EMBL-EBI | Chemical Biology | ChEBI

Example searches: iron*, InChI=1S/CH4O/c1-2/h2H,1H3, caffeine | Advanced Search

CHEBI:66563 - lespeflorin B4

ChEBI IDCHEBI:66563
ChEBI Namelespeflorin B4
Stars
ASCII Namelespeflorin B4
DefinitionA trihydroxyflavanone that is (2S)-flavanone substituted by hydroxy groups at positions 3, 5, 7 and 4' and prenyl groups at positions 6, 8 and 3'. Isolated from the roots of Lespedeza floribunda, it acts as a melanin synthesis inhibitor.
Last Modified6 April 2018
DownloadsMolfile
FormulaC30H36O6
Net Charge0
Average Mass492.612
Monoisotopic Mass492.25119
SMILESCC(C)=CCc1cc([C@H]2Oc3c(CC=C(C)C)c(O)c(CC=C(C)C)c(O)c3C(=O)[C@@H]2O)ccc1O
InChIInChI=1S/C30H36O6/c1-16(2)7-10-19-15-20(11-14-23(19)31)29-28(35)27(34)24-26(33)21(12-8-17(3)4)25(32)22(30(24)36-29)13-9-18(5)6/h7-9,11,14-15,28-29,31-33,35H,10,12-13H2,1-6H3/t28-,29+/m0/s1
InChIKeyHPUMCKZHBQPWBN-URLMMPGGSA-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 B4 (CHEBI:66563) has functional parent (2S)-flavanone (CHEBI:15606)
lespeflorin B4 (CHEBI:66563) has role melanin synthesis inhibitor (CHEBI:64933)
lespeflorin B4 (CHEBI:66563) has role metabolite (CHEBI:25212)
lespeflorin B4 (CHEBI:66563) is a 4'-hydroxyflavanones (CHEBI:140331)
lespeflorin B4 (CHEBI:66563) is a dihydroflavonols (CHEBI:48039)
lespeflorin B4 (CHEBI:66563) is a secondary α-hydroxy ketone (CHEBI:2468)
lespeflorin B4 (CHEBI:66563) is a tetrahydroxyflavanone (CHEBI:38742)
IUPAC Name 
(2R,3R)-3,5,7-trihydroxy-2-[4-hydroxy-3-(3-methylbut-2-en-1-yl)phenyl]-6,8-bis(3-methylbut-2-en-1-yl)-2,3-dihydro-4H-chromen-4-one
Registry NumbersSources
Reaxys:19089538Reaxys
Citations