NP-MRD: Showing NP-Card for 2-Methylbutyroylcarnitine (NP0001258)

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Record Information

Version

1.0

Created at

2005-11-16 15:48:42 UTC

Updated at

2020-11-24 22:22:02 UTC

NP-MRD ID

NP0001258

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-Methylbutyroylcarnitine

Description

2-Methylbutyroylcarnitine is a member of the class of compounds known as acylcarnitines. Acylcarnitines are organic compounds containing a fatty acid with the carboxylic acid attached to carnitine through an ester bond. Thus, 2-Methylbutyroylcarnitine is considered to be a fatty ester lipid molecule. 2-Methylbutyroylcarnitine is practically insoluble (in water) and a weakly acidic compound (based on its pKa). 2-Methylbutyroylcarnitine can be found in urine. Within the cell, 2-Methylbutyroylcarnitine is primarily located in the membrane (predicted from logP). It can also be found in the extracellular space. Usually not detected in normal individuals, the elevation of 2-methylbutyrylcarnitine suggests a deficiency of a dehydrogenase specific for isobutyryl-CoA, important in the differential diagnosis of branched chain organic acidurias by analysis of urinary organic acids and acylcarnitines in plasma or dried blood spots (The Metabolic and Molecular Bases of Inherited Disease, Chapter 93).

Structure

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

HMDB0000378
     RDKit          3D
2-Methylbutyroylcarnitine
 40 39  0  0  0  0  0  0  0  0999 V2000
    3.8272    2.3739   -0.0034 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6710    1.4507   -0.3578 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7721    0.2427    0.5122 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1237   -0.4077    0.2154 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6665   -0.7293    0.3328 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8822   -1.9273   -0.0371 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3415   -0.4549    0.5380 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7193   -1.3863    0.3675 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4271   -1.7139    1.6204 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5203   -2.6932    1.4567 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8729   -3.2749    0.4249 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2788   -3.0303    2.6033 O   0  0  0  0  0  1  0  0  0  0  0  0
   -1.5506   -0.9783   -0.8085 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1799    0.2800   -0.7574 N   0  0  0  0  0  4  0  0  0  0  0  0
   -1.3733    1.3459   -0.2161 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4269    0.6809   -2.1587 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5022    0.2508   -0.1340 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5485    3.4299   -0.2057 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7214    2.1636   -0.6384 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0502    2.3182    1.0816 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7375    2.0190   -0.0800 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6395    1.2424   -1.4253 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7750    0.5457    1.5727 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4088   -0.2810   -0.8509 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9137    0.0193    0.8467 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0860   -1.5064    0.4177 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2067   -2.3151    0.0484 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6761   -2.2258    2.2948 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8640   -0.8440    2.1512 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2423   -1.7522   -1.1267 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7973   -0.9177   -1.6617 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4422    1.3934   -0.8424 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1843    1.2836    0.8521 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8602    2.3465   -0.3909 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1504    1.5099   -2.1849 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4376    1.0054   -2.5427 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8321   -0.1438   -2.7520 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9443   -0.7705   -0.3283 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4731    0.4934    0.9351 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2028    0.9572   -0.6202 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  3  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
  8 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
 14 17  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  2 21  1  0
  2 22  1  0
  3 23  1  0
  4 24  1  0
  4 25  1  0
  4 26  1  0
  8 27  1  0
  9 28  1  0
  9 29  1  0
 13 30  1  0
 13 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
 17 38  1  0
 17 39  1  0
 17 40  1  0
M  CHG  2  12  -1  14   1
M  END

HMDB00378.mol
  Mrv1652305261923542D          

 17 16  0  0  0  0            999 V2000
   -1.0717    0.4125    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
   -0.3572    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3572    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3572    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0717    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0717   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3572   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3572   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3572   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3572   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7862   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7862    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6020    1.0445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5414    1.0445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0717    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7862    1.2375    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    1.0717    2.4750    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
  3  4  1  0  0  0  0
  3  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
  7 10  1  0  0  0  0
  6 11  2  0  0  0  0
  1 12  1  0  0  0  0
  1 13  1  0  0  0  0
  1 14  1  0  0  0  0
  4 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  2  0  0  0  0
M  CHG  2   1   1  16  -1
M  END
> <DATABASE_ID>
NP0001258

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C12H23NO4/c1-6-9(2)12(16)17-10(7-11(14)15)8-13(3,4)5/h9-10H,6-8H2,1-5H3

> <INCHI_KEY>
IHCPDBBYTYJYIL-UHFFFAOYSA-N

> <FORMULA>
C12H23NO4

> <MOLECULAR_WEIGHT>
245.3153

> <EXACT_MASS>
245.162708229

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
40

> <JCHEM_AVERAGE_POLARIZABILITY>
26.514293565015066

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
-2.00

> <JCHEM_LOGP>
-2.758289847471746

> <ALOGPS_LOGS>
-4.07

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.342854307487348

> <JCHEM_PKA_STRONGEST_BASIC>
-7.092942553084254

> <JCHEM_POLAR_SURFACE_AREA>
66.43

> <JCHEM_REFRACTIVITY>
86.4392

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.54e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-methylbutyroylcarnitine

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0000378
     RDKit          3D
2-Methylbutyroylcarnitine
 40 39  0  0  0  0  0  0  0  0999 V2000
    3.8272    2.3739   -0.0034 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6710    1.4507   -0.3578 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7721    0.2427    0.5122 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1237   -0.4077    0.2154 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6665   -0.7293    0.3328 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8822   -1.9273   -0.0371 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3415   -0.4549    0.5380 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7193   -1.3863    0.3675 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4271   -1.7139    1.6204 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5203   -2.6932    1.4567 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8729   -3.2749    0.4249 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2788   -3.0303    2.6033 O   0  0  0  0  0  1  0  0  0  0  0  0
   -1.5506   -0.9783   -0.8085 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1799    0.2800   -0.7574 N   0  0  0  0  0  4  0  0  0  0  0  0
   -1.3733    1.3459   -0.2161 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4269    0.6809   -2.1587 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5022    0.2508   -0.1340 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5485    3.4299   -0.2057 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7214    2.1636   -0.6384 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0502    2.3182    1.0816 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7375    2.0190   -0.0800 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6395    1.2424   -1.4253 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7750    0.5457    1.5727 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4088   -0.2810   -0.8509 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9137    0.0193    0.8467 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0860   -1.5064    0.4177 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2067   -2.3151    0.0484 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6761   -2.2258    2.2948 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8640   -0.8440    2.1512 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2423   -1.7522   -1.1267 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7973   -0.9177   -1.6617 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4422    1.3934   -0.8424 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1843    1.2836    0.8521 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8602    2.3465   -0.3909 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1504    1.5099   -2.1849 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4376    1.0054   -2.5427 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8321   -0.1438   -2.7520 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9443   -0.7705   -0.3283 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4731    0.4934    0.9351 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2028    0.9572   -0.6202 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  3  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
  8 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
 14 17  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  2 21  1  0
  2 22  1  0
  3 23  1  0
  4 24  1  0
  4 25  1  0
  4 26  1  0
  8 27  1  0
  9 28  1  0
  9 29  1  0
 13 30  1  0
 13 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
 17 38  1  0
 17 39  1  0
 17 40  1  0
M  CHG  2  12  -1  14   1
M  END

HEADER    PROTEIN                                 26-MAY-19   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: HMDB00378.mol                                     
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-MAY-19         0                                  
HETATM    1  N   UNK     0      -2.001   0.770   0.000  0.00  0.00           N+1
HETATM    2  C   UNK     0      -0.667   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.667   0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.667   2.310   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       2.001   0.000   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       2.001  -1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.667  -2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.667  -3.850   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.667  -4.620   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.667  -1.540   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       3.334  -2.310   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -3.334   0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.990   1.950   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.011   1.950   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.001   3.080   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       3.334   2.310   0.000  0.00  0.00           O-1
HETATM   17  O   UNK     0       2.001   4.620   0.000  0.00  0.00           O+0
CONECT    1    2   12   13   14                                             
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3   15                                                       
CONECT    5    3    6                                                       
CONECT    6    5    7   11                                                  
CONECT    7    6    8   10                                                  
CONECT    8    7    9                                                       
CONECT    9    8                                                            
CONECT   10    7                                                            
CONECT   11    6                                                            
CONECT   12    1                                                            
CONECT   13    1                                                            
CONECT   14    1                                                            
CONECT   15    4   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   32    0
END

COMPND    HMDB0000378
HETATM    1  C1  UNL     1       3.827   2.374  -0.003  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.671   1.451  -0.358  1.00  0.00           C  
HETATM    3  C3  UNL     1       2.772   0.243   0.512  1.00  0.00           C  
HETATM    4  C4  UNL     1       4.124  -0.408   0.215  1.00  0.00           C  
HETATM    5  C5  UNL     1       1.667  -0.729   0.333  1.00  0.00           C  
HETATM    6  O1  UNL     1       1.882  -1.927  -0.037  1.00  0.00           O  
HETATM    7  O2  UNL     1       0.342  -0.455   0.538  1.00  0.00           O  
HETATM    8  C6  UNL     1      -0.719  -1.386   0.368  1.00  0.00           C  
HETATM    9  C7  UNL     1      -1.427  -1.714   1.620  1.00  0.00           C  
HETATM   10  C8  UNL     1      -2.520  -2.693   1.457  1.00  0.00           C  
HETATM   11  O3  UNL     1      -2.873  -3.275   0.425  1.00  0.00           O  
HETATM   12  O4  UNL     1      -3.279  -3.030   2.603  1.00  0.00           O1-
HETATM   13  C9  UNL     1      -1.551  -0.978  -0.808  1.00  0.00           C  
HETATM   14  N1  UNL     1      -2.180   0.280  -0.757  1.00  0.00           N1+
HETATM   15  C10 UNL     1      -1.373   1.346  -0.216  1.00  0.00           C  
HETATM   16  C11 UNL     1      -2.427   0.681  -2.159  1.00  0.00           C  
HETATM   17  C12 UNL     1      -3.502   0.251  -0.134  1.00  0.00           C  
HETATM   18  H1  UNL     1       3.548   3.430  -0.206  1.00  0.00           H  
HETATM   19  H2  UNL     1       4.721   2.164  -0.638  1.00  0.00           H  
HETATM   20  H3  UNL     1       4.050   2.318   1.082  1.00  0.00           H  
HETATM   21  H4  UNL     1       1.738   2.019  -0.080  1.00  0.00           H  
HETATM   22  H5  UNL     1       2.639   1.242  -1.425  1.00  0.00           H  
HETATM   23  H6  UNL     1       2.775   0.546   1.573  1.00  0.00           H  
HETATM   24  H7  UNL     1       4.409  -0.281  -0.851  1.00  0.00           H  
HETATM   25  H8  UNL     1       4.914   0.019   0.847  1.00  0.00           H  
HETATM   26  H9  UNL     1       4.086  -1.506   0.418  1.00  0.00           H  
HETATM   27  H10 UNL     1      -0.207  -2.315   0.048  1.00  0.00           H  
HETATM   28  H11 UNL     1      -0.676  -2.226   2.295  1.00  0.00           H  
HETATM   29  H12 UNL     1      -1.864  -0.844   2.151  1.00  0.00           H  
HETATM   30  H13 UNL     1      -2.242  -1.752  -1.127  1.00  0.00           H  
HETATM   31  H14 UNL     1      -0.797  -0.918  -1.662  1.00  0.00           H  
HETATM   32  H15 UNL     1      -0.442   1.393  -0.842  1.00  0.00           H  
HETATM   33  H16 UNL     1      -1.184   1.284   0.852  1.00  0.00           H  
HETATM   34  H17 UNL     1      -1.860   2.347  -0.391  1.00  0.00           H  
HETATM   35  H18 UNL     1      -3.150   1.510  -2.185  1.00  0.00           H  
HETATM   36  H19 UNL     1      -1.438   1.005  -2.543  1.00  0.00           H  
HETATM   37  H20 UNL     1      -2.832  -0.144  -2.752  1.00  0.00           H  
HETATM   38  H21 UNL     1      -3.944  -0.770  -0.328  1.00  0.00           H  
HETATM   39  H22 UNL     1      -3.473   0.493   0.935  1.00  0.00           H  
HETATM   40  H23 UNL     1      -4.203   0.957  -0.620  1.00  0.00           H  
CONECT    1    2   18   19   20
CONECT    2    3   21   22
CONECT    3    4    5   23
CONECT    4   24   25   26
CONECT    5    6    6    7
CONECT    7    8
CONECT    8    9   13   27
CONECT    9   10   28   29
CONECT   10   11   11   12
CONECT   13   14   30   31
CONECT   14   15   16   17
CONECT   15   32   33   34
CONECT   16   35   36   37
CONECT   17   38   39   40
END

HMDB0000378
     RDKit          3D
2-Methylbutyroylcarnitine
 40 39  0  0  0  0  0  0  0  0999 V2000
    3.8272    2.3739   -0.0034 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6710    1.4507   -0.3578 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7721    0.2427    0.5122 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1237   -0.4077    0.2154 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6665   -0.7293    0.3328 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8822   -1.9273   -0.0371 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3415   -0.4549    0.5380 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7193   -1.3863    0.3675 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4271   -1.7139    1.6204 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5203   -2.6932    1.4567 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8729   -3.2749    0.4249 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2788   -3.0303    2.6033 O   0  0  0  0  0  1  0  0  0  0  0  0
   -1.5506   -0.9783   -0.8085 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1799    0.2800   -0.7574 N   0  0  0  0  0  4  0  0  0  0  0  0
   -1.3733    1.3459   -0.2161 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4269    0.6809   -2.1587 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5022    0.2508   -0.1340 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5485    3.4299   -0.2057 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7214    2.1636   -0.6384 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0502    2.3182    1.0816 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7375    2.0190   -0.0800 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6395    1.2424   -1.4253 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7750    0.5457    1.5727 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4088   -0.2810   -0.8509 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9137    0.0193    0.8467 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0860   -1.5064    0.4177 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2067   -2.3151    0.0484 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6761   -2.2258    2.2948 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8640   -0.8440    2.1512 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2423   -1.7522   -1.1267 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7973   -0.9177   -1.6617 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4422    1.3934   -0.8424 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1843    1.2836    0.8521 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8602    2.3465   -0.3909 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1504    1.5099   -2.1849 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4376    1.0054   -2.5427 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8321   -0.1438   -2.7520 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9443   -0.7705   -0.3283 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4731    0.4934    0.9351 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2028    0.9572   -0.6202 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  3  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
  8 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
 14 17  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  2 21  1  0
  2 22  1  0
  3 23  1  0
  4 24  1  0
  4 25  1  0
  4 26  1  0
  8 27  1  0
  9 28  1  0
  9 29  1  0
 13 30  1  0
 13 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
 17 38  1  0
 17 39  1  0
 17 40  1  0
M  CHG  2  12  -1  14   1
M  END

View in JSmol

Synonyms

Value	Source
3-[(2-Methylbutanoyl)oxy]-4-(trimethylammonio)butanoate	ChEBI
3-[(2-Methylbutanoyl)oxy]-4-(trimethylammonio)butanoic acid	Generator
(2-Methylbutyryl)carnitine	HMDB
L-2-Methylbutyrate (3-carboxy-2-hydroxypropyl)trimethyl-hydroxide ammonium inner salt	HMDB
Methylbutyroyl-carnitine	HMDB

Chemical Formula

C₁₂H₂₃NO₄

Average Mass

245.3153 Da

Monoisotopic Mass

245.16271 Da

IUPAC Name

3-[(2-methylbutanoyl)oxy]-4-(trimethylazaniumyl)butanoate

Traditional Name

2-methylbutyroylcarnitine

CAS Registry Number

31023-25-3

SMILES

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

InChI Identifier

InChI=1S/C12H23NO4/c1-6-9(2)12(16)17-10(7-11(14)15)8-13(3,4)5/h9-10H,6-8H2,1-5H3

InChI Key

IHCPDBBYTYJYIL-UHFFFAOYSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
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

Not Available

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

C5-acylcarnitine (CHEBI:73026 )

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	0.025 g/L	ALOGPS
logP	-2	ALOGPS
logP	-2.8	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Acidic)	4.34	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	8	ChemAxon
Refractivity	86.44 m³·mol⁻¹	ChemAxon
Polarizability	26.51 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

HMDB0000378

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB021996

KNApSAcK ID

Not Available

Chemspider ID

4932320

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

5367

PubChem Compound

6426901

PDB ID

Not Available

ChEBI ID

73026

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 ]
Salamino F, Di Lisa F, Burlina AB, Menabo R, Barbato R, De Tullio R, Siliprandi N: Involvement of erythrocyte calpain in glycine- and carnitine-treated isovaleric acidemia. Pediatr Res. 1994 Aug;36(2):182-6. [PubMed:7970932 ]
Abdenur JE, Chamoles NA, Guinle AE, Schenone AB, Fuertes AN: Diagnosis of isovaleric acidaemia by tandem mass spectrometry: false positive result due to pivaloylcarnitine in a newborn screening programme. J Inherit Metab Dis. 1998 Aug;21(6):624-30. [PubMed:9762597 ]
Fries MH, Rinaldo P, Schmidt-Sommerfeld E, Jurecki E, Packman S: Isovaleric acidemia: response to a leucine load after three weeks of supplementation with glycine, L-carnitine, and combined glycine-carnitine therapy. J Pediatr. 1996 Sep;129(3):449-52. [PubMed:8804338 ]
Millington DS, Roe CR, Maltby DA, Inoue F: Endogenous catabolism is the major source of toxic metabolites in isovaleric acidemia. J Pediatr. 1987 Jan;110(1):56-60. [PubMed:3794887 ]
Minkler PE, Ingalls ST, Hoppel CL: High-performance liquid chromatographic separation of acylcarnitines following derivatization with 4'-bromophenacyl trifluoromethanesulfonate. Anal Biochem. 1990 Feb 15;185(1):29-35. [PubMed:2344045 ]
Chalmers RA, Roe CR, Stacey TE, Hoppel CL: Urinary excretion of l-carnitine and acylcarnitines by patients with disorders of organic acid metabolism: evidence for secondary insufficiency of l-carnitine. Pediatr Res. 1984 Dec;18(12):1325-8. [PubMed:6441143 ]
Roe CR, Millington DS, Maltby DA, Kahler SG, Bohan TP: L-carnitine therapy in isovaleric acidemia. J Clin Invest. 1984 Dec;74(6):2290-5. [PubMed:6549017 ]
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 ]
Sakuma T, Sugiyama N, Ichiki T, Kobayashi M, Wada Y, Nohara D: Analysis of acylcarnitines in maternal urine for prenatal diagnosis of glutaric aciduria type 2. Prenat Diagn. 1991 Feb;11(2):77-82. [PubMed:2062823 ]
Matern D, He M, Berry SA, Rinaldo P, Whitley CB, Madsen PP, van Calcar SC, Lussky RC, Andresen BS, Wolff JA, Vockley J: Prospective diagnosis of 2-methylbutyryl-CoA dehydrogenase deficiency in the Hmong population by newborn screening using tandem mass spectrometry. Pediatrics. 2003 Jul;112(1 Pt 1):74-8. [PubMed:12837870 ]
Pontremoli S, Melloni E, Michetti M, Sparatore B, Salamino F, Siliprandi N, Horecker BL: Isovalerylcarnitine is a specific activator of calpain of human neutrophils. Biochem Biophys Res Commun. 1987 Nov 13;148(3):1189-95. [PubMed:2825678 ]
Ferrara F, Bertelli A, Falchi M: Evaluation of carnitine, acetylcarnitine and isovalerylcarnitine on immune function and apoptosis. Drugs Exp Clin Res. 2005;31(3):109-14. [PubMed:16033249 ]
Bene J, Komlosi K, Havasi V, Talian G, Gasztonyi B, Horvath K, Mozsik G, Hunyady B, Melegh B, Figler M: Changes of plasma fasting carnitine ester profile in patients with ulcerative colitis. World J Gastroenterol. 2006 Jan 7;12(1):110-3. [PubMed:16440427 ]
Fontaine M, Briand G, Vallee L, Ricart G, Degand P, Divry P, Vianey-Saban C, Vamecq J: Acylcarnitine removal in a patient with acyl-CoA beta-oxidation deficiency disorder: effect of L-carnitine therapy and starvation. Clin Chim Acta. 1996 Aug 30;252(2):109-22. [PubMed:8853559 ]
Shigematsu Y, Kikawa Y, Sudo M, Kanaoka H, Fujioka M, Dan M: Prenatal diagnosis of isovaleric acidemia by fast atom bombardment and tandem mass spectrometry. Clin Chim Acta. 1991 Dec 16;203(2-3):369-74. [PubMed:1777996 ]

Showing NP-Card for 2-Methylbutyroylcarnitine (NP0001258)

MOL for NP0001258 (2-Methylbutyroylcarnitine)

3D MOL for NP0001258 (2-Methylbutyroylcarnitine)

3D SDF for NP0001258 (2-Methylbutyroylcarnitine)

3D-SDF for NP0001258 (2-Methylbutyroylcarnitine)

PDB for NP0001258 (2-Methylbutyroylcarnitine)

3D PDB for NP0001258 (2-Methylbutyroylcarnitine)

SMILES for NP0001258 (2-Methylbutyroylcarnitine)

INCHI for NP0001258 (2-Methylbutyroylcarnitine)

Structure for NP0001258 (2-Methylbutyroylcarnitine)

3D Structure for NP0001258 (2-Methylbutyroylcarnitine)