2-amino-N-(1-{[({1-[(2-hydroxyethyl)carbamoyl]-2-phenylethyl}(methyl)carbamoyl)methyl]carbamoyl}ethyl)-3-(4-hydroxyphenyl)propanamide

• ChemBase ID: 103162
• Molecular Formular: C26H35N5O6
• Molecular Mass: 513.586
• Monoisotopic Mass: 513.25873387
• SMILES: CC(NC(=O)C(N)Cc1ccc(O)cc1)C(=O)NCC(=O)N(C)C(Cc1ccccc1)C(=O)NCCO
• Canonical SMILES: OCCNC(=O)C(N(C(=O)CNC(=O)C(NC(=O)C(Cc1ccc(cc1)O)N)C)C)Cc1ccccc1
• InChI: InChI=1S/C26H35N5O6/c1-17(30-25(36)21(27)14-19-8-10-20(33)11-9-19)24(35)29-16-23(34)31(2)22(26(37)28-12-13-32)15-18-6-4-3-5-7-18/h3-11,17,21-22,32-33H,12-16,27H2,1-2H3,(H,28,37)(H,29,35)(H,30,36)
• InChIKey: HPZJMUBDEAMBFI-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-amino-N-(1-{[({1-[(2-hydroxyethyl)carbamoyl]-2-phenylethyl}(methyl)carbamoyl)methyl]carbamoyl}ethyl)-3-(4-hydroxyphenyl)propanamide
• IUPAC Traditional name: damgo
• Synonyms: DAGO; Tyr-D-Ala-Gly-N-Methyl-Phe-Gly-ol; (D-Ala^2,N-Methyl-Phe^4,Gly-ol^5)-ENKEPHALIN TRIFLUOROACETATE SALT

Database IDs

• CAS Number: 100929-53-1
• PubChem SID: 162090625
• PubChem CID: 4488326

CALCULATED PROPERTIES

• Acid pKa: 9.510376
• H Acceptors: 7
• H Donor: 6
• LogD (pH = 5.5): -2.9699023
• LogD (pH = 7.4): -1.2990922
• Log P: -0.93769467
• Molar Refractivity: 137.0224 cm^3
• Polarizability: 53.33679 Å^3
• Polar Surface Area: 174.09 Å^2
• Rotatable Bonds: 13
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• Storage Condition: -20°C

DETAILS

MP Biomedicals - 02150776

An analog which selectively binds to μ opioid receptors.

REFERENCES

• Handa, B.K., et al., Eur. J. Pharmac. , 70 : 531 (1981).
• Kosterlitz, H.W., et al., Br. J. Pharmac. , 73 : 229 (1981).