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A 19-membered macrocyle that is geldanamycin in which the methoxy substituent attached to the benzoquinone moiety has been replaced by an allylamino group.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.
Supplier Information ZINC000535385354
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Wikipedia License
Hydralazine, sold under the brand name Apresoline among others, is a medication used to treat high blood pressure and heart failure. This includes high blood pressure in pregnancy and very high blood pressure resulting in symptoms. It has been found to be particularly useful in heart failure, together with isosorbide dinitrate, for treatment of people of African descent. It is given by mouth or by injection into a vein. Effects usually begin around 15 minutes and last up to six hours. Common side effects include headache and fast heart rate. It is not recommended in people with coronary artery disease or in those with rheumatic heart disease that affects the mitral valve. In those with kidney disease a low dose is recommended. Hydralazine is in the vasodilator family of medications, so it is believed to work by causing the dilation of blood vessels. Hydralazine was discovered while scientists at Ciba were looking for a treatment for malaria. It was patented in 1949. It is on the World Health Organization's List of Essential Medicines. In 2022, it was the 121st most commonly prescribed medication in the United States, with more than 5 million prescriptions.
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Formula C31H43N3O8
Net Charge 0
Average Mass 585.690
Monoisotopic Mass 585.30502
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
View more database links
Registry Numbers Types Sources
7402240 Reaxys Registry Number Reaxys
75747-14-7 CAS Registry Number ChemIDplus
Citations
Last Modified
02 June 2016