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CHEBI:66560 - lespeflorin A3

ChEBI IDCHEBI:66560
ChEBI Namelespeflorin A3
Stars
ASCII Namelespeflorin A3
DefinitionA monohydroxyflavanone that is flavanone substituted with a hydroxy group at position 7, prenyl groups at positions 6 and 8 and a 6,6-dimethyl-3,6-dihydro-2H-pyran ring fused across positions 3' and 4'. Isolated from the roots of Lespedeza floribunda, it acts as a melanin synthesis inhibitor.
Last Modified20 March 2013
DownloadsMolfile
FormulaC30H34O4
Net Charge0
Average Mass458.598
Monoisotopic Mass458.24571
SMILESCC(C)=CCc1cc2c(c(CC=C(C)C)c1O)O[C@H](c1ccc3c(c1)C=CC(C)(C)O3)CC2=O
InChIInChI=1S/C30H34O4/c1-18(2)7-9-22-16-24-25(31)17-27(33-29(24)23(28(22)32)11-8-19(3)4)20-10-12-26-21(15-20)13-14-30(5,6)34-26/h7-8,10,12-16,27,32H,9,11,17H2,1-6H3/t27-/m0/s1
InChIKeySAZBMMMZQLNWMN-MHZLTWQESA-N
Species of MetaboliteComponentSourceComments
Lespedeza floribunda (ncbitaxon:587870) root (BTO:0001188) PubMed (19132934)
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:
melanin synthesis inhibitor  A depigmentation agent which inhibits the synthesis of melanin.
ChEBI Ontology
Outgoing Relation(s)
lespeflorin A3 (CHEBI:66560) has role melanin synthesis inhibitor (CHEBI:64933)
lespeflorin A3 (CHEBI:66560) has role metabolite (CHEBI:25212)
lespeflorin A3 (CHEBI:66560) is a monohydroxyflavanone (CHEBI:38748)
IUPAC Name 
(2S)-7-hydroxy-2',2'-dimethyl-6,8-bis(3-methylbut-2-en-1-yl)-2,3-dihydro-2'H,4H-2,6'-bichromen-4-one
Registry NumbersSources
Reaxys:19089533Reaxys
Citations