Zaragozic acid

Zaragozic acid A
Names
	Preferred IUPAC name (1S,3S,4S,5R,6R,7R)-1-[(4S,5R)-4-(Acetyloxy)-5-methyl-3-methylidene-6-phenylhexyl]-6-{[(2E,4S,6S)-4,6-dimethyloct-2-enoyl]oxy}-4,7-dihydroxy-2,8-dioxabicyclo[3.2.1]octane-3,4,5-tricarboxylic acid
	Other names Squalestatin 1
Identifiers
CAS Number	142561-96-4 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:75170 ;
ChEMBL	ChEMBL40991 ;
ChemSpider	4942838 ;
IUPHAR/BPS	3057;
PubChem CID	6438355;
UNII	1117HVX02L ;
CompTox Dashboard (EPA)	DTXSID701018091 ;
	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 Key: DFKDOZMCHOGOBR-NCSQYGPNSA-N ; InChI=1/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 Key: DFKDOZMCHOGOBR-NCSQYGPNBY;
	SMILES CC[C@H](C)C[C@H](C)/C=C/C(=O)O[C@@H]1[C@H]([C@]2(O[C@@H]([C@]([C@@]1(O2)C(=O)O)(C(=O)O)O)C(=O)O)CCC(=C)[C@H]([C@H](C)CC3=CC=CC=C3)OC(=O)C)O;
Properties
Chemical formula	C35H46O14
Molar mass	690.73134
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

Zaragozic acids are a family of natural products produced by fungi. The first characterized zaragozic acids, A, B, and C were isolated from an unidentified sterile fungal culture, Sporormiella intermedia, and L. elatius, respectively.^[1] just outside the European city Zaragoza, Spain on the Jalón river. This family of natural products possesses a unique 4,8-dioxabicyclo[3.2.1]octane core, and vary in their 1-alkyl and their 6-acyl side chains.^[2]

^ Bergstrom JD, Kurtz MM, Rew DJ, Amend AM, Karkas JD, Bostedor RG, Bansal VS, Dufresne C, VanMiddlesworth FL, Hensens OD (January 1993). "Zaragozic acids: a family of fungal metabolites that are picomolar competitive inhibitors of squalene synthase". Proc. Natl. Acad. Sci. U.S.A. 90 (1): 80–4. Bibcode:1993PNAS...90...80B. doi:10.1073/pnas.90.1.80. PMC 45603. PMID 8419946.
^ Bergstrom JD, Dufresne C, Bills GF, Nallin-Omstead M, Byrne K (1995). "Discovery, biosynthesis, and mechanism of action of the zaragozic acids: potent inhibitors of squalene synthase". Annu. Rev. Microbiol. 49: 607–39. doi:10.1146/annurev.mi.49.100195.003135. PMID 8561474.

[pmid8419946-1] Bergstrom JD, Kurtz MM, Rew DJ, Amend AM, Karkas JD, Bostedor RG, Bansal VS, Dufresne C, VanMiddlesworth FL, Hensens OD (January 1993). "Zaragozic acids: a family of fungal metabolites that are picomolar competitive inhibitors of squalene synthase". Proc. Natl. Acad. Sci. U.S.A. 90 (1): 80–4. Bibcode:1993PNAS...90...80B. doi:10.1073/pnas.90.1.80. PMC 45603. PMID 8419946.

[pmid8561474-2] Bergstrom JD, Dufresne C, Bills GF, Nallin-Omstead M, Byrne K (1995). "Discovery, biosynthesis, and mechanism of action of the zaragozic acids: potent inhibitors of squalene synthase". Annu. Rev. Microbiol. 49: 607–39. doi:10.1146/annurev.mi.49.100195.003135. PMID 8561474.

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