2-[2-amino-3-(4-hydroxyphenyl)propanamido]-N-{[(1-hydroxy-3-phenylpropan-2-yl)carbamoyl]methyl}-4-methanesulfinylbutanamide

• ChemBase ID: 103787
• Molecular Formular: C25H34N4O6S
• Molecular Mass: 518.62566
• Monoisotopic Mass: 518.21990583
• SMILES: CS(=O)CCC(NC(=O)C(N)Cc1ccc(O)cc1)C(=O)NCC(=O)NC(CO)Cc1ccccc1
• Canonical SMILES: OCC(Cc1ccccc1)NC(=O)CNC(=O)C(NC(=O)C(Cc1ccc(cc1)O)N)CCS(=O)C
• InChI: InChI=1S/C25H34N4O6S/c1-36(35)12-11-22(29-24(33)21(26)14-18-7-9-20(31)10-8-18)25(34)27-15-23(32)28-19(16-30)13-17-5-3-2-4-6-17/h2-10,19,21-22,30-31H,11-16,26H2,1H3,(H,27,34)(H,28,32)(H,29,33)
• InChIKey: ZNLHMYPHUWWURU-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[2-amino-3-(4-hydroxyphenyl)propanamido]-N-{[(1-hydroxy-3-phenylpropan-2-yl)carbamoyl]methyl}-4-methanesulfinylbutanamide
• IUPAC Traditional name: 2-[2-amino-3-(4-hydroxyphenyl)propanamido]-N-{[(1-hydroxy-3-phenylpropan-2-yl)carbamoyl]methyl}-4-methanesulfinylbutanamide
• Synonyms: Syndyphalin SD-25; Tyr-D-Met(S=O)-Gly-Phe-ol; SYNDYPHALIN-20

Database IDs

• CAS Number: 82598-04-7
• PubChem SID: 162103110
• PubChem CID: 13042176

CALCULATED PROPERTIES

• Acid pKa: 9.507236
• H Acceptors: 7
• H Donor: 6
• LogD (pH = 5.5): -3.7887921
• LogD (pH = 7.4): -2.1680863
• Log P: -1.9243836
• Molar Refractivity: 138.0925 cm^3
• Polarizability: 53.897133 Å^3
• Polar Surface Area: 170.85 Å^2
• Rotatable Bonds: 14
• Lipinski's Rule of Five: false

DETAILS

MP Biomedicals - 02152840

A highly selective ligand for the µ-opiate receptor.

REFERENCES

• Kiso, Y., et al., Naturwissenschaften, 68: 210, (1981).