GtoPdb is requesting financial support from commercial users. Please see our sustainability page for more information.

zaragozic acid C   Click here for help

GtoPdb Ligand ID: 3073

Compound class: Natural product
Comment: Zaragozic acid C is produced by certain fungi. Total synthesis has also been reported [3].
Click here for help
2D Structure
Click here for help
Click here for structure editor
Physico-chemical Properties
Click here for help
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

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

SMILES / InChI / InChIKey
Click here for help
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

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

Bioactivity Comments
Zaragozic acid C is a potent inhibitor of bacterial, fungal and mammalian squalene synthases.
Selectivity at enzymes
Key to terms and symbols Click column headers to sort
Target Sp. Type Action Value Parameter Concentration range (M) Reference
squalene synthase Rn Inhibitor Inhibition 10.4 pKi - 1-2
pKi 10.4 (Ki 4.5x10-11 M) [1-2]
Description: Inhibition of rat squalene synthase
Conditions: Concentration of substrates: 0.2-10µM FPP, 10mM NADPH. pH 7.5, 30°C (8419946)