NP-MRD: Showing NP-Card for Isobutyryl-L-carnitine (NP0000271)

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Record Information

Version

2.0

Created at

2005-11-16 15:48:42 UTC

Updated at

2024-09-17 15:41:30 UTC

NP-MRD ID

NP0000271

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Isobutyryl-L-carnitine

Description

Isobutyryl-L-carnitine is a product of the acyl-CoA dehydrogenases (ACADs), which are a group of mitochondrial enzymes involved in the metabolism of fatty acids or branched-chain amino acids (OMIM: 600301 ). Isobutyryl-L-carnitine is a member of the class of compounds known as acyl carnitines. Acyl carnitines are organic compounds containing a fatty acid with the carboxylic acid attached to carnitine through an ester bond. Isobutyryl-L-carnitine is practically insoluble (in water) and a weakly acidic compound (based on its pKa).

Structure

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

NP0000271
     RDKit          3D

 37 36  0  0  0  0  0  0  0  0999 V2000
    4.4081    0.9318   -1.1530 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5048   -0.0908   -0.5456 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0059   -0.5757    0.7994 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1141    0.3977   -0.3719 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8439    1.5704   -0.7360 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0882   -0.3214    0.1548 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2517    0.1276    0.3355 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6778    0.0992    1.7657 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1297    0.9444    2.6648 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0758    1.6065    2.2205 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1786    0.9903    4.0046 O   0  0  0  0  0  1  0  0  0  0  0  0
   -1.1632   -0.6210   -0.5632 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5340   -0.3352   -0.5896 N   0  0  0  0  0  4  0  0  0  0  0  0
   -3.0519   -0.6161   -1.9602 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9865    0.9592   -0.2366 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2962   -1.2973    0.2255 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9009    1.9076   -1.2122 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3682    0.9975   -0.5732 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7182    0.6713   -2.1925 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5371   -0.9954   -1.2204 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6645   -1.6172    1.0163 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6185    0.0495    1.6389 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1133   -0.5361    0.8786 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2411    1.1806   -0.0036 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7052    0.5132    1.8184 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7850   -0.9396    2.1652 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7548   -0.4826   -1.6110 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9871   -1.7182   -0.3786 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4252   -0.0813   -2.6992 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1156   -0.3337   -2.0006 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9655   -1.6994   -2.1060 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6954    0.9913    0.6263 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1803    1.7370   -0.1614 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6230    1.3562   -1.0835 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3712   -1.0299    0.2071 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2178   -2.2714   -0.3331 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8842   -1.4690    1.2102 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
  4  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
  7 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 13 16  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  2 20  1  0
  3 21  1  0
  3 22  1  0
  3 23  1  0
  7 24  1  6
  8 25  1  0
  8 26  1  0
 12 27  1  0
 12 28  1  0
 14 29  1  0
 14 30  1  0
 14 31  1  0
 15 32  1  0
 15 33  1  0
 15 34  1  0
 16 35  1  0
 16 36  1  0
 16 37  1  0
M  CHG  2  11  -1  13   1
M  END


  Mrv1652307072020232D          

 16 15  0  0  0  0            999 V2000
   -1.3584   -0.1993    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6441   -0.6127    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0705   -0.1993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7845   -0.6127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4983   -0.1993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0705    0.6252    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3584    0.6252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0726    1.0358    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
   -2.7907    0.6231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0726    1.8610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9259    1.5288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0665   -0.6230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0665   -1.4475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3523   -1.8610    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   -2.7785   -1.8610    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7845   -1.4379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  7  1  6  0  0  0
  1 12  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3  6  2  0  0  0  0
  4  5  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
  8 11  1  0  0  0  0
 12 13  1  0  0  0  0
 13 15  2  0  0  0  0
 13 14  1  0  0  0  0
  4 16  1  0  0  0  0
M  CHG  2   8   1  14  -1
M  END
> <DATABASE_ID>
NP0000271

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C11H21NO4/c1-8(2)11(15)16-9(6-10(13)14)7-12(3,4)5/h8-9H,6-7H2,1-5H3/t9-/m1/s1

> <INCHI_KEY>
LRCNOZRCYBNMEP-SECBINFHSA-N

> <FORMULA>
C11H21NO4

> <MOLECULAR_WEIGHT>
231.292

> <EXACT_MASS>
231.14705816

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
37

> <JCHEM_AVERAGE_POLARIZABILITY>
24.64310573657653

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
-2.13

> <JCHEM_LOGP>
-3.202858512471745

> <ALOGPS_LOGS>
-3.69

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.268923893967359

> <JCHEM_PKA_STRONGEST_BASIC>
-7.089988723429431

> <JCHEM_POLAR_SURFACE_AREA>
66.43

> <JCHEM_REFRACTIVITY>
81.8382

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.79e-02 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

NP0000271
     RDKit          3D

 37 36  0  0  0  0  0  0  0  0999 V2000
    4.4081    0.9318   -1.1530 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5048   -0.0908   -0.5456 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0059   -0.5757    0.7994 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1141    0.3977   -0.3719 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8439    1.5704   -0.7360 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0882   -0.3214    0.1548 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2517    0.1276    0.3355 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6778    0.0992    1.7657 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1297    0.9444    2.6648 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0758    1.6065    2.2205 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1786    0.9903    4.0046 O   0  0  0  0  0  1  0  0  0  0  0  0
   -1.1632   -0.6210   -0.5632 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5340   -0.3352   -0.5896 N   0  0  0  0  0  4  0  0  0  0  0  0
   -3.0519   -0.6161   -1.9602 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9865    0.9592   -0.2366 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2962   -1.2973    0.2255 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9009    1.9076   -1.2122 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3682    0.9975   -0.5732 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7182    0.6713   -2.1925 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5371   -0.9954   -1.2204 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6645   -1.6172    1.0163 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6185    0.0495    1.6389 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1133   -0.5361    0.8786 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2411    1.1806   -0.0036 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7052    0.5132    1.8184 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7850   -0.9396    2.1652 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7548   -0.4826   -1.6110 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9871   -1.7182   -0.3786 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4252   -0.0813   -2.6992 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1156   -0.3337   -2.0006 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9655   -1.6994   -2.1060 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6954    0.9913    0.6263 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1803    1.7370   -0.1614 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6230    1.3562   -1.0835 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3712   -1.0299    0.2071 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2178   -2.2714   -0.3331 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8842   -1.4690    1.2102 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
  4  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
  7 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 13 16  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  2 20  1  0
  3 21  1  0
  3 22  1  0
  3 23  1  0
  7 24  1  6
  8 25  1  0
  8 26  1  0
 12 27  1  0
 12 28  1  0
 14 29  1  0
 14 30  1  0
 14 31  1  0
 15 32  1  0
 15 33  1  0
 15 34  1  0
 16 35  1  0
 16 36  1  0
 16 37  1  0
M  CHG  2  11  -1  13   1
M  END

HEADER    PROTEIN                                 07-JUL-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-JUL-20         0                                  
HETATM    1  C   UNK     0      -2.536  -0.372   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -1.202  -1.144   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       0.132  -0.372   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.464  -1.144   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.797  -0.372   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       0.132   1.167   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      -2.536   1.167   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0      -3.869   1.934   0.000  0.00  0.00           N+1
HETATM    9  C   UNK     0      -5.209   1.163   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -3.869   3.474   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -5.462   2.854   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -3.857  -1.163   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -3.857  -2.702   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -2.524  -3.474   0.000  0.00  0.00           O-1
HETATM   15  O   UNK     0      -5.187  -3.474   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       1.464  -2.684   0.000  0.00  0.00           C+0
CONECT    1    2    7   12                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4    6                                                  
CONECT    4    3    5   16                                                  
CONECT    5    4                                                            
CONECT    6    3                                                            
CONECT    7    1    8                                                       
CONECT    8    7    9   10   11                                             
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11    8                                                            
CONECT   12    1   13                                                       
CONECT   13   12   15   14                                                  
CONECT   14   13                                                            
CONECT   15   13                                                            
CONECT   16    4                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   30    0
END

COMPND    NP0000271
HETATM    1  C1  UNL     1       4.408   0.932  -1.153  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.505  -0.091  -0.546  1.00  0.00           C  
HETATM    3  C3  UNL     1       4.006  -0.576   0.799  1.00  0.00           C  
HETATM    4  C4  UNL     1       2.114   0.398  -0.372  1.00  0.00           C  
HETATM    5  O1  UNL     1       1.844   1.570  -0.736  1.00  0.00           O  
HETATM    6  O2  UNL     1       1.088  -0.321   0.155  1.00  0.00           O  
HETATM    7  C5  UNL     1      -0.252   0.128   0.335  1.00  0.00           C  
HETATM    8  C6  UNL     1      -0.678   0.099   1.766  1.00  0.00           C  
HETATM    9  C7  UNL     1       0.130   0.944   2.665  1.00  0.00           C  
HETATM   10  O3  UNL     1       1.076   1.607   2.220  1.00  0.00           O  
HETATM   11  O4  UNL     1      -0.179   0.990   4.005  1.00  0.00           O1-
HETATM   12  C8  UNL     1      -1.163  -0.621  -0.563  1.00  0.00           C  
HETATM   13  N1  UNL     1      -2.534  -0.335  -0.590  1.00  0.00           N1+
HETATM   14  C9  UNL     1      -3.052  -0.616  -1.960  1.00  0.00           C  
HETATM   15  C10 UNL     1      -2.986   0.959  -0.237  1.00  0.00           C  
HETATM   16  C11 UNL     1      -3.296  -1.297   0.225  1.00  0.00           C  
HETATM   17  H1  UNL     1       3.901   1.908  -1.212  1.00  0.00           H  
HETATM   18  H2  UNL     1       5.368   0.998  -0.573  1.00  0.00           H  
HETATM   19  H3  UNL     1       4.718   0.671  -2.193  1.00  0.00           H  
HETATM   20  H4  UNL     1       3.537  -0.995  -1.220  1.00  0.00           H  
HETATM   21  H5  UNL     1       3.665  -1.617   1.016  1.00  0.00           H  
HETATM   22  H6  UNL     1       3.619   0.050   1.639  1.00  0.00           H  
HETATM   23  H7  UNL     1       5.113  -0.536   0.879  1.00  0.00           H  
HETATM   24  H8  UNL     1      -0.241   1.181  -0.004  1.00  0.00           H  
HETATM   25  H9  UNL     1      -1.705   0.513   1.818  1.00  0.00           H  
HETATM   26  H10 UNL     1      -0.785  -0.940   2.165  1.00  0.00           H  
HETATM   27  H11 UNL     1      -0.755  -0.483  -1.611  1.00  0.00           H  
HETATM   28  H12 UNL     1      -0.987  -1.718  -0.379  1.00  0.00           H  
HETATM   29  H13 UNL     1      -2.425  -0.081  -2.699  1.00  0.00           H  
HETATM   30  H14 UNL     1      -4.116  -0.334  -2.001  1.00  0.00           H  
HETATM   31  H15 UNL     1      -2.965  -1.699  -2.106  1.00  0.00           H  
HETATM   32  H16 UNL     1      -3.695   0.991   0.626  1.00  0.00           H  
HETATM   33  H17 UNL     1      -2.180   1.737  -0.161  1.00  0.00           H  
HETATM   34  H18 UNL     1      -3.623   1.356  -1.083  1.00  0.00           H  
HETATM   35  H19 UNL     1      -4.371  -1.030   0.207  1.00  0.00           H  
HETATM   36  H20 UNL     1      -3.218  -2.271  -0.333  1.00  0.00           H  
HETATM   37  H21 UNL     1      -2.884  -1.469   1.210  1.00  0.00           H  
CONECT    1    2   17   18   19
CONECT    2    3    4   20
CONECT    3   21   22   23
CONECT    4    5    5    6
CONECT    6    7
CONECT    7    8   12   24
CONECT    8    9   25   26
CONECT    9   10   10   11
CONECT   12   13   27   28
CONECT   13   14   15   16
CONECT   14   29   30   31
CONECT   15   32   33   34
CONECT   16   35   36   37
END

NP0000271
     RDKit          3D

37 36  0  0  0  0  0  0  0  0999 V2000
    4.4081    0.9318   -1.1530 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5048   -0.0908   -0.5456 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0059   -0.5757    0.7994 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1141    0.3977   -0.3719 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8439    1.5704   -0.7360 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0882   -0.3214    0.1548 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2517    0.1276    0.3355 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6778    0.0992    1.7657 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1297    0.9444    2.6648 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0758    1.6065    2.2205 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1786    0.9903    4.0046 O   0  0  0  0  0  1  0  0  0  0  0  0
   -1.1632   -0.6210   -0.5632 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5340   -0.3352   -0.5896 N   0  0  0  0  0  4  0  0  0  0  0  0
   -3.0519   -0.6161   -1.9602 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9865    0.9592   -0.2366 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2962   -1.2973    0.2255 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9009    1.9076   -1.2122 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3682    0.9975   -0.5732 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7182    0.6713   -2.1925 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5371   -0.9954   -1.2204 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6645   -1.6172    1.0163 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6185    0.0495    1.6389 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1133   -0.5361    0.8786 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2411    1.1806   -0.0036 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7052    0.5132    1.8184 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7850   -0.9396    2.1652 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7548   -0.4826   -1.6110 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9871   -1.7182   -0.3786 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4252   -0.0813   -2.6992 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1156   -0.3337   -2.0006 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9655   -1.6994   -2.1060 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6954    0.9913    0.6263 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1803    1.7370   -0.1614 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6230    1.3562   -1.0835 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3712   -1.0299    0.2071 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2178   -2.2714   -0.3331 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8842   -1.4690    1.2102 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
  4  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
  7 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 13 16  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  2 20  1  0
  3 21  1  0
  3 22  1  0
  3 23  1  0
  7 24  1  6
  8 25  1  0
  8 26  1  0
 12 27  1  0
 12 28  1  0
 14 29  1  0
 14 30  1  0
 14 31  1  0
 15 32  1  0
 15 33  1  0
 15 34  1  0
 16 35  1  0
 16 36  1  0
 16 37  1  0
M  CHG  2  11  -1  13   1
M  END

View in JSmol View NMR Assignments

Synonyms

Value	Source
(R)-Isobutyrylcarnitine	ChEBI
Iso-butyryl-L(-)-carnitin	ChEBI
Isobutyryl-carnitine	ChEBI
Isobutyryl-L-(-)-carnitine	ChEBI
O-Isobutanoyl-(R)-carnitine	ChEBI
Isobutyryl-1-carnitine	HMDB
Isobutyrylcarnitine	HMDB
O-Isobutyryl-L-carnitine	HMDB
Isobutyryl-L-carnitine	HMDB, ChEBI

Chemical Formula

C₁₁H₂₁NO₄

Average Mass

231.2920 Da

Monoisotopic Mass

231.14706 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

25518-49-4

SMILES

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

InChI Identifier

InChI=1S/C11H21NO4/c1-8(2)11(15)16-9(6-10(13)14)7-12(3,4)5/h8-9H,6-7H2,1-5H3/t9-/m1/s1

InChI Key

LRCNOZRCYBNMEP-SECBINFHSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

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
Branched fatty acid
Dicarboxylic acid or derivatives
Tetraalkylammonium salt
Quaternary ammonium salt
Carboxylic acid ester
Carboxylic acid salt
Carboxylic acid derivative
Carboxylic acid
Organonitrogen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic nitrogen compound
Carbonyl group
Organic oxygen compound
Amine
Organooxygen compound
Organic salt
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

O-acyl-L-carnitine (CHEBI:84838 )
O-isobutyrylcarnitine (CHEBI:84838 )

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	0.058 g/L	ALOGPS
logP	-2.1	ALOGPS
logP	-3.2	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	4.27	ChemAxon
pKa (Strongest Basic)	-7.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	66.43 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	81.84 m³·mol⁻¹	ChemAxon
Polarizability	24.64 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

HMDB0000736

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB022213

KNApSAcK ID

Not Available

Chemspider ID

147286

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

5704

PubChem Compound

168379

PDB ID

Not Available

ChEBI ID

84838

Good Scents ID

Not Available

References

General References

Kidouchi K, Niwa T, Nohara D, Asai K, Sugiyama N, Morishita H, Kobayashi M, Wada Y: Urinary acylcarnitines in a patient with neonatal multiple acyl-CoA dehydrogenation deficiency, quantified by a carboxylic acid analyzer with a reversed-phase column. Clin Chim Acta. 1988 Apr 29;173(3):263-72. [PubMed:3383426 ]
Roe CR, Cederbaum SD, Roe DS, Mardach R, Galindo A, Sweetman L: Isolated isobutyryl-CoA dehydrogenase deficiency: an unrecognized defect in human valine metabolism. Mol Genet Metab. 1998 Dec;65(4):264-71. [PubMed:9889013 ]
Vallee L, Fontaine M, Nuyts JP, Ricart G, Krivosic I, Divry P, Vianey-Saban C, Lhermitte M, Vamecq J: Stroke, hemiparesis and deficient mitochondrial beta-oxidation. Eur J Pediatr. 1994 Aug;153(8):598-603. [PubMed:7957409 ]
Sugiyama N, Kidouchi K, Kobayashi M, Wada Y: Carnitine deficiency in inherited organic acid disorders and Reye syndrome. Acta Paediatr Jpn. 1990 Aug;32(4):410-6. [PubMed:2288224 ]
Koeberl DD, Young SP, Gregersen NS, Vockley J, Smith WE, Benjamin DK Jr, An Y, Weavil SD, Chaing SH, Bali D, McDonald MT, Kishnani PS, Chen YT, Millington DS: Rare disorders of metabolism with elevated butyryl- and isobutyryl-carnitine detected by tandem mass spectrometry newborn screening. Pediatr Res. 2003 Aug;54(2):219-23. Epub 2003 May 7. [PubMed:12736383 ]
Matsumoto K, Takahashi M, Takiyama N, Misaki H, Matsuo N, Murano S, Yuki H: Enzyme reactor for urinary acylcarnitines assay by reversed-phase high-performance liquid chromatography. Clin Chim Acta. 1993 Jul 16;216(1-2):135-43. [PubMed:8222264 ]
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Showing NP-Card for Isobutyryl-L-carnitine (NP0000271)

MOL for NP0000271 (Isobutyryl-L-carnitine)

3D MOL for NP0000271 (Isobutyryl-L-carnitine)

3D SDF for NP0000271 (Isobutyryl-L-carnitine)

3D-SDF for NP0000271 (Isobutyryl-L-carnitine)

PDB for NP0000271 (Isobutyryl-L-carnitine)

3D PDB for NP0000271 (Isobutyryl-L-carnitine)

SMILES for NP0000271 (Isobutyryl-L-carnitine)

INCHI for NP0000271 (Isobutyryl-L-carnitine)

Structure for NP0000271 (Isobutyryl-L-carnitine)

3D Structure for NP0000271 (Isobutyryl-L-carnitine)