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CHEBI:66260 - trachyspic acid

ChEBI IDCHEBI:66260
ChEBI Nametrachyspic acid
Stars
DefinitionAn oxaspiro compound that is 1,6-dioxaspiro[4.4]non-2-en-4-one substituted by a carboxymethyl group at position 2, carboxy groups at positions 2 and 3, an oxo group at position 9 and a nonyl group at position 8. Isolated from the culture broth of the fungus Talaromyces trachyspermus, it exhibits inhibitory activity against the enzyme heparanase.
Last Modified26 November 2014
DownloadsMolfile
FormulaC20H28O9
Net Charge0
Average Mass412.435
Monoisotopic Mass412.17333
SMILESCCCCCCCCCC1=COC2(CC(C(=O)O)C(CC(=O)O)(C(=O)O)O2)C1=O
InChIInChI=1S/C20H28O9/c1-2-3-4-5-6-7-8-9-13-12-28-20(16(13)23)10-14(17(24)25)19(29-20,18(26)27)11-15(21)22/h12,14H,2-11H2,1H3,(H,21,22)(H,24,25)(H,26,27)
InChIKeyLQLCHKHILFZNKF-UHFFFAOYSA-N
Wikipedia
Species of MetaboliteComponentSourceComments
Talaromyces trachyspermus (ncbitaxon:28566) - PubMed (7797435) Strain: SANK 12191
Roles Classification
Chemical Role:
Bronsted acid  A molecular entity capable of donating a hydron to an acceptor (Brønsted base).
Biological Roles:
fungal metabolite  Any eukaryotic metabolite produced during a metabolic reaction in fungi, the kingdom that includes microorganisms such as the yeasts and moulds.
EC 3.2.1.166 (heparanase) inhibitor  An EC 3.2.1.* (glycosidase) inhibitor that interferes with the action of heparanase (EC 3.2.1.166).
ChEBI Ontology
Outgoing Relation(s)
trachyspic acid (CHEBI:66260) has role EC 3.2.1.166 (heparanase) inhibitor (CHEBI:64955)
trachyspic acid (CHEBI:66260) has role fungal metabolite (CHEBI:76946)
trachyspic acid (CHEBI:66260) is a oxaspiro compound (CHEBI:37948)
trachyspic acid (CHEBI:66260) is a tricarboxylic acid (CHEBI:27093)
IUPAC Name 
2-(carboxymethyl)-8-nonyl-9-oxo-1,6-dioxaspiro[4.4]non-7-ene-2,3-dicarboxylic acid
Manual XrefsDatabases
Trachyspic_acidWikipedia
Registry NumbersSources
Reaxys:7318108Reaxys
CAS:149718-37-6ChemIDplus
Citations