CHEBI:71975 - retaspimycin

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ChEBI Name retaspimycin
ChEBI ID CHEBI:71975
Definition An 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.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C31H45N3O8
Net Charge 0
Average Mass 587.705
Monoisotopic Mass 587.32067
InChI InChI=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
InChIKey OAKGNIRUXAZDQF-TXHRRWQRSA-N
SMILES C=1C(=C(C2=C(C1NC(=O)C(C)=CC=C[C@@H]([C@@H](OC(N)=O)C(C)=C[C@@H]([C@H]([C@H](C[C@@H](C2)C)OC)O)C)OC)O)NCC=C)O
Roles Classification
Chemical Role(s): Bronsted base
A molecular entity capable of accepting a hydron from a donor (Bronsted acid).
(via organic amino compound )
Biological Role(s): Hsp90 inhibitor
An EC 3.6.4.10 (non-chaperonin molecular chaperone ATPase) inhibitor that blocks the action of heat shock protein 90.
Application(s): antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 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 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
retaspimycin KEGG DRUG
Manual Xrefs Databases
D09375 KEGG DRUG
US2006205705 Patent
US2008255080 Patent
WO2005063714 Patent
WO2005095347 Patent
WO2007002093 Patent
WO2010135426 Patent
View more database links
Registry Numbers Types Sources
11329862 Reaxys Registry Number Reaxys
857402-23-4 CAS Registry Number ChemIDplus
857402-23-4 CAS Registry Number KEGG DRUG
Last Modified
10 May 2016