2-[2-(2-{2-[2-amino-3-(4-hydroxyphenyl)propanamido]propanamido}acetamido)-3-phenylpropanamido]-4-(methylsulfanyl)butanamide

• ChemBase ID: 105504
• Molecular Formular: C28H38N6O6S
• Molecular Mass: 586.70292
• Monoisotopic Mass: 586.25735397
• SMILES: CSCCC(NC(=O)C(Cc1ccccc1)NC(=O)CNC(=O)C(C)NC(=O)C(N)Cc1ccc(O)cc1)C(=O)N
• Canonical SMILES: CSCCC(C(=O)N)NC(=O)C(Cc1ccccc1)NC(=O)CNC(=O)C(NC(=O)C(Cc1ccc(cc1)O)N)C
• InChI: InChI=1S/C28H38N6O6S/c1-17(32-27(39)21(29)14-19-8-10-20(35)11-9-19)26(38)31-16-24(36)33-23(15-18-6-4-3-5-7-18)28(40)34-22(25(30)37)12-13-41-2/h3-11,17,21-23,35H,12-16,29H2,1-2H3,(H2,30,37)(H,31,38)(H,32,39)(H,33,36)(H,34,40)
• InChIKey: ANZXICRKKYOVMY-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[2-(2-{2-[2-amino-3-(4-hydroxyphenyl)propanamido]propanamido}acetamido)-3-phenylpropanamido]-4-(methylsulfanyl)butanamide
• IUPAC Traditional name: 2-[2-(2-{2-[2-amino-3-(4-hydroxyphenyl)propanamido]propanamido}acetamido)-3-phenylpropanamido]-4-(methylsulfanyl)butanamide
• Synonyms: [D-Ala^2, Met^5]-ENKEPHALINAMIDE

Database IDs

• CAS Number: 61090-95-7
• PubChem SID: 162092516
• PubChem CID: 100169

CALCULATED PROPERTIES

• Acid pKa: 9.509327
• H Acceptors: 7
• H Donor: 7
• LogD (pH = 5.5): -2.61224
• LogD (pH = 7.4): -0.94143945
• Log P: -0.5803278
• Molar Refractivity: 155.3228 cm^3
• Polarizability: 60.678585 Å^3
• Polar Surface Area: 205.74 Å^2
• Rotatable Bonds: 16
• Lipinski's Rule of Five: false

DETAILS

MP Biomedicals - 02190443

(Tyr-D-Ala-Gly-Phe-Met-NH₂)
A long-lasting analog with the potency of [Met^5]-enkephalin in a number of assay systems.

REFERENCES

• Pert, C.B., et al., Science, 194: 330 (1976).