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CHEBI:67312 - 17-defurano-17-oxosalannin

ChEBI IDCHEBI:67312
ChEBI Name17-defurano-17-oxosalannin
Stars
DefinitionA limonoid that is salannin in which the furanyl group at position 17 is replaced by an oxo group. Isolated from Azadirachta indica, it exhibits anti-inflammatory activity.
Last Modified3 March 2015
DownloadsMolfile
FormulaC30H40O9
Net Charge0
Average Mass544.641
Monoisotopic Mass544.26723
SMILES[H][C@]12OC[C@]3(C)[C@H](OC(C)=O)C[C@H](OC(=O)/C(C)=C/C)[C@](C)([C@@H](CC(=O)OC)[C@]4(C)C5=C(C)C(=O)C[C@@]5([H])O[C@]14[H])[C@@]23[H]
InChIInChI=1S/C30H40O9/c1-9-14(2)27(34)39-21-12-20(37-16(4)31)28(5)13-36-24-25(28)29(21,6)19(11-22(33)35-8)30(7)23-15(3)17(32)10-18(23)38-26(24)30/h9,18-21,24-26H,10-13H2,1-8H3/b14-9+/t18-,19-,20-,21+,24-,25+,26-,28-,29+,30-/m1/s1
InChIKeyLGQIDAUSKKGKHE-RYKSROFQSA-N
Species of MetaboliteComponentSourceComments
Azadirachta indica (ncbitaxon:124943) seed (BTO:0001226) PubMed (21381696) n-Hexane extract of seeds
Roles Classification
Application:
anti-inflammatory agent  Any compound that has anti-inflammatory effects.
ChEBI Ontology
Outgoing Relation(s)
17-defurano-17-oxosalannin (CHEBI:67312) has functional parent salannin (CHEBI:67309)
17-defurano-17-oxosalannin (CHEBI:67312) has functional parent tiglic acid (CHEBI:9592)
17-defurano-17-oxosalannin (CHEBI:67312) has role anti-inflammatory agent (CHEBI:67079)
17-defurano-17-oxosalannin (CHEBI:67312) is a acetate ester (CHEBI:47622)
17-defurano-17-oxosalannin (CHEBI:67312) is a cyclic terpene ketone (CHEBI:36130)
17-defurano-17-oxosalannin (CHEBI:67312) is a enone (CHEBI:51689)
17-defurano-17-oxosalannin (CHEBI:67312) is a limonoid (CHEBI:39434)
17-defurano-17-oxosalannin (CHEBI:67312) is a methyl ester (CHEBI:25248)
17-defurano-17-oxosalannin (CHEBI:67312) is a organic heteropentacyclic compound (CHEBI:38164)
IUPAC Name 
(2aR,3R,5S,5aR,6R,6aR,9aR,10aS,10bR,10cR)-3-(acetyloxy)-6-(2-methoxy-2-oxoethyl)-2a,5a,6a,7-tetramethyl-8-oxo-2a,4,5,5a,6,6a,8,9,9a,10a,10b,10c-dodecahydro-2H,3H-cyclopenta[d]naphtho[2,3-b:1,8-b'c']difuran-5-yl (2E)-2-methylbut-2-enoate
Registry NumbersSources
Reaxys:21448582Reaxys
Citations