3,9,15-tribenzyl-4,10,16-trimethyl-6,12,18-tris(propan-2-yl)-1,7,13-trioxa-4,10,16-triazacyclooctadecane-2,5,8,11,14,17-hexone

• ChemBase ID: 132634
• Molecular Formular: C45H57N3O9
• Molecular Mass: 783.94878
• Monoisotopic Mass: 783.40948042
• SMILES: CC(C)C1C(=O)N(C(C(=O)OC(C(=O)N(C(C(=O)OC(C(=O)N(C(C(=O)O1)Cc1ccccc1)C)C(C)C)Cc1ccccc1)C)C(C)C)Cc1ccccc1)C
• Canonical SMILES: CC(C1OC(=O)C(Cc2ccccc2)N(C)C(=O)C(OC(=O)C(N(C(=O)C(OC(=O)C(N(C1=O)C)Cc1ccccc1)C(C)C)C)Cc1ccccc1)C(C)C)C
• InChI: InChI=1S/C45H57N3O9/c1-28(2)37-40(49)46(7)35(26-32-21-15-11-16-22-32)44(53)56-39(30(5)6)42(51)48(9)36(27-33-23-17-12-18-24-33)45(54)57-38(29(3)4)41(50)47(8)34(43(52)55-37)25-31-19-13-10-14-20-31/h10-24,28-30,34-39H,25-27H2,1-9H3
• InChIKey: GYSCAQFHASJXRS-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3,9,15-tribenzyl-4,10,16-trimethyl-6,12,18-tris(propan-2-yl)-1,7,13-trioxa-4,10,16-triazacyclooctadecane-2,5,8,11,14,17-hexone
• IUPAC Traditional name: beauvericin
• Synonyms: cyclo(D-α-Hydroxyisovaleryl-L-N-methyl-Phe)3; Beauvericin; Cyclo[(2R)-2-hydroxy-3-methylbutanoyl-N-methyl-L-phenylalanyl-(2R)-2-hydroxy-3-methylbutanoyl-N-methyl-L-phenylalanyl-(2R)-2-hydroxy-3-methylbutanoyl-N-methyl-L-phenylalanyl]; Beauvericin

Database IDs

• CAS Number: 26048-05-5
• MDL Number: MFCD00056846
• PubChem SID: 24891996; 162226911
• PubChem CID: 105014

CALCULATED PROPERTIES

• Acid pKa: 18.801216
• H Acceptors: 6
• H Donor: 0
• LogD (pH = 5.5): 7.2708607
• LogD (pH = 7.4): 7.2708607
• Log P: 7.2708607
• Molar Refractivity: 213.4689 cm^3
• Polarizability: 84.44803 Å^3
• Polar Surface Area: 139.83 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥97% (HPLC)

DETAILS

Toronto Research Chemicals - B119230

Toxic depsipeptide with antibiotic and insecticidal effects.

REFERENCES

• Lee, H., et al.: J. Microbiol., Biotechnol., 18, 138 (2008)
• Moretti, A., et al.: Int. J. Food Microbiol., 127, 312 (2008)
• Jestoi, M., et al.: Food Chem., 115, 1120 (2008)
• Santini, A., et al.: Anal. Bioanal. Chem., 395, 1253 (2008)