(2S)-2-{[(2S)-1-(2-aminoacetyl)pyrrolidin-2-yl]formamido}pentanedioic acid

• ChemBase ID: 154297
• Molecular Formular: C12H19N3O6
• Molecular Mass: 301.29576
• Monoisotopic Mass: 301.12738534
• SMILES: C1C[C@H](N(C1)C(=O)CN)C(=O)N[C@@H](CCC(=O)O)C(=O)O
• Canonical SMILES: NCC(=O)N1CCC[C@H]1C(=O)N[C@H](C(=O)O)CCC(=O)O
• InChI: InChI=1S/C12H19N3O6/c13-6-9(16)15-5-1-2-8(15)11(19)14-7(12(20)21)3-4-10(17)18/h7-8H,1-6,13H2,(H,14,19)(H,17,18)(H,20,21)/t7-,8-/m0/s1
• InChIKey: JJGBXTYGTKWGAT-YUMQZZPRSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-{[(2S)-1-(2-aminoacetyl)pyrrolidin-2-yl]formamido}pentanedioic acid
• IUPAC Traditional name: (2S)-2-{[(2S)-1-(2-aminoacetyl)pyrrolidin-2-yl]formamido}pentanedioic acid
• Synonyms: GPE; Glycyl-prolyl-glutamic acid; Gly-Pro-Glu

Database IDs

• CAS Number: 32302-76-4
• MDL Number: MFCD00144405
• PubChem SID: 162248436
• PubChem CID: 3080768

CALCULATED PROPERTIES

• Acid pKa: 3.200515
• H Acceptors: 7
• H Donor: 4
• LogD (pH = 5.5): -6.1395454
• LogD (pH = 7.4): -7.8883157
• Log P: -4.9178658
• Molar Refractivity: 69.0777 cm^3
• Polarizability: 27.338968 Å^3
• Polar Surface Area: 150.03 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: H2O: >5 mg/mL
• Apperance: white powder

Safety Information

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

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C12H19N3O6

DETAILS

Sigma Aldrich - G3923

Biochem/physiol Actions
Gly-Pro-Glu is a neuroprotective compound and the N-terminal tripeptide of IGF-1. Gly-Pro-Glu is neuroprotective after central administration in animal models of neurodegenerative processes, such as Huntington’s, Parkinson’s, Alzheimer’s diseases, and varies acute brain injury animal models. The neuroprotective activity is not related to its affinity to glutamate receptor. Findings indicate that GPE mimics insulin-like growth factor I effects on the somatostatin system through a mechanism independent of β-amyloid clearance that involves modulation of calcium and glycogen synthase kinase 3β signaling.
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. G3923.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.