tanespimycin   Click here for help

GtoPdb Ligand ID: 7751

Synonyms: 17-AAG | 17-allylamino-17-demethoxygeldanamycin | 17-N-allylamino-17-demethoxygeldanamycin | 17AAG
Immunopharmacology Ligand
Comment: 17-AAG inhibits the activity of hsp90. The compound is a derivative of the antibiotic geldanamycin.
As with other natural products, there is some ambiguity in the absolute stereochemistry annotated by different online resources. PubChem records an alternative isomer with a Z bond at position 12 which has CID 6505803.
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 11
Hydrogen bond donors 4
Rotatable bonds 7
Topological polar surface area 166.28
Molecular weight 585.31
XLogP 1.8
No. Lipinski's rules broken 1
SMILES / InChI / InChIKey
Click here for help
Canonical SMILES C=CCNC1=C2CC(C)CC(OC)C(O)C(C)C=C(C)C(C(C=CC=C(C(=O)NC(=CC1=O)C2=O)C)OC)OC(=O)N
Isomeric SMILES C=CCNC1=C2C[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)NC(=CC1=O)C2=O)\C)OC)OC(=O)N
InChI InChI=1S/C31H43N3O8/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/h8-11,15-17,19,24-25,27,29,33,36H,1,12-14H2,2-7H3,(H2,32,39)(H,34,38)/b11-9+,18-10+,20-15+/t17-,19+,24+,25+,27-,29+/m1/s1
InChI Key AYUNIORJHRXIBJ-HTLBVUBBSA-N
Classification Click here for help
Compound class Natural product or derivative
IUPAC Name Click here for help
[(3R,5S,6R,7S,8E,10S,11S,12E,14E)-6-hydroxy-5,11-dimethoxy-3,7,9,15-tetramethyl-16,20,22-trioxo-21-(prop-2-enylamino)-17-azabicyclo[16.3.1]docosa-1(21),8,12,14,18-pentaen-10-yl] carbamate
International Nonproprietary Names Click here for help
INN number INN
8815 tanespimycin
Synonyms Click here for help
17-AAG | 17-allylamino-17-demethoxygeldanamycin | 17-N-allylamino-17-demethoxygeldanamycin | 17AAG
Database Links Click here for help
Specialist databases
Reactome Drug Reactome logo R-ALL-1217506
Reactome Reaction Reactome logo R-HSA-1218824
Other databases
CAS Registry No. 75747-14-7
ChEBI CHEBI:64153
ChEMBL Ligand CHEMBL126955
GtoPdb PubChem SID 223366084
PubChem CID 6440175
Search Google for chemical match using the InChIKey AYUNIORJHRXIBJ-HTLBVUBBSA-N
Search Google for chemicals with the same backbone AYUNIORJHRXIBJ
Search PubMed clinical trials tanespimycin
Search PubMed titles tanespimycin
Search PubMed titles/abstracts tanespimycin
Search UniChem for chemical match using the InChIKey AYUNIORJHRXIBJ-HTLBVUBBSA-N
Search UniChem for chemicals with the same backbone AYUNIORJHRXIBJ
Wikipedia Tanespimycin

Product suppliers

View disclaimer

Tocris
17-AAG
Cat. No. 1515