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Record Information

Version

5.0

Status

Predicted

Creation Date

2021-03-31 19:31:33 UTC

Update Date

2022-10-24 19:45:19 UTC

HMDB ID

HMDB0241681

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Hept-3-enoylcarnitine

Description

Hept-3-enoylcarnitine is an acylcarnitine. More specifically, it is an hept-3-enoic 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. Hept-3-enoylcarnitine is therefore classified as a medium chain AC. As a medium-chain acylcarnitine Hept-3-enoylcarnitine is somewhat less abundant than short-chain acylcarnitines. These are formed either through esterification with L-carnitine or through the peroxisomal metabolism of longer chain acylcarnitines (PMID: 30540494 ). Many medium-chain acylcarnitines can serve as useful markers for inherited disorders of fatty acid metabolism. Carnitine octanoyltransferase (CrOT, EC:2.3.1.137) is responsible for the synthesis of all medium-chain (MCAC, C5-C12) and medium-length branched-chain acylcarnitines in peroxisomes (PMID: 10486279 ). 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

HMDB0241681
     RDKit          3D
Hept-3-enoylcarnitine
 44 43  0  0  0  0  0  0  0  0999 V2000
    5.8907   -0.0381    0.3108 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4689   -0.9375   -0.8601 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9553   -0.8104   -0.9665 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2698   -1.2371    0.2513 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5175   -0.5088    0.9971 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2271    0.9129    0.7283 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7838    1.1824    0.5208 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2851    2.2346    1.0563 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0903    0.4097   -0.1975 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4848    0.7730   -0.3395 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7141    0.8092   -1.8335 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8703    1.7659   -2.5589 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0523    2.4759   -1.9698 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0638    1.8103   -3.9524 O   0  0  0  0  0  1  0  0  0  0  0  0
   -2.2167   -0.3842    0.2829 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6137   -0.3530    0.3388 N   0  0  0  0  0  4  0  0  0  0  0  0
   -4.2706   -1.0262   -0.7605 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2171    0.9432    0.5149 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0139   -1.1420    1.5298 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3392    0.9318    0.2256 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9696    0.2383    0.2283 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6405   -0.5751    1.2303 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9018   -0.4728   -1.7737 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7996   -1.9631   -0.7255 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6139   -1.5407   -1.7786 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6459    0.1653   -1.3490 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4319   -2.2990    0.5380 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0697   -0.9976    1.8914 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5418    1.4929    1.6670 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8843    1.2916   -0.0423 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6093    1.7131    0.1786 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5063   -0.1925   -2.2979 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8021    0.9734   -2.0261 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7751   -0.5334    1.3090 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8948   -1.3019   -0.2906 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5382   -1.7459   -1.1874 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6972   -0.3479   -1.5243 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1403   -1.6391   -0.4183 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6041    1.6238    1.1353 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5417    1.3905   -0.4497 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1677    0.7842    1.0728 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9832   -2.2129    1.2885 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0369   -0.8029    1.8145 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3318   -0.8601    2.3577 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  3
  5  6  1  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 10 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
 16 19  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  2 23  1  0
  2 24  1  0
  3 25  1  0
  3 26  1  0
  4 27  1  0
  5 28  1  0
  6 29  1  0
  6 30  1  0
 10 31  1  0
 11 32  1  0
 11 33  1  0
 15 34  1  0
 15 35  1  0
 17 36  1  0
 17 37  1  0
 17 38  1  0
 18 39  1  0
 18 40  1  0
 18 41  1  0
 19 42  1  0
 19 43  1  0
 19 44  1  0
M  CHG  2  14  -1  16   1
M  END


  Mrv1652303312121312D          

 19 18  0  0  0  0            999 V2000
   -1.3184   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6039   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6039    0.0000    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    0.1105   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250   -0.8250    0.0000 C   0  0  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
    1.5395   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2539   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9684   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6829   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3974   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1118   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8263   -2.0625    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
    1.5395    0.4125    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    1.9520   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2539    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
 10  9  1  4  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
  5 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 16 19  1  0  0  0  0
M  CHG  2   3  -1  16   1
M  END
> <DATABASE_ID>
HMDB0241681

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C14H25NO4/c1-5-6-7-8-9-14(18)19-12(10-13(16)17)11-15(2,3)4/h7-8,12H,5-6,9-11H2,1-4H3

> <INCHI_KEY>
UWDRQAPTJQRMKT-UHFFFAOYSA-N

> <FORMULA>
C14H25NO4

> <MOLECULAR_WEIGHT>
271.357

> <EXACT_MASS>
271.178358289

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
44

> <JCHEM_AVERAGE_POLARIZABILITY>
30.026502595735458

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-(hept-3-enoyloxy)-4-(trimethylazaniumyl)butanoate

> <JCHEM_LOGP>
-2.3294917874717447

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.171787604062307

> <JCHEM_PKA_STRONGEST_BASIC>
-7.103906609878612

> <JCHEM_POLAR_SURFACE_AREA>
66.43

> <JCHEM_REFRACTIVITY>
96.7843

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
3-(hept-3-enoyloxy)-4-(trimethylammonio)butanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0241681
     RDKit          3D
Hept-3-enoylcarnitine
 44 43  0  0  0  0  0  0  0  0999 V2000
    5.8907   -0.0381    0.3108 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4689   -0.9375   -0.8601 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9553   -0.8104   -0.9665 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2698   -1.2371    0.2513 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5175   -0.5088    0.9971 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2271    0.9129    0.7283 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7838    1.1824    0.5208 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2851    2.2346    1.0563 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0903    0.4097   -0.1975 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4848    0.7730   -0.3395 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7141    0.8092   -1.8335 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8703    1.7659   -2.5589 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0523    2.4759   -1.9698 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0638    1.8103   -3.9524 O   0  0  0  0  0  1  0  0  0  0  0  0
   -2.2167   -0.3842    0.2829 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6137   -0.3530    0.3388 N   0  0  0  0  0  4  0  0  0  0  0  0
   -4.2706   -1.0262   -0.7605 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2171    0.9432    0.5149 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0139   -1.1420    1.5298 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3392    0.9318    0.2256 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9696    0.2383    0.2283 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6405   -0.5751    1.2303 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9018   -0.4728   -1.7737 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7996   -1.9631   -0.7255 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6139   -1.5407   -1.7786 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6459    0.1653   -1.3490 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4319   -2.2990    0.5380 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0697   -0.9976    1.8914 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5418    1.4929    1.6670 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8843    1.2916   -0.0423 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6093    1.7131    0.1786 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5063   -0.1925   -2.2979 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8021    0.9734   -2.0261 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7751   -0.5334    1.3090 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8948   -1.3019   -0.2906 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5382   -1.7459   -1.1874 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6972   -0.3479   -1.5243 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1403   -1.6391   -0.4183 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6041    1.6238    1.1353 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5417    1.3905   -0.4497 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1677    0.7842    1.0728 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9832   -2.2129    1.2885 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0369   -0.8029    1.8145 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3318   -0.8601    2.3577 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  3
  5  6  1  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 10 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
 16 19  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  2 23  1  0
  2 24  1  0
  3 25  1  0
  3 26  1  0
  4 27  1  0
  5 28  1  0
  6 29  1  0
  6 30  1  0
 10 31  1  0
 11 32  1  0
 11 33  1  0
 15 34  1  0
 15 35  1  0
 17 36  1  0
 17 37  1  0
 17 38  1  0
 18 39  1  0
 18 40  1  0
 18 41  1  0
 19 42  1  0
 19 43  1  0
 19 44  1  0
M  CHG  2  14  -1  16   1
M  END

HEADER    PROTEIN                                 31-MAR-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   31-MAR-21         0                                  
HETATM    1  O   UNK     0      -2.461  -2.310   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -1.127  -1.540   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -1.127   0.000   0.000  0.00  0.00           O-1
HETATM    4  C   UNK     0       0.206  -2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.540  -1.540   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       2.874  -2.310   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       2.874  -3.850   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       1.540  -4.620   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       4.207  -4.620   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.541  -3.850   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.875  -4.620   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.208  -3.850   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.542  -4.620   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.876  -3.850   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.540   0.000   0.000  0.00  0.00           C+0
HETATM   16  N   UNK     0       2.874   0.770   0.000  0.00  0.00           N+1
HETATM   17  C   UNK     0       3.644  -0.564   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.104   2.104   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.207   1.540   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   15                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13                                                            
CONECT   15    5   16                                                       
CONECT   16   15   17   18   19                                             
CONECT   17   16                                                            
CONECT   18   16                                                            
CONECT   19   16                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   36    0
END

COMPND    HMDB0241681
HETATM    1  C1  UNL     1       5.891  -0.038   0.311  1.00  0.00           C  
HETATM    2  C2  UNL     1       5.469  -0.937  -0.860  1.00  0.00           C  
HETATM    3  C3  UNL     1       3.955  -0.810  -0.967  1.00  0.00           C  
HETATM    4  C4  UNL     1       3.270  -1.237   0.251  1.00  0.00           C  
HETATM    5  C5  UNL     1       2.518  -0.509   0.997  1.00  0.00           C  
HETATM    6  C6  UNL     1       2.227   0.913   0.728  1.00  0.00           C  
HETATM    7  C7  UNL     1       0.784   1.182   0.521  1.00  0.00           C  
HETATM    8  O1  UNL     1       0.285   2.235   1.056  1.00  0.00           O  
HETATM    9  O2  UNL     1      -0.090   0.410  -0.197  1.00  0.00           O  
HETATM   10  C8  UNL     1      -1.485   0.773  -0.339  1.00  0.00           C  
HETATM   11  C9  UNL     1      -1.714   0.809  -1.834  1.00  0.00           C  
HETATM   12  C10 UNL     1      -0.870   1.766  -2.559  1.00  0.00           C  
HETATM   13  O3  UNL     1      -0.052   2.476  -1.970  1.00  0.00           O  
HETATM   14  O4  UNL     1      -1.064   1.810  -3.952  1.00  0.00           O1-
HETATM   15  C11 UNL     1      -2.217  -0.384   0.283  1.00  0.00           C  
HETATM   16  N1  UNL     1      -3.614  -0.353   0.339  1.00  0.00           N1+
HETATM   17  C12 UNL     1      -4.271  -1.026  -0.761  1.00  0.00           C  
HETATM   18  C13 UNL     1      -4.217   0.943   0.515  1.00  0.00           C  
HETATM   19  C14 UNL     1      -4.014  -1.142   1.530  1.00  0.00           C  
HETATM   20  H1  UNL     1       5.339   0.932   0.226  1.00  0.00           H  
HETATM   21  H2  UNL     1       6.970   0.238   0.228  1.00  0.00           H  
HETATM   22  H3  UNL     1       5.641  -0.575   1.230  1.00  0.00           H  
HETATM   23  H4  UNL     1       5.902  -0.473  -1.774  1.00  0.00           H  
HETATM   24  H5  UNL     1       5.800  -1.963  -0.726  1.00  0.00           H  
HETATM   25  H6  UNL     1       3.614  -1.541  -1.779  1.00  0.00           H  
HETATM   26  H7  UNL     1       3.646   0.165  -1.349  1.00  0.00           H  
HETATM   27  H8  UNL     1       3.432  -2.299   0.538  1.00  0.00           H  
HETATM   28  H9  UNL     1       2.070  -0.998   1.891  1.00  0.00           H  
HETATM   29  H10 UNL     1       2.542   1.493   1.667  1.00  0.00           H  
HETATM   30  H11 UNL     1       2.884   1.292  -0.042  1.00  0.00           H  
HETATM   31  H12 UNL     1      -1.609   1.713   0.179  1.00  0.00           H  
HETATM   32  H13 UNL     1      -1.506  -0.192  -2.298  1.00  0.00           H  
HETATM   33  H14 UNL     1      -2.802   0.973  -2.026  1.00  0.00           H  
HETATM   34  H15 UNL     1      -1.775  -0.533   1.309  1.00  0.00           H  
HETATM   35  H16 UNL     1      -1.895  -1.302  -0.291  1.00  0.00           H  
HETATM   36  H17 UNL     1      -3.538  -1.746  -1.187  1.00  0.00           H  
HETATM   37  H18 UNL     1      -4.697  -0.348  -1.524  1.00  0.00           H  
HETATM   38  H19 UNL     1      -5.140  -1.639  -0.418  1.00  0.00           H  
HETATM   39  H20 UNL     1      -3.604   1.624   1.135  1.00  0.00           H  
HETATM   40  H21 UNL     1      -4.542   1.391  -0.450  1.00  0.00           H  
HETATM   41  H22 UNL     1      -5.168   0.784   1.073  1.00  0.00           H  
HETATM   42  H23 UNL     1      -3.983  -2.213   1.289  1.00  0.00           H  
HETATM   43  H24 UNL     1      -5.037  -0.803   1.814  1.00  0.00           H  
HETATM   44  H25 UNL     1      -3.332  -0.860   2.358  1.00  0.00           H  
CONECT    1    2   20   21   22
CONECT    2    3   23   24
CONECT    3    4   25   26
CONECT    4    5    5   27
CONECT    5    6   28
CONECT    6    7   29   30
CONECT    7    8    8    9
CONECT    9   10
CONECT   10   11   15   31
CONECT   11   12   32   33
CONECT   12   13   13   14
CONECT   15   16   34   35
CONECT   16   17   18   19
CONECT   17   36   37   38
CONECT   18   39   40   41
CONECT   19   42   43   44
END

HMDB0241681
     RDKit          3D
Hept-3-enoylcarnitine
 44 43  0  0  0  0  0  0  0  0999 V2000
    5.8907   -0.0381    0.3108 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4689   -0.9375   -0.8601 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9553   -0.8104   -0.9665 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2698   -1.2371    0.2513 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5175   -0.5088    0.9971 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2271    0.9129    0.7283 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7838    1.1824    0.5208 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2851    2.2346    1.0563 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0903    0.4097   -0.1975 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4848    0.7730   -0.3395 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7141    0.8092   -1.8335 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8703    1.7659   -2.5589 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0523    2.4759   -1.9698 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0638    1.8103   -3.9524 O   0  0  0  0  0  1  0  0  0  0  0  0
   -2.2167   -0.3842    0.2829 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6137   -0.3530    0.3388 N   0  0  0  0  0  4  0  0  0  0  0  0
   -4.2706   -1.0262   -0.7605 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2171    0.9432    0.5149 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0139   -1.1420    1.5298 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3392    0.9318    0.2256 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9696    0.2383    0.2283 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6405   -0.5751    1.2303 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9018   -0.4728   -1.7737 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7996   -1.9631   -0.7255 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6139   -1.5407   -1.7786 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6459    0.1653   -1.3490 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4319   -2.2990    0.5380 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0697   -0.9976    1.8914 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5418    1.4929    1.6670 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8843    1.2916   -0.0423 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6093    1.7131    0.1786 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5063   -0.1925   -2.2979 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8021    0.9734   -2.0261 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7751   -0.5334    1.3090 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8948   -1.3019   -0.2906 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5382   -1.7459   -1.1874 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6972   -0.3479   -1.5243 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1403   -1.6391   -0.4183 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6041    1.6238    1.1353 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5417    1.3905   -0.4497 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1677    0.7842    1.0728 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9832   -2.2129    1.2885 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0369   -0.8029    1.8145 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3318   -0.8601    2.3577 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  3
  5  6  1  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 10 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
 16 19  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  2 23  1  0
  2 24  1  0
  3 25  1  0
  3 26  1  0
  4 27  1  0
  5 28  1  0
  6 29  1  0
  6 30  1  0
 10 31  1  0
 11 32  1  0
 11 33  1  0
 15 34  1  0
 15 35  1  0
 17 36  1  0
 17 37  1  0
 17 38  1  0
 18 39  1  0
 18 40  1  0
 18 41  1  0
 19 42  1  0
 19 43  1  0
 19 44  1  0
M  CHG  2  14  -1  16   1
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
3-(Hept-3-enoyloxy)-4-(trimethylazaniumyl)butanoic acid	Generator

Chemical Formula

C₁₄H₂₅NO₄

Average Molecular Weight

271.357

Monoisotopic Molecular Weight

271.178358289

IUPAC Name

3-(hept-3-enoyloxy)-4-(trimethylazaniumyl)butanoate

Traditional Name

3-(hept-3-enoyloxy)-4-(trimethylammonio)butanoate

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C14H25NO4/c1-5-6-7-8-9-14(18)19-12(10-13(16)17)11-15(2,3)4/h7-8,12H,5-6,9-11H2,1-4H3

InChI Key

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

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

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)

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	ChemAxon
pKa (Strongest Acidic)	4.17	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	10	ChemAxon
Refractivity	96.78 m³·mol⁻¹	ChemAxon
Polarizability	30.03 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]+	159.697	30932474
DeepCCS	[M-H]-	157.339	30932474
DeepCCS	[M-2H]-	190.222	30932474
DeepCCS	[M+Na]+	165.79	30932474

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Hept-3-enoylcarnitine	CCCC=CCC(=O)OC(CC([O-])=O)C[N+](C)(C)C	2302.5	Standard polar	33892256
Hept-3-enoylcarnitine	CCCC=CCC(=O)OC(CC([O-])=O)C[N+](C)(C)C	1567.5	Standard non polar	33892256
Hept-3-enoylcarnitine	CCCC=CCC(=O)OC(CC([O-])=O)C[N+](C)(C)C	1772.6	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 - Hept-3-enoylcarnitine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Hept-3-enoylcarnitine 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 - Hept-3-enoylcarnitine 10V, Positive-QTOF	Not Available	2021-04-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hept-3-enoylcarnitine 20V, Positive-QTOF	Not Available	2021-04-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hept-3-enoylcarnitine 40V, Positive-QTOF	Not Available	2021-04-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hept-3-enoylcarnitine 10V, Positive-QTOF	splash10-00di-0090000000-9d1d789db49a0744e234	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hept-3-enoylcarnitine 20V, Positive-QTOF	splash10-0079-9050000000-5d4572165f8c7d9e4b84	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hept-3-enoylcarnitine 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)	2021-09-25	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

Name	SMPDB/PathBank	KEGG
Acylcarnitine hept-3-enoylcarnitine		Not Available

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

Not Available

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

Ferdinandusse S, Mulders J, IJlst L, Denis S, Dacremont G, Waterham HR, Wanders RJ: Molecular cloning and expression of human carnitine octanoyltransferase: evidence for its role in the peroxisomal beta-oxidation of branched-chain fatty acids. Biochem Biophys Res Commun. 1999 Sep 16;263(1):213-8. [PubMed:10486279 ]
Blazenovic I, Kind T, Sa MR, Ji J, Vaniya A, Wancewicz B, Roberts BS, Torbasinovic H, Lee T, Mehta SS, Showalter MR, Song H, Kwok J, Jahn D, Kim J, Fiehn O: Structure Annotation of All Mass Spectra in Untargeted Metabolomics. Anal Chem. 2019 Feb 5;91(3):2155-2162. doi: 10.1021/acs.analchem.8b04698. Epub 2019 Jan 16. [PubMed:30608141 ]
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 ]
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Showing metabocard for Hept-3-enoylcarnitine (HMDB0241681)

MOL for HMDB0241681 (Hept-3-enoylcarnitine)

3D MOL for HMDB0241681 (Hept-3-enoylcarnitine)

3D SDF for HMDB0241681 (Hept-3-enoylcarnitine)

3D-SDF for HMDB0241681 (Hept-3-enoylcarnitine)

PDB for HMDB0241681 (Hept-3-enoylcarnitine)

3D PDB for HMDB0241681 (Hept-3-enoylcarnitine)

SMILES for HMDB0241681 (Hept-3-enoylcarnitine)

INCHI for HMDB0241681 (Hept-3-enoylcarnitine)

Structure for HMDB0241681 (Hept-3-enoylcarnitine)

3D Structure for HMDB0241681 (Hept-3-enoylcarnitine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra