NP-MRD: Showing NP-Card for D-Carnitine (NP0002610)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

1.0

Created at

2020-11-23 18:25:12 UTC

Updated at

2021-08-12 19:51:39 UTC

NP-MRD ID

NP0002610

Secondary Accession Numbers

None

Natural Product Identification

Common Name

D-Carnitine

Provided By

BMRB

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

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

COMPND    HMDB0000062
HETATM    1  C1  UNL     1      -2.045  -1.115   0.460  1.00  0.00           C  
HETATM    2  N1  UNL     1      -1.493   0.086  -0.133  1.00  0.00           N1+
HETATM    3  C2  UNL     1      -1.537   1.160   0.811  1.00  0.00           C  
HETATM    4  C3  UNL     1      -2.389   0.459  -1.238  1.00  0.00           C  
HETATM    5  C4  UNL     1      -0.220  -0.193  -0.694  1.00  0.00           C  
HETATM    6  C5  UNL     1       0.932  -0.184   0.255  1.00  0.00           C  
HETATM    7  O1  UNL     1       1.139   1.013   0.899  1.00  0.00           O  
HETATM    8  C6  UNL     1       2.196  -0.448  -0.574  1.00  0.00           C  
HETATM    9  C7  UNL     1       3.368  -0.446   0.313  1.00  0.00           C  
HETATM   10  O2  UNL     1       3.622  -1.470   1.009  1.00  0.00           O  
HETATM   11  O3  UNL     1       4.199   0.647   0.408  1.00  0.00           O  
HETATM   12  H1  UNL     1      -2.692  -0.848   1.332  1.00  0.00           H  
HETATM   13  H2  UNL     1      -2.668  -1.648  -0.287  1.00  0.00           H  
HETATM   14  H3  UNL     1      -1.206  -1.747   0.798  1.00  0.00           H  
HETATM   15  H4  UNL     1      -1.005   2.059   0.450  1.00  0.00           H  
HETATM   16  H5  UNL     1      -1.259   0.867   1.840  1.00  0.00           H  
HETATM   17  H6  UNL     1      -2.620   1.480   0.884  1.00  0.00           H  
HETATM   18  H7  UNL     1      -3.121   1.216  -0.898  1.00  0.00           H  
HETATM   19  H8  UNL     1      -1.797   0.926  -2.069  1.00  0.00           H  
HETATM   20  H9  UNL     1      -2.958  -0.412  -1.612  1.00  0.00           H  
HETATM   21  H10 UNL     1      -0.256  -1.197  -1.170  1.00  0.00           H  
HETATM   22  H11 UNL     1      -0.021   0.526  -1.525  1.00  0.00           H  
HETATM   23  H12 UNL     1       0.858  -1.017   0.968  1.00  0.00           H  
HETATM   24  H13 UNL     1       1.398   0.820   1.834  1.00  0.00           H  
HETATM   25  H14 UNL     1       2.104  -1.432  -1.077  1.00  0.00           H  
HETATM   26  H15 UNL     1       2.282   0.370  -1.328  1.00  0.00           H  
HETATM   27  H16 UNL     1       5.190   0.528   0.342  1.00  0.00           H  
CONECT    1    2   12   13   14
CONECT    2    3    4    5
CONECT    3   15   16   17
CONECT    4   18   19   20
CONECT    5    6   21   22
CONECT    6    7    8   23
CONECT    7   24
CONECT    8    9   25   26
CONECT    9   10   10   11
CONECT   11   27
END

View in JSmol View NMR Assignments

Synonyms

Value	Source
CARNITINE	ChEBI
(-)-Carnitine	HMDB
(-)-L-Carnitine	HMDB
(R)-Carnitine	HMDB
L-Carnitine	HMDB
L-gamma-Trimethyl-beta-hydroxybutyrobetaine	HMDB
L-γ-Trimethyl-β-hydroxybutyrobetaine	HMDB
Levocarnitine	HMDB

Chemical Formula

C₇H₁₆NO₃

Average Mass

162.2068 Da

Monoisotopic Mass

162.11302 Da

IUPAC Name

[(2R)-3-carboxy-2-hydroxypropyl]trimethylazanium

Traditional Name

(+-)-carnitine

CAS Registry Number

Not 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 Key

PHIQHXFUZVPYII-ZCFIWIBFSA-O

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

This compound 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

carnitinium (CHEBI:39547 )

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
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	17.2 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

DB02648

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

10456

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

39547

Good Scents ID

Not Available

References

General References

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 ]
Evans AM, Fornasini G: Pharmacokinetics of L-carnitine. Clin Pharmacokinet. 2003;42(11):941-67. [PubMed:12908852 ]
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 ]
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 ]
Ulrich EL, Akutsu H, Doreleijers JF, Harano Y, Ioannidis YE, Lin J, Livny M, Mading S, Maziuk D, Miller Z, Nakatani E, Schulte CF, Tolmie DE, Kent Wenger R, Yao H, Markley JL: BioMagResBank. Nucleic Acids Res. 2008 Jan;36(Database issue):D402-8. doi: 10.1093/nar/gkm957. Epub 2007 Nov 4. [PubMed:17984079 ]

Showing NP-Card for D-Carnitine (NP0002610)

MOL for NP0002610 (D-Carnitine)

3D MOL for NP0002610 (D-Carnitine)

3D SDF for NP0002610 (D-Carnitine)

3D-SDF for NP0002610 (D-Carnitine)

PDB for NP0002610 (D-Carnitine)

3D PDB for NP0002610 (D-Carnitine)

SMILES for NP0002610 (D-Carnitine)

INCHI for NP0002610 (D-Carnitine)

Structure for NP0002610 (D-Carnitine)

3D Structure for NP0002610 (D-Carnitine)