octahydropyrrolo[1,2-a]piperazine-1,4-dione

• ChemBase ID: 154564
• Molecular Formular: C7H10N2O2
• Molecular Mass: 154.1665
• Monoisotopic Mass: 154.07422757
• SMILES: C1CC2C(=O)NCC(=O)N2C1
• Canonical SMILES: O=C1CNC(=O)C2N1CCC2
• InChI: InChI=1S/C7H10N2O2/c10-6-4-8-7(11)5-2-1-3-9(5)6/h5H,1-4H2,(H,8,11)
• InChIKey: OWOHLURDBZHNGG-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: octahydropyrrolo[1,2-a]piperazine-1,4-dione
• IUPAC Traditional name: hexahydropyrrolo[1,2-a]piperazine-1,4-dione
• Synonyms: (S)-3,6-Dioxohexahydropyrrolo[1,2-a]pyrazine; Glycyl-L-proline lactam; cyclo-Glycyl-L-Proline; cyclo-L-prolylglycine; cyclo-GP; Cyclo-Gly-Pro; octahydropyrrolo[1,2-a]piperazine-1,4-dione

Database IDs

• CAS Number: 3705-27-9
• MDL Number: MFCD01083707
• PubChem SID: 162248702
• PubChem CID: 193540

CALCULATED PROPERTIES

• Acid pKa: 11.351039
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): -1.3691372
• LogD (pH = 7.4): -1.3691797
• Log P: -1.3691367
• Molar Refractivity: 37.79 cm^3
• Polarizability: 14.663719 Å^3
• Polar Surface Area: 49.41 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: >10 mg/mL
• Apperance: powder
• Hydrophobicity(logP): -0.822

Safety Information

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

Product Information

• Purity: ≥98% (GC/HPLC); 95%
• Empirical Formula (Hill Notation): C7H10N2O2

DETAILS

Sigma Aldrich - C2374

Biochem/physiol Actions
Cyclo-Gly-Pro is a neuro-protective compound, an endogenous diketopiperazine, which enhances memory. In the animal model of PD, the compound improved functional recovery when administered after the onset of dyskinesia. It appears that the compound recovery function may result from non-proliferative neurogenesis that results from the inhibition of apoptosis of stem cells and/or the promotion of neuronal-orientated proliferation in the SVZ (subventricular zone).