2-[3-(1H-imidazol-4-yl)-2-[(5-oxopyrrolidin-2-yl)formamido]propanamido]acetic acid

• ChemBase ID: 103842
• Molecular Formular: C13H17N5O5
• Molecular Mass: 323.30458
• Monoisotopic Mass: 323.12296867
• SMILES: OC(=O)CNC(=O)C(Cc1c[nH]cn1)NC(=O)C1CCC(=O)N1
• Canonical SMILES: OC(=O)CNC(=O)C(NC(=O)C1CCC(=O)N1)Cc1nc[nH]c1
• InChI: InChI=1S/C13H17N5O5/c19-10-2-1-8(17-10)13(23)18-9(3-7-4-14-6-16-7)12(22)15-5-11(20)21/h4,6,8-9H,1-3,5H2,(H,14,16)(H,15,22)(H,17,19)(H,18,23)(H,20,21)
• InChIKey: GVCTYSKUHKXJDZ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[3-(1H-imidazol-4-yl)-2-[(5-oxopyrrolidin-2-yl)formamido]propanamido]acetic acid; 2-[3-(1H-imidazol-5-yl)-2-[(5-oxopyrrolidin-2-yl)formamido]propanamido]acetic acid
• IUPAC Traditional name: [3-(1H-imidazol-4-yl)-2-[(5-oxopyrrolidin-2-yl)formamido]propanamido]acetic acid; [3-(3H-imidazol-4-yl)-2-[(5-oxopyrrolidin-2-yl)formamido]propanamido]acetic acid
• Synonyms: pyroGlu-His-Gly; ANOREXIGENIC PEPTIDE; pGlu-His-Gly acetate salt

Database IDs

• CAS Number: 69275-10-1
• MDL Number: MFCD00079240
• PubChem SID: 162103202
• PubChem CID: 3918406

CALCULATED PROPERTIES

• Acid pKa: 3.5495505
• H Acceptors: 6
• H Donor: 5
• LogD (pH = 5.5): -4.1409974
• LogD (pH = 7.4): -4.8599052
• Log P: -4.117848
• Molar Refractivity: 75.7504 cm^3
• Polarizability: 29.233994 Å^3
• Polar Surface Area: 153.28 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

• Storage Condition: 0°C
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

DETAILS

MP Biomedicals - 02153047

Suppresses the cephalic phase rise in serum insulin and gastrin levels.

Sigma Aldrich - P4147

Biochem/physiol Actions
Suppresses the cephalic phase rise in serum insulin and gastrin levels.1,2

REFERENCES

• Trygstad, O., et al., Acta Enocrin., 89: 176, (1978)
• Coy, D., et al., J. Physiol., 314: 225, (1981)
• Harding, D.R.K., et al., Int. J. Pept. Prot. Res., 18: 214, (1981).
• Schally, A.V., et al., Proc. Soc. Exp. Biol. Med. , 170: 264, (1982).