoxicity against human oral epidermoid carcinoma.
Last Modified26 November 2012
DownloadsMolfile
FormulaC27H28O11
Net Charge0
Average Mass528.510
Monoisotopic Mass528.16316
SMILES[H][C@@]1([C@@]2(O)c3cccc(O)c3C(=O)c3c(O)cc(C)cc32)O[C@@H](OC(C)=O)[C@H](O)[C@H](OC(=O)C=C(C)C)[C@H]1O
InChIInChI=1S/C27H28O11/c1-11(2)8-18(31)37-24-22(33)25(38-26(23(24)34)36-13(4)28)27(35)14-6-5-7-16(29)19(14)21(32)20-15(27)9-12(3)10-17(20)30/h5-10,22-26,29-30,33-35H,1-4H3/t22-,23-,24-,25-,26-,27-/m1/s1
InChIKeyCWTBVTWONZDFAF-ZRRJEQDASA-N
Species of MetaboliteComponentSourceComments
Alvaradoa haitiensis (IPNI:10503-2) leaf (BTO:0000713) PubMed (17552563)
Roles Classification
Biological Role:
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)
alvaradoin I (CHEBI:65394) has functional parent 3-methylbut-2-enoic acid (CHEBI:37127)
alvaradoin I (CHEBI:65394) has role antineoplastic agent (CHEBI:35610)
alvaradoin I (CHEBI:65394) has role metabolite (CHEBI:25212)
alvaradoin I (CHEBI:65394) is a C-glycosyl compound (CHEBI:20857)
alvaradoin I (CHEBI:65394) is a acetate ester (CHEBI:47622)
alvaradoin I (CHEBI:65394) is a anthracenes (CHEBI:46955)
alvaradoin I (CHEBI:65394) is a polyphenol (CHEBI:26195)
IUPAC Name 
(5R)-1-O-acetyl-3-O-(3-methylbut-2-enoyl)-5-[(9R)-4,5,9-trihydroxy-2-methyl-10-oxo-9,10-dihydroanthracen-9-yl]-α-L-lyxopyranose
Synonym  Source
(10R)-C-(1-O-acetyl-3-O-senecioyl)-β-L-lyxopyranosyl-1,8,10-trihydroxy-3-methylanthracen-9-oneChEBI
Registry NumbersSources
Reaxys:11184551Reaxys
Citations