Compound: Leu-enkephalin
SMILES: O=C(O)[C@@H](NC(=O)[C@@H](NC(=O)CNC(=O)CNC(=O)[C@@H](N)Cc1ccc(O)cc1)Cc2ccccc2)CC(C)C
InChIKey: URLZCHNOLZSCCA-VABKMULXSA-N
Synonyms: Leu-enkephalin, [Leu]enkephalin, (Leu)enkephalin, CHEBI:89656, (2S)-2-[(2S)-2-(2-{2-[(2S)-2-AMINO-3-(4-HYDROXYPHENYL)PROPANAMIDO]ACETAMIDO}ACETAMIDO)-3-PHENYLPROPANAMIDO]-4-METHYLPENTANOIC ACID, (2S)-2-((2S)-2-(2-(2-((2S)-2-amino-3-(4-hydroxyphenyl)propanamido)acetamido)acetamido)-3-phenylpropanamido)-4-methylpentanoic acid, RefChem:1088416, 2-((2-((2-((2-((2-amino-3-(4-hydroxyphenyl)propanoyl)amino)acetyl)amino)acetyl)amino)-3-phenylpropanoyl)amino)-4-methylpentanoic acid, [Leu5]-Enkephalin, 58822-25-6, leucine enkephalin, Enkephalin, Tyr-Gly-Gly-Phe-Leu, Enkephalins, Enkephalin L, Leucyl-enkephalin, Leucine-enkephalin, ENKEPHALIN, LEUCINE, H-Tyr-Gly-Gly-Phe-Leu-OH, [5-Leucine]Enkephalin, Leu5-Enkephalin, Tyr-Gly-Gly-Phe-Leu-OH, [Leu 5]enkephalin, (2S)-2-[[(2S)-2-[[2-[[2-[[(2S)-2-amino-3-(4-hydroxyphenyl)propanoyl]amino]acetyl]amino]acetyl]amino]-3-phenylpropanoyl]amino]-4-methylpentanoic acid, L-Tyrosylglycylglycyl-L-phenylalanyl-L-leucine, MFCD00076406, 14-18-6, CHEMBL8234, L-Tyr-Gly-Gly-L-Phe-L-Leu, RI01R707R6, C28H37N5O7, N-(N-(N-(N-L-Tyrosylglycyl)glycyl)-L-phenylalanyl)-L-leucine, 59141-40-1, Leu-enkephalin;Leucine enkephalin;Leucyl-enkephalin, L-Leucine, N-(N-(N-(N-L-tyrosylglycyl)glycyl)-L-phenylalanyl)-, Dynorphin-(1-5), UNII-RI01R707R6, TyrGlyGlyPheLeu, CCRIS 6338, NSC350588, NSC-350588, DTXSID00905127, LeuENK, Leucine- enkephalin, EINECS 261-457-1, Leu-ENK, [Leu(5)]enkephalin, ICI 114740, NSC 350588, [Leu(5)]-enkephalin, PENTAPEPTIDE-5, L-ENK, Dynorphin A (1-5), SM-PEPTIDE-1, SH-PENTAPEPTIDE-5, L-Leucine-enkephalin acetate, Y-G-G-F-L, SCHEMBL631959, CHEMBL218452, orb1685516, GLXC-07690, H-Tyr-Gly-Gly-Phe-Leu-OH acetate, HY-P0288, BDBM50001465, BDBM50128075, MSK158449, AKOS024456832, EBC-615679, FL73373, ICI-114740, NCGC00167126-01, DA-64928, MS-30127, NS00056490, Leu-Enkephalin (H-L-Tyr-Gly-Gly-L-Phe-L-Leu-OH), Q6533903, Tyr-Gly-Pro-Phe-Leu-Arg-Arg-Ile-Arg-Arg-Lys-NH2, L-LEUCINE, L-TYROSYLGLYCYLGLYCYL-L-PHENYLALANYL-, ([Leu]-enkephalin)2-[2-(2-{2-[2-Amino-3-(4-hydroxy-phenyl)-propionylamino]-acetylamino}-acetylamino)-3-phenyl-propionylamino]-4-methyl-pentanoic acid, (2S)-2-[[(2S)-2-[[2-[[2-[[(2S)-2-amino-3-(4-hydroxyphenyl)propanoyl]amino]acetyl]amino]acetyl]amino], (2S)-2-[[(2S)-2-[[2-[[2-[[(2S)-2-amino-3-(4-hydroxyphenyl)propanoyl]amino]acetyl]amino]acetyl]amino]-3-phenyl-propanoyl]amino]-4-methyl-pentanoic acid, (enkephalin)2-[2-(2-{2-[2-Amino-3-(4-hydroxy-phenyl)-propionylamino]-acetylamino}-acetylamino)-3-phenyl-propionylamino]-4-methyl-pentanoic acid, (S)-2-[(S)-2-(2-{2-[(S)-2-Amino-3-(4-hydroxy-phenyl)-propionylamino]-acetylamino}-acetylamino)-3-phenyl-propionylamino]-4-methyl-pentanoic acid, 2-[(S)-2-(2-{2-[(S)-2-Amino-3-(4-hydroxy-phenyl)-propionylamino]-acetylamino}-acetylamino)-1-oxo-3-phenyl-propylamino]-4-methyl-pentanoic acid, 2-[(S)-2-(2-{2-[(S)-2-Amino-3-(4-hydroxy-phenyl)-propionylamino]-acetylamino}-acetylamino)-3-phenyl-propionylamino]-4-methyl-pentanoic acid, 2-[1-[1-amino-2-(4-hydroxyphenyl)-(1S)-ethylcarboxamidomethylcarboxamidomethylcarboxamido]-2-phenyl-(1S)-ethylcarboxamido]-4-methyl-(2S)-pentanoic acid, 2-[2-(2-{2-[2-Amino-3-(4-hydroxy-phenyl)-propionylamino]-acetylamino}-acetylamino)-3-phenyl-propionylamino]-4-methyl-pentanoic acid(Enkephalin), 2-{1-[1-amino-2-(4-hydroxyphenyl)ethylcarboxamidomethylcarboxamidomethylcarboxamido]-2-phenylethylcarboxamido}-4-methylpentanoic acid
Theoretical properties:
molecular_formula: C28H37N5O7
molecular_weight: 555.6 g/mol
exact_mass: 555.26929854 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 7
hydrogen_bond_acceptor_count: 8
rotatable_bond_count: 15
heavy_atom_count: 40
topological_polar_surface_area: 200 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
Descriptions:
pubchem: Leu-enkephalin is a pentapeptide comprising L-tyrosine, glycine, glycine, L-phenylalanine and L-leucine residues joined in sequence by peptide linkages. It is an endogenous opioid peptide produced in vertebrate species, including rodents, primates and humans that results from decomposition of proenkephalin or dynorphin and exhibits antinociceptive properties. It has a role as a neurotransmitter, an analgesic, a mu-opioid receptor agonist, a delta-opioid receptor agonist, a human metabolite and a rat metabolite. It is functionally related to a glycine, a L-leucine, a L-phenylalanine and a L-tyrosine. It is a tautomer of a Leu-enkephalin zwitterion.
chebi: A peptide zwitterion obtained by transfer of a proton from the carboxy to the amino terminus of Leu-enkephalin. Major species at pH 7.3.
chembl: ENKEPHALIN is a protein listed in the ChEMBL database but has not progressed to an approved clinical phase.
wikipedia: 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.