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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2022-03-07 02:49:08 UTC

HMDB ID

HMDB0001028

Secondary Accession Numbers

HMDB01028

Metabolite Identification

Common Name

25-Azacholesterol

Description

25-Azacholesterol has potent hypocholesterolemic activity. (PMID 14287266 ) It specifically inhibits cholesterol side-chain cleavage resulting in a decrease in steroid hormone production (PMID 5165491 ). Azasteroids may be membrane effectors which, in the case of mitochondria, lead to changes in adenosine triphosphate levels and(or) dehydrogenase activity. Their effects on sterol metabolism, therefore, may be of secondary consideration. (PMID 994744 ). 25-azacholesterol can induce a myotonic state in muscles. (PMID 5009506 ).

Structure

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

  Mrv0541 02231218522D          

 32 35  0  0  1  0            999 V2000
    8.7678   -8.3269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7678   -9.1519    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.4823   -9.5644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1967   -9.1519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1967   -8.3269    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.4823   -7.9144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9112   -9.5644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6257   -9.1519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6257   -8.3269    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.9112   -7.9144    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   12.3401   -7.9144    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   12.3401   -7.0894    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.6257   -6.6769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9112   -7.0894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1248   -8.1693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6098   -7.5019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1248   -6.8344    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   12.4264   -6.2689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3798   -6.0498    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   12.8278   -5.4367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1868   -5.8783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4417   -5.0937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2487   -4.9221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1967   -7.5019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4264   -8.7349    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.8465   -6.6827    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   15.5036   -4.1374    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.3105   -3.9658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0533   -9.5644    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.9175   -8.6213    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.6326   -7.5626    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   14.9514   -3.5244    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
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  1  1  0  0  0  0
  4  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10  5  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 10  1  0  0  0  0
 11 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 12  1  0  0  0  0
 12 18  1  1  0  0  0
 17 19  1  0  0  0  0
 19 20  1  6  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
  5 24  1  1  0  0  0
 11 25  1  6  0  0  0
 17 26  1  6  0  0  0
 27 23  1  0  0  0  0
 28 27  1  0  0  0  0
  2 29  1  1  0  0  0
 10 30  1  6  0  0  0
  9 31  1  1  0  0  0
 32 27  1  0  0  0  0
M  END

HMDB0001028
     RDKit          3D
25-Azacholesterol
 73 76  0  0  0  0  0  0  0  0999 V2000
    2.8344    0.9676   -1.5716 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6988    0.9081   -0.0743 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.9688    0.4395    0.6042 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1557    1.3107    0.3554 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3451    0.7234    1.0895 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6713   -0.5920    0.6687 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.1924   -0.7396   -0.6465 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1682   -1.4837    1.6591 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5668    0.0052    0.2936 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4480   -0.0766    1.8359 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0040   -0.3667    2.1255 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6426   -0.4546    0.7862 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1095   -0.1282    0.7790 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8353   -1.1327    1.6134 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0998   -1.6084    1.0246 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6716   -1.0932   -0.0550 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9464   -1.6136   -0.6059 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7676   -0.4693   -1.1268 C   0  0  1  0  0  0  0  0  0  0  0  0
   -7.1418    0.3032   -0.0146 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0128    0.2930   -2.1607 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5226    0.0453   -2.1665 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9989    0.0447   -0.7556 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.3460    1.3295   -0.0855 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5312   -0.2517   -0.6808 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7205    0.6296   -1.5672 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2319    0.3646   -1.4579 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1902    0.5244   -0.0387 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0419    1.9500    0.4019 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9056    0.8713   -1.8911 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4627    1.9104   -2.0183 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3319    0.1178   -2.0763 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4988    1.9628    0.2741 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7924    0.4194    1.6974 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1895   -0.5654    0.1822 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4085    1.5042   -0.6848 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9644    2.3040    0.8531 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1659    0.6997    2.1863 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2558    1.3603    0.9487 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7928   -1.6147   -1.2119 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2934   -0.9699   -0.5295 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0764    0.2175   -1.1928 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9760   -2.5538    1.4391 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2683   -1.3666    1.7280 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7436   -1.1745    2.6382 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6592   -1.0108   -0.0725 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7023    0.8888    2.3108 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1126   -0.8995    2.1840 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0887   -1.3596    2.6234 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4618    0.3817    2.7972 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5101   -1.4438    0.3195 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3210    0.8786    1.1919 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1019   -0.6425    2.5876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1423   -1.9861    1.8260 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6038   -2.4340    1.4988 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7533   -2.3846   -1.3896 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5002   -2.1127    0.2256 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7348   -0.8843   -1.5301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9039   -0.1328    0.8426 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3756   -0.0922   -3.1607 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2906    1.3557   -2.1573 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0602    0.9105   -2.6839 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3189   -0.8892   -2.6854 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0905    1.9498   -0.6332 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7224    1.1714    0.9439 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4600    2.0159    0.0163 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3603   -1.3004   -0.9806 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0063    0.4090   -2.6167 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8734    1.7027   -1.4092 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0577   -0.5976   -1.8885 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2328    1.1774   -2.0883 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3475    2.5726   -0.4927 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7115    2.2695    1.2059 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9684    2.2741    0.6434 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  2  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  1
 22 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  1
 27  9  1  0
 27 12  1  0
 24 13  1  0
 22 16  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  2 32  1  1
  3 33  1  0
  3 34  1  0
  4 35  1  0
  4 36  1  0
  5 37  1  0
  5 38  1  0
  7 39  1  0
  7 40  1  0
  7 41  1  0
  8 42  1  0
  8 43  1  0
  8 44  1  0
  9 45  1  6
 10 46  1  0
 10 47  1  0
 11 48  1  0
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 12 50  1  6
 13 51  1  1
 14 52  1  0
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 17 55  1  0
 17 56  1  0
 18 57  1  6
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 20 59  1  0
 20 60  1  0
 21 61  1  0
 21 62  1  0
 23 63  1  0
 23 64  1  0
 23 65  1  0
 24 66  1  6
 25 67  1  0
 25 68  1  0
 26 69  1  0
 26 70  1  0
 28 71  1  0
 28 72  1  0
 28 73  1  0
M  END

  Mrv0541 02231218522D          

 32 35  0  0  1  0            999 V2000
    8.7678   -8.3269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7678   -9.1519    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.4823   -9.5644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1967   -9.1519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1967   -8.3269    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.4823   -7.9144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9112   -9.5644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6257   -9.1519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6257   -8.3269    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.9112   -7.9144    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   12.3401   -7.9144    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   12.3401   -7.0894    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.6257   -6.6769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9112   -7.0894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1248   -8.1693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6098   -7.5019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1248   -6.8344    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   12.4264   -6.2689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3798   -6.0498    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   12.8278   -5.4367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1868   -5.8783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4417   -5.0937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2487   -4.9221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1967   -7.5019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4264   -8.7349    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.8465   -6.6827    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   15.5036   -4.1374    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.3105   -3.9658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0533   -9.5644    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.9175   -8.6213    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.6326   -7.5626    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   14.9514   -3.5244    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
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  1  1  0  0  0  0
  4  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10  5  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 10  1  0  0  0  0
 11 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 12  1  0  0  0  0
 12 18  1  1  0  0  0
 17 19  1  0  0  0  0
 19 20  1  6  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
  5 24  1  1  0  0  0
 11 25  1  6  0  0  0
 17 26  1  6  0  0  0
 27 23  1  0  0  0  0
 28 27  1  0  0  0  0
  2 29  1  1  0  0  0
 10 30  1  6  0  0  0
  9 31  1  1  0  0  0
 32 27  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0001028

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C26H45NO/c1-18(7-6-16-27(4)5)22-10-11-23-21-9-8-19-17-20(28)12-14-25(19,2)24(21)13-15-26(22,23)3/h8,18,20-24,28H,6-7,9-17H2,1-5H3/t18-,20+,21+,22-,23+,24+,25+,26-/m1/s1

> <INCHI_KEY>
RZPPEFJMRVRCDD-XSLNCIIRSA-N

> <FORMULA>
C26H45NO

> <MOLECULAR_WEIGHT>
387.6416

> <EXACT_MASS>
387.350115067

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
50.04316227847867

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
5.74

> <JCHEM_LOGP>
5.208800522000001

> <ALOGPS_LOGS>
-6.26

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.20428950550382

> <JCHEM_PKA_STRONGEST_BASIC>
9.78988893261288

> <JCHEM_POLAR_SURFACE_AREA>
23.47

> <JCHEM_REFRACTIVITY>
120.52139999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.15e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
25-azacholesterol

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0001028
     RDKit          3D
25-Azacholesterol
 73 76  0  0  0  0  0  0  0  0999 V2000
    2.8344    0.9676   -1.5716 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6988    0.9081   -0.0743 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.9688    0.4395    0.6042 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1557    1.3107    0.3554 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3451    0.7234    1.0895 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6713   -0.5920    0.6687 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.1924   -0.7396   -0.6465 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1682   -1.4837    1.6591 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5668    0.0052    0.2936 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4480   -0.0766    1.8359 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0040   -0.3667    2.1255 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6426   -0.4546    0.7862 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1095   -0.1282    0.7790 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8353   -1.1327    1.6134 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0998   -1.6084    1.0246 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6716   -1.0932   -0.0550 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9464   -1.6136   -0.6059 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7676   -0.4693   -1.1268 C   0  0  1  0  0  0  0  0  0  0  0  0
   -7.1418    0.3032   -0.0146 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0128    0.2930   -2.1607 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5226    0.0453   -2.1665 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9989    0.0447   -0.7556 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.3460    1.3295   -0.0855 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5312   -0.2517   -0.6808 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7205    0.6296   -1.5672 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2319    0.3646   -1.4579 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1902    0.5244   -0.0387 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0419    1.9500    0.4019 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9056    0.8713   -1.8911 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4627    1.9104   -2.0183 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3319    0.1178   -2.0763 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4988    1.9628    0.2741 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7924    0.4194    1.6974 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1895   -0.5654    0.1822 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4085    1.5042   -0.6848 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9644    2.3040    0.8531 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1659    0.6997    2.1863 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2558    1.3603    0.9487 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7928   -1.6147   -1.2119 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2934   -0.9699   -0.5295 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0764    0.2175   -1.1928 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9760   -2.5538    1.4391 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2683   -1.3666    1.7280 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7436   -1.1745    2.6382 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6592   -1.0108   -0.0725 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7023    0.8888    2.3108 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1126   -0.8995    2.1840 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0887   -1.3596    2.6234 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4618    0.3817    2.7972 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5101   -1.4438    0.3195 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3210    0.8786    1.1919 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1019   -0.6425    2.5876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1423   -1.9861    1.8260 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6038   -2.4340    1.4988 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7533   -2.3846   -1.3896 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5002   -2.1127    0.2256 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7348   -0.8843   -1.5301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9039   -0.1328    0.8426 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3756   -0.0922   -3.1607 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2906    1.3557   -2.1573 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0602    0.9105   -2.6839 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3189   -0.8892   -2.6854 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0905    1.9498   -0.6332 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7224    1.1714    0.9439 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4600    2.0159    0.0163 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3603   -1.3004   -0.9806 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0063    0.4090   -2.6167 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8734    1.7027   -1.4092 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0577   -0.5976   -1.8885 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2328    1.1774   -2.0883 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3475    2.5726   -0.4927 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7115    2.2695    1.2059 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9684    2.2741    0.6434 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  2  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  1
 22 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  1
 27  9  1  0
 27 12  1  0
 24 13  1  0
 22 16  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  2 32  1  1
  3 33  1  0
  3 34  1  0
  4 35  1  0
  4 36  1  0
  5 37  1  0
  5 38  1  0
  7 39  1  0
  7 40  1  0
  7 41  1  0
  8 42  1  0
  8 43  1  0
  8 44  1  0
  9 45  1  6
 10 46  1  0
 10 47  1  0
 11 48  1  0
 11 49  1  0
 12 50  1  6
 13 51  1  1
 14 52  1  0
 14 53  1  0
 15 54  1  0
 17 55  1  0
 17 56  1  0
 18 57  1  6
 19 58  1  0
 20 59  1  0
 20 60  1  0
 21 61  1  0
 21 62  1  0
 23 63  1  0
 23 64  1  0
 23 65  1  0
 24 66  1  6
 25 67  1  0
 25 68  1  0
 26 69  1  0
 26 70  1  0
 28 71  1  0
 28 72  1  0
 28 73  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      16.367 -15.544   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      16.367 -17.084   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      17.700 -17.854   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      19.034 -17.084   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      19.034 -15.544   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      17.700 -14.774   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      20.368 -17.854   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      21.701 -17.084   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      21.701 -15.544   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      20.368 -14.774   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      23.035 -14.774   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      23.035 -13.234   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      21.701 -12.464   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      20.368 -13.234   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      24.500 -15.249   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      25.405 -14.004   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      24.500 -12.758   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      23.196 -11.702   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      24.976 -11.293   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      23.945 -10.149   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      26.482 -10.973   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      26.958  -9.508   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      28.464  -9.188   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      19.034 -14.004   0.000  0.00  0.00           C+0
HETATM   25  H   UNK     0      23.196 -16.305   0.000  0.00  0.00           H+0
HETATM   26  H   UNK     0      25.847 -12.474   0.000  0.00  0.00           H+0
HETATM   27  N   UNK     0      28.940  -7.723   0.000  0.00  0.00           N+0
HETATM   28  C   UNK     0      30.446  -7.403   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      15.033 -17.854   0.000  0.00  0.00           O+0
HETATM   30  H   UNK     0      20.379 -16.093   0.000  0.00  0.00           H+0
HETATM   31  H   UNK     0      21.714 -14.117   0.000  0.00  0.00           H+0
HETATM   32  C   UNK     0      27.909  -6.579   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3   29                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    7                                                  
CONECT    5    4    6   10   24                                             
CONECT    6    5    1                                                       
CONECT    7    4    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11   31                                             
CONECT   10    9    5   14   30                                             
CONECT   11    9   12   15   25                                             
CONECT   12   11   13   17   18                                             
CONECT   13   12   14                                                       
CONECT   14   13   10                                                       
CONECT   15   11   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   12   19   26                                             
CONECT   18   12                                                            
CONECT   19   17   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   27                                                       
CONECT   24    5                                                            
CONECT   25   11                                                            
CONECT   26   17                                                            
CONECT   27   23   28   32                                                  
CONECT   28   27                                                            
CONECT   29    2                                                            
CONECT   30   10                                                            
CONECT   31    9                                                            
CONECT   32   27                                                            
MASTER        0    0    0    0    0    0    0    0   32    0   70    0
END

COMPND    HMDB0001028
HETATM    1  C1  UNL     1       2.834   0.968  -1.572  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.699   0.908  -0.074  1.00  0.00           C  
HETATM    3  C3  UNL     1       3.969   0.440   0.604  1.00  0.00           C  
HETATM    4  C4  UNL     1       5.156   1.311   0.355  1.00  0.00           C  
HETATM    5  C5  UNL     1       6.345   0.723   1.090  1.00  0.00           C  
HETATM    6  N1  UNL     1       6.671  -0.592   0.669  1.00  0.00           N  
HETATM    7  C6  UNL     1       7.192  -0.740  -0.646  1.00  0.00           C  
HETATM    8  C7  UNL     1       7.168  -1.484   1.659  1.00  0.00           C  
HETATM    9  C8  UNL     1       1.567   0.005   0.294  1.00  0.00           C  
HETATM   10  C9  UNL     1       1.448  -0.077   1.836  1.00  0.00           C  
HETATM   11  C10 UNL     1      -0.004  -0.367   2.125  1.00  0.00           C  
HETATM   12  C11 UNL     1      -0.643  -0.455   0.786  1.00  0.00           C  
HETATM   13  C12 UNL     1      -2.110  -0.128   0.779  1.00  0.00           C  
HETATM   14  C13 UNL     1      -2.835  -1.133   1.613  1.00  0.00           C  
HETATM   15  C14 UNL     1      -4.100  -1.608   1.025  1.00  0.00           C  
HETATM   16  C15 UNL     1      -4.672  -1.093  -0.055  1.00  0.00           C  
HETATM   17  C16 UNL     1      -5.946  -1.614  -0.606  1.00  0.00           C  
HETATM   18  C17 UNL     1      -6.768  -0.469  -1.127  1.00  0.00           C  
HETATM   19  O1  UNL     1      -7.142   0.303  -0.015  1.00  0.00           O  
HETATM   20  C18 UNL     1      -6.013   0.293  -2.161  1.00  0.00           C  
HETATM   21  C19 UNL     1      -4.523   0.045  -2.166  1.00  0.00           C  
HETATM   22  C20 UNL     1      -3.999   0.045  -0.756  1.00  0.00           C  
HETATM   23  C21 UNL     1      -4.346   1.330  -0.086  1.00  0.00           C  
HETATM   24  C22 UNL     1      -2.531  -0.252  -0.681  1.00  0.00           C  
HETATM   25  C23 UNL     1      -1.720   0.630  -1.567  1.00  0.00           C  
HETATM   26  C24 UNL     1      -0.232   0.365  -1.458  1.00  0.00           C  
HETATM   27  C25 UNL     1       0.190   0.524  -0.039  1.00  0.00           C  
HETATM   28  C26 UNL     1       0.042   1.950   0.402  1.00  0.00           C  
HETATM   29  H1  UNL     1       3.906   0.871  -1.891  1.00  0.00           H  
HETATM   30  H2  UNL     1       2.463   1.910  -2.018  1.00  0.00           H  
HETATM   31  H3  UNL     1       2.332   0.118  -2.076  1.00  0.00           H  
HETATM   32  H4  UNL     1       2.499   1.963   0.274  1.00  0.00           H  
HETATM   33  H5  UNL     1       3.792   0.419   1.697  1.00  0.00           H  
HETATM   34  H6  UNL     1       4.189  -0.565   0.182  1.00  0.00           H  
HETATM   35  H7  UNL     1       5.408   1.504  -0.685  1.00  0.00           H  
HETATM   36  H8  UNL     1       4.964   2.304   0.853  1.00  0.00           H  
HETATM   37  H9  UNL     1       6.166   0.700   2.186  1.00  0.00           H  
HETATM   38  H10 UNL     1       7.256   1.360   0.949  1.00  0.00           H  
HETATM   39  H11 UNL     1       6.793  -1.615  -1.212  1.00  0.00           H  
HETATM   40  H12 UNL     1       8.293  -0.970  -0.529  1.00  0.00           H  
HETATM   41  H13 UNL     1       7.076   0.217  -1.193  1.00  0.00           H  
HETATM   42  H14 UNL     1       6.976  -2.554   1.439  1.00  0.00           H  
HETATM   43  H15 UNL     1       8.268  -1.367   1.728  1.00  0.00           H  
HETATM   44  H16 UNL     1       6.744  -1.175   2.638  1.00  0.00           H  
HETATM   45  H17 UNL     1       1.659  -1.011  -0.073  1.00  0.00           H  
HETATM   46  H18 UNL     1       1.702   0.889   2.311  1.00  0.00           H  
HETATM   47  H19 UNL     1       2.113  -0.899   2.184  1.00  0.00           H  
HETATM   48  H20 UNL     1      -0.089  -1.360   2.623  1.00  0.00           H  
HETATM   49  H21 UNL     1      -0.462   0.382   2.797  1.00  0.00           H  
HETATM   50  H22 UNL     1      -0.510  -1.444   0.320  1.00  0.00           H  
HETATM   51  H23 UNL     1      -2.321   0.879   1.192  1.00  0.00           H  
HETATM   52  H24 UNL     1      -3.102  -0.642   2.588  1.00  0.00           H  
HETATM   53  H25 UNL     1      -2.142  -1.986   1.826  1.00  0.00           H  
HETATM   54  H26 UNL     1      -4.604  -2.434   1.499  1.00  0.00           H  
HETATM   55  H27 UNL     1      -5.753  -2.385  -1.390  1.00  0.00           H  
HETATM   56  H28 UNL     1      -6.500  -2.113   0.226  1.00  0.00           H  
HETATM   57  H29 UNL     1      -7.735  -0.884  -1.530  1.00  0.00           H  
HETATM   58  H30 UNL     1      -6.904  -0.133   0.843  1.00  0.00           H  
HETATM   59  H31 UNL     1      -6.376  -0.092  -3.161  1.00  0.00           H  
HETATM   60  H32 UNL     1      -6.291   1.356  -2.157  1.00  0.00           H  
HETATM   61  H33 UNL     1      -4.060   0.910  -2.684  1.00  0.00           H  
HETATM   62  H34 UNL     1      -4.319  -0.889  -2.685  1.00  0.00           H  
HETATM   63  H35 UNL     1      -5.090   1.950  -0.633  1.00  0.00           H  
HETATM   64  H36 UNL     1      -4.722   1.171   0.944  1.00  0.00           H  
HETATM   65  H37 UNL     1      -3.460   2.016   0.016  1.00  0.00           H  
HETATM   66  H38 UNL     1      -2.360  -1.300  -0.981  1.00  0.00           H  
HETATM   67  H39 UNL     1      -2.006   0.409  -2.617  1.00  0.00           H  
HETATM   68  H40 UNL     1      -1.873   1.703  -1.409  1.00  0.00           H  
HETATM   69  H41 UNL     1       0.058  -0.598  -1.888  1.00  0.00           H  
HETATM   70  H42 UNL     1       0.233   1.177  -2.088  1.00  0.00           H  
HETATM   71  H43 UNL     1       0.348   2.573  -0.493  1.00  0.00           H  
HETATM   72  H44 UNL     1       0.712   2.269   1.206  1.00  0.00           H  
HETATM   73  H45 UNL     1      -0.968   2.274   0.643  1.00  0.00           H  
CONECT    1    2   29   30   31
CONECT    2    3    9   32
CONECT    3    4   33   34
CONECT    4    5   35   36
CONECT    5    6   37   38
CONECT    6    7    8
CONECT    7   39   40   41
CONECT    8   42   43   44
CONECT    9   10   27   45
CONECT   10   11   46   47
CONECT   11   12   48   49
CONECT   12   13   27   50
CONECT   13   14   24   51
CONECT   14   15   52   53
CONECT   15   16   16   54
CONECT   16   17   22
CONECT   17   18   55   56
CONECT   18   19   20   57
CONECT   19   58
CONECT   20   21   59   60
CONECT   21   22   61   62
CONECT   22   23   24
CONECT   23   63   64   65
CONECT   24   25   66
CONECT   25   26   67   68
CONECT   26   27   69   70
CONECT   27   28
CONECT   28   71   72   73
END

HMDB0001028
     RDKit          3D
25-Azacholesterol
 73 76  0  0  0  0  0  0  0  0999 V2000
    2.8344    0.9676   -1.5716 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6988    0.9081   -0.0743 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.9688    0.4395    0.6042 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1557    1.3107    0.3554 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3451    0.7234    1.0895 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6713   -0.5920    0.6687 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.1924   -0.7396   -0.6465 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1682   -1.4837    1.6591 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5668    0.0052    0.2936 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4480   -0.0766    1.8359 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0040   -0.3667    2.1255 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6426   -0.4546    0.7862 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1095   -0.1282    0.7790 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8353   -1.1327    1.6134 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0998   -1.6084    1.0246 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6716   -1.0932   -0.0550 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9464   -1.6136   -0.6059 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7676   -0.4693   -1.1268 C   0  0  1  0  0  0  0  0  0  0  0  0
   -7.1418    0.3032   -0.0146 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0128    0.2930   -2.1607 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5226    0.0453   -2.1665 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9989    0.0447   -0.7556 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.3460    1.3295   -0.0855 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5312   -0.2517   -0.6808 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7205    0.6296   -1.5672 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2319    0.3646   -1.4579 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1902    0.5244   -0.0387 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0419    1.9500    0.4019 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9056    0.8713   -1.8911 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4627    1.9104   -2.0183 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3319    0.1178   -2.0763 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4988    1.9628    0.2741 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7924    0.4194    1.6974 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1895   -0.5654    0.1822 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4085    1.5042   -0.6848 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9644    2.3040    0.8531 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1659    0.6997    2.1863 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2558    1.3603    0.9487 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7928   -1.6147   -1.2119 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2934   -0.9699   -0.5295 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0764    0.2175   -1.1928 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9760   -2.5538    1.4391 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2683   -1.3666    1.7280 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7436   -1.1745    2.6382 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6592   -1.0108   -0.0725 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7023    0.8888    2.3108 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1126   -0.8995    2.1840 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0887   -1.3596    2.6234 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4618    0.3817    2.7972 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5101   -1.4438    0.3195 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3210    0.8786    1.1919 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1019   -0.6425    2.5876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1423   -1.9861    1.8260 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6038   -2.4340    1.4988 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7533   -2.3846   -1.3896 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5002   -2.1127    0.2256 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7348   -0.8843   -1.5301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9039   -0.1328    0.8426 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3756   -0.0922   -3.1607 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2906    1.3557   -2.1573 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0602    0.9105   -2.6839 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3189   -0.8892   -2.6854 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0905    1.9498   -0.6332 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7224    1.1714    0.9439 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4600    2.0159    0.0163 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3603   -1.3004   -0.9806 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0063    0.4090   -2.6167 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8734    1.7027   -1.4092 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0577   -0.5976   -1.8885 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2328    1.1774   -2.0883 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3475    2.5726   -0.4927 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7115    2.2695    1.2059 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9684    2.2741    0.6434 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  2  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  1
 22 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  1
 27  9  1  0
 27 12  1  0
 24 13  1  0
 22 16  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  2 32  1  1
  3 33  1  0
  3 34  1  0
  4 35  1  0
  4 36  1  0
  5 37  1  0
  5 38  1  0
  7 39  1  0
  7 40  1  0
  7 41  1  0
  8 42  1  0
  8 43  1  0
  8 44  1  0
  9 45  1  6
 10 46  1  0
 10 47  1  0
 11 48  1  0
 11 49  1  0
 12 50  1  6
 13 51  1  1
 14 52  1  0
 14 53  1  0
 15 54  1  0
 17 55  1  0
 17 56  1  0
 18 57  1  6
 19 58  1  0
 20 59  1  0
 20 60  1  0
 21 61  1  0
 21 62  1  0
 23 63  1  0
 23 64  1  0
 23 65  1  0
 24 66  1  6
 25 67  1  0
 25 68  1  0
 26 69  1  0
 26 70  1  0
 28 71  1  0
 28 72  1  0
 28 73  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(3beta)-24-(dimethylamino)-Chol-5-en-3-ol	HMDB
24-(dimethylamino)Chol-5-en-3beta-ol	HMDB
24-(dimethylamino)Chol-5-en-3 beta-ol	MeSH, HMDB

Chemical Formula

C₂₆H₄₅NO

Average Molecular Weight

387.6416

Monoisotopic Molecular Weight

387.350115067

IUPAC Name

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

Traditional Name

25-azacholesterol

CAS Registry Number

1973-61-1

SMILES

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

InChI Identifier

InChI=1S/C26H45NO/c1-18(7-6-16-27(4)5)22-10-11-23-21-9-8-19-17-20(28)12-14-25(19,2)24(21)13-15-26(22,23)3/h8,18,20-24,28H,6-7,9-17H2,1-5H3/t18-,20+,21+,22-,23+,24+,25+,26-/m1/s1

InChI Key

RZPPEFJMRVRCDD-XSLNCIIRSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 25-azasteroids and derivatives. These are azasteroids where the carbon atom at position 25 is replaced by a nitrogen atom.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Azasteroids and derivatives

Direct Parent

25-azasteroids and derivatives

Alternative Parents

Substituents

25-azasteroid
3-hydroxy-delta-5-steroid
3-hydroxysteroid
Hydroxysteroid
3-beta-hydroxy-delta-5-steroid
3-beta-hydroxysteroid
Delta-5-steroid
Cyclic alcohol
Tertiary aliphatic amine
Tertiary amine
Secondary alcohol
Organooxygen compound
Organonitrogen compound
Alcohol
Organic nitrogen compound
Amine
Hydrocarbon derivative
Organopnictogen compound
Organic oxygen compound
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

Cholesterol and derivatives (LMST01010212 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0001028)

Tissue

Nervous tissue

Hepatic tissue (HMDB: HMDB0001028)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0001028)

Source

Endogenous

Endogenous (HMDB: HMDB0001028)

Animal

Animal (HMDB: HMDB0001028)

Exogenous

Food

Food (HMDB: HMDB0001028)

Animal origin

Poultry

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)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

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)

Equine

Horse (FooDB: FOOD00378)

Exogenous (HMDB: HMDB0001028)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0001028)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0001028)

Lipid metabolism pathway (HMDB: HMDB0001028)

Cellular process

Cell signaling (HMDB: HMDB0001028)

Biochemical process

Lipid transport (HMDB: HMDB0001028)

Role

Biological role

Membrane stabilizer (HMDB: HMDB0001028)

Molecular messenger

Hormone (HMDB: HMDB0001028)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0001028)

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	0.00022 g/L	ALOGPS
logP	5.74	ALOGPS
logP	5.21	ChemAxon
logS	-6.3	ALOGPS
pKa (Strongest Acidic)	18.2	ChemAxon
pKa (Strongest Basic)	9.79	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	23.47 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	120.52 m³·mol⁻¹	ChemAxon
Polarizability	50.04 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	195.993	31661259
DarkChem	[M-H]-	193.213	31661259
AllCCS	[M+H]+	202.887	32859911
AllCCS	[M-H]-	199.413	32859911
DeepCCS	[M-2H]-	233.63	30932474
DeepCCS	[M+Na]+	207.9	30932474
AllCCS	[M+H]+	202.9	32859911
AllCCS	[M+H-H2O]+	200.8	32859911
AllCCS	[M+NH4]+	204.8	32859911
AllCCS	[M+Na]+	205.4	32859911
AllCCS	[M-H]-	199.4	32859911
AllCCS	[M+Na-2H]-	201.1	32859911
AllCCS	[M+HCOO]-	203.2	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
25-Azacholesterol	[H][C@@]1(CC[C@@]2([H])[C@]3([H])CC=C4C[C@@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCCN(C)C	2379.5	Standard polar	33892256
25-Azacholesterol	[H][C@@]1(CC[C@@]2([H])[C@]3([H])CC=C4C[C@@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCCN(C)C	3104.3	Standard non polar	33892256
25-Azacholesterol	[H][C@@]1(CC[C@@]2([H])[C@]3([H])CC=C4C[C@@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCCN(C)C	3167.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
25-Azacholesterol,1TMS,isomer #1	C[C@H](CCCN(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	3217.1	Semi standard non polar	33892256
25-Azacholesterol,1TBDMS,isomer #1	C[C@H](CCCN(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	3448.0	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 - 25-Azacholesterol GC-MS (Non-derivatized) - 70eV, Positive	splash10-0ab9-1109000000-f5ff026e303e1f936133	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 25-Azacholesterol GC-MS (1 TMS) - 70eV, Positive	splash10-0537-5104900000-019f268d7a583a080fb4	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 25-Azacholesterol 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 - 25-Azacholesterol 10V, Positive-QTOF	splash10-00dr-0009000000-f51472900bc87c0a5f52	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 25-Azacholesterol 20V, Positive-QTOF	splash10-009l-1029000000-ce2f5ffd6b9bbae51f14	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 25-Azacholesterol 40V, Positive-QTOF	splash10-0pb9-5289000000-31a238e0014232ddab59	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 25-Azacholesterol 10V, Negative-QTOF	splash10-000i-0009000000-74f294bbd7bfc4e4a2ac	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 25-Azacholesterol 20V, Negative-QTOF	splash10-000i-0009000000-72958248b3206fa61b1c	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 25-Azacholesterol 40V, Negative-QTOF	splash10-004l-2009000000-1a9f32b77ddd2fc5611b	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 25-Azacholesterol 10V, Positive-QTOF	splash10-000i-0009000000-d3af83736c6337f4138c	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 25-Azacholesterol 20V, Positive-QTOF	splash10-0a4v-7279000000-1c3cb8189566196cb292	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 25-Azacholesterol 40V, Positive-QTOF	splash10-0a4i-9810000000-8eb0011e2f4a452bc336	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 25-Azacholesterol 10V, Negative-QTOF	splash10-000i-0009000000-37d8acdc244819d61e09	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 25-Azacholesterol 20V, Negative-QTOF	splash10-000i-0009000000-5ff1c6d45a64ff5f57af	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 25-Azacholesterol 40V, Negative-QTOF	splash10-001i-0009000000-eb7f6fb387795c01b9db	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane (predicted from logP)

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022378

KNApSAcK ID

Not Available

Chemspider ID

144573

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

5954

PubChem Compound

164906

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

COUNSELL RE, KLIMSTRA PD, NYSTED LN, RANNEY RE: HYPOCHOLESTEROLEMIC AGENTS. V. ISOMERIC AZACHOLESTEROLS. J Med Chem. 1965 Jan;8:45-8. [PubMed:14287266 ]
Counsell RE, Lu MC, el-Masry S, Weinhold PA: Inhibition of cholesterol side-chain cleavage by azacholesterols. Biochem Pharmacol. 1971 Oct;20(10):2912-5. [PubMed:5165491 ]
Kabara JJ, Holzschu DL, Catsoulacos DP: Structure-function activity of azasterols and nitrogen-containing steroids. Lipids. 1976 Oct;11(10):755-62. [PubMed:994744 ]
Eberstein A, Goodgold J: Isotonic contraction of induced myotonic muscle of rat: after contraction and prolonged relaxation time. Exp Neurol. 1972 Jan;34(1):183-6. [PubMed:5009506 ]

Showing metabocard for 25-Azacholesterol (HMDB0001028)

MOL for HMDB0001028 (25-Azacholesterol)

3D MOL for HMDB0001028 (25-Azacholesterol)

3D SDF for HMDB0001028 (25-Azacholesterol)

3D-SDF for HMDB0001028 (25-Azacholesterol)

PDB for HMDB0001028 (25-Azacholesterol)

3D PDB for HMDB0001028 (25-Azacholesterol)

SMILES for HMDB0001028 (25-Azacholesterol)

INCHI for HMDB0001028 (25-Azacholesterol)

Structure for HMDB0001028 (25-Azacholesterol)

3D Structure for HMDB0001028 (25-Azacholesterol)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra