Showing metabocard for Carnitine (MMDBc0029466)

Record Information
Version1.0
StatusDetected and Quantified
Creation Date2021-11-17 23:23:26 UTC
Update Date2022-08-31 06:58:24 UTC
Metabolite IDMMDBc0029466
Metabolite Identification
Common NameCarnitine
DescriptionCarnitine 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
MOLSDFPDBSMILESInChI

MOL for #<Metabolite:0x00007f3de14a6e30>


  Mrv1652310061713372D          

 11 10  0  0  0  0            999 V2000
    0.4125    3.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1105    2.4454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    2.8579    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
   -0.0000    1.4289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375   -0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  4  1  0  0  0  0
  6  5  1  0  0  0  0
  7  4  1  0  0  0  0
  8  1  1  0  0  0  0
  8  2  1  0  0  0  0
  8  3  1  0  0  0  0
  8  5  1  0  0  0  0
  9  6  1  0  0  0  0
 10  7  2  0  0  0  0
 11  7  1  0  0  0  0
M  CHG  1   8   1
M  END
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3D MOL for #<Metabolite:0x00007f3de14a6e30>

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3D SDF for #<Metabolite:0x00007f3de14a6e30>

  Mrv1652310061713372D          

 11 10  0  0  0  0            999 V2000
    0.4125    3.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1105    2.4454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    2.8579    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
   -0.0000    1.4289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375   -0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  4  1  0  0  0  0
  6  5  1  0  0  0  0
  7  4  1  0  0  0  0
  8  1  1  0  0  0  0
  8  2  1  0  0  0  0
  8  3  1  0  0  0  0
  8  5  1  0  0  0  0
  9  6  1  0  0  0  0
 10  7  2  0  0  0  0
 11  7  1  0  0  0  0
M  CHG  1   8   1
M  END
> <DATABASE_ID>
MMDBc0029466

> <DATABASE_NAME>
MIME

> <SMILES>
C[N+](C)(C)CC(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

> <INCHI_KEY>
PHIQHXFUZVPYII-UHFFFAOYSA-O

> <FORMULA>
C7H16NO3

> <MOLECULAR_WEIGHT>
162.2068

> <EXACT_MASS>
162.113018383

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
27

> <JCHEM_AVERAGE_POLARIZABILITY>
17.184652203015233

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
1

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3-carboxy-2-hydroxypropyl)trimethylazanium

> <ALOGPS_LOGP>
-2.75

> <JCHEM_LOGP>
-4.887506048138412

> <ALOGPS_LOGS>
-1.48

> <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>
57.53

> <JCHEM_REFRACTIVITY>
52.648199999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.58e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
carnitina

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for #<Metabolite:0x00007f3de14a6e30>
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PDB for #<Metabolite:0x00007f3de14a6e30>
HEADER    PROTEIN                                 06-OCT-17   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-OCT-17         0                                  
HETATM    1  C   UNK     0       0.770   6.668   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.206   4.565   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.874   6.105   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.310   1.334   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.310   4.001   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.540   2.667   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.540   0.000   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0       1.540   5.335   0.000  0.00  0.00           N+1
HETATM    9  O   UNK     0      -0.000   2.667   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0       2.310  -1.334   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
CONECT    1    8                                                            
CONECT    2    8                                                            
CONECT    3    8                                                            
CONECT    4    6    7                                                       
CONECT    5    6    8                                                       
CONECT    6    4    5    9                                                  
CONECT    7    4   10   11                                                  
CONECT    8    1    2    3    5                                             
CONECT    9    6                                                            
CONECT   10    7                                                            
CONECT   11    7                                                            
MASTER        0    0    0    0    0    0    0    0   11    0   20    0
END

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3D PDB for #<Metabolite:0x00007f3de14a6e30>
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SMILES for #<Metabolite:0x00007f3de14a6e30>
C[N+](C)(C)CC(O)CC(O)=O
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INCHI for #<Metabolite:0x00007f3de14a6e30>
InChI=1S/C7H15NO3/c1-8(2,3)5-6(9)4-7(10)11/h6,9H,4-5H2,1-3H3/p+1
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Synonyms
ValueSource
3-Hydroxy-4-(trimethylammonio)butanoic acidChEBI
gamma-Trimethyl-hydroxybutyrobetaineKegg
3-Hydroxy-4-trimethylammoniobutanoateKegg
3-Hydroxy-4-(trimethylammonio)butanoateGenerator
g-Trimethyl-hydroxybutyrobetaineGenerator
Γ-trimethyl-hydroxybutyrobetaineGenerator
3-Hydroxy-4-trimethylammoniobutanoic acidGenerator
Molecular FormulaC7H16NO3
Average Mass162.2068
Monoisotopic Mass162.113018383
IUPAC Name(3-carboxy-2-hydroxypropyl)trimethylazanium
Traditional Namecarnitina
CAS Registry Number541-15-1
SMILES
C[N+](C)(C)CC(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
InChI KeyPHIQHXFUZVPYII-UHFFFAOYSA-O