zaragozic acid A   

GtoPdb Ligand ID: 3057

Synonyms: L 694599 | L-694599 | squalestatin | squalestatin 1
2D Structure
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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
Classification
Compound class Natural product or derivative
IUPAC Name
(1S,3S,4S,5R,6R,7R)-1-[(4S,5R)-4-(acetyloxy)-5-benzyl-3-methylidenehexyl]-6-{[(2E,4S,6S)-4,6-dimethyloct-2-enoyl]oxy}-4,7-dihydroxy-2,8-dioxabicyclo[3.2.1]octane-3,4,5-tricarboxylic acid
Synonyms
L 694599 | L-694599 | squalestatin | squalestatin 1
Database Links
CAS Registry No. 142561-96-4 (source: Scifinder)
ChEBI CHEBI:75170
ChEMBL Ligand CHEMBL280978
GtoPdb PubChem SID 135652728
PubChem CID 6438355
RCSB PDB Ligand ZGA
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SynPHARM 6997 (in complex with squalene synthase )
6998 (in complex with squalene synthase )
Wikipedia Zaragozic_acid