zaragozic acid A   

GtoPdb Ligand ID: 3057

Synonyms: L 694599 | L-694599 | squalestatin | squalestatin 1
2D Structure
Click here for structure editor
Physico-chemical Properties
Hydrogen bond acceptors 14
Hydrogen bond donors 5
Rotatable bonds 19
Topological polar surface area 223.42
Molecular weight 690.29
XLogP 4.26
No. Lipinski's rules broken 2
SMILES / InChI / InChIKey
Canonical SMILES CCC(CC(C=CC(=O)OC1C(O)C2(OC1(C(=O)O)C(O)(C(=O)O)C(O2)C(=O)O)CCC(=C)C(C(Cc1ccccc1)C)OC(=O)C)C)C
Isomeric SMILES CC[C@@H](C[C@@H](/C=C/C(=O)O[C@@H]1[C@@H](O)[C@@]2(O[C@@]1(C(=O)O)[C@](O)(C(=O)O)[C@H](O2)C(=O)O)CCC(=C)[C@H]([C@@H](Cc1ccccc1)C)OC(=O)C)C)C
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
InChI Key DFKDOZMCHOGOBR-NCSQYGPNSA-N
References
1. Bergstrom JD, Kurtz MM, Rew DJ, Amend AM, Karkas JD, Bostedor RG, Bansal VS, Dufresne C, VanMiddlesworth FL, Hensens OD. (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. [PMID:8419946]
2. Soltis DA, McMahon G, Caplan SL, Dudas DA, Chamberlin HA, Vattay A, Dottavio D, Rucker ML, Engstrom RG, Cornell-Kennon SA. (1995)
Expression, purification, and characterization of the human squalene synthase: use of yeast and baculoviral systems.
Arch. Biochem. Biophys., 316 (2): 713-23. [PMID:7864626]
3. Thompson JF, Danley DE, Mazzalupo S, Milos PM, Lira ME, Harwood HJ. (1998)
Truncation of human squalene synthase yields active, crystallizable protein.
Arch. Biochem. Biophys., 350 (2): 283-90. [PMID:9473303]