zaragozic acid C   Click here for help

GtoPdb Ligand ID: 3073

Compound class: Natural product
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 14
Hydrogen bond donors 5
Rotatable bonds 22
Topological polar surface area 223.42
Molecular weight 754.32
XLogP 5.72
No. Lipinski's rules broken 3
SMILES / InChI / InChIKey
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Canonical SMILES CC(CCCc1ccccc1)C=CCCC(=O)OC1C(O)C2(OC1(C(=O)O)C(O)(C(=O)O)C(O2)C(=O)O)CCCC(C(Cc1ccccc1)C)OC(=O)C
Isomeric SMILES C[C@H](CCCc1ccccc1)/C=C/CCC(=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@H]([C@@H](Cc1ccccc1)C)OC(=O)C
InChI InChI=1S/C40H50O14/c1-25(15-12-20-28-16-6-4-7-17-28)14-10-11-22-31(42)52-33-32(43)38(53-34(35(44)45)39(50,36(46)47)40(33,54-38)37(48)49)23-13-21-30(51-27(3)41)26(2)24-29-18-8-5-9-19-29/h4-10,14,16-19,25-26,30,32-34,43,50H,11-13,15,20-24H2,1-3H3,(H,44,45)(H,46,47)(H,48,49)/b14-10+/t25-,26+,30+,32+,33+,34+,38-,39+,40-/m0/s1
InChI Key KQMNJFMTGHRJHM-ZFSXNWTMSA-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 USA, 90 (1): 80-4. [PMID:8419946]
2. Dufresne C, Wilson KE, Zink D, Smith J, Bergstrom JD, Kurtz M, Rew D, Nallin M, Jenkins R, Bartizal K, Trainor C, Bills G, Meinz M, Huang L, Onishi J, Milligan J, Mojena M, Pelaez F. (1992)
The Isolation and Structure Elucidation of Zaragozic Acid C, a Novel Potent Squalene Synthase Inhibitor.
Tetrahedron, 48 (41): 10221-10226.