MiMeDB: Showing metabocard for Cholestenone (MMDBc0000379)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2020-12-10 18:36:29 UTC

Update Date

2024-04-30 19:32:01 UTC

Metabolite ID

MMDBc0000379

Metabolite Identification

Common Name

Cholestenone

Description

Cholestenone belongs to the class of organic compounds known as cholesterols and derivatives. Cholesterols and derivatives are compounds containing a 3-hydroxylated cholestane core. Thus, cholestenone is considered to be a sterol lipid molecule. Cholestenone is a very hydrophobic molecule, practically insoluble in water, and relatively neutral.

Structure

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

 
  Mrv1652310251916462D          

 32 35  0  0  1  0            999 V2000
   15.0865  -16.9659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0865  -17.7909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8009  -18.2034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5154  -17.7909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5154  -16.9659    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   15.8009  -16.5535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2298  -18.2034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9442  -17.7909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9442  -16.9659    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   17.2298  -16.5535    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   17.9442  -15.3160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2298  -15.7285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3720  -18.2034    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.2298  -17.3785    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   18.6587  -17.3785    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   16.5154  -16.1410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9442  -16.1410    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   18.6587  -14.9035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6587  -15.7285    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   18.6587  -16.5534    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   19.4433  -16.8084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9282  -16.1410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4433  -15.4735    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   19.4433  -14.6485    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   20.1602  -14.2345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8659  -14.6421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5651  -14.2383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2675  -14.6441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9684  -14.2394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2675  -15.4733    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7312  -14.2372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1718  -15.0528    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  4  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  5 10  1  0  0  0  0
 11 12  1  0  0  0  0
 10 12  1  0  0  0  0
  2 13  2  0  0  0  0
 10 14  1  6  0  0  0
  5 16  1  1  0  0  0
  9 17  1  1  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 28 30  1  0  0  0  0
 24 31  1  6  0  0  0
 23 32  1  6  0  0  0
 23 19  1  0  0  0  0
 23 22  1  0  0  0  0
  9 20  1  0  0  0  0
 20 15  1  6  0  0  0
 19 11  1  0  0  0  0
 19 18  1  1  0  0  0
M  END

HMDB0000921
     RDKit          3D
Cholestenone
 72 75  0  0  0  0  0  0  0  0999 V2000
   -6.9423   -0.0637   -1.1512 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6598    0.9421   -0.0605 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7308    2.3586   -0.5781 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2206    0.6937    0.4175 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2874    0.8798   -0.7366 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8186    0.6691   -0.3660 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5667   -0.7220    0.1519 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.9288   -1.6787   -0.9145 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2580   -0.8438    0.8231 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0085   -2.2441    1.3495 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4661   -2.5536    1.0423 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0188   -1.1672    1.0104 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4245   -1.0215    0.5861 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3132   -1.5117    1.6962 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4626   -0.6575    2.0667 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9618    0.2600    1.0365 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1140    0.8655    1.1991 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6636    1.7889    0.2127 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7146    2.4473    0.4006 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9454    1.9545   -1.0685 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4821    1.8050   -0.8363 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1393    0.4908   -0.1759 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.3778   -0.6110   -1.1864 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7174    0.4139    0.3118 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7112    1.0979   -0.5442 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3782    0.9905    0.2054 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0171   -0.4661    0.1452 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1195   -1.0054   -1.2606 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0392   -0.2834   -1.1866 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6427    0.3674   -2.1465 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3700   -0.9964   -1.0232 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3421    0.7870    0.8180 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7132    2.7815   -0.2758 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6226    2.2963   -1.6881 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9582    3.0148   -0.1286 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2565   -0.3764    0.7793 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9620    1.3343    1.2665 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3719    1.9336   -1.0615 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5949    0.1883   -1.5641 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1795    0.9049   -1.2487 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5973    1.4088    0.4225 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3360   -0.8679    0.9770 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6642   -2.7329   -0.7511 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6443   -1.3305   -1.9453 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0620   -1.6902   -0.9775 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3290   -0.1907    1.7495 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6693   -3.0097    0.9543 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0535   -2.2642    2.4754 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5990   -3.0388    0.0737 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9092   -3.1967    1.8219 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8635   -0.7406    2.0406 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6425   -1.6874   -0.2807 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6891   -2.5536    1.4958 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7163   -1.6550    2.6520 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3403   -1.3354    2.3099 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3083   -0.1240    3.0540 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7367    0.7110    2.0944 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3892    1.2236   -1.7758 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1455    2.9494   -1.5339 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1187    2.6830   -0.2956 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9651    1.7920   -1.8341 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6340   -1.5803   -0.6696 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4900   -0.7427   -1.8692 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224   -0.4273   -1.8639 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6859    0.9437    1.3107 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6464    0.7476   -1.5727 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9522    2.1822   -0.5494 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3129    1.7136   -0.1681 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6060    1.2282    1.2651 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1615   -1.2249   -1.5611 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4218   -1.9785   -1.3333 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2497   -0.2749   -2.0326 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  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  6
 22 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  6
 27  9  1  0
 27 12  1  0
 24 13  1  0
 22 16  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  2 32  1  0
  3 33  1  0
  3 34  1  0
  3 35  1  0
  4 36  1  0
  4 37  1  0
  5 38  1  0
  5 39  1  0
  6 40  1  0
  6 41  1  0
  7 42  1  1
  8 43  1  0
  8 44  1  0
  8 45  1  0
  9 46  1  1
 10 47  1  0
 10 48  1  0
 11 49  1  0
 11 50  1  0
 12 51  1  1
 13 52  1  6
 14 53  1  0
 14 54  1  0
 15 55  1  0
 15 56  1  0
 17 57  1  0
 20 58  1  0
 20 59  1  0
 21 60  1  0
 21 61  1  0
 23 62  1  0
 23 63  1  0
 23 64  1  0
 24 65  1  1
 25 66  1  0
 25 67  1  0
 26 68  1  0
 26 69  1  0
 28 70  1  0
 28 71  1  0
 28 72  1  0
M  END

 
  Mrv1652310251916462D          

 32 35  0  0  1  0            999 V2000
   15.0865  -16.9659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0865  -17.7909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8009  -18.2034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5154  -17.7909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5154  -16.9659    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   15.8009  -16.5535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2298  -18.2034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9442  -17.7909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9442  -16.9659    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   17.2298  -16.5535    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   17.9442  -15.3160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2298  -15.7285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3720  -18.2034    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.2298  -17.3785    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   18.6587  -17.3785    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   16.5154  -16.1410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9442  -16.1410    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   18.6587  -14.9035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6587  -15.7285    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   18.6587  -16.5534    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   19.4433  -16.8084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9282  -16.1410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4433  -15.4735    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   19.4433  -14.6485    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   20.1602  -14.2345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8659  -14.6421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5651  -14.2383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2675  -14.6441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9684  -14.2394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2675  -15.4733    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7312  -14.2372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1718  -15.0528    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  4  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  5 10  1  0  0  0  0
 11 12  1  0  0  0  0
 10 12  1  0  0  0  0
  2 13  2  0  0  0  0
 10 14  1  6  0  0  0
  5 16  1  1  0  0  0
  9 17  1  1  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 28 30  1  0  0  0  0
 24 31  1  6  0  0  0
 23 32  1  6  0  0  0
 23 19  1  0  0  0  0
 23 22  1  0  0  0  0
  9 20  1  0  0  0  0
 20 15  1  6  0  0  0
 19 11  1  0  0  0  0
 19 18  1  1  0  0  0
M  END
> <DATABASE_ID>
MMDBc0000379

> <DATABASE_NAME>
MIME

> <SMILES>
[H][C@@]1(CC[C@@]2([H])[C@]3([H])CCC4=CC(=O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCCC(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C27H44O/c1-18(2)7-6-8-19(3)23-11-12-24-22-10-9-20-17-21(28)13-15-26(20,4)25(22)14-16-27(23,24)5/h17-19,22-25H,6-16H2,1-5H3/t19-,22+,23-,24+,25+,26+,27-/m1/s1

> <INCHI_KEY>
NYOXRYYXRWJDKP-GYKMGIIDSA-N

> <FORMULA>
C27H44O

> <MOLECULAR_WEIGHT>
384.6377

> <EXACT_MASS>
384.33921603

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
72

> <JCHEM_AVERAGE_POLARIZABILITY>
49.790733935790115

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,2R,10S,11S,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one

> <ALOGPS_LOGP>
6.57

> <JCHEM_LOGP>
7.680134978666665

> <ALOGPS_LOGS>
-7.23

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
19.087826253912564

> <JCHEM_PKA_STRONGEST_BASIC>
-4.817440235063846

> <JCHEM_POLAR_SURFACE_AREA>
17.07

> <JCHEM_REFRACTIVITY>
119.56509999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.27e-05 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2R,10S,11S,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0000921
     RDKit          3D
Cholestenone
 72 75  0  0  0  0  0  0  0  0999 V2000
   -6.9423   -0.0637   -1.1512 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6598    0.9421   -0.0605 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7308    2.3586   -0.5781 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2206    0.6937    0.4175 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2874    0.8798   -0.7366 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8186    0.6691   -0.3660 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5667   -0.7220    0.1519 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.9288   -1.6787   -0.9145 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2580   -0.8438    0.8231 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0085   -2.2441    1.3495 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4661   -2.5536    1.0423 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0188   -1.1672    1.0104 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4245   -1.0215    0.5861 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3132   -1.5117    1.6962 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4626   -0.6575    2.0667 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9618    0.2600    1.0365 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1140    0.8655    1.1991 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6636    1.7889    0.2127 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7146    2.4473    0.4006 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9454    1.9545   -1.0685 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4821    1.8050   -0.8363 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1393    0.4908   -0.1759 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.3778   -0.6110   -1.1864 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7174    0.4139    0.3118 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7112    1.0979   -0.5442 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3782    0.9905    0.2054 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0171   -0.4661    0.1452 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1195   -1.0054   -1.2606 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0392   -0.2834   -1.1866 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6427    0.3674   -2.1465 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3700   -0.9964   -1.0232 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3421    0.7870    0.8180 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7132    2.7815   -0.2758 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6226    2.2963   -1.6881 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9582    3.0148   -0.1286 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2565   -0.3764    0.7793 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9620    1.3343    1.2665 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3719    1.9336   -1.0615 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5949    0.1883   -1.5641 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1795    0.9049   -1.2487 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5973    1.4088    0.4225 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3360   -0.8679    0.9770 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6642   -2.7329   -0.7511 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6443   -1.3305   -1.9453 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0620   -1.6902   -0.9775 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3290   -0.1907    1.7495 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6693   -3.0097    0.9543 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0535   -2.2642    2.4754 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5990   -3.0388    0.0737 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9092   -3.1967    1.8219 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8635   -0.7406    2.0406 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6425   -1.6874   -0.2807 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6891   -2.5536    1.4958 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7163   -1.6550    2.6520 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3403   -1.3354    2.3099 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3083   -0.1240    3.0540 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7367    0.7110    2.0944 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3892    1.2236   -1.7758 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1455    2.9494   -1.5339 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1187    2.6830   -0.2956 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9651    1.7920   -1.8341 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6340   -1.5803   -0.6696 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4900   -0.7427   -1.8692 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224   -0.4273   -1.8639 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6859    0.9437    1.3107 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6464    0.7476   -1.5727 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9522    2.1822   -0.5494 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3129    1.7136   -0.1681 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6060    1.2282    1.2651 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1615   -1.2249   -1.5611 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4218   -1.9785   -1.3333 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2497   -0.2749   -2.0326 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  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  6
 22 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  6
 27  9  1  0
 27 12  1  0
 24 13  1  0
 22 16  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  2 32  1  0
  3 33  1  0
  3 34  1  0
  3 35  1  0
  4 36  1  0
  4 37  1  0
  5 38  1  0
  5 39  1  0
  6 40  1  0
  6 41  1  0
  7 42  1  1
  8 43  1  0
  8 44  1  0
  8 45  1  0
  9 46  1  1
 10 47  1  0
 10 48  1  0
 11 49  1  0
 11 50  1  0
 12 51  1  1
 13 52  1  6
 14 53  1  0
 14 54  1  0
 15 55  1  0
 15 56  1  0
 17 57  1  0
 20 58  1  0
 20 59  1  0
 21 60  1  0
 21 61  1  0
 23 62  1  0
 23 63  1  0
 23 64  1  0
 24 65  1  1
 25 66  1  0
 25 67  1  0
 26 68  1  0
 26 69  1  0
 28 70  1  0
 28 71  1  0
 28 72  1  0
M  END

HEADER    PROTEIN                                 25-OCT-19   NONE
TITLE     NULL                                                        
COMPND    MOLECULE:                                                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-OCT-19         0                                  
HETATM    1  C   UNK     0      28.161 -31.670   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      28.161 -33.210   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      29.495 -33.980   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      30.829 -33.210   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      30.829 -31.670   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      29.495 -30.900   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      32.162 -33.980   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      33.496 -33.210   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      33.496 -31.670   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      32.162 -30.900   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      33.496 -28.590   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      32.162 -29.360   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      26.828 -33.980   0.000  0.00  0.00           O+0
HETATM   14  H   UNK     0      32.162 -32.440   0.000  0.00  0.00           H+0
HETATM   15  H   UNK     0      34.830 -32.440   0.000  0.00  0.00           H+0
HETATM   16  C   UNK     0      30.829 -30.130   0.000  0.00  0.00           C+0
HETATM   17  H   UNK     0      33.496 -30.130   0.000  0.00  0.00           H+0
HETATM   18  C   UNK     0      34.830 -27.820   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      34.830 -29.360   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      34.830 -30.900   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      36.294 -31.376   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      37.199 -30.130   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      36.294 -28.884   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      36.294 -27.344   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      37.632 -26.571   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      38.950 -27.332   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      40.255 -26.578   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      41.566 -27.336   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      42.874 -26.580   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      41.566 -28.883   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      34.965 -26.576   0.000  0.00  0.00           C+0
HETATM   32  H   UNK     0      37.654 -28.099   0.000  0.00  0.00           H+0
CONECT    1    2    6                                                       
CONECT    2    1    3   13                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    7                                                  
CONECT    5    4    6   10   16                                             
CONECT    6    5    1                                                       
CONECT    7    4    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   17   20                                             
CONECT   10    9    5   12   14                                             
CONECT   11   12   19                                                       
CONECT   12   11   10                                                       
CONECT   13    2                                                            
CONECT   14   10                                                            
CONECT   15   20                                                            
CONECT   16    5                                                            
CONECT   17    9                                                            
CONECT   18   19                                                            
CONECT   19   20   23   11   18                                             
CONECT   20   19   21    9   15                                             
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   24   32   19   22                                             
CONECT   24   23   25   31                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28                                                            
CONECT   31   24                                                            
CONECT   32   23                                                            
MASTER        0    0    0    0    0    0    0    0   32    0   70    0
END

COMPND    HMDB0000921
HETATM    1  C1  UNL     1      -6.942  -0.064  -1.151  1.00  0.00           C  
HETATM    2  C2  UNL     1      -6.660   0.942  -0.060  1.00  0.00           C  
HETATM    3  C3  UNL     1      -6.731   2.359  -0.578  1.00  0.00           C  
HETATM    4  C4  UNL     1      -5.221   0.694   0.417  1.00  0.00           C  
HETATM    5  C5  UNL     1      -4.287   0.880  -0.737  1.00  0.00           C  
HETATM    6  C6  UNL     1      -2.819   0.669  -0.366  1.00  0.00           C  
HETATM    7  C7  UNL     1      -2.567  -0.722   0.152  1.00  0.00           C  
HETATM    8  C8  UNL     1      -2.929  -1.679  -0.915  1.00  0.00           C  
HETATM    9  C9  UNL     1      -1.258  -0.844   0.823  1.00  0.00           C  
HETATM   10  C10 UNL     1      -1.009  -2.244   1.350  1.00  0.00           C  
HETATM   11  C11 UNL     1       0.466  -2.554   1.042  1.00  0.00           C  
HETATM   12  C12 UNL     1       1.019  -1.167   1.010  1.00  0.00           C  
HETATM   13  C13 UNL     1       2.425  -1.021   0.586  1.00  0.00           C  
HETATM   14  C14 UNL     1       3.313  -1.512   1.696  1.00  0.00           C  
HETATM   15  C15 UNL     1       4.463  -0.658   2.067  1.00  0.00           C  
HETATM   16  C16 UNL     1       4.962   0.260   1.037  1.00  0.00           C  
HETATM   17  C17 UNL     1       6.114   0.865   1.199  1.00  0.00           C  
HETATM   18  C18 UNL     1       6.664   1.789   0.213  1.00  0.00           C  
HETATM   19  O1  UNL     1       7.715   2.447   0.401  1.00  0.00           O  
HETATM   20  C19 UNL     1       5.945   1.954  -1.068  1.00  0.00           C  
HETATM   21  C20 UNL     1       4.482   1.805  -0.836  1.00  0.00           C  
HETATM   22  C21 UNL     1       4.139   0.491  -0.176  1.00  0.00           C  
HETATM   23  C22 UNL     1       4.378  -0.611  -1.186  1.00  0.00           C  
HETATM   24  C23 UNL     1       2.717   0.414   0.312  1.00  0.00           C  
HETATM   25  C24 UNL     1       1.711   1.098  -0.544  1.00  0.00           C  
HETATM   26  C25 UNL     1       0.378   0.990   0.205  1.00  0.00           C  
HETATM   27  C26 UNL     1      -0.017  -0.466   0.145  1.00  0.00           C  
HETATM   28  C27 UNL     1       0.119  -1.005  -1.261  1.00  0.00           C  
HETATM   29  H1  UNL     1      -8.039  -0.283  -1.187  1.00  0.00           H  
HETATM   30  H2  UNL     1      -6.643   0.367  -2.146  1.00  0.00           H  
HETATM   31  H3  UNL     1      -6.370  -0.996  -1.023  1.00  0.00           H  
HETATM   32  H4  UNL     1      -7.342   0.787   0.818  1.00  0.00           H  
HETATM   33  H5  UNL     1      -7.713   2.781  -0.276  1.00  0.00           H  
HETATM   34  H6  UNL     1      -6.623   2.296  -1.688  1.00  0.00           H  
HETATM   35  H7  UNL     1      -5.958   3.015  -0.129  1.00  0.00           H  
HETATM   36  H8  UNL     1      -5.257  -0.376   0.779  1.00  0.00           H  
HETATM   37  H9  UNL     1      -4.962   1.334   1.266  1.00  0.00           H  
HETATM   38  H10 UNL     1      -4.372   1.934  -1.062  1.00  0.00           H  
HETATM   39  H11 UNL     1      -4.595   0.188  -1.564  1.00  0.00           H  
HETATM   40  H12 UNL     1      -2.179   0.905  -1.249  1.00  0.00           H  
HETATM   41  H13 UNL     1      -2.597   1.409   0.423  1.00  0.00           H  
HETATM   42  H14 UNL     1      -3.336  -0.868   0.977  1.00  0.00           H  
HETATM   43  H15 UNL     1      -2.664  -2.733  -0.751  1.00  0.00           H  
HETATM   44  H16 UNL     1      -2.644  -1.330  -1.945  1.00  0.00           H  
HETATM   45  H17 UNL     1      -4.062  -1.690  -0.977  1.00  0.00           H  
HETATM   46  H18 UNL     1      -1.329  -0.191   1.750  1.00  0.00           H  
HETATM   47  H19 UNL     1      -1.669  -3.010   0.954  1.00  0.00           H  
HETATM   48  H20 UNL     1      -1.053  -2.264   2.475  1.00  0.00           H  
HETATM   49  H21 UNL     1       0.599  -3.039   0.074  1.00  0.00           H  
HETATM   50  H22 UNL     1       0.909  -3.197   1.822  1.00  0.00           H  
HETATM   51  H23 UNL     1       0.863  -0.741   2.041  1.00  0.00           H  
HETATM   52  H24 UNL     1       2.643  -1.687  -0.281  1.00  0.00           H  
HETATM   53  H25 UNL     1       3.689  -2.554   1.496  1.00  0.00           H  
HETATM   54  H26 UNL     1       2.716  -1.655   2.652  1.00  0.00           H  
HETATM   55  H27 UNL     1       5.340  -1.335   2.310  1.00  0.00           H  
HETATM   56  H28 UNL     1       4.308  -0.124   3.054  1.00  0.00           H  
HETATM   57  H29 UNL     1       6.737   0.711   2.094  1.00  0.00           H  
HETATM   58  H30 UNL     1       6.389   1.224  -1.776  1.00  0.00           H  
HETATM   59  H31 UNL     1       6.146   2.949  -1.534  1.00  0.00           H  
HETATM   60  H32 UNL     1       4.119   2.683  -0.296  1.00  0.00           H  
HETATM   61  H33 UNL     1       3.965   1.792  -1.834  1.00  0.00           H  
HETATM   62  H34 UNL     1       4.634  -1.580  -0.670  1.00  0.00           H  
HETATM   63  H35 UNL     1       3.490  -0.743  -1.869  1.00  0.00           H  
HETATM   64  H36 UNL     1       5.222  -0.427  -1.864  1.00  0.00           H  
HETATM   65  H37 UNL     1       2.686   0.944   1.311  1.00  0.00           H  
HETATM   66  H38 UNL     1       1.646   0.748  -1.573  1.00  0.00           H  
HETATM   67  H39 UNL     1       1.952   2.182  -0.549  1.00  0.00           H  
HETATM   68  H40 UNL     1      -0.313   1.714  -0.168  1.00  0.00           H  
HETATM   69  H41 UNL     1       0.606   1.228   1.265  1.00  0.00           H  
HETATM   70  H42 UNL     1       1.162  -1.225  -1.561  1.00  0.00           H  
HETATM   71  H43 UNL     1      -0.422  -1.978  -1.333  1.00  0.00           H  
HETATM   72  H44 UNL     1      -0.250  -0.275  -2.033  1.00  0.00           H  
CONECT    1    2   29   30   31
CONECT    2    3    4   32
CONECT    3   33   34   35
CONECT    4    5   36   37
CONECT    5    6   38   39
CONECT    6    7   40   41
CONECT    7    8    9   42
CONECT    8   43   44   45
CONECT    9   10   27   46
CONECT   10   11   47   48
CONECT   11   12   49   50
CONECT   12   13   27   51
CONECT   13   14   24   52
CONECT   14   15   53   54
CONECT   15   16   55   56
CONECT   16   17   17   22
CONECT   17   18   57
CONECT   18   19   19   20
CONECT   20   21   58   59
CONECT   21   22   60   61
CONECT   22   23   24
CONECT   23   62   63   64
CONECT   24   25   65
CONECT   25   26   66   67
CONECT   26   27   68   69
CONECT   27   28
CONECT   28   70   71   72
END

HMDB0000921
     RDKit          3D
Cholestenone
 72 75  0  0  0  0  0  0  0  0999 V2000
   -6.9423   -0.0637   -1.1512 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6598    0.9421   -0.0605 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7308    2.3586   -0.5781 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2206    0.6937    0.4175 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2874    0.8798   -0.7366 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8186    0.6691   -0.3660 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5667   -0.7220    0.1519 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.9288   -1.6787   -0.9145 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2580   -0.8438    0.8231 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0085   -2.2441    1.3495 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4661   -2.5536    1.0423 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0188   -1.1672    1.0104 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4245   -1.0215    0.5861 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3132   -1.5117    1.6962 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4626   -0.6575    2.0667 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9618    0.2600    1.0365 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1140    0.8655    1.1991 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6636    1.7889    0.2127 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7146    2.4473    0.4006 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9454    1.9545   -1.0685 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4821    1.8050   -0.8363 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1393    0.4908   -0.1759 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.3778   -0.6110   -1.1864 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7174    0.4139    0.3118 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7112    1.0979   -0.5442 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3782    0.9905    0.2054 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0171   -0.4661    0.1452 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1195   -1.0054   -1.2606 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0392   -0.2834   -1.1866 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6427    0.3674   -2.1465 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3700   -0.9964   -1.0232 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3421    0.7870    0.8180 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7132    2.7815   -0.2758 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6226    2.2963   -1.6881 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9582    3.0148   -0.1286 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2565   -0.3764    0.7793 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9620    1.3343    1.2665 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3719    1.9336   -1.0615 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5949    0.1883   -1.5641 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1795    0.9049   -1.2487 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5973    1.4088    0.4225 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3360   -0.8679    0.9770 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6642   -2.7329   -0.7511 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6443   -1.3305   -1.9453 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0620   -1.6902   -0.9775 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3290   -0.1907    1.7495 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6693   -3.0097    0.9543 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0535   -2.2642    2.4754 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5990   -3.0388    0.0737 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9092   -3.1967    1.8219 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8635   -0.7406    2.0406 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6425   -1.6874   -0.2807 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6891   -2.5536    1.4958 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7163   -1.6550    2.6520 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3403   -1.3354    2.3099 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3083   -0.1240    3.0540 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7367    0.7110    2.0944 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3892    1.2236   -1.7758 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1455    2.9494   -1.5339 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1187    2.6830   -0.2956 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9651    1.7920   -1.8341 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6340   -1.5803   -0.6696 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4900   -0.7427   -1.8692 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224   -0.4273   -1.8639 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6859    0.9437    1.3107 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6464    0.7476   -1.5727 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9522    2.1822   -0.5494 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3129    1.7136   -0.1681 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6060    1.2282    1.2651 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1615   -1.2249   -1.5611 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4218   -1.9785   -1.3333 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2497   -0.2749   -2.0326 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  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  6
 22 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  6
 27  9  1  0
 27 12  1  0
 24 13  1  0
 22 16  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  2 32  1  0
  3 33  1  0
  3 34  1  0
  3 35  1  0
  4 36  1  0
  4 37  1  0
  5 38  1  0
  5 39  1  0
  6 40  1  0
  6 41  1  0
  7 42  1  1
  8 43  1  0
  8 44  1  0
  8 45  1  0
  9 46  1  1
 10 47  1  0
 10 48  1  0
 11 49  1  0
 11 50  1  0
 12 51  1  1
 13 52  1  6
 14 53  1  0
 14 54  1  0
 15 55  1  0
 15 56  1  0
 17 57  1  0
 20 58  1  0
 20 59  1  0
 21 60  1  0
 21 61  1  0
 23 62  1  0
 23 63  1  0
 23 64  1  0
 24 65  1  1
 25 66  1  0
 25 67  1  0
 26 68  1  0
 26 69  1  0
 28 70  1  0
 28 71  1  0
 28 72  1  0
M  END

Synonyms

Value	Source
4-Cholesten-3-one	ChEBI
Cholest-4-en-3-one	HMDB
(17b)-17-Octylandrost-4-en-3-one	HMDB
3-Oxocholest-4-ene	HMDB
D4-Cholesten-3-one	HMDB
D4-Cholestenone	HMDB
(+)-4-Cholesten-3-one	HMDB
(17beta)-17-Octylandrost-4-en-3-one	HMDB
(17Β)-17-octylandrost-4-en-3-one	HMDB
4-Cholestenone	HMDB
Cholesterone	HMDB
delta4-Cholesten-3-one	HMDB
delta4-Cholestenone	HMDB
Δ4-cholesten-3-one	HMDB
Δ4-cholestenone	HMDB

Molecular Formula

C₂₇H₄₄O

Average Mass

384.6377

Monoisotopic Mass

384.33921603

IUPAC Name

(1S,2R,10S,11S,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one

Traditional Name

(1S,2R,10S,11S,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one

CAS Registry Number

Not Available

SMILES

[H][C@@]1(CC[C@@]2([H])[C@]3([H])CCC4=CC(=O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCCC(C)C

InChI Identifier

InChI=1S/C27H44O/c1-18(2)7-6-8-19(3)23-11-12-24-22-10-9-20-17-21(28)13-15-26(20,4)25(22)14-16-27(23,24)5/h17-19,22-25H,6-16H2,1-5H3/t19-,22+,23-,24+,25+,26+,27-/m1/s1

InChI Key

NYOXRYYXRWJDKP-GYKMGIIDSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cholesterols and derivatives. Cholesterols and derivatives are compounds containing a 3-hydroxylated cholestane core.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Cholestane steroids

Direct Parent

Cholesterols and derivatives

Alternative Parents

Substituents

Cholesterol-skeleton
Oxosteroid
3-oxosteroid
3-oxo-delta-4-steroid
Delta-4-steroid
Cyclohexenone
Cyclic ketone
Ketone
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

cholestanoid (CHEBI:16175 )
3-oxo Delta(4)-steroid (CHEBI:16175 )
Cholesterol and derivatives (LMST01010015 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	2.3e-05 g/L	ALOGPS
logP	6.57	ALOGPS
logP	7.68	ChemAxon
logS	-7.2	ALOGPS
pKa (Strongest Acidic)	19.09	ChemAxon
pKa (Strongest Basic)	-4.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	17.07 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	119.57 m³·mol⁻¹	ChemAxon
Polarizability	49.79 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-06di-2229000000-cfc561b8bff8d7587819	2017-09-01	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-001i-0009000000-3ba0c0c4f5b64032e969	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-001j-9803000000-0041fa800c684344d6f8	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-0532-9400000000-d0d60fb4fbca5c06cb01	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-0a4j-7900000000-3ad74b36fc9e3f4b9db4	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-0a4j-7900000000-b5cc0e7902cd6cdf783d	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 60V, Positive	splash10-0a4j-9700000000-d3906eae7c45c97a5b78	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-0a4j-7900000000-1fd5e37ad61a39390fab	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 60V, Positive	splash10-0a4j-9800000000-0f1c723e5ac58579caf8	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 60V, Positive	splash10-0a4j-9700000000-f5034b023ae3ba1d9577	2021-09-20	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0019000000-6f526ead547a001ecc55	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0ap0-3119000000-2a830558981b265c89c0	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0aor-5239000000-c531237dfc518c04a8a7	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-0009000000-fe5ea0c4be8b4b64ece7	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001i-0009000000-5d059b2d1fa5085dd8b7	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0ldi-2019000000-53be05d0d2e2dca6edfd	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-0009000000-4d7a5f3b63c0fb62f1d7	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001i-0009000000-4d7a5f3b63c0fb62f1d7	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-001i-0009000000-79017ac8303e5bbe2a84	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0009000000-200e1637ea1dc1324da1	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-060c-8269000000-6ca50c6965cc22bd1da8	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-052f-9500000000-568f77aab2459f79ab93	2021-09-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl₃, experimental)		2012-12-04	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, CDCl₃, experimental)		2012-12-05	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Blood
Feces
Gall Bladder
Placenta

Tissue Locations

Gall Bladder
Placenta

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species
MMDBp0192197	3-oxo-5-beta-steroid 4-dehydrogenase	Enzyme	P51857	Homo sapiens

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference
MMDBr0024880	Hydrogen Ion	Water	Steroid C26-monooxygenase	Oxygenation	RHEA	34755880
MMDBr0024881	Hydrogen Ion	Water	Steroid C26-monooxygenase	Oxygenation	RHEA	34755880
MMDBr0024886	Cholest-5-en-3-one	Cholestenone	Cholesterol oxidase	Dehydrogenation; Isomerization	RHEA	34755880
MMDBr0024887	Cholest-5-en-3-one	Cholestenone	Cholesterol oxidase	Dehydrogenation; Isomerization	RHEA	34755880
MMDBr0025178	Hydrogen Ion	Water	Steroid C26-monooxygenase	Hydroxylation; Oxygenation	RHEA	34755880
MMDBr0025179	Hydrogen Ion	Water	Steroid C26-monooxygenase	Hydroxylation; Oxygenation	RHEA	34755880
MMDBr0025329	Hydrogen Ion	Water	Steroid C26-monooxygenase	Hydroxylation; Oxygenation	RHEA	34755880
MMDBr0025397	Hydrogen Ion	Water	Steroid C26-monooxygenase	Oxygenation	RHEA	34755880

Health Effects and Bioactivity

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

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Firmicutes	1	Human stool; Human ; Human feces	Indirect association between microbiota composition and metabolites measured in host biospecimen

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Units	Age	Sex	Health Condition	Data Source	Reference
Human Blood	Detected and Quantified	0.079	0.022	uM	Adult (>18 years old)	Both	Normal	HMDB	20671299
Human Gall bladder	Detected but not Quantified				Not Specified	Not Specified	Normal	HMDB	34986597
Human Placenta	Detected but not Quantified				Not Specified	Not Specified	Normal	HMDB	34986597
Human Feces	Detected but not Quantified				Adult (>18 years old)	Both	Normal	HMDB	27543620
Human Feces	Detected but not Quantified				Adult (>18 years old)	Both	Normal	HMDB	25037050
Human Feces	Detected but not Quantified				Adult (>18 years old)	Both	Normal	HMDB	29808030

External Links

HMDB ID

HMDB0000921

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

3898

PubChem Compound

91477

PDB ID

Not Available

ChEBI ID

16175

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Weststrate JA, Ayesh R, Bauer-Plank C, Drewitt PN: Safety evaluation of phytosterol esters. Part 4. Faecal concentrations of bile acids and neutral sterols in healthy normolipidaemic volunteers consuming a controlled diet either with or without a phytosterol ester-enriched margarine. Food Chem Toxicol. 1999 Nov;37(11):1063-71. doi: 10.1016/s0278-6915(99)00102-7. [PubMed:10566877 ]
Maeda Y, Kamimura R, Higashi S, Namba K, Tanaka E, Iwamura T, Setoguchi T: A simple, accurate, and sensitive assay method of dehydroepiandrosterone sulfate: application for quantitative determination in human breast cyst and duct fluids. Steroids. 2002 Apr;67(5):333-8. doi: 10.1016/s0039-128x(01)00186-6. [PubMed:11958788 ]
Nguyen DH, Taub D: Cholesterol is essential for macrophage inflammatory protein 1 beta binding and conformational integrity of CC chemokine receptor 5. Blood. 2002 Jun 15;99(12):4298-306. doi: 10.1182/blood-2001-11-0087. [PubMed:12036855 ]
Norlin M, von Bahr S, Bjorkhem I, Wikvall K: On the substrate specificity of human CYP27A1: implications for bile acid and cholestanol formation. J Lipid Res. 2003 Aug;44(8):1515-22. doi: 10.1194/jlr.M300047-JLR200. Epub 2003 Jun 1. [PubMed:12777473 ]
Nguyen DH, Taub DD: Inhibition of chemokine receptor function by membrane cholesterol oxidation. Exp Cell Res. 2003 Nov 15;291(1):36-45. doi: 10.1016/s0014-4827(03)00345-8. [PubMed:14597406 ]
Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]

Showing metabocard for Cholestenone (MMDBc0000379)

MOL for #<Metabolite:0x00007fa5095d9f70>

3D MOL for #<Metabolite:0x00007fa5095d9f70>

3D SDF for #<Metabolite:0x00007fa5095d9f70>

3D-SDF for #<Metabolite:0x00007fa5095d9f70>

PDB for #<Metabolite:0x00007fa5095d9f70>

3D PDB for #<Metabolite:0x00007fa5095d9f70>

SMILES for #<Metabolite:0x00007fa5095d9f70>

INCHI for #<Metabolite:0x00007fa5095d9f70>

Structure for #<Metabolite:0x00007fa5095d9f70>

3D Structure for #<Metabolite:0x00007fa5095d9f70>