CHEBI:75170 - zaragozic acid A

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ChEBI Name zaragozic acid A
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.
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Formula C35H46O14
Net Charge 0
Average Mass 690.73130
Monoisotopic Mass 690.28876
InChI InChI=1S/C35H46O14/c1-7-19(2)17-20(3)13-14-25(37)47-28-27(38)33(48-29(30(39)40)34(45,31(41)42)35(28,49-33)32(43)44)16-15-21(4)26(46-23(6)36)22(5)18-24-11-9-8-10-12-24/h8-14,19-20,22,26-29,38,45H,4,7,15-18H2,1-3,5-6H3,(H,39,40)(H,41,42)(H,43,44)/b14-13+/t19-,20+,22+,26+,27+,28+,29+,33-,34+,35-/m0/s1
SMILES CC[C@H](C)C[C@H](C)\C=C\C(=O)O[C@@H]1[C@@H](O)[C@@]2(CCC(=C)[C@@H](OC(C)=O)[C@H](C)Cc3ccccc3)O[C@H](C(O)=O)[C@@](O)(C(O)=O)[C@@]1(O2)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.
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ChEBI Ontology
Outgoing zaragozic acid A (CHEBI:75170) has role EC (squalene synthase) inhibitor (CHEBI:75174)
zaragozic acid A (CHEBI:75170) has role fungal metabolite (CHEBI:76946)
zaragozic acid A (CHEBI:75170) is a acetate ester (CHEBI:47622)
zaragozic acid A (CHEBI:75170) is a cyclic ketal (CHEBI:59779)
zaragozic acid A (CHEBI:75170) is a oxabicycloalkane (CHEBI:46733)
zaragozic acid A (CHEBI:75170) is a polyketide (CHEBI:26188)
zaragozic acid A (CHEBI:75170) is a tertiary alcohol (CHEBI:26878)
zaragozic acid A (CHEBI:75170) is a tricarboxylic acid (CHEBI:27093)
Incoming zaragozic acid A derivative (CHEBI:83961) has functional parent zaragozic acid A (CHEBI:75170)
Synonyms Sources
1S-((4S-acetoxy-5R-methyl-3-methylene-6-phenylhexyl)-6-(E)-4S,6S-dimethyloct-2-enoyloxy)-4,7S-dihydroxy-2,8-dioxabicyclo[3.2.1]octane-3S,4S,5R-tricarboxylic acid LIPID MAPS
Squalestatin 1 ChEBI
Manual Xrefs Databases
Zaragozic_acid Wikipedia
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Registry Numbers Types Sources
142561-96-4 CAS Registry Number ChemIDplus
5848265 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
10987953 PubMed citation Europe PMC
12391282 PubMed citation Europe PMC
1601846 PubMed citation Europe PMC
20722739 PubMed citation Europe PMC
21183681 PubMed citation Europe PMC
22474324 PubMed citation Europe PMC
23485731 PubMed citation Europe PMC
7811707 PubMed citation Europe PMC
8002393 PubMed citation Europe PMC
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9647670 PubMed citation Europe PMC
9730906 PubMed citation Europe PMC
Last Modified
01 December 2014