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CHEBI:64153 - tanespimycin

ChEBI IDCHEBI:64153
ChEBI Nametanespimycin
Stars
DefinitionA 19-membered macrocyle that is geldanamycin in which the methoxy substituent attached to the benzoquinone moiety has been replaced by an allylamino group.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.
Last Modified2 June 2016
SubmitterMarcus Ennis
DownloadsMolfile
FormulaC31H43N3O8
Net Charge0
Average Mass585.698
Monoisotopic Mass585.30502
SMILESC=CCNC1=C2C[C@@H](C)C[C@H](OC)[C@H](O)[C@@H](C)/C=C(\C)[C@H](OC(N)=O)[C@@H](OC)/C=C\C=C(/C)C(=O)NC(=CC1=O)C2=O
InChIInChI=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
InChIKeyAYUNIORJHRXIBJ-TXHRRWQRSA-N
Wikipedia
Roles Classification
Chemical Role:
Bronsted base  A molecular entity capable of accepting a hydron from a donor (Brønsted acid).
Biological Roles:
apoptosis inducer  Any substance that induces the process of apoptosis (programmed cell death) in multi-celled organisms.
Hsp90 inhibitor  An EC 3.6.4.10 (non-chaperonin molecular chaperone ATPase) inhibitor that blocks the action of heat shock protein 90.
Application:
antineoplastic agent  A substance that inhibits or prevents the proliferation of neoplasms.
ChEBI Ontology
Outgoing Relation(s)
tanespimycin (CHEBI:64153) has functional parent geldanamycin (CHEBI:5292)
tanespimycin (CHEBI:64153) has role antineoplastic agent (CHEBI:35610)
tanespimycin (CHEBI:64153) has role apoptosis inducer (CHEBI:68495)
tanespimycin (CHEBI:64153) has role Hsp90 inhibitor (CHEBI:63962)
tanespimycin (CHEBI:64153) is a 1,4-benzoquinones (CHEBI:132124)
tanespimycin (CHEBI:64153) is a ansamycin (CHEBI:22565)
tanespimycin (CHEBI:64153) is a carbamate ester (CHEBI:23003)
tanespimycin (CHEBI:64153) is a organic heterobicyclic compound (CHEBI:27171)
tanespimycin (CHEBI:64153) is a secondary amino compound (CHEBI:50995)
IUPAC Name 
(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-en-1-ylamino)-2-azabicyclo[16.3.1]docosa-1(21),4,6,10,18-pentaen-9-yl carbamate
INNs  Source
tanespimycinaWHO MedNet
tanespimycineWHO MedNet
tanespimycinumWHO MedNet
tanespimycinWHO MedNet
Synonyms  Source
17-Demethoxy-17-allylamino geldanamycinChemIDplus
17-(Allylamino)-17-demethoxygeldanamycinChemIDplus
17-(Allylamino)geldanamycinChemIDplus
17-demethoxy-17-(2-propenylamino)geldanamycinChemIDplus
17-N-allylamino-17-demethoxygeldanamycinChEBI
17-allylaminogeldanamycinChEBI
Manual XrefsDatabases
17-N-Allylamino-17-demethoxygeldanamycinWikipedia
D06650KEGG DRUG
Registry NumbersSources
Reaxys:7402240Reaxys
CAS:75747-14-7ChemIDplus
Citations