(3S,8aS)-3-(2-methylpropyl)-octahydropyrrolo[1,2-a]piperazine-1,4-dione

• ChemBase ID: 165149
• Molecular Formular: C11H18N2O2
• Molecular Mass: 210.27282
• Monoisotopic Mass: 210.13682783
• SMILES: N1[C@H](C(=O)N2[C@H](C1=O)CCC2)CC(C)C
• Canonical SMILES: CC(C[C@@H]1NC(=O)[C@H]2N(C1=O)CCC2)C
• InChI: InChI=1S/C11H18N2O2/c1-7(2)6-8-11(15)13-5-3-4-9(13)10(14)12-8/h7-9H,3-6H2,1-2H3,(H,12,14)/t8-,9-/m0/s1
• InChIKey: SZJNCZMRZAUNQT-IUCAKERBSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3S,8aS)-3-(2-methylpropyl)-octahydropyrrolo[1,2-a]piperazine-1,4-dione
• IUPAC Traditional name: (3S,8aS)-3-(2-methylpropyl)-hexahydropyrrolo[1,2-a]piperazine-1,4-dione
• Synonyms: (3S-trans)-Hexahydro-3-(2-methylpropyl)-pyrrolo[1,2-a]pyrazine-1,4-dione; 3-Isobutylhexahydropyrrolo [1,2-a] pyrazine-1,4-dione; Cyclo(L-Leu-L-Pro); Cyclo(L-Pro-D-Leu); Cyclo(L-Pro-L-Leu); Cyclo(L-leucyl-L-prolyl); Cyclo(L-prolyl-L-leucyl); Cyclo(Pro-Leu); Cyclo(proline-leucine); Cyclo-L-prolyl-L-leucine; Gancidin W; L-Leucyl-L-proline lactam; L-Leucyl-L-prolyl lactam; Maculosin 6; Cyclo(L-prolyl-L-leucyl)

Database IDs

• CAS Number: 2873-36-1
• PubChem SID: 162259282
• PubChem CID: 7074739

CALCULATED PROPERTIES

• Acid pKa: 11.471552
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 0.45373732
• LogD (pH = 7.4): 0.4537051
• Log P: 0.45373774
• Molar Refractivity: 55.9575 cm^3
• Polarizability: 21.975462 Å^3
• Polar Surface Area: 49.41 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Dichloromethane; Ethyl Acetate; Methanol
• Apperance: White Solid
• Melting Point: 163-165°C

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - C987660

Sorbicillin analog. A bioactive secondary metabolites from terrestrial Streptomyces species TN262.

REFERENCES

• Ma, L. et al. : J. Anitibiot. 64, 645 (2011)
• Elleuch, L. et al.: Appl. Biochem. Biotech. 162, 579 (2010)