ChemFOnt: Showing chemical card for 5-amino valeric acid betaine (CFc000220985)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-14 01:40:30 UTC

Chemfont ID

CFc000220985

Molecule Identification

Common Name

5-amino valeric acid betaine

Definition

5-amino valeric acid betaine (5-AVAB), also known as delta-valerobetaine and δ-valerobetaine, belongs to the class of organic compounds known as straight chain fatty acids. These are fatty acids with a straight aliphatic chain. 5-AVAB is also classified as a betaine. Betaines are neutral chemical compounds with a positively charged cationic functional group, such as a quaternary ammonium or phosphonium cation. 5-AVAB is a weakly acidic compound (based on its pKa). There is considerable confusion over the nomenclature of this molecule, with widely varying synonyms appearing in databases and the literature (PMID: 30158657 ). 5-AVAB is sometimes (incorrectly) referred to as simply “aminovaleric acid betaine” or “trimethylaminovaleric acid” or TMAVA. The fact that there is a known, unnatural isomer (4-amino valeric acid betaine) requires that the position of the betaine/acidic group be properly identified. 5-AVAB has also been called 5-trimethylaminovaleric acid (PMID: 921982 ) and 5-[trimethylammonio]pentanoate (PMID: 24571165 ) in earlier literature. 5-AVAB is associated with the consumption of foods or diets that are rich in whole grains and vegetables (PMID: 30158657 ). 5-AVAB is a gut microbial metabolite that arises from the breakdown of trimethyllysine (PMID: 35365608 ). Trimethyllysine is particularly abundant in vegetables and grains as a free amino acid (PMID: 24454731 ), although it may also be derived from the endogenous breakdown of proteins in the body during starvation or fasting (PMID: 24454731 ). 5-AVAB tends to accumulate in metabolically active tissues including the heart, muscle and brown adipose tissue (PMID: 30158657 ). 5-AVAB has similar molecular structure with meldonium (mildronate), a drug that inhibits β-oxidation of fatty acids (PMID: 30158657 ). Meldonium has been associated with improved cardiac mitochondrial function after ischemia and is considered a potential performance enhancing drug (PMID: 27465696 ). Meldonium has been shown to have beneficial effects in cardiovascular, neurological and metabolic diseases due to its anti-ischaemic and cardioprotective properties, which are ascribed mainly to its inhibition of β-oxidation and its activation of glycolysis. Among athletes, meldonium is used with the purpose of increasing recovery rate or exercise performance (PMID: 27465696 ). In particular, meldonium protects cardiac mtDNA from oxidative stress during exhaustive exercise (PMID: 33930377 ). Like meldonium, 5-AVAB appears to block the cell membrane carnitine transporter (OCTN2) and reduces biosynthesis of L-carnitine from γ-butyrobetaine by inhibiting γ-butyrobetaine hydroxylase (PMID: 30158657 ). This leads to reduced β-oxidation of fatty acids. For healthy individuals, 5-AVAB may provide a beneficial effect with improved cardiac metabolism and improved recovery from physical exercise. However, its effect may be deleterious for individuals with heart disease. In particular, 5-AVAB has been found to be elevated in patients with heart failure and its levels correlate with an increased risk of cardiac mortality and heart transplantation in patients with heart failure (PMID: 35365608 ). Furthermore, 5-AVAB treatment has been shown to aggravate cardiac hypertrophy and dysfunction in high-fat diet-fed mice (PMID: 35365608 ). Overall, 5-AVAB decreases fatty acid oxidation (FAO). FAO is a hallmark of metabolic reprogramming in the diseased heart and contributes to impaired myocardial energetics and contractile dysfunction. A contrarian view of the associative effects of 5-AVAB and heart disease is that 5-AVAB accumulates in heart tissues in diseased individuals as a protective chemical. The more diseased the heart, the more 5-AVAB is generated to stave off mitochondrial collapse in the heart tissue. Clearly more research on the cause and effects of 5-AVAB is needed.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Δ-valerobetaine	Generator
5-aminovaleric acid betaine	HMDB
N-trimethyl-5-aminovalerate	HMDB
5-trimethylaminovalerate	HMDB
N,N,N-trimethyl-5-aminovaleric acid	HMDB
N,N,N-trimethyl-5-aminovalerate	HMDB
X-21365	HMDB
5-AVAB	HMDB
ΔVB	HMDB
GBB-5	HMDB
TMAVA	HMDB
TMAV	HMDB

Chemical Formula

C₈H₁₇NO₂

Average Molecular Weight

159.229

Monoisotopic Molecular Weight

159.125928791

IUPAC Name

5-(trimethylazaniumyl)pentanoate

Traditional Name

5-(trimethylammonio)pentanoate

CAS Registry Number

Not Available

SMILES

C[N+](C)(C)CCCCC([O-])=O

InChI Identifier

InChI=1S/C8H17NO2/c1-9(2,3)7-5-4-6-8(10)11/h4-7H2,1-3H3

InChI Key

CDLVFVFTRQPQFU-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as straight chain fatty acids. These are fatty acids with a straight aliphatic chain.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acids and conjugates

Direct Parent

Straight chain fatty acids

Alternative Parents

Substituents

Straight chain fatty acid
Quaternary ammonium salt
Tetraalkylammonium salt
Carboxylic acid salt
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Hydrocarbon derivative
Organic salt
Organic oxygen compound
Organic nitrogen compound
Organooxygen compound
Organonitrogen compound
Carbonyl group
Amine
Organic oxide
Organic cation
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 32966057)

Excreta

Biofluid or Excreta

Urine (PMID: 32966057)

Source

Exogenous

Exogenous (HMDB: HMDB0240732)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.1 g/L	ALOGPS
logP	-3.1	ALOGPS
logP	-3.5	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	4.56	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	40.13 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	66.88 m³·mol⁻¹	ChemAxon
Polarizability	18.28 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

HMDB0240732

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

34236878

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

14274897

PDB ID

Not Available

ChEBI ID

145234

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for 5-amino valeric acid betaine (CFc000220985)

MOL for CFc000220985 (5-amino valeric acid betaine)

3D MOL for CFc000220985 (5-amino valeric acid betaine)

3D SDF for CFc000220985 (5-amino valeric acid betaine)

3D-SDF for CFc000220985 (5-amino valeric acid betaine)

PDB for CFc000220985 (5-amino valeric acid betaine)

3D PDB for CFc000220985 (5-amino valeric acid betaine)

SMILES for CFc000220985 (5-amino valeric acid betaine)

INCHI for CFc000220985 (5-amino valeric acid betaine)

Structure for CFc000220985 (5-amino valeric acid betaine)

3D Structure for CFc000220985 (5-amino valeric acid betaine)