(E)-1-nitroso-2-[(2E,4E,7E)-undeca-2,4,7-trien-1-ylidene]hydrazine

• ChemBase ID: 106006
• Molecular Formular: C11H17N3O
• Molecular Mass: 207.27218
• Monoisotopic Mass: 207.13716218
• SMILES: CCC/C=C/C/C=C/C=C/C=N/NN=O
• Canonical SMILES: CCC/C=C/C/C=C/C=C/C=N/NN=O
• InChI: InChI=1S/C11H17N3O/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15/h4-5,7-11H,2-3,6H2,1H3,(H,13,15)
• InChIKey: NKTGCVUIESDXPU-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (E)-1-nitroso-2-[(2E,4E,7E)-undeca-2,4,7-trien-1-ylidene]hydrazine; 1-nitroso-2-(undeca-2,4,7-trien-1-ylidene)hydrazine
• IUPAC Traditional name: triacsin C; 1-nitroso-2-(undeca-2,4,7-trien-1-ylidene)hydrazine
• Synonyms: 2,4,7-Undecatrienal nitrosohydrazone; WS1228A; Triacsin C from Streptomyces sp.; TRIACSIN C

Database IDs

• CAS Number: 76896-80-5
• MDL Number: MFCD00798237
• PubChem SID: 162093132; 24900214
• PubChem CID: 9576787
• Chemspider ID: 7851228
• Wikipedia Title: Triacsin_C

CALCULATED PROPERTIES

• Acid pKa: 7.887274
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 3.2063167
• LogD (pH = 7.4): 3.631971
• Log P: 3.1938655
• Molar Refractivity: 67.1939 cm^3
• Polarizability: 23.460604 Å^3
• Polar Surface Area: 53.82 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

• Storage Condition: -20°C
• German water hazard class: 3
• Storage Temperature: -20°C

Product Information

• Purity: ~90%
• Grade: ACS
• Shipped in: wet ice

DETAILS

MP Biomedicals - 02195851

Purity: ~90%
Selectively inhibits arachidonoyl-CoA synthetase in intact cells and the non-specific acyl-CoA synthetase in cell sonicates.

Sigma Aldrich - T4540

Biochem/physiol Actions
Triacsin C is a potent inhibitor of long-chain fatty acyl CoA synthetase. It blocks β-cell apoptosis, induced by fatty acids (lipoapoptosis) in a rat model of obesity. In addition, it blocks the de novo synthesis of triglycerides, diglycerides, and cholesterol esters, thus interfering with lipid metabolism.
General description
Triacsin C belongs to a family of fungal metabolites all having an 11-carbon alkenyl chain with a common N-hydroxytriazene moiety at the terminus.