Showing Compound Enkephalin L (FDB022389)

Record Information

Version

1.0

Creation date

2011-09-21 00:13:16 UTC

Update date

2015-07-21 06:57:11 UTC

Primary ID

FDB022389

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Enkephalin L

Description

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) [HMDB]

CAS Number

14-18-6

Structure

MOL SDF PDB SMILES InChI

Synonyms

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Synonym	Source
(2S)-2-[(2S)-2-(2-{2-[(2S)-2-amino-3-(4-hydroxyphenyl)propanamido]acetamido}acetamido)-3-phenylpropanamido]-4-methylpentanoate	Generator
(2S)-2-[(2S)-2-(2-{2-[(2S)-2-amino-3-(4-hydroxyphenyl)propanamido]acetamido}acetamido)-3-phenylpropanamido]-4-methylpentanoic acid	ChEBI
(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
5 Leucine enkephalin	MeSH, HMDB
5-Leucine enkephalin	MeSH, HMDB
[5-Leucine]enkephalin	ChEBI
[5-Leucine]Enkephalin	hmdb
[Leu 5]enkephalin	HMDB
[Leu(5)]-enkephalin	ChEBI
[Leu(5)]enkephalin	ChEBI

Showing 1 to 10 of 33 entries

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

Chemical Formula

C28H37N5O7

IUPAC name

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

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

Isomeric 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

Average Molecular Weight

555.6227

Monoisotopic Molecular Weight

555.269298563

Classification

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

Ontology

Biofluid and excreta:

Blood

Source:

Endogenous

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

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Property	Value	Reference
Boiling Point	Not Available
Charge	Not Available
Density	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Experimental Water Solubility	Not Available
Isoelectric point	Not Available
Mass Composition	Not Available
Melting Point	Not Available
Optical Rotation	Not Available

Showing 1 to 10 of 14 entries

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	Enkephalin L, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-01pc-2913210000-2030f7d4362602946613	Spectrum
Predicted GC-MS	Enkephalin L, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-05nf-4193224000-961c021df7886c910304	Spectrum
Predicted GC-MS	Enkephalin L, "Enkephalin L,1TMS,#1" TMS, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Enkephalin L, TMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Enkephalin L, TMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Enkephalin L, TMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Enkephalin L, TMS_1_4, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Enkephalin L, TMS_1_5, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Enkephalin L, TMS_1_6, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Enkephalin L, TMS_1_7, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Enkephalin L, TMS_2_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Enkephalin L, TMS_2_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Enkephalin L, TMS_2_4, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Enkephalin L, TMS_2_5, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Enkephalin L, TMS_2_6, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Enkephalin L, TMS_2_7, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Enkephalin L, TMS_2_8, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Enkephalin L, TMS_2_9, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Enkephalin L, TMS_2_10, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Enkephalin L, TMS_2_11, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Enkephalin L, TMS_2_12, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Enkephalin L, TMS_2_13, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Enkephalin L, TMS_2_14, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Enkephalin L, TMS_2_15, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Enkephalin L, TMS_2_16, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0f76-0940020000-01b1154dc17e8249a8c8	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-2921000000-331e8269299530ed1230	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000i-2900000000-f5b115db9b594e70d85a	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0222190000-7ff6ef9ac638217877c1	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0043-2985460000-6237cdca7e8b9de1b20d	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-003u-4952000000-fa381454fd5b34e40546	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0000090000-efdd42b91eacfd26a6f6	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-01ox-4954270000-35d9c71cc6409d67df92	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004l-5930000000-c9b69a3ab0d5f58d2de1	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-0211190000-0f087cdf9e8587268ad9	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-01qd-3528920000-f5a527ab02d072443d7d	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-007d-4910000000-994574c817d228a4f09f	2021-09-24	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

406229

ChEMBL ID

CHEMBL8234

KEGG Compound ID

Not Available

Pubchem Compound ID

461776

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB01045

CRC / DFC (Dictionary of Food Compounds) ID

Not Available

EAFUS ID

Not Available

Dr. Duke ID

Not Available

BIGG ID

Not Available

KNApSAcK ID

Not Available

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

Not Available

Wikipedia ID

Not Available

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

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Food	Content Range	Average	Reference

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Biological Effects and Interactions

Health Effects / Bioactivities

Not Available

Enzymes

Not Available

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Not Available

Files

MSDS

Not Available

References

Synthesis Reference

Not Available

General Reference

Not Available

Content Reference

Showing Compound Enkephalin L (FDB022389)

Structure for FDB022389 (Enkephalin L)