2-[(1-{2-[2-(2-amino-3-carboxypropanamido)-3-hydroxypropanamido]-3-carboxypropanoyl}pyrrolidin-2-yl)formamido]-5-carbamimidamidopentanoic acid

• ChemBase ID: 103850
• Molecular Formular: C22H36N8O11
• Molecular Mass: 588.56824
• Monoisotopic Mass: 588.25035401
• SMILES: NC(CC(=O)O)C(=O)NC(CO)C(=O)NC(CC(=O)O)C(=O)N1CCCC1C(=O)NC(CCCNC(=N)N)C(=O)O
• Canonical SMILES: OCC(C(=O)NC(C(=O)N1CCCC1C(=O)NC(C(=O)O)CCCNC(=N)N)CC(=O)O)NC(=O)C(CC(=O)O)N
• InChI: InChI=1S/C22H36N8O11/c23-10(7-15(32)33)17(36)29-13(9-31)18(37)28-12(8-16(34)35)20(39)30-6-2-4-14(30)19(38)27-11(21(40)41)3-1-5-26-22(24)25/h10-14,31H,1-9,23H2,(H,27,38)(H,28,37)(H,29,36)(H,32,33)(H,34,35)(H,40,41)(H4,24,25,26)
• InChIKey: KQDIGHIVUUADBZ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[(1-{2-[2-(2-amino-3-carboxypropanamido)-3-hydroxypropanamido]-3-carboxypropanoyl}pyrrolidin-2-yl)formamido]-5-carbamimidamidopentanoic acid
• IUPAC Traditional name: 2-[(1-{2-[2-(2-amino-3-carboxypropanamido)-3-hydroxypropanamido]-3-carboxypropanoyl}pyrrolidin-2-yl)formamido]-5-carbamimidamidopentanoic acid
• Synonyms: IgE Peptide III; Hamburger Pentapeptide; ASP-SER-ASP-PRO-ARG

Database IDs

• CAS Number: 62087-72-3
• PubChem SID: 162103018
• PubChem CID: 4432414

CALCULATED PROPERTIES

• Acid pKa: 2.937104
• H Acceptors: 15
• H Donor: 11
• LogD (pH = 5.5): -11.188235
• LogD (pH = 7.4): -12.860815
• Log P: -9.977177
• Molar Refractivity: 144.4163 cm^3
• Polarizability: 52.632683 Å^3
• Polar Surface Area: 327.66 Å^2
• Rotatable Bonds: 17
• Lipinski's Rule of Five: false

REFERENCES

• Hamburger, R.N., Science, 189: 389, (1975)
• Stanworth, D.R., et al., Int. Arch. Allergy Appl. Immunol., 56: 409, (1978).