zaragozic acid A   Click here for help

GtoPdb Ligand ID: 3057

Synonyms: L 694599 | L-694599 | squalestatin | squalestatin 1
PDB Ligand
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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 19
Topological polar surface area 223.42
Molecular weight 690.29
XLogP 4.26
No. Lipinski's rules broken 2
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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
Selectivity at enzymes
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Target Sp. Type Action Value Parameter Concentration range (M) Reference
squalene synthase Rn Inhibitor Inhibition 10.1 pKi - 1
pKi 10.1 (Ki 7.8x10-11 M) [1]
Description: Compound was tested for inhibition of squalene synthase in rat liver.
Conditions: Concentration of substrates: 0.2-10µM FPP, 10mM NADPH. pH 7.5, 30°C
squalene synthase Hs Inhibitor Inhibition 9.6 pKi - 2
pKi 9.6 (Ki 2.5x10-10 M) [2]
Description: Human enzyme expressed in yeast, in vitro assay
Conditions: pH 7.4, 37°C
squalene synthase Hs Inhibitor Inhibition 9.1 pIC50 - 3
pIC50 9.1 (7x10-10 M) [3]
Description: in vitro, soluable microsomal enzymes purified from rat and human liver microsomes
Conditions: Concentration of FPP: 20µM