CHEBI:66321 - weigelic acid

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ChEBI Name weigelic acid
ChEBI ID CHEBI:66321
Definition A 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.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C30H48O6
Net Charge 0
Average Mass 504.69850
Monoisotopic Mass 504.34509
InChI InChI=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
InChIKey NFPZOORPDJBGME-BLOZSHLCSA-N
SMILES [H][C@@]12CC[C@]3(C)[C@]([H])(CC=C4[C@]5([H])[C@@H](C)[C@H](C)CC[C@@]5(CC[C@@]34C)C(O)=O)[C@@]1(C)[C@H](O)[C@@H](O)[C@@H](O)[C@@]2(C)CO
Metabolite of Species Details
Weigela subsessilis (NCBI:txid79620) Found in leaf (BTO:0000713). See: PubMed
Weigela subsessilis (NCBI:txid79620) Found in stem (BTO:0001300). See: PubMed
Roles Classification
Chemical Role(s): Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
Biological Role(s): metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
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ChEBI Ontology
Outgoing 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 Xref Database
8777001 ChemSpider
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Registry Number Type Source
10508037 Reaxys Registry Number Reaxys
Citation Waiting for Citations Type Source
16595930 PubMed citation Europe PMC
Last Modified
14 April 2020