2-[(1-{2-[2-(2-amino-5-carbamimidamidopentanamido)-3-(4-hydroxyphenyl)propanamido]-4-methylpentanoyl}pyrrolidin-2-yl)formamido]-3-hydroxybutanoic acid

• ChemBase ID: 103489
• Molecular Formular: C30H48N8O8
• Molecular Mass: 648.75092
• Monoisotopic Mass: 648.35951054
• SMILES: CC(C)CC(NC(=O)C(Cc1ccc(O)cc1)NC(=O)C(N)CCCNC(=N)N)C(=O)N1CCCC1C(=O)NC(C(C)O)C(=O)O
• Canonical SMILES: CC(CC(C(=O)N1CCCC1C(=O)NC(C(=O)O)C(O)C)NC(=O)C(NC(=O)C(CCCNC(=N)N)N)Cc1ccc(cc1)O)C
• InChI: InChI=1S/C30H48N8O8/c1-16(2)14-22(28(44)38-13-5-7-23(38)27(43)37-24(17(3)39)29(45)46)36-26(42)21(15-18-8-10-19(40)11-9-18)35-25(41)20(31)6-4-12-34-30(32)33/h8-11,16-17,20-24,39-40H,4-7,12-15,31H2,1-3H3,(H,35,41)(H,36,42)(H,37,43)(H,45,46)(H4,32,33,34)
• InChIKey: KKUPPLMEDQDAJX-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[(1-{2-[2-(2-amino-5-carbamimidamidopentanamido)-3-(4-hydroxyphenyl)propanamido]-4-methylpentanoyl}pyrrolidin-2-yl)formamido]-3-hydroxybutanoic acid
• IUPAC Traditional name: 2-[(1-{2-[2-(2-amino-5-carbamimidamidopentanamido)-3-(4-hydroxyphenyl)propanamido]-4-methylpentanoyl}pyrrolidin-2-yl)formamido]-3-hydroxybutanoic acid
• Synonyms: Arg-Tyr-Leu-Pro-Thr; PROCTOLIN

Database IDs

• CAS Number: 57966-42-4
• PubChem SID: 162090390
• PubChem CID: 14213881

CALCULATED PROPERTIES

• Acid pKa: -0.7563143
• H Acceptors: 12
• H Donor: 10
• LogD (pH = 5.5): -5.2339935
• LogD (pH = 7.4): -3.5557325
• Log P: -3.1742795
• Molar Refractivity: 177.0378 cm^3
• Polarizability: 65.06347 Å^3
• Polar Surface Area: 273.29 Å^2
• Rotatable Bonds: 17
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• Storage Condition: -20°C

DETAILS

MP Biomedicals - 02151949

An insect neurotransmitter.

REFERENCES

• Starratt, A.N. and Brown, B.E., Life Sci., 17: 1253 (1976).
• O'Shea, M., et al., Science, 213: 567 (1981).