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tanespimycin   Click here for help

GtoPdb Ligand ID: 7751

Synonyms: 17-AAG | 17-allylamino-17-demethoxygeldanamycin | 17-N-allylamino-17-demethoxygeldanamycin | 17AAG | compound 4 [PMID:15978816]
Immunopharmacology Ligand
Compound class: Synthetic organic
Comment: 17-AAG inhibits the activity of hsp90. The compound is a derivative of the antibacterial 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. 17-AAG acts as a femtomolar inhibitor of Met tyrosine kinase receptor-dependent urokinase-plasminogen activation [5].
2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Click here for structure editor
Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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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

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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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

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
Classification Click here for help
Compound class Synthetic organic
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 | compound 4 [PMID:15978816]
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
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UniChem Compound Search for chemical match using the InChIKey AYUNIORJHRXIBJ-HTLBVUBBSA-N
UniChem Connectivity Search for chemical match using the InChIKey AYUNIORJHRXIBJ-HTLBVUBBSA-N
Wikipedia Tanespimycin