TGN4   Click here for help

GtoPdb Ligand ID: 8822

Compound class: Synthetic organic
Comment: TGN4 is a thapsigargin analogue designed as an allosteric inhibitor of the sarcoplasmic/endoplasmic reticulum calcium-ATPase (SERCA) [1]. Like thapsigargin, TGN4 disrupts calcium transport by binding to a hydrophobic pocket located in the transmembrane region of SERCA.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 16
Hydrogen bond donors 5
Rotatable bonds 29
Topological polar surface area 255.15
Molecular weight 822.45
XLogP 3.42
No. Lipinski's rules broken 2
SMILES / InChI / InChIKey
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Canonical SMILES CCCCCCCC(=O)OC1C(=O)C(=C2C1C(C)(OC(=O)C)CC(C1(C2OC(=O)C1(C)O)O)OC(=O)CCCCCCCCCCCNC(=O)CCC(C(=O)O)N)C
Isomeric SMILES CCCCCCCC(=O)O[C@@H]1C(=O)C(=C2[C@H]1[C@@](C)(OC(=O)C)C[C@@H]([C@]1([C@H]2OC(=O)[C@@]1(C)O)O)OC(=O)CCCCCCCCCCCNC(=O)CCC(C(=O)O)N)C
InChI InChI=1S/C42H66N2O14/c1-6-7-8-14-17-21-32(48)56-36-34-33(26(2)35(36)49)37-42(54,41(5,53)39(52)57-37)29(25-40(34,4)58-27(3)45)55-31(47)20-18-15-12-10-9-11-13-16-19-24-44-30(46)23-22-28(43)38(50)51/h28-29,34,36-37,53-54H,6-25,43H2,1-5H3,(H,44,46)(H,50,51)/t28?,29-,34+,36-,37-,40-,41+,42+/m0/s1
InChI Key WSISVGWHSKNHQQ-JEWAQKBPSA-N
Classification Click here for help
Compound class Synthetic organic
IUPAC Name Click here for help
5-[[12-[[(3S,3aR,4S,6S,6aR,7S,9bS)-6-acetyloxy-3,3a-dihydroxy-3,6,9-trimethyl-7-octanoyloxy-2,8-dioxo-5,6a,7,9b-tetrahydro-4H-azuleno[4,5-b]furan-4-yl]oxy]-12-oxododecyl]amino]-2-amino-5-oxopentanoic acid
Database Links Click here for help
ChEMBL Ligand CHEMBL365703
GtoPdb PubChem SID 252827479
PubChem CID 11457116
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