Cerulenin - Moligand™, ≥98% , CAS No.17397-89-6

CAS: 17397-89-6 Cat. No.: C102399 Formule: C₁₂H₁₇NO₃ Poids moléculaire: 223.27 Beilstein Registry Number: 4140423 Numéro CE: 241-424-8

GRADE & PURITY Moligand™, ≥98%

Synonyms

HMS3649F20 | NCGC00163492-01 | BSPBio_001276 | Z2311575475 | (2r,3s)-3-(nona-4,7-dienoyl)oxirane-2-carboxamide | CHEBI:94649 | HMS1990P17 | HY-A0210 | SR-05000002362 | 2-Oxiranecarboxamide, 3-[(4E,7E)-1-oxo-4,7-nonadien-1-yl]-, (2R,3S)- | 3-Nona-4,7-dieno

Storage

Protected from light,Store at -20°C,Argon charged

Shipped In

Ice chest + Ice pads

Vue d’ensemble

Cerulenin has broad application in lipid biochemistry as an inhibitor fatty acid and sterol biosynthesis. Cerulenin binds to β-keto-acyl-ACP .synthase blocking the interaction of malonyl CoA. Cerulenin also an inhibits bacterial fatty acid synthesis, acting on the FabH, FabB and FabF condensation enzymes. Cerulenin stimulates fatty acid oxidation and inhibits HMG-CoA synthetase activity.
An inhibitor fatty acid and sterol biosynthesis

Specifications

Synonymes

HMS3649F20 | NCGC00163492-01 | BSPBio_001276 | Z2311575475 | (2r,3s)-3-(nona-4,7-dienoyl)oxirane-2-carboxamide | CHEBI:94649 | HMS1990P17 | HY-A0210 | SR-05000002362 | 2-Oxiranecarboxamide, 3-[(4E,7E)-1-oxo-4,7-nonadien-1-yl]-, (2R,3S)- | 3-Nona-4,7-dieno

Spécifications et pureté

Moligand™, ≥98%

Mécanismes biochimiques et physiologiques

Cerulenin, an antibiotic and antifungal, is an inhibitor of fatty acid biosynthesis; in vitro inhibition of HIV-1 proteinase.Antifungal antibiotic. Fatty Acid Synthase (FAS) and steriod biosynthesis inhibitor. Binds covalently to the active center cystein

Conditions de stockage de stockage

Protected from light,Store at -20°C,Argon charged

Expédié en

Ice chest + Ice pads

Ce produit nécessite l'expédition en chaîne froide. Les services terrestres et autres services économiques ne sont pas disponibles.

Grade

Moligand™

Note

Wherever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20°C. Generally, these will be useable for up to one month. Before use, and prior to opening the vial we recommend that you allow your product to equilibrate to room temperature for at least 1 hour. Need more advice on solubility, usage and handling? Please visit our frequently asked questions (FAQ) page for more details.

Pureté

≥98%

Noms et identifiants

• Pubchem Sid: 504763395
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/504763395
• Sourires canoniques: CC=CCC=CCCC(=O)C1C(O1)C(=O)N
• IUPAC Name: (2R,3S)-3-[(4E,7E)-nona-4,7-dienoyl]oxirane-2-carboxamide
• InChIKey: GVEZIHKRYBHEFX-NQQPLRFYSA-N
• 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
• Isomères SMILES: C/C=C/C/C=C/CCC(=O)[C@@H]1[C@@H](O1)C(=O)N
• WGK Allemagne: 3
• RTECS: JR1670000
• Poids moléculaire: 223.27
• Beilstein: 4140423
• Reaxy-Rn: 1429809
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=1429809&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organoheterocyclic compounds
    • Classe Epoxides
      • Subclass Oxirane carboxylic acids and derivatives

• Kingdom: Organic compounds
• Superclass: Organoheterocyclic compounds
• Classe: Epoxides
• Subclass: Oxirane carboxylic acids and derivatives
• Intermediate Tree Nodes: Not available
• Direct Parent: Oxirane carboxylic acids and derivatives
• Alternative Parents: Monosaccharides Primary carboxylic acid amides Ketones Oxacyclic compounds Dialkyl ethers Organopnictogen compounds Organonitrogen compounds Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aliphatic heteromonocyclic compounds
• Substituents: Oxirane carboxylic acid or derivatives - Monosaccharide - Carboxamide group - Ketone - Primary carboxylic acid amide - Carboxylic acid derivative - Dialkyl ether - Ether - Oxacycle - Carbonyl group - Organonitrogen compound - Organooxygen compound - Hydrocarbon derivative - Organic oxide - Organopnictogen compound - Organic oxygen compound - Organic nitrogen compound - Aliphatic heteromonocyclic compound
• Description: This compound belongs to the class of organic compounds known as oxirane carboxylic acids and derivatives. These are compounds containing an oxirane ring bearing a carboxylic acid group (or a derivative thereof).
• External Descriptors: monocarboxylic acid amide - epoxide

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

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Mécanismes d'action

Propriétés chimiques et physiques

• Solubilité: Cerulenin is soluble in DMSO, Methanol, Ethanol, Dichloromethane, Acetone, Benzene and most common solvents. Concentrations up to 20 mg/ml can be achieved. Slightly soluble in H2O. Concentrations up to 0.2 mg/ml are achievable. Not soluble in Petrol Ether
• Sensibilité: Light sensitive；Moisture sensitive
• Poids moléculaire: 223.270 g/mol
• XLogP3: 0.800
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 7
• Exact Mass: 223.121 Da
• Monoisotopic Mass: 223.121 Da
• Topological Polar Surface Area: 72.700 Ų
• Heavy Atom Count: 16
• Formal Charge: 0
• Complexity: 320.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 2
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 2
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 2
• Covalently-Bonded Unit Count: 1

Références

1. Li Wenwen, Pang Yana, Wang Yan, Mei Fan, Guo Mengmeng, Wei Yiping, Li Xinyue, Qin Wei, Wang Wei, Jia Longfei, Jia Jianping.  (2023)  Aberrant palmitoylation caused by a ZDHHC21 mutation contributes to pathophysiology of Alzheimer’s disease.  BMC Medicine,  21  (1): (1-17).  [PMID:37365538] [10.1186/s12916-023-02930-7]

2. Hui Lu, Wanqian Li, Malcolm Whiteway, Hongkang Wang, Shuo Zhu, Zhe Ji, Yanru Feng, Lan Yan, Ting Fang, Liping Li, Tingjunhong Ni, Xiaolong Zhang, Quanzhen Lv, Zichao Ding, Lijuan Qiu, Dazhi Zhang, Yuanying Jiang.  (2022)  A Small Molecule Inhibitor of Erg251 Makes Fluconazole Fungicidal by Inhibiting the Synthesis of the 14α-Methylsterols.  mBio,  14  (1):   [PMID:36475771] [10.1128/mbio.02639-22]

3. Jun Ni, Fei Tao, Yu Wang, Feng Yao, Ping Xu.  (2016)  A photoautotrophic platform for the sustainable production of valuable plant natural products from CO2.  GREEN CHEMISTRY,  18  (12): (3537-3548).  [PMID:] [10.1039/C6GC00317F]

4. Du Fei, Xu Qing, Li Xin, Hang Yiwen, Zhang Duoduo, Zhang Feng, Ma Wang, Sun Xiaoman, Huang He.  (2025)  Regulating triacylglycerol cycling for high-efficiency production of polyunsaturated fatty acids and derivatives.  Nature Communications,  16  (1): (1-12).  [PMID:40335511] [10.1038/s41467-025-59599-0]