lucidenic acid N (CHEBI:66595)

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CHEBI:66595 - lucidenic acid N

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ChEBI ID	CHEBI:66595
ChEBI Name	lucidenic acid N
Stars
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.
Last Modified	25 March 2013
Downloads	Molfile

Formula	C27H40O6
Net Charge	0
Average Mass	460.611
Monoisotopic Mass	460.28249
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
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

Species of Metabolite	Component	Source	Comments
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:	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). metabolite Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
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 acid	ChEBI

Manual Xrefs	Databases
10213993	ChemSpider
HMDB0038352	HMDB

Registry Numbers	Sources
Reaxys:8956644	Reaxys

Citations