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enzymes (2) Show 2 proteins

Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2021-09-14 15:19:06 UTC

HMDB ID

HMDB0001496

Secondary Accession Numbers

HMDB01496

Metabolite Identification

Common Name

7alpha-Hydroxycholesterol

Description

7alpha-Hydroxycholesterol is an oxysterol and can serve as a biomarker for lipid peroxidation (PMID: 17386651 ). Products of cholesterol oxidation accumulate within atherosclerotic plaque and have been proposed to contribute to inflammatory signalling in the diseased artery (PMID: 17364953 ). 7alpha-Hydroxycholesterol is a cholesterol oxide that has been described as a biomarker of oxidative stress in subjects with impaired glucose tolerance and diabetes (PMID: 16634125 ). 7alpha-Hydroxycholesterol has been identified in the human placenta (PMID: 32033212 ).

Structure

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


  Mrv1652304202022192D          

 33 36  0  0  0  0            999 V2000
 9999.976210001.2192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.8391 9999.9734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.9783 9997.9037    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9995.6978 9997.9037    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.5515 9998.7390    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9999.2638 9999.9734    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9999.9762 9998.7390    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9997.1253 9999.5578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.4108 9999.1453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.4108 9998.3202    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9997.1253 9997.9078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.8398 9998.3202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.8398 9999.1453    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9999.264210000.8031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.549710000.3906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.5497 9999.5655    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9999.2642 9999.1531    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9998.5515 9997.9078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.2660 9998.3202    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9999.978710000.3905    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9999.9787 9999.5656    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10000.7633 9999.3106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.2482 9999.9780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.763310000.6455    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10000.763310001.4705    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10001.479010001.8810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.192610001.4705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.908310001.8810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.624010001.4705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.337610001.8810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.624010000.6455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.049710001.8810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.479010001.0560    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  8  9  1  0  0  0  0
  8 13  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 18 19  1  0  0  0  0
 19  3  1  6  0  0  0
 10  4  1  1  0  0  0
 13  2  1  1  0  0  0
 12 18  2  0  0  0  0
 16  5  1  6  0  0  0
 16 13  1  0  0  0  0
 19 17  1  0  0  0  0
 17  6  1  1  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 24 25  1  0  0  0  0
 24 33  1  6  0  0  0
 25 26  1  0  0  0  0
 25 32  1  6  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  1  0  0  0  0
 24 20  1  0  0  0  0
 24 23  1  0  0  0  0
 17 21  1  0  0  0  0
 21  7  1  6  0  0  0
 14 20  1  0  0  0  0
 20  1  1  1  0  0  0
M  END

HMDB0001496
     RDKit          3D
7alpha-Hydroxycholesterol
 75 78  0  0  0  0  0  0  0  0999 V2000
   -7.6122    0.2220   -1.6619 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5669   -0.3775   -0.2758 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9292    0.5944    0.8019 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2443   -1.0550   -0.0411 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0855   -0.1194   -0.1581 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8080   -0.9173    0.0989 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6014    0.0514   -0.0204 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.9392    1.0812    1.0776 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3347   -0.6373    0.3780 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1248   -1.8730   -0.4735 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0179   -1.4469   -1.4222 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8723   -0.8523   -0.4282 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0868   -0.1413   -0.8658 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0098   -0.8001   -1.8029 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4414   -1.8236   -2.5578 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2989   -1.2833   -1.2491 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8905   -0.6534   -0.2760 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1623   -1.1050    0.2896 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0407    0.0235    0.7236 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.5308    0.6348   -0.4472 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3024    0.9810    1.5881 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8120    0.7592    1.6663 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2334    0.5590    0.2812 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.4567    1.7906   -0.5256 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7969    0.1661    0.4393 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9882    1.0679    1.3158 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6008    0.4998    1.5248 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0744    0.1667    0.2440 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2425    1.3756   -0.5965 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3947   -0.6006   -2.3740 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6496    0.5583   -1.8814 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8913    1.0371   -1.8109 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3558   -1.1811   -0.2652 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5943    0.1655    1.7744 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5488    1.6153    0.6310 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0417    0.6690    0.8297 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1227   -1.8357   -0.8302 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2597   -1.6033    0.9228 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2144    0.7479    0.4750 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0878    0.2610   -1.2220 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7642   -1.6058   -0.7669 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8536   -1.3797    1.0808 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6542    0.4527   -1.0210 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0894    1.2995    1.7317 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7017    0.6382    1.7968 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3079    2.0290    0.6600 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4249   -0.9513    1.4373 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9798   -2.2891   -0.9608 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6516   -2.6476    0.2086 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3799   -0.7739   -2.2072 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3303   -2.4334   -1.8602 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1167   -1.5863    0.3614 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7447    0.8128   -1.3594 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3456   -0.0526   -2.5985 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9389   -1.4067   -3.3012 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7433   -2.1689   -1.6664 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9852   -1.8245    1.1418 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6999   -1.7313   -0.4672 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9305   -0.4108    1.2402 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2195   -0.0103   -0.8017 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5470    2.0363    1.3438 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6864    0.8420    2.6386 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3857    1.7040    2.1103 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6159   -0.0889    2.3369 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1605    1.6962   -1.3515 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8087    2.6581    0.1060 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4456    2.1300   -0.8954 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8290   -0.8291    0.9831 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4741    1.0307    2.3372 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0037    2.1302    1.0371 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1022    1.2246    2.1870 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7067   -0.4465    2.1002 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2075    1.1769   -1.6944 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5677    2.1444   -0.4001 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1552    1.9100   -0.3024 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
 14 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  6
 23 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  6
 28  9  1  0
 28 12  1  0
 25 13  1  0
 23 17  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  2 33  1  0
  3 34  1  0
  3 35  1  0
  3 36  1  0
  4 37  1  0
  4 38  1  0
  5 39  1  0
  5 40  1  0
  6 41  1  0
  6 42  1  0
  7 43  1  6
  8 44  1  0
  8 45  1  0
  8 46  1  0
  9 47  1  1
 10 48  1  0
 10 49  1  0
 11 50  1  0
 11 51  1  0
 12 52  1  1
 13 53  1  6
 14 54  1  6
 15 55  1  0
 16 56  1  0
 18 57  1  0
 18 58  1  0
 19 59  1  1
 20 60  1  0
 21 61  1  0
 21 62  1  0
 22 63  1  0
 22 64  1  0
 24 65  1  0
 24 66  1  0
 24 67  1  0
 25 68  1  1
 26 69  1  0
 26 70  1  0
 27 71  1  0
 27 72  1  0
 29 73  1  0
 29 74  1  0
 29 75  1  0
M  END


  Mrv1652304202022192D          

 33 36  0  0  0  0            999 V2000
 9999.976210001.2192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.8391 9999.9734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.9783 9997.9037    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9995.6978 9997.9037    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.5515 9998.7390    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9999.2638 9999.9734    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9999.9762 9998.7390    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9997.1253 9999.5578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.4108 9999.1453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.4108 9998.3202    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9997.1253 9997.9078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.8398 9998.3202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.8398 9999.1453    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9999.264210000.8031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.549710000.3906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.5497 9999.5655    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9999.2642 9999.1531    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9998.5515 9997.9078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.2660 9998.3202    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9999.978710000.3905    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9999.9787 9999.5656    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10000.7633 9999.3106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.2482 9999.9780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.763310000.6455    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10000.763310001.4705    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10001.479010001.8810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.192610001.4705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.908310001.8810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.624010001.4705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.337610001.8810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.624010000.6455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.049710001.8810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.479010001.0560    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  8  9  1  0  0  0  0
  8 13  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 18 19  1  0  0  0  0
 19  3  1  6  0  0  0
 10  4  1  1  0  0  0
 13  2  1  1  0  0  0
 12 18  2  0  0  0  0
 16  5  1  6  0  0  0
 16 13  1  0  0  0  0
 19 17  1  0  0  0  0
 17  6  1  1  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 24 25  1  0  0  0  0
 24 33  1  6  0  0  0
 25 26  1  0  0  0  0
 25 32  1  6  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  1  0  0  0  0
 24 20  1  0  0  0  0
 24 23  1  0  0  0  0
 17 21  1  0  0  0  0
 21  7  1  6  0  0  0
 14 20  1  0  0  0  0
 20  1  1  1  0  0  0
M  END
> <DATABASE_ID>
HMDB0001496

> <DATABASE_NAME>
hmdb

> <SMILES>
[H][C@@]1(CC[C@@]2([H])[C@]3([H])[C@H](O)C=C4C[C@@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCCC(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C27H46O2/c1-17(2)7-6-8-18(3)21-9-10-22-25-23(12-14-27(21,22)5)26(4)13-11-20(28)15-19(26)16-24(25)29/h16-18,20-25,28-29H,6-15H2,1-5H3/t18-,20+,21-,22+,23+,24-,25+,26+,27-/m1/s1

> <INCHI_KEY>
OYXZMSRRJOYLLO-RVOWOUOISA-N

> <FORMULA>
C27H46O2

> <MOLECULAR_WEIGHT>
402.663

> <EXACT_MASS>
402.349780721

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
75

> <JCHEM_AVERAGE_POLARIZABILITY>
51.28342350245964

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,2R,5S,9S,10S,11S,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-ene-5,9-diol

> <ALOGPS_LOGP>
5.61

> <JCHEM_LOGP>
5.960031693666668

> <ALOGPS_LOGS>
-5.93

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
19.197128213956123

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.204233421519334

> <JCHEM_PKA_STRONGEST_BASIC>
-0.8269276784512555

> <JCHEM_POLAR_SURFACE_AREA>
40.46

> <JCHEM_REFRACTIVITY>
122.05499999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.76e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2R,5S,9S,10S,11S,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-ene-5,9-diol

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0001496
     RDKit          3D
7alpha-Hydroxycholesterol
 75 78  0  0  0  0  0  0  0  0999 V2000
   -7.6122    0.2220   -1.6619 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5669   -0.3775   -0.2758 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9292    0.5944    0.8019 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2443   -1.0550   -0.0411 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0855   -0.1194   -0.1581 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8080   -0.9173    0.0989 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6014    0.0514   -0.0204 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.9392    1.0812    1.0776 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3347   -0.6373    0.3780 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1248   -1.8730   -0.4735 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0179   -1.4469   -1.4222 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8723   -0.8523   -0.4282 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0868   -0.1413   -0.8658 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0098   -0.8001   -1.8029 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4414   -1.8236   -2.5578 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2989   -1.2833   -1.2491 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8905   -0.6534   -0.2760 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1623   -1.1050    0.2896 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0407    0.0235    0.7236 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.5308    0.6348   -0.4472 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3024    0.9810    1.5881 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8120    0.7592    1.6663 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2334    0.5590    0.2812 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.4567    1.7906   -0.5256 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7969    0.1661    0.4393 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9882    1.0679    1.3158 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6008    0.4998    1.5248 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0744    0.1667    0.2440 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2425    1.3756   -0.5965 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3947   -0.6006   -2.3740 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6496    0.5583   -1.8814 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8913    1.0371   -1.8109 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3558   -1.1811   -0.2652 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5943    0.1655    1.7744 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5488    1.6153    0.6310 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0417    0.6690    0.8297 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1227   -1.8357   -0.8302 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2597   -1.6033    0.9228 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2144    0.7479    0.4750 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0878    0.2610   -1.2220 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7642   -1.6058   -0.7669 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8536   -1.3797    1.0808 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6542    0.4527   -1.0210 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0894    1.2995    1.7317 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7017    0.6382    1.7968 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3079    2.0290    0.6600 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4249   -0.9513    1.4373 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9798   -2.2891   -0.9608 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6516   -2.6476    0.2086 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3799   -0.7739   -2.2072 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3303   -2.4334   -1.8602 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1167   -1.5863    0.3614 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7447    0.8128   -1.3594 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3456   -0.0526   -2.5985 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9389   -1.4067   -3.3012 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7433   -2.1689   -1.6664 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9852   -1.8245    1.1418 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6999   -1.7313   -0.4672 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9305   -0.4108    1.2402 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2195   -0.0103   -0.8017 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5470    2.0363    1.3438 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6864    0.8420    2.6386 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3857    1.7040    2.1103 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6159   -0.0889    2.3369 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1605    1.6962   -1.3515 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8087    2.6581    0.1060 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4456    2.1300   -0.8954 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8290   -0.8291    0.9831 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4741    1.0307    2.3372 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0037    2.1302    1.0371 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1022    1.2246    2.1870 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7067   -0.4465    2.1002 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2075    1.1769   -1.6944 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5677    2.1444   -0.4001 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1552    1.9100   -0.3024 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
 14 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  6
 23 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  6
 28  9  1  0
 28 12  1  0
 25 13  1  0
 23 17  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  2 33  1  0
  3 34  1  0
  3 35  1  0
  3 36  1  0
  4 37  1  0
  4 38  1  0
  5 39  1  0
  5 40  1  0
  6 41  1  0
  6 42  1  0
  7 43  1  6
  8 44  1  0
  8 45  1  0
  8 46  1  0
  9 47  1  1
 10 48  1  0
 10 49  1  0
 11 50  1  0
 11 51  1  0
 12 52  1  1
 13 53  1  6
 14 54  1  6
 15 55  1  0
 16 56  1  0
 18 57  1  0
 18 58  1  0
 19 59  1  1
 20 60  1  0
 21 61  1  0
 21 62  1  0
 22 63  1  0
 22 64  1  0
 24 65  1  0
 24 66  1  0
 24 67  1  0
 25 68  1  1
 26 69  1  0
 26 70  1  0
 27 71  1  0
 27 72  1  0
 29 73  1  0
 29 74  1  0
 29 75  1  0
M  END

HEADER    PROTEIN                                 20-APR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-APR-20         0                                  
HETATM    1  C   UNK     0    8666.6228668.943   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8662.6338666.617   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0    8666.6268662.754   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0    8658.6368662.754   0.000  0.00  0.00           O+0
HETATM    5  H   UNK     0    8663.9638664.313   0.000  0.00  0.00           H+0
HETATM    6  H   UNK     0    8665.2928666.617   0.000  0.00  0.00           H+0
HETATM    7  H   UNK     0    8666.6228664.313   0.000  0.00  0.00           H+0
HETATM    8  C   UNK     0    8661.3018665.841   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8659.9678665.071   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8659.9678663.531   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8661.3018662.761   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8662.6348663.531   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8662.6348665.071   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8665.2938668.166   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8663.9598667.396   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8663.9598665.856   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8665.2938665.086   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    8663.9638662.761   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0    8665.2978663.531   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0    8666.6278667.396   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0    8666.6278665.856   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0    8668.0918665.380   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0    8668.9978666.626   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0    8668.0918667.872   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0    8668.0918669.412   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0    8669.4278670.178   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0    8670.7608669.412   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0    8672.0958670.178   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0    8673.4318669.412   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0    8674.7648670.178   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0    8673.4318667.872   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0    8666.7598670.178   0.000  0.00  0.00           C+0
HETATM   33  H   UNK     0    8669.4278668.638   0.000  0.00  0.00           H+0
CONECT    1   20                                                            
CONECT    2   13                                                            
CONECT    3   19                                                            
CONECT    4   10                                                            
CONECT    5   16                                                            
CONECT    6   17                                                            
CONECT    7   21                                                            
CONECT    8    9   13                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11    4                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   18                                                  
CONECT   13    8   12    2   16                                             
CONECT   14   15   20                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17    5   13                                             
CONECT   17   16   19    6   21                                             
CONECT   18   19   12                                                       
CONECT   19   18    3   17                                                  
CONECT   20   21   24   14    1                                             
CONECT   21   20   22   17    7                                             
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   25   33   20   23                                             
CONECT   25   24   26   32                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29                                                            
CONECT   32   25                                                            
CONECT   33   24                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   72    0
END

COMPND    HMDB0001496
HETATM    1  C1  UNL     1      -7.612   0.222  -1.662  1.00  0.00           C  
HETATM    2  C2  UNL     1      -7.567  -0.378  -0.276  1.00  0.00           C  
HETATM    3  C3  UNL     1      -7.929   0.594   0.802  1.00  0.00           C  
HETATM    4  C4  UNL     1      -6.244  -1.055  -0.041  1.00  0.00           C  
HETATM    5  C5  UNL     1      -5.085  -0.119  -0.158  1.00  0.00           C  
HETATM    6  C6  UNL     1      -3.808  -0.917   0.099  1.00  0.00           C  
HETATM    7  C7  UNL     1      -2.601   0.051  -0.020  1.00  0.00           C  
HETATM    8  C8  UNL     1      -2.939   1.081   1.078  1.00  0.00           C  
HETATM    9  C9  UNL     1      -1.335  -0.637   0.378  1.00  0.00           C  
HETATM   10  C10 UNL     1      -1.125  -1.873  -0.473  1.00  0.00           C  
HETATM   11  C11 UNL     1      -0.018  -1.447  -1.422  1.00  0.00           C  
HETATM   12  C12 UNL     1       0.872  -0.852  -0.428  1.00  0.00           C  
HETATM   13  C13 UNL     1       2.087  -0.141  -0.866  1.00  0.00           C  
HETATM   14  C14 UNL     1       3.010  -0.800  -1.803  1.00  0.00           C  
HETATM   15  O1  UNL     1       2.441  -1.824  -2.558  1.00  0.00           O  
HETATM   16  C15 UNL     1       4.299  -1.283  -1.249  1.00  0.00           C  
HETATM   17  C16 UNL     1       4.891  -0.653  -0.276  1.00  0.00           C  
HETATM   18  C17 UNL     1       6.162  -1.105   0.290  1.00  0.00           C  
HETATM   19  C18 UNL     1       7.041   0.024   0.724  1.00  0.00           C  
HETATM   20  O2  UNL     1       7.531   0.635  -0.447  1.00  0.00           O  
HETATM   21  C19 UNL     1       6.302   0.981   1.588  1.00  0.00           C  
HETATM   22  C20 UNL     1       4.812   0.759   1.666  1.00  0.00           C  
HETATM   23  C21 UNL     1       4.233   0.559   0.281  1.00  0.00           C  
HETATM   24  C22 UNL     1       4.457   1.791  -0.526  1.00  0.00           C  
HETATM   25  C23 UNL     1       2.797   0.166   0.439  1.00  0.00           C  
HETATM   26  C24 UNL     1       1.988   1.068   1.316  1.00  0.00           C  
HETATM   27  C25 UNL     1       0.601   0.500   1.525  1.00  0.00           C  
HETATM   28  C26 UNL     1      -0.074   0.167   0.244  1.00  0.00           C  
HETATM   29  C27 UNL     1      -0.243   1.376  -0.596  1.00  0.00           C  
HETATM   30  H1  UNL     1      -7.395  -0.601  -2.374  1.00  0.00           H  
HETATM   31  H2  UNL     1      -8.650   0.558  -1.881  1.00  0.00           H  
HETATM   32  H3  UNL     1      -6.891   1.037  -1.811  1.00  0.00           H  
HETATM   33  H4  UNL     1      -8.356  -1.181  -0.265  1.00  0.00           H  
HETATM   34  H5  UNL     1      -7.594   0.165   1.774  1.00  0.00           H  
HETATM   35  H6  UNL     1      -7.549   1.615   0.631  1.00  0.00           H  
HETATM   36  H7  UNL     1      -9.042   0.669   0.830  1.00  0.00           H  
HETATM   37  H8  UNL     1      -6.123  -1.836  -0.830  1.00  0.00           H  
HETATM   38  H9  UNL     1      -6.260  -1.603   0.923  1.00  0.00           H  
HETATM   39  H10 UNL     1      -5.214   0.748   0.475  1.00  0.00           H  
HETATM   40  H11 UNL     1      -5.088   0.261  -1.222  1.00  0.00           H  
HETATM   41  H12 UNL     1      -3.764  -1.606  -0.767  1.00  0.00           H  
HETATM   42  H13 UNL     1      -3.854  -1.380   1.081  1.00  0.00           H  
HETATM   43  H14 UNL     1      -2.654   0.453  -1.021  1.00  0.00           H  
HETATM   44  H15 UNL     1      -2.089   1.299   1.732  1.00  0.00           H  
HETATM   45  H16 UNL     1      -3.702   0.638   1.797  1.00  0.00           H  
HETATM   46  H17 UNL     1      -3.308   2.029   0.660  1.00  0.00           H  
HETATM   47  H18 UNL     1      -1.425  -0.951   1.437  1.00  0.00           H  
HETATM   48  H19 UNL     1      -1.980  -2.289  -0.961  1.00  0.00           H  
HETATM   49  H20 UNL     1      -0.652  -2.648   0.209  1.00  0.00           H  
HETATM   50  H21 UNL     1      -0.380  -0.774  -2.207  1.00  0.00           H  
HETATM   51  H22 UNL     1       0.330  -2.433  -1.860  1.00  0.00           H  
HETATM   52  H23 UNL     1       1.117  -1.586   0.361  1.00  0.00           H  
HETATM   53  H24 UNL     1       1.745   0.813  -1.359  1.00  0.00           H  
HETATM   54  H25 UNL     1       3.346  -0.053  -2.599  1.00  0.00           H  
HETATM   55  H26 UNL     1       1.939  -1.407  -3.301  1.00  0.00           H  
HETATM   56  H27 UNL     1       4.743  -2.169  -1.666  1.00  0.00           H  
HETATM   57  H28 UNL     1       5.985  -1.825   1.142  1.00  0.00           H  
HETATM   58  H29 UNL     1       6.700  -1.731  -0.467  1.00  0.00           H  
HETATM   59  H30 UNL     1       7.930  -0.411   1.240  1.00  0.00           H  
HETATM   60  H31 UNL     1       8.219  -0.010  -0.802  1.00  0.00           H  
HETATM   61  H32 UNL     1       6.547   2.036   1.344  1.00  0.00           H  
HETATM   62  H33 UNL     1       6.686   0.842   2.639  1.00  0.00           H  
HETATM   63  H34 UNL     1       4.386   1.704   2.110  1.00  0.00           H  
HETATM   64  H35 UNL     1       4.616  -0.089   2.337  1.00  0.00           H  
HETATM   65  H36 UNL     1       5.161   1.696  -1.351  1.00  0.00           H  
HETATM   66  H37 UNL     1       4.809   2.658   0.106  1.00  0.00           H  
HETATM   67  H38 UNL     1       3.446   2.130  -0.895  1.00  0.00           H  
HETATM   68  H39 UNL     1       2.829  -0.829   0.983  1.00  0.00           H  
HETATM   69  H40 UNL     1       2.474   1.031   2.337  1.00  0.00           H  
HETATM   70  H41 UNL     1       2.004   2.130   1.037  1.00  0.00           H  
HETATM   71  H42 UNL     1       0.102   1.225   2.187  1.00  0.00           H  
HETATM   72  H43 UNL     1       0.707  -0.446   2.100  1.00  0.00           H  
HETATM   73  H44 UNL     1      -0.207   1.177  -1.694  1.00  0.00           H  
HETATM   74  H45 UNL     1       0.568   2.144  -0.400  1.00  0.00           H  
HETATM   75  H46 UNL     1      -1.155   1.910  -0.302  1.00  0.00           H  
CONECT    1    2   30   31   32
CONECT    2    3    4   33
CONECT    3   34   35   36
CONECT    4    5   37   38
CONECT    5    6   39   40
CONECT    6    7   41   42
CONECT    7    8    9   43
CONECT    8   44   45   46
CONECT    9   10   28   47
CONECT   10   11   48   49
CONECT   11   12   50   51
CONECT   12   13   28   52
CONECT   13   14   25   53
CONECT   14   15   16   54
CONECT   15   55
CONECT   16   17   17   56
CONECT   17   18   23
CONECT   18   19   57   58
CONECT   19   20   21   59
CONECT   20   60
CONECT   21   22   61   62
CONECT   22   23   63   64
CONECT   23   24   25
CONECT   24   65   66   67
CONECT   25   26   68
CONECT   26   27   69   70
CONECT   27   28   71   72
CONECT   28   29
CONECT   29   73   74   75
END

HMDB0001496
     RDKit          3D
7alpha-Hydroxycholesterol
 75 78  0  0  0  0  0  0  0  0999 V2000
   -7.6122    0.2220   -1.6619 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5669   -0.3775   -0.2758 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9292    0.5944    0.8019 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2443   -1.0550   -0.0411 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0855   -0.1194   -0.1581 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8080   -0.9173    0.0989 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6014    0.0514   -0.0204 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.9392    1.0812    1.0776 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3347   -0.6373    0.3780 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1248   -1.8730   -0.4735 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0179   -1.4469   -1.4222 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8723   -0.8523   -0.4282 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0868   -0.1413   -0.8658 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0098   -0.8001   -1.8029 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4414   -1.8236   -2.5578 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2989   -1.2833   -1.2491 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8905   -0.6534   -0.2760 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1623   -1.1050    0.2896 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0407    0.0235    0.7236 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.5308    0.6348   -0.4472 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3024    0.9810    1.5881 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8120    0.7592    1.6663 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2334    0.5590    0.2812 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.4567    1.7906   -0.5256 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7969    0.1661    0.4393 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9882    1.0679    1.3158 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6008    0.4998    1.5248 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0744    0.1667    0.2440 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2425    1.3756   -0.5965 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3947   -0.6006   -2.3740 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6496    0.5583   -1.8814 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8913    1.0371   -1.8109 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3558   -1.1811   -0.2652 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5943    0.1655    1.7744 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5488    1.6153    0.6310 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0417    0.6690    0.8297 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1227   -1.8357   -0.8302 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2597   -1.6033    0.9228 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2144    0.7479    0.4750 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0878    0.2610   -1.2220 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7642   -1.6058   -0.7669 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8536   -1.3797    1.0808 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6542    0.4527   -1.0210 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0894    1.2995    1.7317 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7017    0.6382    1.7968 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3079    2.0290    0.6600 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4249   -0.9513    1.4373 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9798   -2.2891   -0.9608 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6516   -2.6476    0.2086 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3799   -0.7739   -2.2072 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3303   -2.4334   -1.8602 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1167   -1.5863    0.3614 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7447    0.8128   -1.3594 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3456   -0.0526   -2.5985 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9389   -1.4067   -3.3012 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7433   -2.1689   -1.6664 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9852   -1.8245    1.1418 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6999   -1.7313   -0.4672 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9305   -0.4108    1.2402 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2195   -0.0103   -0.8017 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5470    2.0363    1.3438 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6864    0.8420    2.6386 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3857    1.7040    2.1103 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6159   -0.0889    2.3369 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1605    1.6962   -1.3515 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8087    2.6581    0.1060 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4456    2.1300   -0.8954 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8290   -0.8291    0.9831 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4741    1.0307    2.3372 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0037    2.1302    1.0371 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1022    1.2246    2.1870 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7067   -0.4465    2.1002 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2075    1.1769   -1.6944 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5677    2.1444   -0.4001 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1552    1.9100   -0.3024 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
 14 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  6
 23 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  6
 28  9  1  0
 28 12  1  0
 25 13  1  0
 23 17  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  2 33  1  0
  3 34  1  0
  3 35  1  0
  3 36  1  0
  4 37  1  0
  4 38  1  0
  5 39  1  0
  5 40  1  0
  6 41  1  0
  6 42  1  0
  7 43  1  6
  8 44  1  0
  8 45  1  0
  8 46  1  0
  9 47  1  1
 10 48  1  0
 10 49  1  0
 11 50  1  0
 11 51  1  0
 12 52  1  1
 13 53  1  6
 14 54  1  6
 15 55  1  0
 16 56  1  0
 18 57  1  0
 18 58  1  0
 19 59  1  1
 20 60  1  0
 21 61  1  0
 21 62  1  0
 22 63  1  0
 22 64  1  0
 24 65  1  0
 24 66  1  0
 24 67  1  0
 25 68  1  1
 26 69  1  0
 26 70  1  0
 27 71  1  0
 27 72  1  0
 29 73  1  0
 29 74  1  0
 29 75  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
7alpha-Hydroxy-cholesterol	ChEBI
Cholest-5-ene-3beta,7alpha-diol	ChEBI
7a-Hydroxy-cholesterol	Generator
7Α-hydroxy-cholesterol	Generator
Cholest-5-ene-3b,7a-diol	Generator
Cholest-5-ene-3β,7α-diol	Generator
7a-Hydroxycholesterol	Generator
7Α-hydroxycholesterol	Generator
7 alpha-Hydroxycholesterol	HMDB
Cholest-5-en-3 beta,7 alpha-diol	HMDB
(3beta,7alpha)-Cholest-5-ene-3,7-diol	HMDB
(3Β,7α)-cholest-5-ene-3,7-diol	HMDB
7alpha-Hydroxycholest-5-en-3beta-ol	HMDB
7AlphaOHChol	HMDB
7Α-hydroxycholest-5-en-3β-ol	HMDB
7ΑOHChol	HMDB
7alpha-Hydroxycholesterol	HMDB

Chemical Formula

C₂₇H₄₆O₂

Average Molecular Weight

402.663

Monoisotopic Molecular Weight

402.349780721

IUPAC Name

(1S,2R,5S,9S,10S,11S,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-ene-5,9-diol

Traditional Name

(1S,2R,5S,9S,10S,11S,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-ene-5,9-diol

CAS Registry Number

566-26-7

SMILES

[H][C@@]1(CC[C@@]2([H])[C@]3([H])[C@H](O)C=C4C[C@@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCCC(C)C

InChI Identifier

InChI=1S/C27H46O2/c1-17(2)7-6-8-18(3)21-9-10-22-25-23(12-14-27(21,22)5)26(4)13-11-20(28)15-19(26)16-24(25)29/h16-18,20-25,28-29H,6-15H2,1-5H3/t18-,20+,21-,22+,23+,24-,25+,26+,27-/m1/s1

InChI Key

OYXZMSRRJOYLLO-RVOWOUOISA-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
Cholesterol-skeleton
3-hydroxy-delta-5-steroid
3-hydroxysteroid
Hydroxysteroid
3-beta-hydroxy-delta-5-steroid
3-beta-hydroxysteroid
7-hydroxysteroid
Delta-5-steroid
Cyclic alcohol
Secondary alcohol
Alcohol
Organooxygen compound
Organic oxygen compound
Hydrocarbon derivative
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

7alpha-hydroxy steroid (CHEBI:17500 )
oxysterol (CHEBI:17500 )
Cholesterol and derivatives (C03594 )
Cholesterol and derivatives (LMST01010013 )

Ontology

Physiological effect

Adverse health effect

Digestive system disorder

Hepatobiliary disorder

Hepatic disorder

Cirrhosis - Reduced in human blood (PMID: 8558093 ).

Disposition

Biological location

Excreta

Feces

Cellular substructure

Macromolecular complex

Blood

Organelle

Endoplasmic reticulum

Extracellular

Organ

Placenta

Ingestion

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Bile acid biosynthesis

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 Spectral Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.00048 g/L	ALOGPS
logP	10^(5.61) g/L	ALOGPS
logP	10^(5.96) g/L	ChemAxon
logS	10^(-5.9) g/L	ALOGPS
pKa (Strongest Acidic)	18.2	ChemAxon
pKa (Strongest Basic)	-0.83	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	40.46 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	122.06 m³·mol⁻¹	ChemAxon
Polarizability	51.28 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Spectral Properties

Predicted Kovats Retention Indices

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
7alpha-Hydroxycholesterol,1TMS,#1	CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3[C@H](O[Si](C)(C)C)C=C4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@@]21C	3264.1	Semi standard non polar	https://arxiv.org/abs/1905.12712
7alpha-Hydroxycholesterol,1TMS,#2	CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3[C@H](O)C=C4C[C@@H](O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C	3259.5	Semi standard non polar	https://arxiv.org/abs/1905.12712
7alpha-Hydroxycholesterol,2TMS,#1	CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3[C@H](O[Si](C)(C)C)C=C4C[C@@H](O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C	3176.3	Semi standard non polar	https://arxiv.org/abs/1905.12712
7alpha-Hydroxycholesterol,1TBDMS,#1	CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3[C@H](O[Si](C)(C)C(C)(C)C)C=C4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@@]21C	3511.3	Semi standard non polar	https://arxiv.org/abs/1905.12712
7alpha-Hydroxycholesterol,1TBDMS,#2	CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3[C@H](O)C=C4C[C@@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C	3486.1	Semi standard non polar	https://arxiv.org/abs/1905.12712
7alpha-Hydroxycholesterol,2TBDMS,#1	CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3[C@H](O[Si](C)(C)C(C)(C)C)C=C4C[C@@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C	3668.2	Semi standard non polar	https://arxiv.org/abs/1905.12712

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 7alpha-Hydroxycholesterol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - 7alpha-Hydroxycholesterol 35V, Positive-QTOF	splash10-0udi-2000900000-11d8f3e5ae551e34bf88	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7alpha-Hydroxycholesterol 10V, Negative-QTOF	splash10-0udi-0000900000-079f76b4d985e4b92c9d	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7alpha-Hydroxycholesterol 20V, Negative-QTOF	splash10-0udi-0000900000-079f76b4d985e4b92c9d	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7alpha-Hydroxycholesterol 40V, Negative-QTOF	splash10-0002-0009100000-71906a2df9357f22bb56	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7alpha-Hydroxycholesterol 10V, Positive-QTOF	splash10-0udi-1003900000-28bc1d0c38885b76f102	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7alpha-Hydroxycholesterol 20V, Positive-QTOF	splash10-0l6r-9134200000-b6e1e10244022e0b9cce	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7alpha-Hydroxycholesterol 40V, Positive-QTOF	splash10-0a4i-9740000000-f4f3165be03261bd2bd9	2021-09-22	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane (predicted from logP)
Endoplasmic reticulum

Biospecimen Locations

Blood
Cerebrospinal Fluid (CSF)
Feces

Tissue Locations

Placenta

Pathways

Name	SMPDB/PathBank	KEGG
Primary bile acid biosynthesis	Not Available
Congenital Bile Acid Synthesis Defect Type II		Not Available
Congenital Bile Acid Synthesis Defect Type III		Not Available
Familial Hypercholanemia (FHCA)		Not Available
Zellweger Syndrome		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.18 +/- 0.047 uM	Adult (>18 years old)	Both	Normal	8558093	details
Blood	Detected and Quantified	0.335 +/- 0.068 uM	Adult (>18 years old)	Both	Normal	20671299	details
Blood	Detected and Quantified	0.012 +/- 0.002 uM	Adult (>18 years old)	Both	Normal	20671299	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.004 +/- 0.0016 uM	Adult (>18 years old)	Not Specified	Normal	15576852	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	25037050	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.054 +/- 0.019 uM	Adult (>18 years old)	Both	Cirrhosis	8558093	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.005 +/- 0.0021 uM	Adult (>18 years old)	Not Specified	Multiple Sclerosis	15576852	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal Cancer	27275383	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	25037050	details

Associated Disorders and Diseases

Disease References

Cirrhosis
Hahn C, Reichel C, von Bergmann K: Serum concentration of 7 alpha-hydroxycholesterol as an indicator of bile acid synthesis in humans. J Lipid Res. 1995 Sep;36(9):2059-66. [PubMed:8558093 ]
Multiple sclerosis
Leoni V, Lutjohann D, Masterman T: Levels of 7-oxocholesterol in cerebrospinal fluid are more than one thousand times lower than reported in multiple sclerosis. J Lipid Res. 2005 Feb;46(2):191-5. Epub 2004 Dec 1. [PubMed:15576852 ]
Colorectal cancer
Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ] Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]

Associated OMIM IDs

126200 (Multiple sclerosis)
114500 (Colorectal cancer)

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022655

KNApSAcK ID

Not Available

Chemspider ID

96891

KEGG Compound ID

C03594

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

7α-Hydroxycholesterol

METLIN ID

Not Available

PubChem Compound

107722

PDB ID

Not Available

ChEBI ID

17500

Food Biomarker Ontology

Not Available

VMH ID

XOL7A

MarkerDB ID

MDB00000333

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Kitano S, Yoshida Y, Kawano K, Hibi N, Niki E: Oxidative status of human low density lipoprotein isolated by anion-exchange high-performance liquid chromatography--assessment by total hydroxyoctadecadienoic acid, 7-hydroxycholesterol, and 8-iso-prostaglandin F(2alpha). Anal Chim Acta. 2007 Feb 28;585(1):86-93. Epub 2006 Dec 23. [PubMed:17386651 ]
Erridge C, Webb DJ, Spickett CM: 25-Hydroxycholesterol, 7beta-hydroxycholesterol and 7-ketocholesterol upregulate interleukin-8 expression independently of Toll-like receptor 1, 2, 4 or 6 signalling in human macrophages. Free Radic Res. 2007 Mar;41(3):260-6. [PubMed:17364953 ]
Ferderbar S, Pereira EC, Apolinario E, Bertolami MC, Faludi A, Monte O, Calliari LE, Sales JE, Gagliardi AR, Xavier HT, Abdalla DS: Cholesterol oxides as biomarkers of oxidative stress in type 1 and type 2 diabetes mellitus. Diabetes Metab Res Rev. 2007 Jan;23(1):35-42. [PubMed:16634125 ]
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 ]

Enzymes

Enzyme Details

1. Cholesterol 7-alpha-monooxygenase

General function:: Involved in monooxygenase activity
Specific function:: Catalyzes a rate-limiting step in cholesterol catabolism and bile acid biosynthesis by introducing a hydrophilic moiety at position 7 of cholesterol. Important for cholesterol homeostasis.
Gene Name:: CYP7A1
Uniprot ID:: P22680
Molecular weight:: 57660.155

Reactions

Cholesterol + NADPH + Oxygen → 7alpha-Hydroxycholesterol + NADP + Water	details
Cholesterol + Oxygen + NADPH + Hydrogen Ion → 7alpha-Hydroxycholesterol + NADP + Water	details

Enzyme Details

2. 3 beta-hydroxysteroid dehydrogenase type 7

General function:: Involved in 3-beta-hydroxy-delta5-steroid dehydrogenase activity
Specific function:: The 3-beta-HSD enzymatic system plays a crucial role in the biosynthesis of all classes of hormonal steroids. HSD VII is active against four 7-alpha-hydroxylated sterols. Does not metabolize several different C(19/21) steroids as substrates. Involved in bile acid synthesis.
Gene Name:: HSD3B7
Uniprot ID:: Q9H2F3
Molecular weight:: 21322.265

Reactions

7alpha-Hydroxycholesterol + NAD → 7a-Hydroxy-cholestene-3-one + NADH + Hydrogen Ion	details

Showing metabocard for 7alpha-Hydroxycholesterol (HMDB0001496)

MOL for HMDB0001496 (7alpha-Hydroxycholesterol)

3D MOL for HMDB0001496 (7alpha-Hydroxycholesterol)

3D SDF for HMDB0001496 (7alpha-Hydroxycholesterol)

3D-SDF for HMDB0001496 (7alpha-Hydroxycholesterol)

PDB for HMDB0001496 (7alpha-Hydroxycholesterol)

3D PDB for HMDB0001496 (7alpha-Hydroxycholesterol)

SMILES for HMDB0001496 (7alpha-Hydroxycholesterol)

INCHI for HMDB0001496 (7alpha-Hydroxycholesterol)

Structure for HMDB0001496 (7alpha-Hydroxycholesterol)

3D Structure for HMDB0001496 (7alpha-Hydroxycholesterol)

Predicted Kovats Retention Indices

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

Reactions

Reactions