NP-MRD: Showing NP-Card for (S)-3-Hydroxyhexadecanoyl-CoA (NP0087093)

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Record Information

Version

2.0

Created at

2022-05-11 16:39:52 UTC

Updated at

2022-05-11 16:39:52 UTC

NP-MRD ID

NP0087093

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(S)-3-Hydroxyhexadecanoyl-CoA

Description

(S)-3-Hydroxyhexadecanoyl-CoA, also known as b-hydroxypalmitoyl-coenzyme A or S-(3-hydroxyhexadecanoate, 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 (S)-3-Hydroxyhexadecanoyl-CoA is a strong basic compound (based on its pKa) (S)-3-Hydroxyhexadecanoyl-CoA exists in all living organisms, ranging from bacteria to humans. Succinate-driven synthesis of ATP from ADP and phosphate is progressively inhibited by increasing concentrations of (S)-3-Hydroxyhexadecanoyl-CoA (S)-3-Hydroxyhexadecanoyl-CoA is a beta-oxidation intermediate derivative of palmitoyl-CoA and the substrate of the enzyme peroxisomal acyl-CoA thioesterase 2 (PTE-2, 2), which is localized in the peroxisome.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 02231219492D          

 66 68  0  0  1  0            999 V2000
   24.3225   -7.5761    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   11.0453   -7.2448    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   13.6197   -8.2675    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   15.0410   -8.1207    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   11.5285   -9.7233    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.4922   -7.8569    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.4347   -9.3071    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.9513   -8.7513    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.5984   -6.6326    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.4331   -6.6916    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.2879   -7.7838    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.6574   -7.7979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.1034   -8.9359    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.7942   -8.4575    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.1359   -7.5993    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.0535   -9.4681    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.3779   -7.3675    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.7041   -8.8738    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.5818   -8.5867    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.5521   -7.3431    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.1605   -8.7336    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.3949   -7.0492    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.4872  -10.7611    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.4872  -12.0889    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.9920  -10.5999    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.2775  -11.8375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.9920  -13.0750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.3901   -8.5006    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.2328   -8.2067    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.7457   -8.6419    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.2597   -9.3085    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.5299   -8.8983    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.7434   -9.9769    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   12.1982   -8.4145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7065  -11.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9686  -11.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7065  -11.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9920  -12.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2155   -8.3106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9686   -8.6475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4624   -7.9738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2775  -11.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5524   -7.5575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8786   -9.0638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.0081   -6.9884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.7612   -7.3253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.3398   -7.4722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.4295   -6.8415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.5867   -7.1354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.1826   -7.1784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.9184   -7.6192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.8509   -6.6947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.1653   -7.2822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6369   -8.1638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.6040   -7.0315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.4970   -7.7660    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   34.2722   -6.5477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.7439   -7.4292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.0254   -6.8846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0583   -8.0168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8114   -8.3537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.6937   -6.4008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.0756   -7.9130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4797   -7.8699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.6542   -8.0599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9011   -7.7230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 63  1  0  0  0  0
  1 65  1  0  0  0  0
  2  6  1  0  0  0  0
  2  9  1  0  0  0  0
  2 10  1  0  0  0  0
  2 12  2  0  0  0  0
  3  8  1  0  0  0  0
  3 11  1  0  0  0  0
  3 13  1  0  0  0  0
  3 15  2  0  0  0  0
  4 11  1  0  0  0  0
  4 14  1  0  0  0  0
  4 17  1  0  0  0  0
  4 18  2  0  0  0  0
  5 32  1  0  0  0  0
  5 33  1  0  0  0  0
 30  6  1  6  0  0  0
 31  7  1  6  0  0  0
  8 34  1  0  0  0  0
 14 41  1  0  0  0  0
 16 40  1  0  0  0  0
 56 19  1  6  0  0  0
 20 54  2  0  0  0  0
 21 63  2  0  0  0  0
 22 64  2  0  0  0  0
 33 23  1  1  0  0  0
 23 35  1  0  0  0  0
 23 36  1  0  0  0  0
 24 36  2  0  0  0  0
 24 37  1  0  0  0  0
 25 35  2  0  0  0  0
 25 42  1  0  0  0  0
 26 38  1  0  0  0  0
 26 42  2  0  0  0  0
 27 38  1  0  0  0  0
 28 54  1  0  0  0  0
 28 60  1  0  0  0  0
 29 64  1  0  0  0  0
 29 66  1  0  0  0  0
 30 31  1  0  0  0  0
 30 32  1  0  0  0  0
 31 33  1  0  0  0  0
 32 34  1  1  0  0  0
 35 37  1  0  0  0  0
 37 38  2  0  0  0  0
 39 40  1  0  0  0  0
 39 41  1  0  0  0  0
 39 43  1  0  0  0  0
 39 44  1  0  0  0  0
 40 54  1  0  0  0  0
 45 46  1  0  0  0  0
 45 47  1  0  0  0  0
 46 48  1  0  0  0  0
 47 49  1  0  0  0  0
 48 50  1  0  0  0  0
 49 51  1  0  0  0  0
 50 52  1  0  0  0  0
 51 53  1  0  0  0  0
 52 55  1  0  0  0  0
 53 56  1  0  0  0  0
 55 57  1  0  0  0  0
 56 58  1  0  0  0  0
 57 59  1  0  0  0  0
 58 63  1  0  0  0  0
 59 62  1  0  0  0  0
 60 61  1  0  0  0  0
 61 64  1  0  0  0  0
 65 66  1  0  0  0  0
M  END

     RDKit          3D

132134  0  0  0  0  0  0  0  0999 V2000
   15.7004    1.4540    0.3686 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6050    1.9834   -0.5208 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3254    2.2776    0.2716 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8545    1.0084    0.9197 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6269    1.1183    1.7163 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3668    1.6128    1.1672 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7162    0.8901    0.0271 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3872    0.8818   -1.2728 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9071    0.1152   -2.4132 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5898    0.2998   -2.9975 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4339   -0.0792   -2.1472 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1768    0.1198   -3.0059 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9421   -0.2205   -2.3027 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4059    0.5370   -1.1843 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.1041    1.9008   -1.6756 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0869    0.7412    0.0952 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4782   -0.4132    0.8870 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7676   -0.2966    2.0939 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5781   -2.0567    0.2013 S   0  0  0  0  0  0  0  0  0  0  0  0
    6.1733   -3.2117    1.4371 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1773   -3.4523    2.5175 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0035   -4.1092    2.0473 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0633   -3.6189    1.1448 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0282   -2.5124    0.5776 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9286   -4.5862    0.8133 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0356   -3.9351   -0.1754 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4197   -2.7014    0.3285 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4566   -1.9410   -0.4656 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6515   -2.4094   -1.6557 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1571   -0.6985   -0.0996 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7226   -0.1567   -1.2841 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2667   -1.0048    0.8761 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7135   -1.5778    2.1462 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1307   -2.0681    0.1629 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1554    0.1627    1.1465 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1704   -0.1117    2.0393 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1652    1.2349    2.3044 P   0  0  1  0  0  5  0  0  0  0  0  0
   -6.3518    0.8454    3.1746 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2502    2.4631    3.0003 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7070    1.7786    0.7997 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6014    0.5716    0.0590 P   0  0  2  0  0  5  0  0  0  0  0  0
   -6.3431   -0.7313    0.8040 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0451    0.2945   -1.5323 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2544    0.8254    0.0880 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6278    2.1295    0.2920 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.1230    2.3249    0.2965 C   0  0  1  0  0  0  0  0  0  0  0  0
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  -11.9639    1.6169   -0.7255 C   0  0  1  0  0  0  0  0  0  0  0  0
  -12.5122    0.8435   -1.8143 N   0  0  0  0  0  0  0  0  0  0  0  0
  -11.9495   -0.0835   -2.6003 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.8442   -0.5543   -3.5036 N   0  0  0  0  0  0  0  0  0  0  0  0
  -14.0033    0.0685   -3.3094 C   0  0  0  0  0  0  0  0  0  0  0  0
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  -15.3218   -0.9715   -5.0251 N   0  0  0  0  0  0  0  0  0  0  0  0
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  -16.0535    1.5610   -2.5323 C   0  0  0  0  0  0  0  0  0  0  0  0
  -14.8735    1.6802   -1.8962 N   0  0  0  0  0  0  0  0  0  0  0  0
  -13.8000    0.9370   -2.2611 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.0429    0.9438    0.6115 C   0  0  2  0  0  0  0  0  0  0  0  0
  -13.2446    1.2431    1.2707 O   0  0  0  0  0  0  0  0  0  0  0  0
  -10.8426    1.5212    1.3343 C   0  0  2  0  0  0  0  0  0  0  0  0
  -11.3419    2.4018    2.2902 O   0  0  0  0  0  0  0  0  0  0  0  0
  -10.9868    1.9589    3.8628 P   0  0  1  0  0  5  0  0  0  0  0  0
  -10.0730    3.0330    4.4434 O   0  0  0  0  0  0  0  0  0  0  0  0
  -12.3791    1.9250    4.8111 O   0  0  0  0  0  0  0  0  0  0  0  0
  -10.1357    0.4996    3.9578 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.6779    1.8048   -0.0171 H   0  0  0  0  0  0  0  0  0  0  0  0
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   15.5044    1.7808    1.4086 H   0  0  0  0  0  0  0  0  0  0  0  0
   14.3066    1.1799   -1.2480 H   0  0  0  0  0  0  0  0  0  0  0  0
   14.8863    2.8621   -1.1108 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.6060    2.7123   -0.4421 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.5396    3.0562    1.0205 H   0  0  0  0  0  0  0  0  0  0  0  0
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   10.3761    1.9885   -1.6199 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.5016    0.6612   -1.1979 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.1052   -1.0066   -2.1919 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.6803    0.2817   -3.2512 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3939    1.3645   -3.3346 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4723   -0.2993   -3.9591 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3117    0.3942   -1.2185 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4798   -1.2083   -1.9154 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3177   -0.6070   -3.8525 H   0  0  0  0  0  0  0  0  0  0  0  0
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    5.0107   -1.3127   -2.0005 H   0  0  0  0  0  0  0  0  0  0  0  0
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 56127  1  0
M  END


  Mrv0541 02231219492D          

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M  END
> <DATABASE_ID>
NP0087093

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCCCCCCCCCC[C@H](O)CC(=O)SCCNC(=O)CCNC(=O)C(O)C(C)(C)COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1OP(O)(O)=O)N1C=NC2=C(N)N=CN=C12

> <INCHI_IDENTIFIER>
InChI=1S/C37H66N7O18P3S/c1-4-5-6-7-8-9-10-11-12-13-14-15-25(45)20-28(47)66-19-18-39-27(46)16-17-40-35(50)32(49)37(2,3)22-59-65(56,57)62-64(54,55)58-21-26-31(61-63(51,52)53)30(48)36(60-26)44-24-43-29-33(38)41-23-42-34(29)44/h23-26,30-32,36,45,48-49H,4-22H2,1-3H3,(H,39,46)(H,40,50)(H,54,55)(H,56,57)(H2,38,41,42)(H2,51,52,53)/t25-,26+,30+,31+,32?,36+/m0/s1

> <INCHI_KEY>
DEHLMTDDPWDRDR-QQOJFMBSSA-N

> <FORMULA>
C37H66N7O18P3S

> <MOLECULAR_WEIGHT>
1021.942

> <EXACT_MASS>
1021.339788569

> <JCHEM_ACCEPTOR_COUNT>
18

> <JCHEM_AVERAGE_POLARIZABILITY>
100.09138830997983

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
10

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-2-({[hydroxy({hydroxy[3-hydroxy-3-({2-[(2-{[(3S)-3-hydroxyhexadecanoyl]sulfanyl}ethyl)carbamoyl]ethyl}carbamoyl)-2,2-dimethylpropoxy]phosphoryl}oxy)phosphoryl]oxy}methyl)oxolan-3-yl]oxy}phosphonic acid

> <ALOGPS_LOGP>
1.68

> <JCHEM_LOGP>
-1.7260934449663548

> <ALOGPS_LOGS>
-2.68

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-4

> <JCHEM_PKA>
1.8334045176178515

> <JCHEM_PKA_STRONGEST_ACIDIC>
0.8252479627216065

> <JCHEM_PKA_STRONGEST_BASIC>
4.946047024039826

> <JCHEM_POLAR_SURFACE_AREA>
383.85999999999984

> <JCHEM_REFRACTIVITY>
238.16340000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
34

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.14e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-2-[({hydroxy[hydroxy(3-hydroxy-3-({2-[(2-{[(3S)-3-hydroxyhexadecanoyl]sulfanyl}ethyl)carbamoyl]ethyl}carbamoyl)-2,2-dimethylpropoxy)phosphoryl]oxyphosphoryl}oxy)methyl]oxolan-3-yl]oxyphosphonic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  S   UNK     0      45.402 -14.142   0.000  0.00  0.00           S+0
HETATM    2  P   UNK     0      20.618 -13.524   0.000  0.00  0.00           P+0
HETATM    3  P   UNK     0      25.423 -15.433   0.000  0.00  0.00           P+0
HETATM    4  P   UNK     0      28.077 -15.159   0.000  0.00  0.00           P+0
HETATM    5  O   UNK     0      21.520 -18.150   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0      19.585 -14.666   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0      17.611 -17.373   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0      24.176 -16.336   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0      21.650 -12.381   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0      19.475 -12.491   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0      26.671 -14.530   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      21.760 -14.556   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      26.326 -16.680   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0      29.483 -15.787   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0      24.520 -14.185   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0      33.700 -17.674   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      28.705 -13.753   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      27.448 -16.564   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      49.619 -16.029   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      34.631 -13.707   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      46.966 -16.303   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      39.937 -13.159   0.000  0.00  0.00           O+0
HETATM   23  N   UNK     0      19.576 -20.087   0.000  0.00  0.00           N+0
HETATM   24  N   UNK     0      19.576 -22.566   0.000  0.00  0.00           N+0
HETATM   25  N   UNK     0      16.785 -19.786   0.000  0.00  0.00           N+0
HETATM   26  N   UNK     0      15.451 -22.097   0.000  0.00  0.00           N+0
HETATM   27  N   UNK     0      16.785 -24.407   0.000  0.00  0.00           N+0
HETATM   28  N   UNK     0      36.195 -15.868   0.000  0.00  0.00           N+0
HETATM   29  N   UNK     0      41.501 -15.319   0.000  0.00  0.00           N+0
HETATM   30  C   UNK     0      20.059 -16.132   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      19.151 -17.376   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      21.522 -16.610   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      20.054 -18.624   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      22.770 -15.707   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      18.119 -20.557   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      20.475 -21.327   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      18.119 -22.097   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      16.785 -22.867   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      32.136 -15.513   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      33.541 -16.142   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      30.730 -14.884   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      15.451 -20.557   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0      32.764 -14.107   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0      31.507 -16.919   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0      56.015 -13.045   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0      57.421 -13.674   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0      54.768 -13.948   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0      58.668 -12.771   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0      53.362 -13.319   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0      60.074 -13.400   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0      52.114 -14.223   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0      61.322 -12.497   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0      50.709 -13.593   0.000  0.00  0.00           C+0
HETATM   54  C   UNK     0      34.789 -15.239   0.000  0.00  0.00           C+0
HETATM   55  C   UNK     0      62.727 -13.125   0.000  0.00  0.00           C+0
HETATM   56  C   UNK     0      49.461 -14.497   0.000  0.00  0.00           C+0
HETATM   57  C   UNK     0      63.975 -12.222   0.000  0.00  0.00           C+0
HETATM   58  C   UNK     0      48.055 -13.868   0.000  0.00  0.00           C+0
HETATM   59  C   UNK     0      65.381 -12.851   0.000  0.00  0.00           C+0
HETATM   60  C   UNK     0      37.442 -14.965   0.000  0.00  0.00           C+0
HETATM   61  C   UNK     0      38.848 -15.594   0.000  0.00  0.00           C+0
HETATM   62  C   UNK     0      66.628 -11.948   0.000  0.00  0.00           C+0
HETATM   63  C   UNK     0      46.808 -14.771   0.000  0.00  0.00           C+0
HETATM   64  C   UNK     0      40.095 -14.690   0.000  0.00  0.00           C+0
HETATM   65  C   UNK     0      44.155 -15.045   0.000  0.00  0.00           C+0
HETATM   66  C   UNK     0      42.749 -14.416   0.000  0.00  0.00           C+0
CONECT    1   63   65                                                       
CONECT    2    6    9   10   12                                             
CONECT    3    8   11   13   15                                             
CONECT    4   11   14   17   18                                             
CONECT    5   32   33                                                       
CONECT    6    2   30                                                       
CONECT    7   31                                                            
CONECT    8    3   34                                                       
CONECT    9    2                                                            
CONECT   10    2                                                            
CONECT   11    3    4                                                       
CONECT   12    2                                                            
CONECT   13    3                                                            
CONECT   14    4   41                                                       
CONECT   15    3                                                            
CONECT   16   40                                                            
CONECT   17    4                                                            
CONECT   18    4                                                            
CONECT   19   56                                                            
CONECT   20   54                                                            
CONECT   21   63                                                            
CONECT   22   64                                                            
CONECT   23   33   35   36                                                  
CONECT   24   36   37                                                       
CONECT   25   35   42                                                       
CONECT   26   38   42                                                       
CONECT   27   38                                                            
CONECT   28   54   60                                                       
CONECT   29   64   66                                                       
CONECT   30    6   31   32                                                  
CONECT   31    7   30   33                                                  
CONECT   32    5   30   34                                                  
CONECT   33    5   23   31                                                  
CONECT   34    8   32                                                       
CONECT   35   23   25   37                                                  
CONECT   36   23   24                                                       
CONECT   37   24   35   38                                                  
CONECT   38   26   27   37                                                  
CONECT   39   40   41   43   44                                             
CONECT   40   16   39   54                                                  
CONECT   41   14   39                                                       
CONECT   42   25   26                                                       
CONECT   43   39                                                            
CONECT   44   39                                                            
CONECT   45   46   47                                                       
CONECT   46   45   48                                                       
CONECT   47   45   49                                                       
CONECT   48   46   50                                                       
CONECT   49   47   51                                                       
CONECT   50   48   52                                                       
CONECT   51   49   53                                                       
CONECT   52   50   55                                                       
CONECT   53   51   56                                                       
CONECT   54   20   28   40                                                  
CONECT   55   52   57                                                       
CONECT   56   19   53   58                                                  
CONECT   57   55   59                                                       
CONECT   58   56   63                                                       
CONECT   59   57   62                                                       
CONECT   60   28   61                                                       
CONECT   61   60   64                                                       
CONECT   62   59                                                            
CONECT   63    1   21   58                                                  
CONECT   64   22   29   61                                                  
CONECT   65    1   66                                                       
CONECT   66   29   65                                                       
MASTER        0    0    0    0    0    0    0    0   66    0  136    0
END

View in JSmol

Synonyms

Value	Source
(S)-3-Hydroxyhexadecanoyl-coenzyme A	HMDB
(S)-3-Hydroxypalmitoyl-coenzyme A	HMDB
b-Hydroxypalmitoyl-CoA	HMDB
b-Hydroxypalmitoyl-coenzyme A	HMDB
beta-Hydroxypalmitoyl-CoA	HMDB
beta-Hydroxypalmitoyl-coenzyme A	HMDB
DL-3-Hydroxyhexadecanoyl-S-coenzyme A	HMDB
DL-3-Hydroxyhexadecanoyl-scoa	HMDB
DL-3-Hydroxyhexadecanoyl-Scoenzyme A	HMDB
S-(3-Hydroxyhexadecanoate	HMDB
S-(3-Hydroxyhexadecanoate)coenzyme A	HMDB
S-(3-Hydroxyhexadecanoic acid	HMDB
S-DL-3-Hydroxyhexadecanoate	HMDB
S-DL-3-Hydroxyhexadecanoic acid	HMDB
3-Hydroxyhexadecanoyl-CoA	HMDB
3-Hydroxyhexadecanoyl-coenzyme A	HMDB

Chemical Formula

C₃₇H₆₆N₇O₁₈P₃S

Average Mass

1021.9420 Da

Monoisotopic Mass

1021.33979 Da

IUPAC Name

{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-2-({[hydroxy({hydroxy[3-hydroxy-3-({2-[(2-{[(3S)-3-hydroxyhexadecanoyl]sulfanyl}ethyl)carbamoyl]ethyl}carbamoyl)-2,2-dimethylpropoxy]phosphoryl}oxy)phosphoryl]oxy}methyl)oxolan-3-yl]oxy}phosphonic acid

Traditional Name

[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-2-[({hydroxy[hydroxy(3-hydroxy-3-({2-[(2-{[(3S)-3-hydroxyhexadecanoyl]sulfanyl}ethyl)carbamoyl]ethyl}carbamoyl)-2,2-dimethylpropoxy)phosphoryl]oxyphosphoryl}oxy)methyl]oxolan-3-yl]oxyphosphonic acid

CAS Registry Number

Not Available

SMILES

CCCCCCCCCCCCC[C@H](O)CC(=O)SCCNC(=O)CCNC(=O)C(O)C(C)(C)COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1OP(O)(O)=O)N1C=NC2=C(N)N=CN=C12

InChI Identifier

InChI=1S/C37H66N7O18P3S/c1-4-5-6-7-8-9-10-11-12-13-14-15-25(45)20-28(47)66-19-18-39-27(46)16-17-40-35(50)32(49)37(2,3)22-59-65(56,57)62-64(54,55)58-21-26-31(61-63(51,52)53)30(48)36(60-26)44-24-43-29-33(38)41-23-42-34(29)44/h23-26,30-32,36,45,48-49H,4-22H2,1-3H3,(H,39,46)(H,40,50)(H,54,55)(H,56,57)(H2,38,41,42)(H2,51,52,53)/t25-,26+,30+,31+,32?,36+/m0/s1

InChI Key

DEHLMTDDPWDRDR-QQOJFMBSSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Anas platyrhynchos	FooDB	FooDB
Anatidae	FooDB	FooDB
Anser anser	FooDB	FooDB
Bison bison	FooDB	FooDB
Bos taurus	FooDB	FooDB
Bos taurus X Bison bison	FooDB	FooDB
Bubalus bubalis	FooDB	FooDB
Capra aegagrus hircus	FooDB	FooDB
Cervidae	FooDB	FooDB
Cervus canadensis	FooDB	FooDB
Columba	FooDB	FooDB
Columbidae	FooDB	FooDB
Dromaius novaehollandiae	FooDB	FooDB
Equus caballus	FooDB	FooDB
Gallus gallus	FooDB	FooDB
Lagopus muta	FooDB	FooDB
Leporidae	FooDB	FooDB
Lepus timidus	FooDB	FooDB
Melanitta fusca	FooDB	FooDB
Meleagris gallopavo	FooDB	FooDB
Numida meleagris	FooDB	FooDB
Odocoileus	FooDB	FooDB
Oryctolagus	FooDB	FooDB
Ovis aries	FooDB	FooDB
Phasianidae	FooDB	FooDB
Phasianus colchicus	FooDB	FooDB
Struthio camelus	FooDB	FooDB
Sus scrofa	FooDB	FooDB
Sus scrofa domestica	FooDB	FooDB

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

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	1.68	ALOGPS
logP	-1.7	ChemAxon
logS	-2.7	ALOGPS
pKa (Strongest Acidic)	0.83	ChemAxon
pKa (Strongest Basic)	4.95	ChemAxon
Physiological Charge	-4	ChemAxon
Hydrogen Acceptor Count	18	ChemAxon
Hydrogen Donor Count	10	ChemAxon
Polar Surface Area	383.86 Å²	ChemAxon
Rotatable Bond Count	34	ChemAxon
Refractivity	238.16 m³·mol⁻¹	ChemAxon
Polarizability	100.09 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

External Links

HMDB ID

HMDB0003932

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB023251

KNApSAcK ID

Not Available

Chemspider ID

389498

KEGG Compound ID

C05258

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

440600

PDB ID

Not Available

ChEBI ID

27402

Good Scents ID

Not Available

References

General References

Showing NP-Card for (S)-3-Hydroxyhexadecanoyl-CoA (NP0087093)

MOL for NP0087093 ((S)-3-Hydroxyhexadecanoyl-CoA)

3D MOL for NP0087093 ((S)-3-Hydroxyhexadecanoyl-CoA)

3D SDF for NP0087093 ((S)-3-Hydroxyhexadecanoyl-CoA)

3D-SDF for NP0087093 ((S)-3-Hydroxyhexadecanoyl-CoA)

PDB for NP0087093 ((S)-3-Hydroxyhexadecanoyl-CoA)

3D PDB for NP0087093 ((S)-3-Hydroxyhexadecanoyl-CoA)

SMILES for NP0087093 ((S)-3-Hydroxyhexadecanoyl-CoA)

INCHI for NP0087093 ((S)-3-Hydroxyhexadecanoyl-CoA)

Structure for NP0087093 ((S)-3-Hydroxyhexadecanoyl-CoA)

3D Structure for NP0087093 ((S)-3-Hydroxyhexadecanoyl-CoA)