ChemFOnt: Showing chemical card for Enkephalin L (CFc000000823)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:45:19 UTC

Chemfont ID

CFc000000823

Molecule Identification

Common Name

Enkephalin L

Definition

Enkephalin L is an opioid peptide. Opioid peptides are a group of neuropeptides which include enkephalins, endorphins and dynorphins. In addition to their central and peripheral antinociceptive function, opioids can modulate immune activity and cell proliferation. Enkephalins typically have a turnover rate measured in seconds to minutes, both in vivo and in vitro, and this stability is related to the age of the cell system under study. It is noteworthy that the residues most essential to enkephalin function are also either neurotransmitters themselves (glycine) or immediate precursors of L-Dopa, dopamine and norepinephrine (tyrosine and phenylalanine). The variable fifth amino acid leucine (leu5) or methionine (met5) has not yet been assigned any neurotransmitter candidacy. Again, this suggests that enkephalin is polyfunctional in that, in its intact state it elicits binding to the same sites in the brain as morphine and other opiates, and its degradation products have a potential for follow-up accessory functions by reacting as signaling entities themselves, or as the immediate precursors to inhibitory or metabotropic neurotransmitters. Enkephalins are present in macrophages infiltrating the dermal papillae in involved psoriatic skin and that the amount of enkephalin is significantly increased in involved psoriatic skin. Major enkephalin pathways in the brain involve the extrapyramidal system, including motor pathways controlled by the basal ganglia, the limbic system that governs emotional and behavioral control, and the hypothalamic-neuroendocrine axis. The apparent overlap of localization within the central nervous system of dopaminergic, glycinergic, and enkephalinergic pathways is speculated to be of neurophysiological significance, especially in light of the relatively short half-life of the enkephalins and the immediate precursor-product relationship between tyrosine and dopamine, and glycinergic signaling. Enkephalins are released into the bloodstream of mammals by the adrenal medulla. Once they are in the blood, these peptides undergo a fairly rapid hydrolysis by several plasma-contained enzymes. However, a fraction of the enkephalins present in the plasma are bound to the serum albumin, and the bound peptides are almost completely intact even after a long incubation in the presence of serum enzymes. (PMID: 9450624 , 16802191 , 4069309 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(2S)-2-[(2S)-2-(2-{2-[(2S)-2-amino-3-(4-hydroxyphenyl)propanamido]acetamido}acetamido)-3-phenylpropanamido]-4-methylpentanoic acid	ChEBI
[5-Leucine]enkephalin	ChEBI
[Leu(5)]-enkephalin	ChEBI
[Leu(5)]enkephalin	ChEBI
[Leu]enkephalin	ChEBI
Enkephalin, leucine	ChEBI
H-Tyr-gly-gly-phe-leu-OH	ChEBI
L-ENK	ChEBI
L-Tyr-gly-gly-L-phe-L-leu	ChEBI
Leu-enk	ChEBI
Leucine enkephalin	ChEBI
Leucine-enkephalin	ChEBI
Leucyl-enkephalin	ChEBI
LeuENK	ChEBI
N-(N-(N-(N-L-Tyrosylglycyl)glycyl)-L-phenylalanyl)-L-leucine	ChEBI
Tyr-gly-gly-phe-leu	ChEBI
Tyr-gly-gly-phe-leu-OH	ChEBI
Y-g-g-F-L	ChEBI
YGGFL	ChEBI
(2S)-2-[(2S)-2-(2-{2-[(2S)-2-amino-3-(4-hydroxyphenyl)propanamido]acetamido}acetamido)-3-phenylpropanamido]-4-methylpentanoate	Generator
Leucine- enkephalin	ChEMBL, HMDB
Leu-enkephalin	ChEMBL, HMDB, MeSH
[Leu 5]enkephalin	HMDB
[Leu5]-enkephalin	HMDB
Enkephalin, 5-leucine	MeSH, HMDB
Leu enkephalin	MeSH, HMDB
5 Leucine enkephalin	MeSH, HMDB
Leu(5)-enkephalin	MeSH, HMDB
5-Leucine enkephalin	MeSH, HMDB
(2S)-2-{[(2S)-2-({2-[(2-{[(2S)-2-amino-1-hydroxy-3-(4-hydroxyphenyl)propylidene]amino}-1-hydroxyethylidene)amino]-1-hydroxyethylidene}amino)-1-hydroxy-3-phenylpropylidene]amino}-4-methylpentanoate	Generator, HMDB

Chemical Formula

C₂₈H₃₇N₅O₇

Average Molecular Weight

555.6227

Monoisotopic Molecular Weight

555.269298563

IUPAC Name

(2S)-2-[(2S)-2-(2-{2-[(2S)-2-amino-3-(4-hydroxyphenyl)propanamido]acetamido}acetamido)-3-phenylpropanamido]-4-methylpentanoic acid

Traditional Name

(2S)-2-[(2S)-2-(2-{2-[(2S)-2-amino-3-(4-hydroxyphenyl)propanamido]acetamido}acetamido)-3-phenylpropanamido]-4-methylpentanoic acid

CAS Registry Number

14-18-6

SMILES

CC(C)C[C@H](NC(=O)[C@H](CC1=CC=CC=C1)NC(=O)CNC(=O)CNC(=O)[C@@H](N)CC1=CC=C(O)C=C1)C(O)=O

InChI Identifier

InChI=1S/C28H37N5O7/c1-17(2)12-23(28(39)40)33-27(38)22(14-18-6-4-3-5-7-18)32-25(36)16-30-24(35)15-31-26(37)21(29)13-19-8-10-20(34)11-9-19/h3-11,17,21-23,34H,12-16,29H2,1-2H3,(H,30,35)(H,31,37)(H,32,36)(H,33,38)(H,39,40)/t21-,22-,23-/m0/s1

InChI Key

URLZCHNOLZSCCA-VABKMULXSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as oligopeptides. These are organic compounds containing a sequence of between three and ten alpha-amino acids joined by peptide bonds.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Oligopeptides

Alternative Parents

Substituents

Alpha-oligopeptide
Tyrosine or derivatives
Phenylalanine or derivatives
Leucine or derivatives
N-acyl-alpha-amino acid
N-acyl-alpha amino acid or derivatives
N-acyl-l-alpha-amino acid
Alpha-amino acid amide
N-substituted-alpha-amino acid
Alpha-amino acid or derivatives
Amphetamine or derivatives
1-hydroxy-2-unsubstituted benzenoid
Phenol
Aralkylamine
Benzenoid
Fatty acyl
Monocyclic benzene moiety
Fatty amide
Secondary carboxylic acid amide
Amino acid or derivatives
Carboxamide group
Amino acid
Carboxylic acid
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Primary aliphatic amine
Organic oxide
Organonitrogen compound
Carbonyl group
Organooxygen compound
Organopnictogen compound
Organic nitrogen compound
Amine
Organic oxygen compound
Primary amine
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Functional Ontology

Physiological effect

Health effect

Digestive system disorder

Hepatobiliary disorder

Hepatic disorder

Cirrhosis (HMDB: HMDB0001045)
Liver disease (HMDB: HMDB0001045)

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 2583565)

Source

Endogenous

Endogenous (HMDB: HMDB0001045)

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Process

Not Available

Role

Industrial application

Pharmaceutical industry

Biomarker

Acute liver disease (MarkerDB: MDB00000296)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.015 g/L	ALOGPS
logP	-1	ALOGPS
logP	-1.9	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Acidic)	3.7	ChemAxon
pKa (Strongest Basic)	7.73	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	199.95 Å²	ChemAxon
Rotatable Bond Count	15	ChemAxon
Refractivity	145.59 m³·mol⁻¹	ChemAxon
Polarizability	57.94 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0001045

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022389

KNApSAcK ID

Not Available

Chemspider ID

406229

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Leu-enkephalin

METLIN ID

Not Available

PubChem Compound

461776

PDB ID

Not Available

ChEBI ID

89656

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for Enkephalin L (CFc000000823)

MOL for CFc000000823 (Enkephalin L)

3D MOL for CFc000000823 (Enkephalin L)

3D SDF for CFc000000823 (Enkephalin L)

3D-SDF for CFc000000823 (Enkephalin L)

PDB for CFc000000823 (Enkephalin L)

3D PDB for CFc000000823 (Enkephalin L)

SMILES for CFc000000823 (Enkephalin L)

INCHI for CFc000000823 (Enkephalin L)

Structure for CFc000000823 (Enkephalin L)

3D Structure for CFc000000823 (Enkephalin L)