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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-02-24 01:48:33 UTC

Update Date

2022-10-24 19:44:18 UTC

HMDB ID

HMDB0240781

Secondary Accession Numbers

None

Metabolite Identification

Common Name

O-Methylmalonylcarnitine

Description

O-Methylmalonylcarnitine is an acylcarnitine. More specifically, it is an methylmalonic 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-Methylmalonylcarnitine is therefore classified as a short chain AC. As a short-chain acylcarnitine O-Methylmalonylcarnitine 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. 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

HMDB0240781
     RDKit          3D
O-Methylmalonylcarnitine
 37 36  0  0  0  0  0  0  0  0999 V2000
   -4.5127    0.0768    1.0121 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5463   -0.3059   -0.0857 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6021   -1.7634   -0.3048 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0503   -2.4822    0.6232 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1932   -2.3994   -1.4671 O   0  0  0  0  0  1  0  0  0  0  0  0
   -2.1732    0.1689    0.2231 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9936    0.7923    1.2941 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1007   -0.0461   -0.6112 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1888    0.4330   -0.2787 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6945    1.2713   -1.3599 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2008    2.4279   -1.5892 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2553    2.6706   -0.9545 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1182    3.3586   -2.5923 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9870   -0.7854    0.0646 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3343   -0.6300    0.4431 N   0  0  0  0  0  4  0  0  0  0  0  0
    2.6470   -1.7959    1.3046 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6544    0.5241    1.2404 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2794   -0.8083   -0.6618 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3698   -0.6363    0.9553 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8608    1.1188    0.8557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0311   -0.0512    1.9872 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9410    0.1637   -1.0151 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0879    1.0183    0.6556 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6975    1.7183   -1.2111 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7692    0.7629   -2.3573 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0982    4.3494   -2.4129 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4333   -1.3073    0.8748 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9404   -1.4712   -0.8150 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0777   -1.6199    2.2331 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1886   -2.6675    0.7957 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7247   -1.9003    1.4574 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1498    1.3392    0.6573 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7648    0.8782    1.7992 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4093    0.2772    2.0468 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2498   -1.1327   -0.2374 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9034   -1.6212   -1.3044 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4327    0.0744   -1.2647 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
  2  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
  9 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
  9 23  1  0
 10 24  1  0
 10 25  1  0
 13 26  1  0
 14 27  1  0
 14 28  1  0
 16 29  1  0
 16 30  1  0
 16 31  1  0
 17 32  1  0
 17 33  1  0
 17 34  1  0
 18 35  1  0
 18 36  1  0
 18 37  1  0
M  CHG  2   5  -1  15   1
M  END


  Mrv1652310061800322D          

 18 17  0  0  0  0            999 V2000
    1.2375   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0954   -0.9355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9204   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2704   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3809    1.9520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0954    0.7145    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
    3.3809    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0954    2.3645    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
    1.9520    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0954   -0.1105    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    4.0954    3.1895    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8099    1.9520    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1914    0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5230    1.9520    0.0000 O   0  5  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
  7  1  1  0  0  0  0
  8  5  1  0  0  0  0
  8  6  1  0  0  0  0
  9  5  1  0  0  0  0
 10  7  1  0  0  0  0
 11  7  1  0  0  0  0
 12  2  1  0  0  0  0
 12  3  1  0  0  0  0
 12  4  1  0  0  0  0
 12  6  1  0  0  0  0
 13  9  2  0  0  0  0
 14  9  1  0  0  0  0
 15 10  2  0  0  0  0
 16 10  1  0  0  0  0
 17 11  2  0  0  0  0
 18  8  1  0  0  0  0
 18 11  1  0  0  0  0
M  CHG  2  12   1  16  -1
M  END
> <DATABASE_ID>
HMDB0240781

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C11H19NO6/c1-7(10(15)16)11(17)18-8(5-9(13)14)6-12(2,3)4/h7-8H,5-6H2,1-4H3,(H-,13,14,15,16)

> <INCHI_KEY>
XROYFEWIXXCPAW-UHFFFAOYSA-N

> <FORMULA>
C11H19NO6

> <MOLECULAR_WEIGHT>
261.274

> <EXACT_MASS>
261.121237336

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
37

> <JCHEM_AVERAGE_POLARIZABILITY>
25.601886354855708

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-{[1-carboxy-3-(trimethylazaniumyl)propan-2-yl]oxy}-2-methyl-3-oxopropanoate

> <ALOGPS_LOGP>
-1.76

> <JCHEM_LOGP>
-4.0111659134717454

> <ALOGPS_LOGS>
-3.05

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
4.23841297010917

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.534250036378786

> <JCHEM_PKA_STRONGEST_BASIC>
-7.208415042403216

> <JCHEM_POLAR_SURFACE_AREA>
103.73

> <JCHEM_REFRACTIVITY>
83.5554

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.83e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-{[1-carboxy-3-(trimethylammonio)propan-2-yl]oxy}-2-methyl-3-oxopropanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0240781
     RDKit          3D
O-Methylmalonylcarnitine
 37 36  0  0  0  0  0  0  0  0999 V2000
   -4.5127    0.0768    1.0121 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5463   -0.3059   -0.0857 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6021   -1.7634   -0.3048 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0503   -2.4822    0.6232 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1932   -2.3994   -1.4671 O   0  0  0  0  0  1  0  0  0  0  0  0
   -2.1732    0.1689    0.2231 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9936    0.7923    1.2941 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1007   -0.0461   -0.6112 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1888    0.4330   -0.2787 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6945    1.2713   -1.3599 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2008    2.4279   -1.5892 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2553    2.6706   -0.9545 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1182    3.3586   -2.5923 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9870   -0.7854    0.0646 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3343   -0.6300    0.4431 N   0  0  0  0  0  4  0  0  0  0  0  0
    2.6470   -1.7959    1.3046 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6544    0.5241    1.2404 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2794   -0.8083   -0.6618 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3698   -0.6363    0.9553 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8608    1.1188    0.8557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0311   -0.0512    1.9872 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9410    0.1637   -1.0151 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0879    1.0183    0.6556 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6975    1.7183   -1.2111 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7692    0.7629   -2.3573 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0982    4.3494   -2.4129 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4333   -1.3073    0.8748 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9404   -1.4712   -0.8150 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0777   -1.6199    2.2331 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1886   -2.6675    0.7957 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7247   -1.9003    1.4574 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1498    1.3392    0.6573 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7648    0.8782    1.7992 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4093    0.2772    2.0468 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2498   -1.1327   -0.2374 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9034   -1.6212   -1.3044 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4327    0.0744   -1.2647 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
  2  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
  9 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
  9 23  1  0
 10 24  1  0
 10 25  1  0
 13 26  1  0
 14 27  1  0
 14 28  1  0
 16 29  1  0
 16 30  1  0
 16 31  1  0
 17 32  1  0
 17 33  1  0
 17 34  1  0
 18 35  1  0
 18 36  1  0
 18 37  1  0
M  CHG  2   5  -1  15   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       2.310  -0.206   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.645  -1.746   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.185  -0.206   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.105  -0.206   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.311   3.644   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.645   1.334   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.310   1.334   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.311   2.104   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.645   4.414   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.976   2.104   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.644   2.104   0.000  0.00  0.00           C+0
HETATM   12  N   UNK     0       7.645  -0.206   0.000  0.00  0.00           N+1
HETATM   13  O   UNK     0       7.645   5.954   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       8.978   3.644   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0      -0.357   1.334   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       0.976   3.644   0.000  0.00  0.00           O-1
HETATM   17  O   UNK     0       3.644   3.644   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       4.977   1.334   0.000  0.00  0.00           O+0
CONECT    1    7                                                            
CONECT    2   12                                                            
CONECT    3   12                                                            
CONECT    4   12                                                            
CONECT    5    8    9                                                       
CONECT    6    8   12                                                       
CONECT    7    1   10   11                                                  
CONECT    8    5    6   18                                                  
CONECT    9    5   13   14                                                  
CONECT   10    7   15   16                                                  
CONECT   11    7   17   18                                                  
CONECT   12    2    3    4    6                                             
CONECT   13    9                                                            
CONECT   14    9                                                            
CONECT   15   10                                                            
CONECT   16   10                                                            
CONECT   17   11                                                            
CONECT   18    8   11                                                       
MASTER        0    0    0    0    0    0    0    0   18    0   34    0
END

COMPND    HMDB0240781
HETATM    1  C1  UNL     1      -4.513   0.077   1.012  1.00  0.00           C  
HETATM    2  C2  UNL     1      -3.546  -0.306  -0.086  1.00  0.00           C  
HETATM    3  C3  UNL     1      -3.602  -1.763  -0.305  1.00  0.00           C  
HETATM    4  O1  UNL     1      -4.050  -2.482   0.623  1.00  0.00           O  
HETATM    5  O2  UNL     1      -3.193  -2.399  -1.467  1.00  0.00           O1-
HETATM    6  C4  UNL     1      -2.173   0.169   0.223  1.00  0.00           C  
HETATM    7  O3  UNL     1      -1.994   0.792   1.294  1.00  0.00           O  
HETATM    8  O4  UNL     1      -1.101  -0.046  -0.611  1.00  0.00           O  
HETATM    9  C5  UNL     1       0.189   0.433  -0.279  1.00  0.00           C  
HETATM   10  C6  UNL     1       0.694   1.271  -1.360  1.00  0.00           C  
HETATM   11  C7  UNL     1      -0.201   2.428  -1.589  1.00  0.00           C  
HETATM   12  O5  UNL     1      -1.255   2.671  -0.955  1.00  0.00           O  
HETATM   13  O6  UNL     1       0.118   3.359  -2.592  1.00  0.00           O  
HETATM   14  C8  UNL     1       0.987  -0.785   0.065  1.00  0.00           C  
HETATM   15  N1  UNL     1       2.334  -0.630   0.443  1.00  0.00           N1+
HETATM   16  C9  UNL     1       2.647  -1.796   1.305  1.00  0.00           C  
HETATM   17  C10 UNL     1       2.654   0.524   1.240  1.00  0.00           C  
HETATM   18  C11 UNL     1       3.279  -0.808  -0.662  1.00  0.00           C  
HETATM   19  H1  UNL     1      -5.370  -0.636   0.955  1.00  0.00           H  
HETATM   20  H2  UNL     1      -4.861   1.119   0.856  1.00  0.00           H  
HETATM   21  H3  UNL     1      -4.031  -0.051   1.987  1.00  0.00           H  
HETATM   22  H4  UNL     1      -3.941   0.164  -1.015  1.00  0.00           H  
HETATM   23  H5  UNL     1       0.088   1.018   0.656  1.00  0.00           H  
HETATM   24  H6  UNL     1       1.697   1.718  -1.211  1.00  0.00           H  
HETATM   25  H7  UNL     1       0.769   0.763  -2.357  1.00  0.00           H  
HETATM   26  H8  UNL     1       0.098   4.349  -2.413  1.00  0.00           H  
HETATM   27  H9  UNL     1       0.433  -1.307   0.875  1.00  0.00           H  
HETATM   28  H10 UNL     1       0.940  -1.471  -0.815  1.00  0.00           H  
HETATM   29  H11 UNL     1       2.078  -1.620   2.233  1.00  0.00           H  
HETATM   30  H12 UNL     1       2.189  -2.667   0.796  1.00  0.00           H  
HETATM   31  H13 UNL     1       3.725  -1.900   1.457  1.00  0.00           H  
HETATM   32  H14 UNL     1       3.150   1.339   0.657  1.00  0.00           H  
HETATM   33  H15 UNL     1       1.765   0.878   1.799  1.00  0.00           H  
HETATM   34  H16 UNL     1       3.409   0.277   2.047  1.00  0.00           H  
HETATM   35  H17 UNL     1       4.250  -1.133  -0.237  1.00  0.00           H  
HETATM   36  H18 UNL     1       2.903  -1.621  -1.304  1.00  0.00           H  
HETATM   37  H19 UNL     1       3.433   0.074  -1.265  1.00  0.00           H  
CONECT    1    2   19   20   21
CONECT    2    3    6   22
CONECT    3    4    4    5
CONECT    6    7    7    8
CONECT    8    9
CONECT    9   10   14   23
CONECT   10   11   24   25
CONECT   11   12   12   13
CONECT   13   26
CONECT   14   15   27   28
CONECT   15   16   17   18
CONECT   16   29   30   31
CONECT   17   32   33   34
CONECT   18   35   36   37
END

HMDB0240781
     RDKit          3D
O-Methylmalonylcarnitine
 37 36  0  0  0  0  0  0  0  0999 V2000
   -4.5127    0.0768    1.0121 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5463   -0.3059   -0.0857 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6021   -1.7634   -0.3048 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0503   -2.4822    0.6232 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1932   -2.3994   -1.4671 O   0  0  0  0  0  1  0  0  0  0  0  0
   -2.1732    0.1689    0.2231 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9936    0.7923    1.2941 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1007   -0.0461   -0.6112 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1888    0.4330   -0.2787 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6945    1.2713   -1.3599 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2008    2.4279   -1.5892 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2553    2.6706   -0.9545 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1182    3.3586   -2.5923 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9870   -0.7854    0.0646 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3343   -0.6300    0.4431 N   0  0  0  0  0  4  0  0  0  0  0  0
    2.6470   -1.7959    1.3046 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6544    0.5241    1.2404 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2794   -0.8083   -0.6618 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3698   -0.6363    0.9553 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8608    1.1188    0.8557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0311   -0.0512    1.9872 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9410    0.1637   -1.0151 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0879    1.0183    0.6556 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6975    1.7183   -1.2111 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7692    0.7629   -2.3573 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0982    4.3494   -2.4129 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4333   -1.3073    0.8748 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9404   -1.4712   -0.8150 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0777   -1.6199    2.2331 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1886   -2.6675    0.7957 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7247   -1.9003    1.4574 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1498    1.3392    0.6573 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7648    0.8782    1.7992 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4093    0.2772    2.0468 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2498   -1.1327   -0.2374 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9034   -1.6212   -1.3044 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4327    0.0744   -1.2647 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
  2  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
  9 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
  9 23  1  0
 10 24  1  0
 10 25  1  0
 13 26  1  0
 14 27  1  0
 14 28  1  0
 16 29  1  0
 16 30  1  0
 16 31  1  0
 17 32  1  0
 17 33  1  0
 17 34  1  0
 18 35  1  0
 18 36  1  0
 18 37  1  0
M  CHG  2   5  -1  15   1
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
2-Methylmalonyl carnitine	ChEBI
2-Methylmalonyl-D-carnitine	ChEBI
2-Methylmalonylcarnitine	ChEBI
3-[(2-Carboxypropanoyl)oxy]-4-(trimethylammonio)butanoate	ChEBI
Methylmalonylcarnitine	ChEBI
3-[(2-Carboxypropanoyl)oxy]-4-(trimethylammonio)butanoic acid	Generator

Chemical Formula

C₁₁H₁₉NO₆

Average Molecular Weight

261.274

Monoisotopic Molecular Weight

261.121237336

IUPAC Name

3-{[1-carboxy-3-(trimethylazaniumyl)propan-2-yl]oxy}-2-methyl-3-oxopropanoate

Traditional Name

3-{[1-carboxy-3-(trimethylammonio)propan-2-yl]oxy}-2-methyl-3-oxopropanoate

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C11H19NO6/c1-7(10(15)16)11(17)18-8(5-9(13)14)6-12(2,3)4/h7-8H,5-6H2,1-4H3,(H-,13,14,15,16)

InChI Key

XROYFEWIXXCPAW-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
Tricarboxylic acid or derivatives
1,3-dicarbonyl compound
Quaternary ammonium salt
Tetraalkylammonium salt
Carboxylic acid salt
Carboxylic acid ester
Carboxylic acid
Carboxylic acid derivative
Hydrocarbon derivative
Organic salt
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Organooxygen compound
Organonitrogen compound
Carbonyl group
Amine
Organic oxide
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

carboxylic ester (CHEBI:73031 )
O-acylcarnitine (CHEBI:73031 )
ammonium betaine (CHEBI:73031 )

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: HMDB0240781)

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	-1.8	ALOGPS
logP	-4	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	3.53	ChemAxon
pKa (Strongest Basic)	-7.2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	103.73 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	83.56 m³·mol⁻¹	ChemAxon
Polarizability	25.6 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]+	151.747	30932474
DeepCCS	[M-H]-	149.388	30932474
DeepCCS	[M-2H]-	183.181	30932474
DeepCCS	[M+Na]+	158.41	30932474
AllCCS	[M+H]+	157.9	32859911
AllCCS	[M+H-H2O]+	154.9	32859911
AllCCS	[M+NH4]+	160.6	32859911
AllCCS	[M+Na]+	161.4	32859911
AllCCS	[M-H]-	164.7	32859911
AllCCS	[M+Na-2H]-	165.6	32859911
AllCCS	[M+HCOO]-	166.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
O-Methylmalonylcarnitine	CC(C([O-])=O)C(=O)OC(CC(O)=O)C[N+](C)(C)C	2821.5	Standard polar	33892256
O-Methylmalonylcarnitine	CC(C([O-])=O)C(=O)OC(CC(O)=O)C[N+](C)(C)C	1367.5	Standard non polar	33892256
O-Methylmalonylcarnitine	CC(C([O-])=O)C(=O)OC(CC(O)=O)C[N+](C)(C)C	1755.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
O-Methylmalonylcarnitine,1TMS,isomer #1	CC(C(=O)[O-])C(=O)OC(CC(=O)O[Si](C)(C)C)C[N+](C)(C)C	1689.0	Semi standard non polar	33892256
O-Methylmalonylcarnitine,1TBDMS,isomer #1	CC(C(=O)[O-])C(=O)OC(CC(=O)O[Si](C)(C)C(C)(C)C)C[N+](C)(C)C	1932.5	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-Methylmalonylcarnitine 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-Methylmalonylcarnitine 10V, Positive-QTOF	splash10-03di-0090000000-48d875468ed156af31be	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - O-Methylmalonylcarnitine 20V, Positive-QTOF	splash10-01p9-9050000000-49b1ecee6d2effc4a365	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - O-Methylmalonylcarnitine 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

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Cancer patients undergoing total body irradiation	31424920	details
Urine	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Cancer patients undergoing total body irradiation	31424920	details

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

21403178

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

71464478

PDB ID

Not Available

ChEBI ID

73031

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

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 ]
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 ]
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-Methylmalonylcarnitine (HMDB0240781)

MOL for HMDB0240781 (O-Methylmalonylcarnitine)

3D MOL for HMDB0240781 (O-Methylmalonylcarnitine)

3D SDF for HMDB0240781 (O-Methylmalonylcarnitine)

3D-SDF for HMDB0240781 (O-Methylmalonylcarnitine)

PDB for HMDB0240781 (O-Methylmalonylcarnitine)

3D PDB for HMDB0240781 (O-Methylmalonylcarnitine)

SMILES for HMDB0240781 (O-Methylmalonylcarnitine)

INCHI for HMDB0240781 (O-Methylmalonylcarnitine)

Structure for HMDB0240781 (O-Methylmalonylcarnitine)

3D Structure for HMDB0240781 (O-Methylmalonylcarnitine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra