NP-MRD: Showing NP-Card for Malonylcarnitine (NP0001047)

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Record Information

Version

2.0

Created at

2006-05-22 14:17:36 UTC

Updated at

2024-09-17 15:43:54 UTC

NP-MRD ID

NP0001047

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Malonylcarnitine

Description

Malonylcarnitine is a metabolite that accumulates with specific disruption of fatty-acid oxidation caused by the impaired entry of long-chain acylcarnitine esters into the mitochondria and failure of the mitochondrial respiratory chain at complex 11 and malonyl-CoA decarboxylase (EC 4.1.1.9) Deficiency (OMIM: 248360 ). Malonylcarnitine has also been found to accumulate in some newborns with medium-chain acyl-CoA dehydrogenase (EC 1.3.99.3) Deficiency (OMIM: 201450 ). (PMID: 11558490 , 15303003 , 12651823 ).

Structure

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

HMDB0002095
     RDKit          3D
Malonylcarnitine
 34 33  0  0  0  0  0  0  0  0999 V2000
   -2.8374   -1.9144    0.5063 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2819   -0.6223    0.0702 N   0  0  0  0  0  4  0  0  0  0  0  0
   -2.3372   -0.6107   -1.3722 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1831    0.3919    0.5752 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9633   -0.5515    0.6037 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0251    0.3774   -0.0771 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4357    1.8273    0.0251 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5582    2.6787   -0.6804 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6785    2.8272   -0.1099 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3449    3.3011   -1.8832 O   0  0  0  0  0  1  0  0  0  0  0  0
    1.2250    0.2798    0.6240 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4028   -0.0427   -0.0294 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3049   -0.2435   -1.2755 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7129   -0.1496    0.6836 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7853   -0.4987   -0.2499 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5125   -0.6646   -1.4654 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0758   -0.6350    0.2515 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9278   -1.9097    0.5433 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4485   -2.1041    1.5415 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4126   -2.7499   -0.1132 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1165   -1.3224   -1.7290 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3918   -0.9195   -1.8478 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6850    0.4001   -1.7006 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5848    1.0110   -0.2588 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0631   -0.0340    1.0857 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6594    1.0259    1.3372 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5146   -1.5712    0.5807 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0276   -0.2673    1.6740 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1825    0.1575   -1.1250 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4584    2.1825    1.0780 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4081    1.9975   -0.4741 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8616    0.8036    1.2190 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6401   -0.9593    1.4444 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4770   -1.4910    0.5482 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  2  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
  6 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  3 21  1  0
  3 22  1  0
  3 23  1  0
  4 24  1  0
  4 25  1  0
  4 26  1  0
  5 27  1  0
  5 28  1  0
  6 29  1  6
  7 30  1  0
  7 31  1  0
 14 32  1  0
 14 33  1  0
 17 34  1  0
M  CHG  2   2   1  10  -1
M  END

      
  Mrv1652305271900202D          

 17 16  0  0  1  0            999 V2000
   -0.9059    2.7770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9059    1.9520    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
   -1.7309    1.9520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0809    1.9520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9059    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1913    0.7145    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1913   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9059   -0.5230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6204   -0.1105    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   -0.9059   -1.3480    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5230    1.1270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2374    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2374   -0.1105    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6664    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3809    1.1270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6664   -0.1105    0.0000 O   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  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  2  0  0  0  0
  6 11  1  6  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  2  0  0  0  0
M  CHG  2   2   1   9  -1
M  END
> <DATABASE_ID>
NP0001047

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C10H17NO6/c1-11(2,3)6-7(4-8(12)13)17-10(16)5-9(14)15/h7H,4-6H2,1-3H3,(H-,12,13,14,15)/t7-/m1/s1

> <INCHI_KEY>
ZGNBLKBZJBJFDG-SSDOTTSWSA-N

> <FORMULA>
C10H17NO6

> <MOLECULAR_WEIGHT>
247.247

> <EXACT_MASS>
247.105587271

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
34

> <JCHEM_AVERAGE_POLARIZABILITY>
23.67588410523618

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3R)-3-[(2-carboxyacetyl)oxy]-4-(trimethylazaniumyl)butanoate

> <ALOGPS_LOGP>
-1.98

> <JCHEM_LOGP>
-4.554152191805079

> <ALOGPS_LOGS>
-2.95

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
4.169537385693162

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.4676356359550904

> <JCHEM_PKA_STRONGEST_BASIC>
-7.172258267685226

> <JCHEM_POLAR_SURFACE_AREA>
103.73000000000002

> <JCHEM_REFRACTIVITY>
78.98089999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.41e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3R)-3-[(2-carboxyacetyl)oxy]-4-(trimethylammonio)butanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0002095
     RDKit          3D
Malonylcarnitine
 34 33  0  0  0  0  0  0  0  0999 V2000
   -2.8374   -1.9144    0.5063 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2819   -0.6223    0.0702 N   0  0  0  0  0  4  0  0  0  0  0  0
   -2.3372   -0.6107   -1.3722 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1831    0.3919    0.5752 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9633   -0.5515    0.6037 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0251    0.3774   -0.0771 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4357    1.8273    0.0251 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5582    2.6787   -0.6804 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6785    2.8272   -0.1099 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3449    3.3011   -1.8832 O   0  0  0  0  0  1  0  0  0  0  0  0
    1.2250    0.2798    0.6240 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4028   -0.0427   -0.0294 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3049   -0.2435   -1.2755 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7129   -0.1496    0.6836 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7853   -0.4987   -0.2499 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5125   -0.6646   -1.4654 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0758   -0.6350    0.2515 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9278   -1.9097    0.5433 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4485   -2.1041    1.5415 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4126   -2.7499   -0.1132 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1165   -1.3224   -1.7290 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3918   -0.9195   -1.8478 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6850    0.4001   -1.7006 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5848    1.0110   -0.2588 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0631   -0.0340    1.0857 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6594    1.0259    1.3372 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5146   -1.5712    0.5807 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0276   -0.2673    1.6740 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1825    0.1575   -1.1250 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4584    2.1825    1.0780 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4081    1.9975   -0.4741 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8616    0.8036    1.2190 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6401   -0.9593    1.4444 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4770   -1.4910    0.5482 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  2  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
  6 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  3 21  1  0
  3 22  1  0
  3 23  1  0
  4 24  1  0
  4 25  1  0
  4 26  1  0
  5 27  1  0
  5 28  1  0
  6 29  1  6
  7 30  1  0
  7 31  1  0
 14 32  1  0
 14 33  1  0
 17 34  1  0
M  CHG  2   2   1  10  -1
M  END

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    MOLECULE:                                                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  C   UNK     0      -1.691   5.184   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0      -1.691   3.644   0.000  0.00  0.00           N+1
HETATM    3  C   UNK     0      -3.231   3.644   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.151   3.644   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.691   2.104   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.357   1.334   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.357  -0.206   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.691  -0.976   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -3.025  -0.206   0.000  0.00  0.00           O-1
HETATM   10  O   UNK     0      -1.691  -2.516   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       0.976   2.104   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       2.310   1.334   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       2.310  -0.206   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       3.644   2.104   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.977   1.334   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       6.311   2.104   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       4.977  -0.206   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4    5                                             
CONECT    3    2                                                            
CONECT    4    2                                                            
CONECT    5    2    6                                                       
CONECT    6    5    7   11                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11    6   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   32    0
END

COMPND    HMDB0002095
HETATM    1  C1  UNL     1      -2.837  -1.914   0.506  1.00  0.00           C  
HETATM    2  N1  UNL     1      -2.282  -0.622   0.070  1.00  0.00           N1+
HETATM    3  C2  UNL     1      -2.337  -0.611  -1.372  1.00  0.00           C  
HETATM    4  C3  UNL     1      -3.183   0.392   0.575  1.00  0.00           C  
HETATM    5  C4  UNL     1      -0.963  -0.551   0.604  1.00  0.00           C  
HETATM    6  C5  UNL     1      -0.025   0.377  -0.077  1.00  0.00           C  
HETATM    7  C6  UNL     1      -0.436   1.827   0.025  1.00  0.00           C  
HETATM    8  C7  UNL     1       0.558   2.679  -0.680  1.00  0.00           C  
HETATM    9  O1  UNL     1       1.678   2.827  -0.110  1.00  0.00           O  
HETATM   10  O2  UNL     1       0.345   3.301  -1.883  1.00  0.00           O1-
HETATM   11  O3  UNL     1       1.225   0.280   0.624  1.00  0.00           O  
HETATM   12  C8  UNL     1       2.403  -0.043  -0.029  1.00  0.00           C  
HETATM   13  O4  UNL     1       2.305  -0.243  -1.275  1.00  0.00           O  
HETATM   14  C9  UNL     1       3.713  -0.150   0.684  1.00  0.00           C  
HETATM   15  C10 UNL     1       4.785  -0.499  -0.250  1.00  0.00           C  
HETATM   16  O5  UNL     1       4.513  -0.665  -1.465  1.00  0.00           O  
HETATM   17  O6  UNL     1       6.076  -0.635   0.252  1.00  0.00           O  
HETATM   18  H1  UNL     1      -3.928  -1.910   0.543  1.00  0.00           H  
HETATM   19  H2  UNL     1      -2.449  -2.104   1.542  1.00  0.00           H  
HETATM   20  H3  UNL     1      -2.413  -2.750  -0.113  1.00  0.00           H  
HETATM   21  H4  UNL     1      -3.116  -1.322  -1.729  1.00  0.00           H  
HETATM   22  H5  UNL     1      -1.392  -0.919  -1.848  1.00  0.00           H  
HETATM   23  H6  UNL     1      -2.685   0.400  -1.701  1.00  0.00           H  
HETATM   24  H7  UNL     1      -3.585   1.011  -0.259  1.00  0.00           H  
HETATM   25  H8  UNL     1      -4.063  -0.034   1.086  1.00  0.00           H  
HETATM   26  H9  UNL     1      -2.659   1.026   1.337  1.00  0.00           H  
HETATM   27  H10 UNL     1      -0.515  -1.571   0.581  1.00  0.00           H  
HETATM   28  H11 UNL     1      -1.028  -0.267   1.674  1.00  0.00           H  
HETATM   29  H12 UNL     1       0.183   0.158  -1.125  1.00  0.00           H  
HETATM   30  H13 UNL     1      -0.458   2.183   1.078  1.00  0.00           H  
HETATM   31  H14 UNL     1      -1.408   1.997  -0.474  1.00  0.00           H  
HETATM   32  H15 UNL     1       3.862   0.804   1.219  1.00  0.00           H  
HETATM   33  H16 UNL     1       3.640  -0.959   1.444  1.00  0.00           H  
HETATM   34  H17 UNL     1       6.477  -1.491   0.548  1.00  0.00           H  
CONECT    1    2   18   19   20
CONECT    2    3    4    5
CONECT    3   21   22   23
CONECT    4   24   25   26
CONECT    5    6   27   28
CONECT    6    7   11   29
CONECT    7    8   30   31
CONECT    8    9    9   10
CONECT   11   12
CONECT   12   13   13   14
CONECT   14   15   32   33
CONECT   15   16   16   17
CONECT   17   34
END

HMDB0002095
     RDKit          3D
Malonylcarnitine
 34 33  0  0  0  0  0  0  0  0999 V2000
   -2.8374   -1.9144    0.5063 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2819   -0.6223    0.0702 N   0  0  0  0  0  4  0  0  0  0  0  0
   -2.3372   -0.6107   -1.3722 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1831    0.3919    0.5752 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9633   -0.5515    0.6037 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0251    0.3774   -0.0771 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4357    1.8273    0.0251 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5582    2.6787   -0.6804 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6785    2.8272   -0.1099 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3449    3.3011   -1.8832 O   0  0  0  0  0  1  0  0  0  0  0  0
    1.2250    0.2798    0.6240 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4028   -0.0427   -0.0294 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3049   -0.2435   -1.2755 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7129   -0.1496    0.6836 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7853   -0.4987   -0.2499 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5125   -0.6646   -1.4654 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0758   -0.6350    0.2515 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9278   -1.9097    0.5433 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4485   -2.1041    1.5415 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4126   -2.7499   -0.1132 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1165   -1.3224   -1.7290 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3918   -0.9195   -1.8478 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6850    0.4001   -1.7006 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5848    1.0110   -0.2588 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0631   -0.0340    1.0857 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6594    1.0259    1.3372 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5146   -1.5712    0.5807 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0276   -0.2673    1.6740 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1825    0.1575   -1.1250 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4584    2.1825    1.0780 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4081    1.9975   -0.4741 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8616    0.8036    1.2190 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6401   -0.9593    1.4444 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4770   -1.4910    0.5482 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  2  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
  6 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  3 21  1  0
  3 22  1  0
  3 23  1  0
  4 24  1  0
  4 25  1  0
  4 26  1  0
  5 27  1  0
  5 28  1  0
  6 29  1  6
  7 30  1  0
  7 31  1  0
 14 32  1  0
 14 33  1  0
 17 34  1  0
M  CHG  2   2   1  10  -1
M  END

View in JSmol View NMR Assignments

Synonyms

Value	Source
Malonyl-carnitin	HMDB
Malonyl-carnitine	HMDB
Malonyl-L-carnitine	HMDB
O-Malonyl-L-carnitine	HMDB
O-Malonylcarnitine	HMDB
Malonylcarnitine	HMDB

Chemical Formula

C₁₀H₁₇NO₆

Average Mass

247.2470 Da

Monoisotopic Mass

247.10559 Da

IUPAC Name

(3R)-3-[(2-carboxyacetyl)oxy]-4-(trimethylazaniumyl)butanoate

Traditional Name

(3R)-3-[(2-carboxyacetyl)oxy]-4-(trimethylammonio)butanoate

CAS Registry Number

853728-01-5

SMILES

C[N+](C)(C)C[C@@H](CC([O-])=O)OC(=O)CC(O)=O

InChI Identifier

InChI=1S/C10H17NO6/c1-11(2,3)6-7(4-8(12)13)17-10(16)5-9(14)15/h7H,4-6H2,1-3H3,(H-,12,13,14,15)/t7-/m1/s1

InChI Key

ZGNBLKBZJBJFDG-SSDOTTSWSA-N

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	¹³C NMR Spectrum (1D, 252 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	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	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	¹³C NMR Spectrum (1D, 201 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

Species Name	Source	Reference
Anas platyrhynchos	FooDB	FooDB
Anatidae	FooDB	FooDB
Anser anser	FooDB	FooDB
Bison bison	FooDB	FooDB
Bos taurus	FooDB	FooDB
Bos taurus X Bison bison	FooDB	FooDB
Bubalus bubalis	FooDB	FooDB
Capra aegagrus hircus	FooDB	FooDB
Cervidae	FooDB	FooDB
Cervus canadensis	FooDB	FooDB
Columba	FooDB	FooDB
Columbidae	FooDB	FooDB
Dromaius novaehollandiae	FooDB	FooDB
Equus caballus	FooDB	FooDB
Gallus gallus	FooDB	FooDB
Lagopus muta	FooDB	FooDB
Leporidae	FooDB	FooDB
Lepus timidus	FooDB	FooDB
Melanitta fusca	FooDB	FooDB
Meleagris gallopavo	FooDB	FooDB
Numida meleagris	FooDB	FooDB
Odocoileus	FooDB	FooDB
Oryctolagus	FooDB	FooDB
Ovis aries	FooDB	FooDB
Phasianidae	FooDB	FooDB
Phasianus colchicus	FooDB	FooDB
Struthio camelus	FooDB	FooDB
Sus scrofa	FooDB	FooDB
Sus scrofa domestica	FooDB	FooDB

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as acyl carnitines. These are organic compounds containing a fatty acid with the carboxylic acid attached to carnitine through an ester bond.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acid esters

Direct Parent

Acyl carnitines

Alternative Parents

Substituents

Acyl-carnitine
Tricarboxylic acid or derivatives
1,3-dicarbonyl compound
Quaternary ammonium salt
Tetraalkylammonium salt
Carboxylic acid salt
Carboxylic acid ester
Carboxylic acid
Carboxylic acid derivative
Hydrocarbon derivative
Organic salt
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Organooxygen compound
Organonitrogen compound
Carbonyl group
Amine
Organic oxide
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

O-acyl-L-carnitine (CHEBI:85470 )

Physical Properties

State

Solid

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
Water Solubility	0.34 g/L	ALOGPS
logP	-2	ALOGPS
logP	-4.6	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	3.47	ChemAxon
pKa (Strongest Basic)	-7.2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	103.73 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	78.98 m³·mol⁻¹	ChemAxon
Polarizability	23.68 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

HMDB0002095

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB022843

KNApSAcK ID

Not Available

Chemspider ID

34999703

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

6484

PubChem Compound

91825606

PDB ID

Not Available

ChEBI ID

85470

Good Scents ID

Not Available

References

General References

Johnson DW, Trinh MU: Stability of malonylcarnitine and glutarylcarnitine in stored blood spots. J Inherit Metab Dis. 2004;27(6):789-90. [PubMed:15617193 ]
Santer R, Fingerhut R, Lassker U, Wightman PJ, Fitzpatrick DR, Olgemoller B, Roscher AA: Tandem mass spectrometric determination of malonylcarnitine: diagnosis and neonatal screening of malonyl-CoA decarboxylase deficiency. Clin Chem. 2003 Apr;49(4):660-2. [PubMed:12651823 ]
Napolitano N, Wiley V, Pitt JJ: Pseudo-glutarylcarnitinaemia in medium-chain acyl-CoA dehydrogenase deficiency detected by tandem mass spectrometry newborn screening. J Inherit Metab Dis. 2004;27(4):465-71. [PubMed:15303003 ]
Wolf A, Weir P, Segar P, Stone J, Shield J: Impaired fatty acid oxidation in propofol infusion syndrome. Lancet. 2001 Feb 24;357(9256):606-7. [PubMed:11558490 ]
Ficicioglu C, Chrisant MR, Payan I, Chace DH: Cardiomyopathy and hypotonia in a 5-month-old infant with malonyl-coa decarboxylase deficiency: potential for preclinical diagnosis with expanded newborn screening. Pediatr Cardiol. 2005 Nov-Dec;26(6):881-3. [PubMed:16078122 ]

Showing NP-Card for Malonylcarnitine (NP0001047)

MOL for NP0001047 (Malonylcarnitine)

3D MOL for NP0001047 (Malonylcarnitine)

3D SDF for NP0001047 (Malonylcarnitine)

3D-SDF for NP0001047 (Malonylcarnitine)

PDB for NP0001047 (Malonylcarnitine)

3D PDB for NP0001047 (Malonylcarnitine)

SMILES for NP0001047 (Malonylcarnitine)

INCHI for NP0001047 (Malonylcarnitine)

Structure for NP0001047 (Malonylcarnitine)

3D Structure for NP0001047 (Malonylcarnitine)