(2R,3S)-3-(nona-4,7-dienoyl)oxirane-2-carboxamide

• ChemBase编号: 906
• 分子式: C12H17NO3
• 平均质量: 223.26828
• 单一同位素质量: 223.12084341
• SMILES: O1[C@@H]([C@@H]1C(=O)N)C(=O)CCC=CCC=CC
• Canonical SMILES: CC=CCC=CCCC(=O)[C@H]1O[C@H]1C(=O)N
• 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)/t10-,11-/m1/s1
• InChIKey: GVEZIHKRYBHEFX-GHMZBOCLSA-N

名称和登记号

名称

• IUPAC标准名: (2R,3S)-3-(nona-4,7-dienoyl)oxirane-2-carboxamide
• IUPAC传统名: @cerulenin; cerulenin
• 商标名: Helicocerin
• 别名: Cerulenin

登记号

• CAS号: 17397-89-6
• PubChem SID: 160964369; 46508217
• PubChem CID: 5282054; 28517
• CHEBI ID: 171741
• CHEMBL: 45627
• Chemspider ID: 4445281
• DrugBank ID: DB01034
• KEGG ID: C12058
• 维基百科标题: Cerulenin

理论计算性质

JChem

• Acid pKa: 14.156408
• 质子受体: 3
• 质子供体: 1
• LogD (pH = 5.5): 1.4996911
• LogD (pH = 7.4): 1.499691
• Log P: 1.4996911
• 摩尔折射率: 62.5427 cm^3
• 极化性: 23.606619 Å^3
• 极化表面积: 72.69 Å^2
• 可自由旋转的化学键: 7
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: 1.38
• LOG S: -2.14
• 溶解度: 1.60e+00 g/l

分子性质

理化性质

• 溶解度: Slightly soluble
• 沸点: 456.14°C
• 密度: 1.135 g/mL
• 疏水性(logP): 1.2

详细说明

DrugBank - DB01034

• Drug Groups: approved
• 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]
• Indication: For use as a biochemical tool, Cerulenin is shown to cause dramatic weight loss in animals
• Pharmacology: 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.
• Toxicity: Oral, mouse LD₅₀: 547 mg/kg. Symptoms of overexposure include moderate to severe erythema (redness) and moderate edema (raised skin), nausea, vomiting, and headache.
• Affected Organisms: Humans and other mammals; Fungi; Bacteria
• References: 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] ; 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]
• External Links: Wikipedia

参考文献

• 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
• 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