6-amino-2-{2-[2-(2-{2-[2-amino-3-(4-hydroxyphenyl)propanamido]acetamido}acetamido)-3-phenylpropanamido]-4-(methylsulfanyl)butanamido}hexanoic acid

• ChemBase ID: 103782
• Molecular Formular: C33H47N7O8S
• Molecular Mass: 701.83338
• Monoisotopic Mass: 701.3206825
• SMILES: CSCCC(NC(=O)C(Cc1ccccc1)NC(=O)CNC(=O)CNC(=O)C(N)Cc1ccc(O)cc1)C(=O)NC(CCCCN)C(=O)O
• Canonical SMILES: NCCCCC(C(=O)O)NC(=O)C(NC(=O)C(Cc1ccccc1)NC(=O)CNC(=O)CNC(=O)C(Cc1ccc(cc1)O)N)CCSC
• InChI: InChI=1S/C33H47N7O8S/c1-49-16-14-25(31(45)40-26(33(47)48)9-5-6-15-34)39-32(46)27(18-21-7-3-2-4-8-21)38-29(43)20-36-28(42)19-37-30(44)24(35)17-22-10-12-23(41)13-11-22/h2-4,7-8,10-13,24-27,41H,5-6,9,14-20,34-35H2,1H3,(H,36,42)(H,37,44)(H,38,43)(H,39,46)(H,40,45)(H,47,48)
• InChIKey: CFOVZGFKVVQYMH-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 6-amino-2-{2-[2-(2-{2-[2-amino-3-(4-hydroxyphenyl)propanamido]acetamido}acetamido)-3-phenylpropanamido]-4-(methylsulfanyl)butanamido}hexanoic acid
• IUPAC Traditional name: 6-amino-2-{2-[2-(2-{2-[2-amino-3-(4-hydroxyphenyl)propanamido]acetamido}acetamido)-3-phenylpropanamido]-4-(methylsulfanyl)butanamido}hexanoic acid
• Synonyms: Tyr-Gly-Gly-Phe-Met-Lys; [Met^5]-ENKEPHALIN-Lys

Database IDs

• CAS Number: 75909-25-0
• PubChem SID: 162102911
• PubChem CID: 14574437

CALCULATED PROPERTIES

• Acid pKa: 3.6237705
• H Acceptors: 10
• H Donor: 9
• LogD (pH = 5.5): -5.3094664
• LogD (pH = 7.4): -3.6344602
• Log P: -3.297215
• Molar Refractivity: 183.6163 cm^3
• Polarizability: 71.96231 Å^3
• Polar Surface Area: 255.07 Å^2
• Rotatable Bonds: 22
• Lipinski's Rule of Five: false

REFERENCES

• Stern, A.S., et al., Arch. Biochem. Biophys., 205: 606 (1980).