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CHEBI:5292 - geldanamycin

ChEBI IDCHEBI:5292
ChEBI Namegeldanamycin
Stars
DefinitionAn 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.
Secondary ChEBI IDCHEBI:42670
Last Modified2 June 2016
DownloadsMolfile
FormulaC29H40N2O9
Net Charge0
Average Mass560.644
Monoisotopic Mass560.27338
SMILESCOC1=C2C[C@@H](C)C[C@H](OC)[C@H](O)[C@@H](C)/C=C(\C)[C@H](OC(N)=O)[C@@H](OC)/C=C\C=C(/C)C(=O)NC(=CC1=O)C2=O
InChIInChI=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
InChIKeyQTQAWLPCGQOSGP-KSRBKZBZSA-N
Wikipedia
Roles Classification
Biological Roles:
antimicrobial agent  A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.
Hsp90 inhibitor  An EC 3.6.4.10 (non-chaperonin molecular chaperone ATPase) inhibitor that blocks the action of heat shock protein 90.
antiviral agent  A substance that destroys or inhibits replication of viruses.
cysteine protease inhibitor  Any protease inhibitor that restricts the action of a cysteine protease.
Application:
antineoplastic agent  A substance that inhibits or prevents the proliferation of neoplasms.
ChEBI Ontology
Outgoing Relation(s)
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 Relation(s)
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  Source
GeldanamycinKEGG COMPOUND
GELDANAMYCINPDBeChem
Manual XrefsDatabases
C11222KEGG COMPOUND
GDMPDBeChem
GeldanamycinWikipedia
C00018795KNApSAcK
Registry NumbersSources
Reaxys:14205884Reaxys
CAS:30562-34-6ChemIDplus
Citations