This HTML5 document contains 58 embedded RDF statements represented using HTML+Microdata notation.

The embedded RDF content will be recognized by any processor of HTML5 Microdata.

Namespace Prefixes

PrefixIRI
n2http://linked.opendata.cz/resource/drugbank/drug/
dctermshttp://purl.org/dc/terms/
n15http://linked.opendata.cz/resource/drugbank/drug/DB01034/identifier/chemspider/
n18http://bio2rdf.org/drugbank:
n14http://linked.opendata.cz/resource/drugbank/drug/DB01034/identifier/chebi/
admshttp://www.w3.org/ns/adms#
n6http://linked.opendata.cz/resource/drugbank/drug/DB01034/identifier/wikipedia/
n7http://linked.opendata.cz/resource/drugbank/drug/DB01034/identifier/pharmgkb/
n17http://wifo5-03.informatik.uni-mannheim.de/drugbank/resource/drugs/
n10http://linked.opendata.cz/resource/drugbank/drug/DB01034/identifier/pdb/
n13http://linked.opendata.cz/resource/drugbank/drug/DB01034/identifier/kegg-compound/
rdfhttp://www.w3.org/1999/02/22-rdf-syntax-ns#
owlhttp://www.w3.org/2002/07/owl#
n3http://linked.opendata.cz/ontology/drugbank/
n11http://linked.opendata.cz/resource/drugbank/drug/DB01034/identifier/pubchem-compound/
n4http://linked.opendata.cz/resource/drugbank/property/
n8http://linked.opendata.cz/resource/drugbank/drug/DB01034/identifier/pubchem-substance/
xsdhhttp://www.w3.org/2001/XMLSchema#
n12http://linked.opendata.cz/resource/drugbank/drug/DB01034/identifier/drugbank/

Statements

Subject Item
n2:DB01034
rdf:type
n3:Drug
n3:description
Cerulenin is an antifungal antibiotic that inhibits sterol and fatty acid biosynthesis. In fatty acid synthesis, reported to bind in equimolar ratio to b-keto-acyl-ACP synthase. In sterol synthesis, inhibits HMG-CoA synthetase activity. It is also shown to inhibit feeding and induce dramatic weight loss in mice. It is found naturally in the Cephalosporium caerulensfungus. [Wikipedia]
n3:generalReferences
# Huang P, Zhu S, Lu S, Dai Z, Jin Y: [An experimental study on cerulenin induced apoptosis of human colonic cancer cells] Zhonghua Bing Li Xue Za Zhi. 2000 Apr;29(2):115-8. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/11866903 # Straub SG, Yajima H, Komatsu M, Aizawa T, Sharp GW: The effects of cerulenin, an inhibitor of protein acylation, on the two phases of glucose-stimulated insulin secretion. Diabetes. 2002 Feb;51 Suppl 1:S91-5. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/11815464
n3:group
approved
n3:indication
For use as a biochemical tool, Cerulenin is shown to cause dramatic weight loss in animals
owl:sameAs
n17:DB01034 n18:DB01034
dcterms:title
Cerulenin
adms:identifier
n6:Cerulenin n7:PA164764551 n8:46508217 n10:CER n11:5282054 n12:DB01034 n13:C12058 n14:171741 n15:26530
n3:mechanismOfAction
Irreversibly binds to fatty acid synthase, specifically b-ketoacyl-acyl carrier protein synthase (FabH, FabB and FabF condensation enzymes). A number of tumor cells and cell lines have been observed to have highly upregulated expression and activity of fatty acid synthase (FAS). Inhibition of FAS by cerulenin leads to cytotoxicity and apoptosis in human cancer cell lines, an effect believed to be mediated by the accumulation of malonyl-coenzyme A in cells with an upregulated FAS pathway.
n3:synonym
(2R,3S)-3-((4e,7e)-Nona-4,7-dienoyl)oxirane-2-carboxamide (2R,3S)-3-((4e,7e)-Nona-4,7-dienoyl)-oxirane-2-carboxylic acid amide Cerulenin
n3:toxicity
Oral, mouse LD<sub>50</sub>: 547 mg/kg. Symptoms of overexposure include moderate to severe erythema (redness) and moderate edema (raised skin), nausea, vomiting, and headache.
n3:synthesisReference
Garfield P. Royer, Craig A. Townsend, "Cerulenin compounds for fatty acid synthesis inhibition." U.S. Patent US5539132, issued July, 1975.
n3:IUPAC-Name
n4:271B56ED-363D-11E5-9242-09173F13E4C5
n3:InChI
n4:271B56F3-363D-11E5-9242-09173F13E4C5
n3:Molecular-Formula
n4:271B56F2-363D-11E5-9242-09173F13E4C5
n3:Molecular-Weight
n4:271B56EF-363D-11E5-9242-09173F13E4C5
n3:Monoisotopic-Weight
n4:271B56F0-363D-11E5-9242-09173F13E4C5
n3:SMILES
n4:271B56F1-363D-11E5-9242-09173F13E4C5
n3:Water-Solubility
n4:271B56EB-363D-11E5-9242-09173F13E4C5 n4:271B5703-363D-11E5-9242-09173F13E4C5
n3:logP
n4:271B56E9-363D-11E5-9242-09173F13E4C5 n4:271B56EC-363D-11E5-9242-09173F13E4C5 n4:271B5705-363D-11E5-9242-09173F13E4C5
n3:logS
n4:271B56EA-363D-11E5-9242-09173F13E4C5
n3:H-Bond-Acceptor-Count
n4:271B56F9-363D-11E5-9242-09173F13E4C5
n3:H-Bond-Donor-Count
n4:271B56FA-363D-11E5-9242-09173F13E4C5
n3:InChIKey
n4:271B56F4-363D-11E5-9242-09173F13E4C5
n3:Polar-Surface-Area--PSA-
n4:271B56F5-363D-11E5-9242-09173F13E4C5
n3:Polarizability
n4:271B56F7-363D-11E5-9242-09173F13E4C5
n3:Refractivity
n4:271B56F6-363D-11E5-9242-09173F13E4C5
n3:Rotatable-Bond-Count
n4:271B56F8-363D-11E5-9242-09173F13E4C5
n3:affectedOrganism
Mycobacterium tuberculosis Humans and other mammals Bacteria Fungi
n3:casRegistryNumber
17397-89-6
n3:category
n3:Bioavailability
n4:271B56FF-363D-11E5-9242-09173F13E4C5
n3:Ghose-Filter
n4:271B5701-363D-11E5-9242-09173F13E4C5
n3:MDDR-Like-Rule
n4:271B5702-363D-11E5-9242-09173F13E4C5
n3:Melting-Point
n4:271B5704-363D-11E5-9242-09173F13E4C5
n3:Number-of-Rings
n4:271B56FE-363D-11E5-9242-09173F13E4C5
n3:Physiological-Charge
n4:271B56FD-363D-11E5-9242-09173F13E4C5
n3:Rule-of-Five
n4:271B5700-363D-11E5-9242-09173F13E4C5
n3:Traditional-IUPAC-Name
n4:271B56EE-363D-11E5-9242-09173F13E4C5
n3:pKa--strongest-acidic-
n4:271B56FB-363D-11E5-9242-09173F13E4C5
n3:pKa--strongest-basic-
n4:271B56FC-363D-11E5-9242-09173F13E4C5