5-(2-carbamoylpyrrolidin-1-yl)-5-oxo-4-[(5-oxopyrrolidin-2-yl)formamido]pentanoic acid

• ChemBase ID: 133634
• Molecular Formular: C15H22N4O6
• Molecular Mass: 354.35838
• Monoisotopic Mass: 354.15393444
• SMILES: C1CC(N(C1)C(=O)C(CCC(=O)O)NC(=O)C1CCC(=O)N1)C(=O)N
• Canonical SMILES: OC(=O)CCC(C(=O)N1CCCC1C(=O)N)NC(=O)C1CCC(=O)N1
• InChI: InChI=1S/C15H22N4O6/c16-13(23)10-2-1-7-19(10)15(25)9(4-6-12(21)22)18-14(24)8-3-5-11(20)17-8/h8-10H,1-7H2,(H2,16,23)(H,17,20)(H,18,24)(H,21,22)
• InChIKey: HYZBGWLLSXSYLX-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-(2-carbamoylpyrrolidin-1-yl)-5-oxo-4-[(5-oxopyrrolidin-2-yl)formamido]pentanoic acid
• IUPAC Traditional name: 5-(2-carbamoylpyrrolidin-1-yl)-5-oxo-4-[(5-oxopyrrolidin-2-yl)formamido]pentanoic acid
• Synonyms: Fertilization Promoting Peptide; pGlu-Glu-Pro Amide

Database IDs

• CAS Number: 85541-78-2
• MDL Number: MFCD00076815
• PubChem SID: 24898265; 162227911
• PubChem CID: 4267593

CALCULATED PROPERTIES

• Acid pKa: 4.174834
• H Acceptors: 6
• H Donor: 4
• LogD (pH = 5.5): -4.192668
• LogD (pH = 7.4): -5.900612
• Log P: -2.8501353
• Molar Refractivity: 82.9843 cm^3
• Polarizability: 32.524544 Å^3
• Polar Surface Area: 158.9 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

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

Product Information

• Purity: ≥97% (HPLC)

DETAILS

Sigma Aldrich - P2053

Amino Acid Sequence
Glp-Glu-Pro-NH2
Biochem/physiol Actions
TRH analog that is produced in the thyroid, mammary gland and prostate. Promotes fertilization by enhancing sperm function.