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CHEBI:66321 - weigelic acid

ChEBI IDCHEBI:66321
ChEBI Nameweigelic acid
Stars
DefinitionA pentacyclic triterpenoid that is urs-12-ene substituted by hydroxy groups at positions 1, 2, 3 and 23 and a carboxy group at position 28 (the 1β,2α,3α stereoisomer). Isolated from Weigela subsessilis, it exhibits anticomplement activity against complement induced hemolysis.
Last Modified14 April 2020
DownloadsMolfile
FormulaC30H48O6
Net Charge0
Average Mass504.708
Monoisotopic Mass504.34509
SMILES[H][C@]12CC=C3[C@@](C)(CC[C@@]4(C(=O)O)CC[C@@H](C)[C@H](C)[C@@]34[H])[C@]1(C)CC[C@]1([H])[C@]2(C)[C@H](O)[C@@H](O)[C@@H](O)[C@@]1(C)CO
InChIInChI=1S/C30H48O6/c1-16-9-12-30(25(35)36)14-13-27(4)18(21(30)17(16)2)7-8-20-28(27,5)11-10-19-26(3,15-31)23(33)22(32)24(34)29(19,20)6/h7,16-17,19-24,31-34H,8-15H2,1-6H3,(H,35,36)/t16-,17+,19+,20+,21+,22+,23-,24-,26+,27-,28-,29+,30+/m1/s1
InChIKeyNFPZOORPDJBGME-BLOZSHLCSA-N
Species of MetaboliteComponentSourceComments
Weigela subsessilis (ncbitaxon:79620)
stem (BTO:0001300) PubMed (16595930)
leaf (BTO:0000713) PubMed (16595930)
Roles Classification
Chemical Role:
Bronsted acid  A molecular entity capable of donating a hydron to an acceptor (Brønsted base).
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)
weigelic acid (CHEBI:66321) has parent hydride ursane (CHEBI:35711)
weigelic acid (CHEBI:66321) has role metabolite (CHEBI:25212)
weigelic acid (CHEBI:66321) is a monocarboxylic acid (CHEBI:25384)
weigelic acid (CHEBI:66321) is a pentacyclic triterpenoid (CHEBI:25872)
weigelic acid (CHEBI:66321) is a tetrol (CHEBI:33573)
IUPAC Name 
(1β,2α,3α)-1,2,3,23-tetrahydroxyurs-12-en-28-oic acid
Manual XrefsDatabases
8777001ChemSpider
Registry NumbersSources
Reaxys:10508037Reaxys
Citations