CHEBI:83934 - zaragozic acid C

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ChEBI Name zaragozic acid C
Definition A polyketide isolated from fungi that is a potent inhibitor of fungal and mammalian squalene synthase.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C40H50O14
Net Charge 0
Average Mass 754.81660
Monoisotopic Mass 754.32006
InChI InChI=1S/C40H50O14/c1-25(15-12-20-28-16-6-4-7-17-28)14-10-11-22-31(42)52-33-32(43)38(53-34(35(44)45)39(50,36(46)47)40(33,54-38)37(48)49)23-13-21-30(51-27(3)41)26(2)24-29-18-8-5-9-19-29/h4-10,14,16-19,25-26,30,32-34,43,50H,11-13,15,20-24H2,1-3H3,(H,44,45)(H,46,47)(H,48,49)/b14-10+/t25-,26+,30+,32+,33+,34+,38-,39+,40-/m0/s1
SMILES C[C@H](CCCc1ccccc1)\C=C\CCC(=O)O[C@@H]1[C@@H](O)[C@]2(CCC[C@@H](OC(C)=O)[C@H](C)Cc3ccccc3)O[C@@]1(C(O)=O)[C@@](O)([C@H](O2)C(O)=O)C(O)=O
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): EC (squalene synthase) inhibitor
An EC 2.5.1.* (non-methyl-alkyl or aryl transferase) inhibitor that interferes with the action of squalene synthase (EC
fungal metabolite
Any eukaryotic metabolite produced during a metabolic reaction in fungi, the kingdom that includes microorganisms such as the yeasts and moulds.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing zaragozic acid C (CHEBI:83934) has role EC (squalene synthase) inhibitor (CHEBI:75174)
zaragozic acid C (CHEBI:83934) has role fungal metabolite (CHEBI:76946)
zaragozic acid C (CHEBI:83934) is a acetate ester (CHEBI:47622)
zaragozic acid C (CHEBI:83934) is a cyclic ketal (CHEBI:59779)
zaragozic acid C (CHEBI:83934) is a oxabicycloalkane (CHEBI:46733)
zaragozic acid C (CHEBI:83934) is a polyketide (CHEBI:26188)
zaragozic acid C (CHEBI:83934) is a tertiary alcohol (CHEBI:26878)
zaragozic acid C (CHEBI:83934) is a tricarboxylic acid (CHEBI:27093)
(1S,3S,4S,5R,6R,7R)-1-[(4R,5R)-4-acetoxy-5-methyl-6-phenylhexyl]-4,7-dihydroxy-6-{[(4E,6R)-6-methyl-9-phenylnon-4-enoyl]oxy}-2,8-dioxabicyclo[3.2.1]octane-3,4,5-tricarboxylic acid
Synonyms Sources
(+)-Zaragozic acid ChemIDplus
L-697350 ChemIDplus
Manual Xref Database
CPD-4585 MetaCyc
View more database links
Registry Numbers Types Sources
146389-62-0 CAS Registry Number ChemIDplus
6839401 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
11031024 PubMed citation Europe PMC
14613174 PubMed citation Europe PMC
15635219 PubMed citation Europe PMC
16941713 PubMed citation Europe PMC
19053214 PubMed citation Europe PMC
Last Modified
28 November 2014