(3S,6S)-3,6-bis(2-methylpropyl)piperazine-2,5-dione

• ChemBase ID: 165227
• Molecular Formular: C12H22N2O2
• Molecular Mass: 226.31528
• Monoisotopic Mass: 226.16812795
• SMILES: [C@@H]1(C(=O)N[C@H](C(=O)N1)CC(C)C)CC(C)C
• Canonical SMILES: CC(C[C@@H]1NC(=O)[C@@H](NC1=O)CC(C)C)C
• InChI: InChI=1S/C12H22N2O2/c1-7(2)5-9-11(15)14-10(6-8(3)4)12(16)13-9/h7-10H,5-6H2,1-4H3,(H,13,16)(H,14,15)/t9-,10-/m0/s1
• InChIKey: XWYXUMDVQIOAPR-UWVGGRQHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3S,6S)-3,6-bis(2-methylpropyl)piperazine-2,5-dione
• IUPAC Traditional name: (3S,6S)-3,6-bis(2-methylpropyl)piperazine-2,5-dione
• Synonyms: (3S,6S)-3,6-Bis(2-methylpropyl)-2,5-piperazinedione; (3S-cis)-3,6-Bis(2-methylpropyl)-2,5-piperazinedione; Cyclo(L-leucyl-L-leucyl); Cyclo(leucylleucine); Cyclo-L-Leu-L-Leu; Cyclo(Leu-Leu)

Database IDs

• CAS Number: 952-45-4
• PubChem SID: 162259360
• PubChem CID: 192731

CALCULATED PROPERTIES

• Acid pKa: 11.386027
• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): 1.4351819
• LogD (pH = 7.4): 1.4351426
• Log P: 1.4351823
• Molar Refractivity: 61.942 cm^3
• Polarizability: 24.530186 Å^3
• Polar Surface Area: 58.2 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - C988300

A cyclic peptide, one of the secondary metabolite of a mangrove endophytic fungus (No. 1947) from the South China Sea.

REFERENCES

• Carmichael, J., et al.: Cancer Res., 47, 936 (1987)
• Blunt, J., et al.: Nat. Prod. Rep., 20, 1 (1987)
• Mitova, M., et al.: J. Nat. Prod., 67, 1178 (1987)