CHEBI:83934 - zaragozic acid C

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ChEBI Name zaragozic acid C
ChEBI ID CHEBI:83934
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 ZINC000095615753
Download Molfile XML SDF
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
InChIKey KQMNJFMTGHRJHM-ZFSXNWTMSA-N
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 2.5.1.21 (squalene synthase) inhibitor
An EC 2.5.1.* (non-methyl-alkyl or aryl transferase) inhibitor that interferes with the action of squalene synthase (EC 2.5.1.21).
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 2.5.1.21 (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)
IUPAC Name
(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
Last Modified
28 November 2014