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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2017-03-23 03:56:04 UTC

Update Date

2022-03-07 03:17:56 UTC

HMDB ID

HMDB0062555

Secondary Accession Numbers

HMDB62555

Metabolite Identification

Common Name

hydroxyisovaleroyl carnitine

Description

Hydroxyisovaleroyl carnitine 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. Thus, hydroxyisovaleroyl carnitine is considered to be a fatty ester lipid molecule. Hydroxyisovaleroyl carnitine is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.

Structure

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

HMDB0062555
     RDKit          3D
hydroxyisovaleroyl carnitine
 41 40  0  0  0  0  0  0  0  0999 V2000
    4.3563    1.5350   -0.2024 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2631    0.4765   -0.2702 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8384   -0.8389    0.1639 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1763    0.9184    0.6618 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0255    0.0181    0.7456 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8129   -0.6100    1.8182 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1274   -0.2212   -0.2523 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9744   -1.0502   -0.2228 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5448   -0.9905   -1.5226 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7783   -2.4806    0.1031 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1211   -3.2003   -0.8335 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6744   -2.6552   -1.8263 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3421   -4.5621   -0.5640 O   0  0  0  0  0  1  0  0  0  0  0  0
   -1.9792   -0.4840    0.7657 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4754    0.8057    0.4635 N   0  0  0  0  0  4  0  0  0  0  0  0
   -3.2760    0.8637   -0.7428 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3706    1.1714    1.5763 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5140    1.8662    0.3824 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1739    1.3170   -0.9108 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7673    1.4831    0.8264 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9373    2.5359   -0.3342 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8813    0.3842   -1.3222 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5169   -1.0941    1.1748 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5190   -1.6329   -0.5754 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9655   -0.8113    0.0570 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6642    0.9990    1.6832 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8537    1.9590    0.3716 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1561   -1.7364   -1.6768 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7906   -2.9705   -0.0337 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5302   -2.6847    1.1650 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5179   -0.4820    1.7658 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8459   -1.1961    0.8336 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8503   -0.0415   -0.9497 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6670    1.1995   -1.6227 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0122    1.6913   -0.5919 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0743    1.9270    1.1618 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9473    0.2763    1.8499 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7853    1.6163    2.4081 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1246    2.8195    0.2767 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9404    2.0231    1.3250 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8616    1.8565   -0.4879 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  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
  8 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  1  0
 15 18  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  0
  3 23  1  0
  3 24  1  0
  3 25  1  0
  4 26  1  0
  4 27  1  0
  9 28  1  0
 10 29  1  0
 10 30  1  0
 14 31  1  0
 14 32  1  0
 16 33  1  0
 16 34  1  0
 16 35  1  0
 17 36  1  0
 17 37  1  0
 17 38  1  0
 18 39  1  0
 18 40  1  0
 18 41  1  0
M  CHG  2  13  -1  15   1
M  END


  Mrv1652303231704562D          

 18 17  0  0  0  0            999 V2000
   -0.1914    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5230    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5230    1.9520    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
    1.9520    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520    1.9520    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6664    0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3809    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7934    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0954    1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8099    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5243    1.5395    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    4.8099    0.3020    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9684    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3809    2.5559    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    4.0954    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6664    2.9684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7934    3.2704    0.0000 C   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
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  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
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  2  0  0  0  0
  8 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 15 18  1  0  0  0  0
M  CHG  2  12  -1  15   1
M  END
> <DATABASE_ID>
HMDB0062555

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C12H23NO5/c1-9(2)6-11(16)18-12(17,7-10(14)15)8-13(3,4)5/h9,17H,6-8H2,1-5H3

> <INCHI_KEY>
DHRNMNHPSWBJEN-UHFFFAOYSA-N

> <FORMULA>
C12H23NO5

> <MOLECULAR_WEIGHT>
261.318

> <EXACT_MASS>
261.157622845

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
41

> <JCHEM_AVERAGE_POLARIZABILITY>
27.447886212792742

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
-1.52

> <JCHEM_LOGP>
-3.2039410711384124

> <ALOGPS_LOGS>
-3.40

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.294302348720361

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.175078699994464

> <JCHEM_PKA_STRONGEST_BASIC>
-4.982174261758947

> <JCHEM_POLAR_SURFACE_AREA>
86.66

> <JCHEM_REFRACTIVITY>
87.88059999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.26e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-hydroxy-3-[(3-methylbutanoyl)oxy]-4-(trimethylammonio)butanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0062555
     RDKit          3D
hydroxyisovaleroyl carnitine
 41 40  0  0  0  0  0  0  0  0999 V2000
    4.3563    1.5350   -0.2024 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2631    0.4765   -0.2702 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8384   -0.8389    0.1639 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1763    0.9184    0.6618 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0255    0.0181    0.7456 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8129   -0.6100    1.8182 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1274   -0.2212   -0.2523 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9744   -1.0502   -0.2228 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5448   -0.9905   -1.5226 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7783   -2.4806    0.1031 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1211   -3.2003   -0.8335 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6744   -2.6552   -1.8263 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3421   -4.5621   -0.5640 O   0  0  0  0  0  1  0  0  0  0  0  0
   -1.9792   -0.4840    0.7657 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4754    0.8057    0.4635 N   0  0  0  0  0  4  0  0  0  0  0  0
   -3.2760    0.8637   -0.7428 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3706    1.1714    1.5763 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5140    1.8662    0.3824 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1739    1.3170   -0.9108 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7673    1.4831    0.8264 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9373    2.5359   -0.3342 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8813    0.3842   -1.3222 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5169   -1.0941    1.1748 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5190   -1.6329   -0.5754 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9655   -0.8113    0.0570 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6642    0.9990    1.6832 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8537    1.9590    0.3716 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1561   -1.7364   -1.6768 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7906   -2.9705   -0.0337 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5302   -2.6847    1.1650 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5179   -0.4820    1.7658 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8459   -1.1961    0.8336 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8503   -0.0415   -0.9497 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6670    1.1995   -1.6227 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0122    1.6913   -0.5919 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0743    1.9270    1.1618 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9473    0.2763    1.8499 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7853    1.6163    2.4081 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1246    2.8195    0.2767 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9404    2.0231    1.3250 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8616    1.8565   -0.4879 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  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
  8 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  1  0
 15 18  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  0
  3 23  1  0
  3 24  1  0
  3 25  1  0
  4 26  1  0
  4 27  1  0
  9 28  1  0
 10 29  1  0
 10 30  1  0
 14 31  1  0
 14 32  1  0
 16 33  1  0
 16 34  1  0
 16 35  1  0
 17 36  1  0
 17 37  1  0
 17 38  1  0
 18 39  1  0
 18 40  1  0
 18 41  1  0
M  CHG  2  13  -1  15   1
M  END

HEADER    PROTEIN                                 23-MAR-17   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-MAR-17         0                                  
HETATM    1  C   UNK     0      -0.357   1.334   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.976   2.104   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.976   3.644   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       3.644   2.104   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       3.644   3.644   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0       4.977   1.334   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       6.311   2.104   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       7.081   0.770   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       7.645   2.874   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.978   2.104   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      10.312   2.874   0.000  0.00  0.00           O-1
HETATM   13  O   UNK     0       8.978   0.564   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       5.541   3.437   0.000  0.00  0.00           C+0
HETATM   15  N   UNK     0       6.311   4.771   0.000  0.00  0.00           N+1
HETATM   16  C   UNK     0       7.645   4.001   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.977   5.541   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       7.081   6.105   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9   10   14                                             
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11                                                            
CONECT   14    8   15                                                       
CONECT   15   14   16   17   18                                             
CONECT   16   15                                                            
CONECT   17   15                                                            
CONECT   18   15                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   34    0
END

COMPND    HMDB0062555
HETATM    1  C1  UNL     1       4.356   1.535  -0.202  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.263   0.477  -0.270  1.00  0.00           C  
HETATM    3  C3  UNL     1       3.838  -0.839   0.164  1.00  0.00           C  
HETATM    4  C4  UNL     1       2.176   0.918   0.662  1.00  0.00           C  
HETATM    5  C5  UNL     1       1.026   0.018   0.746  1.00  0.00           C  
HETATM    6  O1  UNL     1       0.813  -0.610   1.818  1.00  0.00           O  
HETATM    7  O2  UNL     1       0.127  -0.221  -0.252  1.00  0.00           O  
HETATM    8  C6  UNL     1      -0.974  -1.050  -0.223  1.00  0.00           C  
HETATM    9  O3  UNL     1      -1.545  -0.990  -1.523  1.00  0.00           O  
HETATM   10  C7  UNL     1      -0.778  -2.481   0.103  1.00  0.00           C  
HETATM   11  C8  UNL     1       0.121  -3.200  -0.833  1.00  0.00           C  
HETATM   12  O4  UNL     1       0.674  -2.655  -1.826  1.00  0.00           O  
HETATM   13  O5  UNL     1       0.342  -4.562  -0.564  1.00  0.00           O1-
HETATM   14  C9  UNL     1      -1.979  -0.484   0.766  1.00  0.00           C  
HETATM   15  N1  UNL     1      -2.475   0.806   0.463  1.00  0.00           N1+
HETATM   16  C10 UNL     1      -3.276   0.864  -0.743  1.00  0.00           C  
HETATM   17  C11 UNL     1      -3.371   1.171   1.576  1.00  0.00           C  
HETATM   18  C12 UNL     1      -1.514   1.866   0.382  1.00  0.00           C  
HETATM   19  H1  UNL     1       5.174   1.317  -0.911  1.00  0.00           H  
HETATM   20  H2  UNL     1       4.767   1.483   0.826  1.00  0.00           H  
HETATM   21  H3  UNL     1       3.937   2.536  -0.334  1.00  0.00           H  
HETATM   22  H4  UNL     1       2.881   0.384  -1.322  1.00  0.00           H  
HETATM   23  H5  UNL     1       3.517  -1.094   1.175  1.00  0.00           H  
HETATM   24  H6  UNL     1       3.519  -1.633  -0.575  1.00  0.00           H  
HETATM   25  H7  UNL     1       4.966  -0.811   0.057  1.00  0.00           H  
HETATM   26  H8  UNL     1       2.664   0.999   1.683  1.00  0.00           H  
HETATM   27  H9  UNL     1       1.854   1.959   0.372  1.00  0.00           H  
HETATM   28  H10 UNL     1      -2.156  -1.736  -1.677  1.00  0.00           H  
HETATM   29  H11 UNL     1      -1.791  -2.970  -0.034  1.00  0.00           H  
HETATM   30  H12 UNL     1      -0.530  -2.685   1.165  1.00  0.00           H  
HETATM   31  H13 UNL     1      -1.518  -0.482   1.766  1.00  0.00           H  
HETATM   32  H14 UNL     1      -2.846  -1.196   0.834  1.00  0.00           H  
HETATM   33  H15 UNL     1      -3.850  -0.042  -0.950  1.00  0.00           H  
HETATM   34  H16 UNL     1      -2.667   1.200  -1.623  1.00  0.00           H  
HETATM   35  H17 UNL     1      -4.012   1.691  -0.592  1.00  0.00           H  
HETATM   36  H18 UNL     1      -4.074   1.927   1.162  1.00  0.00           H  
HETATM   37  H19 UNL     1      -3.947   0.276   1.850  1.00  0.00           H  
HETATM   38  H20 UNL     1      -2.785   1.616   2.408  1.00  0.00           H  
HETATM   39  H21 UNL     1      -2.125   2.819   0.277  1.00  0.00           H  
HETATM   40  H22 UNL     1      -0.940   2.023   1.325  1.00  0.00           H  
HETATM   41  H23 UNL     1      -0.862   1.857  -0.488  1.00  0.00           H  
CONECT    1    2   19   20   21
CONECT    2    3    4   22
CONECT    3   23   24   25
CONECT    4    5   26   27
CONECT    5    6    6    7
CONECT    7    8
CONECT    8    9   10   14
CONECT    9   28
CONECT   10   11   29   30
CONECT   11   12   12   13
CONECT   14   15   31   32
CONECT   15   16   17   18
CONECT   16   33   34   35
CONECT   17   36   37   38
CONECT   18   39   40   41
END

HMDB0062555
     RDKit          3D
hydroxyisovaleroyl carnitine
 41 40  0  0  0  0  0  0  0  0999 V2000
    4.3563    1.5350   -0.2024 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2631    0.4765   -0.2702 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8384   -0.8389    0.1639 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1763    0.9184    0.6618 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0255    0.0181    0.7456 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8129   -0.6100    1.8182 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1274   -0.2212   -0.2523 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9744   -1.0502   -0.2228 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5448   -0.9905   -1.5226 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7783   -2.4806    0.1031 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1211   -3.2003   -0.8335 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6744   -2.6552   -1.8263 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3421   -4.5621   -0.5640 O   0  0  0  0  0  1  0  0  0  0  0  0
   -1.9792   -0.4840    0.7657 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4754    0.8057    0.4635 N   0  0  0  0  0  4  0  0  0  0  0  0
   -3.2760    0.8637   -0.7428 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3706    1.1714    1.5763 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5140    1.8662    0.3824 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1739    1.3170   -0.9108 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7673    1.4831    0.8264 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9373    2.5359   -0.3342 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8813    0.3842   -1.3222 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5169   -1.0941    1.1748 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5190   -1.6329   -0.5754 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9655   -0.8113    0.0570 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6642    0.9990    1.6832 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8537    1.9590    0.3716 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1561   -1.7364   -1.6768 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7906   -2.9705   -0.0337 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5302   -2.6847    1.1650 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5179   -0.4820    1.7658 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8459   -1.1961    0.8336 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8503   -0.0415   -0.9497 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6670    1.1995   -1.6227 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0122    1.6913   -0.5919 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0743    1.9270    1.1618 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9473    0.2763    1.8499 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7853    1.6163    2.4081 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1246    2.8195    0.2767 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9404    2.0231    1.3250 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8616    1.8565   -0.4879 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  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
  8 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  1  0
 15 18  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  0
  3 23  1  0
  3 24  1  0
  3 25  1  0
  4 26  1  0
  4 27  1  0
  9 28  1  0
 10 29  1  0
 10 30  1  0
 14 31  1  0
 14 32  1  0
 16 33  1  0
 16 34  1  0
 16 35  1  0
 17 36  1  0
 17 37  1  0
 17 38  1  0
 18 39  1  0
 18 40  1  0
 18 41  1  0
M  CHG  2  13  -1  15   1
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₂H₂₃NO₅

Average Molecular Weight

261.318

Monoisotopic Molecular Weight

261.157622845

IUPAC Name

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

Traditional Name

3-hydroxy-3-[(3-methylbutanoyl)oxy]-4-(trimethylammonio)butanoate

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C12H23NO5/c1-9(2)6-11(16)18-12(17,7-10(14)15)8-13(3,4)5/h9,17H,6-8H2,1-5H3

InChI Key

DHRNMNHPSWBJEN-UHFFFAOYSA-N

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
Carnitine
Branched fatty acid
Hydroxy fatty acid
Short-chain hydroxy acid
Dicarboxylic acid or derivatives
Hemiketal
Tetraalkylammonium salt
Quaternary ammonium salt
Carboxylic acid ester
Carboxylic acid salt
Hemiacetal
Carboxylic acid
Carboxylic acid derivative
Organic salt
Hydrocarbon derivative
Amine
Organic oxide
Organopnictogen compound
Organic nitrogen compound
Carbonyl group
Organic oxygen compound
Organonitrogen compound
Organooxygen compound
Organic cation
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 32966057)

Excreta

Biofluid or Excreta

Feces (PMID: 27543620)
Urine (PMID: 32966057)

Source

Exogenous

Exogenous (HMDB: HMDB0062555)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.13 g/l	ALOGPS
LogP	-1.52	ALOGPS

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	-1.5	ALOGPS
logP	-3.2	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	4.18	ChemAxon
pKa (Strongest Basic)	-5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	86.66 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	87.88 m³·mol⁻¹	ChemAxon
Polarizability	27.45 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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	160.769	30932474
DeepCCS	[M-H]-	158.41	30932474
DeepCCS	[M-2H]-	191.519	30932474
DeepCCS	[M+Na]+	167.571	30932474
AllCCS	[M+H]+	161.6	32859911
AllCCS	[M+H-H2O]+	158.7	32859911
AllCCS	[M+NH4]+	164.3	32859911
AllCCS	[M+Na]+	165.1	32859911
AllCCS	[M-H]-	167.1	32859911
AllCCS	[M+Na-2H]-	168.1	32859911
AllCCS	[M+HCOO]-	169.3	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	2.16 minutes	32390414
Predicted by Siyang on May 30, 2022	10.1661 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	6.14 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1222.0 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	190.3 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	120.2 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	150.1 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	59.0 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	354.6 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	347.5 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	556.4 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	850.0 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	227.6 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1380.1 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	199.5 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	249.5 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	320.5 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	287.0 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	70.5 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
hydroxyisovaleroyl carnitine	CC(C)CC(=O)OC(O)(CC([O-])=O)C[N+](C)(C)C	2302.8	Standard polar	33892256
hydroxyisovaleroyl carnitine	CC(C)CC(=O)OC(O)(CC([O-])=O)C[N+](C)(C)C	1419.4	Standard non polar	33892256
hydroxyisovaleroyl carnitine	CC(C)CC(=O)OC(O)(CC([O-])=O)C[N+](C)(C)C	1648.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
hydroxyisovaleroyl carnitine,1TMS,isomer #1	CC(C)CC(=O)OC(CC(=O)[O-])(C[N+](C)(C)C)O[Si](C)(C)C	1685.2	Semi standard non polar	33892256
hydroxyisovaleroyl carnitine,1TBDMS,isomer #1	CC(C)CC(=O)OC(CC(=O)[O-])(C[N+](C)(C)C)O[Si](C)(C)C(C)(C)C	1917.3	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - hydroxyisovaleroyl carnitine GC-MS (1 TMS) - 70eV, Positive	splash10-00di-9000000000-d026ff89b7e53a9606b1	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - hydroxyisovaleroyl carnitine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - hydroxyisovaleroyl carnitine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - hydroxyisovaleroyl carnitine 10V, Positive-QTOF	splash10-03di-4690000000-704b8c74408f3875145e	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - hydroxyisovaleroyl carnitine 20V, Positive-QTOF	splash10-0k9f-9300000000-952b5f81c0a79d76fb57	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - hydroxyisovaleroyl carnitine 40V, Positive-QTOF	splash10-06xx-9200000000-98f3b78858d3971c47f2	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - hydroxyisovaleroyl carnitine 10V, Negative-QTOF	splash10-0nmi-0490000000-76fd811276e57576df52	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - hydroxyisovaleroyl carnitine 20V, Negative-QTOF	splash10-0bt9-9250000000-7ca425c7e1e22baeb8be	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - hydroxyisovaleroyl carnitine 40V, Negative-QTOF	splash10-0f89-9200000000-5c8e8633e3b40e9bd725	2021-09-24	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood
Feces
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	27543620	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	25037050	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	25037050	details

Associated Disorders and Diseases

Disease References

Colorectal cancer
Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]

Associated OMIM IDs

114500 (Colorectal cancer)

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

57357187

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Showing metabocard for hydroxyisovaleroyl carnitine (HMDB0062555)

MOL for HMDB0062555 (hydroxyisovaleroyl carnitine)

3D MOL for HMDB0062555 (hydroxyisovaleroyl carnitine)

3D SDF for HMDB0062555 (hydroxyisovaleroyl carnitine)

3D-SDF for HMDB0062555 (hydroxyisovaleroyl carnitine)

PDB for HMDB0062555 (hydroxyisovaleroyl carnitine)

3D PDB for HMDB0062555 (hydroxyisovaleroyl carnitine)

SMILES for HMDB0062555 (hydroxyisovaleroyl carnitine)

INCHI for HMDB0062555 (hydroxyisovaleroyl carnitine)

Structure for HMDB0062555 (hydroxyisovaleroyl carnitine)

3D Structure for HMDB0062555 (hydroxyisovaleroyl carnitine)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra