Crotonobetaine (ECMDB21321) (M2MDB001723)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes (5)Transporters (2)XML
Proteins (13)
Record Information
Version2.0
Creation Date2012-07-30 14:55:18 -0600
Update Date2015-06-03 17:21:09 -0600
Secondary Accession Numbers
  • ECMDB21321
Identification
Name:Crotonobetaine
DescriptionCrotonobetaine is a member of the chemical class known as Quaternary Ammonium Salts. These are compounds containing positively charged polyatomic ion of the structure NR4+, R being an alkyl group or an aryl groupCrotonobetaine is invovled in Carnitine metabolism, and ABC transporters. Crotonobetaine is involved in carnitine metabolism. Carnitine dehydratase from Escherichia coli O44 K74 is an inducible enzyme detectable in cells grown anaerobically in the presence of L-(-)-carnitine or crotonobetaine. (PMID 8188598).
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms:
  • (2E)-4-(trimethylammonio)but-2-enoate
  • (2E)-4-(trimethylammonio)but-2-enoic acid
  • (3-carboxyallyl)trimethylammonium hydroxide, inner salt
  • 4-(Trimethylammonio)but-2-enoate
  • 4-(Trimethylammonio)but-2-enoic acid
  • Croton betaine
  • Crotonate betaine
  • Crotonic acid betaine
  • Crotono-betaine
  • Crotonobetaine
  • Crotonsaurebetain
Chemical Formula:C7H13NO2
Weight:Average: 143.1836
Monoisotopic: 143.094628665
InChI Key:GUYHPGUANSLONG-SNAWJCMRSA-N
InChI:InChI=1S/C7H13NO2/c1-8(2,3)6-4-5-7(9)10/h4-5H,6H2,1-3H3/b5-4+
CAS number:927-89-9
IUPAC Name:(2E)-4-(trimethylazaniumyl)but-2-enoate
Traditional IUPAC Name:crotonobetaine
SMILES:[H]\C(=C(\[H])C([H])([H])[N+](C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H])C([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
  • Unsaturated fatty acid
  • Quaternary ammonium salt
  • Tetraalkylammonium salt
  • Carboxylic acid salt
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organic salt
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Amine
  • Organic oxide
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
State:Not Available
Charge:0
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility0.087 g/LALOGPS
logP-2.8ALOGPS
logP-3.8ChemAxon
logS-3.4ALOGPS
pKa (Strongest Acidic)4.49ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area40.13 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity63.22 m³·mol⁻¹ChemAxon
Polarizability15.56 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
Adenosine triphosphate + Water + Crotonobetaine > ADP + Crotonobetaine + Hydrogen ion + Phosphate
Adenosine triphosphate + Water + Crotonobetaine > ADP + Crotonobetaine + Hydrogen ion + Phosphate
Adenosine triphosphate + Coenzyme A + Crotonobetaine > ADP + Crotonobetainyl-CoA + Phosphate
Carnitine + Crotonobetainyl-CoA <> L-Carnitinyl-CoA + Crotonobetaine
(E)-4-(Trimethylammonio)but-2-enoyl-CoA + L-Carnitine + 4-Trimethylammoniobutanoyl-CoA <> Crotonobetaine + L-Carnitinyl-CoA + gamma-Butyrobetaine
SMPDB Pathways:Not Available
KEGG Pathways:Not Available
EcoCyc Pathways:Not Available
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-002g-4900000000-c8b03fae018b169a2e01View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-002e-9800000000-ccc6940cd5c2b86b325fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000m-9000000000-79a28749b01de1e2632fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-1900000000-f5fdddf4dc2a31fd3ddcView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-5900000000-bc7d04ce2d48f7eb839dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05n0-9000000000-51e7dcf4e8df7057eca3View in MoNA
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
1D NMR1H 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
  • 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 ID17237
HMDB IDNot Available
Pubchem Compound ID5462194
Kegg IDC04114
ChemSpider ID4575319
Wikipedia IDNot Available
BioCyc IDCROTONO-BETAINE
EcoCyc IDCROTONO-BETAINE

Enzymes

Protein Details
1. Glycine betaine/L-proline transport ATP-binding protein proV
General function:
Involved in nucleotide binding
Specific function:
Involved in a multicomponent binding-protein-dependent transport system for glycine betaine/L-proline
Gene Name:
proV
Uniprot ID:
P14175
Molecular weight:
44162
Protein Details
2. 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
Protein Details
3. Glycine betaine/L-proline transport system permease protein proW
General function:
Involved in transporter activity
Specific function:
Involved in a multicomponent binding-protein-dependent transport system for glycine betaine/L-proline
Gene Name:
proW
Uniprot ID:
P14176
Molecular weight:
37619
Protein Details
4. Probable crotonobetaine/carnitine-CoA ligase
General function:
Involved in catalytic activity
Specific function:
Could catalyze the transfer of CoA to carnitine, generating the initial carnitinyl-CoA needed for the CaiB reaction cycle
Gene Name:
caiC
Uniprot ID:
P31552
Molecular weight:
58559
Protein Details
5. Glycine betaine-binding periplasmic protein
General function:
Involved in transporter activity
Specific function:
Member of a multicomponent binding-protein-dependent transport system (the proU transporter) which serves as the glycine betaine/L-proline transporter
Gene Name:
proX
Uniprot ID:
P0AFM2
Molecular weight:
36022

Transporters

Protein Details
1. Proline/betaine transporter
General function:
Involved in transporter activity
Specific function:
Proton symporter that senses osmotic shifts and responds by importing osmolytes such as proline, glycine betaine, stachydrine, pipecolic acid, ectoine and taurine. It is both an osmosensor and an osmoregulator which is available to participate early in the bacterial osmoregulatory response
Gene Name:
proP
Uniprot ID:
P0C0L7
Molecular weight:
54845
Protein Details
2. Glycine betaine/L-proline transport system permease protein proW
General function:
Involved in transporter activity
Specific function:
Involved in a multicomponent binding-protein-dependent transport system for glycine betaine/L-proline
Gene Name:
proW
Uniprot ID:
P14176
Molecular weight:
37619