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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (2) Show 2 proteins XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2007-05-22 21:16:34 UTC

Update Date

2022-03-07 02:49:31 UTC

HMDB ID

HMDB0006283

Secondary Accession Numbers

HMDB06283

Metabolite Identification

Common Name

20alpha-Hydroxycholesterol

Description

20alpha-Hydroxycholesterol belongs to the class of organic compounds known as cholesterols and derivatives. Cholesterols and derivatives are compounds containing a 3-hydroxylated cholestane core. Thus, 20alpha-hydroxycholesterol is considered to be a sterol. Based on a literature review very few articles have been published on 20alpha-Hydroxycholesterol.

Structure

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


  Mrv0541 02231217512D          

 29 32  0  0  1  0            999 V2000
    6.9960   -2.9136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7104   -2.5011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7104   -1.6761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4249   -2.9136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1394   -2.5011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8538   -2.9136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5683   -2.5011    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.9808   -3.2156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1558   -1.7867    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.2828   -2.0886    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   11.3690   -1.2682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1760   -1.0966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5885   -1.8111    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   13.3955   -1.9826    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   13.9475   -1.3695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7545   -1.5411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0094   -2.3257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8164   -2.4972    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0713   -3.2818    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   16.8783   -3.4534    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.5193   -3.8949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7123   -3.7234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4574   -2.9388    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   13.9053   -3.5519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6504   -2.7673    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   13.0984   -3.3803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2914   -3.2088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0365   -2.4242    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.4234   -2.9762    0.0000 C   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
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  6  0  0  0
  7  9  1  6  0  0  0
 10  7  1  1  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 13 12  1  1  0  0  0
 13 14  1  0  0  0  0
 14 15  1  6  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  1  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 17 23  1  0  0  0  0
 23 24  1  1  0  0  0
 23 25  1  0  0  0  0
 14 25  1  0  0  0  0
 25 26  1  1  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 10 28  1  0  0  0  0
 13 28  1  0  0  0  0
 28 29  1  1  0  0  0
M  END

HMDB0006283
     RDKit          3D
20alpha-Hydroxycholesterol
 75 78  0  0  0  0  0  0  0  0999 V2000
    6.8050   -0.5500    1.7427 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5615   -1.2245    1.2051 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5051   -1.2509    2.2558 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0908   -0.4399   -0.0516 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8707   -1.0586   -0.6213 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2737   -0.5035   -1.8426 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7827    0.9000   -1.8676 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9184    1.9073   -1.5914 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5308    1.1774   -3.2498 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6142    1.1667   -1.0188 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2162    2.6392   -1.0968 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2244    2.5665   -1.5244 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6309    1.4291   -0.6338 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9936    0.9804   -0.6730 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8987    2.1473   -0.1903 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2759    1.6019   -0.2001 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5517    0.3401    0.0300 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9677   -0.0877   -0.0044 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2665   -0.5620    1.4175 C   0  0  1  0  0  0  0  0  0  0  0  0
   -7.5761   -0.9333    1.5757 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3526   -1.7123    1.7066 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8846   -1.3461    1.6735 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5295   -0.6989    0.3303 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.5633   -1.8121   -0.6927 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1455   -0.0952    0.4022 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0794   -1.1280    0.3453 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2764   -0.6820    0.0042 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3661    0.3718   -1.1056 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0233   -0.2645   -2.3670 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7151   -0.8134    1.1916 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6885    0.5644    1.6590 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9246   -0.7354    2.8416 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8352   -2.2489    0.9222 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0126   -1.1402    3.2588 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0411   -2.2632    2.2916 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7649   -0.4433    2.1949 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8705    0.5697    0.4058 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9784   -0.4381   -0.7059 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1598   -2.1383   -0.8513 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1069   -1.2155    0.2063 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3944   -1.1625   -2.1196 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9813   -0.7004   -2.7082 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9382    2.7065   -2.4032 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8521    1.3586   -1.7935 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8501    2.3554   -0.6070 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4298    1.0594   -3.6707 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9769    1.0286    0.0546 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2065    3.0751   -0.0661 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8512    3.2111   -1.7819 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2377    2.2049   -2.5686 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7863    3.4873   -1.3499 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3651    1.7278    0.4106 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4648    0.6832   -1.6147 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6194    2.4329    0.8333 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7835    2.9626   -0.9249 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1119    2.2797   -0.4093 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2223   -0.8237   -0.7624 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6598    0.7759   -0.1647 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9900    0.3030    2.0757 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0919   -1.0047    0.7332 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5622   -2.0304    2.7646 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5914   -2.5778    1.0784 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6933   -0.6478    2.5174 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3119   -2.2923    1.7646 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9080   -1.6007   -1.5608 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5774   -1.9663   -1.0810 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2815   -2.7714   -0.1855 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0588    0.4432    1.3665 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3847   -2.0312   -0.2670 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0192   -1.5651    1.3912 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8418   -1.5918   -0.3628 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8301   -0.3285    0.8929 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0977   -0.1706   -2.6677 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0684   -1.3912   -2.2512 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6524   -0.0143   -3.1817 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  6
  7 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  6
 23 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  6
 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  0
  6 42  1  0
  8 43  1  0
  8 44  1  0
  8 45  1  0
  9 46  1  0
 10 47  1  1
 11 48  1  0
 11 49  1  0
 12 50  1  0
 12 51  1  0
 13 52  1  1
 14 53  1  6
 15 54  1  0
 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


  Mrv0541 02231217512D          

 29 32  0  0  1  0            999 V2000
    6.9960   -2.9136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7104   -2.5011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7104   -1.6761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4249   -2.9136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1394   -2.5011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8538   -2.9136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5683   -2.5011    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.9808   -3.2156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1558   -1.7867    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.2828   -2.0886    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   11.3690   -1.2682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1760   -1.0966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5885   -1.8111    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   13.3955   -1.9826    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   13.9475   -1.3695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7545   -1.5411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0094   -2.3257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8164   -2.4972    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0713   -3.2818    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   16.8783   -3.4534    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.5193   -3.8949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7123   -3.7234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4574   -2.9388    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   13.9053   -3.5519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6504   -2.7673    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   13.0984   -3.3803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2914   -3.2088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0365   -2.4242    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.4234   -2.9762    0.0000 C   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
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  6  0  0  0
  7  9  1  6  0  0  0
 10  7  1  1  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 13 12  1  1  0  0  0
 13 14  1  0  0  0  0
 14 15  1  6  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  1  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 17 23  1  0  0  0  0
 23 24  1  1  0  0  0
 23 25  1  0  0  0  0
 14 25  1  0  0  0  0
 25 26  1  1  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 10 28  1  0  0  0  0
 13 28  1  0  0  0  0
 28 29  1  1  0  0  0
M  END
> <DATABASE_ID>
HMDB0006283

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C27H46O2/c1-18(2)7-6-14-27(5,29)24-11-10-22-21-9-8-19-17-20(28)12-15-25(19,3)23(21)13-16-26(22,24)4/h8,18,20-24,28-29H,6-7,9-17H2,1-5H3/t20-,21-,22-,23-,24-,25-,26-,27+/m0/s1

> <INCHI_KEY>
MCKLJFJEQRYRQT-MGNSQDQZSA-N

> <FORMULA>
C27H46O2

> <MOLECULAR_WEIGHT>
402.6529

> <EXACT_MASS>
402.349780716

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
51.09984293738356

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
6.06

> <JCHEM_LOGP>
5.797681805666667

> <ALOGPS_LOGS>
-5.85

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.20428950550382

> <JCHEM_PKA_STRONGEST_BASIC>
-0.2584596169281518

> <JCHEM_POLAR_SURFACE_AREA>
40.46

> <JCHEM_REFRACTIVITY>
122.29859999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.71e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
20a-hydroxy cholesterol

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0006283
     RDKit          3D
20alpha-Hydroxycholesterol
 75 78  0  0  0  0  0  0  0  0999 V2000
    6.8050   -0.5500    1.7427 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5615   -1.2245    1.2051 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5051   -1.2509    2.2558 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0908   -0.4399   -0.0516 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8707   -1.0586   -0.6213 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2737   -0.5035   -1.8426 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7827    0.9000   -1.8676 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9184    1.9073   -1.5914 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5308    1.1774   -3.2498 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6142    1.1667   -1.0188 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2162    2.6392   -1.0968 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2244    2.5665   -1.5244 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6309    1.4291   -0.6338 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9936    0.9804   -0.6730 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8987    2.1473   -0.1903 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2759    1.6019   -0.2001 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5517    0.3401    0.0300 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9677   -0.0877   -0.0044 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2665   -0.5620    1.4175 C   0  0  1  0  0  0  0  0  0  0  0  0
   -7.5761   -0.9333    1.5757 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3526   -1.7123    1.7066 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8846   -1.3461    1.6735 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5295   -0.6989    0.3303 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.5633   -1.8121   -0.6927 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1455   -0.0952    0.4022 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0794   -1.1280    0.3453 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2764   -0.6820    0.0042 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3661    0.3718   -1.1056 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0233   -0.2645   -2.3670 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7151   -0.8134    1.1916 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6885    0.5644    1.6590 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9246   -0.7354    2.8416 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8352   -2.2489    0.9222 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0126   -1.1402    3.2588 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0411   -2.2632    2.2916 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7649   -0.4433    2.1949 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8705    0.5697    0.4058 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9784   -0.4381   -0.7059 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1598   -2.1383   -0.8513 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1069   -1.2155    0.2063 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3944   -1.1625   -2.1196 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9813   -0.7004   -2.7082 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9382    2.7065   -2.4032 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8521    1.3586   -1.7935 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8501    2.3554   -0.6070 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4298    1.0594   -3.6707 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9769    1.0286    0.0546 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2065    3.0751   -0.0661 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8512    3.2111   -1.7819 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2377    2.2049   -2.5686 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7863    3.4873   -1.3499 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3651    1.7278    0.4106 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4648    0.6832   -1.6147 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6194    2.4329    0.8333 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7835    2.9626   -0.9249 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1119    2.2797   -0.4093 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2223   -0.8237   -0.7624 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6598    0.7759   -0.1647 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9900    0.3030    2.0757 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0919   -1.0047    0.7332 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5622   -2.0304    2.7646 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5914   -2.5778    1.0784 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6933   -0.6478    2.5174 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3119   -2.2923    1.7646 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9080   -1.6007   -1.5608 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5774   -1.9663   -1.0810 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2815   -2.7714   -0.1855 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0588    0.4432    1.3665 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3847   -2.0312   -0.2670 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0192   -1.5651    1.3912 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8418   -1.5918   -0.3628 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8301   -0.3285    0.8929 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0977   -0.1706   -2.6677 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0684   -1.3912   -2.2512 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6524   -0.0143   -3.1817 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  6
  7 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  6
 23 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  6
 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  0
  6 42  1  0
  8 43  1  0
  8 44  1  0
  8 45  1  0
  9 46  1  0
 10 47  1  1
 11 48  1  0
 11 49  1  0
 12 50  1  0
 12 51  1  0
 13 52  1  1
 14 53  1  6
 15 54  1  0
 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                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  C   UNK     0      13.059  -5.439   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      14.393  -4.669   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      14.393  -3.129   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      15.726  -5.439   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      17.060  -4.669   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      18.394  -5.439   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      19.727  -4.669   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      20.497  -6.002   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      18.957  -3.335   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      21.061  -3.899   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      21.222  -2.367   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      22.729  -2.047   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      23.499  -3.381   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      25.005  -3.701   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      26.035  -2.556   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      27.542  -2.877   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      28.018  -4.341   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      29.524  -4.661   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      30.000  -6.126   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      31.506  -6.446   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      28.969  -7.270   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      27.463  -6.950   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      26.987  -5.486   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      25.957  -6.630   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      25.481  -5.166   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      24.450  -6.310   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      22.944  -5.990   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      22.468  -4.525   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      21.324  -5.556   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9   10                                             
CONECT    8    7                                                            
CONECT    9    7                                                            
CONECT   10    7   11   28                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   28                                                  
CONECT   14   13   15   25                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   23                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   17   24   25                                             
CONECT   24   23                                                            
CONECT   25   23   14   26                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   10   13   29                                             
CONECT   29   28                                                            
MASTER        0    0    0    0    0    0    0    0   29    0   64    0
END

COMPND    HMDB0006283
HETATM    1  C1  UNL     1       6.805  -0.550   1.743  1.00  0.00           C  
HETATM    2  C2  UNL     1       5.561  -1.225   1.205  1.00  0.00           C  
HETATM    3  C3  UNL     1       4.505  -1.251   2.256  1.00  0.00           C  
HETATM    4  C4  UNL     1       5.091  -0.440  -0.052  1.00  0.00           C  
HETATM    5  C5  UNL     1       3.871  -1.059  -0.621  1.00  0.00           C  
HETATM    6  C6  UNL     1       3.274  -0.503  -1.843  1.00  0.00           C  
HETATM    7  C7  UNL     1       2.783   0.900  -1.868  1.00  0.00           C  
HETATM    8  C8  UNL     1       3.918   1.907  -1.591  1.00  0.00           C  
HETATM    9  O1  UNL     1       2.531   1.177  -3.250  1.00  0.00           O  
HETATM   10  C9  UNL     1       1.614   1.167  -1.019  1.00  0.00           C  
HETATM   11  C10 UNL     1       1.216   2.639  -1.097  1.00  0.00           C  
HETATM   12  C11 UNL     1      -0.224   2.566  -1.524  1.00  0.00           C  
HETATM   13  C12 UNL     1      -0.631   1.429  -0.634  1.00  0.00           C  
HETATM   14  C13 UNL     1      -1.994   0.980  -0.673  1.00  0.00           C  
HETATM   15  C14 UNL     1      -2.899   2.147  -0.190  1.00  0.00           C  
HETATM   16  C15 UNL     1      -4.276   1.602  -0.200  1.00  0.00           C  
HETATM   17  C16 UNL     1      -4.552   0.340   0.030  1.00  0.00           C  
HETATM   18  C17 UNL     1      -5.968  -0.088  -0.004  1.00  0.00           C  
HETATM   19  C18 UNL     1      -6.267  -0.562   1.417  1.00  0.00           C  
HETATM   20  O2  UNL     1      -7.576  -0.933   1.576  1.00  0.00           O  
HETATM   21  C19 UNL     1      -5.353  -1.712   1.707  1.00  0.00           C  
HETATM   22  C20 UNL     1      -3.885  -1.346   1.673  1.00  0.00           C  
HETATM   23  C21 UNL     1      -3.529  -0.699   0.330  1.00  0.00           C  
HETATM   24  C22 UNL     1      -3.563  -1.812  -0.693  1.00  0.00           C  
HETATM   25  C23 UNL     1      -2.146  -0.095   0.402  1.00  0.00           C  
HETATM   26  C24 UNL     1      -1.079  -1.128   0.345  1.00  0.00           C  
HETATM   27  C25 UNL     1       0.276  -0.682   0.004  1.00  0.00           C  
HETATM   28  C26 UNL     1       0.366   0.372  -1.106  1.00  0.00           C  
HETATM   29  C27 UNL     1      -0.023  -0.265  -2.367  1.00  0.00           C  
HETATM   30  H1  UNL     1       7.715  -0.813   1.192  1.00  0.00           H  
HETATM   31  H2  UNL     1       6.688   0.564   1.659  1.00  0.00           H  
HETATM   32  H3  UNL     1       6.925  -0.735   2.842  1.00  0.00           H  
HETATM   33  H4  UNL     1       5.835  -2.249   0.922  1.00  0.00           H  
HETATM   34  H5  UNL     1       5.013  -1.140   3.259  1.00  0.00           H  
HETATM   35  H6  UNL     1       4.041  -2.263   2.292  1.00  0.00           H  
HETATM   36  H7  UNL     1       3.765  -0.443   2.195  1.00  0.00           H  
HETATM   37  H8  UNL     1       4.871   0.570   0.406  1.00  0.00           H  
HETATM   38  H9  UNL     1       5.978  -0.438  -0.706  1.00  0.00           H  
HETATM   39  H10 UNL     1       4.160  -2.138  -0.851  1.00  0.00           H  
HETATM   40  H11 UNL     1       3.107  -1.216   0.206  1.00  0.00           H  
HETATM   41  H12 UNL     1       2.394  -1.162  -2.120  1.00  0.00           H  
HETATM   42  H13 UNL     1       3.981  -0.700  -2.708  1.00  0.00           H  
HETATM   43  H14 UNL     1       3.938   2.707  -2.403  1.00  0.00           H  
HETATM   44  H15 UNL     1       4.852   1.359  -1.793  1.00  0.00           H  
HETATM   45  H16 UNL     1       3.850   2.355  -0.607  1.00  0.00           H  
HETATM   46  H17 UNL     1       3.430   1.059  -3.671  1.00  0.00           H  
HETATM   47  H18 UNL     1       1.977   1.029   0.055  1.00  0.00           H  
HETATM   48  H19 UNL     1       1.206   3.075  -0.066  1.00  0.00           H  
HETATM   49  H20 UNL     1       1.851   3.211  -1.782  1.00  0.00           H  
HETATM   50  H21 UNL     1      -0.238   2.205  -2.569  1.00  0.00           H  
HETATM   51  H22 UNL     1      -0.786   3.487  -1.350  1.00  0.00           H  
HETATM   52  H23 UNL     1      -0.365   1.728   0.411  1.00  0.00           H  
HETATM   53  H24 UNL     1      -2.465   0.683  -1.615  1.00  0.00           H  
HETATM   54  H25 UNL     1      -2.619   2.433   0.833  1.00  0.00           H  
HETATM   55  H26 UNL     1      -2.783   2.963  -0.925  1.00  0.00           H  
HETATM   56  H27 UNL     1      -5.112   2.280  -0.409  1.00  0.00           H  
HETATM   57  H28 UNL     1      -6.222  -0.824  -0.762  1.00  0.00           H  
HETATM   58  H29 UNL     1      -6.660   0.776  -0.165  1.00  0.00           H  
HETATM   59  H30 UNL     1      -5.990   0.303   2.076  1.00  0.00           H  
HETATM   60  H31 UNL     1      -8.092  -1.005   0.733  1.00  0.00           H  
HETATM   61  H32 UNL     1      -5.562  -2.030   2.765  1.00  0.00           H  
HETATM   62  H33 UNL     1      -5.591  -2.578   1.078  1.00  0.00           H  
HETATM   63  H34 UNL     1      -3.693  -0.648   2.517  1.00  0.00           H  
HETATM   64  H35 UNL     1      -3.312  -2.292   1.765  1.00  0.00           H  
HETATM   65  H36 UNL     1      -2.908  -1.601  -1.561  1.00  0.00           H  
HETATM   66  H37 UNL     1      -4.577  -1.966  -1.081  1.00  0.00           H  
HETATM   67  H38 UNL     1      -3.282  -2.771  -0.185  1.00  0.00           H  
HETATM   68  H39 UNL     1      -2.059   0.443   1.366  1.00  0.00           H  
HETATM   69  H40 UNL     1      -1.385  -2.031  -0.267  1.00  0.00           H  
HETATM   70  H41 UNL     1      -1.019  -1.565   1.391  1.00  0.00           H  
HETATM   71  H42 UNL     1       0.842  -1.592  -0.363  1.00  0.00           H  
HETATM   72  H43 UNL     1       0.830  -0.329   0.893  1.00  0.00           H  
HETATM   73  H44 UNL     1      -1.098  -0.171  -2.668  1.00  0.00           H  
HETATM   74  H45 UNL     1       0.068  -1.391  -2.251  1.00  0.00           H  
HETATM   75  H46 UNL     1       0.652  -0.014  -3.182  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   10
CONECT    8   43   44   45
CONECT    9   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

HMDB0006283
     RDKit          3D
20alpha-Hydroxycholesterol
 75 78  0  0  0  0  0  0  0  0999 V2000
    6.8050   -0.5500    1.7427 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5615   -1.2245    1.2051 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5051   -1.2509    2.2558 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0908   -0.4399   -0.0516 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8707   -1.0586   -0.6213 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2737   -0.5035   -1.8426 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7827    0.9000   -1.8676 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9184    1.9073   -1.5914 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5308    1.1774   -3.2498 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6142    1.1667   -1.0188 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2162    2.6392   -1.0968 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2244    2.5665   -1.5244 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6309    1.4291   -0.6338 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9936    0.9804   -0.6730 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8987    2.1473   -0.1903 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2759    1.6019   -0.2001 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5517    0.3401    0.0300 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9677   -0.0877   -0.0044 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2665   -0.5620    1.4175 C   0  0  1  0  0  0  0  0  0  0  0  0
   -7.5761   -0.9333    1.5757 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3526   -1.7123    1.7066 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8846   -1.3461    1.6735 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5295   -0.6989    0.3303 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.5633   -1.8121   -0.6927 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1455   -0.0952    0.4022 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0794   -1.1280    0.3453 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2764   -0.6820    0.0042 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3661    0.3718   -1.1056 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0233   -0.2645   -2.3670 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7151   -0.8134    1.1916 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6885    0.5644    1.6590 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9246   -0.7354    2.8416 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8352   -2.2489    0.9222 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0126   -1.1402    3.2588 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0411   -2.2632    2.2916 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7649   -0.4433    2.1949 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8705    0.5697    0.4058 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9784   -0.4381   -0.7059 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1598   -2.1383   -0.8513 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1069   -1.2155    0.2063 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3944   -1.1625   -2.1196 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9813   -0.7004   -2.7082 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9382    2.7065   -2.4032 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8521    1.3586   -1.7935 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8501    2.3554   -0.6070 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4298    1.0594   -3.6707 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9769    1.0286    0.0546 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2065    3.0751   -0.0661 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8512    3.2111   -1.7819 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2377    2.2049   -2.5686 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7863    3.4873   -1.3499 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3651    1.7278    0.4106 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4648    0.6832   -1.6147 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6194    2.4329    0.8333 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7835    2.9626   -0.9249 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1119    2.2797   -0.4093 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2223   -0.8237   -0.7624 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6598    0.7759   -0.1647 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9900    0.3030    2.0757 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0919   -1.0047    0.7332 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5622   -2.0304    2.7646 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5914   -2.5778    1.0784 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6933   -0.6478    2.5174 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3119   -2.2923    1.7646 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9080   -1.6007   -1.5608 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5774   -1.9663   -1.0810 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2815   -2.7714   -0.1855 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0588    0.4432    1.3665 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3847   -2.0312   -0.2670 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0192   -1.5651    1.3912 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8418   -1.5918   -0.3628 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8301   -0.3285    0.8929 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0977   -0.1706   -2.6677 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0684   -1.3912   -2.2512 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6524   -0.0143   -3.1817 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  6
  7 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  6
 23 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  6
 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  0
  6 42  1  0
  8 43  1  0
  8 44  1  0
  8 45  1  0
  9 46  1  0
 10 47  1  1
 11 48  1  0
 11 49  1  0
 12 50  1  0
 12 51  1  0
 13 52  1  1
 14 53  1  6
 15 54  1  0
 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
20a-Hydroxycholesterol	Generator
20Α-hydroxycholesterol	Generator
(20S)-20-Hydroxycholesterol	MeSH
(20S)-Cholest-5-ene-3 beta,20-diol	MeSH
20 alpha-Hydroxycholesterol	MeSH
20-Hydroxycholesterol	MeSH
20-Hydroxycholesterol, (3beta,20 xi)-isomer	MeSH
20-Hydroxycholesterol, 3H-labeled, (3beta,20 xi)-isomer	MeSH
20R-Hydroxycholesterol	MeSH
(3beta,20R)-Cholest-5-ene-3,20-diol	HMDB
20alpha-Hydroxy cholesterol	HMDB

Chemical Formula

C₂₇H₄₆O₂

Average Molecular Weight

402.6529

Monoisotopic Molecular Weight

402.349780716

IUPAC Name

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

Traditional Name

20a-hydroxy cholesterol

CAS Registry Number

516-72-3

SMILES

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

InChI Identifier

InChI=1S/C27H46O2/c1-18(2)7-6-14-27(5,29)24-11-10-22-21-9-8-19-17-20(28)12-15-25(19,3)23(21)13-16-26(22,24)4/h8,18,20-24,28-29H,6-7,9-17H2,1-5H3/t20-,21-,22-,23-,24-,25-,26-,27+/m0/s1

InChI Key

MCKLJFJEQRYRQT-MGNSQDQZSA-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
20-hydroxysteroid
3-beta-hydroxy-delta-5-steroid
Hydroxysteroid
3-hydroxy-delta-5-steroid
3-hydroxysteroid
3-beta-hydroxysteroid
Delta-5-steroid
Tertiary alcohol
Cyclic alcohol
Secondary alcohol
Organooxygen compound
Hydrocarbon derivative
Organic oxygen compound
Alcohol
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

Cholesterol and derivatives (LMST01010211 )

Ontology

Physiological effect

Health effect

Metabolic syndrome (HMDB: HMDB0006283)

Disposition

Biological location

Cytoplasm (HMDB: HMDB0006283)
Cell membrane (HMDB: HMDB0006283)

Cellular substructure

Organelle

Mitochondria

Mitochondria (HMDB: HMDB0006283)

Biofluid or Excreta

Urine (HMDB: HMDB0006283)

Tissue substructure

Route of exposure

Enteral

Ingestion (HMDB: HMDB0006283)

Source

Endogenous

Endogenous (HMDB: HMDB0006283)

Exogenous

Food

Food (HMDB: HMDB0006283)

Animal origin

Poultry

Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)
Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)

Equine

Horse (FooDB: FOOD00378)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Steroidogenesis (HMDB: HMDB0006283)

Congenital Lipoid Adrenal Hyperplasia (CLAH) or Lipoid CAH (HMDB: HMDB0006283)

Disease pathway

Chemical reaction

Lipid peroxidation (HMDB: HMDB0006283)

Biochemical process

Fatty acid metabolism (HMDB: HMDB0006283)

Cellular process

Cell signaling (HMDB: HMDB0006283)

Multicellular process

Inflammatory response (HMDB: HMDB0006283)

Role

Biological role

Membrane stabilizer (HMDB: HMDB0006283)

Molecular messenger

Hormone (HMDB: HMDB0006283)

Industrial application

Pharmaceutical industry

Pharmaceutical (HMDB: HMDB0006283)

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0006283)

Emulsifier (HMDB: HMDB0006283)

Physical Properties

State

Solid

Experimental Molecular Properties

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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.00057 g/L	ALOGPS
logP	6.06	ALOGPS
logP	5.8	ChemAxon
logS	-5.8	ALOGPS
pKa (Strongest Acidic)	18.2	ChemAxon
pKa (Strongest Basic)	-0.26	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	122.3 m³·mol⁻¹	ChemAxon
Polarizability	51.1 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]+	199.913	31661259
DarkChem	[M-H]-	196.867	31661259
DeepCCS	[M-2H]-	232.143	30932474
DeepCCS	[M+Na]+	206.912	30932474
AllCCS	[M+H]+	206.1	32859911
AllCCS	[M+H-H2O]+	204.0	32859911
AllCCS	[M+NH4]+	208.0	32859911
AllCCS	[M+Na]+	208.5	32859911
AllCCS	[M-H]-	203.8	32859911
AllCCS	[M+Na-2H]-	205.8	32859911
AllCCS	[M+HCOO]-	208.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
20alpha-Hydroxycholesterol	CC(C)CCC[C@@](C)(O)[C@H]1CC[C@H]2[C@@H]3CC=C4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@]12C	2528.0	Standard polar	33892256
20alpha-Hydroxycholesterol	CC(C)CCC[C@@](C)(O)[C@H]1CC[C@H]2[C@@H]3CC=C4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@]12C	3245.6	Standard non polar	33892256
20alpha-Hydroxycholesterol	CC(C)CCC[C@@](C)(O)[C@H]1CC[C@H]2[C@@H]3CC=C4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@]12C	3315.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
20alpha-Hydroxycholesterol,1TMS,isomer #1	CC(C)CCC[C@@](C)(O[Si](C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC=C4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@@]21C	3323.7	Semi standard non polar	33892256
20alpha-Hydroxycholesterol,1TMS,isomer #2	CC(C)CCC[C@@](C)(O)[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	3336.0	Semi standard non polar	33892256
20alpha-Hydroxycholesterol,2TMS,isomer #1	CC(C)CCC[C@@](C)(O[Si](C)(C)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	3346.1	Semi standard non polar	33892256
20alpha-Hydroxycholesterol,1TBDMS,isomer #1	CC(C)CCC[C@@](C)(O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC=C4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@@]21C	3568.7	Semi standard non polar	33892256
20alpha-Hydroxycholesterol,1TBDMS,isomer #2	CC(C)CCC[C@@](C)(O)[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	3574.0	Semi standard non polar	33892256
20alpha-Hydroxycholesterol,2TBDMS,isomer #1	CC(C)CCC[C@@](C)(O[Si](C)(C)C(C)(C)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	3822.8	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 - 20alpha-Hydroxycholesterol GC-MS (Non-derivatized) - 70eV, Positive	splash10-007c-1139000000-2c00b5523723b960fa5a	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 20alpha-Hydroxycholesterol GC-MS (2 TMS) - 70eV, Positive	splash10-001i-3011490000-84aa9e3675270a653af2	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 20alpha-Hydroxycholesterol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 20alpha-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 - 20alpha-Hydroxycholesterol 10V, Positive-QTOF	splash10-0f79-0009200000-78634a50a076fbe30975	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20alpha-Hydroxycholesterol 20V, Positive-QTOF	splash10-05tr-3039100000-08dfa0b5e30063e9930a	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20alpha-Hydroxycholesterol 40V, Positive-QTOF	splash10-0avi-8189000000-c3bb06d3d099c9c4f440	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20alpha-Hydroxycholesterol 10V, Negative-QTOF	splash10-0udi-0003900000-4b881293f669607058cc	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20alpha-Hydroxycholesterol 20V, Negative-QTOF	splash10-0ue9-1039800000-4c4801e96fa5d9126da5	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20alpha-Hydroxycholesterol 40V, Negative-QTOF	splash10-059i-3089000000-806365cc5d181d0d25d9	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20alpha-Hydroxycholesterol 10V, Negative-QTOF	splash10-0udi-0000900000-079f76b4d985e4b92c9d	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20alpha-Hydroxycholesterol 20V, Negative-QTOF	splash10-0udi-0000900000-079f76b4d985e4b92c9d	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20alpha-Hydroxycholesterol 40V, Negative-QTOF	splash10-0udi-0009500000-63d3ce6872e526ad179d	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20alpha-Hydroxycholesterol 10V, Positive-QTOF	splash10-0f9i-0109100000-ba23251dfb42b1ea90e7	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20alpha-Hydroxycholesterol 20V, Positive-QTOF	splash10-0a4l-9147100000-ed7f14edc5be9509ea46	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20alpha-Hydroxycholesterol 40V, Positive-QTOF	splash10-0a4i-9820000000-1d6a2993646068927786	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane
Mitochondria

Biospecimen Locations

Not Available

Tissue Locations

Not Available

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

DB04704

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB023876

KNApSAcK ID

Not Available

Chemspider ID

389586

KEGG Compound ID

C05500

BioCyc ID

20A-HYDROXY-CHOLESTEROL

BiGG ID

1443018

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

440711

PDB ID

HC2

ChEBI ID

1296

Food Biomarker Ontology

Not Available

VMH ID

20AHCHSTEROL

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Mijares, A.; Cargill, David I.; Glasel, Jay A.; Lieberman, Seymour. C-20 epimers of 20-hydroxycholesterol. Journal of Organic Chemistry (1967), 32(3), 810-12.

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Sharma RK, Ahmed NK, Shanker G: Metabolic regulation of steroidogenesis in isolated adrenal cells of rat. Relationship of adrenocorticotropin-, adenosine 3':5'-monophosphate-and guanosine 3':5'-monophosphate-stimulated steroidogenesis with the activation of protein kinase. Eur J Biochem. 1976 Nov 15;70(2):427-33. [PubMed:188647 ]

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

Enzyme Details

2. Steroid 17-alpha-hydroxylase/17,20 lyase

General function:: Involved in monooxygenase activity
Specific function:: Conversion of pregnenolone and progesterone to their 17-alpha-hydroxylated products and subsequently to dehydroepiandrosterone (DHEA) and androstenedione. Catalyzes both the 17-alpha-hydroxylation and the 17,20-lyase reaction. Involved in sexual development during fetal life and at puberty.
Gene Name:: CYP17A1
Uniprot ID:: P05093
Molecular weight:: 57369.995

Reactions

20alpha-Hydroxycholesterol + NADPH + Hydrogen Ion + Oxygen → 17a,20a-Dihydroxycholesterol + NADP + Water	details

Showing metabocard for 20alpha-Hydroxycholesterol (HMDB0006283)

MOL for HMDB0006283 (20alpha-Hydroxycholesterol)

3D MOL for HMDB0006283 (20alpha-Hydroxycholesterol)

3D SDF for HMDB0006283 (20alpha-Hydroxycholesterol)

3D-SDF for HMDB0006283 (20alpha-Hydroxycholesterol)

PDB for HMDB0006283 (20alpha-Hydroxycholesterol)

3D PDB for HMDB0006283 (20alpha-Hydroxycholesterol)

SMILES for HMDB0006283 (20alpha-Hydroxycholesterol)

INCHI for HMDB0006283 (20alpha-Hydroxycholesterol)

Structure for HMDB0006283 (20alpha-Hydroxycholesterol)

3D Structure for HMDB0006283 (20alpha-Hydroxycholesterol)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

Reactions

Reactions