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.
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2D Structure
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Physico-chemical Properties
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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
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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
References
1. Abramson JS, Chen W, Juszczynski P, Takahashi H, Neuberg D, Kutok JL, Takeyama K, Shipp MA. (2009)
The heat shock protein 90 inhibitor IPI-504 induces apoptosis of AKT-dependent diffuse large B-cell lymphomas.
Br J Haematol, 144 (3): 358-66. [PMID:19036086]
2. Dimopoulos MA, Mitsiades CS, Anderson KC, Richardson PG. (2011)
Tanespimycin as antitumor therapy.
Clin Lymphoma Myeloma Leuk, 11 (1): 17-22. [PMID:21454186]
3. Li Z, Jia L, Wang J, Wu X, Hao H, Xu H, Wu Y, Shi G, Lu C, Shen Y. (2014)
Design, synthesis and biological evaluation of 17-arylmethylamine-17-demethoxygeldanamycin derivatives as potent Hsp90 inhibitors.
Eur J Med Chem, 85: 359-70. [PMID:25105924]
4. Puthiyakunnon S, He X, Boddu S, Huang SH, Cao H. (2017)
C-Met Inhibitors are Potential Novel Therapeutic Agents Against Listeria monocytogenes Infection Through Blocking the Bacteria Entry into Nonphagocytic Cells.
Curr Top Med Chem, 17 (3): 278-289. [PMID:27572078]
5. Shen Y, Xie Q, Norberg M, Sausville E, Vande Woude G, Wenkert D. (2005)
Geldanamycin derivative inhibition of HGF/SF-mediated Met tyrosine kinase receptor-dependent urokinase-plasminogen activation.
Bioorg Med Chem, 13 (16): 4960-71. [PMID:15978816]