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CHEBI:66503 - zhankuic acid A

ChEBI IDCHEBI:66503
ChEBI Namezhankuic acid A
Stars
DefinitionA steroid acid that is ergosta-8,24(28)-dien-26-oic acid substituted by a methyl group at position 4 and oxo groups at positions 3, 7 and 11 (the 4α,5α stereoisomer). Isolated from Antrodia cinnamomea and Antrodia camphorata, it exhibits cytotoxic and anti-inflammatory activity.
Last Modified26 May 2015
DownloadsMolfile
FormulaC29H40O5
Net Charge0
Average Mass468.634
Monoisotopic Mass468.28757
SMILES[H][C@@]12CC[C@]([H])([C@H](C)CCC(=C)C(C)C(=O)O)[C@@]1(C)CC(=O)C1=C2C(=O)C[C@@]2([H])[C@H](C)C(=O)CC[C@]12C
InChIInChI=1S/C29H40O5/c1-15(17(3)27(33)34)7-8-16(2)19-9-10-20-25-23(31)13-21-18(4)22(30)11-12-28(21,5)26(25)24(32)14-29(19,20)6/h16-21H,1,7-14H2,2-6H3,(H,33,34)/t16-,17?,18+,19-,20+,21+,28+,29-/m1/s1
InChIKeyDVORYMAGXQGBQK-QCMFUGJUSA-N
Species of MetaboliteComponentSourceComments
Taiwanofungus camphoratus (ncbitaxon:196114)
fruit body (BTO:0000487) PubMed (15095145)
fruit body (BTO:0000487) PubMed (8594142)
fruit body (BTO:0000487) PubMed (21028898) Parasitic to the inner heartwood wall of old hollow trunks of Cinnamomum kanehirai, EtOH extract
Roles Classification
Chemical Role:
Bronsted acid  A molecular entity capable of donating a hydron to an acceptor (Brønsted base).
Biological Role:
plant metabolite  Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
Applications:
anti-inflammatory agent  Any compound that has anti-inflammatory effects.
antineoplastic agent  A substance that inhibits or prevents the proliferation of neoplasms.
ChEBI Ontology
Outgoing Relation(s)
zhankuic acid A (CHEBI:66503) has role anti-inflammatory agent (CHEBI:67079)
zhankuic acid A (CHEBI:66503) has role antineoplastic agent (CHEBI:35610)
zhankuic acid A (CHEBI:66503) has role plant metabolite (CHEBI:76924)
zhankuic acid A (CHEBI:66503) is a 11-oxo steroid (CHEBI:47787)
zhankuic acid A (CHEBI:66503) is a 3-oxo steroid (CHEBI:47788)
zhankuic acid A (CHEBI:66503) is a 7-oxo steroid (CHEBI:47789)
zhankuic acid A (CHEBI:66503) is a ergostanoid (CHEBI:50403)
zhankuic acid A (CHEBI:66503) is a monocarboxylic acid (CHEBI:25384)
zhankuic acid A (CHEBI:66503) is a steroid acid (CHEBI:47891)
Incoming Relation(s)
zhankuic acid A methyl ester (CHEBI:70310) has functional parent zhankuic acid A (CHEBI:66503)
IUPAC Name 
(4α,5α)-4-methyl-3,7,11-trioxoergosta-8,24(28)-dien-26-oic acid
Synonym  Source
4α-methylergosta-8,24(28)-dien-3,7,11-trione-26-oic acidChEBI
Registry NumbersSources
Reaxys:9824952Reaxys
Citations