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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2009-11-02 22:43:15 UTC

Update Date

2023-05-30 20:55:49 UTC

HMDB ID

HMDB0013125

Secondary Accession Numbers

HMDB13125

Metabolite Identification

Common Name

Hydroxypropionylcarnitine

Description

Hydroxypropionylcarnitine is an acylcarnitine. More specifically, it is an hydroxypropionoic acid ester of carnitine. Acylcarnitines were first discovered more than 70 year ago (PMID: 13825279 ). It is believed that there are more than 1000 types of acylcarnitines in the human body. The general role of acylcarnitines is to transport acyl-groups (organic acids and fatty acids) from the cytoplasm into the mitochondria so that they can be broken down to produce energy. This process is known as beta-oxidation. According to a recent review (PMID: 35710135 ), acylcarnitines (ACs) can be classified into 9 different categories depending on the type and size of their acyl-group: 1) short-chain ACs; 2) medium-chain ACs; 3) long-chain ACs; 4) very long-chain ACs; 5) hydroxy ACs; 6) branched chain ACs; 7) unsaturated ACs; 8) dicarboxylic ACs and 9) miscellaneous ACs. Short-chain ACs have acyl-groups with two to five carbons (C2-C5), medium-chain ACs have acyl-groups with six to thirteen carbons (C6-C13), long-chain ACs have acyl-groups with fourteen to twenty once carbons (C14-C21) and very long-chain ACs have acyl groups with more than 22 carbons. Hydroxypropionylcarnitine is therefore classified as a short chain AC. As a short-chain acylcarnitine hydroxypropionylcarnitine is a member of the most abundant group of carnitines in the body, comprising more than 50% of all acylcarnitines quantified in tissues and biofluids (PMID: 31920980 ). Some short-chain carnitines have been studied as supplements or treatments for a number of diseases, including neurological disorders and inborn errors of metabolism. It is also decreased in the urine of individuals with obesity (PMID: 26910390 ) and systolic heart failure (PMID: 26010610 ). Hydroxypropionylcarnitine can also be found incerebrospinal fluid. Carnitine acetyltransferase (CrAT, EC:2.3.1.7) is responsible for the synthesis of all short-chain and short branched-chain acylcarnitines (PMID: 23485643 ). The study of acylcarnitines is an active area of research and it is likely that many novel acylcarnitines will be discovered in the coming years. It is also likely that many novel roles in health and disease will be uncovered. An excellent review of the current state of knowledge for acylcarnitines is available (PMID: 35710135 ).

Structure

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

HMDB0013125
     RDKit          3D
Hydroxypropionylcarnitine
 35 34  0  0  0  0  0  0  0  0999 V2000
   -3.0464   -1.2169    0.1622 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6592   -0.7740    0.3248 N   0  0  0  0  0  4  0  0  0  0  0  0
   -1.5134   -0.2716    1.6424 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8444   -1.9855    0.1814 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3746    0.1346   -0.7433 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2531    1.0755   -0.5244 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1971    2.0323   -1.6887 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4165    2.8453   -1.8405 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6179    3.5759   -2.8690 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4202    2.8823   -0.8957 O   0  0  0  0  0  1  0  0  0  0  0  0
    0.9817    0.4367   -0.3000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7950    0.6104    0.7731 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3964    1.4392    1.6690 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0840   -0.0256    1.0544 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4733   -1.0568    0.0126 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7184   -1.5657    0.4122 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7442   -0.5752    0.7635 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3274   -1.1048   -0.9159 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1457   -2.2611    0.4794 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5295   -0.6157    2.0802 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6386    0.8284    1.7355 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2877   -0.7214    2.3078 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6658   -2.1165   -0.9106 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0935   -1.8543    0.7430 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4320   -2.8516    0.5216 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2992    0.6344   -1.0289 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0630   -0.5209   -1.6169 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4045    1.7353    0.3796 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6419    2.7572   -1.5940 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1147    1.4331   -2.6294 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1799   -0.4227    2.0794 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8899    0.7672    0.9774 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7370   -1.8838   -0.0615 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6272   -0.5498   -0.9478 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3768   -0.8139    0.2669 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  2  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
  6 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  3 20  1  0
  3 21  1  0
  3 22  1  0
  4 23  1  0
  4 24  1  0
  4 25  1  0
  5 26  1  0
  5 27  1  0
  6 28  1  1
  7 29  1  0
  7 30  1  0
 14 31  1  0
 14 32  1  0
 15 33  1  0
 15 34  1  0
 16 35  1  0
M  CHG  2   2   1  10  -1
M  END

  Mrv0541 02251208172D          

 16 15  0  0  1  0            999 V2000
   16.2000   -7.4737    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   16.9144   -7.0612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6288   -7.4737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6288   -8.2985    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   16.2000   -8.2985    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.3431   -7.0612    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.4856   -7.0612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4856   -6.2362    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
   16.3105   -6.2362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6607   -6.2362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4856   -5.4114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5456   -9.7313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9591   -9.0149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7864   -9.0149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2000   -9.7313    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.7571  -10.3267    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  2  1  0  0  0  0
  4  3  1  0  0  0  0
  1  5  1  6  0  0  0
  3  6  2  0  0  0  0
  7  1  1  0  0  0  0
  8  7  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
 13 12  1  0  0  0  0
 14 13  1  0  0  0  0
  5 14  1  0  0  0  0
 15 14  2  0  0  0  0
 12 16  1  0  0  0  0
M  CHG  2   4  -1   8   1
M  END
> <DATABASE_ID>
HMDB0013125

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C10H19NO5/c1-11(2,3)7-8(6-9(13)14)16-10(15)4-5-12/h8,12H,4-7H2,1-3H3/t8-/m0/s1

> <INCHI_KEY>
QJGJXKFJFRSERW-QMMMGPOBSA-N

> <FORMULA>
C10H19NO5

> <MOLECULAR_WEIGHT>
233.2616

> <EXACT_MASS>
233.126322723

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
23.762413006667607

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3S)-3-[(3-hydroxypropanoyl)oxy]-4-(trimethylazaniumyl)butanoate

> <ALOGPS_LOGP>
-2.43

> <JCHEM_LOGP>
-5.026615947471745

> <ALOGPS_LOGS>
-2.43

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.733619355079838

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.0520995188305164

> <JCHEM_PKA_STRONGEST_BASIC>
-2.477915178250913

> <JCHEM_POLAR_SURFACE_AREA>
86.66000000000001

> <JCHEM_REFRACTIVITY>
79.0384

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.06e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3S)-3-[(3-hydroxypropanoyl)oxy]-4-(trimethylammonio)butanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0013125
     RDKit          3D
Hydroxypropionylcarnitine
 35 34  0  0  0  0  0  0  0  0999 V2000
   -3.0464   -1.2169    0.1622 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6592   -0.7740    0.3248 N   0  0  0  0  0  4  0  0  0  0  0  0
   -1.5134   -0.2716    1.6424 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8444   -1.9855    0.1814 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3746    0.1346   -0.7433 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2531    1.0755   -0.5244 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1971    2.0323   -1.6887 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4165    2.8453   -1.8405 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6179    3.5759   -2.8690 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4202    2.8823   -0.8957 O   0  0  0  0  0  1  0  0  0  0  0  0
    0.9817    0.4367   -0.3000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7950    0.6104    0.7731 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3964    1.4392    1.6690 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0840   -0.0256    1.0544 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4733   -1.0568    0.0126 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7184   -1.5657    0.4122 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7442   -0.5752    0.7635 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3274   -1.1048   -0.9159 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1457   -2.2611    0.4794 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5295   -0.6157    2.0802 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6386    0.8284    1.7355 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2877   -0.7214    2.3078 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6658   -2.1165   -0.9106 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0935   -1.8543    0.7430 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4320   -2.8516    0.5216 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2992    0.6344   -1.0289 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0630   -0.5209   -1.6169 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4045    1.7353    0.3796 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6419    2.7572   -1.5940 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1147    1.4331   -2.6294 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1799   -0.4227    2.0794 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8899    0.7672    0.9774 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7370   -1.8838   -0.0615 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6272   -0.5498   -0.9478 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3768   -0.8139    0.2669 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  2  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
  6 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  3 20  1  0
  3 21  1  0
  3 22  1  0
  4 23  1  0
  4 24  1  0
  4 25  1  0
  5 26  1  0
  5 27  1  0
  6 28  1  1
  7 29  1  0
  7 30  1  0
 14 31  1  0
 14 32  1  0
 15 33  1  0
 15 34  1  0
 16 35  1  0
M  CHG  2   2   1  10  -1
M  END

HEADER    PROTEIN                                 25-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-FEB-12         0                                  
HETATM    1  C   UNK     0      30.240 -13.951   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      31.573 -13.181   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      32.907 -13.951   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      32.907 -15.491   0.000  0.00  0.00           O-1
HETATM    5  O   UNK     0      30.240 -15.491   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0      34.241 -13.181   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      28.906 -13.181   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0      28.906 -11.641   0.000  0.00  0.00           N+1
HETATM    9  C   UNK     0      30.446 -11.641   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      27.367 -11.641   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      28.906 -10.101   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      27.152 -18.165   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      27.924 -16.828   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      29.468 -16.828   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      30.240 -18.165   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0      27.547 -19.276   0.000  0.00  0.00           O+0
CONECT    1    2    5    7                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4    6                                                  
CONECT    4    3                                                            
CONECT    5    1   14                                                       
CONECT    6    3                                                            
CONECT    7    1    8                                                       
CONECT    8    7    9   10   11                                             
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11    8                                                            
CONECT   12   13   16                                                       
CONECT   13   12   14                                                       
CONECT   14   13    5   15                                                  
CONECT   15   14                                                            
CONECT   16   12                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   30    0
END

COMPND    HMDB0013125
HETATM    1  C1  UNL     1      -3.046  -1.217   0.162  1.00  0.00           C  
HETATM    2  N1  UNL     1      -1.659  -0.774   0.325  1.00  0.00           N1+
HETATM    3  C2  UNL     1      -1.513  -0.272   1.642  1.00  0.00           C  
HETATM    4  C3  UNL     1      -0.844  -1.986   0.181  1.00  0.00           C  
HETATM    5  C4  UNL     1      -1.375   0.135  -0.743  1.00  0.00           C  
HETATM    6  C5  UNL     1      -0.253   1.076  -0.524  1.00  0.00           C  
HETATM    7  C6  UNL     1      -0.197   2.032  -1.689  1.00  0.00           C  
HETATM    8  C7  UNL     1      -1.416   2.845  -1.841  1.00  0.00           C  
HETATM    9  O1  UNL     1      -1.618   3.576  -2.869  1.00  0.00           O  
HETATM   10  O2  UNL     1      -2.420   2.882  -0.896  1.00  0.00           O1-
HETATM   11  O3  UNL     1       0.982   0.437  -0.300  1.00  0.00           O  
HETATM   12  C8  UNL     1       1.795   0.610   0.773  1.00  0.00           C  
HETATM   13  O4  UNL     1       1.396   1.439   1.669  1.00  0.00           O  
HETATM   14  C9  UNL     1       3.084  -0.026   1.054  1.00  0.00           C  
HETATM   15  C10 UNL     1       3.473  -1.057   0.013  1.00  0.00           C  
HETATM   16  O5  UNL     1       4.718  -1.566   0.412  1.00  0.00           O  
HETATM   17  H1  UNL     1      -3.744  -0.575   0.763  1.00  0.00           H  
HETATM   18  H2  UNL     1      -3.327  -1.105  -0.916  1.00  0.00           H  
HETATM   19  H3  UNL     1      -3.146  -2.261   0.479  1.00  0.00           H  
HETATM   20  H4  UNL     1      -0.529  -0.616   2.080  1.00  0.00           H  
HETATM   21  H5  UNL     1      -1.639   0.828   1.736  1.00  0.00           H  
HETATM   22  H6  UNL     1      -2.288  -0.721   2.308  1.00  0.00           H  
HETATM   23  H7  UNL     1      -0.666  -2.117  -0.911  1.00  0.00           H  
HETATM   24  H8  UNL     1       0.093  -1.854   0.743  1.00  0.00           H  
HETATM   25  H9  UNL     1      -1.432  -2.852   0.522  1.00  0.00           H  
HETATM   26  H10 UNL     1      -2.299   0.634  -1.029  1.00  0.00           H  
HETATM   27  H11 UNL     1      -1.063  -0.521  -1.617  1.00  0.00           H  
HETATM   28  H12 UNL     1      -0.404   1.735   0.380  1.00  0.00           H  
HETATM   29  H13 UNL     1       0.642   2.757  -1.594  1.00  0.00           H  
HETATM   30  H14 UNL     1      -0.115   1.433  -2.629  1.00  0.00           H  
HETATM   31  H15 UNL     1       3.180  -0.423   2.079  1.00  0.00           H  
HETATM   32  H16 UNL     1       3.890   0.767   0.977  1.00  0.00           H  
HETATM   33  H17 UNL     1       2.737  -1.884  -0.061  1.00  0.00           H  
HETATM   34  H18 UNL     1       3.627  -0.550  -0.948  1.00  0.00           H  
HETATM   35  H19 UNL     1       5.377  -0.814   0.267  1.00  0.00           H  
CONECT    1    2   17   18   19
CONECT    2    3    4    5
CONECT    3   20   21   22
CONECT    4   23   24   25
CONECT    5    6   26   27
CONECT    6    7   11   28
CONECT    7    8   29   30
CONECT    8    9    9   10
CONECT   11   12
CONECT   12   13   13   14
CONECT   14   15   31   32
CONECT   15   16   33   34
CONECT   16   35
END

HMDB0013125
     RDKit          3D
Hydroxypropionylcarnitine
 35 34  0  0  0  0  0  0  0  0999 V2000
   -3.0464   -1.2169    0.1622 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6592   -0.7740    0.3248 N   0  0  0  0  0  4  0  0  0  0  0  0
   -1.5134   -0.2716    1.6424 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8444   -1.9855    0.1814 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3746    0.1346   -0.7433 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2531    1.0755   -0.5244 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1971    2.0323   -1.6887 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4165    2.8453   -1.8405 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6179    3.5759   -2.8690 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4202    2.8823   -0.8957 O   0  0  0  0  0  1  0  0  0  0  0  0
    0.9817    0.4367   -0.3000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7950    0.6104    0.7731 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3964    1.4392    1.6690 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0840   -0.0256    1.0544 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4733   -1.0568    0.0126 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7184   -1.5657    0.4122 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7442   -0.5752    0.7635 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3274   -1.1048   -0.9159 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1457   -2.2611    0.4794 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5295   -0.6157    2.0802 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6386    0.8284    1.7355 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2877   -0.7214    2.3078 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6658   -2.1165   -0.9106 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0935   -1.8543    0.7430 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4320   -2.8516    0.5216 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2992    0.6344   -1.0289 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0630   -0.5209   -1.6169 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4045    1.7353    0.3796 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6419    2.7572   -1.5940 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1147    1.4331   -2.6294 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1799   -0.4227    2.0794 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8899    0.7672    0.9774 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7370   -1.8838   -0.0615 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6272   -0.5498   -0.9478 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3768   -0.8139    0.2669 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  2  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
  6 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  3 20  1  0
  3 21  1  0
  3 22  1  0
  4 23  1  0
  4 24  1  0
  4 25  1  0
  5 26  1  0
  5 27  1  0
  6 28  1  1
  7 29  1  0
  7 30  1  0
 14 31  1  0
 14 32  1  0
 15 33  1  0
 15 34  1  0
 16 35  1  0
M  CHG  2   2   1  10  -1
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
Hydroxypropionyl-L-carnitine	HMDB

Chemical Formula

C₁₀H₁₉NO₅

Average Molecular Weight

233.2616

Monoisotopic Molecular Weight

233.126322723

IUPAC Name

(3S)-3-[(3-hydroxypropanoyl)oxy]-4-(trimethylazaniumyl)butanoate

Traditional Name

(3S)-3-[(3-hydroxypropanoyl)oxy]-4-(trimethylammonio)butanoate

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C10H19NO5/c1-11(2,3)7-8(6-9(13)14)16-10(15)4-5-12/h8,12H,4-7H2,1-3H3/t8-/m0/s1

InChI Key

QJGJXKFJFRSERW-QMMMGPOBSA-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
Beta-hydroxy acid
Dicarboxylic acid or derivatives
Hydroxy acid
Tetraalkylammonium salt
Quaternary ammonium salt
Carboxylic acid ester
Carboxylic acid salt
Carboxylic acid derivative
Carboxylic acid
Organic nitrogen compound
Organooxygen compound
Organonitrogen compound
Primary alcohol
Organic zwitterion
Organic salt
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Carbonyl group
Organic oxygen compound
Amine
Alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 24704061)
Cerebrospinal Fluid (CSF) (PMID: 22546835)
Cerebrospinal fluid (HMDB: HMDB0013125)

Cellular substructure

Organelle

Peroxisome (PMID: 35710135)

Excreta

Biofluid or Excreta

Urine (PMID: 24023812)
Feces (PMID: 27624970)

Cell

All cells and tissues (PMID: 35710135)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0013125)

Source

Exogenous

Food

Food (HMDB: HMDB0013125)

Animal origin

Poultry

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Exogenous (HMDB: HMDB0013125)

Endogenous

Animal

Animal (HMDB: HMDB0013125)

Endogenous (HMDB: HMDB0013125)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0013125)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0013125)

Lipid metabolism pathway (HMDB: HMDB0013125)

Cellular process

Cell signaling (HMDB: HMDB0013125)

Biochemical process

Lipid transport (HMDB: HMDB0013125)

Role

Physical Properties

State

Solid

Experimental Molecular 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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	1.06 g/L	ALOGPS
logP	-2.4	ALOGPS
logP	-5	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	4.05	ChemAxon
pKa (Strongest Basic)	-2.5	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	79.04 m³·mol⁻¹	ChemAxon
Polarizability	23.76 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]+	154.014	30932474
DeepCCS	[M-H]-	151.708	30932474
DeepCCS	[M-2H]-	184.966	30932474
DeepCCS	[M+Na]+	160.02	30932474
AllCCS	[M+H]+	152.9	32859911
AllCCS	[M+H-H2O]+	149.7	32859911
AllCCS	[M+NH4]+	155.8	32859911
AllCCS	[M+Na]+	156.7	32859911
AllCCS	[M-H]-	159.4	32859911
AllCCS	[M+Na-2H]-	160.4	32859911
AllCCS	[M+HCOO]-	161.5	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Hydroxypropionylcarnitine	C[N+](C)(C)C[C@H](CC([O-])=O)OC(=O)CCO	2534.7	Standard polar	33892256
Hydroxypropionylcarnitine	C[N+](C)(C)C[C@H](CC([O-])=O)OC(=O)CCO	1406.9	Standard non polar	33892256
Hydroxypropionylcarnitine	C[N+](C)(C)C[C@H](CC([O-])=O)OC(=O)CCO	1683.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Hydroxypropionylcarnitine,1TMS,isomer #1	C[N+](C)(C)C[C@H](CC(=O)[O-])OC(=O)CCO[Si](C)(C)C	1658.8	Semi standard non polar	33892256
Hydroxypropionylcarnitine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OCCC(=O)O[C@@H](CC(=O)[O-])C[N+](C)(C)C	1897.3	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 - Hydroxypropionylcarnitine GC-MS (1 TMS) - 70eV, Positive	splash10-00di-9300000000-b92ed8b4bc16ca8776d8	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Hydroxypropionylcarnitine 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 - Hydroxypropionylcarnitine 10V, Positive-QTOF	splash10-001i-0090000000-b349da287b2f6b90f65a	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydroxypropionylcarnitine 20V, Positive-QTOF	splash10-0019-9050000000-48d8edc669755c80f2c1	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydroxypropionylcarnitine 40V, Positive-QTOF	splash10-000i-9000000000-e9262cbaff8cb4ad0ba6	2021-09-23	Wishart Lab	View Spectrum

NMR Spectra

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

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Blood
Cerebrospinal Fluid (CSF)
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 and Quantified	0.020-0.100 uM	Adult (>18 years old)	Both	Normal	The Metabolo...	details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Normal	Not Available	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.063 +/- 0.030 uM	Adult (>18 years old)	Not Specified	Normal	22546835	details
Feces	Detected and Quantified	0.24 +/- 0.12 nmol/g wet feces	Adult (>18 years old)	Both	Normal	27624970	details
Feces	Detected and Quantified	0.19 +/- 0.09 nmol/g wet feces	Adult (>18 years old)	Both	Normal	27624970	details
Urine	Detected and Quantified	0.008 (0.004-0.012) umol/mmol creatinine	Adult (>18 years old)	Both	Normal	24023812	details
Urine	Detected and Quantified	1.29 +/- 0.10 umol/mmol creatinine	Adolescent (13-18 years old)	Both	Normal	26910390	details
Urine	Detected and Quantified	0.02 (0.01-0.05) umol/mmol creatinine	Newborn (0-30 days old)	Both	Normal	Analysis of 40 NI...	details
Urine	Detected and Quantified	0.01-0.06 umol/mmol creatinine	Newborn (0-30 days old)	Both	Normal	32340350	details
Urine	Detected and Quantified	0.02 +/- 0.01 umol/mmol creatinine	Newborn (0-30 days old)	Female	Normal	32340350	details
Urine	Detected and Quantified	0.03 +/- 0.01 umol/mmol creatinine	Newborn (0-30 days old)	Male	Normal	32340350	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.0918 (0.0644) uM	Adult (>18 years old)	Female	Pregnancy with fetus having congenital heart defect	24704061	details
Urine	Detected and Quantified	2.43 +/- 0.15 umol/mmol creatinine	Adolescent (13-18 years old)	Both	Obese	26910390	details

Associated Disorders and Diseases

Disease References

Obesity
Cho K, Moon JS, Kang JH, Jang HB, Lee HJ, Park SI, Yu KS, Cho JY: Combined untargeted and targeted metabolomic profiling reveals urinary biomarkers for discriminating obese from normal-weight adolescents. Pediatr Obes. 2017 Apr;12(2):93-101. doi: 10.1111/ijpo.12114. Epub 2016 Feb 22. [PubMed:26910390 ]

Associated OMIM IDs

601665 (Obesity)

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB029298

KNApSAcK ID

Not Available

Chemspider ID

30776692

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

53481699

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

MDB00000849

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Zordoky BN, Sung MM, Ezekowitz J, Mandal R, Han B, Bjorndahl TC, Bouatra S, Anderson T, Oudit GY, Wishart DS, Dyck JR: Metabolomic fingerprint of heart failure with preserved ejection fraction. PLoS One. 2015 May 26;10(5):e0124844. doi: 10.1371/journal.pone.0124844. eCollection 2015. [PubMed:26010610 ]
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 ]
Violante S, Ijlst L, Ruiter J, Koster J, van Lenthe H, Duran M, de Almeida IT, Wanders RJ, Houten SM, Ventura FV: Substrate specificity of human carnitine acetyltransferase: Implications for fatty acid and branched-chain amino acid metabolism. Biochim Biophys Acta. 2013 Jun;1832(6):773-9. doi: 10.1016/j.bbadis.2013.02.012. Epub 2013 Feb 24. [PubMed:23485643 ]
Cho K, Moon JS, Kang JH, Jang HB, Lee HJ, Park SI, Yu KS, Cho JY: Combined untargeted and targeted metabolomic profiling reveals urinary biomarkers for discriminating obese from normal-weight adolescents. Pediatr Obes. 2017 Apr;12(2):93-101. doi: 10.1111/ijpo.12114. Epub 2016 Feb 22. [PubMed:26910390 ]
FRITZ IB: Action of carnitine on long chain fatty acid oxidation by liver. Am J Physiol. 1959 Aug;197:297-304. doi: 10.1152/ajplegacy.1959.197.2.297. [PubMed:13825279 ]
Makarova E, Makrecka-Kuka M, Vilks K, Volska K, Sevostjanovs E, Grinberga S, Zarkova-Malkova O, Dambrova M, Liepinsh E: Decreases in Circulating Concentrations of Long-Chain Acylcarnitines and Free Fatty Acids During the Glucose Tolerance Test Represent Tissue-Specific Insulin Sensitivity. Front Endocrinol (Lausanne). 2019 Dec 17;10:870. doi: 10.3389/fendo.2019.00870. eCollection 2019. [PubMed:31920980 ]
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Showing metabocard for Hydroxypropionylcarnitine (HMDB0013125)

MOL for HMDB0013125 (Hydroxypropionylcarnitine)

3D MOL for HMDB0013125 (Hydroxypropionylcarnitine)

3D SDF for HMDB0013125 (Hydroxypropionylcarnitine)

3D-SDF for HMDB0013125 (Hydroxypropionylcarnitine)

PDB for HMDB0013125 (Hydroxypropionylcarnitine)

3D PDB for HMDB0013125 (Hydroxypropionylcarnitine)

SMILES for HMDB0013125 (Hydroxypropionylcarnitine)

INCHI for HMDB0013125 (Hydroxypropionylcarnitine)

Structure for HMDB0013125 (Hydroxypropionylcarnitine)

3D Structure for HMDB0013125 (Hydroxypropionylcarnitine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra