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Showing NP-Card for (+)-carnitine (NP0214686)

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Record Information
Version2.0
Created at2022-09-05 14:03:41 UTC
Updated at2022-09-05 14:03:41 UTC
NP-MRD IDNP0214686
Secondary Accession NumbersNone
Natural Product Identification
Common Name(+)-carnitine
DescriptionL-Carnitine, also known as carnitine D-form, belongs to the class of organic compounds known as carnitines. These are organic compounds containing the quaternary ammonium compound carnitine. L-Carnitine is an extremely weak basic (essentially neutral) compound (based on its pKa). Within humans, L-carnitine participates in a number of enzymatic reactions. In particular, propionyl-CoA and L-carnitine can be converted into propionylcarnitine; which is catalyzed by the enzyme carnitine O-acetyltransferase. In addition, 4,8-dimethylnonanoyl-CoA and L-carnitine can be converted into 4,8 dimethylnonanoyl carnitine through the action of the enzyme peroxisomal carnitine O-octanoyltransferase. In humans, L-carnitine is involved in oxidation of branched-chain fatty acids. (+)-carnitine is found in Apis cerana. The (S)-enantiomer of carnitine.
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0214686 ((+)-carnitine)


  Mrv0541 02241222092D          

 12 11  0  0  1  0            999 V2000
    1.7605    1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750    1.4289    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    2.8875    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1895    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9039    1.4289    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9039    0.6039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6184    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3329    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0474    1.8414    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    5.3329    0.6039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5683    0.6752    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  2  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  6  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  2  0  0  0  0
  6 12  1  1  0  0  0
M  CHG  2   2   1  10  -1
M  END
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3D MOL for NP0214686 ((+)-carnitine)

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3D SDF for NP0214686 ((+)-carnitine)

  Mrv0541 02241222092D          

 12 11  0  0  1  0            999 V2000
    1.7605    1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750    1.4289    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    2.8875    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1895    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9039    1.4289    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9039    0.6039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6184    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3329    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0474    1.8414    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    5.3329    0.6039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5683    0.6752    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  2  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  6  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  2  0  0  0  0
  6 12  1  1  0  0  0
M  CHG  2   2   1  10  -1
M  END
> <DATABASE_ID>
NP0214686

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@](O)(CC([O-])=O)C[N+](C)(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C7H15NO3/c1-8(2,3)5-6(9)4-7(10)11/h6,9H,4-5H2,1-3H3/t6-/m0/s1

> <INCHI_KEY>
PHIQHXFUZVPYII-LURJTMIESA-N

> <FORMULA>
C7H15NO3

> <MOLECULAR_WEIGHT>
161.1989

> <EXACT_MASS>
161.105193351

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
16.75716840796975

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3S)-3-hydroxy-4-(trimethylazaniumyl)butanoate

> <ALOGPS_LOGP>
-2.90

> <JCHEM_LOGP>
-4.887506048138412

> <ALOGPS_LOGS>
-1.60

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.524970024955305

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.196175564563187

> <JCHEM_PKA_STRONGEST_BASIC>
-3.5695232571229383

> <JCHEM_POLAR_SURFACE_AREA>
60.36

> <JCHEM_REFRACTIVITY>
63.4853

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.33e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(+)-carnitine

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for NP0214686 ((+)-carnitine)
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PDB for NP0214686 ((+)-carnitine)
HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0       3.286   1.897   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0       4.620   2.667   0.000  0.00  0.00           N+1
HETATM    3  C   UNK     0       5.390   1.334   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.850   4.001   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.954   3.437   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.287   2.667   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       7.287   1.127   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       8.621   3.437   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.955   2.667   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      11.288   3.437   0.000  0.00  0.00           O-1
HETATM   11  O   UNK     0       9.955   1.127   0.000  0.00  0.00           O+0
HETATM   12  H   UNK     0       6.661   1.260   0.000  0.00  0.00           H+0
CONECT    1    2                                                            
CONECT    2    1    3    4    5                                             
CONECT    3    2                                                            
CONECT    4    2                                                            
CONECT    5    2    6                                                       
CONECT    6    5    7    8   12                                             
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9                                                            
CONECT   12    6                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   22    0
END

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3D PDB for NP0214686 ((+)-carnitine)
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SMILES for NP0214686 ((+)-carnitine)
[H][C@](O)(CC([O-])=O)C[N+](C)(C)C
Download
INCHI for NP0214686 ((+)-carnitine)
InChI=1S/C7H15NO3/c1-8(2,3)5-6(9)4-7(10)11/h6,9H,4-5H2,1-3H3/t6-/m0/s1
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View in JSmol
Synonyms
ValueSource
(+)-CarnitineChEBI
Carnitine D-formChEBI
D-(3-Carboxy-2-hydroxypropyl)trimethylammonium hydroxide, inner saltChEBI
D-CarnitineChEBI
Chemical FormulaC7H15NO3
Average Mass161.1989 Da
Monoisotopic Mass161.10519 Da
IUPAC Name(3S)-3-hydroxy-4-(trimethylazaniumyl)butanoate
Traditional Name(+)-carnitine
CAS Registry NumberNot Available
SMILES
[H][C@](O)(CC([O-])=O)C[N+](C)(C)C
InChI Identifier
InChI=1S/C7H15NO3/c1-8(2,3)5-6(9)4-7(10)11/h6,9H,4-5H2,1-3H3/t6-/m0/s1
InChI KeyPHIQHXFUZVPYII-LURJTMIESA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
2D NMR[1H, 1H]-TOCSY 2D NMR Spectrum (experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Apis ceranaLOTUS Database
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
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-2.9ALOGPS
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
Polarizability16.76 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC15025  
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkCarnitine  
METLIN IDNot Available
PubChem Compound2724480  
PDB IDNot Available
ChEBI ID11060  
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]