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Showing metabocard for 20alpha-Hydroxycholesterol (HMDB0006283)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesenzymes (2) Show 2 proteinsXML
enzymes (2) Show 2 proteins
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2007-05-22 21:16:34 UTC
Update Date2021-09-16 15:27:37 UTC
HMDB IDHMDB0006283
Secondary Accession Numbers
  • HMDB06283
Metabolite Identification
Common Name20alpha-Hydroxycholesterol
Description20alpha-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
Data?1582752379
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0006283 (20alpha-Hydroxycholesterol)


  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
Download

3D MOL for HMDB0006283 (20alpha-Hydroxycholesterol)

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
Download

3D SDF for HMDB0006283 (20alpha-Hydroxycholesterol)


  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

$$$$
Download

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

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
Download

PDB for HMDB0006283 (20alpha-Hydroxycholesterol)

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
Download

3D PDB for HMDB0006283 (20alpha-Hydroxycholesterol)

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
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SMILES for HMDB0006283 (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
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INCHI for HMDB0006283 (20alpha-Hydroxycholesterol)

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
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View in JSmolView Stereo Labels
Synonyms
ValueSource
20a-HydroxycholesterolGenerator
20Α-hydroxycholesterolGenerator
(20S)-20-HydroxycholesterolMeSH
(20S)-Cholest-5-ene-3 beta,20-diolMeSH
20 alpha-HydroxycholesterolMeSH
20-HydroxycholesterolMeSH
20-Hydroxycholesterol, (3beta,20 xi)-isomerMeSH
20-Hydroxycholesterol, 3H-labeled, (3beta,20 xi)-isomerMeSH
20R-HydroxycholesterolMeSH
(3beta,20R)-Cholest-5-ene-3,20-diolHMDB
20alpha-Hydroxy cholesterolHMDB
Chemical FormulaC27H46O2
Average Molecular Weight402.6529
Monoisotopic Molecular Weight402.349780716
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 Name20a-hydroxy cholesterol
CAS Registry Number516-72-3
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 KeyMCKLJFJEQRYRQT-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.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassCholestane steroids
Direct ParentCholesterols 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 FrameworkAliphatic homopolycyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Source

Route of exposure

Process

Naturally occurring process

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Spectral PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.00057 g/LALOGPS
logP10(6.06) g/LALOGPS
logP10(5.8) g/LChemAxon
logS10(-5.8) g/LALOGPS
pKa (Strongest Acidic)18.2ChemAxon
pKa (Strongest Basic)-0.26ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area40.46 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity122.3 m³·mol⁻¹ChemAxon
Polarizability51.1 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Spectral Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+199.91331661259
DarkChem[M-H]-196.86731661259

Predicted Kovats Retention Indices

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
20alpha-Hydroxycholesterol,1TMS,#1CC(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@@]21C3323.7Semi standard non polarhttps://arxiv.org/abs/1905.12712
20alpha-Hydroxycholesterol,1TMS,#2CC(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@@]21C3336.0Semi standard non polarhttps://arxiv.org/abs/1905.12712
20alpha-Hydroxycholesterol,2TMS,#1CC(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@@]21C3346.1Semi standard non polarhttps://arxiv.org/abs/1905.12712
20alpha-Hydroxycholesterol,1TBDMS,#1CC(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@@]21C3568.7Semi standard non polarhttps://arxiv.org/abs/1905.12712
20alpha-Hydroxycholesterol,1TBDMS,#2CC(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@@]21C3574.0Semi standard non polarhttps://arxiv.org/abs/1905.12712
20alpha-Hydroxycholesterol,2TBDMS,#1CC(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@@]21C3822.8Semi standard non polarhttps://arxiv.org/abs/1905.12712
Spectra
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
  • Mitochondria
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB04704
Phenol Explorer Compound IDNot Available
FooDB IDFDB023876
KNApSAcK IDNot Available
Chemspider ID389586
KEGG Compound IDC05500
BioCyc ID20A-HYDROXY-CHOLESTEROL
BiGG ID1443018
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound440711
PDB IDHC2
ChEBI ID1296
Food Biomarker OntologyNot Available
VMH ID20AHCHSTEROL
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceMijares, 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
  1. 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 ferredoxindetails
20alpha-Hydroxycholesterol + Oxygen + Reduced adrenal ferredoxin + Hydrogen Ion → 20a,22b-Dihydroxycholesterol + Water + Oxidized adrenal ferredoxindetails
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 + Waterdetails