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CHEBI:66181 - sch 642305

ChEBI IDCHEBI:66181
ChEBI Namesch 642305
Stars
DefinitionA macrocyclic lactone isolated from the fermentation broth of the fungal culture Penicillium verrucosum and has been shown to exhibit inhibitory activity against bacterial DNA primase enzyme.
Last Modified13 January 2014
DownloadsMolfile
FormulaC14H20O4
Net Charge0
Average Mass252.310
Monoisotopic Mass252.13616
SMILES[H][C@@]12CCCC[C@H](C)OC(=O)C[C@@]1([H])[C@@H](O)C=CC2=O
InChIInChI=1S/C14H20O4/c1-9-4-2-3-5-10-11(8-14(17)18-9)13(16)7-6-12(10)15/h6-7,9-11,13,16H,2-5,8H2,1H3/t9-,10+,11+,13-/m0/s1
InChIKeyWTQWDNIIFGEBSZ-WGBDABJCSA-N
Species of MetaboliteComponentSourceComments
Penicillium verrucosum (ncbitaxon:60171) - PubMed (14695789)
Roles Classification
Biological Roles:
Penicillium metabolite  Any fungal metabolite produced during a metabolic reaction in Penicillium.
EC 2.7.7.6 (RNA polymerase) inhibitor  An EC 2.7.7.* (nucleotidyltransferase) inhibitor that interferes with the action of RNA polymerase (EC 2.7.7.6).
ChEBI Ontology
Outgoing Relation(s)
sch 642305 (CHEBI:66181) has role Penicillium metabolite (CHEBI:76964)
sch 642305 (CHEBI:66181) has role EC 2.7.7.6 (RNA polymerase) inhibitor (CHEBI:37416)
sch 642305 (CHEBI:66181) is a enone (CHEBI:51689)
sch 642305 (CHEBI:66181) is a macrocyclic lactone (CHEBI:63944)
IUPAC Name 
(4S,8aR,12S,12aR)-12-hydroxy-4-methyl-4,5,6,7,8,8a,12,12a-octahydro-2H-3-benzoxecine-2,9(1H)-dione
Synonym  Source
(+)-sch 642305ChEBI
Registry NumbersSources
Reaxys:9780683Reaxys
Citations