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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2014-04-16 20:46:53 UTC

Update Date

2021-09-14 15:46:31 UTC

HMDB ID

HMDB0061717

Secondary Accession Numbers

HMDB61717

Metabolite Identification

Common Name

Succinylcarnitine

Description

Succinylcarnitine is an acylcarnitine. More specifically, it is an succinic 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 [Dambrova et al. 2021, Physiological Reviews], 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. Succinylcarnitine is therefore classified as a short chain AC. As a short-chain acylcarnitine Succinylcarnitine 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 ), it has been identified in the human placenta (PMID: 32033212 ). 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 at [Dambrova et al. 2021, Physiological Reviews].

Structure

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

HMDB0061717
     RDKit          3D
Succinylcarnitine
 37 36  0  0  0  0  0  0  0  0999 V2000
   -2.6715   -1.2687   -1.0348 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5835   -0.6079    0.2305 N   0  0  0  0  0  4  0  0  0  0  0  0
   -2.9881   -1.5946    1.2533 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6555    0.3837    0.2495 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3250   -0.0991    0.6206 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3179    0.2033   -0.4067 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6420    1.3700   -1.3263 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8029    2.6531   -0.6112 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5961    2.8695    0.3318 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0123    3.7704   -0.9880 O   0  0  0  0  0  1  0  0  0  0  0  0
    0.8539    0.6819    0.2955 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0867    0.0539    0.1607 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1102   -0.9438   -0.6026 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3024    0.5554    0.8934 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5100   -0.2608    0.5906 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8006   -0.1997   -0.8561 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0752    0.4744   -1.6097 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8927   -0.9101   -1.3423 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7359   -1.7700   -1.3228 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1096   -0.6448   -1.8423 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4311   -2.1009   -0.9184 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9843   -1.9795    1.0691 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2649   -2.4518    1.1542 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8279   -1.1946    2.2730 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6876    0.9184    1.2288 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5886    1.0748   -0.6169 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6281   -0.1395    0.1533 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5232    0.7986    1.2824 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8449   -0.8356    1.3333 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0807   -0.6650   -1.0206 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2370    1.4690   -1.9970 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5786    1.2055   -1.8944 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0796    0.6637    1.9605 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4624    1.6039    0.4983 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3480    0.1399    1.2051 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3111   -1.3071    0.9179 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8107   -1.9160   -1.3519 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
 16 17  2  0
 16 18  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  3 22  1  0
  3 23  1  0
  3 24  1  0
  4 25  1  0
  4 26  1  0
  4 27  1  0
  5 28  1  0
  5 29  1  0
  6 30  1  6
  7 31  1  0
  7 32  1  0
 14 33  1  0
 14 34  1  0
 15 35  1  0
 15 36  1  0
 18 37  1  0
M  CHG  2   2   1  10  -1
M  END


  Mrv1652311301722152D          

 18 17  0  0  0  0            999 V2000
 2499.3901 2499.4665    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 2500.1046 2499.8790    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2500.8191 2499.4665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2501.5335 2499.8790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2502.2480 2499.4665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2502.9625 2499.8790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2503.6770 2499.4665    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2502.9625 2500.7040    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2500.8191 2498.6415    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2498.6757 2499.8790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2498.6757 2500.7040    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
 2498.6757 2501.5290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2499.5007 2500.7040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2497.8507 2500.7040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2499.3901 2498.6415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2498.6757 2498.2290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2497.9612 2498.6415    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
 2498.6757 2497.4040    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  6  0  0  0
  1 10  1  0  0  0  0
  1 15  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3  9  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 11 14  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  2  0  0  0  0
M  CHG  2  11   1  17  -1
M  END
> <DATABASE_ID>
HMDB0061717

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C11H19NO6/c1-12(2,3)7-8(6-10(15)16)18-11(17)5-4-9(13)14/h8H,4-7H2,1-3H3,(H-,13,14,15,16)/t8-/m1/s1

> <INCHI_KEY>
HAEVNYBCYZZDFL-MRVPVSSYSA-N

> <FORMULA>
C11H19NO6

> <MOLECULAR_WEIGHT>
261.274

> <EXACT_MASS>
261.121237336

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
37

> <JCHEM_AVERAGE_POLARIZABILITY>
25.66773789203814

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3R)-3-[(3-carboxypropanoyl)oxy]-4-(trimethylazaniumyl)butanoate

> <ALOGPS_LOGP>
-2.06

> <JCHEM_LOGP>
-4.6215178908050785

> <ALOGPS_LOGS>
-3.00

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
4.323360316633482

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.631341988732754

> <JCHEM_PKA_STRONGEST_BASIC>
-7.062957248961382

> <JCHEM_POLAR_SURFACE_AREA>
103.72999999999999

> <JCHEM_REFRACTIVITY>
83.5301

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.16e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3R)-3-[(3-carboxypropanoyl)oxy]-4-(trimethylammonio)butanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0061717
     RDKit          3D
Succinylcarnitine
 37 36  0  0  0  0  0  0  0  0999 V2000
   -2.6715   -1.2687   -1.0348 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5835   -0.6079    0.2305 N   0  0  0  0  0  4  0  0  0  0  0  0
   -2.9881   -1.5946    1.2533 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6555    0.3837    0.2495 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3250   -0.0991    0.6206 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3179    0.2033   -0.4067 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6420    1.3700   -1.3263 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8029    2.6531   -0.6112 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5961    2.8695    0.3318 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0123    3.7704   -0.9880 O   0  0  0  0  0  1  0  0  0  0  0  0
    0.8539    0.6819    0.2955 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0867    0.0539    0.1607 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1102   -0.9438   -0.6026 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3024    0.5554    0.8934 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5100   -0.2608    0.5906 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8006   -0.1997   -0.8561 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0752    0.4744   -1.6097 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8927   -0.9101   -1.3423 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7359   -1.7700   -1.3228 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1096   -0.6448   -1.8423 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4311   -2.1009   -0.9184 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9843   -1.9795    1.0691 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2649   -2.4518    1.1542 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8279   -1.1946    2.2730 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6876    0.9184    1.2288 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5886    1.0748   -0.6169 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6281   -0.1395    0.1533 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5232    0.7986    1.2824 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8449   -0.8356    1.3333 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0807   -0.6650   -1.0206 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2370    1.4690   -1.9970 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5786    1.2055   -1.8944 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0796    0.6637    1.9605 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4624    1.6039    0.4983 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3480    0.1399    1.2051 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3111   -1.3071    0.9179 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8107   -1.9160   -1.3519 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
 16 17  2  0
 16 18  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  3 22  1  0
  3 23  1  0
  3 24  1  0
  4 25  1  0
  4 26  1  0
  4 27  1  0
  5 28  1  0
  5 29  1  0
  6 30  1  6
  7 31  1  0
  7 32  1  0
 14 33  1  0
 14 34  1  0
 15 35  1  0
 15 36  1  0
 18 37  1  0
M  CHG  2   2   1  10  -1
M  END

HEADER    PROTEIN                                 30-NOV-17   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   30-NOV-17         0                                  
HETATM    1  C   UNK     0    4665.5284665.671   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0    4666.8624666.441   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0    4668.1964665.671   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    4669.5294666.441   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0    4670.8634665.671   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    4672.1974666.441   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0    4673.5304665.671   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0    4672.1974667.981   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0    4668.1964664.131   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0    4664.1954666.441   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0    4664.1954667.981   0.000  0.00  0.00           N+1
HETATM   12  C   UNK     0    4664.1954669.521   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    4665.7354667.981   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    4662.6554667.981   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    4665.5284664.131   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    4664.1954663.361   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0    4662.8614664.131   0.000  0.00  0.00           O-1
HETATM   18  O   UNK     0    4664.1954661.821   0.000  0.00  0.00           O+0
CONECT    1    2   10   15                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4    9                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6                                                            
CONECT    9    3                                                            
CONECT   10    1   11                                                       
CONECT   11   10   12   13   14                                             
CONECT   12   11                                                            
CONECT   13   11                                                            
CONECT   14   11                                                            
CONECT   15    1   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   34    0
END

COMPND    HMDB0061717
HETATM    1  C1  UNL     1      -2.672  -1.269  -1.035  1.00  0.00           C  
HETATM    2  N1  UNL     1      -2.584  -0.608   0.231  1.00  0.00           N1+
HETATM    3  C2  UNL     1      -2.988  -1.595   1.253  1.00  0.00           C  
HETATM    4  C3  UNL     1      -3.656   0.384   0.249  1.00  0.00           C  
HETATM    5  C4  UNL     1      -1.325  -0.099   0.621  1.00  0.00           C  
HETATM    6  C5  UNL     1      -0.318   0.203  -0.407  1.00  0.00           C  
HETATM    7  C6  UNL     1      -0.642   1.370  -1.326  1.00  0.00           C  
HETATM    8  C7  UNL     1      -0.803   2.653  -0.611  1.00  0.00           C  
HETATM    9  O1  UNL     1      -1.596   2.870   0.332  1.00  0.00           O  
HETATM   10  O2  UNL     1      -0.012   3.770  -0.988  1.00  0.00           O1-
HETATM   11  O3  UNL     1       0.854   0.682   0.295  1.00  0.00           O  
HETATM   12  C8  UNL     1       2.087   0.054   0.161  1.00  0.00           C  
HETATM   13  O4  UNL     1       2.110  -0.944  -0.603  1.00  0.00           O  
HETATM   14  C9  UNL     1       3.302   0.555   0.893  1.00  0.00           C  
HETATM   15  C10 UNL     1       4.510  -0.261   0.591  1.00  0.00           C  
HETATM   16  C11 UNL     1       4.801  -0.200  -0.856  1.00  0.00           C  
HETATM   17  O5  UNL     1       4.075   0.474  -1.610  1.00  0.00           O  
HETATM   18  O6  UNL     1       5.893  -0.910  -1.342  1.00  0.00           O  
HETATM   19  H1  UNL     1      -1.736  -1.770  -1.323  1.00  0.00           H  
HETATM   20  H2  UNL     1      -3.110  -0.645  -1.842  1.00  0.00           H  
HETATM   21  H3  UNL     1      -3.431  -2.101  -0.918  1.00  0.00           H  
HETATM   22  H4  UNL     1      -3.984  -1.979   1.069  1.00  0.00           H  
HETATM   23  H5  UNL     1      -2.265  -2.452   1.154  1.00  0.00           H  
HETATM   24  H6  UNL     1      -2.828  -1.195   2.273  1.00  0.00           H  
HETATM   25  H7  UNL     1      -3.688   0.918   1.229  1.00  0.00           H  
HETATM   26  H8  UNL     1      -3.589   1.075  -0.617  1.00  0.00           H  
HETATM   27  H9  UNL     1      -4.628  -0.140   0.153  1.00  0.00           H  
HETATM   28  H10 UNL     1      -1.523   0.799   1.282  1.00  0.00           H  
HETATM   29  H11 UNL     1      -0.845  -0.836   1.333  1.00  0.00           H  
HETATM   30  H12 UNL     1      -0.081  -0.665  -1.021  1.00  0.00           H  
HETATM   31  H13 UNL     1       0.237   1.469  -1.997  1.00  0.00           H  
HETATM   32  H14 UNL     1      -1.579   1.206  -1.894  1.00  0.00           H  
HETATM   33  H15 UNL     1       3.080   0.664   1.961  1.00  0.00           H  
HETATM   34  H16 UNL     1       3.462   1.604   0.498  1.00  0.00           H  
HETATM   35  H17 UNL     1       5.348   0.140   1.205  1.00  0.00           H  
HETATM   36  H18 UNL     1       4.311  -1.307   0.918  1.00  0.00           H  
HETATM   37  H19 UNL     1       5.811  -1.916  -1.352  1.00  0.00           H  
CONECT    1    2   19   20   21
CONECT    2    3    4    5
CONECT    3   22   23   24
CONECT    4   25   26   27
CONECT    5    6   28   29
CONECT    6    7   11   30
CONECT    7    8   31   32
CONECT    8    9    9   10
CONECT   11   12
CONECT   12   13   13   14
CONECT   14   15   33   34
CONECT   15   16   35   36
CONECT   16   17   17   18
CONECT   18   37
END

HMDB0061717
     RDKit          3D
Succinylcarnitine
 37 36  0  0  0  0  0  0  0  0999 V2000
   -2.6715   -1.2687   -1.0348 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5835   -0.6079    0.2305 N   0  0  0  0  0  4  0  0  0  0  0  0
   -2.9881   -1.5946    1.2533 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6555    0.3837    0.2495 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3250   -0.0991    0.6206 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3179    0.2033   -0.4067 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6420    1.3700   -1.3263 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8029    2.6531   -0.6112 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5961    2.8695    0.3318 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0123    3.7704   -0.9880 O   0  0  0  0  0  1  0  0  0  0  0  0
    0.8539    0.6819    0.2955 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0867    0.0539    0.1607 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1102   -0.9438   -0.6026 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3024    0.5554    0.8934 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5100   -0.2608    0.5906 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8006   -0.1997   -0.8561 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0752    0.4744   -1.6097 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8927   -0.9101   -1.3423 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7359   -1.7700   -1.3228 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1096   -0.6448   -1.8423 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4311   -2.1009   -0.9184 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9843   -1.9795    1.0691 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2649   -2.4518    1.1542 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8279   -1.1946    2.2730 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6876    0.9184    1.2288 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5886    1.0748   -0.6169 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6281   -0.1395    0.1533 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5232    0.7986    1.2824 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8449   -0.8356    1.3333 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0807   -0.6650   -1.0206 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2370    1.4690   -1.9970 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5786    1.2055   -1.8944 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0796    0.6637    1.9605 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4624    1.6039    0.4983 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3480    0.1399    1.2051 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3111   -1.3071    0.9179 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8107   -1.9160   -1.3519 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
 16 17  2  0
 16 18  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  3 22  1  0
  3 23  1  0
  3 24  1  0
  4 25  1  0
  4 26  1  0
  4 27  1  0
  5 28  1  0
  5 29  1  0
  6 30  1  6
  7 31  1  0
  7 32  1  0
 14 33  1  0
 14 34  1  0
 15 35  1  0
 15 36  1  0
 18 37  1  0
M  CHG  2   2   1  10  -1
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
O-Succinylcarnitine	HMDB

Chemical Formula

C₁₁H₁₉NO₆

Average Molecular Weight

261.274

Monoisotopic Molecular Weight

261.121237336

IUPAC Name

(3R)-3-[(3-carboxypropanoyl)oxy]-4-(trimethylazaniumyl)butanoate

Traditional Name

(3R)-3-[(3-carboxypropanoyl)oxy]-4-(trimethylammonio)butanoate

CAS Registry Number

256928-74-2

SMILES

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

InChI Identifier

InChI=1S/C11H19NO6/c1-12(2,3)7-8(6-10(15)16)18-11(17)5-4-9(13)14/h8H,4-7H2,1-3H3,(H-,13,14,15,16)/t8-/m1/s1

InChI Key

HAEVNYBCYZZDFL-MRVPVSSYSA-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
Tetraalkylammonium salt
Quaternary ammonium salt
Carboxylic acid ester
Carboxylic acid salt
Carboxylic acid derivative
Carboxylic acid
Organic nitrogen compound
Organic salt
Organooxygen compound
Organonitrogen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Carbonyl group
Amine
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Ontology

Disposition

Biological location

Non-excretory biofluid

Blood
Saliva

Excreta

Feces
Urine

Organ

Placenta

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
Water Solubility	0.32 g/L	ALOGPS
logP	-2.1	ALOGPS
logP	-4.6	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	3.63	ChemAxon
pKa (Strongest Basic)	-7.1	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	9	ChemAxon
Refractivity	83.53 m³·mol⁻¹	ChemAxon
Polarizability	25.67 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]+	158.672	30932474
DeepCCS	[M-H]-	156.313	30932474
DeepCCS	[M-2H]-	189.199	30932474
DeepCCS	[M+Na]+	164.765	30932474
AllCCS	[M+H]+	160.2	32859911
AllCCS	[M+H-H2O]+	157.3	32859911
AllCCS	[M+NH4]+	163.0	32859911
AllCCS	[M+Na]+	163.8	32859911
AllCCS	[M-H]-	165.1	32859911
AllCCS	[M+Na-2H]-	166.0	32859911
AllCCS	[M+HCOO]-	167.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Succinylcarnitine	C[N+](C)(C)C[C@@H](CC([O-])=O)OC(=O)CCC(O)=O	2991.8	Standard polar	33892256
Succinylcarnitine	C[N+](C)(C)C[C@@H](CC([O-])=O)OC(=O)CCC(O)=O	1393.8	Standard non polar	33892256
Succinylcarnitine	C[N+](C)(C)C[C@@H](CC([O-])=O)OC(=O)CCC(O)=O	1851.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Succinylcarnitine,1TMS,isomer #1	C[N+](C)(C)C[C@@H](CC(=O)[O-])OC(=O)CCC(=O)O[Si](C)(C)C	1846.2	Semi standard non polar	33892256
Succinylcarnitine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CCC(=O)O[C@H](CC(=O)[O-])C[N+](C)(C)C	2094.4	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 - Succinylcarnitine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Succinylcarnitine 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 - Succinylcarnitine 10V, Positive-QTOF	splash10-03di-0090000000-48d875468ed156af31be	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Succinylcarnitine 20V, Positive-QTOF	splash10-01p9-9050000000-49b1ecee6d2effc4a365	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Succinylcarnitine 40V, Positive-QTOF	splash10-000i-9000000000-e9262cbaff8cb4ad0ba6	2021-09-24	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood
Feces
Saliva
Urine

Tissue Locations

Placenta

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	29808030	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	27543620	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details

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

62896353

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

131802075

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
Van Hove JL, Saenz MS, Thomas JA, Gallagher RC, Lovell MA, Fenton LZ, Shanske S, Myers SM, Wanders RJ, Ruiter J, Turkenburg M, Waterham HR: Succinyl-CoA ligase deficiency: a mitochondrial hepatoencephalomyopathy. Pediatr Res. 2010 Aug;68(2):159-64. doi: 10.1203/00006450-201011001-00310. [PubMed:20453710 ]
Jaberi E, Chitsazian F, Ali Shahidi G, Rohani M, Sina F, Safari I, Malakouti Nejad M, Houshmand M, Klotzle B, Elahi E: The novel mutation p.Asp251Asn in the beta-subunit of succinate-CoA ligase causes encephalomyopathy and elevated succinylcarnitine. J Hum Genet. 2013 Aug;58(8):526-30. doi: 10.1038/jhg.2013.45. Epub 2013 Jun 13. [PubMed:23759946 ]
Huffman KM, Koves TR, Hubal MJ, Abouassi H, Beri N, Bateman LA, Stevens RD, Ilkayeva OR, Hoffman EP, Muoio DM, Kraus WE: Metabolite signatures of exercise training in human skeletal muscle relate to mitochondrial remodelling and cardiometabolic fitness. Diabetologia. 2014 Nov;57(11):2282-95. doi: 10.1007/s00125-014-3343-4. Epub 2014 Aug 5. [PubMed:25091629 ]
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 ]
Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]
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 ]
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Showing metabocard for Succinylcarnitine (HMDB0061717)

MOL for HMDB0061717 (Succinylcarnitine)

3D MOL for HMDB0061717 (Succinylcarnitine)

3D SDF for HMDB0061717 (Succinylcarnitine)

3D-SDF for HMDB0061717 (Succinylcarnitine)

PDB for HMDB0061717 (Succinylcarnitine)

3D PDB for HMDB0061717 (Succinylcarnitine)

SMILES for HMDB0061717 (Succinylcarnitine)

INCHI for HMDB0061717 (Succinylcarnitine)

Structure for HMDB0061717 (Succinylcarnitine)

3D Structure for HMDB0061717 (Succinylcarnitine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra