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L-Carnitine (M2MDB005774)

Record Information
Version2.0
Creation Date2015-06-17 11:15:02 -0600
Update Date2015-10-02 02:25:53 -0600
Secondary Accession Numbers
  • ECMDB23900
Identification
Name:L-Carnitine
DescriptionL-carnitine is a metabolite in E. coli., it can be metabolized under anaerobic conditions [PMID: 2266491]. In L-carnitine degradation I pathway, it is a substrate for enzyme Carnitine-CoA ligase which catalyzes the chemical reaction L-carnitine + ATP + coenzyme A -> L-carnitinyl-CoA + AMP + diphosphate. Another enzyme gamma-butyrobetainyl-CoA:carnitine CoA transferase catalyzes the reaction L-carnitine + γ-butyrobetainyl-CoA -> L-carnitinyl-CoA + γ-butyrobetaine (EcoCyc compound: CARNITINE).
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms:
  • (R)-Carnitine
  • 3-Carboxy-2-hydroxy-N,N,N-trimethyl-1-propanaminium hydroxide, inner salt
  • L-g-Trimethyl-b-hydroxybutyrobetaine
  • L-gamma-Trimethyl-beta-hydroxybutyrobetaine
  • L-γ-Trimethyl-β-hydroxybutyrobetaine
  • Levocarnitine
  • Vitamin BT
Chemical Formula:C7H15NO3
Weight:Average: 161.1989
Monoisotopic: 161.105193351
InChI Key:PHIQHXFUZVPYII-ZCFIWIBFSA-N
InChI:InChI=1S/C7H15NO3/c1-8(2,3)5-6(9)4-7(10)11/h6,9H,4-5H2,1-3H3/t6-/m1/s1
CAS number:541-15-1
IUPAC Name:(3R)-3-hydroxy-4-(trimethylazaniumyl)butanoate
Traditional IUPAC Name:L-carnitine
SMILES:C[N+](C)(C)C[C@H](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.
KingdomOrganic compounds
Super ClassOrganic nitrogen compounds
ClassOrganonitrogen compounds
Sub ClassQuaternary ammonium salts
Direct ParentCarnitines
Alternative Parents
Substituents
  • Carnitine
  • Beta-hydroxy acid
  • Short-chain hydroxy acid
  • Fatty acid
  • Hydroxy acid
  • Tetraalkylammonium salt
  • 1,2-aminoalcohol
  • Carboxylic acid salt
  • Secondary alcohol
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organic oxygen compound
  • Organooxygen compound
  • Organic zwitterion
  • Organic salt
  • Hydrocarbon derivative
  • Organic oxide
  • Carbonyl group
  • Organopnictogen compound
  • Amine
  • Alcohol
  • 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 Solubility5.33 g/LALOGPS
logP-2.9ALOGPS
logP-4.9ChemAxon
logS-1.6ALOGPS
pKa (Strongest Acidic)4.2ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area60.36 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity63.49 m³·mol⁻¹ChemAxon
Polarizability16.93 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
(E)-4-(Trimethylammonio)but-2-enoyl-CoA + L-Carnitine + 4-Trimethylammoniobutanoyl-CoA <> Crotonobetaine + L-Carnitinyl-CoA + gamma-Butyrobetaine
Palmityl-CoA + L-Carnitine <> L-Palmitoylcarnitine + Coenzyme A
L-Carnitine + Coenzyme A + Adenosine triphosphate > D-Carnitinyl-CoA + Adenosine monophosphate + Pyrophosphate
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:Not Available
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00di-9100000000-1b25dacb04c3ed5be8d0View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00di-9100000000-c15eaa190d1e28a4839aView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, PositiveNot AvailableView in JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-03di-0900000000-9b579c570aab7c7d3a21View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0ik9-0900000000-e37d3def2de1af5bd2f5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0ue9-8900000000-cf37f0a721cd52d86e8eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0r0c-9200000000-a11a4872036f3c33d25aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0a4l-9000000000-2402e260a330ff1772a1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT , positivesplash10-0w29-6900000000-d0136248acdd706e650bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0ik9-2900000000-61732bb10307f2b183caView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0zg0-9400000000-15c3db3324f1d46d3c7cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0ik9-2900000000-ee79f10dce9fc09246ecView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01ox-0900000000-3bffd5143cf8b072299eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00kf-0900000000-e68f553bcb15d3ef5b47View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00di-9200000000-c5b43723951af6da48cfView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-1900000000-dd1b1a023937cdcb11afView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-114i-3900000000-9f24d3bc535736149e2aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9000000000-632ef17d9dde38586990View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-3900000000-97af6636a917c0edea61View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01pc-9300000000-543e21cb6b9785149e31View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-08fr-9000000000-9128d6fe96d9c7276695View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
References
References:Not Available
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID16347
HMDB IDHMDB0000062
Pubchem Compound ID10917
Kegg IDC00318
ChemSpider ID2006614
Wikipedia IDCarnitine
BioCyc IDNot Available

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
Protein Details
2. 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