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

CAS: 17397-89-6 Cat. No.: C102399 Molecular Weight: 223.27 Beilstein Registry Number: 4140423 EC Number: 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

Overview

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

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

Specifications & Purity

Moligand™, ≥98%

Biochemical and Physiological Mechanisms

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

Storage

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

Shipped In

Ice chest + Ice pads

This product requires cold chain shipping. Ground and other economy services are not available.

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.

Purity

≥98%

Names and Identifiers

• Pubchem Sid: 504763395
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/504763395
• Canonical Smiles: 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
• Isomeric SMILES: C/C=C/C/C=C/CCC(=O)[C@@H]1[C@@H](O1)C(=O)N
• WGK Germany: 3
• RTECS: JR1670000
• Molecular Weight: 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
    • Class Epoxides
      • Subclass Oxirane carboxylic acids and derivatives

• Kingdom: Organic compounds
• Superclass: Organoheterocyclic compounds
• Class: 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

Associated Targets(Human)

F2 Tclin Thrombin (11687 Activities)

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ESR1 Tclin Estrogen receptor alpha (17718 Activities)

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PGR Tclin Progesterone receptor (8562 Activities)

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CHRM2 Tclin Muscarinic acetylcholine receptor M2 (10671 Activities)

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HTR1A Tclin Serotonin 1a (5-HT1a) receptor (14969 Activities)

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ADRA2A Tclin Alpha-2a adrenergic receptor (9450 Activities)

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AR Tclin Androgen Receptor (11781 Activities)

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CHRM1 Tclin Muscarinic acetylcholine receptor M1 (12690 Activities)

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VDR Tclin Vitamin D receptor (26531 Activities)

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GABRA1 Tclin GABA receptor alpha-1 subunit (399 Activities)

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MAOA Tclin Monoamine oxidase A (11911 Activities)

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DRD1 Tclin Dopamine D1 receptor (9720 Activities)

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ACHE Tclin Acetylcholinesterase (18204 Activities)

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PTGS1 Tclin Cyclooxygenase-1 (9233 Activities)

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SLC6A2 Tclin Norepinephrine transporter (10102 Activities)

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ADORA1 Tclin Adenosine A1 receptor (17603 Activities)

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SLC6A4 Tclin Serotonin transporter (12625 Activities)

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ADRA1A Tclin Alpha-1a adrenergic receptor (8359 Activities)

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OPRM1 Tclin Mu opioid receptor (19785 Activities)

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DRD3 Tclin Dopamine D3 receptor (14368 Activities)

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SLC6A3 Tclin Dopamine transporter (10535 Activities)

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KCNH2 Tclin HERG (29587 Activities)

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PDE3A Tclin Phosphodiesterase 3A (3309 Activities)

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HTR2B Tclin Serotonin 2b (5-HT2b) receptor (10323 Activities)

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TBXA2R Tclin Thromboxane A2 receptor (5717 Activities)

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THRB Tclin Thyroid hormone receptor beta-1 (7926 Activities)

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PDE4A Tclin Phosphodiesterase 4A (1943 Activities)

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ADORA3 Tchem Adenosine A3 receptor (15931 Activities)

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HRH3 Tclin Histamine H3 receptor (10389 Activities)

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GBA1 Tclin Beta-glucocerebrosidase (14647 Activities)

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KDR Tclin Vascular endothelial growth factor receptor 2 (20924 Activities)

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ALDH1A1 Tchem Aldehyde dehydrogenase 1A1 (77053 Activities)

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FASN Tchem Fatty acid synthase (3390 Activities)

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T-24 (2342 Activities)

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F13A1 Tchem Coagulation factor XIII (223 Activities)

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EHMT2 Tchem Histone-lysine N-methyltransferase, H3 lysine-9 specific 3 (93046 Activities)

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SMN1 Tchem Survival motor neuron protein (34246 Activities)

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Associated Targets(non-human)

pol Human immunodeficiency virus type 1 protease (9113 Activities)

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Hdac6 Histone deacetylase 6 (222 Activities)

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protease Human rhinovirus A protease (1343 Activities)

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Staphylococcus aureus (210822 Activities)

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Bacillus subtilis (32866 Activities)

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Mycobacterium tuberculosis (203094 Activities)

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Saccharomyces cerevisiae (19171 Activities)

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Plasmodium falciparum (966862 Activities)

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Cryptococcus neoformans (21258 Activities)

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Candida albicans (78123 Activities)

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Mus musculus (284745 Activities)

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Moloney murine leukemia virus (54 Activities)

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Rotavirus (147 Activities)

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NIH3T3 (5395 Activities)

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rep Replicase polyprotein 1ab (378 Activities)

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BCHE Cholinesterase (8742 Activities)

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Candida dubliniensis (570 Activities)

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Mapt Microtubule-associated protein tau (6 Activities)

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ABC1 ATP binding cassette transporter Abc1p (50 Activities)

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SARS-CoV-2 (38078 Activities)

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Mechanisms of Action

Chemical and Physical Properties

• Solubility: 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
• Sensitivity: Light sensitive；Moisture sensitive
• Molecular Weight: 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

References

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]