Tanespimycin
[(4E,6Z,8S,9S,10E,12S,13R,14S,16R)-13-hydroxy-8,14-dimethoxy-4,10,12,16-tetramethyl-3,20,22-trioxo-19-(prop-2-enylamino)-2-azabicyclo[16.3.1]docosa-1(21),4,6,10,18-pentaen-9-yl] carbamate
Molecular Identity
Tanespimycin
[(4E,6Z,8S,9S,10E,12S,13R,14S,16R)-13-hydroxy-8,14-dimethoxy-4,10,12,16-tetramethyl-3,20,22-trioxo-19-(prop-2-enylamino)-2-azabicyclo[16.3.1]docosa-1(21),4,6,10,18-pentaen-9-yl] carbamate
PubChem CID: 6505803
Tanespimycin is a 19-membered macrocyle that is geldanamycin in which the methoxy substituent attached to the benzoquinone moiety has been replaced by an allylamino group. It is a potent inhibitor of heat shock protein 90 (Hsp90). A less toxic analogue than geldanamycin, it induces apoptosis and displays antitumour effects. It has a role as an antineoplastic agent, a Hsp90 inhibitor and an apoptosis inducer. It is a member of 1,4-benzoquinones, an ansamycin, a carbamate ester, an organic heterobicyclic compound and a secondary amino compound. It is functionally related to a geldanamycin.
2D Structure
Properties
C31H43N3O8
Molecular Formula
585.70
Molecular Weight
g/mol
585.3050
Exact Mass
Da
2.6
XLogP
Drug-like (Lipinski: < 5)
166
TPSA
May have limited oral absorption
4
H-Bond Donors
9
H-Bond Acceptors
1210
Complexity
SMILES
Canonical SMILES
SMILES: Synonyms(20)
Tanespimycin75747-14-717-AAG17-(Allylamino)-17-demethoxygeldanamycin17AAGNSC-330507KOS-95317-(Allylamino)geldanamycintanespimycinetanespimicinatanespimycinumBMS-72278217-Demethoxy-17-allylamino geldanamycin4GY0AVT3L4NSC 330507
Data from PubChem (NCBI)
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Drug Network
Trials and conditions connected to Tanespimycin
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