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CHEBI:75170 - zaragozic acid A

ChEBI IDCHEBI:75170
ChEBI Namezaragozic acid A
Stars
DefinitionA polyketide isolated from fungi that is a potent inhibitor of fungal and mammalian squalene synthase.
Last Modified1 December 2014
SubmitterSteve
DownloadsMolfile
FormulaC35H46O14
Net Charge0
Average Mass690.739
Monoisotopic Mass690.28876
SMILESC=C(CC[C@]12O[C@H](C(=O)O)[C@@](O)(C(=O)O)[C@](C(=O)O)(O1)[C@H](OC(=O)/C=C/[C@@H](C)C[C@@H](C)CC)[C@H]2O)[C@@H](OC(C)=O)[C@H](C)Cc1ccccc1
InChIInChI=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
InChIKeyDFKDOZMCHOGOBR-NCSQYGPNSA-N
Wikipedia
Roles Classification
Chemical Role:
Bronsted acid  A molecular entity capable of donating a hydron to an acceptor (Brønsted base).
Biological Roles:
fungal metabolite  Any eukaryotic metabolite produced during a metabolic reaction in fungi, the kingdom that includes microorganisms such as the yeasts and moulds.
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).
ChEBI Ontology
Outgoing Relation(s)
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 Relation(s)
zaragozic acid A derivative (CHEBI:83961) has functional parent zaragozic acid A (CHEBI:75170)
Synonyms  Source
Squalestatin 1ChEBI
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 acidLIPID MAPS
Manual XrefsDatabases
LMPK00000001LIPID MAPS
ZGAPDBeChem
Zaragozic_acidWikipedia
Registry NumbersSources
Reaxys:5848265Reaxys
CAS:142561-96-4ChemIDplus
Citations