CHEBI:66595 - lucidenic acid N

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ChEBI Name lucidenic acid N
ChEBI ID CHEBI:66595
Definition A tetracyclic triterpenoid that is 25,26,27-trinorlanost-8-en-24-oic acid substituted by hydroxy groups at positions 3 and 7 and oxo groups at positions 11 and 15 respectively (the 3β,5α,7β stereoisomer). Isolated from the fruiting bodies of Ganoderma lucidum, it exhibits cytotoxicity against tumour cells.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C27H40O6
Net Charge 0
Average Mass 460.60290
Monoisotopic Mass 460.28249
InChI InChI=1S/C27H40O6/c1-14(7-8-21(32)33)15-11-20(31)27(6)23-16(28)12-18-24(2,3)19(30)9-10-25(18,4)22(23)17(29)13-26(15,27)5/h14-16,18-19,28,30H,7-13H2,1-6H3,(H,32,33)/t14-,15-,16+,18+,19+,25+,26-,27+/m1/s1
InChIKey YBGBNHHXOJXFNM-UQCMLMITSA-N
SMILES [H][C@@]1(CC(=O)[C@@]2(C)C3=C(C(=O)C[C@]12C)[C@@]1(C)CC[C@H](O)C(C)(C)[C@]1([H])C[C@@H]3O)[C@H](C)CCC(O)=O
Metabolite of Species Details
Ganoderma lucidum (NCBI:txid5315) Found in fruit body (BTO:0000487). 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.
EC 3.1.1.8 (cholinesterase) inhibitor
An EC 3.1.1.* (carboxylic ester hydrolase) inhibitor that interferes with the action of cholinesterase (EC 3.1.1.8).
Application(s): antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing lucidenic acid N (CHEBI:66595) has role antineoplastic agent (CHEBI:35610)
lucidenic acid N (CHEBI:66595) has role EC 3.1.1.8 (cholinesterase) inhibitor (CHEBI:37733)
lucidenic acid N (CHEBI:66595) has role metabolite (CHEBI:25212)
lucidenic acid N (CHEBI:66595) is a cyclic terpene ketone (CHEBI:36130)
lucidenic acid N (CHEBI:66595) is a dioxo monocarboxylic acid (CHEBI:35951)
lucidenic acid N (CHEBI:66595) is a secondary alcohol (CHEBI:35681)
lucidenic acid N (CHEBI:66595) is a tetracyclic triterpenoid (CHEBI:26893)
IUPAC Name
(3β,5α,7β)-3,7-dihydroxy-4,4,14-trimethyl-11,15-dioxochol-8-en-24-oic acid
Synonym Source
3,7-Dihydroxy-25,26,27-trinor-11,15-dioxolanost-8-en-24-oic acid ChEBI
Manual Xrefs Databases
10213993 ChemSpider
HMDB0038352 HMDB
View more database links
Registry Number Type Source
8956644 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
11520245 PubMed citation Europe PMC
18422750 PubMed citation Europe PMC
21924611 PubMed citation Europe PMC
Last Modified
25 March 2013