CHEBI:66260 - trachyspic acid

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ChEBI Name trachyspic acid
ChEBI ID CHEBI:66260
Definition An 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.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C20H28O9
Net Charge 0
Average Mass 412.43090
Monoisotopic Mass 412.17333
InChI InChI=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)
InChIKey LQLCHKHILFZNKF-UHFFFAOYSA-N
SMILES CCCCCCCCCC1=COC2(CC(C(O)=O)C(CC(O)=O)(O2)C(O)=O)C1=O
Metabolite of Species Details
Talaromyces trachyspermus (NCBI:txid28566) of strain SANK 12191 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): 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).
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ChEBI Ontology
Outgoing 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 Xref Database
Trachyspic_acid Wikipedia
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Registry Numbers Types Sources
149718-37-6 CAS Registry Number ChemIDplus
7318108 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
12633090 PubMed citation Europe PMC
15917891 PubMed citation Europe PMC
17700851 PubMed citation Europe PMC
21879704 PubMed citation Europe PMC
7797435 PubMed citation Europe PMC
Last Modified
26 November 2014