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Record Information
Version2.0
Created at2020-11-23 18:25:12 UTC
Updated at2024-09-17 15:45:25 UTC
NP-MRD IDNP0002610
Secondary Accession NumbersNone
Natural Product Identification
Common NameD-Carnitine
Provided ByBMRBBMRB logo
Description(3-Carboxy-2-(R)-Hydroxy-Propyl)-Trimethyl-Ammonium is also known as carnitine. It was first documented in 1998 (PMID: 9572066). Based on a literature review very few articles have been published on (3-Carboxy-2-(R)-Hydroxy-Propyl)-Trimethyl-Ammonium (PMID: 11880112) (PMID: 12908852) (PMID: 16368715) (PMID: 17984079).
Structure
Thumb
Synonyms
ValueSource
CARNITINEChEBI
(-)-CarnitineHMDB
(-)-L-CarnitineHMDB
(R)-CarnitineHMDB
L-CarnitineHMDB
L-gamma-Trimethyl-beta-hydroxybutyrobetaineHMDB
L-γ-Trimethyl-β-hydroxybutyrobetaineHMDB
LevocarnitineHMDB
Chemical FormulaC7H16NO3
Average Mass162.2068 Da
Monoisotopic Mass162.11302 Da
IUPAC Name[(2R)-3-carboxy-2-hydroxypropyl]trimethylazanium
Traditional Name(+-)-carnitine
CAS Registry NumberNot Available
SMILES
C[N+](C)(C)C[C@H](O)CC(O)=O
InChI Identifier
InChI=1S/C7H15NO3/c1-8(2,3)5-6(9)4-7(10)11/h6,9H,4-5H2,1-3H3/p+1/t6-/m1/s1
InChI KeyPHIQHXFUZVPYII-ZCFIWIBFSA-O
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of OriginNot Available
Chemical Taxonomy
DescriptionThis compound 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
  • 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 FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-2.8ALOGPS
logP-4.9ChemAxon
logS-1.5ALOGPS
pKa (Strongest Acidic)4.2ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity52.65 m³·mol⁻¹ChemAxon
Polarizability17.2 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDDB02648
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID10456
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI ID39547
Good Scents IDNot Available
References
General References
  1. Wachter S, Vogt M, Kreis R, Boesch C, Bigler P, Hoppeler H, Krahenbuhl S: Long-term administration of L-carnitine to humans: effect on skeletal muscle carnitine content and physical performance. Clin Chim Acta. 2002 Apr;318(1-2):51-61. [PubMed:11880112 ]
  2. Evans AM, Fornasini G: Pharmacokinetics of L-carnitine. Clin Pharmacokinet. 2003;42(11):941-67. [PubMed:12908852 ]
  3. Pastoris O, Dossena M, Foppa P, Catapano M, Arbustini E, Bellini O, Dal Bello B, Minzioni G, Ceriana P, Barzaghi N: Effect of L-carnitine on myocardial metabolism: results of a balanced, placebo-controlled, double-blind study in patients undergoing open heart surgery. Pharmacol Res. 1998 Feb;37(2):115-22. [PubMed:9572066 ]
  4. Stephens FB, Constantin-Teodosiu D, Laithwaite D, Simpson EJ, Greenhaff PL: Insulin stimulates L-carnitine accumulation in human skeletal muscle. FASEB J. 2006 Feb;20(2):377-9. Epub 2005 Dec 20. [PubMed:16368715 ]