Basic information
- CAS
17397-89-6- Standard SMILES
CC=CCC=CCCC(=O)[C@H]1O[C@H]1C(N)=O- InChIKey
GVEZIHKRYBHEFX-GHMZBOCLSA-N- Molecular formula
- C12H17NO3
- Average molar mass
- 223.27 g/mol
- Monoisotopic mass
- 223.1208434
Names & identifiers
- Preferred name
- (2R,3S)-3-(1-oxonona-4,7-dienyl)-2-oxiranecarboxamide
- IUPAC
- (2R,3S)-3-nona-4,7-dienoyloxirane-2-carboxamide
- English name
- CERULENIN
- Molecular formula
- C12H17NO3
- Molecular weight
- 223.27
Names & synonyms
(2R,3S)-3-(1-oxonona-4,7-dienyl)-2-oxiranecarboxamide(2R,3S)-3-nona-4,7-dienoyloxirane-2-carboxamideKBioGR_000616KBioSS_000616SCHEMBL41947873KBio2_000616KBio2_003184KBio2_005752KBio3_001091KBio3_001092Bio2_000478Bio2_000958
Show more names
CrlCERULENINNsc116069Aids000236helicocerinAids-000236CERULENIN USP/EP/BPGlycerol Impurity 10Cerulenin (Synthetic)2,3-epoxy-4-oxo-10-dodecadienamide
PD009586Q27166463
Database identifiers
- CAS
17397-89-6- PubChem CID
- 28517
Properties
Computed structural properties
- XLogP
- 0.8
- Topological polar surface area
- 72.7 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 7
- Heavy atoms
- 16
- Formal charge
- 0
- Complexity
- 320
Experimental & physicochemical properties
LogP1.2
Solubility1.60e+00 g/L
Melting Point93.5 °C
Physical DescriptionSolid
Physicochemical properties
- Melting point
- 93.5 ℃ · 93.5℃
- alpha
- 16 · D16 +63° (c = 2 in methanol)
- Boiling point
- 120 ° · bp 120° (10-8 mm)
- Density
- 1.1223 · 1.1223 (rough estimate)
- refractive index
- 1.53 · 1.5300 (estimate)
- storage temp.
- 20 °C · −20°C
- solubility
- 20 mg/mL, · acetone: 20 mg/mL, clear, colorless to yellow
- pka
- 15.19 · 15.19±0.40(Predicted)
- form
- White to off-white solid
- color
- Off-white
- Merck
- 13 · 13,2014
- BRN
- 4140423 · 4140423
- Stability
- 2 years · Stable for 2 years from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20° for up to 1 month.
- InChI
- 1S/C13H18O3/c1-3-4-5-6-7-8-9-11(15)13-12(16-13)10(2)14/h3-4,6-7,12-13H,5,8-9H2,1-2H3/b4-3+,7-6+/t12-,13+/m0/s1
- InChIKey
- PTNNGEBMCNMENY-JIVMHGEESA-N
- SMILES
- C/C=C/C/C=C/CCC([C@@H]1[C@H](C(N)=O)O1)=O
- FDA UNII
- 286 Y830Q · MF286Y830Q
- UNSPSC Code
- 41106500 · 41106500
- NACRES
- 77 · NA.77
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 302 · H302
- Precautionary statements
- 264 · P264-P270-P301+P312-P501
- PPE
- 95 · dust mask type N95 (US), Eyeshields, Gloves
- Hazard Codes
- Xn
- Risk Statements
- 22 · 22
- Safety Statements
- 24 · 24/25
- WGK Germany
- 3 · 3
- RTECS
- 1670000 · JR1670000
- F
- 10 · 10-21
- HS Code
- 29419090 · 29419090
- Storage Class
- 11 · 11 - Combustible Solids
- Hazard Classifications
- 4 Oral · Acute Tox. 4 Oral
- Toxicity
- 50 in · LD50 in mice (mg/kg): 154 i.v.; 211 i.p.; 547 orally (Matsumae 1964)
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- F
- 10-21
- PPE
- dust mask type N95 (US), Eyeshields, Gloves
- wgk
- 3
- rtecs
- JR1670000
- hs_code
- 29419090
- Toxicity
- LD50 in mice (mg/kg): 154 i.v.; 211 i.p.; 547 orally (Matsumae 1964)
- risk_code
- 22
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xn
- safety_code
- 24/25
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H302
- Hazard Classifications
- Acute Tox. 4 Oral
- Precautionary statements
- P264-P270-P301+P312-P501
Chemistry & industry
Pharmacology
Cellular LocationsCytoplasm
Applications
DescriptionCerulenin is a fungal metabolite originally isolated from C. caerulens that has diverse biological activities. It is active against a variety of bacteria, including B. subtilis, E. coli, B. megaterium, and B. anthracis (MICs = 12.5, 12.5, 50, and 50 μg/ml, respectively) and fungi, including strains of C. albicans, T. rubrum, and A. fumigatus (MICs = 0.8-3.7, 3.1-6.2 and 12.5-50 μg/ml, respectively). Cerulenin is an inhibitor of fatty acid synthase type I (FAS-I) and FAS-II (IC50s = 3 and 20 μM, respectively, for the E. coli enzymes). It inhibits fatty acid synthesis in a panel of human cancer cell lines, including breast, ovarian, and endometrial cancer cells, as well as reduces tumor growth in a OVCAR-3 mouse xenograft model.
UsesCerulenin is an epoxy fatty acid amide isolated from the fungus Cephalosporium caerulens and identified as an antifungal in the 1960s. Over the past 40 years, cerulenin has found 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.
UsesCerulenin is an epoxy fatty acid amide isolated from the fungus Cephalosporium caerulens identified as an antifungal in the 1960s. Over the past 40 years, cerulenin has found 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.
UsesCerulenin is used as an antifungal antibiotic that inhibits sterol and fatty acids biosynthesis. Cerulenin induces apoptosis in tumor cell lines. It can be a useful biochemical tool with applications for the study of metabolism and function of fatty acids in the bacterial cell membrane and in yeast. An extensive review including the properties, uses, mechanism of action and structure has been reported.
General DescriptionAn anti-fungal antibiotic that inhibits fatty acid biosynthesis by binding, in equimolar ratio, to β-keto-acyl-ACP synthase. Also inhibits sterol synthesis by blocking the activity of HMG-CoA synthetase activity. Systemic and intracerebroventricular of this compound reduces feeding and induces weight loss.
Suppliers88 total
北京华美互利生物化工010-56205725 · [email protected]
阿诺西（上海）生物技术有限公司400-1107768 15058188853 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
成都超九八生物科技有限公司13348960310 13348960310 · [email protected]
咸宁深蓝生物医药研发有限公司18171815831 · [email protected]
郑州汇聚化工有限公司13393710386 · [email protected]
上海遐瑞医药科技有限公司+86-021-61551413 · [email protected]
江苏艾康生物医药研发有限公司025-66061636 19370895928 · [email protected]
T&W GROUP021-61551611 13296011611 · [email protected]
湖北科乐精细化工有限公司027-59101668 19945030958 · [email protected]
上海赛可锐生物科技有限公司021-58000709 13120558703 · [email protected]
上海晶抗生物工程有限公司021-54721350 13524668266 · [email protected]
广东元丰化学试剂有限公司0751-2829979 13318593351 · [email protected]
孟成科技（上海）有限公司400-820-6829 · [email protected]
United Life Science020-82099279 18988968278 · [email protected]
Additional notes
DefinitionChEBI: An epoxydodecadienamide isolated from several species, including Acremonium, Acrocylindrum and Helicoceras. It inhibits the biosynthesis of several lipids by interfering with enzyme function.
Related reactions
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Compound notes
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