P. aeruginosa Metabolome Database: Carnitine (PAMDB000023)

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

Proteins (3280)

Record Information

Version

1.0

Update Date

1/22/2018 11:54:54 AM

Metabolite ID

PAMDB000023

Identification

Name:

Carnitine

Description:

Carnitine is a quaternary ammonium compound biosynthesized from the amino acids lysine and methionine. In living cells, it is required for the transport of fatty acids during the breakdown of lipids (fats) for the generation of metabolic energy. Carnitine was originally found as a growth factor for mealworms and labeled vitamin Bt. Carnitine exists in two stereoisomers: Its biologically active form is L-carnitine, whereas its enantiomer, D-carnitine, is biologically inactive. Pseudomonas aeruginosa converts carnitine, via crotonobetaine, to gamma-butyrobetaine in the presence of C and N sources and under anaerobic conditions. This two-step pathway requires L-(-)-carnitine dehydratase and crotonobetaine reductase. Anaerobic carnitine metabolism in Pseudomonas aeruginosa involves six genes organized in the cai operon and located at the first minute on the Pseudomonas aeruginosa chromosome.

Structure

🔍MOL SDF PDB SMILES InChI View Structure

Synonyms:

γ-Trimethyl-hydroxybutyrobetaine
(-)-(R)-3-Hydroxy-4-(trimethylammonio)butyrate
(-)-(R)-3-Hydroxy-4-(trimethylammonio)butyric acid
(-)-Carnitine
(-)-L-Carnitine
(3-carboxy-2-hydroxypropyl)trimethyl-Ammonium hydroxide inner salt
(R)-(3-Carboxy-2-hydroxypropyl)trimethylammonium hydroxide
(R)-Carnitine
(S)-carnitine
1-carnitine
3-Carboxy-2-hydroxy-N,N,N-trimethyl-1-propanaminium
3-Carboxy-2-hydroxy-N,N,N-trimethyl-1-Propanaminium hydroxide inner salt
3-Hydroxy-4-trimethylammoniobutanoate
3-Hydroxy-4-trimethylammoniobutanoic acid
Bicarnesine
Carniking
Carniking 50
Carnilean
Carnipass
Carnipass 20
Carnitene
Carnitine (L-form)
Carnitor
Carnitor, Levocarnitine
D-carnitine
Delta-carnitine
Dl-carnitine
g-Trimethyl-ammonium-b-hydroxybutirate
g-Trimethyl-ammonium-b-hydroxybutiric acid
g-Trimethyl-b-hydroxybutyrobetaine
g-Trimethyl-hydroxybutyrobetaine
Gamma-trimethyl-ammonium-beta-hydroxybutirate
gamma-Trimethyl-ammonium-beta-hydroxybutiric acid
Gamma-trimethyl-beta-hydroxybutyrobetaine
Gamma-Trimethyl-hydroxybutyrobetaine
Karnitin
L-γ-trimethyl-β-hydroxybutyrobetaine
L-(-)-Carnitine
L-Carnitine
L-g-Trimethyl-b-hydroxybutyrobetaine
L-gamma-Trimethyl-beta-hydroxybutyrobetaine
L-γ-Trimethyl-β-hydroxybutyrobetaine
Levocarnitina
Levocarnitine
Levocarnitine chloride
Levocarnitinum
R-(-)-3-Hydroxy-4-trimethylaminobutyrate
R-(-)-3-Hydroxy-4-trimethylaminobutyric acid
Vitamin B T
Vitamin Bt
γ-Trimethyl-ammonium-β-hydroxybutirate
γ-Trimethyl-ammonium-β-hydroxybutiric acid
γ-Trimethyl-hydroxybutyrobetaine
γ-Trimethyl-β-hydroxybutyrobetaine
δ-Carnitine

Chemical Formula:

C₇H₁₆NO₃

Average Molecular Weight:

162.2068

Monoisotopic Molecular Weight:

162.113018383

InChI Key:

PHIQHXFUZVPYII-UHFFFAOYSA-O

InChI:

InChI=1S/C7H15NO3/c1-8(2,3)5-6(9)4-7(10)11/h6,9H,4-5H2,1-3H3/p+1

CAS number:

541-15-1

IUPAC Name:

(3-carboxy-2-hydroxypropyl)trimethylazanium

Traditional IUPAC Name:

(+-)-carnitine

SMILES:

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

Chemical Taxonomy

Taxonomy Description

This compound belongs to the class of organic compounds known as hydroxy fatty acids. These are fatty acids in which the chain bears a hydroxyl group.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acids and conjugates

Direct Parent

Hydroxy fatty acids

Alternative Parents

Substituents

Hydroxy fatty acid
Short-chain hydroxy acid
Choline
Beta-hydroxy acid
Hydroxy acid
Quaternary ammonium salt
Secondary alcohol
1,2-aminoalcohol
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Carbonyl group
Amine
Alcohol
Organic cation
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Physical Properties

State:

Solid

Charge:

Melting point:

210-212 °C

Experimental Properties:

Property	Value	Source
Water Solubility:	2500.0 mg/ml	PhysProp

Predicted Properties

Property	Value	Source
Water Solubility	6.58 mg/mL	ALOGPS
logP	-2.8	ALOGPS
logP	-4.9	ChemAxon
logS	-1.5	ALOGPS
pKa (Strongest Acidic)	4.2	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	57.53 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	52.65 m³·mol^-1	ChemAxon
Polarizability	17.18 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 + Carnitine > ADP + Carnitine + Hydrogen ion + Phosphate
Adenosine triphosphate + Water + Carnitine > ADP + Carnitine + Hydrogen ion + Phosphate
-->-->Adenosine triphosphate + Coenzyme A + Carnitine > ADP + L-Carnitinyl-CoA + Phosphate
Adenosine triphosphate + Coenzyme A + Carnitine > ADP + D-Carnitinyl-CoA + Phosphate
Carnitine + Crotonobetainyl-CoA <> L-Carnitinyl-CoA + Crotonobetaine
gamma-Butyrobetainyl-CoA + Carnitine <> L-Carnitinyl-CoA + gamma-Butyrobetaine
Coenzyme A + Carnitine + Adenosine triphosphate > L-Carnitinyl-CoA + Adenosine monophosphate + Pyrophosphate

Pathways:

ABC transporters pae02010
Lysine degradation pae00310

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
Ishii, N., Nakahigashi, K., Baba, T., Robert, M., Soga, T., Kanai, A., Hirasawa, T., Naba, M., Hirai, K., Hoque, A., Ho, P. Y., Kakazu, Y., Sugawara, K., Igarashi, S., Harada, S., Masuda, T., Sugiyama, N., Togashi, T., Hasegawa, M., Takai, Y., Yugi, K., Arakawa, K., Iwata, N., Toya, Y., Nakayama, Y., Nishioka, T., Shimizu, K., Mori, H., Tomita, M. (2007). "Multiple high-throughput analyses monitor the response of E. coli to perturbations." Science 316:593-597. Pubmed: 17379776
Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
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
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)

Download (PDF)

Links

External Links:

Resource	Link
CHEBI ID	17126
HMDB ID	HMDB00062
Pubchem Compound ID	10917
Kegg ID	C00487
ChemSpider ID	83
Wikipedia	L-Carnitine
BioCyc ID	CARNITINE
EcoCyc ID	CARNITINE

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

Carnitine (PAMDB000023)

Structure for Carnitine (PAMDB000023)

Enzymes

Transporters