retaspimycin hydrochloride   Click here for help

GtoPdb Ligand ID: 9827

Synonyms: 17-AAG (hydrochloride) | 17-Allylamino-17-demethoxygeldanamycin (hydrochloride) | IPI-504 | IPI504
Compound class: Synthetic organic
Comment: 17-Allylamino-17-demethoxygeldanamycin (17-AAG)1 is a semisynthetic inhibitor of the 90 kDa heat shock protein (Hsp90) currently in clinical trials for the treatment of cancer. However, 17-AAG faces challenging formulation issues due to its poor solubility. The synthesis and evaluation of a highly soluble hydroquinone hydrochloride derivative of 17-AAG, 1a (IPI-504) was reported in [1]. A Phase I trial indicated this was well-tolerated with some evidence of antitumor activity, serving as a clinical proof-of-concept that HSP90 inhibition remains promising [2]. Note this ligand entry is an exception to our general rule of salt-stripping because it is clear in this case that the hydorchoride is being used. The parent structure is PubChem CID 11534420.
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2D Structure
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SMILES / InChI / InChIKey
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Canonical SMILES C=CCNc1c(O)cc2c(c1CC(C)CC(OC)C(O)C(C)C=C(C)C(C(C=CC=C(C(=O)N2)C)OC)OC(=O)N)O.Cl
Isomeric SMILES C=CCNc1c(O)cc2c(c1C[C@@H](C)C[C@H](OC)[C@H](O)[C@@H](C)/C=C(\C)/[C@@H]([C@H](/C=C\C=C(\C(=O)N2)/C)OC)OC(=O)N)O.Cl
InChI InChI=1S/C31H45N3O8.ClH/c1-8-12-33-26-21-13-17(2)14-25(41-7)27(36)19(4)15-20(5)29(42-31(32)39)24(40-6)11-9-10-18(3)30(38)34-22(28(21)37)16-23(26)35;/h8-11,15-17,19,24-25,27,29,33,35-37H,1,12-14H2,2-7H3,(H2,32,39)(H,34,38);1H/b11-9-,18-10+,20-15+;/t17-,19+,24+,25+,27-,29+;/m1./s1
InChI Key OIRUWDYJGMHDHJ-AFXVCOSJSA-N
Classification Click here for help
Compound class Synthetic organic
IUPAC Name Click here for help
[(3R,5S,6R,7S,8E,10S,11S,12Z,14E)-6,20,22-trihydroxy-5,11-dimethoxy-3,7,9,15-tetramethyl-16-oxo-21-(prop-2-enylamino)-17-azabicyclo[16.3.1]docosa-1(22),8,12,14,18,20-hexaen-10-yl] carbamate;hydrochloride
Synonyms Click here for help
17-AAG (hydrochloride) | 17-Allylamino-17-demethoxygeldanamycin (hydrochloride) | IPI-504 | IPI504
Database Links Click here for help
Specialist databases
Reactome Drug Reactome logo R-ALL-1217514
Reactome Reaction Reactome logo R-HSA-1218824
Other databases
GtoPdb PubChem SID 354702298
PubChem CID 11685945
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