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

• ChemBase ID: 105920
• Molecular Formular: C12H17NO3
• Molecular Mass: 223.26828
• Monoisotopic Mass: 223.12084341
• SMILES: C/C=C/C/C=C/CCC(=O)C1OC1C(=O)N
• Canonical SMILES: C/C=C/C/C=C/CCC(=O)C1OC1C(=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)
• InChIKey: GVEZIHKRYBHEFX-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-(nona-4,7-dienoyl)oxirane-2-carboxamide
• IUPAC Traditional name: 3-(nona-4,7-dienoyl)oxirane-2-carboxamide
• Synonyms: (2R,3S,E,E)-2,3-Epoxy-4-oxo-7,10-dodecadienamide; Cerulenin; 2,3-Epoxy-4-oxo-7,10-dodecadienamide; CERULENIN

Database IDs

• CAS Number: 17397-89-6
• EC Number: 241-424-8
• MDL Number: MFCD00077686
• Beilstein Number: 4140423
• PubChem SID: 24892323; 162092849
• PubChem CID: 5352018

CALCULATED PROPERTIES

• 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

PROPERTIES

Physical Property

• Solubility: acetone: soluble20 mg/mL, clear, colorless to yellow
• Melting Point: 93°C

Safety Information

• Storage Condition: -20°C
• RTECS: JR1670000
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: -20°C

Pharmacology Properties

• Gene Information: human ... FASN(2194)

Product Information

• Purity: >95%; ≥95% (TLC); ≥98% (HPLC)
• Impurities: ≤1% water
• Biological Source: from Cephalosporium caerulens
• Empirical Formula (Hill Notation): C12H17NO3

DETAILS

MP Biomedicals - 02195098

From Cephalosporum caerulens
Purity: >95%
Antibiotic which inhibits sterol and fatty acid biosynthesis.

Sigma Aldrich - C2389

Biochem/physiol Actions
Cerulenin, an antibiotic and antifungal, is an inhibitor of fatty acid biosynthesis; in vitro inhibition of HIV-1 proteinase.1,2

Sigma Aldrich - 22450

Biochem/physiol Actions
Cerulenin, an antibiotic and antifungal, is an inhibitor of fatty acid biosynthesis; in vitro inhibition of HIV-1 proteinase.1,2

REFERENCES

• Ohno, T., et al., Biochem. Biophys. Res. Commun. , 57 : 1999, (1974).