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

• ChemBase ID: 906
• Molecular Formular: C12H17NO3
• Molecular Mass: 223.26828
• Monoisotopic Mass: 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

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3S)-3-(nona-4,7-dienoyl)oxirane-2-carboxamide
• IUPAC Traditional name: @cerulenin; cerulenin
• Brand Name: Helicocerin
• Synonyms: Cerulenin

Database IDs

• CAS Number: 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
• Wikipedia Title: Cerulenin

CALCULATED PROPERTIES

JChem

• Acid pKa: 14.156408
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 1.4996911
• LogD (pH = 7.4): 1.499691
• Log P: 1.4996911
• Molar Refractivity: 62.5427 cm^3
• Polarizability: 23.606619 Å^3
• Polar Surface Area: 72.69 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 1.38
• LOG S: -2.14
• Solubility (Water): 1.60e+00 g/l

PROPERTIES

Physical Property

• Solubility: Slightly soluble
• Boiling Point: 456.14°C
• Density: 1.135 g/mL
• Hydrophobicity(logP): 1.2

DETAILS

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

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