CHEBI:64153 - tanespimycin

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ChEBI Name tanespimycin
ChEBI ID CHEBI:64153
Definition A 19-membered macrocyle that is geldanamycin in which the methoxy substituent attached to the benzoquinone moiety has been replaced by an allylamino group.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.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C31H43N3O8
Net Charge 0
Average Mass 585.690
Monoisotopic Mass 585.305
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
InChIKey AYUNIORJHRXIBJ-TXHRRWQRSA-N
SMILES C=1C(C(=C2C(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.
apoptosis inducer
Any substance that induces the process of apoptosis (programmed cell death) in multi-celled organisms.
Application(s): antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 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 Sources
tanespimycin WHO MedNet
tanespimycina WHO MedNet
tanespimycine WHO MedNet
tanespimycinum WHO MedNet
Synonyms Sources
17-(Allylamino)-17-demethoxygeldanamycin ChemIDplus
17-(Allylamino)geldanamycin ChemIDplus
17-AAG ChEBI
17-allylaminogeldanamycin ChEBI
17-demethoxy-17-(2-propenylamino)geldanamycin ChemIDplus
17-Demethoxy-17-allylamino geldanamycin ChemIDplus
17-N-allylamino-17-demethoxygeldanamycin ChEBI
17AAG ChEBI
NSC 330507 ChemIDplus
NSC-330507 ChemIDplus
Manual Xrefs Databases
17-N-Allylamino-17-demethoxygeldanamycin Wikipedia
D06650 KEGG DRUG
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Registry Numbers Types Sources
7402240 Reaxys Registry Number Reaxys
75747-14-7 CAS Registry Number ChemIDplus
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Last Modified
02 June 2016