(2S)-2-{2-[(2R)-2-[(2S)-2-amino-3-(4-hydroxyphenyl)propanamido]propanamido]-N-methylacetamido}-N-(2-hydroxyethyl)-3-phenylpropanamide

• ChemBase ID: 126860
• Molecular Formular: C26H35N5O6
• Molecular Mass: 513.586
• Monoisotopic Mass: 513.25873387
• SMILES: C[C@@H](NC(=O)[C@@H](N)Cc1ccc(O)cc1)C(=O)NCC(=O)N([C@H](C(=O)NCCO)Cc1ccccc1)C
• Canonical SMILES: OCCNC(=O)[C@@H](N(C(=O)CNC(=O)[C@H](NC(=O)[C@H](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)/t17-,21+,22+/m1/s1
• InChIKey: HPZJMUBDEAMBFI-WTNAPCKOSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-{2-[(2R)-2-[(2S)-2-amino-3-(4-hydroxyphenyl)propanamido]propanamido]-N-methylacetamido}-N-(2-hydroxyethyl)-3-phenylpropanamide
• IUPAC Traditional name: damgo
• Synonyms: Ala^2-MePhe^4-Glyol^5-Enkephalin; DAGn; DAMGE; DAMGO

Database IDs

• CAS Number: 78123-71-4
• PubChem SID: 162221187
• PubChem CID: 5462471
• CHEMBL: 38874
• Chemspider ID: 4575423
• IUPHAR ligand ID: 1647
• Wikipedia Title: DAMGO

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