Structure via PubChem · Public domain (PubChem)
leucine enkephalin
Sign in to saveAlso known as [5-Leucine]Enkephalin, [leu]enkephalin, [Leu5]-Enkephalin, [Leu 5]enkephalin, Leu-enkaphalin
Leu-enkephalin is an endogenous opioid peptide neurotransmitter with the amino acid sequence Tyr-Gly-Gly-Phe-Leu that is found naturally in the brains of many animals, including humans. It is one of the two forms of enkephalin; the other is met-enkephalin. The tyrosine residue at position 1 is thought to be analogous to the 3-hydroxyl group on morphine. Leu-enkephalin has agonistic actions at both the μ- and δ-opioid receptors, with significantly greater preference for the latter. It has little to no effect on the κ-opioid receptor.
Chemical data
- Formula
- C28H37N5O7
- Molecular weight
- 555.6 g/mol
- IUPAC name
- (2S)-2-[[(2S)-2-[[2-[[2-[[(2S)-2-amino-3-(4-hydroxyphenyl)propanoyl]amino]acetyl]amino]acetyl]amino]-3-phenylpropanoyl]amino]-4-methylpentanoic acid
- SMILES
- CC(C)C[C@@H](C(=O)O)NC(=O)[C@H](CC1=CC=CC=C1)NC(=O)CNC(=O)CNC(=O)[C@H](CC2=CC=C(C=C2)O)N
- InChIKey
- URLZCHNOLZSCCA-VABKMULXSA-N
- XLogP
- -2.3
- Polar surface area
- 200 Ų
- H-bond donors
- 7
- H-bond acceptors
- 8
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Molecule type
- Protein
via ChEMBL · EBI
Wikidata facts
- Subclass of
- enkephalin
- Mass
- 555.269
Show 4 more facts
- found in taxon
- Mytilus edulis
- chemical formula
- C₂₈H₃₇N₅O₇
- isomeric SMILES
- CC(C)C[C@@H](C(=O)O)NC(=O)[C@H](CC1=CC=CC=C1)NC(=O)CNC(=O)CNC(=O)[C@H](CC2=CC=C(C=C2)O)N
- canonical SMILES
- CC(C)CC(C(=O)O)NC(=O)C(CC1=CC=CC=C1)NC(=O)CNC(=O)CNC(=O)C(CC2=CC=C(C=C2)O)N
Sources (2)
via Wikidata · CC0
~1 min read
Encyclopedic overview
2 sectionsContents
- See also
- References
Leu-enkephalin is an endogenous opioid peptide neurotransmitter with the amino acid sequence Tyr-Gly-Gly-Phe-Leu that is found naturally in the brains of many animals, including humans. It is one of the two forms of enkephalin; the other is met-enkephalin. The tyrosine residue at position 1 is thought to be analogous to the 3-hydroxyl group on morphine. Leu-enkephalin has agonistic actions at both the μ- and δ-opioid receptors, with significantly greater preference for the latter. It has little to no effect on the κ-opioid receptor.
A nasal spray formulation of leu-enkephalin (developmental code names NES-100, NM-0127, NM-127, PES-200; proposed brand name Envelta) is under development by Virpax Pharmaceuticals for the treatment of pain and post-traumatic stress disorder (PTSD). As of November 2023, it is up to the preclinical stage of development for these indications.
Excerpted from Wikipedia’s “leucine enkephalin” article, available under the CC BY-SA 4.0 licence.