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CHEBI:71975 - retaspimycin

ChEBI IDCHEBI:71975
ChEBI Nameretaspimycin
Stars
DefinitionAn ansamycin that is tanespimycin in which the benzoquinone moiety has been reduced to the corresponding hydroquinone. A semi-synthetic analogue of geldanamycin, it is used (generally as the hydrochloride salt) in cancer treatment.
Last Modified10 May 2016
SubmitterSteve
DownloadsMolfile
FormulaC31H45N3O8
Net Charge0
Average Mass587.714
Monoisotopic Mass587.32067
SMILESC=CCNc1c(O)cc2c(O)c1C[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)N2
InChIInChI=1S/C31H45N3O8/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/h8-11,15-17,19,24-25,27,29,33,35-37H,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
InChIKeyOAKGNIRUXAZDQF-TXHRRWQRSA-N
Roles Classification
Chemical Role:
Bronsted base  A molecular entity capable of accepting a hydron from a donor (Brønsted acid).
Biological Role:
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)
retaspimycin (CHEBI:71975) has functional parent geldanamycin (CHEBI:5292)
retaspimycin (CHEBI:71975) has role antineoplastic agent (CHEBI:35610)
retaspimycin (CHEBI:71975) has role Hsp90 inhibitor (CHEBI:63962)
retaspimycin (CHEBI:71975) is a ansamycin (CHEBI:22565)
retaspimycin (CHEBI:71975) is a carbamate ester (CHEBI:23003)
retaspimycin (CHEBI:71975) is a hydroquinones (CHEBI:24646)
retaspimycin (CHEBI:71975) is a organic heterobicyclic compound (CHEBI:27171)
retaspimycin (CHEBI:71975) is a secondary amino compound (CHEBI:50995)
retaspimycin (CHEBI:71975) is a semisynthetic derivative (CHEBI:72588)
retaspimycin (CHEBI:71975) is conjugate base of retaspimycin(1+) (CHEBI:71974)
Incoming Relation(s)
retaspimycin(1+) (CHEBI:71974) is conjugate acid of retaspimycin (CHEBI:71975)
IUPAC Name 
(4E,6Z,8S,9S,10E,12S,13R,14S,16R)-19-(allylamino)-13,20,22-trihydroxy-8,14-dimethoxy-4,10,12,16-tetramethyl-3-oxo-2-azabicyclo[16.3.1]docosa-1(22),4,6,10,18,20-hexaen-9-yl carbamate
INN  Source
retaspimycinKEGG DRUG
Manual XrefsDatabases
D09375KEGG DRUG
WO2007002093Patent
WO2010135426Patent
WO2005063714Patent
US2008255080Patent
US2006205705Patent
WO2005095347Patent
Registry NumbersSources
Reaxys:11329862Reaxys
CAS:857402-23-4KEGG DRUG
CAS:857402-23-4ChemIDplus