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CHEBI:66595 - lucidenic acid N

Default Structure
ChEBI IDCHEBI:66595
ChEBI Namelucidenic acid N
Stars
DefinitionA 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.
Last Modified25 March 2013
DownloadsMolfile
FormulaC27H40O6
Net Charge0
Average Mass460.611
Monoisotopic Mass460.28249
SMILES[H][C@@]12C[C@H](O)C3=C(C(=O)C[C@@]4(C)[C@@]3(C)C(=O)C[C@]4([H])[C@H](C)CCC(=O)O)[C@@]1(C)CC[C@H](O)C2(C)C
InChIInChI=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
InChIKeyYBGBNHHXOJXFNM-UQCMLMITSA-N
Species of MetaboliteComponentSourceComments
Ganoderma lucidum (ncbitaxon:5315) fruit body (BTO:0000487) PubMed (11520245)
Roles Classification
Chemical Role:
Bronsted acid  A molecular entity capable of donating a hydron to an acceptor (Brønsted base).
Biological Roles:
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:
antineoplastic agent  A substance that inhibits or prevents the proliferation of neoplasms.
ChEBI Ontology
Outgoing Relation(s)
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 acidChEBI
Manual XrefsDatabases
10213993ChemSpider
HMDB0038352HMDB
Registry NumbersSources
Reaxys:8956644Reaxys
Citations