MiMeDB: Showing metabocard for (2E)-Dodecenoyl-CoA (MMDBc0029729)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-17 23:39:15 UTC

Update Date

2024-04-30 19:41:32 UTC

Metabolite ID

MMDBc0029729

Metabolite Identification

Common Name

(2E)-Dodecenoyl-CoA

Description

(2E)-Dodecenoyl-CoA is an intermediate in fatty acid metabolism, the substrate of the enzyme acyl-CoA oxidase [EC-1.3.3.6], and enzymes acyl-CoA dehydrogenase, long-chain-acyl-CoA dehydrogenase [EC 1.3.99.3-1.3.99.13]. It is also an intermediate in fatty acid elongation, being the substrate of the enzyme enoyl-CoA hydratase and [EC 4.2.1.17]. (KEGG)

Structure

MOL SDF PDB SMILES InChI


  Mrv1652305221921022D          

 68 70  0  0  1  0            999 V2000
   -0.6066   21.4059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2222   22.6434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5722   22.6434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1078   21.8184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8223   21.4059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5368   21.8184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2512   21.4059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9657   21.8184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6802   21.4059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3946   21.8184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1091   21.4059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8236   21.8184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5381   21.4059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5394   21.8184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2538   21.4059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3959   21.4059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6815   21.8184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5407   27.1809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3972   23.4684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7120   29.3612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0714   30.0535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2551   27.5934    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.8249   21.4059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2525   21.8184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3771   30.3311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5608   27.8709    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   18.0088   27.2578    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   14.3972   21.8184    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   20.1308   30.6666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2909   29.5106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6828   21.4059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1483   28.5854    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   14.3972   22.6434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2170   31.4871    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.1104   21.8184    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.9683   21.8184    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.7982   30.1817    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.9583   29.0256    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.6234   30.6666    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.4839   29.3390    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.8249   20.5809    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    7.2525   22.6434    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.3813   27.7847    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.1117   21.4059    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.6828   20.5809    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   17.0152   26.5119    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   18.1193   25.2857    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   16.9541   25.3468    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.2387   25.2289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.4137   26.6578    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.9367   24.7059    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.2867   24.7059    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.5407   26.3559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.1117   23.8809    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.3414   28.4138    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.1803   26.4508    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.1117   25.5309    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.5672   25.8988    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   15.8262   25.9434    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   15.1117   24.7059    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    7.9670   21.4059    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.8236   22.6434    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5381   20.5809    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   17.2983   26.7695    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   18.8565   27.1007    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   17.8373   28.0648    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.6828   22.2309    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   18.9722   28.6285    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  4  1  1  0  0  0  0
  5  4  1  0  0  0  0
  6  5  1  0  0  0  0
  7  6  1  0  0  0  0
  8  7  1  0  0  0  0
  9  8  1  0  0  0  0
 10  9  1  0  0  0  0
 11 10  1  0  0  0  0
 12 11  1  0  0  0  0
 13 12  2  0  0  0  0
 15 14  1  0  0  0  0
 17 16  1  0  0  0  0
 22 18  1  1  0  0  0
 23 14  1  0  0  0  0
 24 13  1  0  0  0  0
 27 22  1  0  0  0  0
 27 26  1  0  0  0  0
 29 25  2  0  0  0  0
 30 25  1  0  0  0  0
 31 28  1  0  0  0  0
 32 26  1  0  0  0  0
 33  2  1  0  0  0  0
 33  3  1  0  0  0  0
 33 19  1  0  0  0  0
 33 28  1  0  0  0  0
 34 29  1  0  0  0  0
 35 16  1  4  0  0  0
 35 23  2  0  0  0  0
 36 15  1  4  0  0  0
 36 31  2  0  0  0  0
 37 20  2  0  0  0  0
 37 29  1  0  0  0  0
 38 20  1  0  0  0  0
 38 30  2  0  0  0  0
 39 21  2  0  0  0  0
 39 25  1  0  0  0  0
 40 21  1  0  0  0  0
 40 30  1  0  0  0  0
 32 40  1  1  0  0  0
 41 23  1  0  0  0  0
 42 24  2  0  0  0  0
 26 43  1  6  0  0  0
 28 44  1  6  0  0  0
 45 31  1  0  0  0  0
 53 18  1  0  0  0  0
 54 19  1  0  0  0  0
 55 22  1  0  0  0  0
 55 32  1  0  0  0  0
 27 56  1  1  0  0  0
 58 46  1  0  0  0  0
 58 47  1  0  0  0  0
 58 48  2  0  0  0  0
 58 56  1  0  0  0  0
 59 49  1  0  0  0  0
 59 50  2  0  0  0  0
 59 53  1  0  0  0  0
 59 57  1  0  0  0  0
 60 51  1  0  0  0  0
 60 52  2  0  0  0  0
 60 54  1  0  0  0  0
 60 57  1  0  0  0  0
 61 17  1  0  0  0  0
 61 24  1  0  0  0  0
 62 12  1  0  0  0  0
 63 13  1  0  0  0  0
 22 64  1  6  0  0  0
 26 65  1  1  0  0  0
 27 66  1  1  0  0  0
 28 67  1  6  0  0  0
 32 68  1  6  0  0  0
M  CHG  4  41  -1  45  -1  46  -1  47  -1
M  END


  Mrv1652305221921022D          

 68 70  0  0  1  0            999 V2000
   -0.6066   21.4059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2222   22.6434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5722   22.6434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1078   21.8184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8223   21.4059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5368   21.8184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2512   21.4059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9657   21.8184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6802   21.4059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3946   21.8184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1091   21.4059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8236   21.8184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5381   21.4059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5394   21.8184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2538   21.4059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3959   21.4059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6815   21.8184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5407   27.1809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3972   23.4684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7120   29.3612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0714   30.0535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2551   27.5934    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.8249   21.4059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2525   21.8184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3771   30.3311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5608   27.8709    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   18.0088   27.2578    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   14.3972   21.8184    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   20.1308   30.6666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2909   29.5106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6828   21.4059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1483   28.5854    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   14.3972   22.6434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2170   31.4871    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.1104   21.8184    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.9683   21.8184    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.7982   30.1817    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.9583   29.0256    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.6234   30.6666    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.4839   29.3390    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.8249   20.5809    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    7.2525   22.6434    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.3813   27.7847    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.1117   21.4059    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.6828   20.5809    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   17.0152   26.5119    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   18.1193   25.2857    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   16.9541   25.3468    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.2387   25.2289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.4137   26.6578    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.9367   24.7059    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.2867   24.7059    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.5407   26.3559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.1117   23.8809    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.3414   28.4138    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.1803   26.4508    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.1117   25.5309    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.5672   25.8988    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   15.8262   25.9434    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   15.1117   24.7059    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    7.9670   21.4059    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.8236   22.6434    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5381   20.5809    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   17.2983   26.7695    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   18.8565   27.1007    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   17.8373   28.0648    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.6828   22.2309    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   18.9722   28.6285    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  4  1  1  0  0  0  0
  5  4  1  0  0  0  0
  6  5  1  0  0  0  0
  7  6  1  0  0  0  0
  8  7  1  0  0  0  0
  9  8  1  0  0  0  0
 10  9  1  0  0  0  0
 11 10  1  0  0  0  0
 12 11  1  0  0  0  0
 13 12  2  0  0  0  0
 15 14  1  0  0  0  0
 17 16  1  0  0  0  0
 22 18  1  1  0  0  0
 23 14  1  0  0  0  0
 24 13  1  0  0  0  0
 27 22  1  0  0  0  0
 27 26  1  0  0  0  0
 29 25  2  0  0  0  0
 30 25  1  0  0  0  0
 31 28  1  0  0  0  0
 32 26  1  0  0  0  0
 33  2  1  0  0  0  0
 33  3  1  0  0  0  0
 33 19  1  0  0  0  0
 33 28  1  0  0  0  0
 34 29  1  0  0  0  0
 35 16  1  4  0  0  0
 35 23  2  0  0  0  0
 36 15  1  4  0  0  0
 36 31  2  0  0  0  0
 37 20  2  0  0  0  0
 37 29  1  0  0  0  0
 38 20  1  0  0  0  0
 38 30  2  0  0  0  0
 39 21  2  0  0  0  0
 39 25  1  0  0  0  0
 40 21  1  0  0  0  0
 40 30  1  0  0  0  0
 32 40  1  1  0  0  0
 41 23  1  0  0  0  0
 42 24  2  0  0  0  0
 26 43  1  6  0  0  0
 28 44  1  6  0  0  0
 45 31  1  0  0  0  0
 53 18  1  0  0  0  0
 54 19  1  0  0  0  0
 55 22  1  0  0  0  0
 55 32  1  0  0  0  0
 27 56  1  1  0  0  0
 58 46  1  0  0  0  0
 58 47  1  0  0  0  0
 58 48  2  0  0  0  0
 58 56  1  0  0  0  0
 59 49  1  0  0  0  0
 59 50  2  0  0  0  0
 59 53  1  0  0  0  0
 59 57  1  0  0  0  0
 60 51  1  0  0  0  0
 60 52  2  0  0  0  0
 60 54  1  0  0  0  0
 60 57  1  0  0  0  0
 61 17  1  0  0  0  0
 61 24  1  0  0  0  0
 62 12  1  0  0  0  0
 63 13  1  0  0  0  0
 22 64  1  6  0  0  0
 26 65  1  1  0  0  0
 27 66  1  1  0  0  0
 28 67  1  6  0  0  0
 32 68  1  6  0  0  0
M  CHG  4  41  -1  45  -1  46  -1  47  -1
M  END
> <DATABASE_ID>
MMDBc0029729

> <DATABASE_NAME>
MIME

> <SMILES>
[H]\C(CCCCCCCCC)=C(\[H])C(=O)SCCN=C([O-])CCN=C([O-])[C@]([H])(O)C(C)(C)COP(O)(=O)OP(O)(=O)OC[C@@]1([H])O[C@@]([H])(N2C=NC3=C(N)N=CN=C23)[C@]([H])(O)[C@]1([H])OP([O-])([O-])=O

> <INCHI_IDENTIFIER>
InChI=1S/C33H56N7O17P3S/c1-4-5-6-7-8-9-10-11-12-13-24(42)61-17-16-35-23(41)14-15-36-31(45)28(44)33(2,3)19-54-60(51,52)57-59(49,50)53-18-22-27(56-58(46,47)48)26(43)32(55-22)40-21-39-25-29(34)37-20-38-30(25)40/h12-13,20-22,26-28,32,43-44H,4-11,14-19H2,1-3H3,(H,35,41)(H,36,45)(H,49,50)(H,51,52)(H2,34,37,38)(H2,46,47,48)/p-4/b13-12+/t22-,26-,27-,28+,32-/m1/s1

> <INCHI_KEY>
IRFYVBULXZMEDE-DEEZISNZSA-J

> <FORMULA>
C33H52N7O17P3S

> <MOLECULAR_WEIGHT>
943.789

> <EXACT_MASS>
943.235323499

> <JCHEM_ACCEPTOR_COUNT>
17

> <JCHEM_ATOM_COUNT>
113

> <JCHEM_AVERAGE_POLARIZABILITY>
90.2919764314787

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
-4

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3R)-3-{[2-({2-[(2E)-dodec-2-enoylsulfanyl]ethyl}carbamoyl)ethyl]carbamoyl}-3-hydroxy-2,2-dimethylpropyl ({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methyl phosphono}oxy)phosphonate

> <ALOGPS_LOGP>
2.58

> <JCHEM_LOGP>
-0.9488084581479597

> <ALOGPS_LOGS>
-2.29

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-4

> <JCHEM_PKA>
1.9001207347761855

> <JCHEM_PKA_STRONGEST_ACIDIC>
0.820978781339821

> <JCHEM_PKA_STRONGEST_BASIC>
4.006053268556904

> <JCHEM_POLAR_SURFACE_AREA>
374.94999999999993

> <JCHEM_REFRACTIVITY>
214.8504

> <JCHEM_ROTATABLE_BOND_COUNT>
29

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.25e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3R)-3-{[2-({2-[(2E)-dodec-2-enoylsulfanyl]ethyl}carbamoyl)ethyl]carbamoyl}-3-hydroxy-2,2-dimethylpropyl {[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methyl phosphono}oxyphosphonate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 22-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   22-MAY-19         0                                  
HETATM    1  C   UNK     0      -1.132  39.958   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      28.415  42.268   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      25.335  42.268   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.201  40.728   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.535  39.958   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.869  40.728   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.202  39.958   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.536  40.728   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.870  39.958   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.203  40.728   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.537  39.958   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      10.871  40.728   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      12.204  39.958   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      21.540  40.728   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      22.874  39.958   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      17.539  39.958   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      16.205  40.728   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      30.876  50.738   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      26.875  43.808   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      38.662  54.808   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      33.733  56.100   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      32.210  51.508   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      20.206  39.958   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      13.538  40.728   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      36.171  56.618   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      34.647  52.026   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      33.616  50.881   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      26.875  40.728   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      37.577  57.244   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      36.010  55.086   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      25.541  39.958   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      33.877  53.359   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      26.875  42.268   0.000  0.00  0.00           C+0
HETATM   34  N   UNK     0      37.738  58.776   0.000  0.00  0.00           N+0
HETATM   35  N   UNK     0      18.873  40.728   0.000  0.00  0.00           N+0
HETATM   36  N   UNK     0      24.207  40.728   0.000  0.00  0.00           N+0
HETATM   37  N   UNK     0      38.823  56.339   0.000  0.00  0.00           N+0
HETATM   38  N   UNK     0      37.255  54.181   0.000  0.00  0.00           N+0
HETATM   39  N   UNK     0      34.764  57.244   0.000  0.00  0.00           N+0
HETATM   40  N   UNK     0      34.503  54.766   0.000  0.00  0.00           N+0
HETATM   41  O   UNK     0      20.206  38.418   0.000  0.00  0.00           O-1
HETATM   42  O   UNK     0      13.538  42.268   0.000  0.00  0.00           O+0
HETATM   43  O   UNK     0      36.178  51.865   0.000  0.00  0.00           O+0
HETATM   44  O   UNK     0      28.209  39.958   0.000  0.00  0.00           O+0
HETATM   45  O   UNK     0      25.541  38.418   0.000  0.00  0.00           O-1
HETATM   46  O   UNK     0      31.762  49.489   0.000  0.00  0.00           O-1
HETATM   47  O   UNK     0      33.823  47.200   0.000  0.00  0.00           O-1
HETATM   48  O   UNK     0      31.648  47.314   0.000  0.00  0.00           O+0
HETATM   49  O   UNK     0      30.312  47.094   0.000  0.00  0.00           O+0
HETATM   50  O   UNK     0      28.772  49.761   0.000  0.00  0.00           O+0
HETATM   51  O   UNK     0      29.749  46.118   0.000  0.00  0.00           O+0
HETATM   52  O   UNK     0      26.669  46.118   0.000  0.00  0.00           O+0
HETATM   53  O   UNK     0      30.876  49.198   0.000  0.00  0.00           O+0
HETATM   54  O   UNK     0      28.209  44.578   0.000  0.00  0.00           O+0
HETATM   55  O   UNK     0      32.371  53.039   0.000  0.00  0.00           O+0
HETATM   56  O   UNK     0      33.937  49.375   0.000  0.00  0.00           O+0
HETATM   57  O   UNK     0      28.209  47.658   0.000  0.00  0.00           O+0
HETATM   58  P   UNK     0      32.792  48.344   0.000  0.00  0.00           P+0
HETATM   59  P   UNK     0      29.542  48.428   0.000  0.00  0.00           P+0
HETATM   60  P   UNK     0      28.209  46.118   0.000  0.00  0.00           P+0
HETATM   61  S   UNK     0      14.872  39.958   0.000  0.00  0.00           S+0
HETATM   62  H   UNK     0      10.871  42.268   0.000  0.00  0.00           H+0
HETATM   63  H   UNK     0      12.204  38.418   0.000  0.00  0.00           H+0
HETATM   64  H   UNK     0      32.290  49.970   0.000  0.00  0.00           H+0
HETATM   65  H   UNK     0      35.199  50.588   0.000  0.00  0.00           H+0
HETATM   66  H   UNK     0      33.296  52.388   0.000  0.00  0.00           H+0
HETATM   67  H   UNK     0      25.541  41.498   0.000  0.00  0.00           H+0
HETATM   68  H   UNK     0      35.415  53.440   0.000  0.00  0.00           H+0
CONECT    1    4                                                            
CONECT    2   33                                                            
CONECT    3   33                                                            
CONECT    4    1    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   62                                                  
CONECT   13   12   24   63                                                  
CONECT   14   15   23                                                       
CONECT   15   14   36                                                       
CONECT   16   17   35                                                       
CONECT   17   16   61                                                       
CONECT   18   22   53                                                       
CONECT   19   33   54                                                       
CONECT   20   37   38                                                       
CONECT   21   39   40                                                       
CONECT   22   18   27   55   64                                             
CONECT   23   14   35   41                                                  
CONECT   24   13   42   61                                                  
CONECT   25   29   30   39                                                  
CONECT   26   27   32   43   65                                             
CONECT   27   22   26   56   66                                             
CONECT   28   31   33   44   67                                             
CONECT   29   25   34   37                                                  
CONECT   30   25   38   40                                                  
CONECT   31   28   36   45                                                  
CONECT   32   26   40   55   68                                             
CONECT   33    2    3   19   28                                             
CONECT   34   29                                                            
CONECT   35   16   23                                                       
CONECT   36   15   31                                                       
CONECT   37   20   29                                                       
CONECT   38   20   30                                                       
CONECT   39   21   25                                                       
CONECT   40   21   30   32                                                  
CONECT   41   23                                                            
CONECT   42   24                                                            
CONECT   43   26                                                            
CONECT   44   28                                                            
CONECT   45   31                                                            
CONECT   46   58                                                            
CONECT   47   58                                                            
CONECT   48   58                                                            
CONECT   49   59                                                            
CONECT   50   59                                                            
CONECT   51   60                                                            
CONECT   52   60                                                            
CONECT   53   18   59                                                       
CONECT   54   19   60                                                       
CONECT   55   22   32                                                       
CONECT   56   27   58                                                       
CONECT   57   59   60                                                       
CONECT   58   46   47   48   56                                             
CONECT   59   49   50   53   57                                             
CONECT   60   51   52   54   57                                             
CONECT   61   17   24                                                       
CONECT   62   12                                                            
CONECT   63   13                                                            
CONECT   64   22                                                            
CONECT   65   26                                                            
CONECT   66   27                                                            
CONECT   67   28                                                            
CONECT   68   32                                                            
MASTER        0    0    0    0    0    0    0    0   68    0  140    0
END

Synonyms

Value	Source
(2E)-Dodec-2-enoyl-CoA	HMDB
(2E)-Dodec-2-enoyl-coenzyme A	HMDB
2-trans-Dodecenoyl-CoA	HMDB
2-trans-Dodecenoyl-coenzyme A	HMDB

Molecular Formula

C₃₃H₅₂N₇O₁₇P₃S

Average Mass

943.789

Monoisotopic Mass

943.235323499

IUPAC Name

(3R)-3-{[2-({2-[(2E)-dodec-2-enoylsulfanyl]ethyl}carbamoyl)ethyl]carbamoyl}-3-hydroxy-2,2-dimethylpropyl ({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methyl phosphono}oxy)phosphonate

Traditional Name

(3R)-3-{[2-({2-[(2E)-dodec-2-enoylsulfanyl]ethyl}carbamoyl)ethyl]carbamoyl}-3-hydroxy-2,2-dimethylpropyl {[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methyl phosphono}oxyphosphonate

CAS Registry Number

1066-12-2

SMILES

[H]\C(CCCCCCCCC)=C(\[H])C(=O)SCCN=C([O-])CCN=C([O-])[C@]([H])(O)C(C)(C)COP(O)(=O)OP(O)(=O)OC[C@@]1([H])O[C@@]([H])(N2C=NC3=C(N)N=CN=C23)[C@]([H])(O)[C@]1([H])OP([O-])([O-])=O

InChI Identifier

InChI=1S/C33H56N7O17P3S/c1-4-5-6-7-8-9-10-11-12-13-24(42)61-17-16-35-23(41)14-15-36-31(45)28(44)33(2,3)19-54-60(51,52)57-59(49,50)53-18-22-27(56-58(46,47)48)26(43)32(55-22)40-21-39-25-29(34)37-20-38-30(25)40/h12-13,20-22,26-28,32,43-44H,4-11,14-19H2,1-3H3,(H,35,41)(H,36,45)(H,49,50)(H,51,52)(H2,34,37,38)(H2,46,47,48)/p-4/b13-12+/t22-,26-,27-,28+,32-/m1/s1

InChI Key

IRFYVBULXZMEDE-DEEZISNZSA-J

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as medium-chain 2-enoyl coas. These are organic compounds containing a coenzyme A substructure linked to a medium-chain 2-enoyl chain of 5 to 12 carbon atoms.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acyl thioesters

Direct Parent

Medium-chain 2-enoyl CoAs

Alternative Parents

Substituents

Coenzyme a or derivatives
Purine ribonucleoside 3',5'-bisphosphate
Purine ribonucleoside bisphosphate
Purine ribonucleoside diphosphate
Pentose phosphate
Pentose-5-phosphate
Ribonucleoside 3'-phosphate
Beta amino acid or derivatives
Glycosyl compound
N-glycosyl compound
6-aminopurine
Monosaccharide phosphate
Organic pyrophosphate
Imidazopyrimidine
Purine
Aminopyrimidine
N-substituted imidazole
Alkyl phosphate
Organic phosphoric acid derivative
N-acyl-amine
Monosaccharide
Pyrimidine
Fatty amide
Phosphoric acid ester
Imidolactam
Tetrahydrofuran
Imidazole
Heteroaromatic compound
Azole
Thiocarboxylic acid ester
Carbothioic s-ester
Amino acid or derivatives
Carboxamide group
Secondary carboxylic acid amide
Secondary alcohol
Thiocarboxylic acid or derivatives
Sulfenyl compound
Organoheterocyclic compound
Azacycle
Carboxylic acid derivative
Oxacycle
Alcohol
Organic oxygen compound
Organic nitrogen compound
Hydrocarbon derivative
Organopnictogen compound
Carbonyl group
Primary amine
Organic oxide
Amine
Organosulfur compound
Organooxygen compound
Organonitrogen compound
Organic anion
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

monounsaturated fatty acyl-CoA(4-) (CHEBI:57330 )

Functional Ontology

Not Available

Physical Properties

State

Solid

Predicted Properties

Property	Value	Source
Water Solubility	5.25 g/L	ALOGPS
logP	2.58	ALOGPS
logP	-0.95	ChemAxon
logS	-2.3	ALOGPS
pKa (Strongest Acidic)	0.82	ChemAxon
pKa (Strongest Basic)	4.01	ChemAxon
Physiological Charge	-4	ChemAxon
Hydrogen Acceptor Count	17	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	374.95 Å²	ChemAxon
Rotatable Bond Count	29	ChemAxon
Refractivity	214.85 m³·mol⁻¹	ChemAxon
Polarizability	90.29 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0f6x-0000001009-fcb669581371edf05663	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0zgi-1030200009-d0b7bdc525ed6a35d06c	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9731202000-1ba6d5f82c31a5e5b03c	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-0000000009-5514d635658aff7991b2	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0udi-0701100009-88093dc142db70e06b7e	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-01si-9700110000-a8999ab2a958fcb19bd0	2015-09-15	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-22	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Feces

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Data Source	Reference
MMDBr0000627	(2E)-Dodecenoyl-CoA	3Z-dodecenoyl-CoA	enoyl-CoA delta isomerase 1	VMH	15351645
MMDBr0002637	Lauroyl-CoA	(2E)-Dodecenoyl-CoA	mitochondrial trans-2-enoyl-CoA reductase	VMH	12654921
MMDBr0002653	(S)-3-Hydroxydodecanoyl-CoA	(2E)-Dodecenoyl-CoA	enoyl CoA hydratase, short chain, 1, mitochondrial	VMH	8012501 8188243
MMDBr0002654	(2E)-Dodecenoyl-CoA	(S)-3-Hydroxydodecanoyl-CoA	enoyl CoA hydratase, short chain, 1, mitochondrial	VMH	8012501 8188243
MMDBr0002956	Lauroyl-CoA	(2E)-Dodecenoyl-CoA	acyl-CoA oxidase 1, palmitoyl	VMH	17603022 6240978 7876265
MMDBr0002960	Lauroyl-CoA	(2E)-Dodecenoyl-CoA	acyl-CoA oxidase 1, palmitoyl	VMH	17603022 1774065 3597357 6240978 7876265
MMDBr0005074	L-Carnitine	Dodecenoyl Carnitine	carnitine palmitoyltransferase 1A (liver)	VMH	18678604
MMDBr0005198	(2E)-Dodecenoyl-CoA	Decanoyl-CoA (N-C10:0CoA)	acetyl-CoA acyltransferase 1	VMH	10709653 11296696 11330072 16766224
MMDBr0005199	3Z-dodecenoyl-CoA	(2E)-Dodecenoyl-CoA	enoyl-CoA delta isomerase 2	VMH	1495956 2303409 10419495 3582650
MMDBr0007695	(2E)-Dodecenoyl-CoA	Lauroyl-CoA	Not Available	VMH	30371894
MMDBr0007760	(S)-3-Hydroxydodecanoyl-CoA	(2E)-Dodecenoyl-CoA	Not Available	VMH	30371894
MMDBr0009464	4(R)-Hydroxy-Dodec-6Z-Enoate	(2E)-Dodecenoyl-CoA	Not Available	VMH	30371894
MMDBr0009475	4(S)-Hydroxy-Dodec-6Z-Enoate	(2E)-Dodecenoyl-CoA	Not Available	VMH	30371894
MMDBr0010054	Lauroyl-CoA	(2E)-Dodecenoyl-CoA	acyl-CoA dehydrogenase family, member 9	VMH	30371894
MMDBr0010119	(2E)-Dodecenoyl-CoA	Cis-Laur-5-Enoyl Coenzyme A	enoyl CoA hydratase 1, peroxisomal	VMH; KEGG	30371894
MMDBr0010161	(2E)-Dodecenoyl-CoA	Cis-Laur-5-Enoyl Coenzyme A	enoyl-CoA delta isomerase 1	VMH	30371894

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Proteobacteria	141	Human feces; Human sputum; Human ; Human unknown; Pig ; Human pleural fluid plaque; Human stool; Human feces; pleural fluid plaque; bal	Unknown; Metabolic reconstruction
Bacteria	Firmicutes	106	Pig ; Human feces; Human ; Human urine; Human mucosa	Metabolic reconstruction
Bacteria	Actinobacteria	57	Human feces; Human ; Human subgingival plaque; Human supragingival plaque	Metabolic reconstruction
Archaea	Thaumarchaeota	1		Metabolic reconstruction
Bacteria	Bacteroidetes	11	Human feces; Human	Metabolic reconstruction
Bacteria	Synergistetes	1	Human feces	Metabolic reconstruction
Bacteria	Fusobacteria	2	Human feces; Human	Metabolic reconstruction
Archaea	Euryarchaeota	1		Metabolic reconstruction
Bacteria	Planctomycetes	1	Human feces	Metabolic reconstruction
Archaea	Crenarchaeota	1		Metabolic reconstruction
Eukaryota/Fungi	Ascomycota	1	Human feces; Human saliva	Unknown

Exposure Sources

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected but not Quantified									HMDB

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB023218

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

45266564

PDB ID

Not Available

ChEBI ID

57330

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Noronha A, Modamio J, Jarosz Y, Guerard E, Sompairac N, Preciat G, Danielsdottir AD, Krecke M, Merten D, Haraldsdottir HS, Heinken A, Heirendt L, Magnusdottir S, Ravcheev DA, Sahoo S, Gawron P, Friscioni L, Garcia B, Prendergast M, Puente A, Rodrigues M, Roy A, Rouquaya M, Wiltgen L, Zagare A, John E, Krueger M, Kuperstein I, Zinovyev A, Schneider R, Fleming RMT, Thiele I: The Virtual Metabolic Human database: integrating human and gut microbiome metabolism with nutrition and disease. Nucleic Acids Res. 2019 Jan 8;47(D1):D614-D624. doi: 10.1093/nar/gky992. [PubMed:30371894 ]

Showing metabocard for (2E)-Dodecenoyl-CoA (MMDBc0029729)

MOL for #<Metabolite:0x00007fdb58031cc8>

3D MOL for #<Metabolite:0x00007fdb58031cc8>

3D SDF for #<Metabolite:0x00007fdb58031cc8>

3D-SDF for #<Metabolite:0x00007fdb58031cc8>

PDB for #<Metabolite:0x00007fdb58031cc8>

3D PDB for #<Metabolite:0x00007fdb58031cc8>

SMILES for #<Metabolite:0x00007fdb58031cc8>

INCHI for #<Metabolite:0x00007fdb58031cc8>

Structure for #<Metabolite:0x00007fdb58031cc8>

3D Structure for #<Metabolite:0x00007fdb58031cc8>