Page last updated: 2024-12-04

gamma-butyrobetaine

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

4-(trimethylammonio)butanoate : An amino-acid betaine gamma-aminobutyric acid zwitterion in which all of the hydrogens attached to the nitrogen are replaced by methyl groups. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Cross-References

ID SourceID
PubMed CID725
CHEMBL ID2074645
CHEBI ID16244
SCHEMBL ID233637
MeSH IDM0043699

Synonyms (40)

Synonym
4-trimethylammoniobutanoic acid
ammonium, (3-carboxypropyl)trimethyl-, hydroxide, inner salt
gamma-butyrobetain [german]
n-trimethyl-gamma-aminobutyric acid
1-propanaminium, 3-carboxy-n,n,n-trimethyl-, hydroxide, inner salt
3-carboxy-n,n,n-trimethyl-1-propanaminium hydroxide inner salt
butyrobetaine
gamma-butyrobetain
407-64-7
3-dehydroxycarnitine
CHEBI:16244 ,
4-(n-trimethylamino)butyrate
deoxycarnitine
4-(trimethylammonio)butanoate
4-butyrobetaine
actinine
4-(trimethylamino)butanoate
GAMMA-BUTYROBETAINE ,
4-(trimethylazaniumyl)butanoate
hd7gi3hy9q ,
unii-hd7gi3hy9q
CHEMBL2074645
gtpl6605
4-trimethylazaniumylbutanoate
SCHEMBL233637
AKOS025295305
2WSX
STL453117
gamma butyrobetaine
JHPNVNIEXXLNTR-UHFFFAOYSA-N
gbb
gamma-butyrobetaine [who-dd]
Q27073962
butyrobetaine;4-trimethylammoniobutanoic acid;gamma-butyrobetaine;3-carboxylato-n pound notn pound notn-trimethyl-1-propanaminium;(4-hydroxy-4-oxobutyl)-trimethylazanium
BCP29262
gamma-butyrobetaine;deoxycarnitine
DTXSID00961102
-butyrobetaine;deoxycarnitine
1-propanaminium, 3-carboxy-n,n,n-trimethyl-, hydroxide, inner salt (9ci)
PD048099

Research Excerpts

Compound-Compound Interactions

ExcerptReferenceRelevance
"A novel aqueous solvent-based dispersive liquid-liquid microextraction (AS-DLLME) method was combined with narrow-bore liquid chromatography and fluorescence detection for the determination of hydrophilic compounds."( Fluorescent derivatization combined with aqueous solvent-based dispersive liquid-liquid microextraction for determination of butyrobetaine, l-carnitine and acetyl-l-carnitine in human plasma.
Chen, YC; Feng, CH; Tsai, CJ, 2016
)
0.43

Bioavailability

ExcerptReferenceRelevance
" Carnitine supplementation of AA-MFs shows reduced bioavailability due, in part, to bacterial degradation to TMAO, whereas the bioavailability of carnitine is greater with prebiotic GMP-MFs."( Metabolomic Markers of Essential Fatty Acids, Carnitine, and Cholesterol Metabolism in Adults and Adolescents with Phenylketonuria.
Broniowska, K; Levy, HL; Murali, SG; Nair, N; Ney, DM; Rohr, F; Stroup, BM, 2018
)
0.48

Dosage Studied

ExcerptRelevanceReference
"Mildronate was administered perorally, at a dosage of 500mg, twice daily."( Mildronate treatment alters γ-butyrobetaine and l-carnitine concentrations in healthy volunteers.
Dambrova, M; Grinberga, S; Kalvinsh, I; Konrade, I; Kuka, J; Liepinsh, E; Pugovics, O; Skapare, E, 2011
)
0.37
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (2)

RoleDescription
human metaboliteAny mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens).
Escherichia coli metaboliteAny bacterial metabolite produced during a metabolic reaction in Escherichia coli.
[role information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Drug Classes (1)

ClassDescription
amino-acid betaineAny amino acid-derived zwitterion - such as glycine betaine (N,N,N-trimethylammonioacetate) - in which the ammonium nitrogen carries methyl substituents and bears no hydrogen atoms.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Pathways (9)

PathwayProteinsCompounds
Metabolism14961108
Amino acid and derivative metabolism250260
Carnitine synthesis416
L-Carnitine Degradation I410
L-carnitine biosynthesis014
Renz2020 - GEM of Human alveolar macrophage with SARS-CoV-20490
Diet-dependent trimethylamine/trimethylamine N-oxide metabolism112
u03B3-butyrobetaine degradation123
L-carnitine degradation I417
L-carnitine biosynthesis623
carnitine degradation I210

Bioassays (10)

Assay IDTitleYearJournalArticle
AID680966TP_TRANSPORTER: inhibition of carnitine transport by gamma-butyrobetaine at 5uM in Octn3-HEK cells2000The Journal of biological chemistry, Dec-22, Volume: 275, Issue:51
Molecular and functional characterization of organic cation/carnitine transporter family in mice.
AID1865537Binding affinity to human recombinant MBP-TMLD (42 to 421 residues) fusion protein expressed in Escherichia coli BL21-AI assessed as change in enthalpy by isothermal titration calorimetry2022ACS medicinal chemistry letters, Nov-10, Volume: 13, Issue:11
Binding versus Enzymatic Processing of ε-Trimethyllysine Dioxygenase Substrate Analogues.
AID1865535Binding affinity to human recombinant MBP-TMLD (42 to 421 residues) fusion protein expressed in Escherichia coli BL21-AI by isothermal titration calorimetry2022ACS medicinal chemistry letters, Nov-10, Volume: 13, Issue:11
Binding versus Enzymatic Processing of ε-Trimethyllysine Dioxygenase Substrate Analogues.
AID1865536Binding affinity to human recombinant MBP-TMLD (42 to 421 residues) fusion protein expressed in Escherichia coli BL21-AI assessed as change in Gibbs free energy by isothermal titration calorimetry2022ACS medicinal chemistry letters, Nov-10, Volume: 13, Issue:11
Binding versus Enzymatic Processing of ε-Trimethyllysine Dioxygenase Substrate Analogues.
AID687626Activity of commercial yeast alpha-glucosidase assessed as production of p-nitrophenol using p-nitrophenyl-alpha-D-glucopyranoside as substrate at 50 mM after 3 mins by spectrophotometer2011Bioorganic & medicinal chemistry, May-15, Volume: 19, Issue:10
Cellular zwitterionic metabolite analogs simultaneously enhance reaction rate, thermostability, salt tolerance, and substrate specificity of α-glucosidase.
AID1865538Binding affinity to human recombinant MBP-TMLD (42 to 421 residues) fusion protein expressed in Escherichia coli BL21-AI assessed as change in entropy by isothermal titration calorimetry2022ACS medicinal chemistry letters, Nov-10, Volume: 13, Issue:11
Binding versus Enzymatic Processing of ε-Trimethyllysine Dioxygenase Substrate Analogues.
AID687625Activity of Saccharomyces cerevisiae alpha-glucosidase assessed as production of p-nitrophenol using p-nitrophenyl-alpha-D-glucopyranoside as substrate at 50 mM after 3 mins by spectrophotometer2011Bioorganic & medicinal chemistry, May-15, Volume: 19, Issue:10
Cellular zwitterionic metabolite analogs simultaneously enhance reaction rate, thermostability, salt tolerance, and substrate specificity of α-glucosidase.
AID687624Activity of Bacillus stearothermophilus alpha-glucosidase assessed as production of p-nitrophenol using p-nitrophenyl-alpha-D-glucopyranoside as substrate at 50 mM after 3 mins by spectrophotometer2011Bioorganic & medicinal chemistry, May-15, Volume: 19, Issue:10
Cellular zwitterionic metabolite analogs simultaneously enhance reaction rate, thermostability, salt tolerance, and substrate specificity of α-glucosidase.
AID1865552Substrate activity at human recombinant MBP-TMLD (42 to 421 residues) fusion protein expressed in Escherichia coli BL21-AI assessed as hydroxylated substrate formation at 500 uM in presence of alpha-ketoglutarate by proton 1D NMR spectroscopy2022ACS medicinal chemistry letters, Nov-10, Volume: 13, Issue:11
Binding versus Enzymatic Processing of ε-Trimethyllysine Dioxygenase Substrate Analogues.
AID680373TP_TRANSPORTER: inhibition of carnitine uptake by gamma-butyrobetaine at 5uM in Octn2-HEK cells2000The Journal of biological chemistry, Dec-22, Volume: 275, Issue:51
Molecular and functional characterization of organic cation/carnitine transporter family in mice.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (152)

TimeframeStudies, This Drug (%)All Drugs %
pre-199042 (27.63)18.7374
1990's23 (15.13)18.2507
2000's36 (23.68)29.6817
2010's41 (26.97)24.3611
2020's10 (6.58)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 31.72

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be moderate demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index31.72 (24.57)
Research Supply Index5.11 (2.92)
Research Growth Index4.60 (4.65)
Search Engine Demand Index61.83 (26.88)
Search Engine Supply Index2.93 (0.95)

This Compound (31.72)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials5 (3.13%)5.53%
Reviews2 (1.25%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other153 (95.63%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]