Leu-Enkephalin
Basic information
- CAS
14-18-6- Standard SMILES
CC(C)C[C@H](NC(=O)[C@H](Cc1ccccc1)NC(=O)CNC(=O)CNC(=O)[C@@H](N)Cc1ccc(O)cc1)C(=O)O- InChIKey
URLZCHNOLZSCCA-VABKMULXSA-N- Molecular formula
- C28H37N5O7
- Average molar mass
- 555.6 g/mol
- Monoisotopic mass
- 555.26929854
Overview
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.
Names & identifiers
- Preferred name
- Leu-Enkephalin
- IUPAC
- (2S)-2-[[(2S)-2-[[2-[[2-[[(2S)-2-amino-3-(4-hydroxyphenyl)propanoyl]amino]acetyl]amino]acetyl]amino]-3-phenylpropanoyl]amino]-4-methylpentanoic acid
Names & synonyms
Leu-enkephalin[Leu]enkephalin(Leu)enkephalinCHEBI: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 acidRefChem:10884162-((2-((2-((2-((2-amino-3-(4-hydroxyphenyl)propanoyl)amino)acetyl)amino)acetyl)amino)-3-phenylpropanoyl)amino)-4-methylpentanoic acid[Leu5]-Enkephalin58822-25-6leucine enkephalinEnkephalin
Show more names
EnkephalinsEnkephalin LTyr-Gly-Gly-Phe-LeuLeucyl-enkephalinLeucine-enkephalinENKEPHALIN, LEUCINEH-Tyr-Gly-Gly-Phe-Leu-OH[5-Leucine]Enkephalin
Database identifiers
- CAS
14-18-6、58822-25-6、59141-40-1- PubChem CID
- 461776
- DTXSID
Properties
Computed structural properties
- XLogP
- -2.3
- Topological polar surface area
- 200 Ų
- Hydrogen bond donors
- 7
- Hydrogen bond acceptors
- 8
- Rotatable bonds
- 15
- Heavy atoms
- 40
- Formal charge
- 0
- Complexity
- 854
Experimental & physicochemical properties
Human DrugsPharmaceuticals
Physical DescriptionSolid
Collision Cross Section222.6 Ų [M-H]-
Chemistry & industry
Uses & manufacturing
Use ClassificationPharmaceuticals
Related reactions
3 records
Compound notes
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