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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (4) Show 4 proteins XML

enzymes (4) Show 4 proteins

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2022-03-07 02:49:08 UTC

HMDB ID

HMDB0001166

Secondary Accession Numbers

HMDB0002383
HMDB01166
HMDB02383

Metabolite Identification

Common Name

3-Hydroxybutyryl-CoA

Description

(R)-3-hydroxybutanoyl-CoA belongs to the class of organic compounds known as (r)-3-hydroxyacyl coas. These are organic compounds containing a (R)-3-hydroxyl acylated coenzyme A derivative. Thus, (R)-3-hydroxybutanoyl-CoA is considered to be a fatty ester lipid molecule (R)-3-hydroxybutanoyl-CoA is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI


  Mrv1652306252022302D          

 54 56  0  0  1  0            999 V2000
   24.5695   -1.8111    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   23.9021   -1.3263    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.3146   -2.5958    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   23.2346   -1.8111    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   23.4896   -2.5958    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   24.7994   -3.2633    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.8237   -5.8522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5666   -6.2647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1093   -6.2647    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.3949   -5.8522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6804   -6.2647    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.1377   -4.6147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3949   -5.0272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1377   -3.7897    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.7088   -3.7897    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.4232   -3.3771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8522   -2.5520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7252   -1.4252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1377   -2.1396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5502   -1.4252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4232   -2.5520    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   15.7087   -2.1396    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.5666   -2.1396    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.2166   -2.1396    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.8665   -2.1396    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.3916   -1.3146    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.3916   -2.9646    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.0415   -1.3146    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.0415   -2.9646    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.3916   -2.1396    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   21.0415   -2.1396    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   22.4500   -1.5563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0046   -3.2633    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.1796   -4.0883    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.8296   -4.0883    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.0046   -4.0883    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   23.0046   -4.9132    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.3541   -1.5563    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   25.9673   -2.1083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.6896   -0.8026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.6817   -1.6958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.9673   -2.9333    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   26.5102   -0.8888    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   27.3962   -2.1082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.6818   -3.3457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.3962   -2.9331    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   28.1106   -1.6957    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.2811   -5.8522    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   19.9956   -7.0897    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.9956   -6.2647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7101   -5.8522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1390   -5.8522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4244   -6.2647    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   21.4244   -7.0897    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1 38  1  1  0  0  0
  2  1  1  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  5  3  1  0  0  0  0
  3  6  1  6  0  0  0
  4 32  1  1  0  0  0
  5  4  1  0  0  0  0
  5 33  1  6  0  0  0
  9  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8 48  1  0  0  0  0
 10  9  1  0  0  0  0
 13 10  1  0  0  0  0
 10 11  2  0  0  0  0
 12 14  1  0  0  0  0
 13 12  1  0  0  0  0
 16 14  1  0  0  0  0
 16 15  2  0  0  0  0
 16 21  1  0  0  0  0
 19 17  1  0  0  0  0
 17 23  1  0  0  0  0
 19 18  1  0  0  0  0
 21 19  1  0  0  0  0
 19 20  1  0  0  0  0
 21 22  1  6  0  0  0
 23 30  1  0  0  0  0
 30 24  1  0  0  0  0
 24 31  1  0  0  0  0
 31 25  1  0  0  0  0
 32 25  1  0  0  0  0
 30 26  2  0  0  0  0
 30 27  1  0  0  0  0
 31 28  2  0  0  0  0
 31 29  1  0  0  0  0
 33 36  1  0  0  0  0
 36 34  1  0  0  0  0
 36 35  1  0  0  0  0
 36 37  2  0  0  0  0
 39 38  1  0  0  0  0
 40 38  1  0  0  0  0
 41 39  2  0  0  0  0
 42 39  1  0  0  0  0
 43 40  2  0  0  0  0
 44 41  1  0  0  0  0
 43 41  1  0  0  0  0
 45 42  2  0  0  0  0
 46 44  2  0  0  0  0
 47 44  1  0  0  0  0
 46 45  1  0  0  0  0
 48 50  1  0  0  0  0
 50 49  2  0  0  0  0
 50 51  1  0  0  0  0
 51 53  1  0  0  0  0
 53 52  1  0  0  0  0
 53 54  1  1  0  0  0
M  END

HMDB0001166
     RDKit          3D
3-Hydroxybutyryl-CoA
 96 98  0  0  0  0  0  0  0  0999 V2000
   10.5876   -3.4468    1.6828 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4387   -2.0371    1.0030 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.5753   -2.3368   -0.0684 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.8108   -1.1462    2.0156 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6138    0.2575    1.7044 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0180    0.8651    2.6921 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.9928    1.2429    0.3502 S   0  0  0  0  0  0  0  0  0  0  0  0
   10.1896    0.5547   -1.2360 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8514    0.1976   -1.9104 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1250    1.4605   -2.0550 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.8168    1.4102   -2.6736 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4052    0.3000   -3.0362 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0873    2.6436   -2.8250 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6358    2.6365   -3.0113 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7733    2.2471   -1.9665 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5409    1.1043   -1.2298 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1775    0.0436   -1.4093 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5015    1.0275   -0.1407 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6813   -0.1936    0.5573 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1018    1.0767   -0.6519 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7108    2.3040   -1.4016 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9124   -0.1716   -1.5174 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1361    0.9143    0.5030 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2827    1.9184    1.4566 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8324    1.6458    2.7037 P   0  0  0  0  0  5  0  0  0  0  0  0
   -0.2523    2.2767    3.9607 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3090    2.4065    2.3874 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0874    0.0027    2.8706 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7344   -0.3205    3.0399 P   0  0  0  0  0  5  0  0  0  0  0  0
   -2.8514   -1.8242    3.2974 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3462    0.4261    4.4433 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6438    0.1462    1.7180 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4402   -0.8859    1.2214 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2085   -0.3735    0.0455 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.0267   -1.3893   -0.4951 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8832   -0.7388   -1.3743 C   0  0  1  0  0  0  0  0  0  0  0  0
   -8.1750   -1.3929   -1.4962 N   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1364   -0.9076   -2.2960 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.2152   -1.7026   -2.2171 N   0  0  0  0  0  0  0  0  0  0  0  0
   -9.9290   -2.6803   -1.3716 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.6895   -3.7623   -0.9359 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.0184   -3.9962   -1.3821 N   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0952   -4.5871   -0.0591 N   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8287   -4.3835    0.3802 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0819   -3.3411   -0.0329 N   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6434   -2.4873   -0.9157 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1204    0.6466   -0.8362 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.5502    1.5548   -1.7300 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2741    0.6235    0.4458 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.7970    1.8715    0.7565 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3721    2.2610    2.3135 P   0  0  0  0  0  5  0  0  0  0  0  0
   -5.2717    2.5635    3.2744 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4382    3.5885    2.1400 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3096    0.9889    2.9474 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.6674   -4.1900    0.8917 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.5215   -3.3832    2.2657 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.6832   -3.5665    2.3014 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.3954   -1.6978    0.6368 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6405   -2.4604    0.2698 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.4094   -1.2642    2.9981 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8113   -1.6152    2.3678 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.8193   -0.3740   -1.2975 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.7142    1.2388   -1.9741 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3070   -0.4716   -1.2406 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.0724   -0.2674   -2.8792 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5162    2.3626   -1.7343 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5472    3.2058   -3.7091 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2953    3.3653   -1.9543 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3340    3.6926   -3.3606 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3791    1.9598   -3.9194 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1201    3.0882   -1.6412 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6926    1.8398    0.5700 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5658   -0.5638    0.3673 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4223    2.3029   -1.5173 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9145    3.2408   -0.8707 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0637    2.2730   -2.4556 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3759    0.0347   -2.5141 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1695   -0.3980   -1.6119 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3938   -1.0515   -1.0722 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9215    0.9455    0.1111 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3476   -0.0860    0.9724 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3669    2.5085    1.3883 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2986    0.2663    4.5403 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1916   -1.1839    2.0112 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8256   -1.7645    1.0047 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5323    0.0413   -0.7292 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4693   -0.7057   -2.4244 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0928   -0.0167   -2.9251 H   0  0  0  0  0  0  0  0  0  0  0  0
  -12.1414   -4.3254   -2.3638 H   0  0  0  0  0  0  0  0  0  0  0  0
  -12.8735   -3.8643   -0.8059 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4619   -5.1251    1.0907 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1738    0.8562   -0.6320 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8033    1.3696   -2.6701 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8754    0.1574    1.2544 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4647    3.9039    1.2078 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9086    0.6206    3.7795 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 20 22  1  0
 20 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  2  0
 25 27  1  0
 25 28  1  0
 28 29  1  0
 29 30  2  0
 29 31  1  0
 29 32  1  0
 32 33  1  0
 33 34  1  0
 34 35  1  0
 35 36  1  0
 36 37  1  0
 37 38  1  0
 38 39  2  0
 39 40  1  0
 40 41  2  0
 41 42  1  0
 41 43  1  0
 43 44  2  0
 44 45  1  0
 45 46  2  0
 36 47  1  0
 47 48  1  0
 47 49  1  0
 49 50  1  0
 50 51  1  0
 51 52  2  0
 51 53  1  0
 51 54  1  0
 49 34  1  0
 46 37  1  0
 46 40  1  0
  1 55  1  0
  1 56  1  0
  1 57  1  0
  2 58  1  6
  3 59  1  0
  4 60  1  0
  4 61  1  0
  8 62  1  0
  8 63  1  0
  9 64  1  0
  9 65  1  0
 10 66  1  0
 13 67  1  0
 13 68  1  0
 14 69  1  0
 14 70  1  0
 15 71  1  0
 18 72  1  1
 19 73  1  0
 21 74  1  0
 21 75  1  0
 21 76  1  0
 22 77  1  0
 22 78  1  0
 22 79  1  0
 23 80  1  0
 23 81  1  0
 27 82  1  0
 31 83  1  0
 33 84  1  0
 33 85  1  0
 34 86  1  6
 36 87  1  6
 38 88  1  0
 42 89  1  0
 42 90  1  0
 44 91  1  0
 47 92  1  1
 48 93  1  0
 49 94  1  1
 53 95  1  0
 54 96  1  0
M  END


  Mrv1652306252022302D          

 54 56  0  0  1  0            999 V2000
   24.5695   -1.8111    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   23.9021   -1.3263    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.3146   -2.5958    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   23.2346   -1.8111    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   23.4896   -2.5958    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   24.7994   -3.2633    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.8237   -5.8522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5666   -6.2647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1093   -6.2647    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.3949   -5.8522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6804   -6.2647    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.1377   -4.6147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3949   -5.0272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1377   -3.7897    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.7088   -3.7897    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.4232   -3.3771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8522   -2.5520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7252   -1.4252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1377   -2.1396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5502   -1.4252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4232   -2.5520    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   15.7087   -2.1396    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.5666   -2.1396    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.2166   -2.1396    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.8665   -2.1396    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.3916   -1.3146    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.3916   -2.9646    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.0415   -1.3146    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.0415   -2.9646    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.3916   -2.1396    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   21.0415   -2.1396    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   22.4500   -1.5563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0046   -3.2633    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.1796   -4.0883    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.8296   -4.0883    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.0046   -4.0883    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   23.0046   -4.9132    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.3541   -1.5563    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   25.9673   -2.1083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.6896   -0.8026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.6817   -1.6958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.9673   -2.9333    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   26.5102   -0.8888    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   27.3962   -2.1082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.6818   -3.3457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.3962   -2.9331    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   28.1106   -1.6957    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.2811   -5.8522    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   19.9956   -7.0897    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.9956   -6.2647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7101   -5.8522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1390   -5.8522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4244   -6.2647    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   21.4244   -7.0897    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1 38  1  1  0  0  0
  2  1  1  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  5  3  1  0  0  0  0
  3  6  1  6  0  0  0
  4 32  1  1  0  0  0
  5  4  1  0  0  0  0
  5 33  1  6  0  0  0
  9  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8 48  1  0  0  0  0
 10  9  1  0  0  0  0
 13 10  1  0  0  0  0
 10 11  2  0  0  0  0
 12 14  1  0  0  0  0
 13 12  1  0  0  0  0
 16 14  1  0  0  0  0
 16 15  2  0  0  0  0
 16 21  1  0  0  0  0
 19 17  1  0  0  0  0
 17 23  1  0  0  0  0
 19 18  1  0  0  0  0
 21 19  1  0  0  0  0
 19 20  1  0  0  0  0
 21 22  1  6  0  0  0
 23 30  1  0  0  0  0
 30 24  1  0  0  0  0
 24 31  1  0  0  0  0
 31 25  1  0  0  0  0
 32 25  1  0  0  0  0
 30 26  2  0  0  0  0
 30 27  1  0  0  0  0
 31 28  2  0  0  0  0
 31 29  1  0  0  0  0
 33 36  1  0  0  0  0
 36 34  1  0  0  0  0
 36 35  1  0  0  0  0
 36 37  2  0  0  0  0
 39 38  1  0  0  0  0
 40 38  1  0  0  0  0
 41 39  2  0  0  0  0
 42 39  1  0  0  0  0
 43 40  2  0  0  0  0
 44 41  1  0  0  0  0
 43 41  1  0  0  0  0
 45 42  2  0  0  0  0
 46 44  2  0  0  0  0
 47 44  1  0  0  0  0
 46 45  1  0  0  0  0
 48 50  1  0  0  0  0
 50 49  2  0  0  0  0
 50 51  1  0  0  0  0
 51 53  1  0  0  0  0
 53 52  1  0  0  0  0
 53 54  1  1  0  0  0
M  END
> <DATABASE_ID>
HMDB0001166

> <DATABASE_NAME>
hmdb

> <SMILES>
C[C@@H](O)CC(=O)SCCNC(=O)CCNC(=O)[C@H](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=C1N=CN=C2N

> <INCHI_IDENTIFIER>
InChI=1S/C25H42N7O18P3S/c1-13(33)8-16(35)54-7-6-27-15(34)4-5-28-23(38)20(37)25(2,3)10-47-53(44,45)50-52(42,43)46-9-14-19(49-51(39,40)41)18(36)24(48-14)32-12-31-17-21(26)29-11-30-22(17)32/h11-14,18-20,24,33,36-37H,4-10H2,1-3H3,(H,27,34)(H,28,38)(H,42,43)(H,44,45)(H2,26,29,30)(H2,39,40,41)/t13-,14-,18-,19-,20+,24-/m1/s1

> <INCHI_KEY>
QHHKKMYHDBRONY-WZZMXTMRSA-N

> <FORMULA>
C25H42N7O18P3S

> <MOLECULAR_WEIGHT>
853.62

> <EXACT_MASS>
853.151989708

> <JCHEM_ACCEPTOR_COUNT>
18

> <JCHEM_ATOM_COUNT>
96

> <JCHEM_AVERAGE_POLARIZABILITY>
77.22945135181149

> <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[(3R)-3-hydroxy-3-({2-[(2-{[(3R)-3-hydroxybutanoyl]sulfanyl}ethyl)carbamoyl]ethyl}carbamoyl)-2,2-dimethylpropoxy]phosphoryl}oxy)phosphoryl]oxy}methyl)oxolan-3-yl]oxy}phosphonic acid

> <ALOGPS_LOGP>
-0.62

> <JCHEM_LOGP>
-6.04527939814796

> <ALOGPS_LOGS>
-2.32

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-4

> <JCHEM_PKA>
1.9001207347761846

> <JCHEM_PKA_STRONGEST_ACIDIC>
0.8209787813398228

> <JCHEM_PKA_STRONGEST_BASIC>
4.006053268556904

> <JCHEM_POLAR_SURFACE_AREA>
383.8599999999999

> <JCHEM_REFRACTIVITY>
183.0284

> <JCHEM_ROTATABLE_BOND_COUNT>
22

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.07e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(R)-3-hydroxybutanoyl-coa

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0001166
     RDKit          3D
3-Hydroxybutyryl-CoA
 96 98  0  0  0  0  0  0  0  0999 V2000
   10.5876   -3.4468    1.6828 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4387   -2.0371    1.0030 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.5753   -2.3368   -0.0684 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.8108   -1.1462    2.0156 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6138    0.2575    1.7044 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0180    0.8651    2.6921 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.9928    1.2429    0.3502 S   0  0  0  0  0  0  0  0  0  0  0  0
   10.1896    0.5547   -1.2360 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8514    0.1976   -1.9104 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1250    1.4605   -2.0550 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.8168    1.4102   -2.6736 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4052    0.3000   -3.0362 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0873    2.6436   -2.8250 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6358    2.6365   -3.0113 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7733    2.2471   -1.9665 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5409    1.1043   -1.2298 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1775    0.0436   -1.4093 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5015    1.0275   -0.1407 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6813   -0.1936    0.5573 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1018    1.0767   -0.6519 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7108    2.3040   -1.4016 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9124   -0.1716   -1.5174 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1361    0.9143    0.5030 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2827    1.9184    1.4566 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8324    1.6458    2.7037 P   0  0  0  0  0  5  0  0  0  0  0  0
   -0.2523    2.2767    3.9607 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3090    2.4065    2.3874 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0874    0.0027    2.8706 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7344   -0.3205    3.0399 P   0  0  0  0  0  5  0  0  0  0  0  0
   -2.8514   -1.8242    3.2974 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3462    0.4261    4.4433 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6438    0.1462    1.7180 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4402   -0.8859    1.2214 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2085   -0.3735    0.0455 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.0267   -1.3893   -0.4951 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8832   -0.7388   -1.3743 C   0  0  1  0  0  0  0  0  0  0  0  0
   -8.1750   -1.3929   -1.4962 N   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1364   -0.9076   -2.2960 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.2152   -1.7026   -2.2171 N   0  0  0  0  0  0  0  0  0  0  0  0
   -9.9290   -2.6803   -1.3716 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.6895   -3.7623   -0.9359 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.0184   -3.9962   -1.3821 N   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0952   -4.5871   -0.0591 N   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8287   -4.3835    0.3802 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0819   -3.3411   -0.0329 N   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6434   -2.4873   -0.9157 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1204    0.6466   -0.8362 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.5502    1.5548   -1.7300 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2741    0.6235    0.4458 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.7970    1.8715    0.7565 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3721    2.2610    2.3135 P   0  0  0  0  0  5  0  0  0  0  0  0
   -5.2717    2.5635    3.2744 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4382    3.5885    2.1400 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3096    0.9889    2.9474 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.6674   -4.1900    0.8917 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.5215   -3.3832    2.2657 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.6832   -3.5665    2.3014 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.3954   -1.6978    0.6368 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6405   -2.4604    0.2698 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.4094   -1.2642    2.9981 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8113   -1.6152    2.3678 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.8193   -0.3740   -1.2975 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.7142    1.2388   -1.9741 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3070   -0.4716   -1.2406 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.0724   -0.2674   -2.8792 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5162    2.3626   -1.7343 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5472    3.2058   -3.7091 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2953    3.3653   -1.9543 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3340    3.6926   -3.3606 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3791    1.9598   -3.9194 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1201    3.0882   -1.6412 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6926    1.8398    0.5700 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5658   -0.5638    0.3673 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4223    2.3029   -1.5173 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9145    3.2408   -0.8707 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0637    2.2730   -2.4556 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3759    0.0347   -2.5141 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1695   -0.3980   -1.6119 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3938   -1.0515   -1.0722 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9215    0.9455    0.1111 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3476   -0.0860    0.9724 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3669    2.5085    1.3883 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2986    0.2663    4.5403 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1916   -1.1839    2.0112 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8256   -1.7645    1.0047 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5323    0.0413   -0.7292 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4693   -0.7057   -2.4244 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0928   -0.0167   -2.9251 H   0  0  0  0  0  0  0  0  0  0  0  0
  -12.1414   -4.3254   -2.3638 H   0  0  0  0  0  0  0  0  0  0  0  0
  -12.8735   -3.8643   -0.8059 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4619   -5.1251    1.0907 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1738    0.8562   -0.6320 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8033    1.3696   -2.6701 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8754    0.1574    1.2544 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4647    3.9039    1.2078 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9086    0.6206    3.7795 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
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 20 23  1  0
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 34 35  1  0
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 36 37  1  0
 37 38  1  0
 38 39  2  0
 39 40  1  0
 40 41  2  0
 41 42  1  0
 41 43  1  0
 43 44  2  0
 44 45  1  0
 45 46  2  0
 36 47  1  0
 47 48  1  0
 47 49  1  0
 49 50  1  0
 50 51  1  0
 51 52  2  0
 51 53  1  0
 51 54  1  0
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 46 40  1  0
  1 55  1  0
  1 56  1  0
  1 57  1  0
  2 58  1  6
  3 59  1  0
  4 60  1  0
  4 61  1  0
  8 62  1  0
  8 63  1  0
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 33 84  1  0
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 34 86  1  6
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 44 91  1  0
 47 92  1  1
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 49 94  1  1
 53 95  1  0
 54 96  1  0
M  END

HEADER    PROTEIN                                 25-JUN-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-JUN-20         0                                  
HETATM    1  C   UNK     0      45.863  -3.381   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      44.617  -2.476   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      45.387  -4.845   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      43.371  -3.381   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      43.847  -4.845   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      46.292  -6.091   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      33.271 -10.924   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      34.658 -11.694   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0      31.937 -11.694   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0      30.604 -10.924   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      29.270 -11.694   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      31.990  -8.614   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      30.604  -9.384   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0      31.990  -7.074   0.000  0.00  0.00           N+0
HETATM   15  O   UNK     0      29.323  -7.074   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      30.657  -6.304   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      33.324  -4.764   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      31.220  -2.660   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      31.990  -3.994   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      32.760  -2.660   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      30.657  -4.764   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      29.323  -3.994   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      34.658  -3.994   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      37.738  -3.994   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      40.817  -3.994   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0      36.198  -2.454   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0      36.198  -5.534   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0      39.277  -2.454   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0      39.277  -5.534   0.000  0.00  0.00           O+0
HETATM   30  P   UNK     0      36.198  -3.994   0.000  0.00  0.00           P+0
HETATM   31  P   UNK     0      39.277  -3.994   0.000  0.00  0.00           P+0
HETATM   32  C   UNK     0      41.907  -2.905   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      42.942  -6.091   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0      41.402  -7.631   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0      44.482  -7.631   0.000  0.00  0.00           O+0
HETATM   36  P   UNK     0      42.942  -7.631   0.000  0.00  0.00           P+0
HETATM   37  O   UNK     0      42.942  -9.171   0.000  0.00  0.00           O+0
HETATM   38  N   UNK     0      47.328  -2.905   0.000  0.00  0.00           N+0
HETATM   39  C   UNK     0      48.472  -3.935   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      47.954  -1.498   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      49.806  -3.165   0.000  0.00  0.00           C+0
HETATM   42  N   UNK     0      48.472  -5.475   0.000  0.00  0.00           N+0
HETATM   43  N   UNK     0      49.486  -1.659   0.000  0.00  0.00           N+0
HETATM   44  C   UNK     0      51.140  -3.935   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0      49.806  -6.245   0.000  0.00  0.00           C+0
HETATM   46  N   UNK     0      51.140  -5.475   0.000  0.00  0.00           N+0
HETATM   47  N   UNK     0      52.473  -3.165   0.000  0.00  0.00           N+0
HETATM   48  S   UNK     0      35.991 -10.924   0.000  0.00  0.00           S+0
HETATM   49  O   UNK     0      37.325 -13.234   0.000  0.00  0.00           O+0
HETATM   50  C   UNK     0      37.325 -11.694   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0      38.659 -10.924   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0      41.326 -10.924   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0      39.992 -11.694   0.000  0.00  0.00           C+0
HETATM   54  O   UNK     0      39.992 -13.234   0.000  0.00  0.00           O+0
CONECT    1   38    2    3                                                  
CONECT    2    1    4                                                       
CONECT    3    1    5    6                                                  
CONECT    4    2   32    5                                                  
CONECT    5    3    4   33                                                  
CONECT    6    3                                                            
CONECT    7    9    8                                                       
CONECT    8    7   48                                                       
CONECT    9    7   10                                                       
CONECT   10    9   13   11                                                  
CONECT   11   10                                                            
CONECT   12   14   13                                                       
CONECT   13   10   12                                                       
CONECT   14   12   16                                                       
CONECT   15   16                                                            
CONECT   16   14   15   21                                                  
CONECT   17   19   23                                                       
CONECT   18   19                                                            
CONECT   19   17   18   21   20                                             
CONECT   20   19                                                            
CONECT   21   16   19   22                                                  
CONECT   22   21                                                            
CONECT   23   17   30                                                       
CONECT   24   30   31                                                       
CONECT   25   31   32                                                       
CONECT   26   30                                                            
CONECT   27   30                                                            
CONECT   28   31                                                            
CONECT   29   31                                                            
CONECT   30   23   24   26   27                                             
CONECT   31   24   25   28   29                                             
CONECT   32    4   25                                                       
CONECT   33    5   36                                                       
CONECT   34   36                                                            
CONECT   35   36                                                            
CONECT   36   33   34   35   37                                             
CONECT   37   36                                                            
CONECT   38    1   39   40                                                  
CONECT   39   38   41   42                                                  
CONECT   40   38   43                                                       
CONECT   41   39   44   43                                                  
CONECT   42   39   45                                                       
CONECT   43   40   41                                                       
CONECT   44   41   46   47                                                  
CONECT   45   42   46                                                       
CONECT   46   44   45                                                       
CONECT   47   44                                                            
CONECT   48    8   50                                                       
CONECT   49   50                                                            
CONECT   50   48   49   51                                                  
CONECT   51   50   53                                                       
CONECT   52   53                                                            
CONECT   53   51   52   54                                                  
CONECT   54   53                                                            
MASTER        0    0    0    0    0    0    0    0   54    0  112    0
END

COMPND    HMDB0001166
HETATM    1  C1  UNL     1      10.588  -3.447   1.683  1.00  0.00           C  
HETATM    2  C2  UNL     1      10.439  -2.037   1.003  1.00  0.00           C  
HETATM    3  O1  UNL     1       9.575  -2.337  -0.068  1.00  0.00           O  
HETATM    4  C3  UNL     1       9.811  -1.146   2.016  1.00  0.00           C  
HETATM    5  C4  UNL     1       9.614   0.258   1.704  1.00  0.00           C  
HETATM    6  O2  UNL     1       9.018   0.865   2.692  1.00  0.00           O  
HETATM    7  S1  UNL     1       9.993   1.243   0.350  1.00  0.00           S  
HETATM    8  C5  UNL     1      10.190   0.555  -1.236  1.00  0.00           C  
HETATM    9  C6  UNL     1       8.851   0.198  -1.910  1.00  0.00           C  
HETATM   10  N1  UNL     1       8.125   1.460  -2.055  1.00  0.00           N  
HETATM   11  C7  UNL     1       6.817   1.410  -2.674  1.00  0.00           C  
HETATM   12  O3  UNL     1       6.405   0.300  -3.036  1.00  0.00           O  
HETATM   13  C8  UNL     1       6.087   2.644  -2.825  1.00  0.00           C  
HETATM   14  C9  UNL     1       4.636   2.637  -3.011  1.00  0.00           C  
HETATM   15  N2  UNL     1       3.773   2.247  -1.967  1.00  0.00           N  
HETATM   16  C10 UNL     1       3.541   1.104  -1.230  1.00  0.00           C  
HETATM   17  O4  UNL     1       4.177   0.044  -1.409  1.00  0.00           O  
HETATM   18  C11 UNL     1       2.502   1.027  -0.141  1.00  0.00           C  
HETATM   19  O5  UNL     1       2.681  -0.194   0.557  1.00  0.00           O  
HETATM   20  C12 UNL     1       1.102   1.077  -0.652  1.00  0.00           C  
HETATM   21  C13 UNL     1       0.711   2.304  -1.402  1.00  0.00           C  
HETATM   22  C14 UNL     1       0.912  -0.172  -1.517  1.00  0.00           C  
HETATM   23  C15 UNL     1       0.136   0.914   0.503  1.00  0.00           C  
HETATM   24  O6  UNL     1       0.283   1.918   1.457  1.00  0.00           O  
HETATM   25  P1  UNL     1      -0.832   1.646   2.704  1.00  0.00           P  
HETATM   26  O7  UNL     1      -0.252   2.277   3.961  1.00  0.00           O  
HETATM   27  O8  UNL     1      -2.309   2.406   2.387  1.00  0.00           O  
HETATM   28  O9  UNL     1      -1.087   0.003   2.871  1.00  0.00           O  
HETATM   29  P2  UNL     1      -2.734  -0.321   3.040  1.00  0.00           P  
HETATM   30  O10 UNL     1      -2.851  -1.824   3.297  1.00  0.00           O  
HETATM   31  O11 UNL     1      -3.346   0.426   4.443  1.00  0.00           O  
HETATM   32  O12 UNL     1      -3.644   0.146   1.718  1.00  0.00           O  
HETATM   33  C16 UNL     1      -4.440  -0.886   1.221  1.00  0.00           C  
HETATM   34  C17 UNL     1      -5.208  -0.373   0.045  1.00  0.00           C  
HETATM   35  O13 UNL     1      -6.027  -1.389  -0.495  1.00  0.00           O  
HETATM   36  C18 UNL     1      -6.883  -0.739  -1.374  1.00  0.00           C  
HETATM   37  N3  UNL     1      -8.175  -1.393  -1.496  1.00  0.00           N  
HETATM   38  C19 UNL     1      -9.136  -0.908  -2.296  1.00  0.00           C  
HETATM   39  N4  UNL     1     -10.215  -1.703  -2.217  1.00  0.00           N  
HETATM   40  C20 UNL     1      -9.929  -2.680  -1.372  1.00  0.00           C  
HETATM   41  C21 UNL     1     -10.689  -3.762  -0.936  1.00  0.00           C  
HETATM   42  N5  UNL     1     -12.018  -3.996  -1.382  1.00  0.00           N  
HETATM   43  N6  UNL     1     -10.095  -4.587  -0.059  1.00  0.00           N  
HETATM   44  C22 UNL     1      -8.829  -4.383   0.380  1.00  0.00           C  
HETATM   45  N7  UNL     1      -8.082  -3.341  -0.033  1.00  0.00           N  
HETATM   46  C23 UNL     1      -8.643  -2.487  -0.916  1.00  0.00           C  
HETATM   47  C24 UNL     1      -7.120   0.647  -0.836  1.00  0.00           C  
HETATM   48  O14 UNL     1      -6.550   1.555  -1.730  1.00  0.00           O  
HETATM   49  C25 UNL     1      -6.274   0.624   0.446  1.00  0.00           C  
HETATM   50  O15 UNL     1      -5.797   1.871   0.757  1.00  0.00           O  
HETATM   51  P3  UNL     1      -6.372   2.261   2.314  1.00  0.00           P  
HETATM   52  O16 UNL     1      -5.272   2.564   3.274  1.00  0.00           O  
HETATM   53  O17 UNL     1      -7.438   3.588   2.140  1.00  0.00           O  
HETATM   54  O18 UNL     1      -7.310   0.989   2.947  1.00  0.00           O  
HETATM   55  H1  UNL     1      10.667  -4.190   0.892  1.00  0.00           H  
HETATM   56  H2  UNL     1      11.522  -3.383   2.266  1.00  0.00           H  
HETATM   57  H3  UNL     1       9.683  -3.566   2.301  1.00  0.00           H  
HETATM   58  H4  UNL     1      11.395  -1.698   0.637  1.00  0.00           H  
HETATM   59  H5  UNL     1       8.641  -2.460   0.270  1.00  0.00           H  
HETATM   60  H6  UNL     1      10.409  -1.264   2.998  1.00  0.00           H  
HETATM   61  H7  UNL     1       8.811  -1.615   2.368  1.00  0.00           H  
HETATM   62  H8  UNL     1      10.819  -0.374  -1.298  1.00  0.00           H  
HETATM   63  H9  UNL     1      10.714   1.239  -1.974  1.00  0.00           H  
HETATM   64  H10 UNL     1       8.307  -0.472  -1.241  1.00  0.00           H  
HETATM   65  H11 UNL     1       9.072  -0.267  -2.879  1.00  0.00           H  
HETATM   66  H12 UNL     1       8.516   2.363  -1.734  1.00  0.00           H  
HETATM   67  H13 UNL     1       6.547   3.206  -3.709  1.00  0.00           H  
HETATM   68  H14 UNL     1       6.295   3.365  -1.954  1.00  0.00           H  
HETATM   69  H15 UNL     1       4.334   3.693  -3.361  1.00  0.00           H  
HETATM   70  H16 UNL     1       4.379   1.960  -3.919  1.00  0.00           H  
HETATM   71  H17 UNL     1       3.120   3.088  -1.641  1.00  0.00           H  
HETATM   72  H18 UNL     1       2.693   1.840   0.570  1.00  0.00           H  
HETATM   73  H19 UNL     1       3.566  -0.564   0.367  1.00  0.00           H  
HETATM   74  H20 UNL     1      -0.422   2.303  -1.517  1.00  0.00           H  
HETATM   75  H21 UNL     1       0.914   3.241  -0.871  1.00  0.00           H  
HETATM   76  H22 UNL     1       1.064   2.273  -2.456  1.00  0.00           H  
HETATM   77  H23 UNL     1       1.376   0.035  -2.514  1.00  0.00           H  
HETATM   78  H24 UNL     1      -0.170  -0.398  -1.612  1.00  0.00           H  
HETATM   79  H25 UNL     1       1.394  -1.052  -1.072  1.00  0.00           H  
HETATM   80  H26 UNL     1      -0.921   0.945   0.111  1.00  0.00           H  
HETATM   81  H27 UNL     1       0.348  -0.086   0.972  1.00  0.00           H  
HETATM   82  H28 UNL     1      -2.367   2.508   1.388  1.00  0.00           H  
HETATM   83  H29 UNL     1      -4.299   0.266   4.540  1.00  0.00           H  
HETATM   84  H30 UNL     1      -5.192  -1.184   2.011  1.00  0.00           H  
HETATM   85  H31 UNL     1      -3.826  -1.764   1.005  1.00  0.00           H  
HETATM   86  H32 UNL     1      -4.532   0.041  -0.729  1.00  0.00           H  
HETATM   87  H33 UNL     1      -6.469  -0.706  -2.424  1.00  0.00           H  
HETATM   88  H34 UNL     1      -9.093  -0.017  -2.925  1.00  0.00           H  
HETATM   89  H35 UNL     1     -12.141  -4.325  -2.364  1.00  0.00           H  
HETATM   90  H36 UNL     1     -12.874  -3.864  -0.806  1.00  0.00           H  
HETATM   91  H37 UNL     1      -8.462  -5.125   1.091  1.00  0.00           H  
HETATM   92  H38 UNL     1      -8.174   0.856  -0.632  1.00  0.00           H  
HETATM   93  H39 UNL     1      -6.803   1.370  -2.670  1.00  0.00           H  
HETATM   94  H40 UNL     1      -6.875   0.157   1.254  1.00  0.00           H  
HETATM   95  H41 UNL     1      -7.465   3.904   1.208  1.00  0.00           H  
HETATM   96  H42 UNL     1      -6.909   0.621   3.780  1.00  0.00           H  
CONECT    1    2   55   56   57
CONECT    2    3    4   58
CONECT    3   59
CONECT    4    5   60   61
CONECT    5    6    6    7
CONECT    7    8
CONECT    8    9   62   63
CONECT    9   10   64   65
CONECT   10   11   66
CONECT   11   12   12   13
CONECT   13   14   67   68
CONECT   14   15   69   70
CONECT   15   16   71
CONECT   16   17   17   18
CONECT   18   19   20   72
CONECT   19   73
CONECT   20   21   22   23
CONECT   21   74   75   76
CONECT   22   77   78   79
CONECT   23   24   80   81
CONECT   24   25
CONECT   25   26   26   27   28
CONECT   27   82
CONECT   28   29
CONECT   29   30   30   31   32
CONECT   31   83
CONECT   32   33
CONECT   33   34   84   85
CONECT   34   35   49   86
CONECT   35   36
CONECT   36   37   47   87
CONECT   37   38   46
CONECT   38   39   39   88
CONECT   39   40
CONECT   40   41   41   46
CONECT   41   42   43
CONECT   42   89   90
CONECT   43   44   44
CONECT   44   45   91
CONECT   45   46   46
CONECT   47   48   49   92
CONECT   48   93
CONECT   49   50   94
CONECT   50   51
CONECT   51   52   52   53   54
CONECT   53   95
CONECT   54   96
END

HMDB0001166
     RDKit          3D
3-Hydroxybutyryl-CoA
 96 98  0  0  0  0  0  0  0  0999 V2000
   10.5876   -3.4468    1.6828 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4387   -2.0371    1.0030 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.5753   -2.3368   -0.0684 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.8108   -1.1462    2.0156 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6138    0.2575    1.7044 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0180    0.8651    2.6921 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.9928    1.2429    0.3502 S   0  0  0  0  0  0  0  0  0  0  0  0
   10.1896    0.5547   -1.2360 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8514    0.1976   -1.9104 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1250    1.4605   -2.0550 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.8168    1.4102   -2.6736 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4052    0.3000   -3.0362 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0873    2.6436   -2.8250 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6358    2.6365   -3.0113 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7733    2.2471   -1.9665 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5409    1.1043   -1.2298 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1775    0.0436   -1.4093 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5015    1.0275   -0.1407 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6813   -0.1936    0.5573 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1018    1.0767   -0.6519 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7108    2.3040   -1.4016 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9124   -0.1716   -1.5174 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1361    0.9143    0.5030 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2827    1.9184    1.4566 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8324    1.6458    2.7037 P   0  0  0  0  0  5  0  0  0  0  0  0
   -0.2523    2.2767    3.9607 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3090    2.4065    2.3874 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0874    0.0027    2.8706 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7344   -0.3205    3.0399 P   0  0  0  0  0  5  0  0  0  0  0  0
   -2.8514   -1.8242    3.2974 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3462    0.4261    4.4433 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6438    0.1462    1.7180 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4402   -0.8859    1.2214 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2085   -0.3735    0.0455 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.0267   -1.3893   -0.4951 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8832   -0.7388   -1.3743 C   0  0  1  0  0  0  0  0  0  0  0  0
   -8.1750   -1.3929   -1.4962 N   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1364   -0.9076   -2.2960 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.2152   -1.7026   -2.2171 N   0  0  0  0  0  0  0  0  0  0  0  0
   -9.9290   -2.6803   -1.3716 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.6895   -3.7623   -0.9359 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.0184   -3.9962   -1.3821 N   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0952   -4.5871   -0.0591 N   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8287   -4.3835    0.3802 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0819   -3.3411   -0.0329 N   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6434   -2.4873   -0.9157 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1204    0.6466   -0.8362 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.5502    1.5548   -1.7300 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2741    0.6235    0.4458 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.7970    1.8715    0.7565 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3721    2.2610    2.3135 P   0  0  0  0  0  5  0  0  0  0  0  0
   -5.2717    2.5635    3.2744 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4382    3.5885    2.1400 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3096    0.9889    2.9474 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.6674   -4.1900    0.8917 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.5215   -3.3832    2.2657 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.6832   -3.5665    2.3014 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.3954   -1.6978    0.6368 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6405   -2.4604    0.2698 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.4094   -1.2642    2.9981 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8113   -1.6152    2.3678 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.8193   -0.3740   -1.2975 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.7142    1.2388   -1.9741 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3070   -0.4716   -1.2406 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.0724   -0.2674   -2.8792 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5162    2.3626   -1.7343 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5472    3.2058   -3.7091 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2953    3.3653   -1.9543 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3340    3.6926   -3.3606 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3791    1.9598   -3.9194 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1201    3.0882   -1.6412 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6926    1.8398    0.5700 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5658   -0.5638    0.3673 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4223    2.3029   -1.5173 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9145    3.2408   -0.8707 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0637    2.2730   -2.4556 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3759    0.0347   -2.5141 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1695   -0.3980   -1.6119 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3938   -1.0515   -1.0722 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9215    0.9455    0.1111 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3476   -0.0860    0.9724 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3669    2.5085    1.3883 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2986    0.2663    4.5403 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1916   -1.1839    2.0112 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8256   -1.7645    1.0047 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5323    0.0413   -0.7292 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4693   -0.7057   -2.4244 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0928   -0.0167   -2.9251 H   0  0  0  0  0  0  0  0  0  0  0  0
  -12.1414   -4.3254   -2.3638 H   0  0  0  0  0  0  0  0  0  0  0  0
  -12.8735   -3.8643   -0.8059 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4619   -5.1251    1.0907 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1738    0.8562   -0.6320 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8033    1.3696   -2.6701 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8754    0.1574    1.2544 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4647    3.9039    1.2078 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9086    0.6206    3.7795 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 20 22  1  0
 20 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  2  0
 25 27  1  0
 25 28  1  0
 28 29  1  0
 29 30  2  0
 29 31  1  0
 29 32  1  0
 32 33  1  0
 33 34  1  0
 34 35  1  0
 35 36  1  0
 36 37  1  0
 37 38  1  0
 38 39  2  0
 39 40  1  0
 40 41  2  0
 41 42  1  0
 41 43  1  0
 43 44  2  0
 44 45  1  0
 45 46  2  0
 36 47  1  0
 47 48  1  0
 47 49  1  0
 49 50  1  0
 50 51  1  0
 51 52  2  0
 51 53  1  0
 51 54  1  0
 49 34  1  0
 46 37  1  0
 46 40  1  0
  1 55  1  0
  1 56  1  0
  1 57  1  0
  2 58  1  6
  3 59  1  0
  4 60  1  0
  4 61  1  0
  8 62  1  0
  8 63  1  0
  9 64  1  0
  9 65  1  0
 10 66  1  0
 13 67  1  0
 13 68  1  0
 14 69  1  0
 14 70  1  0
 15 71  1  0
 18 72  1  1
 19 73  1  0
 21 74  1  0
 21 75  1  0
 21 76  1  0
 22 77  1  0
 22 78  1  0
 22 79  1  0
 23 80  1  0
 23 81  1  0
 27 82  1  0
 31 83  1  0
 33 84  1  0
 33 85  1  0
 34 86  1  6
 36 87  1  6
 38 88  1  0
 42 89  1  0
 42 90  1  0
 44 91  1  0
 47 92  1  1
 48 93  1  0
 49 94  1  1
 53 95  1  0
 54 96  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
(3R)-3-Hydroxybutanoyl-CoA	ChEBI
(R)-3-Hydroxy-butanoyl-CoA	HMDB
(R)-3-Hydroxy-butanoyl-coenzyme A	HMDB
(R)-3-Hydroxybutyryl CoA	HMDB
3-Hydroxybutyryl-CoA	HMDB
3-Hydroxybutyryl-coenzyme A	HMDB
D-(-)-beta-Hydroxybutyryl-CoA	HMDB
D-(-)-beta-Hydroxybutyryl-coenzyme A	HMDB
D-(-)-β-Hydroxybutyryl-CoA	HMDB
D-(-)-β-Hydroxybutyryl-coenzyme A	HMDB
D-3-Hydroxybutyryl-CoA	HMDB
D-3-Hydroxybutyryl-coenzyme A	HMDB
D-beta-Hydroxybutyryl-CoA	HMDB
D-beta-Hydroxybutyryl-coenzyme A	HMDB
D-β-Hydroxybutyryl-CoA	HMDB
D-β-Hydroxybutyryl-coenzyme A	HMDB
R-(-)-3-Hydroxybutyryl-CoA	HMDB
R-(-)-3-Hydroxybutyryl-coenzyme A	HMDB
beta-Hydroxybutyryl CoA	HMDB
beta-Hydroxybutyryl coenzyme A	HMDB
β-Hydroxybutyryl CoA	HMDB
β-Hydroxybutyryl coenzyme A	HMDB

Chemical Formula

C₂₅H₄₂N₇O₁₈P₃S

Average Molecular Weight

853.62

Monoisotopic Molecular Weight

853.151989708

IUPAC Name

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

Traditional Name

(R)-3-hydroxybutanoyl-coa

CAS Registry Number

21804-29-5

SMILES

C[C@@H](O)CC(=O)SCCNC(=O)CCNC(=O)[C@H](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=C1N=CN=C2N

InChI Identifier

InChI=1S/C25H42N7O18P3S/c1-13(33)8-16(35)54-7-6-27-15(34)4-5-28-23(38)20(37)25(2,3)10-47-53(44,45)50-52(42,43)46-9-14-19(49-51(39,40)41)18(36)24(48-14)32-12-31-17-21(26)29-11-30-22(17)32/h11-14,18-20,24,33,36-37H,4-10H2,1-3H3,(H,27,34)(H,28,38)(H,42,43)(H,44,45)(H2,26,29,30)(H2,39,40,41)/t13-,14-,18-,19-,20+,24-/m1/s1

InChI Key

QHHKKMYHDBRONY-WZZMXTMRSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as (r)-3-hydroxyacyl coas. These are organic compounds containing a (R)-3-hydroxyl acylated coenzyme A derivative.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acyl thioesters

Direct Parent

(R)-3-hydroxyacyl 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

3-hydroxybutanoyl-CoA (CHEBI:15452 )

Ontology

Physiological effect

Adverse health effect

Genetic disorder

Inborn errors of metabolism

Ethylmalonic encephalopathy (PMID: 10731506 , PMID: 27012787 , PMID: 3571488 , +12

Source	Link
Pubmed	PMID: 10731506
Pubmed	PMID: 27012787
Pubmed	PMID: 3571488
Pubmed	PMID: 7776094
Pubmed	PMID: 8087979
Pubmed	PMID: 31963255
Pubmed	PMID: 16828325
Pubmed	PMID: 10197568
Pubmed	PMID: 7609451
Pubmed	PMID: 7609451
Pubmed	PMID: 2026685
Pubmed	PMID: 9177981
Pubmed	PMID: 16828325
Pubmed	PMID: 16460720
Pubmed	PMID: 24023812

)

Disposition

Biological location

Cellular substructure

Extracellular

Organelle

Peroxisome

Horse

Lagomorphs

Ovis

Sheep (Mutton, Lamb)

Caprae

Domestic goat

Process

Naturally occurring process

Fatty acid metabolism

Physical Properties

State

Solid

Experimental Molecular Properties

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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	4.07 g/L	ALOGPS
logP	-0.62	ALOGPS
logP	-6	ChemAxon
logS	-2.3	ALOGPS
pKa (Strongest Acidic)	0.82	ChemAxon
pKa (Strongest Basic)	4.01	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	22	ChemAxon
Refractivity	183.03 m³·mol⁻¹	ChemAxon
Polarizability	77.23 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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	204.179	30932474
DeepCCS	[M-H]-	202.526	30932474
DeepCCS	[M-2H]-	236.56	30932474
DeepCCS	[M+Na]+	210.336	30932474

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
3-Hydroxybutyryl-CoA	C[C@@H](O)CC(=O)SCCNC(=O)CCNC(=O)[C@H](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=C1N=CN=C2N	5803.6	Standard polar	33892256
3-Hydroxybutyryl-CoA	C[C@@H](O)CC(=O)SCCNC(=O)CCNC(=O)[C@H](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=C1N=CN=C2N	4292.7	Standard non polar	33892256
3-Hydroxybutyryl-CoA	C[C@@H](O)CC(=O)SCCNC(=O)CCNC(=O)[C@H](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=C1N=CN=C2N	6560.4	Semi standard non polar	33892256

Spectra

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxybutyryl-CoA 10V, Positive-QTOF	splash10-000i-1912000140-eba415fd46f47c10a045	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxybutyryl-CoA 20V, Positive-QTOF	splash10-000i-1914000000-aae3b11040f7ee3ffbb4	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxybutyryl-CoA 40V, Positive-QTOF	splash10-000i-1910000000-5c259b64dc19ad3be272	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxybutyryl-CoA 10V, Negative-QTOF	splash10-053r-9720140460-7f9422084aa5ef2f6c4e	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxybutyryl-CoA 20V, Negative-QTOF	splash10-001i-5920120010-46ef6c69443d2b7286e2	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxybutyryl-CoA 40V, Negative-QTOF	splash10-0a7i-5900100000-5010983cc099f69bf8f0	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxybutyryl-CoA 10V, Negative-QTOF	splash10-0udi-0000000190-d473b36a9239d68c3968	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxybutyryl-CoA 20V, Negative-QTOF	splash10-0fv0-7500104960-d5a9b05839a7099bb9c8	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxybutyryl-CoA 40V, Negative-QTOF	splash10-0fvs-6002504910-fcc4f9405d0cdb56506c	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxybutyryl-CoA 10V, Positive-QTOF	splash10-0udi-0000000190-10a5a939008a51384a4d	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxybutyryl-CoA 20V, Positive-QTOF	splash10-000i-0901001470-a6ff0d6eff5b7a93c01a	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxybutyryl-CoA 40V, Positive-QTOF	splash10-0002-0029000000-3cbf971409e55f5f2d9b	2021-09-25	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane
Mitochondria
Peroxisome

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Name	SMPDB/PathBank	KEGG
Butyrate Metabolism
Fatty acid Metabolism
Lysine degradation	Not Available
Mitochondrial Beta-Oxidation of Short Chain Saturated Fatty Acids		Not Available
Ethylmalonic Encephalopathy		Not Available

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022460

KNApSAcK ID

Not Available

Chemspider ID

10140140

KEGG Compound ID

C03561

BioCyc ID

CPD-650

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

456

PubChem Compound

11966146

PDB ID

Not Available

ChEBI ID

15452

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Gerngross TU, Snell KD, Peoples OP, Sinskey AJ, Csuhai E, Masamune S, Stubbe J: Overexpression and purification of the soluble polyhydroxyalkanoate synthase from Alcaligenes eutrophus: evidence for a required posttranslational modification for catalytic activity. Biochemistry. 1994 Aug 9;33(31):9311-20. [PubMed:8049232 ]
Kraak MN, Kessler B, Witholt B: In vitro activities of granule-bound poly[(R)-3-hydroxyalkanoate]polymerase C1 of Pseudomonas oleovorans--development of an activity test for medium-chain-length-poly(3-hydroxyalkanoate) polymerases. Eur J Biochem. 1997 Dec 1;250(2):432-9. [PubMed:9428695 ]
Emmett B, Hochachka PW: Scaling of oxidative and glycolytic enzymes in mammals. Respir Physiol. 1981 Sep;45(3):261-72. [PubMed:7036306 ]

Enzymes

Enzyme Details

1. Peroxisomal bifunctional enzyme

General function:: Involved in oxidoreductase activity
Specific function:: Not Available
Gene Name:: EHHADH
Uniprot ID:: Q08426
Molecular weight:: 69153.26

Reactions

3-Hydroxybutyryl-CoA + NAD → Acetoacetyl-CoA + NADH + Hydrogen Ion	details
3-Hydroxybutyryl-CoA → Crotonoyl-CoA + Water	details
Crotonoyl-CoA + Water → 3-Hydroxybutyryl-CoA	details

Enzyme Details

2. Hydroxyacyl-coenzyme A dehydrogenase, mitochondrial

General function:: Involved in 3-hydroxyacyl-CoA dehydrogenase activity
Specific function:: Plays an essential role in the mitochondrial beta-oxidation of short chain fatty acids. Exerts it highest activity toward 3-hydroxybutyryl-CoA.
Gene Name:: HADH
Uniprot ID:: Q16836
Molecular weight:: 36035.11

Reactions

3-Hydroxybutyryl-CoA + NAD → Acetoacetyl-CoA + NADH + Hydrogen Ion	details

Enzyme Details

3. Enoyl-CoA hydratase, mitochondrial

General function:: Involved in catalytic activity
Specific function:: Straight-chain enoyl-CoA thioesters from C4 up to at least C16 are processed, although with decreasing catalytic rate.
Gene Name:: ECHS1
Uniprot ID:: P30084
Molecular weight:: 31387.085

Reactions

3-Hydroxybutyryl-CoA → Crotonoyl-CoA + Water	details
Crotonoyl-CoA + Water → 3-Hydroxybutyryl-CoA	details

Enzyme Details

4. Trifunctional enzyme subunit alpha, mitochondrial

General function:: Involved in oxidoreductase activity
Specific function:: Bifunctional subunit.
Gene Name:: HADHA
Uniprot ID:: P40939
Molecular weight:: 82998.97

Reactions

3-Hydroxybutyryl-CoA → Crotonoyl-CoA + Water	details
Crotonoyl-CoA + Water → 3-Hydroxybutyryl-CoA	details

Showing metabocard for 3-Hydroxybutyryl-CoA (HMDB0001166)

MOL for HMDB0001166 (3-Hydroxybutyryl-CoA)

3D MOL for HMDB0001166 (3-Hydroxybutyryl-CoA)

3D SDF for HMDB0001166 (3-Hydroxybutyryl-CoA)

3D-SDF for HMDB0001166 (3-Hydroxybutyryl-CoA)

PDB for HMDB0001166 (3-Hydroxybutyryl-CoA)

3D PDB for HMDB0001166 (3-Hydroxybutyryl-CoA)

SMILES for HMDB0001166 (3-Hydroxybutyryl-CoA)

INCHI for HMDB0001166 (3-Hydroxybutyryl-CoA)

Structure for HMDB0001166 (3-Hydroxybutyryl-CoA)

3D Structure for HMDB0001166 (3-Hydroxybutyryl-CoA)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

MS/MS Spectra

NMR Spectra

Enzymes

Reactions

Reactions

Reactions

Reactions