gamma-Butyrobetaine (ECMDB21336) (M2MDB001736)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes (1)Transporters (5)XML
Proteins (622)
Record Information
Version2.0
Creation Date2012-07-30 14:55:21 -0600
Update Date2015-06-03 17:21:11 -0600
Secondary Accession Numbers
  • ECMDB21336
Identification
Name:gamma-Butyrobetaine
Description4-Trimethylammoniobutanoic acid is an intermediate in carnitine biosynthesis. It is part of a reaction in which 4-trimethylammoniobutanal is oxidized by the 4-trimethylaminobutyraldehyde dehydrogenase protein to 4-trimethylammoniobutanoic acid. 4-trimethylammoniobutanoic acid is transformed into L-carnitine via the enzyme gamma-butyrobetaine dioxygenase.It is a substrate for Gamma-butyrobetaine dioxygenase, Aldehyde dehydrogenase and 4-trimethylaminobutyraldehyde dehydrogenase.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms:
  • 3-Carboxypropyl-trimethyl-ammonium
  • 4-(N-Trimethylamino)butyrate
  • 4-(N-Trimethylamino)butyric acid
  • 4-(Trimethylammonio)butanoate
  • 4-(Trimethylammonio)butanoic acid
  • 4-Butyrobetaine
  • 4-Trimethylammoniobutanoate
  • 4-Trimethylammoniobutanoic acid
  • Actinine
  • Butyrobetaine
  • Deoxycarnitine
  • g-Butyrobetain
  • g-Butyrobetaine
  • Gamma-Butyrobetain
  • Gamma-Butyrobetaine
  • γ-Butyrobetain
  • γ-Butyrobetaine
Chemical Formula:C7H15NO2
Weight:Average: 145.1995
Monoisotopic: 145.110278729
InChI Key:JHPNVNIEXXLNTR-UHFFFAOYSA-N
InChI:InChI=1S/C7H15NO2/c1-8(2,3)6-4-5-7(9)10/h4-6H2,1-3H3
CAS number:407-64-7
IUPAC Name:4-(trimethylazaniumyl)butanoate
Traditional IUPAC Name:butyrobetaine
SMILES:C[N+](C)(C)CCCC([O-])=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.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentStraight 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
  • Organic oxide
  • Amine
  • Hydrocarbon derivative
  • Organic salt
  • Organic nitrogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Organopnictogen compound
  • Organic oxygen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
State:Solid
Charge:0
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility0.23 g/LALOGPS
logP-3.1ALOGPS
logP-4ChemAxon
logS-3ALOGPS
pKa (Strongest Acidic)4.46ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area40.13 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity62.28 m³·mol⁻¹ChemAxon
Polarizability16.2 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
gamma-Butyrobetainyl-CoA + Carnitine <> L-Carnitinyl-CoA + gamma-Butyrobetaine
Carnitine + gamma-Butyrobetainyl-CoA > L-Carnitinyl-CoA + gamma-Butyrobetaine
(E)-4-(Trimethylammonio)but-2-enoyl-CoA + L-Carnitine + 4-Trimethylammoniobutanoyl-CoA <> Crotonobetaine + L-Carnitinyl-CoA + gamma-Butyrobetaine
gamma-Butyrobetainyl-CoA + L-Carnitine > D-Carnitinyl-CoA + gamma-Butyrobetaine
SMPDB Pathways:
L-carnitine degradation IPW002037 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:Not Available
EcoCyc Pathways:
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00di-9200000000-db9c27544fc4b78a3ffdView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0002-0900000000-859205a790bddd439909View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-000j-9500000000-2244afa7512434be351dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-000i-9000000000-2c1f817b20a8cbfba00cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0006-9000000000-8c578b9dc166594a66beView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-052e-9000000000-d1e5ff8334122de266a6View in MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-000b-7900000000-ff7cb6ee0c5eec3fb812View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-052e-9000000000-b4529cb8b31f26a2dc2aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0002-7900000000-990405988c934085cb3eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-000i-9000000000-fa893a46940a677ca884View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-000b-7900000000-f5baf5443f2ac35b9088View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-000i-9000000000-ceba93a4d1a8d5a35869View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-000b-9600000000-bc556243eb365d64176fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-0002-5900000000-a1e724e53532d74ba5e7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-000b-7900000000-c53120e4be9dd4abc3d7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-0a4m-9300000000-0f1930134b0fc7910e12View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-001l-9000000000-73f9fa300c0d7955628bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-000m-9000000000-4f9fc35eb01531740b85View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-0005-9000000000-916262ee1da6f50e2502View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-0006-2900000000-0e3fd42c5d0320b3892cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0f92-0900000000-543e3ddd695c95c84efdView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0uds-6900000000-2935d3993a057a2a7fddView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9100000000-1c7e8f5838068bd092fbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-1900000000-f4142ed02e4763e04740View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-5900000000-74df013a2a0033b163e1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0kg6-9000000000-eb91f7fa144cb7eb7e80View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
References
References:
  • Canovas, M., Bernal, V., Sevilla, A., Iborra, J. L. (2007). "Salt stress effects on the central and carnitine metabolisms of Escherichia coli." Biotechnol Bioeng 96:722-737. Pubmed: 16894634
  • Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
  • Pierre G, Macdonald A, Gray G, Hendriksz C, Preece MA, Chakrapani A: Prospective treatment in carnitine-acylcarnitine translocase deficiency. J Inherit Metab Dis. 2007 Oct;30(5):815. Epub 2007 May 12. Pubmed: 17508264
  • van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195
  • Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. Pubmed: 18331064
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID16244
HMDB IDHMDB01161
Pubchem Compound ID725
Kegg IDC01181
ChemSpider ID705
Wikipedia IDNot Available
BioCyc IDGAMMA-BUTYROBETAINE
EcoCyc IDGAMMA-BUTYROBETAINE

Enzymes

Protein Details
1. Crotonobetainyl-CoA:carnitine CoA-transferase
General function:
Involved in catalytic activity
Specific function:
Catalyzes the reversible transfer of the CoA moiety from gamma-butyrobetainyl-CoA to L-carnitine to generate L-carnitinyl- CoA and gamma-butyrobetaine. Is also able to catalyze the reversible transfer of the CoA moiety from gamma-butyrobetainyl- CoA or L-carnitinyl-CoA to crotonobetaine to generate crotonobetainyl-CoA
Gene Name:
caiB
Uniprot ID:
P31572
Molecular weight:
45126

Transporters

Protein Details
1. Outer membrane protein N
General function:
Involved in transporter activity
Specific function:
Non-specific porin
Gene Name:
ompN
Uniprot ID:
P77747
Molecular weight:
41220
Protein Details
2. Outer membrane pore protein E
General function:
Involved in transporter activity
Specific function:
Uptake of inorganic phosphate, phosphorylated compounds, and some other negatively charged solutes
Gene Name:
phoE
Uniprot ID:
P02932
Molecular weight:
38922
Protein Details
3. L-carnitine/gamma-butyrobetaine antiporter
General function:
Involved in transporter activity
Specific function:
Catalyzes the exchange of L-carnitine for gamma- butyrobetaine and related betaines
Gene Name:
caiT
Uniprot ID:
P31553
Molecular weight:
56587
Protein Details
4. Outer membrane protein F
General function:
Involved in transporter activity
Specific function:
OmpF is a porin that forms passive diffusion pores which allow small molecular weight hydrophilic materials across the outer membrane. It is also a receptor for the bacteriophage T2
Gene Name:
ompF
Uniprot ID:
P02931
Molecular weight:
39333
Protein Details
5. Outer membrane protein C
General function:
Involved in transporter activity
Specific function:
Forms passive diffusion pores which allow small molecular weight hydrophilic materials across the outer membrane
Gene Name:
ompC
Uniprot ID:
P06996
Molecular weight:
40368