P. aeruginosa Metabolome Database: Crotonobetaine (PAMDB001723)

Identification Taxonomy Physical Properties Biological Properties Spectra Concentrations Links References Enzymes Transporters

Proteins (3280)

Record Information

Version

1.0

Update Date

1/22/2018 12:54:54 PM

Metabolite ID

PAMDB001723

Identification

Name:

Crotonobetaine

Description:

Crotonobetaine 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 Pseudomonas aeruginosa O44 K74 is an inducible enzyme detectable in cells grown anaerobically in the presence of L-(-)-carnitine or crotonobetaine. (PMID 8188598).

Structure

🔍MOL SDF PDB SMILES InChI View Structure

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

Average Molecular Weight:

143.1836

Monoisotopic Molecular Weight:

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

Taxonomy Description

This compound 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

Unsaturated fatty acid
Straight chain fatty acid
Quaternary ammonium salt
Carboxylic acid salt
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Hydrocarbon derivative
Organic salt
Organooxygen compound
Organonitrogen compound
Carbonyl group
Amine
Organic zwitterion
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

4-(trimethylammonio)but-2-enoate (CHEBI:17237 )

Physical Properties

State:

Not Available

Charge:

Melting point:

Not Available

Experimental Properties:

Property	Value	Source

Predicted Properties

Property	Value	Source
Water Solubility	0.0869 mg/mL	ALOGPS
logP	-2.8	ALOGPS
logP	-3.8	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	4.49	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	3	ChemAxon
Refractivity	63.22 m³·mol^-1	ChemAxon
Polarizability	15.56 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

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

Pathways:

Not Available

Spectra

Spectra:

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

Links

External Links:

Resource	Link
CHEBI ID	17237
HMDB ID	Not Available
Pubchem Compound ID	5462194
Kegg ID	C04114
ChemSpider ID	4575319
Wikipedia ID	Not Available
BioCyc ID	CROTONO-BETAINE
EcoCyc ID	CROTONO-BETAINE

Enzymes

Protein Details

• 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
Locus Tag:: PA5094
Molecular weight:: 30.7 kDa

Crotonobetaine (PAMDB001723)

Structure for Crotonobetaine (PAMDB001723)

Enzymes

Transporters