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Zaragozic acid A

CAT: 0804-HY-116290Size: 1 mgDry Ice: NoHazardous: No
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CAT#:0804-HY-116290Size:1 mg
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Description
Zaragozic acid A is a fungal metabolite that acts as a reversible competitive inhibitor of squalene synthase. Zaragozic acid A is an inhibitor of acute hepatic cholesterol synthesis in mouse (IC50 = 6 μM) [1].
CAS Number
142561-96-4
Product Name Alternative
Squalestatin S1
UNSPSC
12352005
Target
Endogenous Metabolite
Type
Natural Products
Related Pathways
Metabolic Enzyme/Protease
Field of Research
Metabolic Disease
Assay Protocol
https://www.medchemexpress.com/zaragozic-acid-a.html
Purity
99.2
Solubility
H2O : 1 mg/mL (ultrasonic; warming)
Smiles
CC[C@@H](C[C@@H](/C=C/C(O[C@@H]1[C@H]([C@]2(O[C@@H]([C@@](C(O)=O)([C@]1(C(O)=O)O2)O)C(O)=O)CCC([C@H]([C@@H](CC3=CC=CC=C3)C)OC(C)=O)=C)O)=O)C)C
Molecular Formula
C35H46O14
Molecular Weight
690.73
References & Citations
[1]J D Bergstrom, et al. Zaragozic acids: a family of fungal metabolites that are picomolar competitive inhibitors of squalene synthase. Proc Natl Acad Sci U S A. 1993 Jan 1;90 (1) :80-4.
Shipping Conditions
Blue Ice
Storage Conditions
-20°C (Powder, sealed storage, away from moisture)
Scientific Category
Natural Products
Clinical Information
No Development Reported

Chemical Information

Zaragozic Acid A

Zaragozic acid A is a polyketide, a tertiary alcohol, a tricarboxylic acid, an oxabicycloalkane, an acetate ester and a cyclic ketal. It has a role as an EC 2.5.1.21 (squalene synthase) inhibitor and a fungal metabolite.

CAS Number142561-96-4
PubChem CID6438355
IUPAC Name(1S,3S,4S,5R,6R,7R)-1-[(4S,5R)-4-acetyloxy-5-methyl-3-methylidene-6-phenylhexyl]-6-[(E,4S,6S)-4,6-dimethyloct-2-enoyl]oxy-4,7-dihydroxy-2,8-dioxabicyclo[3.2.1]octane-3,4,5-tricarboxylic acid
Molecular FormulaC35H46O14
Molecular Weight690.7
XLogP4.9
Topological Polar Surface Area223
Hydrogen Bond Donor Count5
Hydrogen Bond Acceptor Count14
Rotatable Bond Count19
Heavy Atom Count49
Formal Charge0
Complexity1290
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
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
Chemical Structure
2D Structure
2D structure of Zaragozic Acid A
CAS: 142561-96-4
CID: 6438355
Formula: C35H46O14
MW: 690.7
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight690.7
XLogP34.9
Hydrogen Bond Donor Count5
Hydrogen Bond Acceptor Count14
Rotatable Bond Count19
Exact Mass690.28875614
Monoisotopic Mass690.28875614
Topological Polar Surface Area223 Ų
Heavy Atom Count49
Formal Charge0
Complexity1290
Isotope Atom Count0
Defined Atom Stereocenter Count10
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count1
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

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