CHEBI:5292 - geldanamycin

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ChEBI Name geldanamycin
Definition An ansamycin consisting of a 19-membered macrocyle incorporating a benzoquinone ring and a lactam functionality. It shows antimicrobial activity against many Gram-positive and some Gram-negative bacteria.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:42670
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Formula C29H40N2O9
Net Charge 0
Average Mass 560.63590
Monoisotopic Mass 560.27338
InChI InChI=1S/C29H40N2O9/c1-15-11-19-25(34)20(14-21(32)27(19)39-7)31-28(35)16(2)9-8-10-22(37-5)26(40-29(30)36)18(4)13-17(3)24(33)23(12-15)38-6/h8-10,13-15,17,22-24,26,33H,11-12H2,1-7H3,(H2,30,36)(H,31,35)/b10-8-,16-9+,18-13+/t15-,17+,22+,23+,24-,26+/m1/s1
SMILES CO[C@H]1C[C@H](C)CC2=C(OC)C(=O)C=C(NC(=O)\C(C)=C\C=C/[C@H](OC)[C@@H](OC(N)=O)\C(C)=C\[C@H](C)[C@H]1O)C2=O
Roles Classification
Biological Role(s): antiviral agent
A substance that destroys or inhibits replication of viruses.
antimicrobial agent
A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.
cysteine protease inhibitor
Any protease inhibitor that restricts the action of a cysteine protease.
Hsp90 inhibitor
An EC (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.
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ChEBI Ontology
Outgoing geldanamycin (CHEBI:5292) has role antimicrobial agent (CHEBI:33281)
geldanamycin (CHEBI:5292) has role antineoplastic agent (CHEBI:35610)
geldanamycin (CHEBI:5292) has role antiviral agent (CHEBI:22587)
geldanamycin (CHEBI:5292) has role cysteine protease inhibitor (CHEBI:64152)
geldanamycin (CHEBI:5292) has role Hsp90 inhibitor (CHEBI:63962)
geldanamycin (CHEBI:5292) is a 1,4-benzoquinones (CHEBI:132124)
geldanamycin (CHEBI:5292) is a ansamycin (CHEBI:22565)
geldanamycin (CHEBI:5292) is a carbamate ester (CHEBI:23003)
geldanamycin (CHEBI:5292) is a organic heterobicyclic compound (CHEBI:27171)
Incoming alvespimycin (CHEBI:65324) has functional parent geldanamycin (CHEBI:5292)
retaspimycin (CHEBI:71975) has functional parent geldanamycin (CHEBI:5292)
tanespimycin (CHEBI:64153) has functional parent geldanamycin (CHEBI:5292)
(4E,6Z,8S,9S,10E,12S,13R,14S,16R)-13-hydroxy-8,14,19-trimethoxy-4,10,12,16-tetramethyl-3,20,22-trioxo-2-azabicyclo[16.3.1]docosa-1(21),4,6,10,18-pentaen-9-yl carbamate
Synonyms Sources
Geldanamycin KEGG COMPOUND
Manual Xrefs Databases
C00018795 KNApSAcK
Geldanamycin Wikipedia
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Registry Numbers Types Sources
14205884 Reaxys Registry Number Reaxys
30562-34-6 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
21983172 PubMed citation Europe PMC
21985437 PubMed citation Europe PMC
22050565 PubMed citation Europe PMC
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Last Modified
02 June 2016