CHEBI:75170 - zaragozic acid A

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ChEBI Name zaragozic acid A
ChEBI ID CHEBI:75170
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
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
InChIKey DFKDOZMCHOGOBR-NCSQYGPNSA-N
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 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.
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ChEBI Ontology
Outgoing zaragozic acid A (CHEBI:75170) has role EC 2.5.1.21 (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
Database Links Databases
LMPK00000001 LIPID MAPS
Zaragozic_acid Wikipedia
ZGA PDBeChem
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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 CiteXplore
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Last Modified
01 December 2014