Jump To Section:

Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2022-03-07 02:49:08 UTC

HMDB ID

HMDB0001170

Secondary Accession Numbers

HMDB01170

Metabolite Identification

Common Name

Lathosterol

Description

Lathosterol is a a sterol (a combination steroid and alcohol) and a lipid found in the cell membranes of all body tissues, and transported in the blood plasma of all animals. It is used as an indicator of whole-body cholesterol synthesis (PMID 14511438 ). Plasma lathosterol levels are significantly elevated in patients with bile acid malabsorption (PMID:8777839 ). Lathosterol oxidase (EC 1.14.21.6) is an enzyme that catalyzes the chemical reaction 5alpha-cholest-7-en-3beta-ol + NAD(P)H + H+ + O2 cholesta-5,7-dien-3beta-ol + NAD(P)+ + 2 H2O.

Structure

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

  Mrv1652309042000182D          

 32 35  0  0  0  0            999 V2000
    0.2305   -0.2409    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4852   -0.6538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2305    0.5609    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0077   -0.4887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2108   -0.2409    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4852   -1.4517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0077    0.8048    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4852    0.9665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2305    1.3691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4688    0.1893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9265   -0.6538    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2108    0.5609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2108   -1.8611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3209    1.5755    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9265   -1.4517    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.6487   -0.2409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9231    0.1136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1291    1.6925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7807    2.2151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6487   -1.8611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3679   -0.6538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6487    1.0490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3679   -1.4517    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4814    1.1557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0969   -1.8611    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9936    0.5023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6531   -0.2409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8126    0.6021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2409   -1.0490    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2211   -1.1248    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7682    1.1179    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9265   -2.4078    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  0  0  0  0
  1  4  1  0  0  0  0
  2  5  1  0  0  0  0
  2  6  2  0  0  0  0
  3  7  1  0  0  0  0
  3  8  1  0  0  0  0
  3  9  1  1  0  0  0
  4 10  1  0  0  0  0
  5 11  1  0  0  0  0
  5 12  1  0  0  0  0
  6 13  1  0  0  0  0
  7 14  1  0  0  0  0
 11 15  1  0  0  0  0
 11 16  1  0  0  0  0
 11 17  1  1  0  0  0
 14 18  1  0  0  0  0
 14 19  1  6  0  0  0
 15 20  1  0  0  0  0
 16 21  1  0  0  0  0
 18 22  1  0  0  0  0
 20 23  1  0  0  0  0
 22 24  1  0  0  0  0
 23 25  1  1  0  0  0
 24 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  1  0  0  0  0
  7 10  1  0  0  0  0
  8 12  1  0  0  0  0
 13 15  1  0  0  0  0
 21 23  1  0  0  0  0
  1 29  1  6  0  0  0
  5 30  1  6  0  0  0
  7 31  1  6  0  0  0
 15 32  1  6  0  0  0
M  END

HMDB0001170
     RDKit          3D
Lathosterol
 74 77  0  0  0  0  0  0  0  0999 V2000
    7.5759    0.3899   -1.1526 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4017   -0.2832   -0.5110 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8493   -1.4639    0.3567 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7099    0.7594    0.3735 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5205    0.2069    1.0526 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3629   -0.2550    0.2382 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6515    0.8020   -0.4678 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4898    1.5621   -1.4462 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3678    0.4618   -1.1098 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3348   -0.5848   -2.1598 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1589   -0.9364   -2.3189 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8113    0.0566   -1.4109 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0986   -0.3224   -0.8592 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8347   -1.3204   -1.3693 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1555   -1.6867   -0.7864 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8053   -0.4258   -0.2181 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.1985   -0.7283    0.2516 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7357    0.3376    1.1796 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.8020   -0.1469    2.4633 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8862    1.5630    1.0673 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4845    1.2420    1.6029 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8986    0.0547    0.8631 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.7089   -1.0882    1.8724 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5810    0.4430    0.3055 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5016    0.4943    1.3655 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2422    1.0575    0.7541 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2210    0.0551   -0.2566 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2619   -1.3469    0.2748 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4307    1.4678   -1.3428 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5257    0.2497   -0.5943 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7318   -0.0811   -2.1554 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6755   -0.6956   -1.2208 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8523   -1.1243    1.4326 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8738   -1.7237    0.0895 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1439   -2.3132    0.2812 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6372    1.7377   -0.0854 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4862    0.9179    1.2091 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8730   -0.5916    1.7676 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1782    1.0227    1.7821 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7320   -0.8677    0.9312 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7908   -0.9835   -0.5192 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3627    1.5993    0.3180 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8100    1.8403   -2.3411 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7672    2.5986   -1.0886 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2978    1.0123   -1.9087 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0177    1.4158   -1.6338 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9388   -1.4725   -1.9615 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7005   -0.1421   -3.1150 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3462   -1.9833   -2.0719 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4698   -0.7702   -3.3706 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8537    1.0426   -1.8815 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4576   -1.8568   -2.2099 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8005   -2.0332   -1.6151 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0884   -2.4987   -0.0396 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8267    0.3091   -1.0380 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8528   -0.7338   -0.6446 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3108   -1.7031    0.7368 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7770    0.6493    0.8705 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3386   -0.9915    2.4284 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7461    1.8587    0.0217 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2543    2.4024    1.6805 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5577    1.0171    2.6853 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8962    2.1765    1.4226 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4911   -0.7064    2.8836 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8946   -1.7742    1.5448 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6152   -1.7166    1.9395 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6861    1.5153   -0.0422 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3379   -0.4975    1.8343 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7733    1.1736    2.1997 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5563    1.9771    0.1883 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5396    1.2667    1.4865 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7314   -1.8583    0.0565 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9950   -1.9843   -0.2151 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4581   -1.3200    1.3501 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  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  0
  3 33  1  0
  3 34  1  0
  3 35  1  0
  4 36  1  0
  4 37  1  0
  5 38  1  0
  5 39  1  0
  6 40  1  0
  6 41  1  0
  7 42  1  1
  8 43  1  0
  8 44  1  0
  8 45  1  0
  9 46  1  6
 10 47  1  0
 10 48  1  0
 11 49  1  0
 11 50  1  0
 12 51  1  6
 14 52  1  0
 15 53  1  0
 15 54  1  0
 16 55  1  6
 17 56  1  0
 17 57  1  0
 18 58  1  6
 19 59  1  0
 20 60  1  0
 20 61  1  0
 21 62  1  0
 21 63  1  0
 23 64  1  0
 23 65  1  0
 23 66  1  0
 24 67  1  6
 25 68  1  0
 25 69  1  0
 26 70  1  0
 26 71  1  0
 28 72  1  0
 28 73  1  0
 28 74  1  0
M  END

  Mrv1652309042000182D          

 32 35  0  0  0  0            999 V2000
    0.2305   -0.2409    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4852   -0.6538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2305    0.5609    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0077   -0.4887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2108   -0.2409    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4852   -1.4517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0077    0.8048    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4852    0.9665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2305    1.3691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4688    0.1893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9265   -0.6538    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2108    0.5609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2108   -1.8611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3209    1.5755    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9265   -1.4517    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.6487   -0.2409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9231    0.1136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1291    1.6925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7807    2.2151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6487   -1.8611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3679   -0.6538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6487    1.0490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3679   -1.4517    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4814    1.1557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0969   -1.8611    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9936    0.5023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6531   -0.2409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8126    0.6021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2409   -1.0490    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2211   -1.1248    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7682    1.1179    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9265   -2.4078    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  0  0  0  0
  1  4  1  0  0  0  0
  2  5  1  0  0  0  0
  2  6  2  0  0  0  0
  3  7  1  0  0  0  0
  3  8  1  0  0  0  0
  3  9  1  1  0  0  0
  4 10  1  0  0  0  0
  5 11  1  0  0  0  0
  5 12  1  0  0  0  0
  6 13  1  0  0  0  0
  7 14  1  0  0  0  0
 11 15  1  0  0  0  0
 11 16  1  0  0  0  0
 11 17  1  1  0  0  0
 14 18  1  0  0  0  0
 14 19  1  6  0  0  0
 15 20  1  0  0  0  0
 16 21  1  0  0  0  0
 18 22  1  0  0  0  0
 20 23  1  0  0  0  0
 22 24  1  0  0  0  0
 23 25  1  1  0  0  0
 24 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  1  0  0  0  0
  7 10  1  0  0  0  0
  8 12  1  0  0  0  0
 13 15  1  0  0  0  0
 21 23  1  0  0  0  0
  1 29  1  6  0  0  0
  5 30  1  6  0  0  0
  7 31  1  6  0  0  0
 15 32  1  6  0  0  0
M  END
> <DATABASE_ID>
HMDB0001170

> <DATABASE_NAME>
hmdb

> <SMILES>
[H][C@@]1(CC[C@@]2([H])C3=CC[C@@]4([H])C[C@@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCCC(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C27H46O/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/h10,18-21,23-25,28H,6-9,11-17H2,1-5H3/t19-,20+,21+,23-,24+,25+,26+,27-/m1/s1

> <INCHI_KEY>
IZVFFXVYBHFIHY-SKCNUYALSA-N

> <FORMULA>
C27H46O

> <MOLECULAR_WEIGHT>
386.6535

> <EXACT_MASS>
386.354866094

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
74

> <JCHEM_AVERAGE_POLARIZABILITY>
50.51791582585771

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,2S,5S,7S,11R,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-9-en-5-ol

> <ALOGPS_LOGP>
7.40

> <JCHEM_LOGP>
7.112889030666665

> <ALOGPS_LOGS>
-7.04

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.361777845540015

> <JCHEM_PKA_STRONGEST_BASIC>
-1.3283583703607977

> <JCHEM_POLAR_SURFACE_AREA>
20.23

> <JCHEM_REFRACTIVITY>
120.61649999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.50e-05 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2S,5S,7S,11R,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-9-en-5-ol

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0001170
     RDKit          3D
Lathosterol
 74 77  0  0  0  0  0  0  0  0999 V2000
    7.5759    0.3899   -1.1526 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4017   -0.2832   -0.5110 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8493   -1.4639    0.3567 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7099    0.7594    0.3735 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5205    0.2069    1.0526 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3629   -0.2550    0.2382 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6515    0.8020   -0.4678 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4898    1.5621   -1.4462 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3678    0.4618   -1.1098 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3348   -0.5848   -2.1598 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1589   -0.9364   -2.3189 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8113    0.0566   -1.4109 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0986   -0.3224   -0.8592 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8347   -1.3204   -1.3693 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1555   -1.6867   -0.7864 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8053   -0.4258   -0.2181 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.1985   -0.7283    0.2516 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7357    0.3376    1.1796 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.8020   -0.1469    2.4633 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8862    1.5630    1.0673 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4845    1.2420    1.6029 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8986    0.0547    0.8631 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.7089   -1.0882    1.8724 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5810    0.4430    0.3055 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5016    0.4943    1.3655 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2422    1.0575    0.7541 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2210    0.0551   -0.2566 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2619   -1.3469    0.2748 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4307    1.4678   -1.3428 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5257    0.2497   -0.5943 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7318   -0.0811   -2.1554 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6755   -0.6956   -1.2208 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8523   -1.1243    1.4326 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8738   -1.7237    0.0895 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1439   -2.3132    0.2812 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6372    1.7377   -0.0854 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4862    0.9179    1.2091 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8730   -0.5916    1.7676 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1782    1.0227    1.7821 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7320   -0.8677    0.9312 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7908   -0.9835   -0.5192 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3627    1.5993    0.3180 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8100    1.8403   -2.3411 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7672    2.5986   -1.0886 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2978    1.0123   -1.9087 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0177    1.4158   -1.6338 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9388   -1.4725   -1.9615 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7005   -0.1421   -3.1150 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3462   -1.9833   -2.0719 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4698   -0.7702   -3.3706 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8537    1.0426   -1.8815 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4576   -1.8568   -2.2099 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8005   -2.0332   -1.6151 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0884   -2.4987   -0.0396 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8267    0.3091   -1.0380 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8528   -0.7338   -0.6446 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3108   -1.7031    0.7368 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7770    0.6493    0.8705 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3386   -0.9915    2.4284 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7461    1.8587    0.0217 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2543    2.4024    1.6805 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5577    1.0171    2.6853 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8962    2.1765    1.4226 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4911   -0.7064    2.8836 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8946   -1.7742    1.5448 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6152   -1.7166    1.9395 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6861    1.5153   -0.0422 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3379   -0.4975    1.8343 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7733    1.1736    2.1997 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5563    1.9771    0.1883 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5396    1.2667    1.4865 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7314   -1.8583    0.0565 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9950   -1.9843   -0.2151 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4581   -1.3200    1.3501 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  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  0
  3 33  1  0
  3 34  1  0
  3 35  1  0
  4 36  1  0
  4 37  1  0
  5 38  1  0
  5 39  1  0
  6 40  1  0
  6 41  1  0
  7 42  1  1
  8 43  1  0
  8 44  1  0
  8 45  1  0
  9 46  1  6
 10 47  1  0
 10 48  1  0
 11 49  1  0
 11 50  1  0
 12 51  1  6
 14 52  1  0
 15 53  1  0
 15 54  1  0
 16 55  1  6
 17 56  1  0
 17 57  1  0
 18 58  1  6
 19 59  1  0
 20 60  1  0
 20 61  1  0
 21 62  1  0
 21 63  1  0
 23 64  1  0
 23 65  1  0
 23 66  1  0
 24 67  1  6
 25 68  1  0
 25 69  1  0
 26 70  1  0
 26 71  1  0
 28 72  1  0
 28 73  1  0
 28 74  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       0.430  -0.450   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.906  -1.220   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.430   1.047   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.881  -0.912   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.260  -0.450   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.906  -2.710   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.881   1.502   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.906   1.804   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.430   2.556   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.742   0.353   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -3.596  -1.220   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.260   1.047   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.260  -3.474   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.466   2.941   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -3.596  -2.710   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -4.944  -0.450   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -3.590   0.212   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.974   3.159   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.457   4.135   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -4.944  -3.474   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -6.287  -1.220   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.944   1.958   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -6.287  -2.710   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       6.499   2.157   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      -7.648  -3.474   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       7.455   0.938   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       6.819  -0.450   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       8.983   1.124   0.000  0.00  0.00           C+0
HETATM   29  H   UNK     0       0.450  -1.958   0.000  0.00  0.00           H+0
HETATM   30  H   UNK     0      -2.279  -2.100   0.000  0.00  0.00           H+0
HETATM   31  H   UNK     0       3.301   2.087   0.000  0.00  0.00           H+0
HETATM   32  H   UNK     0      -3.596  -4.495   0.000  0.00  0.00           H+0
CONECT    1    2    3    4   29                                             
CONECT    2    1    5    6                                                  
CONECT    3    1    7    8    9                                             
CONECT    4    1   10                                                       
CONECT    5    2   11   12   30                                             
CONECT    6    2   13                                                       
CONECT    7    3   14   10   31                                             
CONECT    8    3   12                                                       
CONECT    9    3                                                            
CONECT   10    4    7                                                       
CONECT   11    5   15   16   17                                             
CONECT   12    5    8                                                       
CONECT   13    6   15                                                       
CONECT   14    7   18   19                                                  
CONECT   15   11   20   13   32                                             
CONECT   16   11   21                                                       
CONECT   17   11                                                            
CONECT   18   14   22                                                       
CONECT   19   14                                                            
CONECT   20   15   23                                                       
CONECT   21   16   23                                                       
CONECT   22   18   24                                                       
CONECT   23   20   25   21                                                  
CONECT   24   22   26                                                       
CONECT   25   23                                                            
CONECT   26   24   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26                                                            
CONECT   29    1                                                            
CONECT   30    5                                                            
CONECT   31    7                                                            
CONECT   32   15                                                            
MASTER        0    0    0    0    0    0    0    0   32    0   70    0
END

COMPND    HMDB0001170
HETATM    1  C1  UNL     1       7.576   0.390  -1.153  1.00  0.00           C  
HETATM    2  C2  UNL     1       6.402  -0.283  -0.511  1.00  0.00           C  
HETATM    3  C3  UNL     1       6.849  -1.464   0.357  1.00  0.00           C  
HETATM    4  C4  UNL     1       5.710   0.759   0.374  1.00  0.00           C  
HETATM    5  C5  UNL     1       4.521   0.207   1.053  1.00  0.00           C  
HETATM    6  C6  UNL     1       3.363  -0.255   0.238  1.00  0.00           C  
HETATM    7  C7  UNL     1       2.652   0.802  -0.468  1.00  0.00           C  
HETATM    8  C8  UNL     1       3.490   1.562  -1.446  1.00  0.00           C  
HETATM    9  C9  UNL     1       1.368   0.462  -1.110  1.00  0.00           C  
HETATM   10  C10 UNL     1       1.335  -0.585  -2.160  1.00  0.00           C  
HETATM   11  C11 UNL     1      -0.159  -0.936  -2.319  1.00  0.00           C  
HETATM   12  C12 UNL     1      -0.811   0.057  -1.411  1.00  0.00           C  
HETATM   13  C13 UNL     1      -2.099  -0.322  -0.859  1.00  0.00           C  
HETATM   14  C14 UNL     1      -2.835  -1.320  -1.369  1.00  0.00           C  
HETATM   15  C15 UNL     1      -4.156  -1.687  -0.786  1.00  0.00           C  
HETATM   16  C16 UNL     1      -4.805  -0.426  -0.218  1.00  0.00           C  
HETATM   17  C17 UNL     1      -6.199  -0.728   0.252  1.00  0.00           C  
HETATM   18  C18 UNL     1      -6.736   0.338   1.180  1.00  0.00           C  
HETATM   19  O1  UNL     1      -6.802  -0.147   2.463  1.00  0.00           O  
HETATM   20  C19 UNL     1      -5.886   1.563   1.067  1.00  0.00           C  
HETATM   21  C20 UNL     1      -4.484   1.242   1.603  1.00  0.00           C  
HETATM   22  C21 UNL     1      -3.899   0.055   0.863  1.00  0.00           C  
HETATM   23  C22 UNL     1      -3.709  -1.088   1.872  1.00  0.00           C  
HETATM   24  C23 UNL     1      -2.581   0.443   0.305  1.00  0.00           C  
HETATM   25  C24 UNL     1      -1.502   0.494   1.365  1.00  0.00           C  
HETATM   26  C25 UNL     1      -0.242   1.058   0.754  1.00  0.00           C  
HETATM   27  C26 UNL     1       0.221   0.055  -0.257  1.00  0.00           C  
HETATM   28  C27 UNL     1       0.262  -1.347   0.275  1.00  0.00           C  
HETATM   29  H1  UNL     1       7.431   1.468  -1.343  1.00  0.00           H  
HETATM   30  H2  UNL     1       8.526   0.250  -0.594  1.00  0.00           H  
HETATM   31  H3  UNL     1       7.732  -0.081  -2.155  1.00  0.00           H  
HETATM   32  H4  UNL     1       5.675  -0.696  -1.221  1.00  0.00           H  
HETATM   33  H5  UNL     1       6.852  -1.124   1.433  1.00  0.00           H  
HETATM   34  H6  UNL     1       7.874  -1.724   0.090  1.00  0.00           H  
HETATM   35  H7  UNL     1       6.144  -2.313   0.281  1.00  0.00           H  
HETATM   36  H8  UNL     1       5.637   1.738  -0.085  1.00  0.00           H  
HETATM   37  H9  UNL     1       6.486   0.918   1.209  1.00  0.00           H  
HETATM   38  H10 UNL     1       4.873  -0.592   1.768  1.00  0.00           H  
HETATM   39  H11 UNL     1       4.178   1.023   1.782  1.00  0.00           H  
HETATM   40  H12 UNL     1       2.732  -0.868   0.931  1.00  0.00           H  
HETATM   41  H13 UNL     1       3.791  -0.983  -0.519  1.00  0.00           H  
HETATM   42  H14 UNL     1       2.363   1.599   0.318  1.00  0.00           H  
HETATM   43  H15 UNL     1       2.810   1.840  -2.341  1.00  0.00           H  
HETATM   44  H16 UNL     1       3.767   2.599  -1.089  1.00  0.00           H  
HETATM   45  H17 UNL     1       4.298   1.012  -1.909  1.00  0.00           H  
HETATM   46  H18 UNL     1       1.018   1.416  -1.634  1.00  0.00           H  
HETATM   47  H19 UNL     1       1.939  -1.473  -1.961  1.00  0.00           H  
HETATM   48  H20 UNL     1       1.700  -0.142  -3.115  1.00  0.00           H  
HETATM   49  H21 UNL     1      -0.346  -1.983  -2.072  1.00  0.00           H  
HETATM   50  H22 UNL     1      -0.470  -0.770  -3.371  1.00  0.00           H  
HETATM   51  H23 UNL     1      -0.854   1.043  -1.881  1.00  0.00           H  
HETATM   52  H24 UNL     1      -2.458  -1.857  -2.210  1.00  0.00           H  
HETATM   53  H25 UNL     1      -4.801  -2.033  -1.615  1.00  0.00           H  
HETATM   54  H26 UNL     1      -4.088  -2.499  -0.040  1.00  0.00           H  
HETATM   55  H27 UNL     1      -4.827   0.309  -1.038  1.00  0.00           H  
HETATM   56  H28 UNL     1      -6.853  -0.734  -0.645  1.00  0.00           H  
HETATM   57  H29 UNL     1      -6.311  -1.703   0.737  1.00  0.00           H  
HETATM   58  H30 UNL     1      -7.777   0.649   0.870  1.00  0.00           H  
HETATM   59  H31 UNL     1      -7.339  -0.992   2.428  1.00  0.00           H  
HETATM   60  H32 UNL     1      -5.746   1.859   0.022  1.00  0.00           H  
HETATM   61  H33 UNL     1      -6.254   2.402   1.681  1.00  0.00           H  
HETATM   62  H34 UNL     1      -4.558   1.017   2.685  1.00  0.00           H  
HETATM   63  H35 UNL     1      -3.896   2.177   1.423  1.00  0.00           H  
HETATM   64  H36 UNL     1      -3.491  -0.706   2.884  1.00  0.00           H  
HETATM   65  H37 UNL     1      -2.895  -1.774   1.545  1.00  0.00           H  
HETATM   66  H38 UNL     1      -4.615  -1.717   1.940  1.00  0.00           H  
HETATM   67  H39 UNL     1      -2.686   1.515  -0.042  1.00  0.00           H  
HETATM   68  H40 UNL     1      -1.338  -0.498   1.834  1.00  0.00           H  
HETATM   69  H41 UNL     1      -1.773   1.174   2.200  1.00  0.00           H  
HETATM   70  H42 UNL     1      -0.556   1.977   0.188  1.00  0.00           H  
HETATM   71  H43 UNL     1       0.540   1.267   1.487  1.00  0.00           H  
HETATM   72  H44 UNL     1      -0.731  -1.858   0.057  1.00  0.00           H  
HETATM   73  H45 UNL     1       0.995  -1.984  -0.215  1.00  0.00           H  
HETATM   74  H46 UNL     1       0.458  -1.320   1.350  1.00  0.00           H  
CONECT    1    2   29   30   31
CONECT    2    3    4   32
CONECT    3   33   34   35
CONECT    4    5   36   37
CONECT    5    6   38   39
CONECT    6    7   40   41
CONECT    7    8    9   42
CONECT    8   43   44   45
CONECT    9   10   27   46
CONECT   10   11   47   48
CONECT   11   12   49   50
CONECT   12   13   27   51
CONECT   13   14   14   24
CONECT   14   15   52
CONECT   15   16   53   54
CONECT   16   17   22   55
CONECT   17   18   56   57
CONECT   18   19   20   58
CONECT   19   59
CONECT   20   21   60   61
CONECT   21   22   62   63
CONECT   22   23   24
CONECT   23   64   65   66
CONECT   24   25   67
CONECT   25   26   68   69
CONECT   26   27   70   71
CONECT   27   28
CONECT   28   72   73   74
END

HMDB0001170
     RDKit          3D
Lathosterol
 74 77  0  0  0  0  0  0  0  0999 V2000
    7.5759    0.3899   -1.1526 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4017   -0.2832   -0.5110 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8493   -1.4639    0.3567 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7099    0.7594    0.3735 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5205    0.2069    1.0526 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3629   -0.2550    0.2382 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6515    0.8020   -0.4678 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4898    1.5621   -1.4462 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3678    0.4618   -1.1098 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3348   -0.5848   -2.1598 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1589   -0.9364   -2.3189 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8113    0.0566   -1.4109 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0986   -0.3224   -0.8592 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8347   -1.3204   -1.3693 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1555   -1.6867   -0.7864 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8053   -0.4258   -0.2181 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.1985   -0.7283    0.2516 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7357    0.3376    1.1796 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.8020   -0.1469    2.4633 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8862    1.5630    1.0673 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4845    1.2420    1.6029 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8986    0.0547    0.8631 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.7089   -1.0882    1.8724 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5810    0.4430    0.3055 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5016    0.4943    1.3655 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2422    1.0575    0.7541 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2210    0.0551   -0.2566 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2619   -1.3469    0.2748 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4307    1.4678   -1.3428 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5257    0.2497   -0.5943 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7318   -0.0811   -2.1554 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6755   -0.6956   -1.2208 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8523   -1.1243    1.4326 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8738   -1.7237    0.0895 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1439   -2.3132    0.2812 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6372    1.7377   -0.0854 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4862    0.9179    1.2091 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8730   -0.5916    1.7676 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1782    1.0227    1.7821 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7320   -0.8677    0.9312 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7908   -0.9835   -0.5192 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3627    1.5993    0.3180 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8100    1.8403   -2.3411 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7672    2.5986   -1.0886 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2978    1.0123   -1.9087 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0177    1.4158   -1.6338 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9388   -1.4725   -1.9615 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7005   -0.1421   -3.1150 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3462   -1.9833   -2.0719 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4698   -0.7702   -3.3706 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8537    1.0426   -1.8815 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4576   -1.8568   -2.2099 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8005   -2.0332   -1.6151 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0884   -2.4987   -0.0396 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8267    0.3091   -1.0380 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8528   -0.7338   -0.6446 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3108   -1.7031    0.7368 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7770    0.6493    0.8705 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3386   -0.9915    2.4284 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7461    1.8587    0.0217 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2543    2.4024    1.6805 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5577    1.0171    2.6853 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8962    2.1765    1.4226 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4911   -0.7064    2.8836 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8946   -1.7742    1.5448 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6152   -1.7166    1.9395 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6861    1.5153   -0.0422 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3379   -0.4975    1.8343 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7733    1.1736    2.1997 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5563    1.9771    0.1883 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5396    1.2667    1.4865 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7314   -1.8583    0.0565 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9950   -1.9843   -0.2151 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4581   -1.3200    1.3501 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  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  0
  3 33  1  0
  3 34  1  0
  3 35  1  0
  4 36  1  0
  4 37  1  0
  5 38  1  0
  5 39  1  0
  6 40  1  0
  6 41  1  0
  7 42  1  1
  8 43  1  0
  8 44  1  0
  8 45  1  0
  9 46  1  6
 10 47  1  0
 10 48  1  0
 11 49  1  0
 11 50  1  0
 12 51  1  6
 14 52  1  0
 15 53  1  0
 15 54  1  0
 16 55  1  6
 17 56  1  0
 17 57  1  0
 18 58  1  6
 19 59  1  0
 20 60  1  0
 20 61  1  0
 21 62  1  0
 21 63  1  0
 23 64  1  0
 23 65  1  0
 23 66  1  0
 24 67  1  6
 25 68  1  0
 25 69  1  0
 26 70  1  0
 26 71  1  0
 28 72  1  0
 28 73  1  0
 28 74  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
gamma-Cholesterol	ChEBI
5alpha-Cholest-7-en-3beta-ol	Kegg
g-Cholesterol	Generator
Γ-cholesterol	Generator
5a-Cholest-7-en-3b-ol	Generator
5Α-cholest-7-en-3β-ol	Generator
(3beta)-Cholest-7-en-3-ol	HMDB
(3beta,5alpha)-Cholest-7-en-3-ol	HMDB
(3beta,alpha)-Cholest-7-en-3-ol	HMDB
(7)-Cholestenol	HMDB
3b-Hydroxy-5-cholestene	HMDB
3beta-Hydroxy-5alpha-cholest-7-ene	HMDB
5-a-Cholest-7-en-3-beta-ol	HMDB
5-alpha-Cholest-7-en-3-beta-ol	HMDB
7-Cholesten-3-beta-ol	HMDB
7-Cholestenol	HMDB
7-Cholesterol	HMDB
Cholest-7-en-3-ol	HMDB
Cholest-7-en-3beta-ol	HMDB
Cholest-7-en-ol	HMDB
Cholesterol - synthetic	HMDB
Cholesterol extra pure	HMDB
Cholesterol GR	HMDB
Cholesterol pharma	HMDB
Cholesterol,NF grade	HMDB
delta(7)-Cholestenol	HMDB
DELTA7-Cholesten-3beta-ol	HMDB
DELTA7-Cholestenol	HMDB
gamma-Cholestenol	HMDB
Lathosterol	ChEBI

Chemical Formula

C₂₇H₄₆O

Average Molecular Weight

386.6535

Monoisotopic Molecular Weight

386.354866094

IUPAC Name

(1R,2S,5S,7S,11R,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-9-en-5-ol

Traditional Name

(1R,2S,5S,7S,11R,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-9-en-5-ol

CAS Registry Number

80-99-9

SMILES

[H][C@@]1(CC[C@@]2([H])C3=CC[C@@]4([H])C[C@@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCCC(C)C

InChI Identifier

InChI=1S/C27H46O/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/h10,18-21,23-25,28H,6-9,11-17H2,1-5H3/t19-,20+,21+,23-,24+,25+,26+,27-/m1/s1

InChI Key

IZVFFXVYBHFIHY-SKCNUYALSA-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
Hydroxysteroid
3-hydroxysteroid
3-hydroxy-delta-7-steroid
Delta-7-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:17168 )
3beta-sterol (CHEBI:17168 )
Cholesterol and derivatives (C01189 )
Cholesterol and derivatives (LMST01010089 )

Ontology

Physiological effect

Health effect

Metabolic disorder

Metabolic syndrome (HMDB: HMDB0001170)

Digestive system disorder

Hepatobiliary disorder

Hepatic disorder

Cirrhosis (HMDB: HMDB0001170)

Biliary disorder

Cerebrotendinous xanthomatosis (HMDB: HMDB0001170)

Adipose tissue (HMDB: HMDB0001170)
Adipose tissue (HMDB: HMDB0001170)

All Tissues (HMDB: HMDB0001170)
Eye Lens (HMDB: HMDB0001170)

Muscle tissue

Skeletal muscle (HMDB: HMDB0001170)
Skeletal muscle (HMDB: HMDB0001170)

Epithelium

Epidermis (HMDB: HMDB0001170)

Nervous tissue

Hepatic tissue (HMDB: HMDB0001170)

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 10901139)

Cellular substructure

Organelle

Endoplasmic reticulum (HMDB: HMDB0001170)

Cell

Fibroblast

Fibroblast (HMDB: HMDB0001170)

Hematocyte

Platelet (HMDB: HMDB0001170)

Tissue substructure

Muscle (HMDB: HMDB0001170)

Organ substructure

Organ

Gland

Adrenal Gland (HMDB: HMDB0001170)
Adrenal Gland (HMDB: HMDB0001170)

Excreta

Biofluid or Excreta

Feces (PMID: 24029555)
Urine (HMDB: HMDB0001170)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0001170)

Source

Endogenous

Endogenous (HMDB: HMDB0001170)

Plant

Animal

Animal (HMDB: HMDB0001170)

Exogenous

Food

Food (HMDB: HMDB0001170)

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)

Exogenous (HMDB: HMDB0001170)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0001170)

Biochemical pathway

Drug action pathway

Alendronate Action Pathway (HMDB: HMDB0001170)
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)

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0001170)
Steroid Biosynthesis (PathBank: SMP0087326)
Kandutsch-Russell Pathway (Cholesterol Biosynthesis) (PathBank: SMP0121060)

Disease pathway

Smith-Lemli-Opitz Syndrome (SLOS) (PathBank: SMP0120515)
Desmosterolosis (PathBank: SMP0120692)
Mevalonic Aciduria (PathBank: SMP0120794)
Chondrodysplasia Punctata II, X-Linked Dominant (CDPX2) (HMDB: HMDB0001170)
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)

Lipid metabolism pathway (HMDB: HMDB0001170)

Cellular process

Cell signaling (HMDB: HMDB0001170)

Biochemical process

Lipid transport (HMDB: HMDB0001170)

Multicellular process

Inflammatory response (HMDB: HMDB0001170)

Role

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	122.0 °C	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	3.5e-05 g/L	ALOGPS
logP	7.4	ALOGPS
logP	7.11	ChemAxon
logS	-7	ALOGPS
pKa (Strongest Acidic)	18.36	ChemAxon
pKa (Strongest Basic)	-1.3	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	5	ChemAxon
Refractivity	120.62 m³·mol⁻¹	ChemAxon
Polarizability	50.52 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]+	197.456	31661259
DarkChem	[M-H]-	194.731	31661259
AllCCS	[M+H]+	204.016	32859911
AllCCS	[M-H]-	202.191	32859911
DeepCCS	[M-2H]-	242.035	30932474
DeepCCS	[M+Na]+	216.245	30932474
AllCCS	[M+H]+	204.0	32859911
AllCCS	[M+H-H2O]+	201.9	32859911
AllCCS	[M+NH4]+	205.9	32859911
AllCCS	[M+Na]+	206.5	32859911
AllCCS	[M-H]-	202.2	32859911
AllCCS	[M+Na-2H]-	204.0	32859911
AllCCS	[M+HCOO]-	206.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Lathosterol	[H][C@@]1(CC[C@@]2([H])C3=CC[C@@]4([H])C[C@@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCCC(C)C	2649.1	Standard polar	33892256
Lathosterol	[H][C@@]1(CC[C@@]2([H])C3=CC[C@@]4([H])C[C@@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCCC(C)C	3200.1	Standard non polar	33892256
Lathosterol	[H][C@@]1(CC[C@@]2([H])C3=CC[C@@]4([H])C[C@@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCCC(C)C	3200.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Lathosterol,1TMS,isomer #1	CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2C3=CC[C@H]4C[C@@H](O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C	3244.0	Semi standard non polar	33892256
Lathosterol,1TBDMS,isomer #1	CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2C3=CC[C@H]4C[C@@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C	3472.3	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 - Lathosterol GC-MS (Non-derivatized) - 70eV, Positive	splash10-0ab9-1019000000-45e8f26aff61be3d325a	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Lathosterol GC-MS (1 TMS) - 70eV, Positive	splash10-0006-3004900000-efe936a9ed1a83aa429c	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Lathosterol 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 - Lathosterol 10V, Positive-QTOF	splash10-014r-0009000000-88fe25051d65e99ecb32	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lathosterol 20V, Positive-QTOF	splash10-05p9-3149000000-d25373f7179ed89b61dc	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lathosterol 40V, Positive-QTOF	splash10-0c00-6359000000-8bff83f3efe22597deab	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lathosterol 10V, Negative-QTOF	splash10-000i-0009000000-82b1527837d67c6be40a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lathosterol 20V, Negative-QTOF	splash10-000i-0009000000-e2badd995ee41a69b18f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lathosterol 40V, Negative-QTOF	splash10-0ldi-1009000000-96f6e67651380e1c959e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lathosterol 10V, Positive-QTOF	splash10-000i-0009000000-178681247f5078239898	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lathosterol 20V, Positive-QTOF	splash10-0avu-9233000000-247b9ee1da8d484a4da6	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lathosterol 40V, Positive-QTOF	splash10-0a4l-9710000000-8ebbaf147cf1232af879	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lathosterol 10V, Negative-QTOF	splash10-000i-0009000000-c037f2d2f217e99b79ac	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lathosterol 20V, Negative-QTOF	splash10-000i-0009000000-c037f2d2f217e99b79ac	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lathosterol 40V, Negative-QTOF	splash10-001i-0009000000-fbd8e8ecfb898bb732a5	2021-09-25	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Experimental 1D NMR	¹H NMR Spectrum (1D, 600 MHz, CDCl₃, experimental)	2012-12-04	Wishart Lab	View Spectrum
Experimental 2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, CDCl₃, experimental)	2012-12-05	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane (predicted from logP)
Endoplasmic reticulum

Biospecimen Locations

Blood
Feces

Tissue Locations

Adipose Tissue
Adrenal Cortex
Adrenal Gland
Adrenal Medulla
Bladder
Brain
Epidermis
Eye Lens
Fibroblasts
Intestine
Kidney
Liver
Neuron
Ovary
Pancreas
Placenta
Platelet
Prostate
Skeletal Muscle
Testis

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	9.9 +/- 7.0 uM	Adult (>18 years old)	Both	Normal	10901139	details
Blood	Detected and Quantified	5.38 +/- 0.038 uM	Adult (>18 years old)	Both	Normal	20671299	details
Blood	Detected and Quantified	2.43 +/- 0.048 uM	Adult (>18 years old)	Both	Normal	20671299	details
Blood	Detected and Quantified	<18 uM	Children (1-13 years old)	Male	Normal	24142275	details
Blood	Detected and Quantified	<0.000129 uM	Newborn (0-30 days old)	Not Specified	Normal	12189593	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	25037050	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	24029555	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	67.5 +/- 58.4 uM	Adult (>18 years old)	Both	Cerebrotendinous xanthomatosis (CTX)	10901139	details
Blood	Detected and Quantified	9.6 (5.4-13.5) uM	Adult (>18 years old)	Female	Cirrhosis	10901139	details
Blood	Detected and Quantified	81.6 uM	Children (1-13 years old)	Male	Lathosterolosis	24142275	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	27015276	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	25037050	details

Associated Disorders and Diseases

Disease References

Cerebrotendinous xanthomatosis
Halperin G, Elisaf M, Leitersdorf E, Harats D: A new method for determination of serum cholestanol by high-performance liquid chromatography with ultraviolet detection. J Chromatogr B Biomed Sci Appl. 2000 Jun 9;742(2):345-52. [PubMed:10901139 ]
Cirrhosis
Halperin G, Elisaf M, Leitersdorf E, Harats D: A new method for determination of serum cholestanol by high-performance liquid chromatography with ultraviolet detection. J Chromatogr B Biomed Sci Appl. 2000 Jun 9;742(2):345-52. [PubMed:10901139 ]
Lathosterolosis
Ho AC, Fung CW, Siu TS, Ma OC, Lam CW, Tam S, Wong VC: Lathosterolosis: a disorder of cholesterol biosynthesis resembling smith-lemli-opitz syndrome. JIMD Rep. 2014;12:129-34. doi: 10.1007/8904_2013_255. Epub 2013 Oct 20. [PubMed:24142275 ]
Colorectal cancer
Sinha R, Ahn J, Sampson JN, Shi J, Yu G, Xiong X, Hayes RB, Goedert JJ: Fecal Microbiota, Fecal Metabolome, and Colorectal Cancer Interrelations. PLoS One. 2016 Mar 25;11(3):e0152126. doi: 10.1371/journal.pone.0152126. eCollection 2016. [PubMed:27015276 ] Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]

Associated OMIM IDs

213700 (Cerebrotendinous xanthomatosis)
607330 (Lathosterolosis)
114500 (Colorectal cancer)

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Wikipedia Link

METLIN ID

PubChem Compound

PDB ID

Not Available

ChEBI ID

17168

Food Biomarker Ontology

Not Available

VMH ID

LTHSTRL

MarkerDB ID

MDB00000305

Good Scents ID

Not Available

References

Synthesis Reference

Fieser, Louis F. Cholesterol and companions. III. Cholestanol, lathosterol, and ketone 104. Journal of the American Chemical Society (1953), 75 4395-403.

Material Safety Data Sheet (MSDS)

Not Available

General References

Brunetti-Pierri N, Corso G, Rossi M, Ferrari P, Balli F, Rivasi F, Annunziata I, Ballabio A, Russo AD, Andria G, Parenti G: Lathosterolosis, a novel multiple-malformation/mental retardation syndrome due to deficiency of 3beta-hydroxysteroid-delta5-desaturase. Am J Hum Genet. 2002 Oct;71(4):952-8. Epub 2002 Aug 20. [PubMed:12189593 ]
Nikkila K, Hockerstedt K, Miettinen TA: Liver transplantation modifies serum cholestanol, cholesterol precursor and plant sterol levels. Clin Chim Acta. 1992 Jun 30;208(3):205-18. [PubMed:1499139 ]
Paiva H, Thelen KM, Van Coster R, Smet J, De Paepe B, Mattila KM, Laakso J, Lehtimaki T, von Bergmann K, Lutjohann D, Laaksonen R: High-dose statins and skeletal muscle metabolism in humans: a randomized, controlled trial. Clin Pharmacol Ther. 2005 Jul;78(1):60-8. [PubMed:16003294 ]
Rioux FM, Innis SM: Cholesterol and fatty acid metabolism in piglets fed sow milk or infant formula with or without addition of cholesterol. Metabolism. 1993 Dec;42(12):1552-9. [PubMed:8246769 ]
Laaksonen R, Thelen KM, Paiva H, Matinheikki J, Vesalainen R, Janatuinen T, Knuuti J, Rontu R, von Bergmann K, Lutjohann D, Lehtimaki T: Genetic variant of the SREBF-1 gene is significantly related to cholesterol synthesis in man. Atherosclerosis. 2006 Mar;185(1):206-9. Epub 2005 Jul 11. [PubMed:16005884 ]
Lutjohann D, Harzer K, Gieselmann V, Eckhardt M: Reduced brain cholesterol content in arylsulfatase A-deficient mice. Biochem Biophys Res Commun. 2006 Jun 2;344(2):647-50. Epub 2006 Apr 7. [PubMed:16630546 ]
Hamilton JJ, Synnes A, Innis SM: Plasma cholesterol and lathosterol levels in term infants in the early neonatal period. Pediatr Res. 1992 Apr;31(4 Pt 1):396-400. [PubMed:1570206 ]
Boomsma DI, Princen HM, Frants RR, Gevers Leuven JA, Kempen HJ: Genetic analysis of indicators of cholesterol synthesis and absorption: lathosterol and phytosterols in Dutch twins and their parents. Twin Res. 2003 Aug;6(4):307-14. [PubMed:14511438 ]
Farkkila MA, Kairemo KJ, Taavitsainen MJ, Strandberg TA, Miettinen TA: Plasma lathosterol as a screening test for bile acid malabsorption due to ileal resection: correlation with 75SeHCAT test and faecal bile acid excretion. Clin Sci (Lond). 1996 Apr;90(4):315-9. [PubMed:8777839 ]

Enzymes

Enzyme Details

1. Lathosterol oxidase

General function:: Involved in iron ion binding
Specific function:: Catalyzes a dehydrogenation to introduce C5-6 double bond into lathosterol.
Gene Name:: SC5DL
Uniprot ID:: O75845
Molecular weight:: 35300.55

Reactions

Lathosterol + NAD(P)H + Oxygen → 7-Dehydrocholesterol + NAD(P)(+) + Water	details
Lathosterol + NADH + Hydrogen Ion + Oxygen → 7-Dehydrocholesterol + NAD + Water	details
Lathosterol + NADPH + Hydrogen Ion + Oxygen → 7-Dehydrocholesterol + NADP + Water	details

Enzyme Details

2. Methylsterol monooxygenase 1

General function:: Involved in iron ion binding
Specific function:: Not Available
Gene Name:: MSMO1
Uniprot ID:: Q15800
Molecular weight:: 19470.325

Enzyme Details

3. Sterol-4-alpha-carboxylate 3-dehydrogenase, decarboxylating

General function:: Involved in 3-beta-hydroxy-delta5-steroid dehydrogenase activity
Specific function:: Not Available
Gene Name:: NSDHL
Uniprot ID:: Q15738
Molecular weight:: 41899.99

Enzyme Details

4. 3-keto-steroid reductase

General function:: Involved in oxidoreductase activity
Specific function:: Responsible for the reduction of the keto group on the C-3 of sterols.
Gene Name:: HSD17B7
Uniprot ID:: P56937
Molecular weight:: 38205.77

Enzyme Details

5. 3-beta-hydroxysteroid-Delta(8),Delta(7)-isomerase

General function:: Involved in cholestenol delta-isomerase activity
Specific function:: Catalyzes the conversion of Delta(8)-sterols to their corresponding Delta(7)-isomers.
Gene Name:: EBP
Uniprot ID:: Q15125
Molecular weight:: 26352.615

Reactions

Lathosterol → 5-alpha-cholest-8-en-3-beta-ol	details
Lathosterol → 5alpha-Cholest-8-en-3beta-ol	details

Enzyme Details

6. 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

Lathosterol + NADP → 5-alpha-Cholesta-7,24-dien-3-beta-ol + NADPH	details
Lathosterol + NADP → 5alpha-Cholesta-7,24-dien-3beta-ol + NADPH + Hydrogen Ion	details

Showing metabocard for Lathosterol (HMDB0001170)

MOL for HMDB0001170 (Lathosterol)

3D MOL for HMDB0001170 (Lathosterol)

3D SDF for HMDB0001170 (Lathosterol)

3D-SDF for HMDB0001170 (Lathosterol)

PDB for HMDB0001170 (Lathosterol)

3D PDB for HMDB0001170 (Lathosterol)

SMILES for HMDB0001170 (Lathosterol)

INCHI for HMDB0001170 (Lathosterol)

Structure for HMDB0001170 (Lathosterol)

3D Structure for HMDB0001170 (Lathosterol)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes

Reactions

Reactions

Reactions