MiMeDB: Showing metabocard for (3R)-3-hydroxy-stearoyl-CoA (MMDBc0047854)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-19 15:46:05 UTC

Update Date

2022-09-01 02:00:09 UTC

Metabolite ID

MMDBc0047854

Metabolite Identification

Common Name

(3R)-3-hydroxy-stearoyl-CoA

Description

(3R)-3-hydroxy-stearoyl-CoA belongs to the class of organic compounds known as long-chain fatty acyl coas. These are acyl CoAs where the group acylated to the coenzyme A moiety is a long aliphatic chain of 13 to 21 carbon atoms (3R)-3-hydroxy-stearoyl-CoA is a strong basic compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv1572012221504432D          

 68 70  0  0  0  0            999 V2000
  -15.2128   -0.5327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -14.4983   -0.1202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -13.7838   -0.5327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -13.0693   -0.1202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.3549   -0.5327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.6404   -0.1202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.9259   -0.5327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.2115   -0.1202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.4970   -0.5327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7825   -0.1202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0681   -0.5327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3536   -0.1202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6391   -0.5327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9246   -0.1202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2102   -0.5327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4957   -0.1202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4957    0.7047    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7812   -0.5327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0668   -0.1202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0668    0.7047    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3523   -0.5327    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6378   -0.1202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9233   -0.5327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2089   -0.1202    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5055   -0.5327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5055   -1.3577    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2200   -0.1202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9344   -0.5327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6489   -0.1202    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3634   -0.5327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0779   -0.1202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0779    0.7047    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7923   -0.5327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3798   -1.2472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2048    0.1816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5068   -0.9452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2213   -0.5327    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9357   -0.9452    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    6.5232   -1.6597    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    7.3482   -0.2308    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6502   -1.3577    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3647   -0.9452    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    8.7772   -1.6597    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    7.9522   -0.2308    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0792   -0.5327    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.7936   -0.9452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5081   -0.5327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5943    0.2876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9812    0.8397    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.1528    1.6466    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   10.9597    1.4751    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.3458    1.8182    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   10.3243    2.4536    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   11.4013    0.4592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7369    1.2128    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.8138   -0.2552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2618   -0.8683    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.6343   -0.3414    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.1863    0.2716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9400   -0.0639    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.8538   -0.8844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4058   -1.4975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2128   -1.3259    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.1508   -2.2821    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.3439   -2.4536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7918   -1.8405    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.0468   -1.0559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3634   -1.3577    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  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  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  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
 14 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
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 31 33  1  0  0  0  0
 33 34  1  0  0  0  0
 33 35  1  0  0  0  0
 33 36  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  1  0  0  0  0
 38 39  1  0  0  0  0
 38 40  2  0  0  0  0
 38 41  1  0  0  0  0
 41 42  1  0  0  0  0
 42 43  1  0  0  0  0
 42 44  2  0  0  0  0
 42 45  1  0  0  0  0
 45 46  1  0  0  0  0
 46 47  1  0  0  0  0
 47 48  1  0  0  0  0
 48 49  1  0  0  0  0
 49 50  1  0  0  0  0
 50 51  2  0  0  0  0
 50 52  1  0  0  0  0
 50 53  1  0  0  0  0
 48 54  1  0  0  0  0
 54 55  1  0  0  0  0
 54 56  1  0  0  0  0
 56 57  1  0  0  0  0
 47 57  1  0  0  0  0
 56 58  1  0  0  0  0
 58 59  1  0  0  0  0
 59 60  2  0  0  0  0
 60 61  1  0  0  0  0
 61 62  1  0  0  0  0
 62 63  1  0  0  0  0
 62 64  2  0  0  0  0
 64 65  1  0  0  0  0
 65 66  2  0  0  0  0
 66 67  1  0  0  0  0
 61 67  2  0  0  0  0
 58 67  1  0  0  0  0
 30 68  2  0  0  0  0
M  CHG  4  39  -1  43  -1  52  -1  53  -1
M  END


  Mrv1572012221504432D          

 68 70  0  0  0  0            999 V2000
  -15.2128   -0.5327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -14.4983   -0.1202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -13.7838   -0.5327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -13.0693   -0.1202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.3549   -0.5327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.6404   -0.1202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.9259   -0.5327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.2115   -0.1202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.4970   -0.5327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7825   -0.1202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0681   -0.5327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3536   -0.1202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6391   -0.5327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9246   -0.1202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2102   -0.5327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4957   -0.1202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4957    0.7047    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7812   -0.5327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0668   -0.1202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0668    0.7047    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3523   -0.5327    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6378   -0.1202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9233   -0.5327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2089   -0.1202    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5055   -0.5327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5055   -1.3577    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2200   -0.1202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9344   -0.5327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6489   -0.1202    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3634   -0.5327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0779   -0.1202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0779    0.7047    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7923   -0.5327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3798   -1.2472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2048    0.1816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5068   -0.9452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2213   -0.5327    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9357   -0.9452    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    6.5232   -1.6597    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    7.3482   -0.2308    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6502   -1.3577    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3647   -0.9452    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    8.7772   -1.6597    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    7.9522   -0.2308    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0792   -0.5327    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.7936   -0.9452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5081   -0.5327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5943    0.2876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9812    0.8397    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.1528    1.6466    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   10.9597    1.4751    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.3458    1.8182    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   10.3243    2.4536    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   11.4013    0.4592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7369    1.2128    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.8138   -0.2552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2618   -0.8683    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.6343   -0.3414    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.1863    0.2716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9400   -0.0639    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.8538   -0.8844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4058   -1.4975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2128   -1.3259    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.1508   -2.2821    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.3439   -2.4536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7918   -1.8405    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.0468   -1.0559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3634   -1.3577    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  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  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  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
 14 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
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 31 33  1  0  0  0  0
 33 34  1  0  0  0  0
 33 35  1  0  0  0  0
 33 36  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  1  0  0  0  0
 38 39  1  0  0  0  0
 38 40  2  0  0  0  0
 38 41  1  0  0  0  0
 41 42  1  0  0  0  0
 42 43  1  0  0  0  0
 42 44  2  0  0  0  0
 42 45  1  0  0  0  0
 45 46  1  0  0  0  0
 46 47  1  0  0  0  0
 47 48  1  0  0  0  0
 48 49  1  0  0  0  0
 49 50  1  0  0  0  0
 50 51  2  0  0  0  0
 50 52  1  0  0  0  0
 50 53  1  0  0  0  0
 48 54  1  0  0  0  0
 54 55  1  0  0  0  0
 54 56  1  0  0  0  0
 56 57  1  0  0  0  0
 47 57  1  0  0  0  0
 56 58  1  0  0  0  0
 58 59  1  0  0  0  0
 59 60  2  0  0  0  0
 60 61  1  0  0  0  0
 61 62  1  0  0  0  0
 62 63  1  0  0  0  0
 62 64  2  0  0  0  0
 64 65  1  0  0  0  0
 65 66  2  0  0  0  0
 66 67  1  0  0  0  0
 61 67  2  0  0  0  0
 58 67  1  0  0  0  0
 30 68  2  0  0  0  0
M  CHG  4  39  -1  43  -1  52  -1  53  -1
M  END
> <DATABASE_ID>
MMDBc0047854

> <DATABASE_NAME>
MIME

> <SMILES>
CCCCCCCCCCCCCCCC(O)CC(=O)SCCNC(=O)CCNC(=O)C(O)C(C)(C)COP([O-])(=O)OP([O-])(=O)OCC1OC(C(O)C1OP([O-])([O-])=O)N1C=NC2=C1N=CN=C2N

> <INCHI_IDENTIFIER>
InChI=1S/C39H70N7O18P3S/c1-4-5-6-7-8-9-10-11-12-13-14-15-16-17-27(47)22-30(49)68-21-20-41-29(48)18-19-42-37(52)34(51)39(2,3)24-61-67(58,59)64-66(56,57)60-23-28-33(63-65(53,54)55)32(50)38(62-28)46-26-45-31-35(40)43-25-44-36(31)46/h25-28,32-34,38,47,50-51H,4-24H2,1-3H3,(H,41,48)(H,42,52)(H,56,57)(H,58,59)(H2,40,43,44)(H2,53,54,55)/p-4

> <INCHI_KEY>
WZMAIEGYXCOYSH-UHFFFAOYSA-J

> <FORMULA>
C39H66N7O18P3S

> <MOLECULAR_WEIGHT>
1045.97

> <EXACT_MASS>
1045.341984801

> <JCHEM_ACCEPTOR_COUNT>
18

> <JCHEM_ATOM_COUNT>
134

> <JCHEM_AVERAGE_POLARIZABILITY>
105.15179172544487

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
-4

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-hydroxy-3-{[2-({2-[(3-hydroxyoctadecanoyl)sulfanyl]ethyl}carbamoyl)ethyl]carbamoyl}-2,2-dimethylpropyl ({[5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonatooxy)oxolan-2-yl]methyl phosphonato}oxy)phosphonate

> <ALOGPS_LOGP>
3.18

> <JCHEM_LOGP>
0.21351033316740942

> <ALOGPS_LOGS>
-2.96

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-4

> <JCHEM_PKA>
1.9035538370263239

> <JCHEM_PKA_STRONGEST_ACIDIC>
0.8207476508908771

> <JCHEM_PKA_STRONGEST_BASIC>
4.945907435196925

> <JCHEM_POLAR_SURFACE_AREA>
395.17999999999995

> <JCHEM_REFRACTIVITY>
242.87860000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
36

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.24e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-hydroxy-3-{[2-({2-[(3-hydroxyoctadecanoyl)sulfanyl]ethyl}carbamoyl)ethyl]carbamoyl}-2,2-dimethylpropyl {[5-(6-aminopurin-9-yl)-4-hydroxy-3-(phosphonatooxy)oxolan-2-yl]methyl phosphonato}oxyphosphonate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 22-DEC-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   22-DEC-15         0                                  
HETATM    1  C   UNK     0     -28.397  -0.994   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0     -27.063  -0.224   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0     -25.730  -0.994   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0     -24.396  -0.224   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0     -23.062  -0.994   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0     -21.729  -0.224   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0     -20.395  -0.994   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0     -19.061  -0.224   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0     -17.728  -0.994   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0     -16.394  -0.224   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0     -15.060  -0.994   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0     -13.727  -0.224   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0     -12.393  -0.994   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0     -11.059  -0.224   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -9.726  -0.994   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -8.392  -0.224   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -8.392   1.315   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      -7.058  -0.994   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -5.725  -0.224   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -5.725   1.315   0.000  0.00  0.00           O+0
HETATM   21  S   UNK     0      -4.391  -0.994   0.000  0.00  0.00           S+0
HETATM   22  C   UNK     0      -3.057  -0.224   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -1.723  -0.994   0.000  0.00  0.00           C+0
HETATM   24  N   UNK     0      -0.390  -0.224   0.000  0.00  0.00           N+0
HETATM   25  C   UNK     0       0.944  -0.994   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       0.944  -2.534   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       2.277  -0.224   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       3.611  -0.994   0.000  0.00  0.00           C+0
HETATM   29  N   UNK     0       4.945  -0.224   0.000  0.00  0.00           N+0
HETATM   30  C   UNK     0       6.278  -0.994   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       7.612  -0.224   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       7.612   1.315   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       8.946  -0.994   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       8.176  -2.328   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       9.716   0.339   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      10.279  -1.764   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0      11.613  -0.994   0.000  0.00  0.00           O+0
HETATM   38  P   UNK     0      12.947  -1.764   0.000  0.00  0.00           P+0
HETATM   39  O   UNK     0      12.177  -3.098   0.000  0.00  0.00           O-1
HETATM   40  O   UNK     0      13.717  -0.431   0.000  0.00  0.00           O+0
HETATM   41  O   UNK     0      14.280  -2.534   0.000  0.00  0.00           O+0
HETATM   42  P   UNK     0      15.614  -1.764   0.000  0.00  0.00           P+0
HETATM   43  O   UNK     0      16.384  -3.098   0.000  0.00  0.00           O-1
HETATM   44  O   UNK     0      14.844  -0.431   0.000  0.00  0.00           O+0
HETATM   45  O   UNK     0      16.948  -0.994   0.000  0.00  0.00           O+0
HETATM   46  C   UNK     0      18.281  -1.764   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0      19.615  -0.994   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0      19.776   0.537   0.000  0.00  0.00           C+0
HETATM   49  O   UNK     0      18.632   1.567   0.000  0.00  0.00           O+0
HETATM   50  P   UNK     0      18.952   3.074   0.000  0.00  0.00           P+0
HETATM   51  O   UNK     0      20.458   2.754   0.000  0.00  0.00           O+0
HETATM   52  O   UNK     0      17.445   3.394   0.000  0.00  0.00           O-1
HETATM   53  O   UNK     0      19.272   4.580   0.000  0.00  0.00           O-1
HETATM   54  C   UNK     0      21.282   0.857   0.000  0.00  0.00           C+0
HETATM   55  O   UNK     0      21.909   2.264   0.000  0.00  0.00           O+0
HETATM   56  C   UNK     0      22.052  -0.476   0.000  0.00  0.00           C+0
HETATM   57  O   UNK     0      21.022  -1.621   0.000  0.00  0.00           O+0
HETATM   58  N   UNK     0      23.584  -0.637   0.000  0.00  0.00           N+0
HETATM   59  C   UNK     0      24.614   0.507   0.000  0.00  0.00           C+0
HETATM   60  N   UNK     0      26.021  -0.119   0.000  0.00  0.00           N+0
HETATM   61  C   UNK     0      25.860  -1.651   0.000  0.00  0.00           C+0
HETATM   62  C   UNK     0      26.891  -2.795   0.000  0.00  0.00           C+0
HETATM   63  N   UNK     0      28.397  -2.475   0.000  0.00  0.00           N+0
HETATM   64  N   UNK     0      26.415  -4.260   0.000  0.00  0.00           N+0
HETATM   65  C   UNK     0      24.909  -4.580   0.000  0.00  0.00           C+0
HETATM   66  N   UNK     0      23.878  -3.436   0.000  0.00  0.00           N+0
HETATM   67  C   UNK     0      24.354  -1.971   0.000  0.00  0.00           C+0
HETATM   68  O   UNK     0       6.278  -2.534   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    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                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31   68                                                  
CONECT   31   30   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   34   35   36                                             
CONECT   34   33                                                            
CONECT   35   33                                                            
CONECT   36   33   37                                                       
CONECT   37   36   38                                                       
CONECT   38   37   39   40   41                                             
CONECT   39   38                                                            
CONECT   40   38                                                            
CONECT   41   38   42                                                       
CONECT   42   41   43   44   45                                             
CONECT   43   42                                                            
CONECT   44   42                                                            
CONECT   45   42   46                                                       
CONECT   46   45   47                                                       
CONECT   47   46   48   57                                                  
CONECT   48   47   49   54                                                  
CONECT   49   48   50                                                       
CONECT   50   49   51   52   53                                             
CONECT   51   50                                                            
CONECT   52   50                                                            
CONECT   53   50                                                            
CONECT   54   48   55   56                                                  
CONECT   55   54                                                            
CONECT   56   54   57   58                                                  
CONECT   57   56   47                                                       
CONECT   58   56   59   67                                                  
CONECT   59   58   60                                                       
CONECT   60   59   61                                                       
CONECT   61   60   62   67                                                  
CONECT   62   61   63   64                                                  
CONECT   63   62                                                            
CONECT   64   62   65                                                       
CONECT   65   64   66                                                       
CONECT   66   65   67                                                       
CONECT   67   66   61   58                                                  
CONECT   68   30                                                            
MASTER        0    0    0    0    0    0    0    0   68    0  140    0
END

Synonyms

Not Available

Molecular Formula

C₃₉H₆₆N₇O₁₈P₃S

Average Mass

1045.97

Monoisotopic Mass

1045.341984801

IUPAC Name

3-hydroxy-3-{[2-({2-[(3-hydroxyoctadecanoyl)sulfanyl]ethyl}carbamoyl)ethyl]carbamoyl}-2,2-dimethylpropyl ({[5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonatooxy)oxolan-2-yl]methyl phosphonato}oxy)phosphonate

Traditional Name

3-hydroxy-3-{[2-({2-[(3-hydroxyoctadecanoyl)sulfanyl]ethyl}carbamoyl)ethyl]carbamoyl}-2,2-dimethylpropyl {[5-(6-aminopurin-9-yl)-4-hydroxy-3-(phosphonatooxy)oxolan-2-yl]methyl phosphonato}oxyphosphonate

CAS Registry Number

Not Available

SMILES

CCCCCCCCCCCCCCCC(O)CC(=O)SCCNC(=O)CCNC(=O)C(O)C(C)(C)COP([O-])(=O)OP([O-])(=O)OCC1OC(C(O)C1OP([O-])([O-])=O)N1C=NC2=C1N=CN=C2N

InChI Identifier

InChI=1S/C39H70N7O18P3S/c1-4-5-6-7-8-9-10-11-12-13-14-15-16-17-27(47)22-30(49)68-21-20-41-29(48)18-19-42-37(52)34(51)39(2,3)24-61-67(58,59)64-66(56,57)60-23-28-33(63-65(53,54)55)32(50)38(62-28)46-26-45-31-35(40)43-25-44-36(31)46/h25-28,32-34,38,47,50-51H,4-24H2,1-3H3,(H,41,48)(H,42,52)(H,56,57)(H,58,59)(H2,40,43,44)(H2,53,54,55)/p-4

InChI Key

WZMAIEGYXCOYSH-UHFFFAOYSA-J

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as long-chain fatty acyl coas. These are acyl CoAs where the group acylated to the coenzyme A moiety is a 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 fatty acyl CoAs

Alternative Parents

Substituents

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

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

a 3<i>S</i>-3-hydroxyacyl-CoA (CPD0-2253 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	1.24 g/L	ALOGPS
logP	3.18	ALOGPS
logP	0.21	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	0.82	ChemAxon
pKa (Strongest Basic)	4.95	ChemAxon
Physiological Charge	-4	ChemAxon
Hydrogen Acceptor Count	18	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	395.18 Å²	ChemAxon
Rotatable Bond Count	36	ChemAxon
Refractivity	242.88 m³·mol⁻¹	ChemAxon
Polarizability	105.15 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	splash10-0f6t-9001000200-499c883af35406bfa70d	2016-09-14	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0f89-9011010000-b1c7eb8b2fabed4c070a	2016-09-14	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-052f-9724500300-37c7d4087ec81f7e223c	2016-09-14	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0f6x-9041000000-e953969c4adbd6f1c0cc	2016-09-14	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0udl-7090000000-ee6f6cb61c79fb0770ee	2016-09-14	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-01rt-9410000000-1da152e6f430825119c4	2016-09-14	View Spectrum

Biological Properties

Cellular Locations

Not Available

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
MMDBr0005091	(3R)-3-hydroxy-stearoyl-CoA	3-Hydroxyoctadecanoyl Carnitine	carnitine palmitoyltransferase 1A (liver)	VMH	7977144
MMDBr0005268	Stearoyl-CoA	(3R)-3-hydroxy-stearoyl-CoA	Not Available	VMH	11751554
MMDBr0005330	(3R)-3-hydroxy-stearoyl-CoA	(3R)-3-hydroxy-stearoyl-CoA	diazepam binding inhibitor (GABA receptor modulator, acyl-CoA binding protein)	VMH	20511713 11859412 16908521 8001684

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
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

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

74413891

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Emken EA: Metabolism of dietary stearic acid relative to other fatty acids in human subjects. Am J Clin Nutr. 1994 Dec;60(6 Suppl):1023S-1028S. doi: 10.1093/ajcn/60.6.1023S. [PubMed:7977144 ]
Jones PM, Tjoa S, Fennessey PV, Goodman SI, Bennett MJ: Addition of quantitative 3-hydroxy-octadecanoic acid to the stable isotope gas chromatography-mass spectrometry method for measuring 3-hydroxy fatty acids. Clin Chem. 2002 Jan;48(1):176-9. [PubMed:11751554 ]
Wishart DS, Li C, Marcu A, Badran H, Pon A, Budinski Z, Patron J, Lipton D, Cao X, Oler E, Li K, Paccoud M, Hong C, Guo AC, Chan C, Wei W, Ramirez-Gaona M: PathBank: a comprehensive pathway database for model organisms. Nucleic Acids Res. 2020 Jan 8;48(D1):D470-D478. doi: 10.1093/nar/gkz861. [PubMed:31602464 ]

Showing metabocard for (3R)-3-hydroxy-stearoyl-CoA (MMDBc0047854)

MOL for #<Metabolite:0x00007fdb59889cd0>

3D MOL for #<Metabolite:0x00007fdb59889cd0>

3D SDF for #<Metabolite:0x00007fdb59889cd0>

3D-SDF for #<Metabolite:0x00007fdb59889cd0>

PDB for #<Metabolite:0x00007fdb59889cd0>

3D PDB for #<Metabolite:0x00007fdb59889cd0>

SMILES for #<Metabolite:0x00007fdb59889cd0>

INCHI for #<Metabolite:0x00007fdb59889cd0>

Structure for #<Metabolite:0x00007fdb59889cd0>

3D Structure for #<Metabolite:0x00007fdb59889cd0>