ECMDB: Carnitine (ECMDB00062) (M2MDB000023)

Identification Taxonomy Physical Properties Biological Properties Spectra Concentrations Links References Enzymes (5)Transporters (7)XML

Proteins (31)

Record Information

Version

2.0

Creation Date

2012-05-31 09:56:31 -0600

Update Date

2015-09-13 12:56:05 -0600

Secondary Accession Numbers

ECMDB00062

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. E. coli 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 Escherichia coli involves six genes organized in the cai operon and located at the first minute on the E. coli chromosome.

Structure

MOL SDF PDB SMILES InChI

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

Weight:

Average: 162.2068
Monoisotopic: 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:

carnitina

SMILES:

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

Chemical Taxonomy

Description

belongs to the class of organic compounds known as carnitines. These are organic compounds containing the quaternary ammonium compound carnitine.

Kingdom

Organic compounds

Super Class

Organic nitrogen compounds

Class

Organonitrogen compounds

Sub Class

Quaternary ammonium salts

Direct Parent

Carnitines

Alternative Parents

Substituents

Carnitine
Beta-hydroxy acid
Short-chain hydroxy acid
Fatty acid
Hydroxy acid
Tetraalkylammonium salt
1,2-aminoalcohol
Secondary alcohol
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Organic oxygen compound
Alcohol
Organooxygen compound
Organic salt
Hydrocarbon derivative
Organic oxide
Carbonyl group
Organopnictogen compound
Amine
Organic cation
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

quaternary ammonium ion (CHEBI:3424 )

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 g/L	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
Carnitine + gamma-Butyrobetainyl-CoA > L-Carnitinyl-CoA + gamma-Butyrobetaine

SMPDB Pathways:

Not Available

KEGG Pathways:

ABC transporters ec02010
Lysine degradation ec00310

EcoCyc Pathways:

carnitine degradation I CARNMET-PWY

Concentrations

Concentration	Strain	Media	Growth Status	Growth System	Temperature	Details
4± 0 uM	BW25113	48 mM Na2HPO4, 22 mM KH2PO4, 10 mM NaCl, 45 mM (NH4)2SO4, supplemented with 1 mM MgSO4, 1 mg/l thiamine·HCl, 5.6 mg/l CaCl2, 8 mg/l FeCl3, 1 mg/l MnCl2·4H2O, 1.7 mg/l ZnCl2, 0.43 mg/l CuCl2·2H2O, 0.6 mg/l CoCl2·2H2O and 0.6 mg/l Na2MoO4·2H2O. 4 g/L Gluco	Stationary Phase, glucose limited	Bioreactor, pH controlled, O2 and CO2 controlled, dilution rate: 0.2/h	37 oC	PMID: 17379776

Find out more about how we convert literature concentrations.

Spectra

Spectra:

Spectrum Type	Description	Splash Key
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-05fr-9200000000-dc9f579d8b831ed40bed	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-01ox-0900000000-fe7021da394a24880212	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-02bf-1900000000-a655a8313901692115f6	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00di-9200000000-b173346753f571ba54dd	View in MoNA
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View 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
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

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

Protein Details

3. 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

4. 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

5. 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

6. 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

7. 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

Carnitine (ECMDB00062) (M2MDB000023)

Structure for #<Compound:0xa8c13934>

Enzymes

Transporters