Eluxadoline
5-[[[(2S)-2-amino-3-(4-carbamoyl-2,6-dimethylphenyl)propanoyl]-[(1S)-1-(5-phenyl-1H-imidazol-2-yl)ethyl]amino]methyl]-2-methoxybenzoic acid
Molecular Identity
Eluxadoline
5-[[[(2S)-2-amino-3-(4-carbamoyl-2,6-dimethylphenyl)propanoyl]-[(1S)-1-(5-phenyl-1H-imidazol-2-yl)ethyl]amino]methyl]-2-methoxybenzoic acid
PubChem CID: 11250029
Eluxadoline is an amino acid amide obtained by the formal condensation of the carboxy group of 4-carbamoyl-2,6-dimethyl-L-phenylalanine with the secondary amino group of 2-methoxy-5-({[(1S)-1-(4-phenylimidazol-2-yl)ethyl]amino}methyl)benzoic acid. It has mixed opioid receptor activity and is used for treatment of irritable bowel syndrome with diarrhoea. It has a role as a mu-opioid receptor agonist, a gastrointestinal drug, a kappa-opioid receptor agonist and a delta-opioid receptor antagonist. It is an amino acid amide, a member of benzamides, a member of imidazoles, a methoxybenzoic acid and a L-phenylalanine derivative.
2D Structure
Properties
C32H35N5O5
Molecular Formula
569.60
Molecular Weight
g/mol
569.2638
Exact Mass
Da
0.9
XLogP
Drug-like (Lipinski: < 5)
165
TPSA
May have limited oral absorption
4
H-Bond Donors
7
H-Bond Acceptors
917
Complexity
SMILES
Canonical SMILES
SMILES: CC1=CC(=CC(=C1CC(C(=O)N(CC2=CC(=C(C=C2)OC)C(=O)O)C(C)C3=NC=C(N3)C4=CC=CC=C4)N)C)C(=O)NIsomeric SMILES
SMILES: CC1=CC(=CC(=C1C[C@@H](C(=O)N(CC2=CC(=C(C=C2)OC)C(=O)O)[C@@H](C)C3=NC=C(N3)C4=CC=CC=C4)N)C)C(=O)NSynonyms(20)
Eluxadoline864821-90-9ViberzitruberziJNJ-27018966eluxadolina45TPJ4MBQ1CHEBI:85980DTXSID70235589Benzoic acid, 5-((((2S)-2-amino-3-(4-(aminocarbonyl)-2,6-dimethylphenyl)-1-oxopropyl)((1S)-1-(5-phenyl-1H-imidazol-2-yl)ethyl)amino)methyl)-2-methoxy-5-({(4-carbamoyl-2,6-dimethyl-L-phenylalanyl)[(1S)-1-(4-phenyl-1H-imidazol-2-yl)ethyl]amino}methyl)-2-methoxybenzoic acideluxadolinum5-((((2S)-2-amino-3-(4-carbamoyl-2,6-dimethylphenyl)propanoyl)-((1S)-1-(4-phenyl-3H-imidazol-2-yl)ethyl)amino)methyl)-2-methoxybenzoic acid5-(((4-carbamoyl-2,6-dimethyl-L-phenylalanyl)((1S)-1-(4-phenyl-1H-imidazol-2-yl)ethyl)amino)methyl)-2-methoxybenzoic acid5-[[[(2S)-2-amino-3-(4-carbamoyl-2,6-dimethylphenyl)propanoyl]-[(1S)-1-(4-phenyl-3H-imidazol-2-yl)ethyl]amino]methyl]-2-methoxybenzoic acid
Data from PubChem (NCBI)
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