Tìm theo
Cerulenin
Các tên gọi khác (3) :
  • (2R,3S)-3-((4e,7e)-Nona-4,7-dienoyl)-oxirane-2-carboxylic acid amide
  • (2R,3S)-3-((4e,7e)-Nona-4,7-dienoyl)oxirane-2-carboxamide
  • Cerulenin
antifungal agents
Thuốc Gốc
Small Molecule
CAS: 17397-89-6
CTHH: C12H17NO3
PTK: 223.2683
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]
Nhận Dạng Quốc Tế & Đặc Tính Hóa Học
Công thức hóa học
C12H17NO3
Phân tử khối
223.2683
Monoisotopic mass
223.120843415
InChI
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
InChI Key
InChIKey=GVEZIHKRYBHEFX-NQQPLRFYSA-N
IUPAC Name
(2R,3S)-3-(nona-4,7-dienoyl)oxirane-2-carboxamide
Traditional IUPAC Name
(2R,3S)-3-(nona-4,7-dienoyl)oxirane-2-carboxamide
SMILES
CC=CCC=CCCC(=O)[C@H]1O[C@H]1C(N)=O
Độ tan chảy
93.5 °C
Độ hòa tan
Slightly soluble
logP
1.2
logS
-2.1
pKa (strongest acidic)
14.16
pKa (Strongest Basic)
-4.3
PSA
72.69 Å2
Refractivity
62.54 m3·mol-1
Polarizability
23.9 Å3
Rotatable Bond Count
7
H Bond Acceptor Count
3
H Bond Donor Count
1
Physiological Charge
0
Number of Rings
1
Bioavailability
1
Rule of Five
true
Ghose Filter
true
Dược Lực Học : Cerulenin is an antifungal antibiotic isolated from Cephalosporium caerulens. It interrupts fungal growth by inhibiting the biosynthesis of sterols and fatty acids (inhibits bacterial fatty acid synthesis). It also inhibits HMG-CoA synthetase activity. Cerulenin produces metabolic effects similar to effects of leptin, but through mechanisms that are independent of, or down-stream from, both leptin and melanocortin receptors.
Cơ Chế Tác Dụng : 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] 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.
Độc Tính : Oral, mouse LD50: 547 mg/kg. Symptoms of overexposure include moderate to severe erythema (redness) and moderate edema (raised skin), nausea, vomiting, and headache.
Chỉ Định : For use as a biochemical tool, Cerulenin is shown to cause dramatic weight loss in animals
Dữ Kiện Thương Mại
Nhà Sản Xuất
  • Công ty :
    Sản phẩm biệt dược : Helicocerin
Tài Liệu Tham Khảo Thêm
drugbank
http://www.drugbank.ca/drugs/DB01034
PubChem Compound
http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=5282054
PubChem Substance
http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=46508217
KEGG Compound
http://www.genome.jp/dbget-bin/www_bget?cpd:C12058
ChemSpider
http://www.chemspider.com/Chemical-Structure.26530.html
PharmGKB
http://www.pharmgkb.org/drug/PA164764551
Wikipedia
http://en.wikipedia.org/wiki/Cerulenin
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