CHEBI:5292 - geldanamycin

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ChEBI Name geldanamycin
ChEBI ID CHEBI:5292
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 560.273
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
InChIKey QTQAWLPCGQOSGP-KSRBKZBZSA-N
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 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 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)
IUPAC Name
(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 PDBeChem
Geldanamycin KEGG COMPOUND
Manual Xrefs Databases
C00018795 KNApSAcK
C11222 KEGG COMPOUND
GDM PDBeChem
Geldanamycin Wikipedia
View more database links
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
22136518 PubMed citation Europe PMC
22138446 PubMed citation Europe PMC
22215907 PubMed citation Europe PMC
22277058 PubMed citation Europe PMC
22361388 PubMed citation Europe PMC
Last Modified
02 June 2016