4-(2-{[1-({5-amino-1-[(1-{[1-({[(1-{[1-carbamoyl-3-(methylsulfanyl)propyl]carbamoyl}-3-methylbutyl)carbamoyl]methyl}carbamoyl)-2-(4-hydroxyphenyl)ethyl]carbamoyl}-2-phenylethyl)carbamoyl]pentyl}carbamoyl)-2-carbamoylethyl]carbamoyl}pyrrolidin-1-yl)-4-oxo-3-{2-[(5-oxopyrrolidin-2-yl)formamido]propanamido}butanoic acid

• ChemBase ID: 103478
• Molecular Formular: C58H84N14O16S
• Molecular Mass: 1265.43676
• Monoisotopic Mass: 1264.59104368
• SMILES: CSCCC(NC(=O)C(CC(C)C)NC(=O)CNC(=O)C(Cc1ccc(O)cc1)NC(=O)C(Cc1ccccc1)NC(=O)C(CCCCN)NC(=O)C(CC(=O)N)NC(=O)C1CCCN1C(=O)C(CC(=O)O)NC(=O)C(C)NC(=O)C1CCC(=O)N1)C(=O)N
• Canonical SMILES: NCCCCC(C(=O)NC(C(=O)NC(C(=O)NCC(=O)NC(C(=O)NC(C(=O)N)CCSC)CC(C)C)Cc1ccc(cc1)O)Cc1ccccc1)NC(=O)C(NC(=O)C1CCCN1C(=O)C(NC(=O)C(NC(=O)C1CCC(=O)N1)C)CC(=O)O)CC(=O)N
• InChI: InChI=1S/C58H84N14O16S/c1-31(2)25-39(54(84)66-36(49(61)79)21-24-89-4)65-47(76)30-62-51(81)40(27-34-15-17-35(73)18-16-34)68-55(85)41(26-33-11-6-5-7-12-33)69-53(83)37(13-8-9-22-59)67-56(86)42(28-45(60)74)70-57(87)44-14-10-23-72(44)58(88)43(29-48(77)78)71-50(80)32(3)63-52(82)38-19-20-46(75)64-38/h5-7,11-12,15-18,31-32,36-44,73H,8-10,13-14,19-30,59H2,1-4H3,(H2,60,74)(H2,61,79)(H,62,81)(H,63,82)(H,64,75)(H,65,76)(H,66,84)(H,67,86)(H,68,85)(H,69,83)(H,70,87)(H,71,80)(H,77,78)
• InChIKey: SHSUJLMLURFKID-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-(2-{[1-({5-amino-1-[(1-{[1-({[(1-{[1-carbamoyl-3-(methylsulfanyl)propyl]carbamoyl}-3-methylbutyl)carbamoyl]methyl}carbamoyl)-2-(4-hydroxyphenyl)ethyl]carbamoyl}-2-phenylethyl)carbamoyl]pentyl}carbamoyl)-2-carbamoylethyl]carbamoyl}pyrrolidin-1-yl)-4-oxo-3-{2-[(5-oxopyrrolidin-2-yl)formamido]propanamido}butanoic acid
• IUPAC Traditional name: physalaemin; 4-(2-{[1-({5-amino-1-[(1-{[1-({[(1-{[1-carbamoyl-3-(methylsulfanyl)propyl]carbamoyl}-3-methylbutyl)carbamoyl]methyl}carbamoyl)-2-(4-hydroxyphenyl)ethyl]carbamoyl}-2-phenylethyl)carbamoyl]pentyl}carbamoyl)-2-carbamoylethyl]carbamoyl}pyrrolidin-1-yl)-4-oxo-3-{2-[(5-oxopyrrolidin-2-yl)formamido]propanamido}butanoic acid
• Synonyms: pGlu-Ala-Asp-Pro-Asn-Lys-Phe-Tyr-Gly-Leu-Met-NH2; Physalaemin; pyroGlu-Ala-Asp-Pro-Asn-Lys-Phe-Tyr-Gly-Leu-Met-NH₂; PHYSALAEMIN

Database IDs

• CAS Number: 2507-24-6
• MDL Number: MFCD00076375
• PubChem SID: 24898279; 162090598
• PubChem CID: 17268

CALCULATED PROPERTIES

• Acid pKa: 3.6792154
• H Acceptors: 17
• H Donor: 15
• LogD (pH = 5.5): -6.933743
• LogD (pH = 7.4): -6.9325056
• Log P: -6.930116
• Molar Refractivity: 319.2656 cm^3
• Polarizability: 124.98456 Å^3
• Polar Surface Area: 481.04 Å^2
• Rotatable Bonds: 37
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

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

Pharmacology Properties

• Gene Information: human ... INS(3630)

Product Information

• Purity: ≥97% (HPLC)

DETAILS

MP Biomedicals - 02151883

A powerful vasodilator and hypotensive agent.

Sigma Aldrich - P2149

Biochem/physiol Actions
Potent hypotensive; induces salivation, intestinal contraction and vasodilation
Other Notes
Tachykinin originally isolated from the skin of the amphibian, Physalaemus fuscumaculatus; with structural homology to substance P

REFERENCES

• Bertaccini, G., et al., Br. J. Pharmac., 25: 380 (1965).