ChemFOnt: Showing chemical card for 4-Trimethylammoniobutanoic acid (CFc000000899)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:45:25 UTC

Chemfont ID

CFc000000899

Molecule Identification

Common Name

4-Trimethylammoniobutanoic acid

Definition

4-Trimethylammoniobutanoic acid, also known as gamma-butyrobetaine (GBB) or 3-dehydroxycarnitine, is a highly water-soluble derivative of gamma-aminobutyric acid (GABA). It is also a precursor of L-carnitine. It is a substrate of gamma butyrobetaine hydroxylase/dioxygenase (also known as BBOX) which catalyzes the formation of L-carnitine from gamma-butyrobetaine, the last step in the L-carnitine biosynthesis pathway. Carnitine is essential for the transport of activated fatty acids across the mitochondrial membrane during mitochondrial beta-oxidation. Numerous disorders have been described that lead to disturbances in energy production and in intermediary metabolism which are characterized by the production and excretion of unusual acylcarnitines. A mutation in the gene coding for carnitine-acylcarnitine translocase, or the OCTN2 transporter aetiologically, causes a carnitine deficiency that results in poor intestinal absorption of dietary L-carnitine, impaired reabsorption by the kidney, and increased urinary loss. Determination of the qualitative pattern of acylcarnitines can be of diagnostic and therapeutic importance. The betaine structure of carnitine requires special analytical procedures for recording. The ionic nature of L-carnitine causes a high water solubility which decreases with increasing chain length of the ester group in the acylcarnitines. Therefore, the distribution of L-carnitine and acylcarnitines in various organs is defined by their function and their physicochemical properties as well. High-performance liquid chromatography (HPLC) permits screening for free and total carnitine, as well as complete quantitative acylcarnitine determination, including the long-chain acylcarnitine profile (PMID: 17508264 , Monatshefte fuer Chemie (2005), 136(8), 1279-1291., Int J Mass Spectrom. 1999;188:39-52.).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
4-Trimethylammoniobutanoate	ChEBI
Butyrobetaine	ChEBI
gamma-Butyrobetaine	ChEBI
Butyro-betaine	Kegg
g-Butyrobetaine	Generator
Γ-butyrobetaine	Generator
Deoxy-carnitine	MeSH
Deoxycarnitine	MeSH
4-N-Trimethylammonium butyrate	MeSH
4-Trimethylaminobutyrate	MeSH
4-(N-trimethylamino)Butyrate	HMDB
4-Butyrobetaine	HMDB
Actinine	HMDB

Chemical Formula

C₇H₁₆NO₂

Average Molecular Weight

146.2074

Monoisotopic Molecular Weight

146.118103761

IUPAC Name

(3-carboxypropyl)trimethylazanium

Traditional Name

4-trimethylaminobutyrate

CAS Registry Number

407-64-7

SMILES

C[N+](C)(C)CCCC(O)=O

InChI Identifier

InChI=1S/C7H15NO2/c1-8(2,3)6-4-5-7(9)10/h4-6H2,1-3H3/p+1

InChI Key

JHPNVNIEXXLNTR-UHFFFAOYSA-O

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
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxide
Amine
Hydrocarbon derivative
Organic salt
Organic nitrogen compound
Organooxygen compound
Organonitrogen compound
Carbonyl group
Organopnictogen compound
Organic oxygen compound
Organic cation
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

quaternary ammonium ion (CHEBI:1941 )

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 15164354)
Saliva (PMID: 22308371)

Organ

Excreta

Biofluid or Excreta

Urine (PMID: 32966057)
Feces (PMID: 24628373)

Cellular substructure

Source

Endogenous

Endogenous (HMDB: HMDB0001161)

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Carnitine Synthesis (PathBank: SMP0087187)

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.33 g/L	ALOGPS
logP	-3	ALOGPS
logP	-4	ChemAxon
logS	-2.7	ALOGPS
pKa (Strongest Acidic)	4.46	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	37.3 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	51.44 m³·mol⁻¹	ChemAxon
Polarizability	16.63 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022456

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

C01181

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

134

PDB ID

Not Available

ChEBI ID

1941

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Kawamura, Masao; Akutsu, Seiichi; Fukuda, Hirosuke; Hata, Hiroyuki; Morishita, Tsuyoshi; Kano, Kenji; Nishimori, Hirokuni. Manufacture of g-butyrobetaine by fermentation. Jpn. Kokai Tokkyo Koho (1987), 6 pp.

Showing chemical card for 4-Trimethylammoniobutanoic acid (CFc000000899)

MOL for CFc000000899 (4-Trimethylammoniobutanoic acid)

3D MOL for CFc000000899 (4-Trimethylammoniobutanoic acid)

3D SDF for CFc000000899 (4-Trimethylammoniobutanoic acid)

3D-SDF for CFc000000899 (4-Trimethylammoniobutanoic acid)

PDB for CFc000000899 (4-Trimethylammoniobutanoic acid)

3D PDB for CFc000000899 (4-Trimethylammoniobutanoic acid)

SMILES for CFc000000899 (4-Trimethylammoniobutanoic acid)

INCHI for CFc000000899 (4-Trimethylammoniobutanoic acid)

Structure for CFc000000899 (4-Trimethylammoniobutanoic acid)

3D Structure for CFc000000899 (4-Trimethylammoniobutanoic acid)