ChemFOnt: Showing chemical card for gamma-Aminobutyryllysine (CFc000001309)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:45:55 UTC

Chemfont ID

CFc000001309

Molecule Identification

Common Name

gamma-Aminobutyryllysine

Definition

gamma-Aminobutyryllysine, also known as N2-(4-amino-1-oxobutyl)-lysine, belongs to the class of organic compounds known as hybrid peptides. Hybrid peptides are compounds containing at least two different types of amino acids (alpha, beta, gamma, delta) linked to each other through a peptide bond. gamma-Aminobutyryllysine is a very strong basic compound (based on its pKa). gamma-Aminobutyryllysine is a dipeptide present in the human brain. This dipeptide occurs in much higher concentrations in the human brain than in the brains of lower mammals (PMID: 5559257 ). Adult brain and cerebrospinal fluid gamma-aminobutyryllysine levels and adult brain homocarnosine levels are higher than those found in children (PMID: 5031796 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
g-Aminobutyryl-lysine	Generator
Γ-aminobutyryl-lysine	Generator
L-N2-(4-Aminobutyryl)-lysine	HMDB
N2-(4-Aminobutyryl)-lysine	HMDB
Na-(g-aminobutyryl)-L-lysine	HMDB
Na-(g-aminobutyryl)lysine	HMDB
Na-(gamma-aminobutyryl)-L-lysine	HMDB
Na-(gamma-aminobutyryl)lysine	HMDB
Nalpha-(g-aminobutyryl)-L-lysine	HMDB
Nalpha-(g-aminobutyryl)lysine	HMDB
Nalpha-(gamma-aminobutyryl)-L-lysine	HMDB
Nalpha-(gamma-aminobutyryl)lysine	HMDB
6-Amino-2-[(4-amino-1-hydroxybutylidene)amino]hexanoate	HMDB

Chemical Formula

C₁₀H₂₁N₃O₃

Average Molecular Weight

231.292

Monoisotopic Molecular Weight

231.158291553

IUPAC Name

6-amino-2-(4-aminobutanamido)hexanoic acid

Traditional Name

6-amino-2-(4-aminobutanamido)hexanoic acid

CAS Registry Number

22468-02-6

SMILES

NCCCCC(NC(=O)CCCN)C(O)=O

InChI Identifier

InChI=1S/C10H21N3O3/c11-6-2-1-4-8(10(15)16)13-9(14)5-3-7-12/h8H,1-7,11-12H2,(H,13,14)(H,15,16)

InChI Key

OCBQYJFUZHJRIU-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hybrid peptides. Hybrid peptides are compounds containing at least two different types of amino acids (alpha, beta, gamma, delta) linked to each other through a peptide bond.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Peptidomimetics

Sub Class

Hybrid peptides

Direct Parent

Hybrid peptides

Alternative Parents

Substituents

Hybrid peptide
N-acyl-alpha-amino acid
N-acyl-alpha amino acid or derivatives
Gamma amino acid or derivatives
Alpha-amino acid or derivatives
Medium-chain fatty acid
Amino fatty acid
Fatty amide
N-acyl-amine
Fatty acyl
Fatty acid
Amino acid or derivatives
Secondary carboxylic acid amide
Carboxamide group
Amino acid
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Carboxylic acid
Organooxygen compound
Organic oxide
Organopnictogen compound
Primary aliphatic amine
Organic nitrogen compound
Hydrocarbon derivative
Carbonyl group
Organic oxygen compound
Primary amine
Organonitrogen compound
Amine
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Brain (HMDB: HMDB0001959)

Non-excretory biofluid

Biofluid or Excreta

Cerebrospinal Fluid (CSF) (HMDB: HMDB0001959)
Cerebrospinal fluid (HMDB: HMDB0001959)

Source

Endogenous

Endogenous (HMDB: HMDB0001959)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	12.9 g/L	ALOGPS
logP	-3.3	ALOGPS
logP	-3.8	ChemAxon
logS	-1.2	ALOGPS
pKa (Strongest Acidic)	3.91	ChemAxon
pKa (Strongest Basic)	10.41	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	118.44 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	60.07 m³·mol⁻¹	ChemAxon
Polarizability	25.48 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0001959

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022766

KNApSAcK ID

Not Available

Chemspider ID

16267810

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

6403

PubChem Compound

23208897

PDB ID

Not Available

ChEBI ID

89308

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for gamma-Aminobutyryllysine (CFc000001309)

MOL for CFc000001309 (gamma-Aminobutyryllysine)

3D MOL for CFc000001309 (gamma-Aminobutyryllysine)

3D SDF for CFc000001309 (gamma-Aminobutyryllysine)

3D-SDF for CFc000001309 (gamma-Aminobutyryllysine)

PDB for CFc000001309 (gamma-Aminobutyryllysine)

3D PDB for CFc000001309 (gamma-Aminobutyryllysine)

SMILES for CFc000001309 (gamma-Aminobutyryllysine)

INCHI for CFc000001309 (gamma-Aminobutyryllysine)

Structure for CFc000001309 (gamma-Aminobutyryllysine)

3D Structure for CFc000001309 (gamma-Aminobutyryllysine)