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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2006-05-22 15:12:05 UTC

Update Date

2022-03-07 02:49:16 UTC

HMDB ID

HMDB0002719

Secondary Accession Numbers

HMDB02719

Metabolite Identification

Common Name

Desmosterol

Description

Desmosterol is an intermediate in the synthesis of cholesterol. Desmosterolosis is a rare autosomal recessive inborn errors of cholesterol synthesis that is caused by defective activity of desmosterol reductase which results in an accumulation of demosterol (DHCR24, EC 1.3.1.72), combines a severe osteosclerotic skeletal dysplasia and includes 2-3 toe syndactyly with Smith-Lemli-Opitz syndrome (SLOS; the biochemical block in SLOS results in decreased cholesterol levels and increased 7-dehydrocholesterol levels). Desmosterolosis is caused by mutation of the 24-dehydrocholesterol reductase gene (DHCR24). Many of the malformations in SLOS and desmosterolosis are consistent with impaired hedgehog function. The hedgehog proteins include Sonic hedgehog (SHH), which plays a major role in midline patterning and limb development. Desmosterolosis, caused by defective activity of desmosterol reductase, combines a severe osteosclerotic skeletal dysplasia. 7-dehydrocholesterol reductase (DHCR7, EC 1.3.1.21) reduces the C7-C8 double bond in the sterol B ring to form cholesterol or desmosterol depending upon the precursor. Desmosterol can be converted to cholesterol by DHCR24. Therefore, SLOS and Desmosterolosis patients invariably have elevated levels of cholesterol precursor's 7-dehydrocholesterol (and its spontaneous isomer 8-dehydrocholesterol) and absent desmosterol. (PMID: 14631207 , 16207203 ).

Structure

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

  Mrv1652309042000272D          

 32 35  0  0  0  0            999 V2000
 9999.976210001.2192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.8391 9999.9734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.6978 9997.9037    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.2638 9999.9734    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9998.5515 9998.7390    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9999.9762 9998.7390    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9997.1253 9999.5578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.4108 9999.1453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.4108 9998.3202    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9997.1253 9997.9078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.8398 9998.3202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.8398 9999.1453    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9999.264210000.8031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.549710000.3906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.5497 9999.5655    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9999.2642 9999.1531    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9998.5515 9997.9078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.2660 9998.3202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.978710000.3905    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9999.9787 9999.5656    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10000.7633 9999.3106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.2482 9999.9780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.763310000.6455    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10000.763310001.4705    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10001.479010001.8810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.049710001.8810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.192610001.4705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.908310001.8810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.624010001.4705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.337610001.8810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.624010000.6455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.479010001.0560    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  7  8  1  0  0  0  0
  7 12  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 17 18  1  0  0  0  0
 15  5  1  6  0  0  0
 18 16  1  0  0  0  0
 16  4  1  1  0  0  0
  9  3  1  1  0  0  0
 12  2  1  1  0  0  0
 15 12  1  0  0  0  0
 11 17  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 23 24  1  0  0  0  0
 23 32  1  6  0  0  0
 24 25  1  0  0  0  0
 24 26  1  6  0  0  0
 25 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 29 30  1  0  0  0  0
 29 31  1  0  0  0  0
 23 19  1  0  0  0  0
 23 22  1  0  0  0  0
 16 20  1  0  0  0  0
 20  6  1  6  0  0  0
 13 19  1  0  0  0  0
 19  1  1  1  0  0  0
M  END

HMDB0002719
     RDKit          3D
Desmosterol
 72 75  0  0  0  0  0  0  0  0999 V2000
    7.1713   -0.6271    0.9787 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5413   -1.6127    0.0920 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0770   -3.0185    0.0687 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5223   -1.3610   -0.7027 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9446    0.0069   -0.7287 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4760   -0.0424   -0.3181 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9354    1.3597   -0.3581 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0309    1.9736   -1.7368 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6455    1.5425    0.3251 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2128    2.9903    0.2271 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2725    2.9288   -0.1644 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6447    1.6067    0.3902 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9473    1.0327   -0.0612 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0817    1.9940    0.0758 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3297    1.3102   -0.3170 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5199    0.0346   -0.0899 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7956   -0.5962   -0.5057 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4231   -1.1177    0.7757 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.9060   -2.4180    0.6523 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5915   -0.8855    1.9919 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1548   -1.2497    1.8965 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5126   -0.8228    0.5729 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.3491   -2.1204   -0.2085 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1943   -0.1765    0.8135 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0477   -1.1383    0.6205 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3055   -0.5518    0.7141 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4909    0.7103   -0.0937 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3195    0.4420   -1.5306 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4308   -0.3535    1.7859 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4792    0.3116    0.4536 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0228   -1.0927    1.5110 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9891   -3.0970    0.6732 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2647   -3.7028    0.3731 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2618   -3.2345   -1.0173 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0671   -2.0966   -1.3516 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5323    0.6438   -0.0525 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0612    0.4698   -1.7470 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9387   -0.7940   -0.8719 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4741   -0.3522    0.7587 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6863    1.9443    0.2665 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0635    2.4581   -2.0636 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7860    2.7832   -1.8160 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3469    1.2182   -2.5166 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8162    1.3358    1.4236 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8083    3.6126   -0.4300 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2107    3.4883    1.2228 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8557    3.7263    0.3639 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4295    3.0808   -1.2279 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6224    1.6445    1.4805 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9477    0.6661   -1.1104 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8535    2.8635   -0.5974 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1839    2.4028    1.1063 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1142    1.8993   -0.8134 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6523   -1.4070   -1.2592 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4299    0.1544   -1.0198 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3561   -0.4916    0.9184 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8466   -2.4584    0.3754 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0369   -1.5364    2.8022 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7501    0.1605    2.3894 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9998   -2.3075    2.1149 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6119   -0.6834    2.7080 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0002   -1.9816   -1.2286 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7506   -2.8206    0.4161 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3472   -2.6258   -0.2914 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1353    0.1963    1.8745 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1393   -1.9007    1.4504 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2103   -1.7288   -0.3100 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0441   -1.3322    0.4962 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4824   -0.2570    1.7900 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3414   -0.4690   -1.6422 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2509    1.2398   -2.0797 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1969    0.2296   -2.1337 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 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  6
 22 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  6
 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
  3 32  1  0
  3 33  1  0
  3 34  1  0
  4 35  1  0
  5 36  1  0
  5 37  1  0
  6 38  1  0
  6 39  1  0
  7 40  1  1
  8 41  1  0
  8 42  1  0
  8 43  1  0
  9 44  1  1
 10 45  1  0
 10 46  1  0
 11 47  1  0
 11 48  1  0
 12 49  1  1
 13 50  1  6
 14 51  1  0
 14 52  1  0
 15 53  1  0
 17 54  1  0
 17 55  1  0
 18 56  1  1
 19 57  1  0
 20 58  1  0
 20 59  1  0
 21 60  1  0
 21 61  1  0
 23 62  1  0
 23 63  1  0
 23 64  1  0
 24 65  1  1
 25 66  1  0
 25 67  1  0
 26 68  1  0
 26 69  1  0
 28 70  1  0
 28 71  1  0
 28 72  1  0
M  END

  Mrv1652309042000272D          

 32 35  0  0  0  0            999 V2000
 9999.976210001.2192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.8391 9999.9734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.6978 9997.9037    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.2638 9999.9734    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9998.5515 9998.7390    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9999.9762 9998.7390    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9997.1253 9999.5578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.4108 9999.1453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.4108 9998.3202    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9997.1253 9997.9078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.8398 9998.3202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.8398 9999.1453    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9999.264210000.8031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.549710000.3906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.5497 9999.5655    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9999.2642 9999.1531    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9998.5515 9997.9078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.2660 9998.3202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.978710000.3905    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9999.9787 9999.5656    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10000.7633 9999.3106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.2482 9999.9780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.763310000.6455    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10000.763310001.4705    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10001.479010001.8810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.049710001.8810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.192610001.4705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.908310001.8810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.624010001.4705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.337610001.8810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.624010000.6455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.479010001.0560    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  7  8  1  0  0  0  0
  7 12  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 17 18  1  0  0  0  0
 15  5  1  6  0  0  0
 18 16  1  0  0  0  0
 16  4  1  1  0  0  0
  9  3  1  1  0  0  0
 12  2  1  1  0  0  0
 15 12  1  0  0  0  0
 11 17  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 23 24  1  0  0  0  0
 23 32  1  6  0  0  0
 24 25  1  0  0  0  0
 24 26  1  6  0  0  0
 25 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 29 30  1  0  0  0  0
 29 31  1  0  0  0  0
 23 19  1  0  0  0  0
 23 22  1  0  0  0  0
 16 20  1  0  0  0  0
 20  6  1  6  0  0  0
 13 19  1  0  0  0  0
 19  1  1  1  0  0  0
M  END
> <DATABASE_ID>
HMDB0002719

> <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)CCC=C(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C27H44O/c1-18(2)7-6-8-19(3)23-11-12-24-22-10-9-20-17-21(28)13-15-26(20,4)25(22)14-16-27(23,24)5/h7,9,19,21-25,28H,6,8,10-17H2,1-5H3/t19-,21+,22+,23-,24+,25+,26+,27-/m1/s1

> <INCHI_KEY>
AVSXSVCZWQODGV-DPAQBDIFSA-N

> <FORMULA>
C27H44O

> <MOLECULAR_WEIGHT>
384.6377

> <EXACT_MASS>
384.33921603

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
72

> <JCHEM_AVERAGE_POLARIZABILITY>
49.66598287203385

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
6.62

> <JCHEM_LOGP>
6.707309549333335

> <ALOGPS_LOGS>
-6.53

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.20428950550382

> <JCHEM_PKA_STRONGEST_BASIC>
-1.3972437702926293

> <JCHEM_POLAR_SURFACE_AREA>
20.23

> <JCHEM_REFRACTIVITY>
121.46649999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.14e-04 g/l

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

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0002719
     RDKit          3D
Desmosterol
 72 75  0  0  0  0  0  0  0  0999 V2000
    7.1713   -0.6271    0.9787 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5413   -1.6127    0.0920 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0770   -3.0185    0.0687 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5223   -1.3610   -0.7027 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9446    0.0069   -0.7287 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4760   -0.0424   -0.3181 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9354    1.3597   -0.3581 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0309    1.9736   -1.7368 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6455    1.5425    0.3251 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2128    2.9903    0.2271 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2725    2.9288   -0.1644 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6447    1.6067    0.3902 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9473    1.0327   -0.0612 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0817    1.9940    0.0758 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3297    1.3102   -0.3170 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5199    0.0346   -0.0899 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7956   -0.5962   -0.5057 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4231   -1.1177    0.7757 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.9060   -2.4180    0.6523 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5915   -0.8855    1.9919 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1548   -1.2497    1.8965 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5126   -0.8228    0.5729 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.3491   -2.1204   -0.2085 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1943   -0.1765    0.8135 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0477   -1.1383    0.6205 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3055   -0.5518    0.7141 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4909    0.7103   -0.0937 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3195    0.4420   -1.5306 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4308   -0.3535    1.7859 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4792    0.3116    0.4536 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0228   -1.0927    1.5110 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9891   -3.0970    0.6732 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2647   -3.7028    0.3731 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2618   -3.2345   -1.0173 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0671   -2.0966   -1.3516 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5323    0.6438   -0.0525 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0612    0.4698   -1.7470 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9387   -0.7940   -0.8719 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4741   -0.3522    0.7587 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6863    1.9443    0.2665 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0635    2.4581   -2.0636 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7860    2.7832   -1.8160 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3469    1.2182   -2.5166 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8162    1.3358    1.4236 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8083    3.6126   -0.4300 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2107    3.4883    1.2228 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8557    3.7263    0.3639 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4295    3.0808   -1.2279 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6224    1.6445    1.4805 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9477    0.6661   -1.1104 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8535    2.8635   -0.5974 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1839    2.4028    1.1063 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1142    1.8993   -0.8134 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6523   -1.4070   -1.2592 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4299    0.1544   -1.0198 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3561   -0.4916    0.9184 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8466   -2.4584    0.3754 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0369   -1.5364    2.8022 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7501    0.1605    2.3894 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9998   -2.3075    2.1149 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6119   -0.6834    2.7080 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0002   -1.9816   -1.2286 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7506   -2.8206    0.4161 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3472   -2.6258   -0.2914 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1353    0.1963    1.8745 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1393   -1.9007    1.4504 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2103   -1.7288   -0.3100 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0441   -1.3322    0.4962 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4824   -0.2570    1.7900 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3414   -0.4690   -1.6422 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2509    1.2398   -2.0797 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1969    0.2296   -2.1337 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 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  6
 22 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  6
 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
  3 32  1  0
  3 33  1  0
  3 34  1  0
  4 35  1  0
  5 36  1  0
  5 37  1  0
  6 38  1  0
  6 39  1  0
  7 40  1  1
  8 41  1  0
  8 42  1  0
  8 43  1  0
  9 44  1  1
 10 45  1  0
 10 46  1  0
 11 47  1  0
 11 48  1  0
 12 49  1  1
 13 50  1  6
 14 51  1  0
 14 52  1  0
 15 53  1  0
 17 54  1  0
 17 55  1  0
 18 56  1  1
 19 57  1  0
 20 58  1  0
 20 59  1  0
 21 60  1  0
 21 61  1  0
 23 62  1  0
 23 63  1  0
 23 64  1  0
 24 65  1  1
 25 66  1  0
 25 67  1  0
 26 68  1  0
 26 69  1  0
 28 70  1  0
 28 71  1  0
 28 72  1  0
M  END

HEADER    PROTEIN                                 04-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-20         0                                  
HETATM    1  C   UNK     0    8666.6228668.943   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8662.6338666.617   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0    8658.6368662.754   0.000  0.00  0.00           O+0
HETATM    4  H   UNK     0    8665.2928666.617   0.000  0.00  0.00           H+0
HETATM    5  H   UNK     0    8663.9638664.313   0.000  0.00  0.00           H+0
HETATM    6  H   UNK     0    8666.6228664.313   0.000  0.00  0.00           H+0
HETATM    7  C   UNK     0    8661.3018665.841   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8659.9678665.071   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8659.9678663.531   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8661.3018662.761   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8662.6348663.531   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8662.6348665.071   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8665.2938668.166   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8663.9598667.396   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8663.9598665.856   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8665.2938665.086   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8663.9638662.761   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    8665.2978663.531   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0    8666.6278667.396   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0    8666.6278665.856   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0    8668.0918665.380   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0    8668.9978666.626   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0    8668.0918667.872   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0    8668.0918669.412   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0    8669.4278670.178   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0    8666.7598670.178   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0    8670.7608669.412   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0    8672.0958670.178   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0    8673.4318669.412   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0    8674.7648670.178   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0    8673.4318667.872   0.000  0.00  0.00           C+0
HETATM   32  H   UNK     0    8669.4278668.638   0.000  0.00  0.00           H+0
CONECT    1   19                                                            
CONECT    2   12                                                            
CONECT    3    9                                                            
CONECT    4   16                                                            
CONECT    5   15                                                            
CONECT    6   20                                                            
CONECT    7    8   12                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10    3                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   17                                                  
CONECT   12    7   11    2   15                                             
CONECT   13   14   19                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16    5   12                                             
CONECT   16   15   18    4   20                                             
CONECT   17   18   11                                                       
CONECT   18   17   16                                                       
CONECT   19   20   23   13    1                                             
CONECT   20   19   21   16    6                                             
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   24   32   19   22                                             
CONECT   24   23   25   26                                                  
CONECT   25   24   27                                                       
CONECT   26   24                                                            
CONECT   27   25   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29                                                            
CONECT   32   23                                                            
MASTER        0    0    0    0    0    0    0    0   32    0   70    0
END

COMPND    HMDB0002719
HETATM    1  C1  UNL     1       7.171  -0.627   0.979  1.00  0.00           C  
HETATM    2  C2  UNL     1       6.541  -1.613   0.092  1.00  0.00           C  
HETATM    3  C3  UNL     1       7.077  -3.019   0.069  1.00  0.00           C  
HETATM    4  C4  UNL     1       5.522  -1.361  -0.703  1.00  0.00           C  
HETATM    5  C5  UNL     1       4.945   0.007  -0.729  1.00  0.00           C  
HETATM    6  C6  UNL     1       3.476  -0.042  -0.318  1.00  0.00           C  
HETATM    7  C7  UNL     1       2.935   1.360  -0.358  1.00  0.00           C  
HETATM    8  C8  UNL     1       3.031   1.974  -1.737  1.00  0.00           C  
HETATM    9  C9  UNL     1       1.646   1.542   0.325  1.00  0.00           C  
HETATM   10  C10 UNL     1       1.213   2.990   0.227  1.00  0.00           C  
HETATM   11  C11 UNL     1      -0.272   2.929  -0.164  1.00  0.00           C  
HETATM   12  C12 UNL     1      -0.645   1.607   0.390  1.00  0.00           C  
HETATM   13  C13 UNL     1      -1.947   1.033  -0.061  1.00  0.00           C  
HETATM   14  C14 UNL     1      -3.082   1.994   0.076  1.00  0.00           C  
HETATM   15  C15 UNL     1      -4.330   1.310  -0.317  1.00  0.00           C  
HETATM   16  C16 UNL     1      -4.520   0.035  -0.090  1.00  0.00           C  
HETATM   17  C17 UNL     1      -5.796  -0.596  -0.506  1.00  0.00           C  
HETATM   18  C18 UNL     1      -6.423  -1.118   0.776  1.00  0.00           C  
HETATM   19  O1  UNL     1      -6.906  -2.418   0.652  1.00  0.00           O  
HETATM   20  C19 UNL     1      -5.591  -0.886   1.992  1.00  0.00           C  
HETATM   21  C20 UNL     1      -4.155  -1.250   1.896  1.00  0.00           C  
HETATM   22  C21 UNL     1      -3.513  -0.823   0.573  1.00  0.00           C  
HETATM   23  C22 UNL     1      -3.349  -2.120  -0.209  1.00  0.00           C  
HETATM   24  C23 UNL     1      -2.194  -0.176   0.813  1.00  0.00           C  
HETATM   25  C24 UNL     1      -1.048  -1.138   0.620  1.00  0.00           C  
HETATM   26  C25 UNL     1       0.306  -0.552   0.714  1.00  0.00           C  
HETATM   27  C26 UNL     1       0.491   0.710  -0.094  1.00  0.00           C  
HETATM   28  C27 UNL     1       0.319   0.442  -1.531  1.00  0.00           C  
HETATM   29  H1  UNL     1       6.431  -0.353   1.786  1.00  0.00           H  
HETATM   30  H2  UNL     1       7.479   0.312   0.454  1.00  0.00           H  
HETATM   31  H3  UNL     1       8.023  -1.093   1.511  1.00  0.00           H  
HETATM   32  H4  UNL     1       7.989  -3.097   0.673  1.00  0.00           H  
HETATM   33  H5  UNL     1       6.265  -3.703   0.373  1.00  0.00           H  
HETATM   34  H6  UNL     1       7.262  -3.235  -1.017  1.00  0.00           H  
HETATM   35  H7  UNL     1       5.067  -2.097  -1.352  1.00  0.00           H  
HETATM   36  H8  UNL     1       5.532   0.644  -0.052  1.00  0.00           H  
HETATM   37  H9  UNL     1       5.061   0.470  -1.747  1.00  0.00           H  
HETATM   38  H10 UNL     1       2.939  -0.794  -0.872  1.00  0.00           H  
HETATM   39  H11 UNL     1       3.474  -0.352   0.759  1.00  0.00           H  
HETATM   40  H12 UNL     1       3.686   1.944   0.266  1.00  0.00           H  
HETATM   41  H13 UNL     1       2.063   2.458  -2.064  1.00  0.00           H  
HETATM   42  H14 UNL     1       3.786   2.783  -1.816  1.00  0.00           H  
HETATM   43  H15 UNL     1       3.347   1.218  -2.517  1.00  0.00           H  
HETATM   44  H16 UNL     1       1.816   1.336   1.424  1.00  0.00           H  
HETATM   45  H17 UNL     1       1.808   3.613  -0.430  1.00  0.00           H  
HETATM   46  H18 UNL     1       1.211   3.488   1.223  1.00  0.00           H  
HETATM   47  H19 UNL     1      -0.856   3.726   0.364  1.00  0.00           H  
HETATM   48  H20 UNL     1      -0.429   3.081  -1.228  1.00  0.00           H  
HETATM   49  H21 UNL     1      -0.622   1.644   1.481  1.00  0.00           H  
HETATM   50  H22 UNL     1      -1.948   0.666  -1.110  1.00  0.00           H  
HETATM   51  H23 UNL     1      -2.853   2.863  -0.597  1.00  0.00           H  
HETATM   52  H24 UNL     1      -3.184   2.403   1.106  1.00  0.00           H  
HETATM   53  H25 UNL     1      -5.114   1.899  -0.813  1.00  0.00           H  
HETATM   54  H26 UNL     1      -5.652  -1.407  -1.259  1.00  0.00           H  
HETATM   55  H27 UNL     1      -6.430   0.154  -1.020  1.00  0.00           H  
HETATM   56  H28 UNL     1      -7.356  -0.492   0.918  1.00  0.00           H  
HETATM   57  H29 UNL     1      -7.847  -2.458   0.375  1.00  0.00           H  
HETATM   58  H30 UNL     1      -6.037  -1.536   2.802  1.00  0.00           H  
HETATM   59  H31 UNL     1      -5.750   0.160   2.389  1.00  0.00           H  
HETATM   60  H32 UNL     1      -4.000  -2.308   2.115  1.00  0.00           H  
HETATM   61  H33 UNL     1      -3.612  -0.683   2.708  1.00  0.00           H  
HETATM   62  H34 UNL     1      -3.000  -1.982  -1.229  1.00  0.00           H  
HETATM   63  H35 UNL     1      -2.751  -2.821   0.416  1.00  0.00           H  
HETATM   64  H36 UNL     1      -4.347  -2.626  -0.291  1.00  0.00           H  
HETATM   65  H37 UNL     1      -2.135   0.196   1.874  1.00  0.00           H  
HETATM   66  H38 UNL     1      -1.139  -1.901   1.450  1.00  0.00           H  
HETATM   67  H39 UNL     1      -1.210  -1.729  -0.310  1.00  0.00           H  
HETATM   68  H40 UNL     1       1.044  -1.332   0.496  1.00  0.00           H  
HETATM   69  H41 UNL     1       0.482  -0.257   1.790  1.00  0.00           H  
HETATM   70  H42 UNL     1      -0.341  -0.469  -1.642  1.00  0.00           H  
HETATM   71  H43 UNL     1      -0.251   1.240  -2.080  1.00  0.00           H  
HETATM   72  H44 UNL     1       1.197   0.230  -2.134  1.00  0.00           H  
CONECT    1    2   29   30   31
CONECT    2    3    4    4
CONECT    3   32   33   34
CONECT    4    5   35
CONECT    5    6   36   37
CONECT    6    7   38   39
CONECT    7    8    9   40
CONECT    8   41   42   43
CONECT    9   10   27   44
CONECT   10   11   45   46
CONECT   11   12   47   48
CONECT   12   13   27   49
CONECT   13   14   24   50
CONECT   14   15   51   52
CONECT   15   16   16   53
CONECT   16   17   22
CONECT   17   18   54   55
CONECT   18   19   20   56
CONECT   19   57
CONECT   20   21   58   59
CONECT   21   22   60   61
CONECT   22   23   24
CONECT   23   62   63   64
CONECT   24   25   65
CONECT   25   26   66   67
CONECT   26   27   68   69
CONECT   27   28
CONECT   28   70   71   72
END

HMDB0002719
     RDKit          3D
Desmosterol
 72 75  0  0  0  0  0  0  0  0999 V2000
    7.1713   -0.6271    0.9787 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5413   -1.6127    0.0920 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0770   -3.0185    0.0687 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5223   -1.3610   -0.7027 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9446    0.0069   -0.7287 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4760   -0.0424   -0.3181 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9354    1.3597   -0.3581 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0309    1.9736   -1.7368 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6455    1.5425    0.3251 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2128    2.9903    0.2271 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2725    2.9288   -0.1644 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6447    1.6067    0.3902 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9473    1.0327   -0.0612 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0817    1.9940    0.0758 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3297    1.3102   -0.3170 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5199    0.0346   -0.0899 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7956   -0.5962   -0.5057 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4231   -1.1177    0.7757 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.9060   -2.4180    0.6523 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5915   -0.8855    1.9919 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1548   -1.2497    1.8965 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5126   -0.8228    0.5729 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.3491   -2.1204   -0.2085 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1943   -0.1765    0.8135 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0477   -1.1383    0.6205 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3055   -0.5518    0.7141 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4909    0.7103   -0.0937 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3195    0.4420   -1.5306 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4308   -0.3535    1.7859 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4792    0.3116    0.4536 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0228   -1.0927    1.5110 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9891   -3.0970    0.6732 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2647   -3.7028    0.3731 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2618   -3.2345   -1.0173 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0671   -2.0966   -1.3516 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5323    0.6438   -0.0525 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0612    0.4698   -1.7470 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9387   -0.7940   -0.8719 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4741   -0.3522    0.7587 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6863    1.9443    0.2665 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0635    2.4581   -2.0636 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7860    2.7832   -1.8160 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3469    1.2182   -2.5166 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8162    1.3358    1.4236 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8083    3.6126   -0.4300 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2107    3.4883    1.2228 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8557    3.7263    0.3639 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4295    3.0808   -1.2279 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6224    1.6445    1.4805 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9477    0.6661   -1.1104 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8535    2.8635   -0.5974 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1839    2.4028    1.1063 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1142    1.8993   -0.8134 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6523   -1.4070   -1.2592 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4299    0.1544   -1.0198 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3561   -0.4916    0.9184 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8466   -2.4584    0.3754 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0369   -1.5364    2.8022 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7501    0.1605    2.3894 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9998   -2.3075    2.1149 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6119   -0.6834    2.7080 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0002   -1.9816   -1.2286 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7506   -2.8206    0.4161 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3472   -2.6258   -0.2914 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1353    0.1963    1.8745 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1393   -1.9007    1.4504 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2103   -1.7288   -0.3100 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0441   -1.3322    0.4962 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4824   -0.2570    1.7900 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3414   -0.4690   -1.6422 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2509    1.2398   -2.0797 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1969    0.2296   -2.1337 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 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  6
 22 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  6
 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
  3 32  1  0
  3 33  1  0
  3 34  1  0
  4 35  1  0
  5 36  1  0
  5 37  1  0
  6 38  1  0
  6 39  1  0
  7 40  1  1
  8 41  1  0
  8 42  1  0
  8 43  1  0
  9 44  1  1
 10 45  1  0
 10 46  1  0
 11 47  1  0
 11 48  1  0
 12 49  1  1
 13 50  1  6
 14 51  1  0
 14 52  1  0
 15 53  1  0
 17 54  1  0
 17 55  1  0
 18 56  1  1
 19 57  1  0
 20 58  1  0
 20 59  1  0
 21 60  1  0
 21 61  1  0
 23 62  1  0
 23 63  1  0
 23 64  1  0
 24 65  1  1
 25 66  1  0
 25 67  1  0
 26 68  1  0
 26 69  1  0
 28 70  1  0
 28 71  1  0
 28 72  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
24-Dehydrocholesterol	ChEBI
3beta-Cholesta-5,24-dien-3-ol	ChEBI
Cholesta-5,24-dien-3beta-ol	ChEBI
3b-Cholesta-5,24-dien-3-ol	Generator
3Β-cholesta-5,24-dien-3-ol	Generator
Cholesta-5,24-dien-3b-ol	Generator
Cholesta-5,24-dien-3β-ol	Generator
Cholest-5,24-dien-3beta-ol	HMDB
Cholesta-5,24-dien-3-ol	HMDB
24 Dehydrocholesterol	HMDB
Demosterol	HMDB
(3beta)-Cholesta-5,24-dien-3-ol	HMDB
(3Β)-cholesta-5,24-dien-3-ol	HMDB
24,25-Dehydrocholesterol	HMDB
Desmosterol	HMDB

Chemical Formula

C₂₇H₄₄O

Average Molecular Weight

384.6377

Monoisotopic Molecular Weight

384.33921603

IUPAC Name

(1S,2R,5S,10S,11S,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylhept-5-en-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-5-ol

Traditional Name

(1S,2R,5S,10S,11S,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylhept-5-en-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-5-ol

CAS Registry Number

313-04-2

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)CCC=C(C)C

InChI Identifier

InChI=1S/C27H44O/c1-18(2)7-6-8-19(3)23-11-12-24-22-10-9-20-17-21(28)13-15-26(20,4)25(22)14-16-27(23,24)5/h7,9,19,21-25,28H,6,8,10-17H2,1-5H3/t19-,21+,22+,23-,24+,25+,26+,27-/m1/s1

InChI Key

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

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

cholestanoid (CHEBI:17737 )
3beta-sterol (CHEBI:17737 )
Cholesterol and derivatives (C01802 )
Cholestane and derivatives (C01802 )
Cholesterol and derivatives (LMST01010016 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 2010161)
Semen (PMID: 11762778)

Organ

Brain (HMDB: HMDB0002719)
Kidney (HMDB: HMDB0002719)

Cellular substructure

Membrane (HMDB: HMDB0002719)
Extracellular (HMDB: HMDB0002719)

Organelle

Endoplasmic reticulum (HMDB: HMDB0002719)

Source

Exogenous

Exogenous (HMDB: HMDB0002719)

Food

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)

Herb and spice mixture

Curry powder (FooDB: FOOD00678)

Herbs and Spices (FooDB: FOOD00866)

Vegetable

Cabbage

Onion-family vegetable

Allium (FooDB: FOOD00005)
Garden onion (FooDB: FOOD00006)
Leek (FooDB: FOOD00007)
Garden onion (var.) (FooDB: FOOD00226)
Shallot (FooDB: FOOD00243)
Wild leek (FooDB: FOOD00396)
Red onion (FooDB: FOOD00962)
Green onion (FooDB: FOOD00963)
Onion-family vegetables (FooDB: FOOD00855)

Root vegetable

Shoot vegetable

Leaf vegetable

Common beet (FooDB: FOOD00025)
Endive (FooDB: FOOD00048)
Rocket salad (ssp.) (FooDB: FOOD00077)
Swamp cabbage (FooDB: FOOD00091)
Lettuce (FooDB: FOOD00095)
Garden cress (FooDB: FOOD00099)
Spinach (FooDB: FOOD00178)
Swiss chard (FooDB: FOOD00237)
Chicory leaves (FooDB: FOOD00250)
Garland chrysanthemum (FooDB: FOOD00333)
Corn salad (FooDB: FOOD00340)
Jute (FooDB: FOOD00389)
Lambsquarters (FooDB: FOOD00394)
Malabar spinach (FooDB: FOOD00404)
New Zealand spinach (FooDB: FOOD00415)
Yautia (FooDB: FOOD00510)
Ostrich fern (FooDB: FOOD00556)
Romaine lettuce (FooDB: FOOD00888)
Iceberg lettuce (FooDB: FOOD00973)
Pea shoots (FooDB: FOOD00975)
Yau choy (FooDB: FOOD00976)
Water spinach (FooDB: FOOD00977)
Rocket salad (FooDB: FOOD00244)
Green vegetables (FooDB: FOOD00872)

Fruit vegetable

Pepper (FooDB: FOOD00040)
Olive (FooDB: FOOD00121)
Avocado (FooDB: FOOD00130)
Garden tomato (FooDB: FOOD00171)
Cherry tomato (FooDB: FOOD00172)
Garden tomato (var.) (FooDB: FOOD00173)
Eggplant (FooDB: FOOD00174)
Pepper (C. baccatum) (FooDB: FOOD00231)
Pepper (C. chinense) (FooDB: FOOD00232)
Pepper (Capsicum) (FooDB: FOOD00233)
Groundcherry (FooDB: FOOD00371)
Pepper (C. frutescens) (FooDB: FOOD00428)
Mexican groundcherry (FooDB: FOOD00491)
Pepper (C. pubescens) (FooDB: FOOD00849)
Green bell pepper (FooDB: FOOD00877)
Yellow bell pepper (FooDB: FOOD00878)
Orange bell pepper (FooDB: FOOD00879)
Red bell pepper (FooDB: FOOD00880)
Italian sweet red pepper (FooDB: FOOD00881)
Jalapeno pepper (FooDB: FOOD00955)
Cubanelle pepper (FooDB: FOOD00971)

Tuber

Stalk vegetable

Other vegetable

Giant butterbur (FooDB: FOOD00314)
Carob (FooDB: FOOD00321)
Chinese water chestnut (FooDB: FOOD00332)
Horseradish tree (FooDB: FOOD00379)
Sacred lotus (FooDB: FOOD00402)
Nopal (FooDB: FOOD00416)
Okra (FooDB: FOOD00420)
Sesbania flower (FooDB: FOOD00469)
Agave (FooDB: FOOD00563)
Narrowleaf cattail (FooDB: FOOD00564)
Heart of palm (FooDB: FOOD00718)
Tree fern (FooDB: FOOD00797)

Mushroom

Castanospermum australe (FooDB: FOOD00893)
Gentiana lutea (FooDB: FOOD00894)
Juniperus communis (FooDB: FOOD00895)
Albizia gummifera (FooDB: FOOD00896)

Brassica

Brassicas (FooDB: FOOD00857)

Fruit

Tropical fruit

Citrus

Lime (FooDB: FOOD00053)
Lemon (FooDB: FOOD00054)
Pummelo (FooDB: FOOD00055)
Mandarin orange (Clementine, Tangerine) (FooDB: FOOD00056)
Sweet orange (FooDB: FOOD00057)
Grapefruit/Pummelo hybrid (FooDB: FOOD00255)
Grapefruit (FooDB: FOOD00256)
Persian lime (FooDB: FOOD00543)
Sour orange (FooDB: FOOD00918)
Mikan (FooDB: FOOD00932)
Clementine (FooDB: FOOD00959)
Citrus (FooDB: FOOD00859)

Pome

Berry

Black crowberry (FooDB: FOOD00075)
Strawberry (FooDB: FOOD00083)
Black huckleberry (FooDB: FOOD00084)
Sea-buckthornberry (FooDB: FOOD00087)
Mulberry (FooDB: FOOD00116)
Black mulberry (FooDB: FOOD00117)
Black chokeberry (FooDB: FOOD00136)
Blackcurrant (FooDB: FOOD00155)
Redcurrant (FooDB: FOOD00156)
Gooseberry (FooDB: FOOD00157)
Cloudberry (FooDB: FOOD00161)
Red raspberry (FooDB: FOOD00162)
Black raspberry (FooDB: FOOD00163)
Black elderberry (FooDB: FOOD00166)
Rowanberry (FooDB: FOOD00176)
Vaccinium (Blueberry, Cranberry, Huckleberry) (FooDB: FOOD00188)
Lowbush blueberry (FooDB: FOOD00189)
Sparkleberry (FooDB: FOOD00190)
Highbush blueberry (FooDB: FOOD00191)
American cranberry (FooDB: FOOD00192)
Bilberry (FooDB: FOOD00193)
Lingonberry (FooDB: FOOD00194)
Muscadine grape (FooDB: FOOD00203)
Common grape (FooDB: FOOD00204)
Arctic blackberry (FooDB: FOOD00207)
Bayberry (FooDB: FOOD00209)
Elliott's blueberry (FooDB: FOOD00210)
Canada blueberry (FooDB: FOOD00211)
Bog bilberry (FooDB: FOOD00212)
Buffalo currant (FooDB: FOOD00213)
European cranberry (FooDB: FOOD00217)
Deerberry (FooDB: FOOD00218)
Cascade huckleberry (FooDB: FOOD00220)
Oval-leaf huckleberry (FooDB: FOOD00221)
Evergreen huckleberry (FooDB: FOOD00222)
Red huckleberry (FooDB: FOOD00223)
Summer grape (FooDB: FOOD00227)
Fox grape (FooDB: FOOD00228)
Half-highbush blueberry (FooDB: FOOD00248)
Jostaberry (FooDB: FOOD00257)
Sweet rowanberry (FooDB: FOOD00265)
Skunk currant (FooDB: FOOD00267)
Squashberry (FooDB: FOOD00344)
Elderberry (FooDB: FOOD00358)
Grape (FooDB: FOOD00369)
Alaska blueberry (FooDB: FOOD00380)
Loganberry (FooDB: FOOD00400)
Ohelo berry (FooDB: FOOD00419)
Salmonberry (FooDB: FOOD00456)
Strawberry guava (FooDB: FOOD00482)
Boysenberry (FooDB: FOOD00542)
Chinese bayberry (FooDB: FOOD00852)
Saskatoon berry (FooDB: FOOD00884)
Nanking cherry (FooDB: FOOD00885)
Rabbiteye blueberry (FooDB: FOOD00898)
Blackberry (FooDB: FOOD00906)
Partridge berry (FooDB: FOOD00931)
Green grape (FooDB: FOOD00964)
Red grape (FooDB: FOOD00965)
Black plum (FooDB: FOOD00966)
Black raisin (FooDB: FOOD00968)
Chinese plum (FooDB: FOOD00978)
Green plum (FooDB: FOOD00979)
Wampee (FooDB: FOOD00980)
Goji (FooDB: FOOD00982)
Monk fruit (FooDB: FOOD00983)
Hawthorn (FooDB: FOOD00985)
Lantern fruit (FooDB: FOOD00986)
Cape gooseberry (FooDB: FOOD00988)
Rubus (Blackberry, Raspberry) (FooDB: FOOD00160)

Other fruit

Fig (FooDB: FOOD00081)
Date (FooDB: FOOD00135)
Jujube (FooDB: FOOD00388)

Drupe

Prunus (Cherry, Plum) (FooDB: FOOD00143)
Apricot (FooDB: FOOD00144)
Sweet cherry (FooDB: FOOD00145)
Sour cherry (FooDB: FOOD00146)
European plum (FooDB: FOOD00147)
Peach (FooDB: FOOD00149)
Nectarine (FooDB: FOOD00229)
Peach (var.) (FooDB: FOOD00230)
Common chokecherry (FooDB: FOOD00562)

Fruits (FooDB: FOOD00871)

Nut

Cashew nut (FooDB: FOOD00011)
Peanut (FooDB: FOOD00016)
Brazil nut (FooDB: FOOD00024)
Pecan nut (FooDB: FOOD00044)
Chestnut (FooDB: FOOD00045)
Common hazelnut (FooDB: FOOD00062)
Black walnut (FooDB: FOOD00093)
Common walnut (FooDB: FOOD00094)
Pine nut (FooDB: FOOD00138)
Pistachio (FooDB: FOOD00140)
Almond (FooDB: FOOD00148)
Macadamia nut (M. tetraphylla) (FooDB: FOOD00225)
Japanese walnut (FooDB: FOOD00240)
Acorn (FooDB: FOOD00282)
Beech nut (FooDB: FOOD00299)
Butternut (FooDB: FOOD00316)
Chinese chestnut (FooDB: FOOD00331)
European chestnut (FooDB: FOOD00363)
Hazelnut (FooDB: FOOD00376)
Hickory nut (FooDB: FOOD00377)
Japanese chestnut (FooDB: FOOD00385)
Pili nut (FooDB: FOOD00432)
Colorado pinyon (FooDB: FOOD00433)
Macadamia nut (FooDB: FOOD00525)
Walnut (FooDB: FOOD00608)
Mixed nuts (FooDB: FOOD00771)
Nuts (FooDB: FOOD00869)

Cereal and cereal product

Cereal

Cereal product

Dough

Sourdough (FooDB: FOOD00275)

Leavened bread

Flat bread

Other bread

Potato bread (FooDB: FOOD00811)
Other bread (FooDB: FOOD00269)

Sweet bread

Raisin bread (FooDB: FOOD00817)

Cereals and cereal products (FooDB: FOOD00858)

Pulse

Pea

Lentil

Lentils (FooDB: FOOD00098)

Other pulse

Lupine (FooDB: FOOD00104)
White lupine (FooDB: FOOD00403)

Bean

Green lentil (FooDB: FOOD00970)
Pulses (FooDB: FOOD00867)

Gourd

Watermelon (FooDB: FOOD00052)
Muskmelon (FooDB: FOOD00064)
Cucumber (FooDB: FOOD00065)
Cucurbita (FooDB: FOOD00066)
Bitter gourd (FooDB: FOOD00115)
Winter squash (FooDB: FOOD00283)
Butternut squash (FooDB: FOOD00317)
Calabash (FooDB: FOOD00318)
Chayote (FooDB: FOOD00325)
Towel gourd (FooDB: FOOD00492)
Wax gourd (FooDB: FOOD00499)
Tinda (FooDB: FOOD00559)
Horned melon (FooDB: FOOD00761)
Sunburst squash (pattypan squash) (FooDB: FOOD00874)
Green zucchini (FooDB: FOOD00875)
Yellow zucchini (FooDB: FOOD00876)
Japanese pumpkin (FooDB: FOOD00886)
Acorn squash (FooDB: FOOD00972)
Cantaloupe melon (FooDB: FOOD00984)

Coffee and coffee product

Coffee

Arabica coffee (FooDB: FOOD00059)
Robusta coffee (FooDB: FOOD00060)

Soy

Soy bean (FooDB: FOOD00085)

Soy product

Dish

Other dish

Taco shell (FooDB: FOOD00991)
Tostada shell (FooDB: FOOD00992)

Tea

Herbal tea

Hibiscus tea (FooDB: FOOD00723)
Greenthread tea (FooDB: FOOD00820)

Baking good

Wrapper

Wonton wrapper (FooDB: FOOD00818)

Abalone (FooDB: FOOD00279)
Conch (FooDB: FOOD00611)

Cocoa and cocoa product

Cocoa

Cocoa bean (FooDB: FOOD00182)

Endogenous

Endogenous (HMDB: HMDB0002719)

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Steroid Biosynthesis (HMDB: HMDB0002719)
Cholesterol Biosynthesis and Metabolism CE(14:0) (PathBank: SMP0002435)
Cholesterol Biosynthesis and Metabolism CE(10:0) (PathBank: SMP0002436)
Cholesterol Biosynthesis and Metabolism CE(12:0) (PathBank: SMP0002438)
Cholesterol Biosynthesis and Metabolism CE(16:0) (PathBank: SMP0002440)
Cholesterol Biosynthesis and Metabolism CE(18:0) (PathBank: SMP0002441)
Cholesterol Biosynthesis and Metabolism (PathBank: SMP0070041)
Bloch Pathway (Cholesterol Biosynthesis) (PathBank: SMP0121057)

Disease pathway

Desmosterolosis (HMDB: HMDB0002719)
Smith-Lemli-Opitz Syndrome (SLOS) (PathBank: SMP0120515)
Mevalonic Aciduria (PathBank: SMP0120794)
Lysosomal Acid Lipase Deficiency (Wolman Disease) (PathBank: SMP0120512)
Cholesteryl Ester Storage Disease (PathBank: SMP0120573)
CHILD Syndrome (PathBank: SMP0120464)
Wolman Disease (PathBank: SMP0120576)
Chondrodysplasia Punctata II, X-Linked Dominant (CDPX2) (PathBank: SMP0120685)
Hypercholesterolemia (PathBank: SMP0120769)
Hyper-IgD Syndrome (PathBank: SMP0120574)

Drug action pathway

Ibandronate Action Pathway (PathBank: SMP0000079)
Simvastatin Action Pathway (PathBank: SMP0000082)
Pravastatin Action Pathway (PathBank: SMP0000089)
Rosuvastatin Action Pathway (PathBank: SMP0000092)
Alendronate Action Pathway (PathBank: SMP0000095)
Lovastatin Action Pathway (PathBank: SMP0000099)
Zoledronate Action Pathway (PathBank: SMP0000107)
Cerivastatin Action Pathway (PathBank: SMP0000111)
Risedronate Action Pathway (PathBank: SMP0000112)
Pamidronate Action Pathway (PathBank: SMP0000117)
Fluvastatin Action Pathway (PathBank: SMP0000119)
Atorvastatin Action Pathway (PathBank: SMP0000131)

Role

Biological role

Human metabolite (HMDB: HMDB0002719)

Industrial application

Pharmaceutical industry

Biomarker

Desmosterolosis (MarkerDB: MDB00000398)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	121.5 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M-H]-	MetCCS_train_neg	210.049	30932474
[M-H]-	Not Available	210.049	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000265

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.00011 g/L	ALOGPS
logP	6.62	ALOGPS
logP	6.71	ChemAxon
logS	-6.5	ALOGPS
pKa (Strongest Acidic)	18.2	ChemAxon
pKa (Strongest Basic)	-1.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	20.23 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	121.47 m³·mol⁻¹	ChemAxon
Polarizability	49.67 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]+	193.728	31661259
DarkChem	[M-H]-	189.886	31661259
DeepCCS	[M-2H]-	231.367	30932474
DeepCCS	[M+Na]+	205.577	30932474
AllCCS	[M+H]+	203.9	32859911
AllCCS	[M+H-H2O]+	201.8	32859911
AllCCS	[M+NH4]+	206.0	32859911
AllCCS	[M+Na]+	206.5	32859911
AllCCS	[M-H]-	204.7	32859911
AllCCS	[M+Na-2H]-	206.3	32859911
AllCCS	[M+HCOO]-	208.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Desmosterol	[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)CCC=C(C)C	2436.2	Standard polar	33892256
Desmosterol	[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)CCC=C(C)C	3122.4	Standard non polar	33892256
Desmosterol	[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)CCC=C(C)C	3204.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Desmosterol,1TMS,isomer #1	CC(C)=CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CC=C4C[C@@H](O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C	3200.9	Semi standard non polar	33892256
Desmosterol,1TBDMS,isomer #1	CC(C)=CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C	3425.5	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Desmosterol EI-B (Non-derivatized)	splash10-00xr-6973000000-9b8478114c7fec1504f2	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Desmosterol EI-B (Non-derivatized)	splash10-00xr-6973000000-9b8478114c7fec1504f2	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Desmosterol GC-MS (Non-derivatized) - 70eV, Positive	splash10-0axr-1109000000-c96b90d5bc5f0ee8db10	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Desmosterol GC-MS (1 TMS) - 70eV, Positive	splash10-002f-3105900000-043e100bd5bd92eb1582	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Desmosterol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0avl-7941000000-99b5e69bc97a4056fa8c	2014-09-20	Not Available	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Desmosterol 10V, Positive-QTOF	splash10-014r-0019000000-9cec9aa1e8ad662bef64	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Desmosterol 20V, Positive-QTOF	splash10-014i-2149000000-6218d03e9c19a9f2887f	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Desmosterol 40V, Positive-QTOF	splash10-02ta-4259000000-713a8956eb12b8b2003d	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Desmosterol 10V, Negative-QTOF	splash10-001i-0009000000-387b878bf983d0b8ac76	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Desmosterol 20V, Negative-QTOF	splash10-001i-0009000000-2d0cbb4e60d96f291bce	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Desmosterol 40V, Negative-QTOF	splash10-0gb9-1019000000-37313ec6fa045ceba894	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Desmosterol 10V, Negative-QTOF	splash10-001i-0009000000-4d7a5f3b63c0fb62f1d7	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Desmosterol 20V, Negative-QTOF	splash10-001i-0009000000-3697eddae534b800a992	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Desmosterol 40V, Negative-QTOF	splash10-001i-0009000000-e7c1ee286ab735e93547	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Desmosterol 10V, Positive-QTOF	splash10-000i-1009000000-1881c8faacf610d02817	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Desmosterol 20V, Positive-QTOF	splash10-0a4i-7094000000-adf191ce524bfed85be3	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Desmosterol 40V, Positive-QTOF	splash10-0a4l-9710000000-dc3e59d9eff8b9729026	2021-09-22	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane (predicted from logP)
Endoplasmic reticulum

Biospecimen Locations

Blood
Semen

Tissue Locations

Brain
Kidney

Pathways

Name	SMPDB/PathBank	KEGG
Steroid Biosynthesis
Smith-Lemli-Opitz Syndrome (SLOS)		Not Available
CHILD Syndrome		Not Available
Desmosterolosis		Not Available
Chondrodysplasia Punctata II, X Linked Dominant (CDPX2)		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	1.300 +/- 0.780 uM	Children (1-13 years old)	Not Specified	Normal	12457401	details
Blood	Detected and Quantified	1.81 +/- 0.067 uM	Adult (>18 years old)	Both	Normal	20671299	details
Blood	Detected and Quantified	0.79 +/- 0.017 uM	Adult (>18 years old)	Both	Normal	20671299	details
Blood	Detected and Quantified	2.9 +/- 0.2 uM	Adult (>18 years old)	Not Specified	Normal	2010161	details
Blood	Detected and Quantified	2.37 +/- 1.04 uM	Adult (>18 years old)	Not Specified	Normal	16807145	details
Semen	Detected and Quantified	180 +/- 20 uM	Adult (>18 years old)	Male	Normal	11762778	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	155.991 uM	Children (1-13 years old)	Male	Desmosterolosis	12457401	details
Blood	Detected and Quantified	2.9 +/- 0.4 uM	Adult (>18 years old)	Not Specified	Primary biliary cirrhosis	2010161	details

Associated Disorders and Diseases

Disease References

Primary biliary cirrhosis
Nikkila K, Hockerstedt K, Miettinen TA: High cholestanol and low campesterol-to-sitosterol ratio in serum of patients with primary biliary cirrhosis before liver transplantation. Hepatology. 1991 Apr;13(4):663-9. [PubMed:2010161 ]
Desmosterolosis
Andersson HC, Kratz L, Kelley R: Desmosterolosis presenting with multiple congenital anomalies and profound developmental delay. Am J Med Genet. 2002 Dec 15;113(4):315-9. doi: 10.1002/ajmg.b.10873. [PubMed:12457401 ]

Associated OMIM IDs

109720 (Primary biliary cirrhosis)
602398 (Desmosterolosis)

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Wikipedia Link

METLIN ID

PubChem Compound

PDB ID

Not Available

ChEBI ID

17737

Food Biomarker Ontology

Not Available

VMH ID

DSMSTEROL

MarkerDB ID

MDB00000398

Good Scents ID

Not Available

References

Synthesis Reference

Kircher, Henry W.; Rosenstein, Fumiko U. Preparation of desmosterol from (20S,22R,S)-3b-acetoxychola-5,23-dien-22-ol. Journal of Organic Chemistry (1987), 52(12), 2586-8.

Material Safety Data Sheet (MSDS)

Not Available

General References

Miettinen TE, Kesaniemi YA, Gylling H, Jarvinen H, Silvennoinen E, Miettinen TA: Noncholesterol sterols in bile and stones of patients with cholesterol and pigment stones. Hepatology. 1996 Feb;23(2):274-80. [PubMed:8591852 ]
Phillips KM, Ruggio DM, Bailey JA: Precise quantitative determination of phytosterols, stanols, and cholesterol metabolites in human serum by capillary gas-liquid chromatography. J Chromatogr B Biomed Sci Appl. 1999 Sep 10;732(1):17-29. [PubMed:10517218 ]
Siirtola A, Ketomaki A, Miettinen TA, Gylling H, Lehtimaki T, Holmberg C, Salo MK, Antikainen M: Cholesterol absorption and synthesis in pediatric kidney, liver, and heart transplant recipients. Transplantation. 2006 Feb 15;81(3):327-34. [PubMed:16477216 ]
Miettinen TA, Kesaniemi YA, Jarvinen H, Hastbacka J: Cholesterol precursor sterols, plant sterols, and cholestanol in human bile and gallstones. Gastroenterology. 1986 Apr;90(4):858-64. [PubMed:3081398 ]
Rosenfeld RS, Bradlow HL, Levin J, Zumoff B: Preparation of [24,25-3H] cholesterol. Oxidation in man as a measure of bile acid formation. J Lipid Res. 1978 Sep;19(7):850-5. [PubMed:712244 ]
Dennick RG, Dean PD, Abramovich DA: Desmosterol levels in human foetal brain--a reassessment. J Neurochem. 1973 Apr;20(4):1293-4. [PubMed:4697890 ]
Nordby G, Norum KR: Substrate specificity of lecithin:cholesterol acyltransferase. Esterification of desmosterol, b-sitosterol, and cholecalciferol in human plasma. Scand J Clin Lab Invest. 1975 Nov;35(7):677-82. [PubMed:174187 ]
Beasley CL, Honer WG, Bergmann K, Falkai P, Lutjohann D, Bayer TA: Reductions in cholesterol and synaptic markers in association cortex in mood disorders. Bipolar Disord. 2005 Oct;7(5):449-55. [PubMed:16176438 ]
Paoletti P, Pezzotta S, Racca AR, Fumagalli R: Chemotherapy of human nervous system tumors: influence on cerebrospinal fluid sterols. Natl Cancer Inst Monogr. 1977 Dec;46:125-6. [PubMed:613223 ]
Volpe JJ, Hennessy SW: Cholesterol biosynthesis and 3-hydroxy-3-methyl-glutaryl coenzyme A reductase in cultured glial and neuronal cells. Regulation by lipoprotein and by certain free sterols. Biochim Biophys Acta. 1977 Mar 25;486(3):408-20. [PubMed:856284 ]
Clark RM, Fey MB, Jensen RG, Hill DW: Desmosterol in human milk. Lipids. 1983 Mar;18(3):264-6. [PubMed:6855485 ]
Porter FD: Human malformation syndromes due to inborn errors of cholesterol synthesis. Curr Opin Pediatr. 2003 Dec;15(6):607-13. [PubMed:14631207 ]
Yu H, Patel SB: Recent insights into the Smith-Lemli-Opitz syndrome. Clin Genet. 2005 Nov;68(5):383-91. [PubMed:16207203 ]

Enzymes

Enzyme Details

1. Delta(24)-sterol reductase

General function:: Energy production and conversion
Specific function:: Catalyzes the reduction of the delta-24 double bond of sterol intermediates. Protects cells from oxidative stress by reducing caspase 3 activity during apoptosis induced by oxidative stress. Also protects against amyloid-beta peptide-induced apoptosis.
Gene Name:: DHCR24
Uniprot ID:: Q15392
Molecular weight:: 60100.805

Reactions

Cholesterol + NADP → Desmosterol + Hydrogen Ion + NADPH	details

Showing metabocard for Desmosterol (HMDB0002719)

MOL for HMDB0002719 (Desmosterol)

3D MOL for HMDB0002719 (Desmosterol)

3D SDF for HMDB0002719 (Desmosterol)

3D-SDF for HMDB0002719 (Desmosterol)

PDB for HMDB0002719 (Desmosterol)

3D PDB for HMDB0002719 (Desmosterol)

SMILES for HMDB0002719 (Desmosterol)

INCHI for HMDB0002719 (Desmosterol)

Structure for HMDB0002719 (Desmosterol)

3D Structure for HMDB0002719 (Desmosterol)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

Reactions