294:
199:
24:
438:
500:, another enzyme normally inhibited by malonyl-CoA. Inhibition involves covalent thioacylation that permanently inactivates the enzymes. These two behaviors may increase the availability of energy in the form of
488:. It was the first natural product antibiotic known to inhibit lipid synthesis. In fatty acid synthesis, it has been reported to bind in equimolar ratio to b-keto-acyl-ACP synthase, one of the seven moieties of
451:
540:
dose of 30 milligrams per kilogram, it has been shown to inhibit feeding and induce dramatic weight loss in mice by a mechanism similar to, but independent or downstream of,
343:
96:
515:
In sterol synthesis, cerulenin inhibits HMG-CoA synthetase activity. It was also reported that cerulenin specifically inhibited fatty acid biosynthesis in
308:
521:
without having an effect on sterol formation. But in general conclusion, cerulenin has inhibitory effects on sterol synthesis.
317:
InChI=1S/C12H17NO3/c1-2-3-4-5-6-7-8-9(14)10-11(16-10)12(13)15/h2-3,5-6,10-11H,4,7-8H2,1H3,(H2,13,15)/b3-2+,6-5+/t10-,11-/m1/s1
327:
InChI=1/C12H17NO3/c1-2-3-4-5-6-7-8-9(14)10-11(16-10)12(13)15/h2-3,5-6,10-11H,4,7-8H2,1H3,(H2,13,15)/b3-2+,6-5+/t10-,11-/m1/s1
763:
458:
628:"The effects of cerulenin, an inhibitor of protein acylation, on the two phases of glucose-stimulated insulin secretion"
505:
251:
925:
892:
272:
517:
485:
759:"Inhibition of fatty acid synthase (FAS) suppresses HER2/neu (erbB-2) oncogene overexpression in cancer cells"
528:
protein levels in breast cancer cells, from 14% at 1.25 to 78% at 10 milligrams per liter, and targeting of
194:
501:
915:
136:
627:
583:
Volpe, J J; Vagelos, P R (1976). "Mechanisms and regulation of biosynthesis of saturated fatty acids".
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36:
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62:
496:. It also has the related activity of stimulating fatty acid oxidation through the activation of
550:
930:
871:
826:
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739:
710:"Mechanism of Action of CM-55, a Synthetic Analogue of the Antilipogenic Antibiotic Cerulenin"
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by related drugs has been suggested as a possible treatment. Antiproliferative and pro-
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Straub SG, Yajima H, Komatsu M, Aizawa T, Sharp GW (February 2002).
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Except where otherwise noted, data are given for materials in their
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107:
95:
85:
666:"Fatty acid metabolism, the central nervous system, and feeding"
497:
206:
664:
Ronnett GV, Kleman AM, Kim EK, Landree LE, Tu Y (August 2006).
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Ohno T, Awaya J, Kesado T, Nomura S, Omura S (October 1974).
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846:"Detection and quantification of phytotoxic metabolites of
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signaling. It is found naturally in the industrial strain
757:
Menendez JA, Vellon L, Mehmi I, et al. (July 2004).
844:
Ghosh MK, Amudha R, Jayachandran S, Sakthivel N (2002).
536:
effects have been shown in colon cells as well. At an
446:
817:
Huang P, Zhu S, Lu S, Dai Z, Jin Y (April 2000). "".
239:
422:456.14 °C (853.05 °F; 729.29 K)
71:
591:(2). American Physiological Society: 339–417.
524:Cerulenin causes a dose-dependent decrease in
8:
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15:
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850:in sheath rot-infected grains of rice"
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320:Key: GVEZIHKRYBHEFX-NQQPLRFYSA-N
135:
115:
7:
554:, the sheath rot pathogen of rice).
330:Key: GVEZIHKRYBHEFX-NQQPLRFYBP
230:
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14:
867:10.1046/j.1472-765X.2002.01111.x
436:
384:
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22:
432:(at 25 °C , 100 kPa).
492:, blocking the interaction of
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372:
1:
764:Proc. Natl. Acad. Sci. U.S.A.
634:. 51 Suppl 1 (90001): S91–5.
597:10.1152/physrev.1976.56.2.339
714:Antimicrob. Agents Chemother
641:10.2337/diabetes.51.2007.S91
351:O=C(CC/C=C/C/C=C/C)1O1C(=O)N
819:Zhonghua Bing Li Xue Za Zhi
947:
426:
359:
339:
304:
55:
49:)-3-oxirane-2-carboxamide
35:
30:
21:
546:Cephalosporium caerulens
518:Saccharomyces cerevisiae
785:10.1073/pnas.0403390101
670:Obesity (Silver Spring)
676:(Suppl 5): 201S–207S.
402:223.2695
854:Lett. Appl. Microbiol
585:Physiological Reviews
683:10.1038/oby.2006.309
504:, perhaps sensed by
486:steroid biosynthesis
37:Preferred IUPAC name
776:2004PNAS..10110715M
726:10.1128/aac.6.4.387
530:fatty acid synthase
490:fatty acid synthase
18:
926:Alkene derivatives
848:Sarocladium oryzae
551:Sarocladium oryzae
459:Infobox references
16:
467:Chemical compound
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273:CompTox Dashboard
97:Interactive image
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893:Cerulenin from
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860:(6): 398–401.
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916:Carboxamides
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825:(2): 115–8.
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662:Reviewed in
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510:hypothalamus
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117:CHEBI:171741
56:Identifiers
46:
42:
911:Antifungals
494:malonyl-CoA
412:1.135 g/mL
360:Properties
195:100.037.643
137:ChEMBL45627
905:Categories
570:References
482:fatty acid
478:antibiotic
475:antifungal
398:Molar mass
261:MF286Y830Q
148:ChemSpider
84:3D model (
73:17397-89-6
63:CAS Number
17:Cerulenin
896:Fermentek
605:0031-9333
534:apoptotic
508:, in the
471:Cerulenin
931:Epoxides
876:12028418
831:11866903
804:15235125
692:17021367
650:11815464
632:Diabetes
558:See also
526:HER2/neu
168:DrugBank
921:Ketones
772:Bibcode
744:4157441
452:what is
450: (
408:Density
241:5282054
228:PubChem
177:DB01034
157:4445281
874:
829:
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795:490000
792:
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735:444657
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542:leptin
473:is an
447:verify
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344:SMILES
216:C12058
128:ChEMBL
31:Names
309:InChI
108:ChEBI
86:JSmol
872:PMID
827:PMID
800:PMID
740:PMID
688:PMID
646:PMID
613:6981
609:PMID
601:ISSN
506:AMPK
498:CPT1
484:and
252:UNII
207:KEGG
862:doi
790:PMC
780:doi
768:101
730:PMC
722:doi
678:doi
636:doi
593:doi
502:ATP
278:EPA
231:CID
907::
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548:(
442:N
391:3
388:O
385:N
379:H
373:C
280:)
276:(
88:)
47:S
43:R
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