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CHEBI:67853 - pescaprein XXIII

ChEBI IDCHEBI:67853
ChEBI Namepescaprein XXIII
Stars
DefinitionA resin glycoside that is the pentasaccharide derivative of jalapinolic acid. Isolated from the aerial parts of Ipomoea pes-caprae, it has been found to exhibit potential inhibitory effect against multidrug resistance in the human breast cancer cell line.
Last Modified3 September 2015
DownloadsMolfile
FormulaC70H112O25
Net Charge0
Average Mass1353.641
Monoisotopic Mass1352.74927
SMILES[H][C@@]1(O[C@@H]2[C@@H](O[C@]3([H])O[C@@H](C)[C@H](OC(=O)[C@@H](C)CC)[C@@H](OC(=O)/C=C/c4ccccc4)[C@H]3O)[C@H](C)O[C@@H](O[C@@]3([H])[C@H](C)O[C@H]4O[C@@]5([H])[C@H](O[C@@H](CCCCC)CCCCCCCCCC(=O)O[C@H]3[C@H]4O)O[C@H](C)[C@H](O)[C@@H]5O)[C@@H]2OC(=O)CCCCCCCCC)O[C@@H](C)[C@H](O)[C@@H](O)[C@H]1O
InChIInChI=1S/C70H112O25/c1-10-13-15-16-18-22-30-36-48(72)90-64-63(95-66-54(78)52(76)50(74)40(5)82-66)59(92-67-55(79)60(57(42(7)84-67)91-65(81)39(4)12-3)89-49(73)38-37-45-31-26-24-27-32-45)44(9)86-70(64)93-58-43(8)85-68-56(80)61(58)88-47(71)35-29-23-20-17-19-21-28-34-46(33-25-14-11-2)87-69-62(94-68)53(77)51(75)41(6)83-69/h24,26-27,31-32,37-44,46,50-64,66-70,74-80H,10-23,25,28-30,33-36H2,1-9H3/b38-37+/t39-,40-,41+,42-,43-,44-,46-,50-,51-,52+,53-,54+,55+,56+,57-,58-,59-,60-,61-,62+,63+,64+,66-,67-,68-,69-,70-/m0/s1
InChIKeyVCBSNBJPLWMYQG-JEENFSGDSA-N
Species of MetaboliteComponentSourceComments
Ipomoea pes-caprae (ncbitaxon:89656) aerial part (BTO:0001658) PubMed (21338052) The air-dried aerial parts were powdered and refluxed with 95% EtOH
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.
ChEBI Ontology
Outgoing Relation(s)
pescaprein XXIII (CHEBI:67853) has functional parent (S)-2-methylbutyric acid (CHEBI:38655)
pescaprein XXIII (CHEBI:67853) has functional parent trans-cinnamic acid (CHEBI:35697)
pescaprein XXIII (CHEBI:67853) has functional parent jalapinolic acid (CHEBI:75785)
pescaprein XXIII (CHEBI:67853) has role metabolite (CHEBI:25212)
pescaprein XXIII (CHEBI:67853) is a cinnamate ester (CHEBI:36087)
pescaprein XXIII (CHEBI:67853) is a decanoate ester (CHEBI:87658)
pescaprein XXIII (CHEBI:67853) is a macrocyclic lactone (CHEBI:63944)
pescaprein XXIII (CHEBI:67853) is a pentasaccharide derivative (CHEBI:63566)
pescaprein XXIII (CHEBI:67853) is a resin glycoside (CHEBI:75756)
Synonym  Source
(11S)-jalapinolic acid 11-O-α-L-rhamnopyranosyl-(1→3)-O-[3-O-(trans-cinnamoyl)-4-O-(2S-methylbutanoyl)-α-L-rhamnopyranosyl-(1→4)]-O-[2-O-n-decanoyl]-α-L-rhamnopyranosyl-(1→4)-α-L-rhamnopyranosyl-(1→2)-O-β-D-fucopyranoside-(1,3''-lactone)ChEBI
Registry NumbersSources
Reaxys:21523283Reaxys
Citations