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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2021-02-24 01:49:05 UTC

Update Date

2022-10-24 19:44:18 UTC

HMDB ID

HMDB0240784

Secondary Accession Numbers

None

Metabolite Identification

Common Name

O-Propanoyl-D-carnitine

Description

O-Propanoyl-D-carnitine is an acylcarnitine. More specifically, it is an propanoic 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. O-Propanoyl-D-carnitine is therefore classified as a short chain AC. As a short-chain acylcarnitine O-Propanoyl-D-carnitine 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. In particular O-Propanoyl-D-carnitine is elevated in the blood or plasma of individuals with methylmalonic academia/methylmalonyl-CoA mutase (PMID: 26454439 , PMID: 25750861 , PMID: 31622506 , PMID: 30712249 ), propionic academia/mitochondrial propionyl-CoA carboxylase deficiency (PMID: 31715057 , PMID: 28915261 ), obesity and Type 2 Diabetes Mellitus (PMID: 30186675 ), cobalamin C deficiency (PMID: 25367534 ), chronic heart failure (PMID: 22622056 ), diastolic heart failure (PMID: 26010610 ), and systolic heart failure (PMID: 26010610 ). It is also decreased in the blood or plasma of individuals with familial Mediterranean fever (PMID: 29900937 ) and type 2 diabetes Mellitus (PMID: 19369366 ). It is also decreased in the urine of individuals with obesity (PMID: 26910390 ). 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

HMDB0240784
     RDKit          3D
O-Propanoyl-D-carnitine
 34 33  0  0  0  0  0  0  0  0999 V2000
    4.8093   -0.8407   -0.4707 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6213   -0.3147   -1.2081 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4374   -0.1777   -0.3081 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5765   -0.5042    0.8963 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2299    0.2885   -0.7682 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0742    0.4340    0.0778 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3913    1.8603    0.0408 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6293    2.8268    0.5095 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7593    2.4498    0.8918 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2960    4.1643    0.5126 O   0  0  0  0  0  1  0  0  0  0  0  0
   -0.9529   -0.4994   -0.4993 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2010   -0.5555    0.1944 N   0  0  0  0  0  4  0  0  0  0  0  0
   -2.0291   -0.5723    1.6326 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7865   -1.8692   -0.1543 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1350    0.4596   -0.1774 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8683   -1.9509   -0.5107 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7022   -0.5363    0.6009 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7199   -0.3647   -0.8935 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8739    0.6346   -1.7174 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3049   -1.0282   -2.0132 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3928    0.1400    1.0903 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6494    2.1660   -1.0196 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3022    2.0131    0.6528 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5298   -1.5283   -0.6039 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1819   -0.1872   -1.5550 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1906    0.3850    2.1290 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7935   -1.2777    2.0464 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0455   -1.0528    1.9028 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8801   -1.8731    0.0434 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3596   -2.6582    0.5044 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5307   -2.1459   -1.1929 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7999    1.1324   -0.9909 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4619    1.0140    0.7425 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0742   -0.0314   -0.5602 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  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  1  0
 12 14  1  0
 12 15  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  2 19  1  0
  2 20  1  0
  6 21  1  1
  7 22  1  0
  7 23  1  0
 11 24  1  0
 11 25  1  0
 13 26  1  0
 13 27  1  0
 13 28  1  0
 14 29  1  0
 14 30  1  0
 14 31  1  0
 15 32  1  0
 15 33  1  0
 15 34  1  0
M  CHG  2  10  -1  12   1
M  END


  Mrv1652310061800332D          

 16 15  0  0  1  0            999 V2000
    0.1105    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6039   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2211   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6039    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6039    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1105    0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5395    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6039    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6039   -0.8250    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    1.5395    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2539   -0.0000    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   -1.3184    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1105    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1105   -0.4125    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  5  1  1  0  0  0  0
  8  6  1  0  0  0  0
  8  7  1  0  0  0  0
  9  6  1  0  0  0  0
 10  5  1  0  0  0  0
 11  2  1  0  0  0  0
 11  3  1  0  0  0  0
 11  4  1  0  0  0  0
 11  7  1  0  0  0  0
 12  9  2  0  0  0  0
 13  9  1  0  0  0  0
 14 10  2  0  0  0  0
  8 15  1  6  0  0  0
 15 10  1  0  0  0  0
  8 16  1  6  0  0  0
M  CHG  2  11   1  13  -1
M  END
> <DATABASE_ID>
HMDB0240784

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C10H19NO4/c1-5-10(14)15-8(6-9(12)13)7-11(2,3)4/h8H,5-7H2,1-4H3/t8-/m0/s1

> <INCHI_KEY>
UFAHZIUFPNSHSL-QMMMGPOBSA-N

> <FORMULA>
C10H19NO4

> <MOLECULAR_WEIGHT>
217.265

> <EXACT_MASS>
217.131408096

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
34

> <JCHEM_AVERAGE_POLARIZABILITY>
22.910785925922887

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3S)-3-(propanoyloxy)-4-(trimethylazaniumyl)butanoate

> <ALOGPS_LOGP>
-2.27

> <JCHEM_LOGP>
-3.7458447908050787

> <ALOGPS_LOGS>
-3.25

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.185139998188834

> <JCHEM_PKA_STRONGEST_BASIC>
-7.054133284063387

> <JCHEM_POLAR_SURFACE_AREA>
66.42999999999999

> <JCHEM_REFRACTIVITY>
77.2637

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.52e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
O-propanoyl-D-carnitine

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0240784
     RDKit          3D
O-Propanoyl-D-carnitine
 34 33  0  0  0  0  0  0  0  0999 V2000
    4.8093   -0.8407   -0.4707 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6213   -0.3147   -1.2081 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4374   -0.1777   -0.3081 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5765   -0.5042    0.8963 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2299    0.2885   -0.7682 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0742    0.4340    0.0778 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3913    1.8603    0.0408 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6293    2.8268    0.5095 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7593    2.4498    0.8918 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2960    4.1643    0.5126 O   0  0  0  0  0  1  0  0  0  0  0  0
   -0.9529   -0.4994   -0.4993 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2010   -0.5555    0.1944 N   0  0  0  0  0  4  0  0  0  0  0  0
   -2.0291   -0.5723    1.6326 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7865   -1.8692   -0.1543 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1350    0.4596   -0.1774 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8683   -1.9509   -0.5107 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7022   -0.5363    0.6009 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7199   -0.3647   -0.8935 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8739    0.6346   -1.7174 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3049   -1.0282   -2.0132 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3928    0.1400    1.0903 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6494    2.1660   -1.0196 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3022    2.0131    0.6528 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5298   -1.5283   -0.6039 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1819   -0.1872   -1.5550 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1906    0.3850    2.1290 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7935   -1.2777    2.0464 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0455   -1.0528    1.9028 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8801   -1.8731    0.0434 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3596   -2.6582    0.5044 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5307   -2.1459   -1.1929 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7999    1.1324   -0.9909 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4619    1.0140    0.7425 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0742   -0.0314   -0.5602 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  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  1  0
 12 14  1  0
 12 15  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  2 19  1  0
  2 20  1  0
  6 21  1  1
  7 22  1  0
  7 23  1  0
 11 24  1  0
 11 25  1  0
 13 26  1  0
 13 27  1  0
 13 28  1  0
 14 29  1  0
 14 30  1  0
 14 31  1  0
 15 32  1  0
 15 33  1  0
 15 34  1  0
M  CHG  2  10  -1  12   1
M  END

HEADER    PROTEIN                                 06-OCT-18   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-OCT-18         0                                  
HETATM    1  C   UNK     0       0.206   5.390   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.127  -3.080   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.667  -1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.413  -1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.127   4.620   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.540   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.127   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.206   0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.874   0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.127   3.080   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0      -1.127  -1.540   0.000  0.00  0.00           N+1
HETATM   12  O   UNK     0       2.874   2.310   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       4.207  -0.000   0.000  0.00  0.00           O-1
HETATM   14  O   UNK     0      -2.461   2.310   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       0.206   2.310   0.000  0.00  0.00           O+0
HETATM   16  H   UNK     0       0.206  -0.770   0.000  0.00  0.00           H+0
CONECT    1    5                                                            
CONECT    2   11                                                            
CONECT    3   11                                                            
CONECT    4   11                                                            
CONECT    5    1   10                                                       
CONECT    6    8    9                                                       
CONECT    7    8   11                                                       
CONECT    8    6    7   15   16                                             
CONECT    9    6   12   13                                                  
CONECT   10    5   14   15                                                  
CONECT   11    2    3    4    7                                             
CONECT   12    9                                                            
CONECT   13    9                                                            
CONECT   14   10                                                            
CONECT   15    8   10                                                       
CONECT   16    8                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   30    0
END

COMPND    HMDB0240784
HETATM    1  C1  UNL     1       4.809  -0.841  -0.471  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.621  -0.315  -1.208  1.00  0.00           C  
HETATM    3  C3  UNL     1       2.437  -0.178  -0.308  1.00  0.00           C  
HETATM    4  O1  UNL     1       2.576  -0.504   0.896  1.00  0.00           O  
HETATM    5  O2  UNL     1       1.230   0.288  -0.768  1.00  0.00           O  
HETATM    6  C4  UNL     1       0.074   0.434   0.078  1.00  0.00           C  
HETATM    7  C5  UNL     1      -0.391   1.860   0.041  1.00  0.00           C  
HETATM    8  C6  UNL     1       0.629   2.827   0.510  1.00  0.00           C  
HETATM    9  O3  UNL     1       1.759   2.450   0.892  1.00  0.00           O  
HETATM   10  O4  UNL     1       0.296   4.164   0.513  1.00  0.00           O1-
HETATM   11  C7  UNL     1      -0.953  -0.499  -0.499  1.00  0.00           C  
HETATM   12  N1  UNL     1      -2.201  -0.555   0.194  1.00  0.00           N1+
HETATM   13  C8  UNL     1      -2.029  -0.572   1.633  1.00  0.00           C  
HETATM   14  C9  UNL     1      -2.787  -1.869  -0.154  1.00  0.00           C  
HETATM   15  C10 UNL     1      -3.135   0.460  -0.177  1.00  0.00           C  
HETATM   16  H1  UNL     1       4.868  -1.951  -0.511  1.00  0.00           H  
HETATM   17  H2  UNL     1       4.702  -0.536   0.601  1.00  0.00           H  
HETATM   18  H3  UNL     1       5.720  -0.365  -0.893  1.00  0.00           H  
HETATM   19  H4  UNL     1       3.874   0.635  -1.717  1.00  0.00           H  
HETATM   20  H5  UNL     1       3.305  -1.028  -2.013  1.00  0.00           H  
HETATM   21  H6  UNL     1       0.393   0.140   1.090  1.00  0.00           H  
HETATM   22  H7  UNL     1      -0.649   2.166  -1.020  1.00  0.00           H  
HETATM   23  H8  UNL     1      -1.302   2.013   0.653  1.00  0.00           H  
HETATM   24  H9  UNL     1      -0.530  -1.528  -0.604  1.00  0.00           H  
HETATM   25  H10 UNL     1      -1.182  -0.187  -1.555  1.00  0.00           H  
HETATM   26  H11 UNL     1      -2.191   0.385   2.129  1.00  0.00           H  
HETATM   27  H12 UNL     1      -2.793  -1.278   2.046  1.00  0.00           H  
HETATM   28  H13 UNL     1      -1.046  -1.053   1.903  1.00  0.00           H  
HETATM   29  H14 UNL     1      -3.880  -1.873   0.043  1.00  0.00           H  
HETATM   30  H15 UNL     1      -2.360  -2.658   0.504  1.00  0.00           H  
HETATM   31  H16 UNL     1      -2.531  -2.146  -1.193  1.00  0.00           H  
HETATM   32  H17 UNL     1      -2.800   1.132  -0.991  1.00  0.00           H  
HETATM   33  H18 UNL     1      -3.462   1.014   0.742  1.00  0.00           H  
HETATM   34  H19 UNL     1      -4.074  -0.031  -0.560  1.00  0.00           H  
CONECT    1    2   16   17   18
CONECT    2    3   19   20
CONECT    3    4    4    5
CONECT    5    6
CONECT    6    7   11   21
CONECT    7    8   22   23
CONECT    8    9    9   10
CONECT   11   12   24   25
CONECT   12   13   14   15
CONECT   13   26   27   28
CONECT   14   29   30   31
CONECT   15   32   33   34
END

HMDB0240784
     RDKit          3D
O-Propanoyl-D-carnitine
 34 33  0  0  0  0  0  0  0  0999 V2000
    4.8093   -0.8407   -0.4707 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6213   -0.3147   -1.2081 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4374   -0.1777   -0.3081 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5765   -0.5042    0.8963 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2299    0.2885   -0.7682 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0742    0.4340    0.0778 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3913    1.8603    0.0408 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6293    2.8268    0.5095 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7593    2.4498    0.8918 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2960    4.1643    0.5126 O   0  0  0  0  0  1  0  0  0  0  0  0
   -0.9529   -0.4994   -0.4993 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2010   -0.5555    0.1944 N   0  0  0  0  0  4  0  0  0  0  0  0
   -2.0291   -0.5723    1.6326 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7865   -1.8692   -0.1543 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1350    0.4596   -0.1774 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8683   -1.9509   -0.5107 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7022   -0.5363    0.6009 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7199   -0.3647   -0.8935 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8739    0.6346   -1.7174 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3049   -1.0282   -2.0132 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3928    0.1400    1.0903 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6494    2.1660   -1.0196 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3022    2.0131    0.6528 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5298   -1.5283   -0.6039 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1819   -0.1872   -1.5550 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1906    0.3850    2.1290 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7935   -1.2777    2.0464 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0455   -1.0528    1.9028 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8801   -1.8731    0.0434 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3596   -2.6582    0.5044 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5307   -2.1459   -1.1929 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7999    1.1324   -0.9909 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4619    1.0140    0.7425 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0742   -0.0314   -0.5602 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  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  1  0
 12 14  1  0
 12 15  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  2 19  1  0
  2 20  1  0
  6 21  1  1
  7 22  1  0
  7 23  1  0
 11 24  1  0
 11 25  1  0
 13 26  1  0
 13 27  1  0
 13 28  1  0
 14 29  1  0
 14 30  1  0
 14 31  1  0
 15 32  1  0
 15 33  1  0
 15 34  1  0
M  CHG  2  10  -1  12   1
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₀H₁₉NO₄

Average Molecular Weight

217.265

Monoisotopic Molecular Weight

217.131408096

IUPAC Name

(3S)-3-(propanoyloxy)-4-(trimethylazaniumyl)butanoate

Traditional Name

O-propanoyl-D-carnitine

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C10H19NO4/c1-5-10(14)15-8(6-9(12)13)7-11(2,3)4/h8H,5-7H2,1-4H3/t8-/m0/s1

InChI Key

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

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

O-acyl-D-carnitine (CHEBI:53211 )

Ontology

Physiological effect

Health effect

Cancer

Breast cancer (PMID: 35710135)

Diabetes mellitus type 2 (PMID: 35710135)
Celiac disease (PMID: 35710135)
Inflammatory bowel disease (PMID: 35710135)

Circulatory system disorder

Cardiac disorder

Cardiovascular disease (PMID: 35710135)
Heart failure (PMID: 35710135)

Renal system and urinary system

Renal disorder

Renal cell carcinoma (PMID: 35710135)

Disposition

Biological location

Cell

All cells and tissues (PMID: 35710135)

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 35710135)

Excreta

Biofluid or Excreta

Urine (PMID: 35710135)

Cellular substructure

cytoplasm (PMID: 35710135)
mitochondrion matrix (PMID: 35710135)

Organelle

peroxisome (PMID: 35710135)

Source

Endogenous

Endogenous (HMDB: HMDB0240784)

Process

Not Available

Role

Biological role

Energy source (PMID: 35710135)

Industrial application

Pharmaceutical industry

Biomarker

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	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	-2.3	ALOGPS
logP	-3.7	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	4.19	ChemAxon
pKa (Strongest Basic)	-7.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	66.43 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	77.26 m³·mol⁻¹	ChemAxon
Polarizability	22.91 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]+	128.229	30932474
DeepCCS	[M-H]-	125.896	30932474
DeepCCS	[M-2H]-	159.232	30932474
DeepCCS	[M+Na]+	134.013	30932474
AllCCS	[M+H]+	150.8	32859911
AllCCS	[M+H-H2O]+	147.5	32859911
AllCCS	[M+NH4]+	153.8	32859911
AllCCS	[M+Na]+	154.7	32859911
AllCCS	[M-H]-	156.7	32859911
AllCCS	[M+Na-2H]-	157.8	32859911
AllCCS	[M+HCOO]-	159.2	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
O-Propanoyl-D-carnitine	[H][C@](CC([O-])=O)(C[N+](C)(C)C)OC(=O)CC	1906.9	Standard polar	33892256
O-Propanoyl-D-carnitine	[H][C@](CC([O-])=O)(C[N+](C)(C)C)OC(=O)CC	1206.4	Standard non polar	33892256
O-Propanoyl-D-carnitine	[H][C@](CC([O-])=O)(C[N+](C)(C)C)OC(=O)CC	1435.2	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 - O-Propanoyl-D-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 - O-Propanoyl-D-carnitine 10V, Positive-QTOF	splash10-014i-0090000000-183878d9af472b731f0f	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - O-Propanoyl-D-carnitine 20V, Positive-QTOF	splash10-00kr-9050000000-a5c35e074ce368a1496b	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - O-Propanoyl-D-carnitine 40V, Positive-QTOF	splash10-000i-9000000000-e9262cbaff8cb4ad0ba6	2021-09-22	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

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

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

12879828

PDB ID

Not Available

ChEBI ID

53211

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

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 ]
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 ]
Sud M, Fahy E, Cotter D, Brown A, Dennis EA, Glass CK, Merrill AH Jr, Murphy RC, Raetz CR, Russell DW, Subramaniam S: LMSD: LIPID MAPS structure database. Nucleic Acids Res. 2007 Jan;35(Database issue):D527-32. doi: 10.1093/nar/gkl838. Epub 2006 Nov 10. [PubMed:17098933 ]
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 ]
Kiykim E, Aktuglu Zeybek AC, Barut K, Zubarioglu T, Cansever MS, Alsancak S, Kasapcopur O: Screening of Free Carnitine and Acylcarnitine Status in Children With Familial Mediterranean Fever. Arch Rheumatol. 2016 Mar 10;31(2):133-138. doi: 10.5606/ArchRheumatol.2016.5696. eCollection 2016 Jun. [PubMed:29900937 ]
Adams SH, Hoppel CL, Lok KH, Zhao L, Wong SW, Minkler PE, Hwang DH, Newman JW, Garvey WT: Plasma acylcarnitine profiles suggest incomplete long-chain fatty acid beta-oxidation and altered tricarboxylic acid cycle activity in type 2 diabetic African-American women. J Nutr. 2009 Jun;139(6):1073-81. doi: 10.3945/jn.108.103754. Epub 2009 Apr 15. [PubMed:19369366 ]
Ueland T, Svardal A, Oie E, Askevold ET, Nymoen SH, Bjorndal B, Dahl CP, Gullestad L, Berge RK, Aukrust P: Disturbed carnitine regulation in chronic heart failure--increased plasma levels of palmitoyl-carnitine are associated with poor prognosis. Int J Cardiol. 2013 Sep 1;167(5):1892-9. doi: 10.1016/j.ijcard.2012.04.150. Epub 2012 May 22. [PubMed:22622056 ]
Han LS, Huang Z, Han F, Ye J, Qiu WJ, Zhang HW, Wang Y, Gong ZW, Gu XF: Clinical features and MUT gene mutation spectrum in Chinese patients with isolated methylmalonic acidemia: identification of ten novel allelic variants. World J Pediatr. 2015 Nov;11(4):358-65. doi: 10.1007/s12519-015-0043-1. Epub 2015 Oct 11. [PubMed:26454439 ]
Ghoraba DA, Mohammed MM, Zaki OK: Mutation analysis of methylmalonyl CoA mutase gene exon 2 in Egyptian families: Identification of 25 novel allelic variants. Meta Gene. 2015 Feb 25;3:71-88. doi: 10.1016/j.mgene.2014.02.001. eCollection 2015 Feb. [PubMed:25750861 ]
Kang L, Liu Y, Shen M, Liu Y, He R, Song J, Jin Y, Li M, Zhang Y, Dong H, Liu X, Yan H, Qin J, Zheng H, Chen Y, Li D, Wei H, Zhang H, Sun L, Zhu Z, Liang D, Yang Y: A study on a cohort of 301 Chinese patients with isolated methylmalonic acidemia. J Inherit Metab Dis. 2020 May;43(3):409-423. doi: 10.1002/jimd.12183. Epub 2019 Nov 26. [PubMed:31622506 ]
Keyfi F, Abbaszadegan MR, Sankian M, Rolfs A, Orolicki S, Pournasrollah M, Alijanpour M, Varasteh A: Mutation analysis of genes related to methylmalonic acidemia: identification of eight novel mutations. Mol Biol Rep. 2019 Feb;46(1):271-285. doi: 10.1007/s11033-018-4469-0. Epub 2019 Feb 2. [PubMed:30712249 ]
Curnock R, Heaton ND, Vilca-Melendez H, Dhawan A, Hadzic N, Vara R: Liver Transplantation in Children With Propionic Acidemia: Medium-Term Outcomes. Liver Transpl. 2020 Mar;26(3):419-430. doi: 10.1002/lt.25679. Epub 2020 Feb 3. [PubMed:31715057 ]
Monostori P, Klinke G, Richter S, Barath A, Fingerhut R, Baumgartner MR, Kolker S, Hoffmann GF, Gramer G, Okun JG: Simultaneous determination of 3-hydroxypropionic acid, methylmalonic acid and methylcitric acid in dried blood spots: Second-tier LC-MS/MS assay for newborn screening of propionic acidemia, methylmalonic acidemias and combined remethylation disorders. PLoS One. 2017 Sep 15;12(9):e0184897. doi: 10.1371/journal.pone.0184897. eCollection 2017. [PubMed:28915261 ]
Libert DM, Nowacki AS, Natowicz MR: Metabolomic analysis of obesity, metabolic syndrome, and type 2 diabetes: amino acid and acylcarnitine levels change along a spectrum of metabolic wellness. PeerJ. 2018 Aug 31;6:e5410. doi: 10.7717/peerj.5410. eCollection 2018. [PubMed:30186675 ]
Rahmandar MH, Bawcom A, Romano ME, Hamid R: Cobalamin C deficiency in an adolescent with altered mental status and anorexia. Pediatrics. 2014 Dec;134(6):e1709-14. doi: 10.1542/peds.2013-2711. Epub 2014 Nov 3. [PubMed:25367534 ]
Dambrova M, Makrecka-Kuka M, Kuka J, Vilskersts R, Nordberg D, Attwood MM, Smesny S, Sen ZD, Guo AC, Oler E, Tian S, Zheng J, Wishart DS, Liepinsh E, Schioth HB: Acylcarnitines: Nomenclature, Biomarkers, Therapeutic Potential, Drug Targets, and Clinical Trials. Pharmacol Rev. 2022 Jul;74(3):506-551. doi: 10.1124/pharmrev.121.000408. [PubMed:35710135 ]

Showing metabocard for O-Propanoyl-D-carnitine (HMDB0240784)

MOL for HMDB0240784 (O-Propanoyl-D-carnitine)

3D MOL for HMDB0240784 (O-Propanoyl-D-carnitine)

3D SDF for HMDB0240784 (O-Propanoyl-D-carnitine)

3D-SDF for HMDB0240784 (O-Propanoyl-D-carnitine)

PDB for HMDB0240784 (O-Propanoyl-D-carnitine)

3D PDB for HMDB0240784 (O-Propanoyl-D-carnitine)

SMILES for HMDB0240784 (O-Propanoyl-D-carnitine)

INCHI for HMDB0240784 (O-Propanoyl-D-carnitine)

Structure for HMDB0240784 (O-Propanoyl-D-carnitine)

3D Structure for HMDB0240784 (O-Propanoyl-D-carnitine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra