MiMeDB: Showing metabocard for 3-keto-5-cis-tetradecenoyl-CoA (MMDBc0031970)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-18 01:57:01 UTC

Update Date

2022-08-31 18:26:57 UTC

Metabolite ID

MMDBc0031970

Metabolite Identification

Common Name

3-keto-5-cis-tetradecenoyl-CoA

Description

In E.coli, 3-keto-5-cis-tetradecenoyl-CoA is a involved in few reactions, fatty acid oxidation complex and anaerobic fatty acid oxidation complex catalyse the reaction 3-hydroxy-5-cis-tetradecenoyl-CoA + NAD+ = 3-keto-5-cis-tetradecenoyl-CoA + NADH + H+ , and beta component fatty acid oxidation complex catalyses the reaction 3-cis-dodecenoyl-CoA + acetyl-CoA = 3-keto-5-cis-tetradecenoyl-CoA + coenzyme A (BioCyc compound: CPD-15244).

Structure

MOL SDF PDB SMILES InChI


  Mrv1572008171511182D          

 71 73  0  0  1  0            999 V2000
   -7.3516   16.2521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1918   18.7271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5418   18.7271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6371   16.6646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9226   16.2521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2081   16.6646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4937   16.2521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7792   16.6646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0647   16.2521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3503   16.6646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6358   16.2521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9213   16.6646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9213   17.4896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5089   17.9021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2234   17.4896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3655   17.4896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6510   17.9021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5076   17.4896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5102   23.2646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3668   19.5521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6815   25.4450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0410   26.1373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2068   17.9021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2247   23.6771    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.7945   17.4896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2221   17.9021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3467   26.4148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5304   23.9547    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.9784   23.3416    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.3668   17.9021    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   14.1003   26.7504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2604   25.5944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6523   17.4896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1179   24.6692    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.3668   18.7271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1866   27.5709    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0800   17.9021    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.9379   17.9021    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.7678   26.2655    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.9279   25.1094    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.5930   26.7504    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.4535   25.4228    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2068   18.7271    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7945   16.6646    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    1.2221   18.7271    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.3509   23.8685    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0813   17.4896    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6523   16.6646    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   10.9848   22.5957    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   12.0888   21.3695    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   10.9237   21.4306    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.2082   21.3127    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.3832   22.7416    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.9063   20.7896    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2563   20.7896    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.5102   22.4396    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0813   19.9646    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.3109   24.4976    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.1499   22.5346    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0813   21.6146    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.5368   21.9826    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    9.7957   22.0271    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    9.0813   20.7896    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    1.9366   17.4896    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6358   15.4271    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2068   16.2521    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.2679   22.8533    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.8261   23.1845    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.8068   24.1486    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6523   18.3146    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.9418   24.7123    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  2  0  0  0  0
 13 12  1  0  0  0  0
 15 14  1  0  0  0  0
 17 16  1  0  0  0  0
 23 13  1  0  0  0  0
 23 18  1  0  0  0  0
 24 19  1  1  0  0  0
 25 14  1  0  0  0  0
 26 18  1  0  0  0  0
 29 24  1  0  0  0  0
 29 28  1  0  0  0  0
 31 27  2  0  0  0  0
 32 27  1  0  0  0  0
 33 30  1  0  0  0  0
 34 28  1  0  0  0  0
 35  2  1  0  0  0  0
 35  3  1  0  0  0  0
 35 20  1  0  0  0  0
 35 30  1  0  0  0  0
 36 31  1  0  0  0  0
 37 16  1  4  0  0  0
 37 25  2  0  0  0  0
 38 15  1  4  0  0  0
 38 33  2  0  0  0  0
 39 21  2  0  0  0  0
 39 31  1  0  0  0  0
 40 21  1  0  0  0  0
 40 32  2  0  0  0  0
 41 22  2  0  0  0  0
 41 27  1  0  0  0  0
 42 22  1  0  0  0  0
 42 32  1  0  0  0  0
 34 42  1  1  0  0  0
 43 23  2  0  0  0  0
 44 25  1  0  0  0  0
 45 26  2  0  0  0  0
 28 46  1  6  0  0  0
 30 47  1  6  0  0  0
 48 33  1  0  0  0  0
 56 19  1  0  0  0  0
 57 20  1  0  0  0  0
 58 24  1  0  0  0  0
 58 34  1  0  0  0  0
 29 59  1  1  0  0  0
 61 49  1  0  0  0  0
 61 50  1  0  0  0  0
 61 51  2  0  0  0  0
 61 59  1  0  0  0  0
 62 52  1  0  0  0  0
 62 53  2  0  0  0  0
 62 56  1  0  0  0  0
 62 60  1  0  0  0  0
 63 54  1  0  0  0  0
 63 55  2  0  0  0  0
 63 57  1  0  0  0  0
 63 60  1  0  0  0  0
 64 17  1  0  0  0  0
 64 26  1  0  0  0  0
 65 11  1  0  0  0  0
 66 12  1  0  0  0  0
 24 67  1  6  0  0  0
 28 68  1  1  0  0  0
 29 69  1  1  0  0  0
 30 70  1  6  0  0  0
 34 71  1  6  0  0  0
M  CHG  4  44  -1  48  -1  49  -1  50  -1
M  END


  Mrv1572008171511182D          

 71 73  0  0  1  0            999 V2000
   -7.3516   16.2521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1918   18.7271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5418   18.7271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6371   16.6646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9226   16.2521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2081   16.6646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4937   16.2521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7792   16.6646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0647   16.2521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3503   16.6646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6358   16.2521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9213   16.6646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9213   17.4896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5089   17.9021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2234   17.4896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3655   17.4896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6510   17.9021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5076   17.4896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5102   23.2646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3668   19.5521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6815   25.4450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0410   26.1373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2068   17.9021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2247   23.6771    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.7945   17.4896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2221   17.9021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3467   26.4148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5304   23.9547    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.9784   23.3416    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.3668   17.9021    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   14.1003   26.7504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2604   25.5944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6523   17.4896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1179   24.6692    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.3668   18.7271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1866   27.5709    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0800   17.9021    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.9379   17.9021    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.7678   26.2655    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.9279   25.1094    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.5930   26.7504    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.4535   25.4228    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2068   18.7271    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7945   16.6646    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    1.2221   18.7271    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.3509   23.8685    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0813   17.4896    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6523   16.6646    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   10.9848   22.5957    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   12.0888   21.3695    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   10.9237   21.4306    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.2082   21.3127    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.3832   22.7416    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.9063   20.7896    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2563   20.7896    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.5102   22.4396    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0813   19.9646    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.3109   24.4976    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.1499   22.5346    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0813   21.6146    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.5368   21.9826    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    9.7957   22.0271    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    9.0813   20.7896    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    1.9366   17.4896    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6358   15.4271    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2068   16.2521    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.2679   22.8533    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.8261   23.1845    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.8068   24.1486    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6523   18.3146    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.9418   24.7123    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  2  0  0  0  0
 13 12  1  0  0  0  0
 15 14  1  0  0  0  0
 17 16  1  0  0  0  0
 23 13  1  0  0  0  0
 23 18  1  0  0  0  0
 24 19  1  1  0  0  0
 25 14  1  0  0  0  0
 26 18  1  0  0  0  0
 29 24  1  0  0  0  0
 29 28  1  0  0  0  0
 31 27  2  0  0  0  0
 32 27  1  0  0  0  0
 33 30  1  0  0  0  0
 34 28  1  0  0  0  0
 35  2  1  0  0  0  0
 35  3  1  0  0  0  0
 35 20  1  0  0  0  0
 35 30  1  0  0  0  0
 36 31  1  0  0  0  0
 37 16  1  4  0  0  0
 37 25  2  0  0  0  0
 38 15  1  4  0  0  0
 38 33  2  0  0  0  0
 39 21  2  0  0  0  0
 39 31  1  0  0  0  0
 40 21  1  0  0  0  0
 40 32  2  0  0  0  0
 41 22  2  0  0  0  0
 41 27  1  0  0  0  0
 42 22  1  0  0  0  0
 42 32  1  0  0  0  0
 34 42  1  1  0  0  0
 43 23  2  0  0  0  0
 44 25  1  0  0  0  0
 45 26  2  0  0  0  0
 28 46  1  6  0  0  0
 30 47  1  6  0  0  0
 48 33  1  0  0  0  0
 56 19  1  0  0  0  0
 57 20  1  0  0  0  0
 58 24  1  0  0  0  0
 58 34  1  0  0  0  0
 29 59  1  1  0  0  0
 61 49  1  0  0  0  0
 61 50  1  0  0  0  0
 61 51  2  0  0  0  0
 61 59  1  0  0  0  0
 62 52  1  0  0  0  0
 62 53  2  0  0  0  0
 62 56  1  0  0  0  0
 62 60  1  0  0  0  0
 63 54  1  0  0  0  0
 63 55  2  0  0  0  0
 63 57  1  0  0  0  0
 63 60  1  0  0  0  0
 64 17  1  0  0  0  0
 64 26  1  0  0  0  0
 65 11  1  0  0  0  0
 66 12  1  0  0  0  0
 24 67  1  6  0  0  0
 28 68  1  1  0  0  0
 29 69  1  1  0  0  0
 30 70  1  6  0  0  0
 34 71  1  6  0  0  0
M  CHG  4  44  -1  48  -1  49  -1  50  -1
M  END
> <DATABASE_ID>
MMDBc0031970

> <DATABASE_NAME>
MIME

> <SMILES>
[H]\C(CCCCCCCC)=C(/[H])CC(=O)CC(=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/C35H58N7O18P3S/c1-4-5-6-7-8-9-10-11-12-13-23(43)18-26(45)64-17-16-37-25(44)14-15-38-33(48)30(47)35(2,3)20-57-63(54,55)60-62(52,53)56-19-24-29(59-61(49,50)51)28(46)34(58-24)42-22-41-27-31(36)39-21-40-32(27)42/h11-12,21-22,24,28-30,34,46-47H,4-10,13-20H2,1-3H3,(H,37,44)(H,38,48)(H,52,53)(H,54,55)(H2,36,39,40)(H2,49,50,51)/p-4/b12-11-/t24-,28-,29-,30+,34-/m1/s1

> <INCHI_KEY>
KADPWMJVUVWQNK-STFCKWFXSA-J

> <FORMULA>
C35H54N7O18P3S

> <MOLECULAR_WEIGHT>
985.83

> <EXACT_MASS>
985.248084414

> <JCHEM_ACCEPTOR_COUNT>
20

> <JCHEM_ATOM_COUNT>
118

> <JCHEM_AVERAGE_POLARIZABILITY>
92.96537540356037

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
-4

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R)-4-({[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonatooxy)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)-2-hydroxy-3,3-dimethyl-N-{2-[(2-{[(5Z)-3-oxotetradec-5-enoyl]sulfanyl}ethyl)carboximidato]ethyl}butanecarboximidate

> <ALOGPS_LOGP>
2.57

> <JCHEM_LOGP>
0.27550036227682934

> <ALOGPS_LOGS>
-2.26

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-4

> <JCHEM_PKA>
1.895035121094251

> <JCHEM_PKA_STRONGEST_ACIDIC>
0.8199607539548772

> <JCHEM_PKA_STRONGEST_BASIC>
4.888671628610082

> <JCHEM_POLAR_SURFACE_AREA>
399.00000000000006

> <JCHEM_REFRACTIVITY>
249.15630000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
31

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.78e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R)-4-[({[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-3-(phosphonatooxy)oxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy]-2-hydroxy-3,3-dimethyl-N-{2-[(2-{[(5Z)-3-oxotetradec-5-enoyl]sulfanyl}ethyl)carboximidato]ethyl}butanecarboximidate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 17-AUG-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-AUG-15         0                                  
HETATM    1  C   UNK     0     -13.723  30.337   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      17.158  34.957   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      14.078  34.957   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0     -12.389  31.107   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0     -11.056  30.337   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -9.722  31.107   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -8.388  30.337   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -7.055  31.107   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -5.721  30.337   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -4.387  31.107   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -3.053  30.337   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.720  31.107   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.720  32.647   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.283  33.417   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      11.617  32.647   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.282  32.647   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.949  33.417   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.948  32.647   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      19.619  43.427   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      15.618  36.497   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      27.406  47.497   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      22.476  48.790   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -0.386  33.417   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      20.953  44.197   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       8.950  32.647   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       2.281  33.417   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      24.914  49.308   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      23.390  44.715   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      22.360  43.571   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      15.618  33.417   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      26.321  49.934   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      24.753  47.776   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      14.284  32.647   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      22.620  46.049   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      15.618  34.957   0.000  0.00  0.00           C+0
HETATM   36  N   UNK     0      26.482  51.466   0.000  0.00  0.00           N+0
HETATM   37  N   UNK     0       7.616  33.417   0.000  0.00  0.00           N+0
HETATM   38  N   UNK     0      12.951  33.417   0.000  0.00  0.00           N+0
HETATM   39  N   UNK     0      27.567  49.029   0.000  0.00  0.00           N+0
HETATM   40  N   UNK     0      25.999  46.871   0.000  0.00  0.00           N+0
HETATM   41  N   UNK     0      23.507  49.934   0.000  0.00  0.00           N+0
HETATM   42  N   UNK     0      23.246  47.456   0.000  0.00  0.00           N+0
HETATM   43  O   UNK     0      -0.386  34.957   0.000  0.00  0.00           O+0
HETATM   44  O   UNK     0       8.950  31.107   0.000  0.00  0.00           O-1
HETATM   45  O   UNK     0       2.281  34.957   0.000  0.00  0.00           O+0
HETATM   46  O   UNK     0      24.922  44.554   0.000  0.00  0.00           O+0
HETATM   47  O   UNK     0      16.952  32.647   0.000  0.00  0.00           O+0
HETATM   48  O   UNK     0      14.284  31.107   0.000  0.00  0.00           O-1
HETATM   49  O   UNK     0      20.505  42.179   0.000  0.00  0.00           O-1
HETATM   50  O   UNK     0      22.566  39.890   0.000  0.00  0.00           O-1
HETATM   51  O   UNK     0      20.391  40.004   0.000  0.00  0.00           O+0
HETATM   52  O   UNK     0      19.055  39.784   0.000  0.00  0.00           O+0
HETATM   53  O   UNK     0      17.515  42.451   0.000  0.00  0.00           O+0
HETATM   54  O   UNK     0      18.492  38.807   0.000  0.00  0.00           O+0
HETATM   55  O   UNK     0      15.412  38.807   0.000  0.00  0.00           O+0
HETATM   56  O   UNK     0      19.619  41.887   0.000  0.00  0.00           O+0
HETATM   57  O   UNK     0      16.952  37.267   0.000  0.00  0.00           O+0
HETATM   58  O   UNK     0      21.114  45.729   0.000  0.00  0.00           O+0
HETATM   59  O   UNK     0      22.680  42.065   0.000  0.00  0.00           O+0
HETATM   60  O   UNK     0      16.952  40.347   0.000  0.00  0.00           O+0
HETATM   61  P   UNK     0      21.535  41.034   0.000  0.00  0.00           P+0
HETATM   62  P   UNK     0      18.285  41.117   0.000  0.00  0.00           P+0
HETATM   63  P   UNK     0      16.952  38.807   0.000  0.00  0.00           P+0
HETATM   64  S   UNK     0       3.615  32.647   0.000  0.00  0.00           S+0
HETATM   65  H   UNK     0      -3.053  28.797   0.000  0.00  0.00           H+0
HETATM   66  H   UNK     0      -0.386  30.337   0.000  0.00  0.00           H+0
HETATM   67  H   UNK     0      21.033  42.659   0.000  0.00  0.00           H+0
HETATM   68  H   UNK     0      23.942  43.278   0.000  0.00  0.00           H+0
HETATM   69  H   UNK     0      22.039  45.077   0.000  0.00  0.00           H+0
HETATM   70  H   UNK     0      14.284  34.187   0.000  0.00  0.00           H+0
HETATM   71  H   UNK     0      24.158  46.130   0.000  0.00  0.00           H+0
CONECT    1    4                                                            
CONECT    2   35                                                            
CONECT    3   35                                                            
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   65                                                  
CONECT   12   11   13   66                                                  
CONECT   13   12   23                                                       
CONECT   14   15   25                                                       
CONECT   15   14   38                                                       
CONECT   16   17   37                                                       
CONECT   17   16   64                                                       
CONECT   18   23   26                                                       
CONECT   19   24   56                                                       
CONECT   20   35   57                                                       
CONECT   21   39   40                                                       
CONECT   22   41   42                                                       
CONECT   23   13   18   43                                                  
CONECT   24   19   29   58   67                                             
CONECT   25   14   37   44                                                  
CONECT   26   18   45   64                                                  
CONECT   27   31   32   41                                                  
CONECT   28   29   34   46   68                                             
CONECT   29   24   28   59   69                                             
CONECT   30   33   35   47   70                                             
CONECT   31   27   36   39                                                  
CONECT   32   27   40   42                                                  
CONECT   33   30   38   48                                                  
CONECT   34   28   42   58   71                                             
CONECT   35    2    3   20   30                                             
CONECT   36   31                                                            
CONECT   37   16   25                                                       
CONECT   38   15   33                                                       
CONECT   39   21   31                                                       
CONECT   40   21   32                                                       
CONECT   41   22   27                                                       
CONECT   42   22   32   34                                                  
CONECT   43   23                                                            
CONECT   44   25                                                            
CONECT   45   26                                                            
CONECT   46   28                                                            
CONECT   47   30                                                            
CONECT   48   33                                                            
CONECT   49   61                                                            
CONECT   50   61                                                            
CONECT   51   61                                                            
CONECT   52   62                                                            
CONECT   53   62                                                            
CONECT   54   63                                                            
CONECT   55   63                                                            
CONECT   56   19   62                                                       
CONECT   57   20   63                                                       
CONECT   58   24   34                                                       
CONECT   59   29   61                                                       
CONECT   60   62   63                                                       
CONECT   61   49   50   51   59                                             
CONECT   62   52   53   56   60                                             
CONECT   63   54   55   57   60                                             
CONECT   64   17   26                                                       
CONECT   65   11                                                            
CONECT   66   12                                                            
CONECT   67   24                                                            
CONECT   68   28                                                            
CONECT   69   29                                                            
CONECT   70   30                                                            
CONECT   71   34                                                            
MASTER        0    0    0    0    0    0    0    0   71    0  146    0
END

Synonyms

Value	Source
(5Z)-3-Ketotetradecenoyl-CoA(4-)	ChEBI
(5Z)-3-Ketotetradecenoyl-coenzyme A(4-)	ChEBI
(5Z)-3-Oxotetradecenoyl-coenzyme A(4-)	ChEBI
3-oxo-(5Z-Tetradecenoyl)-CoA	ChEBI

Molecular Formula

C₃₅H₅₄N₇O₁₈P₃S

Average Mass

985.83

Monoisotopic Mass

985.248084414

IUPAC Name

(2R)-4-({[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonatooxy)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)-2-hydroxy-3,3-dimethyl-N-{2-[(2-{[(5Z)-3-oxotetradec-5-enoyl]sulfanyl}ethyl)carboximidato]ethyl}butanecarboximidate

Traditional Name

(2R)-4-[({[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-3-(phosphonatooxy)oxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy]-2-hydroxy-3,3-dimethyl-N-{2-[(2-{[(5Z)-3-oxotetradec-5-enoyl]sulfanyl}ethyl)carboximidato]ethyl}butanecarboximidate

CAS Registry Number

Not Available

SMILES

[H]\C(CCCCCCCC)=C(/[H])CC(=O)CC(=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/C35H58N7O18P3S/c1-4-5-6-7-8-9-10-11-12-13-23(43)18-26(45)64-17-16-37-25(44)14-15-38-33(48)30(47)35(2,3)20-57-63(54,55)60-62(52,53)56-19-24-29(59-61(49,50)51)28(46)34(58-24)42-22-41-27-31(36)39-21-40-32(27)42/h11-12,21-22,24,28-30,34,46-47H,4-10,13-20H2,1-3H3,(H,37,44)(H,38,48)(H,52,53)(H,54,55)(H2,36,39,40)(H2,49,50,51)/p-4/b12-11-/t24-,28-,29-,30+,34-/m1/s1

InChI Key

KADPWMJVUVWQNK-STFCKWFXSA-J

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as long-chain 3-oxoacyl coas. These are organic compounds containing a coenzyme A derivative, which is 3-oxo acylated long aliphatic chain of 13 to 21 carbon atoms.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acyl thioesters

Direct Parent

Long-chain 3-oxoacyl 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
Alkyl phosphate
N-acyl-amine
1,3-dicarbonyl compound
N-substituted imidazole
Organic phosphoric acid derivative
Pyrimidine
Monosaccharide
Imidolactam
Phosphoric acid ester
Fatty amide
Tetrahydrofuran
Heteroaromatic compound
Azole
Imidazole
Carboxamide group
Ketone
Carbothioic s-ester
Amino acid or derivatives
Secondary alcohol
Secondary carboxylic acid amide
Thiocarboxylic acid ester
Sulfenyl compound
Thiocarboxylic acid or derivatives
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

organic molecular entity (CHEBI:87707 )
3-oxo-fatty acyl-CoA(4-) (CHEBI:87707 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	5.78 g/L	ALOGPS
logP	2.57	ALOGPS
logP	0.28	ChemAxon
logS	-2.3	ALOGPS
pKa (Strongest Acidic)	0.82	ChemAxon
pKa (Strongest Basic)	4.89	ChemAxon
Physiological Charge	-4	ChemAxon
Hydrogen Acceptor Count	20	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	399 Å²	ChemAxon
Rotatable Bond Count	31	ChemAxon
Refractivity	249.16 m³·mol⁻¹	ChemAxon
Polarizability	92.97 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	splash10-000j-0000000109-65d6b6d4e5a58d567e8f	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-004j-0000100009-875ae4ea8201db7c7dc2	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9500601201-9eb21b4f86420d110261	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-0000000009-0ebd11119c6d412d85bd	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001l-0200000019-b4e2732d3a7ca212f640	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-01rt-9400000000-3fca86e05dd982ba609c	2015-09-15	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-20	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

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	Reaction Type	Data Source	Reference

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	1	Human ; Human feces; Human feces; pleural fluid plaque; bal; Human stool	Unknown

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference

External Links

HMDB ID

Not Available

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

90659295

PDB ID

Not Available

ChEBI ID

87707

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Sajed T, Marcu A, Ramirez M, Pon A, Guo AC, Knox C, Wilson M, Grant JR, Djoumbou Y, Wishart DS: ECMDB 2.0: A richer resource for understanding the biochemistry of E. coli. Nucleic Acids Res. 2016 Jan 4;44(D1):D495-501. doi: 10.1093/nar/gkv1060. Epub 2015 Oct 19. [PubMed:26481353 ]

Showing metabocard for 3-keto-5-cis-tetradecenoyl-CoA (MMDBc0031970)

MOL for #<Metabolite:0x00005634c2aa1520>

3D MOL for #<Metabolite:0x00005634c2aa1520>

3D SDF for #<Metabolite:0x00005634c2aa1520>

3D-SDF for #<Metabolite:0x00005634c2aa1520>

PDB for #<Metabolite:0x00005634c2aa1520>

3D PDB for #<Metabolite:0x00005634c2aa1520>

SMILES for #<Metabolite:0x00005634c2aa1520>

INCHI for #<Metabolite:0x00005634c2aa1520>

Structure for #<Metabolite:0x00005634c2aa1520>

3D Structure for #<Metabolite:0x00005634c2aa1520>