Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (1) Show 1 protein XML

Show more...Show more...Show more...Show more...

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2006-08-13 09:27:14 UTC

Update Date

2022-03-07 02:49:20 UTC

HMDB ID

HMDB0004035

Secondary Accession Numbers

HMDB04035

Metabolite Identification

Common Name

22b-Hydroxycholesterol

Description

22b-Hydroxycholesterol, also known as cholest-5-en-3b,22R-diol or 22(R)OH cholesterol, belongs to the class of organic compounds known as dihydroxy bile acids, alcohols and derivatives. Dihydroxy bile acids, alcohols and derivatives are compounds containing or derived from a bile acid or alcohol, and which bears exactly two carboxylic acid groups. Thus, 22b-hydroxycholesterol is considered to be a sterol lipid molecule. 22b-Hydroxycholesterol is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.

Structure

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

HMDB04035.mol
  Mrv0541 02231219512D          

 32 35  0  0  0  0            999 V2000
   -3.3626   -1.8009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3626   -2.6259    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.6482   -3.0384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9337   -2.6259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9337   -1.8009    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.6482   -1.3884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2192   -3.0384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5047   -2.6259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5047   -1.8009    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2192   -1.3884    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2097   -1.3884    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2097   -0.5634    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5047   -0.1509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2192   -0.5634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9944   -1.6433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4793   -0.9759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9944   -0.3084    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2960    0.2571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2493    0.4762    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5047   -0.9759    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9337   -0.9759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0771   -3.0384    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2097   -2.2134    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2192   -2.2134    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6659    1.0595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0563    0.6477    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2698    1.4446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0667    1.6581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2802    2.4550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6968    3.0384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0771    2.6685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6396    0.0643    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  1  1  0  0  0  0
  4  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10  5  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 10  1  0  0  0  0
 11 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 12  1  0  0  0  0
 12 18  1  1  0  0  0
 17 19  1  1  0  0  0
  9 20  1  1  0  0  0
  5 21  1  1  0  0  0
  2 22  1  1  0  0  0
 11 23  1  6  0  0  0
 10 24  1  6  0  0  0
 19 25  1  6  0  0  0
 19 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
 29 30  1  0  0  0  0
 29 31  1  0  0  0  0
 26 32  1  1  0  0  0
M  END

HMDB0004035
     RDKit          3D
22b-Hydroxycholesterol
 75 78  0  0  0  0  0  0  0  0999 V2000
    6.4698    2.1643   -1.8337 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9901    0.8651   -1.2272 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0444   -0.2221   -1.3132 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6854    1.1800    0.2530 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1973   -0.0214    0.9691 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9384   -0.6709    0.5168 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.8854   -1.8353    1.3969 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6705    0.1108    0.8049 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6378    1.4421    0.1742 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4568   -0.7184    0.5574 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3819   -1.9373    1.4530 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1024   -2.1384    1.7779 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7489   -1.3921    0.7125 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1417   -0.9073    0.9321 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0501   -1.8531    1.5995 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4416   -1.6803    1.1223 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8716   -0.8495    0.2067 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3176   -0.8285   -0.1318 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7627    0.3599   -0.9073 C   0  0  1  0  0  0  0  0  0  0  0  0
   -7.1999    1.4031   -0.0623 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8275    0.8395   -1.9588 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4544    0.1705   -1.9161 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9170    0.0846   -0.5222 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.8986    1.3862    0.2012 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6240   -0.6730   -0.5140 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5328   -0.1801   -1.3700 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3768    0.5049   -0.6989 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1203   -0.1230    0.5704 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1630    0.7987    1.7205 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8462    2.8361   -1.0619 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6207    2.6448   -2.3987 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2212    1.9141   -2.6114 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0490    0.4956   -1.6617 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5036   -1.1914   -1.2576 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5406   -0.1541   -2.3072 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7680   -0.1747   -0.4795 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7367    1.3686    0.6830 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1110    2.0847    0.2587 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0649   -0.7621    0.9115 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1776    0.1562    2.1025 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0339   -0.9902   -0.5272 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6444   -2.3803    1.0390 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7675    0.3334    1.9318 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9821    2.2717    0.8571 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0960    1.4621   -0.8206 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5735    1.8067   -0.0280 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5748   -1.1708   -0.4819 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9002   -1.8245    2.4235 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7421   -2.8640    0.9851 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3671   -3.2328    1.6646 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3503   -1.8917    2.8207 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6308   -1.9441   -0.2441 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2209    0.0840    1.4319 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7241   -2.9162    1.5664 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0878   -1.5660    2.6965 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2237   -2.3194    1.5815 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9038   -0.8888    0.8141 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6080   -1.7569   -0.7058 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7172    0.0470   -1.4377 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2389    2.2142   -0.6503 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6922    1.9565   -1.9880 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2069    0.6009   -2.9976 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5861   -0.8713   -2.2858 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8348    0.7020   -2.6351 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2848    1.2903    1.2353 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9028    1.8511    0.2815 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5903    2.1340   -0.2951 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8938   -1.7164   -0.8640 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0799   -1.0205   -1.9818 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8621    0.5347   -2.1825 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4232    0.5263   -1.4972 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6805    1.5576   -0.5574 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7350    1.3066    2.1301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8543    1.6010    1.4206 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6190    0.2958    2.6091 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
  6  8  1  0
  8  9  1  0
  8 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  1  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  1
 23 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  1
 28 10  1  0
 28 13  1  0
 25 14  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  6
  7 42  1  0
  8 43  1  1
  9 44  1  0
  9 45  1  0
  9 46  1  0
 10 47  1  6
 11 48  1  0
 11 49  1  0
 12 50  1  0
 12 51  1  0
 13 52  1  6
 14 53  1  1
 15 54  1  0
 15 55  1  0
 16 56  1  0
 18 57  1  0
 18 58  1  0
 19 59  1  6
 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  6
 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

HMDB04035.mol
  Mrv0541 02231219512D          

 32 35  0  0  0  0            999 V2000
   -3.3626   -1.8009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3626   -2.6259    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.6482   -3.0384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9337   -2.6259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9337   -1.8009    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.6482   -1.3884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2192   -3.0384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5047   -2.6259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5047   -1.8009    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2192   -1.3884    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2097   -1.3884    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2097   -0.5634    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5047   -0.1509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2192   -0.5634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9944   -1.6433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4793   -0.9759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9944   -0.3084    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2960    0.2571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2493    0.4762    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5047   -0.9759    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9337   -0.9759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0771   -3.0384    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2097   -2.2134    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2192   -2.2134    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6659    1.0595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0563    0.6477    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2698    1.4446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0667    1.6581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2802    2.4550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6968    3.0384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0771    2.6685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6396    0.0643    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  1  1  0  0  0  0
  4  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10  5  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 10  1  0  0  0  0
 11 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 12  1  0  0  0  0
 12 18  1  1  0  0  0
 17 19  1  1  0  0  0
  9 20  1  1  0  0  0
  5 21  1  1  0  0  0
  2 22  1  1  0  0  0
 11 23  1  6  0  0  0
 10 24  1  6  0  0  0
 19 25  1  6  0  0  0
 19 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
 29 30  1  0  0  0  0
 29 31  1  0  0  0  0
 26 32  1  1  0  0  0
M  END
> <DATABASE_ID>
HMDB0004035

> <DATABASE_NAME>
hmdb

> <SMILES>
[H][C@@]12CC[C@H]([C@H](C)[C@H](O)CCC(C)C)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC=C2C[C@@H](O)CC[C@]12C

> <INCHI_IDENTIFIER>
InChI=1S/C27H46O2/c1-17(2)6-11-25(29)18(3)22-9-10-23-21-8-7-19-16-20(28)12-14-26(19,4)24(21)13-15-27(22,23)5/h7,17-18,20-25,28-29H,6,8-16H2,1-5H3/t18-,20-,21-,22+,23-,24-,25+,26-,27+/m0/s1

> <INCHI_KEY>
RZPAXNJLEKLXNO-GFKLAVDKSA-N

> <FORMULA>
C27H46O2

> <MOLECULAR_WEIGHT>
402.6529

> <EXACT_MASS>
402.349780716

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
50.76953840343177

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,2R,5S,10S,11S,14R,15S)-14-[(2S,3R)-3-hydroxy-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-5-ol

> <ALOGPS_LOGP>
5.69

> <JCHEM_LOGP>
5.804124233666668

> <ALOGPS_LOGS>
-5.79

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
19.477856532809838

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.20428950550382

> <JCHEM_PKA_STRONGEST_BASIC>
-0.7338943961064351

> <JCHEM_POLAR_SURFACE_AREA>
40.46

> <JCHEM_REFRACTIVITY>
122.20899999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
6.53e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
22R-hydroxycholesterol

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0004035
     RDKit          3D
22b-Hydroxycholesterol
 75 78  0  0  0  0  0  0  0  0999 V2000
    6.4698    2.1643   -1.8337 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9901    0.8651   -1.2272 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0444   -0.2221   -1.3132 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6854    1.1800    0.2530 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1973   -0.0214    0.9691 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9384   -0.6709    0.5168 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.8854   -1.8353    1.3969 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6705    0.1108    0.8049 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6378    1.4421    0.1742 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4568   -0.7184    0.5574 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3819   -1.9373    1.4530 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1024   -2.1384    1.7779 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7489   -1.3921    0.7125 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1417   -0.9073    0.9321 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0501   -1.8531    1.5995 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4416   -1.6803    1.1223 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8716   -0.8495    0.2067 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3176   -0.8285   -0.1318 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7627    0.3599   -0.9073 C   0  0  1  0  0  0  0  0  0  0  0  0
   -7.1999    1.4031   -0.0623 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8275    0.8395   -1.9588 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4544    0.1705   -1.9161 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9170    0.0846   -0.5222 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.8986    1.3862    0.2012 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6240   -0.6730   -0.5140 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5328   -0.1801   -1.3700 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3768    0.5049   -0.6989 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1203   -0.1230    0.5704 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1630    0.7987    1.7205 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8462    2.8361   -1.0619 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6207    2.6448   -2.3987 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2212    1.9141   -2.6114 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0490    0.4956   -1.6617 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5036   -1.1914   -1.2576 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5406   -0.1541   -2.3072 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7680   -0.1747   -0.4795 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7367    1.3686    0.6830 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1110    2.0847    0.2587 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0649   -0.7621    0.9115 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1776    0.1562    2.1025 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0339   -0.9902   -0.5272 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6444   -2.3803    1.0390 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7675    0.3334    1.9318 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9821    2.2717    0.8571 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0960    1.4621   -0.8206 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5735    1.8067   -0.0280 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5748   -1.1708   -0.4819 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9002   -1.8245    2.4235 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7421   -2.8640    0.9851 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3671   -3.2328    1.6646 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3503   -1.8917    2.8207 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6308   -1.9441   -0.2441 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2209    0.0840    1.4319 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7241   -2.9162    1.5664 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0878   -1.5660    2.6965 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2237   -2.3194    1.5815 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9038   -0.8888    0.8141 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6080   -1.7569   -0.7058 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7172    0.0470   -1.4377 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2389    2.2142   -0.6503 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6922    1.9565   -1.9880 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2069    0.6009   -2.9976 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5861   -0.8713   -2.2858 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8348    0.7020   -2.6351 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2848    1.2903    1.2353 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9028    1.8511    0.2815 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5903    2.1340   -0.2951 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8938   -1.7164   -0.8640 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0799   -1.0205   -1.9818 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8621    0.5347   -2.1825 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4232    0.5263   -1.4972 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6805    1.5576   -0.5574 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7350    1.3066    2.1301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8543    1.6010    1.4206 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6190    0.2958    2.6091 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
  6  8  1  0
  8  9  1  0
  8 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  1  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  1
 23 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  1
 28 10  1  0
 28 13  1  0
 25 14  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  6
  7 42  1  0
  8 43  1  1
  9 44  1  0
  9 45  1  0
  9 46  1  0
 10 47  1  6
 11 48  1  0
 11 49  1  0
 12 50  1  0
 12 51  1  0
 13 52  1  6
 14 53  1  1
 15 54  1  0
 15 55  1  0
 16 56  1  0
 18 57  1  0
 18 58  1  0
 19 59  1  6
 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  6
 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                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: HMDB04035.mol                                     
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  C   UNK     0      -6.277  -3.362   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -6.277  -4.902   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.943  -5.672   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -3.610  -4.902   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -3.610  -3.362   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -4.943  -2.592   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.276  -5.672   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.942  -4.902   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.942  -3.362   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.276  -2.592   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.391  -2.592   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.391  -1.052   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.942  -0.282   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.276  -1.052   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.856  -3.067   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.761  -1.822   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.856  -0.576   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.553   0.480   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.332   0.889   0.000  0.00  0.00           C+0
HETATM   20  H   UNK     0      -0.942  -1.822   0.000  0.00  0.00           H+0
HETATM   21  C   UNK     0      -3.610  -1.822   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -7.611  -5.672   0.000  0.00  0.00           O+0
HETATM   23  H   UNK     0       0.391  -4.132   0.000  0.00  0.00           H+0
HETATM   24  H   UNK     0      -2.276  -4.132   0.000  0.00  0.00           H+0
HETATM   25  C   UNK     0       1.243   1.978   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       3.838   1.209   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       4.237   2.697   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       5.725   3.095   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       6.123   4.583   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       5.034   5.672   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       7.611   4.981   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       4.927   0.120   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3   22                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    7                                                  
CONECT    5    4    6   10   21                                             
CONECT    6    5    1                                                       
CONECT    7    4    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11   20                                             
CONECT   10    9    5   14   24                                             
CONECT   11    9   12   15   23                                             
CONECT   12   11   13   17   18                                             
CONECT   13   12   14                                                       
CONECT   14   13   10                                                       
CONECT   15   11   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   12   19                                                  
CONECT   18   12                                                            
CONECT   19   17   25   26                                                  
CONECT   20    9                                                            
CONECT   21    5                                                            
CONECT   22    2                                                            
CONECT   23   11                                                            
CONECT   24   10                                                            
CONECT   25   19                                                            
CONECT   26   19   27   32                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29                                                            
CONECT   32   26                                                            
MASTER        0    0    0    0    0    0    0    0   32    0   70    0
END

COMPND    HMDB0004035
HETATM    1  C1  UNL     1       6.470   2.164  -1.834  1.00  0.00           C  
HETATM    2  C2  UNL     1       5.990   0.865  -1.227  1.00  0.00           C  
HETATM    3  C3  UNL     1       7.044  -0.222  -1.313  1.00  0.00           C  
HETATM    4  C4  UNL     1       5.685   1.180   0.253  1.00  0.00           C  
HETATM    5  C5  UNL     1       5.197  -0.021   0.969  1.00  0.00           C  
HETATM    6  C6  UNL     1       3.938  -0.671   0.517  1.00  0.00           C  
HETATM    7  O1  UNL     1       3.885  -1.835   1.397  1.00  0.00           O  
HETATM    8  C7  UNL     1       2.671   0.111   0.805  1.00  0.00           C  
HETATM    9  C8  UNL     1       2.638   1.442   0.174  1.00  0.00           C  
HETATM   10  C9  UNL     1       1.457  -0.718   0.557  1.00  0.00           C  
HETATM   11  C10 UNL     1       1.382  -1.937   1.453  1.00  0.00           C  
HETATM   12  C11 UNL     1      -0.102  -2.138   1.778  1.00  0.00           C  
HETATM   13  C12 UNL     1      -0.749  -1.392   0.713  1.00  0.00           C  
HETATM   14  C13 UNL     1      -2.142  -0.907   0.932  1.00  0.00           C  
HETATM   15  C14 UNL     1      -3.050  -1.853   1.599  1.00  0.00           C  
HETATM   16  C15 UNL     1      -4.442  -1.680   1.122  1.00  0.00           C  
HETATM   17  C16 UNL     1      -4.872  -0.849   0.207  1.00  0.00           C  
HETATM   18  C17 UNL     1      -6.318  -0.829  -0.132  1.00  0.00           C  
HETATM   19  C18 UNL     1      -6.763   0.360  -0.907  1.00  0.00           C  
HETATM   20  O2  UNL     1      -7.200   1.403  -0.062  1.00  0.00           O  
HETATM   21  C19 UNL     1      -5.827   0.839  -1.959  1.00  0.00           C  
HETATM   22  C20 UNL     1      -4.454   0.171  -1.916  1.00  0.00           C  
HETATM   23  C21 UNL     1      -3.917   0.085  -0.522  1.00  0.00           C  
HETATM   24  C22 UNL     1      -3.899   1.386   0.201  1.00  0.00           C  
HETATM   25  C23 UNL     1      -2.624  -0.673  -0.514  1.00  0.00           C  
HETATM   26  C24 UNL     1      -1.533  -0.180  -1.370  1.00  0.00           C  
HETATM   27  C25 UNL     1      -0.377   0.505  -0.699  1.00  0.00           C  
HETATM   28  C26 UNL     1       0.120  -0.123   0.570  1.00  0.00           C  
HETATM   29  C27 UNL     1      -0.163   0.799   1.720  1.00  0.00           C  
HETATM   30  H1  UNL     1       6.846   2.836  -1.062  1.00  0.00           H  
HETATM   31  H2  UNL     1       5.621   2.645  -2.399  1.00  0.00           H  
HETATM   32  H3  UNL     1       7.221   1.914  -2.611  1.00  0.00           H  
HETATM   33  H4  UNL     1       5.049   0.496  -1.662  1.00  0.00           H  
HETATM   34  H5  UNL     1       6.504  -1.191  -1.258  1.00  0.00           H  
HETATM   35  H6  UNL     1       7.541  -0.154  -2.307  1.00  0.00           H  
HETATM   36  H7  UNL     1       7.768  -0.175  -0.479  1.00  0.00           H  
HETATM   37  H8  UNL     1       6.737   1.369   0.683  1.00  0.00           H  
HETATM   38  H9  UNL     1       5.111   2.085   0.259  1.00  0.00           H  
HETATM   39  H10 UNL     1       6.065  -0.762   0.912  1.00  0.00           H  
HETATM   40  H11 UNL     1       5.178   0.156   2.103  1.00  0.00           H  
HETATM   41  H12 UNL     1       4.034  -0.990  -0.527  1.00  0.00           H  
HETATM   42  H13 UNL     1       4.644  -2.380   1.039  1.00  0.00           H  
HETATM   43  H14 UNL     1       2.767   0.333   1.932  1.00  0.00           H  
HETATM   44  H15 UNL     1       2.982   2.272   0.857  1.00  0.00           H  
HETATM   45  H16 UNL     1       3.096   1.462  -0.821  1.00  0.00           H  
HETATM   46  H17 UNL     1       1.574   1.807  -0.028  1.00  0.00           H  
HETATM   47  H18 UNL     1       1.575  -1.171  -0.482  1.00  0.00           H  
HETATM   48  H19 UNL     1       1.900  -1.824   2.423  1.00  0.00           H  
HETATM   49  H20 UNL     1       1.742  -2.864   0.985  1.00  0.00           H  
HETATM   50  H21 UNL     1      -0.367  -3.233   1.665  1.00  0.00           H  
HETATM   51  H22 UNL     1      -0.350  -1.892   2.821  1.00  0.00           H  
HETATM   52  H23 UNL     1      -0.631  -1.944  -0.244  1.00  0.00           H  
HETATM   53  H24 UNL     1      -2.221   0.084   1.432  1.00  0.00           H  
HETATM   54  H25 UNL     1      -2.724  -2.916   1.566  1.00  0.00           H  
HETATM   55  H26 UNL     1      -3.088  -1.566   2.697  1.00  0.00           H  
HETATM   56  H27 UNL     1      -5.224  -2.319   1.582  1.00  0.00           H  
HETATM   57  H28 UNL     1      -6.904  -0.889   0.814  1.00  0.00           H  
HETATM   58  H29 UNL     1      -6.608  -1.757  -0.706  1.00  0.00           H  
HETATM   59  H30 UNL     1      -7.717   0.047  -1.438  1.00  0.00           H  
HETATM   60  H31 UNL     1      -7.239   2.214  -0.650  1.00  0.00           H  
HETATM   61  H32 UNL     1      -5.692   1.956  -1.988  1.00  0.00           H  
HETATM   62  H33 UNL     1      -6.207   0.601  -2.998  1.00  0.00           H  
HETATM   63  H34 UNL     1      -4.586  -0.871  -2.286  1.00  0.00           H  
HETATM   64  H35 UNL     1      -3.835   0.702  -2.635  1.00  0.00           H  
HETATM   65  H36 UNL     1      -4.285   1.290   1.235  1.00  0.00           H  
HETATM   66  H37 UNL     1      -2.903   1.851   0.281  1.00  0.00           H  
HETATM   67  H38 UNL     1      -4.590   2.134  -0.295  1.00  0.00           H  
HETATM   68  H39 UNL     1      -2.894  -1.716  -0.864  1.00  0.00           H  
HETATM   69  H40 UNL     1      -1.080  -1.020  -1.982  1.00  0.00           H  
HETATM   70  H41 UNL     1      -1.862   0.535  -2.182  1.00  0.00           H  
HETATM   71  H42 UNL     1       0.423   0.526  -1.497  1.00  0.00           H  
HETATM   72  H43 UNL     1      -0.680   1.558  -0.557  1.00  0.00           H  
HETATM   73  H44 UNL     1       0.735   1.307   2.130  1.00  0.00           H  
HETATM   74  H45 UNL     1      -0.854   1.601   1.421  1.00  0.00           H  
HETATM   75  H46 UNL     1      -0.619   0.296   2.609  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    8   41
CONECT    7   42
CONECT    8    9   10   43
CONECT    9   44   45   46
CONECT   10   11   28   47
CONECT   11   12   48   49
CONECT   12   13   50   51
CONECT   13   14   28   52
CONECT   14   15   25   53
CONECT   15   16   54   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

HMDB0004035
     RDKit          3D
22b-Hydroxycholesterol
 75 78  0  0  0  0  0  0  0  0999 V2000
    6.4698    2.1643   -1.8337 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9901    0.8651   -1.2272 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0444   -0.2221   -1.3132 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6854    1.1800    0.2530 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1973   -0.0214    0.9691 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9384   -0.6709    0.5168 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.8854   -1.8353    1.3969 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6705    0.1108    0.8049 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6378    1.4421    0.1742 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4568   -0.7184    0.5574 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3819   -1.9373    1.4530 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1024   -2.1384    1.7779 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7489   -1.3921    0.7125 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1417   -0.9073    0.9321 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0501   -1.8531    1.5995 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4416   -1.6803    1.1223 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8716   -0.8495    0.2067 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3176   -0.8285   -0.1318 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7627    0.3599   -0.9073 C   0  0  1  0  0  0  0  0  0  0  0  0
   -7.1999    1.4031   -0.0623 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8275    0.8395   -1.9588 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4544    0.1705   -1.9161 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9170    0.0846   -0.5222 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.8986    1.3862    0.2012 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6240   -0.6730   -0.5140 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5328   -0.1801   -1.3700 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3768    0.5049   -0.6989 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1203   -0.1230    0.5704 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1630    0.7987    1.7205 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8462    2.8361   -1.0619 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6207    2.6448   -2.3987 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2212    1.9141   -2.6114 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0490    0.4956   -1.6617 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5036   -1.1914   -1.2576 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5406   -0.1541   -2.3072 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7680   -0.1747   -0.4795 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7367    1.3686    0.6830 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1110    2.0847    0.2587 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0649   -0.7621    0.9115 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1776    0.1562    2.1025 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0339   -0.9902   -0.5272 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6444   -2.3803    1.0390 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7675    0.3334    1.9318 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9821    2.2717    0.8571 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0960    1.4621   -0.8206 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5735    1.8067   -0.0280 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5748   -1.1708   -0.4819 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9002   -1.8245    2.4235 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7421   -2.8640    0.9851 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3671   -3.2328    1.6646 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3503   -1.8917    2.8207 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6308   -1.9441   -0.2441 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2209    0.0840    1.4319 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7241   -2.9162    1.5664 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0878   -1.5660    2.6965 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2237   -2.3194    1.5815 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9038   -0.8888    0.8141 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6080   -1.7569   -0.7058 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7172    0.0470   -1.4377 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2389    2.2142   -0.6503 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6922    1.9565   -1.9880 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2069    0.6009   -2.9976 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5861   -0.8713   -2.2858 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8348    0.7020   -2.6351 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2848    1.2903    1.2353 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9028    1.8511    0.2815 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5903    2.1340   -0.2951 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8938   -1.7164   -0.8640 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0799   -1.0205   -1.9818 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8621    0.5347   -2.1825 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4232    0.5263   -1.4972 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6805    1.5576   -0.5574 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7350    1.3066    2.1301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8543    1.6010    1.4206 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6190    0.2958    2.6091 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
  6  8  1  0
  8  9  1  0
  8 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  1  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  1
 23 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  1
 28 10  1  0
 28 13  1  0
 25 14  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  6
  7 42  1  0
  8 43  1  1
  9 44  1  0
  9 45  1  0
  9 46  1  0
 10 47  1  6
 11 48  1  0
 11 49  1  0
 12 50  1  0
 12 51  1  0
 13 52  1  6
 14 53  1  1
 15 54  1  0
 15 55  1  0
 16 56  1  0
 18 57  1  0
 18 58  1  0
 19 59  1  6
 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  6
 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
(3beta,22R)-Cholest-5-ene-3,22-diol	ChEBI
22beta-Hydroxycholesterol	ChEBI
22R-Hydroxycholesterol	ChEBI
Cholest-5-en-3beta,22R-diol	ChEBI
(22R)-22-Hydroxycholesterol	Kegg
(3b,22R)-Cholest-5-ene-3,22-diol	Generator
(3Β,22R)-cholest-5-ene-3,22-diol	Generator
22Β-hydroxycholesterol	Generator
Cholest-5-en-3b,22R-diol	Generator
Cholest-5-en-3β,22R-diol	Generator
22-Hydroxycholesterol, (3beta,20R,22R)-isomer	HMDB
22-Hydroxycholesterol, (3beta,20R,22S)-isomer	HMDB
Cholest-5-ene-3beta,22-diol	HMDB
22(R)-Hydroxycholesterol	HMDB
22-Hydroxycholesterol, (3beta,22S)-isomer	HMDB
22(R)OH Cholesterol	HMDB
22-Hydroxycholesterol	HMDB
22-Hydroxycholesterol, (3beta,22R)-isomer	HMDB
22S-Hydroxycholesterol	HMDB

Chemical Formula

C₂₇H₄₆O₂

Average Molecular Weight

402.6529

Monoisotopic Molecular Weight

402.349780716

IUPAC Name

(1S,2R,5S,10S,11S,14R,15S)-14-[(2S,3R)-3-hydroxy-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-5-ol

Traditional Name

22R-hydroxycholesterol

CAS Registry Number

22348-64-7

SMILES

[H][C@@]12CC[C@H]([C@H](C)[C@H](O)CCC(C)C)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC=C2C[C@@H](O)CC[C@]12C

InChI Identifier

InChI=1S/C27H46O2/c1-17(2)6-11-25(29)18(3)22-9-10-23-21-8-7-19-16-20(28)12-14-26(19,4)24(21)13-15-27(22,23)5/h7,17-18,20-25,28-29H,6,8-16H2,1-5H3/t18-,20-,21-,22+,23-,24-,25+,26-,27+/m0/s1

InChI Key

RZPAXNJLEKLXNO-GFKLAVDKSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as dihydroxy bile acids, alcohols and derivatives. Dihydroxy bile acids, alcohols and derivatives are compounds containing or derived from a bile acid or alcohol, and which bears exactly two carboxylic acid groups.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Bile acids, alcohols and derivatives

Direct Parent

Dihydroxy bile acids, alcohols and derivatives

Alternative Parents

Substituents

Cholesterol
Cholesterol-skeleton
Cholestane-skeleton
Dihydroxy bile acid, alcohol, or derivatives
22-hydroxysteroid
Hydroxysteroid
3-hydroxy-delta-5-steroid
3-beta-hydroxysteroid
3-hydroxysteroid
3-beta-hydroxy-delta-5-steroid
Delta-5-steroid
Cyclic alcohol
Secondary alcohol
Organooxygen compound
Hydrocarbon derivative
Organic oxygen compound
Alcohol
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

oxysterol (CHEBI:67237 )
22-hydroxy steroid (CHEBI:67237 )
Cholesterol and derivatives (C05502 )
Cholesterol and derivatives (LMST01010086 )

Ontology

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

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

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M-H]-	Not Available	217.739	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000273

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.00065 g/L	ALOGPS
logP	5.69	ALOGPS
logP	5.8	ChemAxon
logS	-5.8	ALOGPS
pKa (Strongest Acidic)	18.2	ChemAxon
pKa (Strongest Basic)	-0.73	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	122.21 m³·mol⁻¹	ChemAxon
Polarizability	50.77 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 Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	196.061	31661259
DarkChem	[M-H]-	199.228	31661259
DeepCCS	[M-2H]-	241.442	30932474
DeepCCS	[M+Na]+	216.718	30932474
AllCCS	[M+H]+	206.2	32859911
AllCCS	[M+H-H2O]+	204.2	32859911
AllCCS	[M+NH4]+	208.1	32859911
AllCCS	[M+Na]+	208.6	32859911
AllCCS	[M-H]-	203.4	32859911
AllCCS	[M+Na-2H]-	205.3	32859911
AllCCS	[M+HCOO]-	207.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
22b-Hydroxycholesterol	[H][C@@]12CC[C@H]([C@H](C)[C@H](O)CCC(C)C)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC=C2C[C@@H](O)CC[C@]12C	2630.6	Standard polar	33892256
22b-Hydroxycholesterol	[H][C@@]12CC[C@H]([C@H](C)[C@H](O)CCC(C)C)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC=C2C[C@@H](O)CC[C@]12C	3287.9	Standard non polar	33892256
22b-Hydroxycholesterol	[H][C@@]12CC[C@H]([C@H](C)[C@H](O)CCC(C)C)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC=C2C[C@@H](O)CC[C@]12C	3412.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
22b-Hydroxycholesterol,1TMS,isomer #1	CC(C)CC[C@@H](O[Si](C)(C)C)[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CC=C4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@@]21C	3351.7	Semi standard non polar	33892256
22b-Hydroxycholesterol,1TMS,isomer #2	CC(C)CC[C@@H](O)[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CC=C4C[C@@H](O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C	3351.7	Semi standard non polar	33892256
22b-Hydroxycholesterol,2TMS,isomer #1	CC(C)CC[C@@H](O[Si](C)(C)C)[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CC=C4C[C@@H](O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C	3354.8	Semi standard non polar	33892256
22b-Hydroxycholesterol,1TBDMS,isomer #1	CC(C)CC[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CC=C4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@@]21C	3603.8	Semi standard non polar	33892256
22b-Hydroxycholesterol,1TBDMS,isomer #2	CC(C)CC[C@@H](O)[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C	3574.9	Semi standard non polar	33892256
22b-Hydroxycholesterol,2TBDMS,isomer #1	CC(C)CC[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C	3850.4	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 22b-Hydroxycholesterol GC-MS (Non-derivatized) - 70eV, Positive	splash10-00dr-1009000000-ed60780a407ecfba86a3	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 22b-Hydroxycholesterol GC-MS (2 TMS) - 70eV, Positive	splash10-001i-2111490000-e04dc3bb7ab36f5571f8	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 22b-Hydroxycholesterol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 22b-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
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 22b-Hydroxycholesterol 10V, Positive-QTOF	splash10-0f79-0009200000-2ae8fb6172d46e818cef	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 22b-Hydroxycholesterol 20V, Positive-QTOF	splash10-00kr-2119100000-9925177c38f63ddc14a1	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 22b-Hydroxycholesterol 40V, Positive-QTOF	splash10-0a4i-6049000000-44d8c7fcd6055391f8dd	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 22b-Hydroxycholesterol 10V, Negative-QTOF	splash10-0udi-0004900000-10b9f0186b2a2ac37d53	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 22b-Hydroxycholesterol 20V, Negative-QTOF	splash10-0ue9-1019700000-6b5a6ee8410d635f82c6	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 22b-Hydroxycholesterol 40V, Negative-QTOF	splash10-0f79-4059000000-8d88574ef4b0b7d39b85	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 22b-Hydroxycholesterol 10V, Positive-QTOF	splash10-0gbi-0109200000-bd7670f27e11ece2eac0	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 22b-Hydroxycholesterol 20V, Positive-QTOF	splash10-014r-5339000000-858a48abc2f1b02935f5	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 22b-Hydroxycholesterol 40V, Positive-QTOF	splash10-0a4l-6960000000-73b0982e9fcef4fa83d0	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 22b-Hydroxycholesterol 10V, Negative-QTOF	splash10-0udi-0000900000-84d3363c4aa86f104c55	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 22b-Hydroxycholesterol 20V, Negative-QTOF	splash10-0udi-0012900000-973e1345841477d95a76	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 22b-Hydroxycholesterol 40V, Negative-QTOF	splash10-0uea-7049300000-8042d2ca5cd8469196da	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular

Biospecimen Locations

Not Available

Tissue Locations

Adrenal Cortex
Epidermis
Fibroblasts
Neuron

Pathways

Name	SMPDB/PathBank	KEGG
Steroidogenesis
Adrenal Hyperplasia Type 3 or Congenital Adrenal Hyperplasia due to 21-hydroxylase Deficiency		Not Available
Congenital Lipoid Adrenal Hyperplasia (CLAH) or Lipoid CAH		Not Available
Adrenal Hyperplasia Type 5 or Congenital Adrenal Hyperplasia due to 17 Alpha-hydroxylase Deficiency		Not Available
17-alpha-hydroxylase deficiency (CYP17)		Not Available

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB023285

KNApSAcK ID

Not Available

Chemspider ID

146693

KEGG Compound ID

C05502

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

7006

PubChem Compound

167685

PDB ID

Not Available

ChEBI ID

67237

Food Biomarker Ontology

Not Available

VMH ID

M00606

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Koreeda, Masato; Ricca, Daniel J. Chirality transfer in stereoselective synthesis. A highly stereocontrolled synthesis of 22-hydroxylated steroid side chains via the [2,3]-Wittig rearrangement. Journal of Organic Chemistry (1986), 51(21), 4090-2.

Material Safety Data Sheet (MSDS)

Not Available

General References

Haidar B, Denis M, Marcil M, Krimbou L, Genest J Jr: Apolipoprotein A-I activates cellular cAMP signaling through the ABCA1 transporter. J Biol Chem. 2004 Mar 12;279(11):9963-9. Epub 2003 Dec 29. [PubMed:14701824 ]
Yao ZX, Brown RC, Teper G, Greeson J, Papadopoulos V: 22R-Hydroxycholesterol protects neuronal cells from beta-amyloid-induced cytotoxicity by binding to beta-amyloid peptide. J Neurochem. 2002 Dec;83(5):1110-9. [PubMed:12437582 ]
Matsuzaki J, Tsuji T, Imazeki I, Ikeda H, Nishimura T: Immunosteroid as a regulator for Th1/Th2 balance: its possible role in autoimmune diseases. Autoimmunity. 2005 Aug;38(5):369-75. [PubMed:16227152 ]
Tuckey RC: Cholesterol side-chain cleavage by mitochondria from the human placenta. Studies using hydroxycholesterols as substrates. J Steroid Biochem Mol Biol. 1992 Sep;42(8):883-90. [PubMed:1525048 ]
Hanley K, Ng DC, He SS, Lau P, Min K, Elias PM, Bikle DD, Mangelsdorf DJ, Williams ML, Feingold KR: Oxysterols induce differentiation in human keratinocytes and increase Ap-1-dependent involucrin transcription. J Invest Dermatol. 2000 Mar;114(3):545-53. [PubMed:10692116 ]

Enzymes

Enzyme Details

1. Cholesterol side-chain cleavage enzyme, mitochondrial

General function:: Involved in monooxygenase activity
Specific function:: Catalyzes the side-chain cleavage reaction of cholesterol to pregnenolone.
Gene Name:: CYP11A1
Uniprot ID:: P05108
Molecular weight:: 60101.87

Reactions

Cholesterol + Oxygen + Reduced adrenal ferredoxin + Hydrogen Ion → 22b-Hydroxycholesterol + Water + Oxidized adrenal ferredoxin	details
22b-Hydroxycholesterol + Oxygen + Reduced adrenal ferredoxin + Hydrogen Ion → 20a,22b-Dihydroxycholesterol + Water + Oxidized adrenal ferredoxin	details

Showing metabocard for 22b-Hydroxycholesterol (HMDB0004035)

MOL for HMDB0004035 (22b-Hydroxycholesterol)

3D MOL for HMDB0004035 (22b-Hydroxycholesterol)

3D SDF for HMDB0004035 (22b-Hydroxycholesterol)

3D-SDF for HMDB0004035 (22b-Hydroxycholesterol)

PDB for HMDB0004035 (22b-Hydroxycholesterol)

3D PDB for HMDB0004035 (22b-Hydroxycholesterol)

SMILES for HMDB0004035 (22b-Hydroxycholesterol)

INCHI for HMDB0004035 (22b-Hydroxycholesterol)

Structure for HMDB0004035 (22b-Hydroxycholesterol)

3D Structure for HMDB0004035 (22b-Hydroxycholesterol)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

Reactions