ChemFOnt: Showing chemical card for N-Nervonoyl Glutamic acid (CFc000222343)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-14 01:43:03 UTC

Chemfont ID

CFc000222343

Molecule Identification

Common Name

N-Nervonoyl Glutamic acid

Definition

N-nervonoyl glutamic acid, also known as N-nervonoyl glutamate belongs to the class of compounds known as N-acylamides. These are molecules characterized by a fatty acyl group linked to a primary amine by an amide bond. More specifically, it is a Nervonic acid amide of Glutamic acid. It is believed that there are more than 800 types of N-acylamides in the human body. N-acylamides fall into several categories: amino acid conjugates (e.g., those acyl amides conjugated with amino acids), neurotransmitter conjugates (e.g., those acylamides conjugated with neurotransmitters), ethanolamine conjugates (e.g., those acylamides conjugated to ethanolamine), and taurine conjugates (e.g., those acyamides conjugated to taurine). N-Nervonoyl Glutamic acid is an amino acid conjugate. N-acylamides can be classified into 9 different categories depending on the size of their acyl-group: 1) short-chain N-acylamides; 2) medium-chain N-acylamides; 3) long-chain N-acylamides; and 4) very long-chain N-acylamides; 5) hydroxy N-acylamides; 6) branched chain N-acylamides; 7) unsaturated N-acylamides; 8) dicarboxylic N-acylamides and 9) miscellaneous N-acylamides. N-Nervonoyl Glutamic acid is therefore classified as a very long chain N-acylamide. N-acyl amides have a variety of signaling functions in physiology, including in cardiovascular activity, metabolic homeostasis, memory, cognition, pain, motor control and others (PMID: 15655504 ). N-acyl amides have also been shown to play a role in cell migration, inflammation and certain pathological conditions such as diabetes, cancer, neurodegenerative disease, and obesity (PMID: 23144998 ; PMID: 25136293 ; PMID: 28854168 ).N-acyl amides can be synthesized both endogenously and by gut microbiota (PMID: 28854168 ). N-acylamides can be biosynthesized via different routes, depending on the parent amine group. N-acyl ethanolamines (NAEs) are formed via the hydrolysis of an unusual phospholipid precursor, N-acyl-phosphatidylethanolamine (NAPE), by a specific phospholipase D. N-acyl amino acids are synthesized via a circulating peptidase M20 domain containing 1 (PM20D1), which can catalyze the bidirectional the condensation and hydrolysis of a variety of N-acyl amino acids. The degradation of N-acylamides is largely mediated by an enzyme called fatty acid amide hydrolase (FAAH), which catalyzes the hydrolysis of N-acylamides into fatty acids and the biogenic amines. Many N-acylamides are involved in lipid signaling system through interactions with transient receptor potential channels (TRP). TRP channel proteins interact with N-acyl amides such as N-arachidonoyl ethanolamide (Anandamide), N-arachidonoyl dopamine and others in an opportunistic fashion (PMID: 23178153 ). This signaling system has been shown to play a role in the physiological processes involved in inflammation (PMID: 25136293 ). Other N-acyl amides, including N-oleoyl-glutamine, have also been characterized as TRP channel antagonists (PMID: 29967167 ). N-acylamides have also been shown to have G-protein-coupled receptors (GPCRs) binding activity (PMID: 28854168 ). The study of N-acylamides is an active area of research and it is likely that many novel N-acylamides will be discovered in the coming years. It is also likely that many novel roles in health and disease will be uncovered for these molecules.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
N-Nervonoyl glutamate	Generator

Chemical Formula

C₂₉H₅₃NO₅

Average Molecular Weight

495.745

Monoisotopic Molecular Weight

495.392373811

IUPAC Name

2-(tetracos-15-enamido)pentanedioic acid

Traditional Name

2-(tetracos-15-enamido)pentanedioic acid

CAS Registry Number

Not Available

SMILES

CCCCCCCCC=CCCCCCCCCCCCCCC(=O)NC(CCC(O)=O)C(O)=O

InChI Identifier

InChI=1S/C29H53NO5/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22-23-27(31)30-26(29(34)35)24-25-28(32)33/h9-10,26H,2-8,11-25H2,1H3,(H,30,31)(H,32,33)(H,34,35)

InChI Key

XZIVABANOODAQU-UHFFFAOYSA-N

Chemical Taxonomy

Classification

Not classified

Functional Ontology

Not Available

Not Available

Not Available

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	5.0e-05 g/L	ALOGPS
logP	7.81	ALOGPS
logP	8.56	ChemAxon
logS	-7	ALOGPS
pKa (Strongest Acidic)	3.62	ChemAxon
pKa (Strongest Basic)	-1.3	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	103.7 Å²	ChemAxon
Rotatable Bond Count	26	ChemAxon
Refractivity	143.1 m³·mol⁻¹	ChemAxon
Polarizability	62.82 Å³	ChemAxon
Number of Rings	0	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

HMDB0242090

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for N-Nervonoyl Glutamic acid (CFc000222343)

MOL for CFc000222343 (N-Nervonoyl Glutamic acid)

3D MOL for CFc000222343 (N-Nervonoyl Glutamic acid)

3D SDF for CFc000222343 (N-Nervonoyl Glutamic acid)

3D-SDF for CFc000222343 (N-Nervonoyl Glutamic acid)

PDB for CFc000222343 (N-Nervonoyl Glutamic acid)

3D PDB for CFc000222343 (N-Nervonoyl Glutamic acid)

SMILES for CFc000222343 (N-Nervonoyl Glutamic acid)

INCHI for CFc000222343 (N-Nervonoyl Glutamic acid)

Structure for CFc000222343 (N-Nervonoyl Glutamic acid)

3D Structure for CFc000222343 (N-Nervonoyl Glutamic acid)