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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (6) Show 6 proteins XML

Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2022-03-07 02:48:59 UTC

HMDB ID

HMDB0000032

Secondary Accession Numbers

HMDB00032

Metabolite Identification

Common Name

7-Dehydrocholesterol

Description

7-Dehydrocholesterol (7-DHC), also known as provitamin D3 or 5,7-cholestadien-3-b-ol, belongs to the class of organic compounds known as cholesterols and derivatives. Cholesterols and derivatives are compounds containing a 3-hydroxylated cholestane core. Thus, 7-dehydrocholesterol is also classified as a sterol. 7-Dehydrocholesterol is known as a zoosterol, meaning that it is a sterol isolated from animals (to distinguish those sterols isolated from plants which are called phytosterols). 7-DHC functions in the serum as a cholesterol precursor and is photochemically converted to vitamin D3 in the skin. Therefore 7-DHC functions as provitamin-D3. The presence of 7-DHC in human skin enables humans and other mammals to manufacture vitamin D3 (cholecalciferol) from ultraviolet rays in the sun light, via an intermediate isomer pre-vitamin D3. 7-DHC absorbs UV light most effectively at wavelengths between 290 and 320 nm and, thus, the production of vitamin D3 will occur primarily at those wavelengths (PMID: 9625080 ). The two most important factors that govern the generation of pre-vitamin D3 are the quantity (intensity) and quality (appropriate wavelength) of the UVB irradiation reaching the 7-dehydrocholesterol deep in the stratum basale and stratum spinosum (PMID: 9625080 ). 7-DHC is also found in the milk of several mammalian species, including cows (PMID: 10999630 ; PMID: 225459 ). It was discovered by Nobel-laureate organic chemist Adolf Windaus. 7-DHC can be produced by animals and plants via different pathways (PMID: 23717318 ). It is not produced by fungi in significant amounts. 7-DHC is made by some algae and can also be produced by some bacteria.

Structure

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

      
  Mrv1652308122017252D          

 31 34  0  0  0  0            999 V2000
 9999.976110001.2192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.8390 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
 9998.5515 9998.7390    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9999.9761 9998.7390    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9997.1260 9999.5578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.4115 9999.1453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.4115 9998.3202    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9997.1260 9997.9078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.8374 9999.1453    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9997.8374 9998.3202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.5518 9997.9078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.2664 9998.3202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.264410000.8030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.549910000.3906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.5499 9999.5655    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9999.2644 9999.1531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.978910000.3905    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
10000.7634 9999.3106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.2483 9999.9779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.763410000.6455    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10000.763410001.4705    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10001.479210001.8810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.192710001.4705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.908510001.8810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.624210001.4705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.337810001.8810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.624210000.6455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.049910001.8810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.479210001.0560    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
  8  3  1  1  0  0  0
  6 10  1  0  0  0  0
  9 11  1  0  0  0  0
 10  2  1  1  0  0  0
 16 10  1  0  0  0  0
 13 17  2  0  0  0  0
 16  4  1  6  0  0  0
 22 23  1  0  0  0  0
 22 31  1  6  0  0  0
 23 24  1  0  0  0  0
 23 30  1  6  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 29  1  0  0  0  0
 22 18  1  0  0  0  0
 22 21  1  0  0  0  0
 14 18  1  0  0  0  0
 17 19  1  0  0  0  0
 19  5  1  6  0  0  0
 18  1  1  1  0  0  0
M  END

HMDB0000032
     RDKit          3D
7-Dehydrocholesterol
 72 75  0  0  0  0  0  0  0  0999 V2000
    8.0566    0.9921    0.0828 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7528    0.2078   -0.0687 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0057   -1.2075    0.4024 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7199    0.9012    0.7895 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3782    0.2190    0.7255 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8188    0.1822   -0.6671 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4745   -0.5072   -0.7156 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6370   -1.9004   -0.2310 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4942    0.3253    0.0444 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4526    1.6941   -0.6518 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0213    2.1667   -0.5997 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6243    1.2048    0.3264 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0837    1.0171    0.1187 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7341    1.9005   -0.5682 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1763    1.7339   -0.7913 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7802    0.6804   -0.2887 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2607    0.5501   -0.5413 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9295    0.4877    0.8095 C   0  0  1  0  0  0  0  0  0  0  0  0
   -8.2934    0.2119    0.5576 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3548   -0.7134    1.5337 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8933   -0.6019    1.7586 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1116   -0.3737    0.4537 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.2223   -1.6728   -0.3824 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6969   -0.1372    0.7396 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8747   -1.4090    0.5579 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3956   -1.1413    0.8645 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0758   -0.1057   -0.0877 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3229   -0.4285   -1.5078 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8553    0.5602   -0.5662 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3777    0.9798    1.1442 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9301    2.0444   -0.2421 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4724    0.1574   -1.1328 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8796   -1.5942   -0.1915 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1675   -1.8854    0.1535 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2900   -1.2633    1.4676 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0628    0.8462    1.8419 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6009    1.9604    0.5276 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6945    0.8466    1.3605 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4611   -0.7542    1.2053 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4926   -0.2462   -1.4072 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6278    1.2443   -0.9848 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1311   -0.5482   -1.7688 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9178   -2.5730   -0.7582 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6075   -2.0215    0.8654 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6498   -2.2596   -0.5478 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7150    0.4785    1.0982 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1540    2.3975   -0.1651 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7274    1.5666   -1.7185 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0224    3.2234   -0.2621 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4636    2.1017   -1.6106 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4124    1.4521    1.3673 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2967    2.7985   -1.0191 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7582    2.4675   -1.3663 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4991   -0.3767   -1.0860 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6427    1.3992   -1.1535 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8324    1.3957    1.4057 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3200   -0.5866   -0.0381 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5933   -1.6441    0.9950 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8721   -0.7878    2.5160 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6030    0.2034    2.4418 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5382   -1.5546    2.2089 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7018   -1.5006   -1.3231 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7789   -2.5029    0.1573 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2989   -1.9291   -0.5419 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6387    0.0056    1.8975 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2042   -2.1198    1.3333 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9264   -1.8463   -0.4295 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1040   -2.1144    0.7994 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2713   -0.7848    1.9090 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4200   -0.2289   -1.5955 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1767    0.2137   -2.2461 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1341   -1.4968   -1.7440 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  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
  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  6
  8 43  1  0
  8 44  1  0
  8 45  1  0
  9 46  1  1
 10 47  1  0
 10 48  1  0
 11 49  1  0
 11 50  1  0
 12 51  1  1
 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

      
  Mrv1652308122017252D          

 31 34  0  0  0  0            999 V2000
 9999.976110001.2192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.8390 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
 9998.5515 9998.7390    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9999.9761 9998.7390    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9997.1260 9999.5578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.4115 9999.1453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.4115 9998.3202    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9997.1260 9997.9078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.8374 9999.1453    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9997.8374 9998.3202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.5518 9997.9078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.2664 9998.3202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.264410000.8030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.549910000.3906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.5499 9999.5655    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9999.2644 9999.1531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.978910000.3905    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
10000.7634 9999.3106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.2483 9999.9779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.763410000.6455    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10000.763410001.4705    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10001.479210001.8810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.192710001.4705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.908510001.8810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.624210001.4705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.337810001.8810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.624210000.6455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.049910001.8810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.479210001.0560    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
  8  3  1  1  0  0  0
  6 10  1  0  0  0  0
  9 11  1  0  0  0  0
 10  2  1  1  0  0  0
 16 10  1  0  0  0  0
 13 17  2  0  0  0  0
 16  4  1  6  0  0  0
 22 23  1  0  0  0  0
 22 31  1  6  0  0  0
 23 24  1  0  0  0  0
 23 30  1  6  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 29  1  0  0  0  0
 22 18  1  0  0  0  0
 22 21  1  0  0  0  0
 14 18  1  0  0  0  0
 17 19  1  0  0  0  0
 19  5  1  6  0  0  0
 18  1  1  1  0  0  0
M  END
> <DATABASE_ID>
HMDB0000032

> <DATABASE_NAME>
hmdb

> <SMILES>
[H][C@@]1(CC[C@@]2([H])C3=CC=C4C[C@@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCCC(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/h9-10,18-19,21,23-25,28H,6-8,11-17H2,1-5H3/t19-,21+,23-,24+,25+,26+,27-/m1/s1

> <INCHI_KEY>
UCTLRSWJYQTBFZ-DDPQNLDTSA-N

> <FORMULA>
C27H44O

> <MOLECULAR_WEIGHT>
384.6377

> <EXACT_MASS>
384.33921603

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
72

> <JCHEM_AVERAGE_POLARIZABILITY>
50.01447282690572

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
7.30

> <JCHEM_LOGP>
6.707309549333335

> <ALOGPS_LOGS>
-6.41

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.270805421445605

> <JCHEM_PKA_STRONGEST_BASIC>
-1.3681497086596925

> <JCHEM_POLAR_SURFACE_AREA>
20.23

> <JCHEM_REFRACTIVITY>
121.46649999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.48e-04 g/l

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

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0000032
     RDKit          3D
7-Dehydrocholesterol
 72 75  0  0  0  0  0  0  0  0999 V2000
    8.0566    0.9921    0.0828 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7528    0.2078   -0.0687 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0057   -1.2075    0.4024 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7199    0.9012    0.7895 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3782    0.2190    0.7255 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8188    0.1822   -0.6671 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4745   -0.5072   -0.7156 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6370   -1.9004   -0.2310 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4942    0.3253    0.0444 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4526    1.6941   -0.6518 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0213    2.1667   -0.5997 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6243    1.2048    0.3264 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0837    1.0171    0.1187 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7341    1.9005   -0.5682 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1763    1.7339   -0.7913 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7802    0.6804   -0.2887 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2607    0.5501   -0.5413 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9295    0.4877    0.8095 C   0  0  1  0  0  0  0  0  0  0  0  0
   -8.2934    0.2119    0.5576 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3548   -0.7134    1.5337 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8933   -0.6019    1.7586 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1116   -0.3737    0.4537 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.2223   -1.6728   -0.3824 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6969   -0.1372    0.7396 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8747   -1.4090    0.5579 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3956   -1.1413    0.8645 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0758   -0.1057   -0.0877 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3229   -0.4285   -1.5078 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8553    0.5602   -0.5662 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3777    0.9798    1.1442 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9301    2.0444   -0.2421 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4724    0.1574   -1.1328 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8796   -1.5942   -0.1915 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1675   -1.8854    0.1535 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2900   -1.2633    1.4676 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0628    0.8462    1.8419 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6009    1.9604    0.5276 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6945    0.8466    1.3605 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4611   -0.7542    1.2053 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4926   -0.2462   -1.4072 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6278    1.2443   -0.9848 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1311   -0.5482   -1.7688 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9178   -2.5730   -0.7582 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6075   -2.0215    0.8654 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6498   -2.2596   -0.5478 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7150    0.4785    1.0982 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1540    2.3975   -0.1651 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7274    1.5666   -1.7185 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0224    3.2234   -0.2621 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4636    2.1017   -1.6106 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4124    1.4521    1.3673 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2967    2.7985   -1.0191 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7582    2.4675   -1.3663 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4991   -0.3767   -1.0860 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6427    1.3992   -1.1535 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8324    1.3957    1.4057 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3200   -0.5866   -0.0381 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5933   -1.6441    0.9950 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8721   -0.7878    2.5160 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6030    0.2034    2.4418 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5382   -1.5546    2.2089 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7018   -1.5006   -1.3231 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7789   -2.5029    0.1573 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2989   -1.9291   -0.5419 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6387    0.0056    1.8975 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2042   -2.1198    1.3333 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9264   -1.8463   -0.4295 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1040   -2.1144    0.7994 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2713   -0.7848    1.9090 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4200   -0.2289   -1.5955 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1767    0.2137   -2.2461 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1341   -1.4968   -1.7440 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  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
  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  6
  8 43  1  0
  8 44  1  0
  8 45  1  0
  9 46  1  1
 10 47  1  0
 10 48  1  0
 11 49  1  0
 11 50  1  0
 12 51  1  1
 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                                 12-AUG-20   NONE
TITLE     NULL                                                        
COMPND    MOLECULE:                                                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-AUG-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    8663.9638664.313   0.000  0.00  0.00           H+0
HETATM    5  H   UNK     0    8666.6228664.313   0.000  0.00  0.00           H+0
HETATM    6  C   UNK     0    8661.3028665.841   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    8659.9688665.071   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8659.9688663.531   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8661.3028662.761   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8662.6308665.071   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8662.6308663.531   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8663.9638662.761   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8665.2978663.531   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8665.2948668.166   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8663.9608667.396   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8663.9608665.856   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8665.2948665.086   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    8666.6278667.396   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0    8666.6278665.856   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0    8668.0928665.380   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0    8668.9978666.625   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0    8668.0928667.872   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0    8668.0928669.412   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0    8669.4288670.178   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0    8670.7608669.412   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0    8672.0968670.178   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0    8673.4328669.412   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0    8674.7648670.178   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0    8673.4328667.872   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0    8666.7608670.178   0.000  0.00  0.00           C+0
HETATM   31  H   UNK     0    8669.4288668.638   0.000  0.00  0.00           H+0
CONECT    1   18                                                            
CONECT    2   10                                                            
CONECT    3    8                                                            
CONECT    4   16                                                            
CONECT    5   19                                                            
CONECT    6    7   10                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9    3                                                  
CONECT    9    8   11                                                       
CONECT   10   11    6    2   16                                             
CONECT   11   10   12    9                                                  
CONECT   12   11   13                                                       
CONECT   13   12   17                                                       
CONECT   14   15   18                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   10    4                                             
CONECT   17   16   13   19                                                  
CONECT   18   19   22   14    1                                             
CONECT   19   18   20   17    5                                             
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   23   31   18   21                                             
CONECT   23   22   24   30                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27                                                            
CONECT   30   23                                                            
CONECT   31   22                                                            
MASTER        0    0    0    0    0    0    0    0   31    0   68    0
END

COMPND    HMDB0000032
HETATM    1  C1  UNL     1       8.057   0.992   0.083  1.00  0.00           C  
HETATM    2  C2  UNL     1       6.753   0.208  -0.069  1.00  0.00           C  
HETATM    3  C3  UNL     1       7.006  -1.207   0.402  1.00  0.00           C  
HETATM    4  C4  UNL     1       5.720   0.901   0.789  1.00  0.00           C  
HETATM    5  C5  UNL     1       4.378   0.219   0.726  1.00  0.00           C  
HETATM    6  C6  UNL     1       3.819   0.182  -0.667  1.00  0.00           C  
HETATM    7  C7  UNL     1       2.475  -0.507  -0.716  1.00  0.00           C  
HETATM    8  C8  UNL     1       2.637  -1.900  -0.231  1.00  0.00           C  
HETATM    9  C9  UNL     1       1.494   0.325   0.044  1.00  0.00           C  
HETATM   10  C10 UNL     1       1.453   1.694  -0.652  1.00  0.00           C  
HETATM   11  C11 UNL     1       0.021   2.167  -0.600  1.00  0.00           C  
HETATM   12  C12 UNL     1      -0.624   1.205   0.326  1.00  0.00           C  
HETATM   13  C13 UNL     1      -2.084   1.017   0.119  1.00  0.00           C  
HETATM   14  C14 UNL     1      -2.734   1.900  -0.568  1.00  0.00           C  
HETATM   15  C15 UNL     1      -4.176   1.734  -0.791  1.00  0.00           C  
HETATM   16  C16 UNL     1      -4.780   0.680  -0.289  1.00  0.00           C  
HETATM   17  C17 UNL     1      -6.261   0.550  -0.541  1.00  0.00           C  
HETATM   18  C18 UNL     1      -6.929   0.488   0.810  1.00  0.00           C  
HETATM   19  O1  UNL     1      -8.293   0.212   0.558  1.00  0.00           O  
HETATM   20  C19 UNL     1      -6.355  -0.713   1.534  1.00  0.00           C  
HETATM   21  C20 UNL     1      -4.893  -0.602   1.759  1.00  0.00           C  
HETATM   22  C21 UNL     1      -4.112  -0.374   0.454  1.00  0.00           C  
HETATM   23  C22 UNL     1      -4.222  -1.673  -0.382  1.00  0.00           C  
HETATM   24  C23 UNL     1      -2.697  -0.137   0.740  1.00  0.00           C  
HETATM   25  C24 UNL     1      -1.875  -1.409   0.558  1.00  0.00           C  
HETATM   26  C25 UNL     1      -0.396  -1.141   0.865  1.00  0.00           C  
HETATM   27  C26 UNL     1       0.076  -0.106  -0.088  1.00  0.00           C  
HETATM   28  C27 UNL     1      -0.323  -0.429  -1.508  1.00  0.00           C  
HETATM   29  H1  UNL     1       8.855   0.560  -0.566  1.00  0.00           H  
HETATM   30  H2  UNL     1       8.378   0.980   1.144  1.00  0.00           H  
HETATM   31  H3  UNL     1       7.930   2.044  -0.242  1.00  0.00           H  
HETATM   32  H4  UNL     1       6.472   0.157  -1.133  1.00  0.00           H  
HETATM   33  H5  UNL     1       7.880  -1.594  -0.192  1.00  0.00           H  
HETATM   34  H6  UNL     1       6.168  -1.885   0.154  1.00  0.00           H  
HETATM   35  H7  UNL     1       7.290  -1.263   1.468  1.00  0.00           H  
HETATM   36  H8  UNL     1       6.063   0.846   1.842  1.00  0.00           H  
HETATM   37  H9  UNL     1       5.601   1.960   0.528  1.00  0.00           H  
HETATM   38  H10 UNL     1       3.695   0.847   1.360  1.00  0.00           H  
HETATM   39  H11 UNL     1       4.461  -0.754   1.205  1.00  0.00           H  
HETATM   40  H12 UNL     1       4.493  -0.246  -1.407  1.00  0.00           H  
HETATM   41  H13 UNL     1       3.628   1.244  -0.985  1.00  0.00           H  
HETATM   42  H14 UNL     1       2.131  -0.548  -1.769  1.00  0.00           H  
HETATM   43  H15 UNL     1       1.918  -2.573  -0.758  1.00  0.00           H  
HETATM   44  H16 UNL     1       2.608  -2.021   0.865  1.00  0.00           H  
HETATM   45  H17 UNL     1       3.650  -2.260  -0.548  1.00  0.00           H  
HETATM   46  H18 UNL     1       1.715   0.478   1.098  1.00  0.00           H  
HETATM   47  H19 UNL     1       2.154   2.397  -0.165  1.00  0.00           H  
HETATM   48  H20 UNL     1       1.727   1.567  -1.718  1.00  0.00           H  
HETATM   49  H21 UNL     1      -0.022   3.223  -0.262  1.00  0.00           H  
HETATM   50  H22 UNL     1      -0.464   2.102  -1.611  1.00  0.00           H  
HETATM   51  H23 UNL     1      -0.412   1.452   1.367  1.00  0.00           H  
HETATM   52  H24 UNL     1      -2.297   2.798  -1.019  1.00  0.00           H  
HETATM   53  H25 UNL     1      -4.758   2.468  -1.366  1.00  0.00           H  
HETATM   54  H26 UNL     1      -6.499  -0.377  -1.086  1.00  0.00           H  
HETATM   55  H27 UNL     1      -6.643   1.399  -1.154  1.00  0.00           H  
HETATM   56  H28 UNL     1      -6.832   1.396   1.406  1.00  0.00           H  
HETATM   57  H29 UNL     1      -8.320  -0.587  -0.038  1.00  0.00           H  
HETATM   58  H30 UNL     1      -6.593  -1.644   0.995  1.00  0.00           H  
HETATM   59  H31 UNL     1      -6.872  -0.788   2.516  1.00  0.00           H  
HETATM   60  H32 UNL     1      -4.603   0.203   2.442  1.00  0.00           H  
HETATM   61  H33 UNL     1      -4.538  -1.555   2.209  1.00  0.00           H  
HETATM   62  H34 UNL     1      -3.702  -1.501  -1.323  1.00  0.00           H  
HETATM   63  H35 UNL     1      -3.779  -2.503   0.157  1.00  0.00           H  
HETATM   64  H36 UNL     1      -5.299  -1.929  -0.542  1.00  0.00           H  
HETATM   65  H37 UNL     1      -2.639   0.006   1.898  1.00  0.00           H  
HETATM   66  H38 UNL     1      -2.204  -2.120   1.333  1.00  0.00           H  
HETATM   67  H39 UNL     1      -1.926  -1.846  -0.429  1.00  0.00           H  
HETATM   68  H40 UNL     1       0.104  -2.114   0.799  1.00  0.00           H  
HETATM   69  H41 UNL     1      -0.271  -0.785   1.909  1.00  0.00           H  
HETATM   70  H42 UNL     1      -1.420  -0.229  -1.596  1.00  0.00           H  
HETATM   71  H43 UNL     1       0.177   0.214  -2.246  1.00  0.00           H  
HETATM   72  H44 UNL     1      -0.134  -1.497  -1.744  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   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

HMDB0000032
     RDKit          3D
7-Dehydrocholesterol
 72 75  0  0  0  0  0  0  0  0999 V2000
    8.0566    0.9921    0.0828 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7528    0.2078   -0.0687 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0057   -1.2075    0.4024 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7199    0.9012    0.7895 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3782    0.2190    0.7255 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8188    0.1822   -0.6671 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4745   -0.5072   -0.7156 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6370   -1.9004   -0.2310 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4942    0.3253    0.0444 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4526    1.6941   -0.6518 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0213    2.1667   -0.5997 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6243    1.2048    0.3264 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0837    1.0171    0.1187 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7341    1.9005   -0.5682 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1763    1.7339   -0.7913 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7802    0.6804   -0.2887 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2607    0.5501   -0.5413 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9295    0.4877    0.8095 C   0  0  1  0  0  0  0  0  0  0  0  0
   -8.2934    0.2119    0.5576 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3548   -0.7134    1.5337 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8933   -0.6019    1.7586 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1116   -0.3737    0.4537 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.2223   -1.6728   -0.3824 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6969   -0.1372    0.7396 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8747   -1.4090    0.5579 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3956   -1.1413    0.8645 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0758   -0.1057   -0.0877 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3229   -0.4285   -1.5078 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8553    0.5602   -0.5662 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3777    0.9798    1.1442 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9301    2.0444   -0.2421 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4724    0.1574   -1.1328 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8796   -1.5942   -0.1915 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1675   -1.8854    0.1535 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2900   -1.2633    1.4676 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0628    0.8462    1.8419 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6009    1.9604    0.5276 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6945    0.8466    1.3605 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4611   -0.7542    1.2053 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4926   -0.2462   -1.4072 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6278    1.2443   -0.9848 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1311   -0.5482   -1.7688 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9178   -2.5730   -0.7582 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6075   -2.0215    0.8654 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6498   -2.2596   -0.5478 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7150    0.4785    1.0982 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1540    2.3975   -0.1651 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7274    1.5666   -1.7185 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0224    3.2234   -0.2621 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4636    2.1017   -1.6106 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4124    1.4521    1.3673 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2967    2.7985   -1.0191 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7582    2.4675   -1.3663 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4991   -0.3767   -1.0860 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6427    1.3992   -1.1535 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8324    1.3957    1.4057 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3200   -0.5866   -0.0381 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5933   -1.6441    0.9950 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8721   -0.7878    2.5160 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6030    0.2034    2.4418 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5382   -1.5546    2.2089 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7018   -1.5006   -1.3231 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7789   -2.5029    0.1573 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2989   -1.9291   -0.5419 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6387    0.0056    1.8975 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2042   -2.1198    1.3333 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9264   -1.8463   -0.4295 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1040   -2.1144    0.7994 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2713   -0.7848    1.9090 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4200   -0.2289   -1.5955 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1767    0.2137   -2.2461 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1341   -1.4968   -1.7440 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  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
  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  6
  8 43  1  0
  8 44  1  0
  8 45  1  0
  9 46  1  1
 10 47  1  0
 10 48  1  0
 11 49  1  0
 11 50  1  0
 12 51  1  1
 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
(3beta)-Cholesta-5,7-dien-3-ol	ChEBI
5,7-Cholestadien-3-beta-ol	ChEBI
5,7-Cholestadien-3beta-ol	ChEBI
Provitamin D3	ChEBI
Cholesta-5,7-dien-3beta-ol	Kegg
(3b)-Cholesta-5,7-dien-3-ol	Generator
(3Β)-cholesta-5,7-dien-3-ol	Generator
5,7-Cholestadien-3-b-ol	Generator
5,7-Cholestadien-3-β-ol	Generator
5,7-Cholestadien-3b-ol	Generator
5,7-Cholestadien-3β-ol	Generator
Cholesta-5,7-dien-3b-ol	Generator
Cholesta-5,7-dien-3β-ol	Generator
(-)-7-Dehydrocholesterol	HMDB
10,13-Dimethyl-17-(6-methylheptan-2-yl)-2,3,4,9,11,12,14,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-3-ol	HMDB
17-(1,5-Dimethylhexyl)-10,13-dimethyl-2,3,4,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol	HMDB
5,7-Cholestandien-3-ol	HMDB
5,7-Cholestandien-3beta-ol	HMDB
7,8-Dehydro-cholesterol	HMDB
7,8-Didehydrocholesterol	HMDB
7-Dehydro-cholesterol	HMDB
7-Dehydrocholesterin	HMDB
7DHC	HMDB
Cholesta-5,7-dien-3 beta -ol	HMDB
Cholesta-5,7-dien-3-beta-ol	HMDB
Cholesta-5,7-dien-3-ol	HMDB
Dehydrocholesterin	HMDB
Dehydrocholesterol	HMDB
Delta5,7-Cholestadien-3beta-ol	HMDB
Delta5,7-Cholesterol	HMDB
Delta7-Cholesterol	HMDB
Provitamin-D3	HMDB
Provitamin D(3)	HMDB
Cholesta-5,7-dien-3 beta-ol	HMDB
7-Dehydrocholesterol, (3beta,10alpha)-isomer	HMDB
7-Dehydrocholesterol, (3beta,9beta,10alpha)-isomer	HMDB
7-DHC	HMDB
7-Dehydrocholesterol, (3alpha)-isomer	HMDB
7-Dehydrocholesterol, (3beta,9beta)-isomer	HMDB

Chemical Formula

C₂₇H₄₄O

Average Molecular Weight

384.6377

Monoisotopic Molecular Weight

384.33921603

IUPAC Name

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

Traditional Name

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

CAS Registry Number

434-16-2

SMILES

[H][C@@]1(CC[C@@]2([H])C3=CC=C4C[C@@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCCC(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/h9-10,18-19,21,23-25,28H,6-8,11-17H2,1-5H3/t19-,21+,23-,24+,25+,26+,27-/m1/s1

InChI Key

UCTLRSWJYQTBFZ-DDPQNLDTSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cholesterols and derivatives. Cholesterols and derivatives are compounds containing a 3-hydroxylated cholestane core.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Cholestane steroids

Direct Parent

Cholesterols and derivatives

Alternative Parents

Substituents

Cholesterol
Cholesterol-skeleton
3-hydroxy-delta-5-steroid
3-hydroxy-delta-7-steroid
3-beta-hydroxysteroid
3-beta-hydroxy-delta-5-steroid
3-hydroxysteroid
Hydroxysteroid
Delta-7-steroid
Delta-5-steroid
Cyclic alcohol
Secondary alcohol
Alcohol
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

cholestanoid (CHEBI:17759 )
3beta-sterol (CHEBI:17759 )
Vitamin D3 and derivatives (C01164 )
Cholestane and derivatives (C01164 )
Cholesterol and derivatives (LMST01010069 )

Ontology

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	150.5 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	1 mg/mL	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.00015 g/L	ALOGPS
logP	7.3	ALOGPS
logP	6.71	ChemAxon
logS	-6.4	ALOGPS
pKa (Strongest Acidic)	18.27	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	5	ChemAxon
Refractivity	121.47 m³·mol⁻¹	ChemAxon
Polarizability	50.01 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]+	196.513	31661259
DarkChem	[M-H]-	192.74	31661259
AllCCS	[M+H]+	203.495	32859911
AllCCS	[M-H]-	203.026	32859911
DeepCCS	[M-2H]-	243.645	30932474
DeepCCS	[M+Na]+	218.254	30932474
AllCCS	[M+H]+	203.5	32859911
AllCCS	[M+H-H2O]+	201.3	32859911
AllCCS	[M+NH4]+	205.6	32859911
AllCCS	[M+Na]+	206.1	32859911
AllCCS	[M-H]-	203.0	32859911
AllCCS	[M+Na-2H]-	204.7	32859911
AllCCS	[M+HCOO]-	206.7	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
7-Dehydrocholesterol	[H][C@@]1(CC[C@@]2([H])C3=CC=C4C[C@@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCCC(C)C	2963.9	Standard polar	33892256
7-Dehydrocholesterol	[H][C@@]1(CC[C@@]2([H])C3=CC=C4C[C@@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCCC(C)C	3157.3	Standard non polar	33892256
7-Dehydrocholesterol	[H][C@@]1(CC[C@@]2([H])C3=CC=C4C[C@@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCCC(C)C	3122.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
7-Dehydrocholesterol,1TMS,isomer #1	CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2C3=CC=C4C[C@@H](O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C	3254.1	Semi standard non polar	33892256
7-Dehydrocholesterol,1TBDMS,isomer #1	CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2C3=CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C	3489.4	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 - 7-Dehydrocholesterol GC-MS (Non-derivatized) - 70eV, Positive	splash10-0axr-1019000000-73894a6c7b7346b2d1b0	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 7-Dehydrocholesterol GC-MS (1 TMS) - 70eV, Positive	splash10-002f-3005900000-c63a75d6ed190e98a35b	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 7-Dehydrocholesterol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 7-Dehydrocholesterol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 7-Dehydrocholesterol GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - 7-Dehydrocholesterol Quattro_QQQ 10V, Positive-QTOF (Annotated)	splash10-000i-0009000000-124abe0c8995f883f002	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 7-Dehydrocholesterol Quattro_QQQ 25V, Positive-QTOF (Annotated)	splash10-05oa-4942000000-dbfe3e996983256b1e0c	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 7-Dehydrocholesterol Quattro_QQQ 40V, Positive-QTOF (Annotated)	splash10-05o0-5900000000-8115f37d8da9a1d6f5d8	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 7-Dehydrocholesterol n/a 26V, negative-QTOF	splash10-000i-0090000000-3645f0c0605ff7c97405	2020-07-21	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7-Dehydrocholesterol 10V, Positive-QTOF	splash10-014r-0019000000-d2b535e3c3ed257f2215	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7-Dehydrocholesterol 20V, Positive-QTOF	splash10-0ar9-3139000000-87132b4b12416fa4f01e	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7-Dehydrocholesterol 40V, Positive-QTOF	splash10-0a4i-5249000000-257a8915fd5fab2dfaaa	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7-Dehydrocholesterol 10V, Negative-QTOF	splash10-001i-0009000000-8ff4cced50a3c638abba	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7-Dehydrocholesterol 20V, Negative-QTOF	splash10-001i-0009000000-6d9a73d8f487e848e538	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7-Dehydrocholesterol 40V, Negative-QTOF	splash10-0ldi-1019000000-eb1f58f2c9df95716640	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7-Dehydrocholesterol 10V, Positive-QTOF	splash10-000i-0009000000-5cafb4a46516e1c4ca5a	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7-Dehydrocholesterol 20V, Positive-QTOF	splash10-0ktr-9168000000-27f4addc4e70c9e3fc88	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7-Dehydrocholesterol 40V, Positive-QTOF	splash10-052f-9510000000-fce215a9f0a5b16bb81c	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7-Dehydrocholesterol 10V, Negative-QTOF	splash10-001i-0009000000-4d7a5f3b63c0fb62f1d7	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7-Dehydrocholesterol 20V, Negative-QTOF	splash10-001i-0009000000-4d7a5f3b63c0fb62f1d7	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7-Dehydrocholesterol 40V, Negative-QTOF	splash10-001i-0009000000-cf419f92ab7dfef8f2f8	2021-09-25	Wishart Lab	View Spectrum

NMR Spectra

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

Biological Properties

Cellular Locations

Cytoplasm
Extracellular
Membrane
Endoplasmic reticulum

Biospecimen Locations

Blood
Cerebrospinal Fluid (CSF)
Urine

Tissue Locations

Adrenal Gland
Brain
Epidermis
Fibroblasts
Liver
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	<0.65 uM	Children (1-13 years old)	Male	Normal	24142275	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Blood	Detected and Quantified	5.0 +/- 2.2 uM	Adult (>18 years old)	Both	Normal	11590227	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0 - 0.02 uM	Adult (>18 years old)	Both	Normal	10946022	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Urine	Detected and Quantified	0.029 (0.0068-0.051) umol/mmol creatinine	Adult (>18 years old)	Both	Normal	16451140	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.21 uM	Children (1-13 years old)	Male	Lathosterolosis	24142275	details
Blood	Detected and Quantified	369.0 (46.0 - 1220.0) uM	Adult (>18 years old)	Both	Smith-Lemli-Opitz syndrome	11590227	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.3 +/- 0.2 (0.1 - 0.6) uM	Infant (0-1 year old)	Both	Smith-Lemli-Opitz syndrome	9266395	details

Associated Disorders and Diseases

Disease References

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 ]
Smith-Lemli-Opitz syndrome
van Rooij A, Nijenhuis AA, Wijburg FA, Schutgens RB: Highly increased CSF concentrations of cholesterol precursors in Smith-Lemli-Opitz syndrome. J Inherit Metab Dis. 1997 Aug;20(4):578-80. [PubMed:9266395 ] Johnson DW, ten Brink HJ, Jakobs C: A rapid screening procedure for cholesterol and dehydrocholesterol by electrospray ionization tandem mass spectrometry. J Lipid Res. 2001 Oct;42(10):1699-705. [PubMed:11590227 ]

Associated OMIM IDs

607330 (Lathosterolosis)
270400 (Smith-Lemli-Opitz syndrome)

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB021882

KNApSAcK ID

C00023747

Chemspider ID

Not Available

KEGG Compound ID

C01164

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

7-Dehydrocholesterol

METLIN ID

Not Available

PubChem Compound

439423

PDB ID

Not Available

ChEBI ID

17759

Food Biomarker Ontology

Not Available

VMH ID

7DHCHSTEROL

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

William G. Dauben, Jerome F. Eastham, and Robert A. Micheli A new method for the preparation of 7-dehydrocholesterol. Journal of the American Chemical Society (1951), 73 4496.

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Lehmann B, Genehr T, Knuschke P, Pietzsch J, Meurer M: UVB-induced conversion of 7-dehydrocholesterol to 1alpha,25-dihydroxyvitamin D3 in an in vitro human skin equivalent model. J Invest Dermatol. 2001 Nov;117(5):1179-85. [PubMed:11710930 ]
Muzzin KB, Harper LF: Smith-Lemli-Opitz syndrome: a review, case report and dental implications. Spec Care Dentist. 2003;23(1):22-7. [PubMed:12887150 ]
Paterson CR, Moody JP, Pennington CR: Skin content of 7-dehydrocholesterol in patients with malabsorption. Nutrition. 1997 Sep;13(9):771-3. [PubMed:9290088 ]
Jira PE, Wevers RA, de Jong J, Rubio-Gozalbo E, Janssen-Zijlstra FS, van Heyst AF, Sengers RC, Smeitink JA: Simvastatin. A new therapeutic approach for Smith-Lemli-Opitz syndrome. J Lipid Res. 2000 Aug;41(8):1339-46. [PubMed:10946022 ]
Johnson DW, ten Brink HJ, Jakobs C: A rapid screening procedure for cholesterol and dehydrocholesterol by electrospray ionization tandem mass spectrometry. J Lipid Res. 2001 Oct;42(10):1699-705. [PubMed:11590227 ]
van Rooij A, Nijenhuis AA, Wijburg FA, Schutgens RB: Highly increased CSF concentrations of cholesterol precursors in Smith-Lemli-Opitz syndrome. J Inherit Metab Dis. 1997 Aug;20(4):578-80. [PubMed:9266395 ]
Andersson HC, Frentz J, Martinez JE, Tuck-Muller CM, Bellizaire J: Adrenal insufficiency in Smith-Lemli-Opitz syndrome. Am J Med Genet. 1999 Feb 19;82(5):382-4. [PubMed:10069708 ]
GarciaFuentes E, icioso Recio MV, del Castillo Acedo Del Olmo E, atas Jurado MM, Arana Aguera M, Lopez Lopez J: [Biochemical diagnosis of Smith-Lemli-Opitz syndrome in a patient with congenital adrenal hyperplasia]. An Esp Pediatr. 2000 Nov;53(5):482-7. [PubMed:11141372 ]
Jezela-Stanek A, Malunowicz EM, Ciara E, Popowska E, Goryluk-Kozakiewicz B, Spodar K, Czerwiecka M, Jezuita J, Nowaczyk MJ, Krajewska-Walasek M: Maternal urinary steroid profiles in prenatal diagnosis of Smith-Lemli-Opitz syndrome: first patient series comparing biochemical and molecular studies. Clin Genet. 2006 Jan;69(1):77-85. [PubMed:16451140 ]
Moody JP, Humphries CA, Allan SM, Paterson CR: Determination of 7-dehydrocholesterol in human skin by high-performance liquid chromatography. J Chromatogr. 1990 Aug 24;530(1):19-27. [PubMed:2277111 ]
Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
Dietschy JM, Turley SD: Thematic review series: brain Lipids. Cholesterol metabolism in the central nervous system during early development and in the mature animal. J Lipid Res. 2004 Aug;45(8):1375-97. [PubMed:15254070 ]
O'Byrne SM, Blaner WS: Retinol and retinyl esters: biochemistry and physiology. J Lipid Res. 2013 Jul;54(7):1731-43. doi: 10.1194/jlr.R037648. Epub 2013 Apr 26. [PubMed:23625372 ]
Norman AW: Sunlight, season, skin pigmentation, vitamin D, and 25-hydroxyvitamin D: integral components of the vitamin D endocrine system. Am J Clin Nutr. 1998 Jun;67(6):1108-10. doi: 10.1093/ajcn/67.6.1108. [PubMed:9625080 ]
Gomis DB, Fernandez MP, Gutierrez Alvarez MD: Simultaneous determination of fat-soluble vitamins and provitamins in milk by microcolumn liquid chromatography. J Chromatogr A. 2000 Sep 1;891(1):109-14. doi: 10.1016/s0021-9673(00)00623-3. [PubMed:10999630 ]
Adachi A, Kobayashi T: Identification of vitamin D3 and 7-dehydrocholesterol in cow's milk by gas chromatography-mass spectrometry and their quantitation by high-performance liquid chromatography. J Nutr Sci Vitaminol (Tokyo). 1979;25(2):67-78. doi: 10.3177/jnsv.25.67. [PubMed:225459 ]
Japelt RB, Jakobsen J: Vitamin D in plants: a review of occurrence, analysis, and biosynthesis. Front Plant Sci. 2013 May 13;4:136. doi: 10.3389/fpls.2013.00136. eCollection 2013. [PubMed:23717318 ]
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.
Linda T. Welson (2006). Triglycerides and Cholesterol Research. Nova Science Publishers Inc..

Enzymes

Enzyme Details

1. Hydroxymethylglutaryl-CoA synthase, mitochondrial

General function:: Involved in hydroxymethylglutaryl-CoA synthase activity
Specific function:: This enzyme condenses acetyl-CoA with acetoacetyl-CoA to form HMG-CoA, which is the substrate for HMG-CoA reductase.
Gene Name:: HMGCS2
Uniprot ID:: P54868
Molecular weight:: 52481.065

References

Honda M, Tint GS, Honda A, Nguyen LB, Chen TS, Shefer S: 7-Dehydrocholesterol down-regulates cholesterol biosynthesis in cultured Smith-Lemli-Opitz syndrome skin fibroblasts. J Lipid Res. 1998 Mar;39(3):647-57. [PubMed:9548596 ]

Enzyme Details

2. 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

References

Sugawara T, Fujimoto Y, Ishibashi T: Molecular cloning and structural analysis of human sterol C5 desaturase. Biochim Biophys Acta. 2001 Oct 31;1533(3):277-84. [PubMed:11731337 ]

Enzyme Details

3. Non-specific lipid-transfer protein

General function:: Involved in oxidoreductase activity
Specific function:: Mediates in vitro the transfer of all common phospholipids, cholesterol and gangliosides between membranes. May play a role in regulating steroidogenesis.
Gene Name:: SCP2
Uniprot ID:: P22307
Molecular weight:: 34974.505

References

Morin RJ, Brun MJ, Srikantaiah MV: Effect of age and cholestyramine feeding on rat liver 3-hydroxy-3-methyl glutaryl CoA reductase, sterol carrier protein 1 and sterol carrier protein 2 activities. Lipids. 1982 Jul;17(7):507-10. [PubMed:7121212 ]

Enzyme Details

4. 7-dehydrocholesterol reductase

General function:: Involved in 7-dehydrocholesterol reductase activity
Specific function:: Production of cholesterol by reduction of C7-C8 double bond of 7-dehydrocholesterol (7-DHC).
Gene Name:: DHCR7
Uniprot ID:: Q9UBM7
Molecular weight:: 54488.98

Reactions

Cholesterol + NADP → 7-Dehydrocholesterol + NADPH	details
Cholesterol + NAD → 7-Dehydrocholesterol + NADH + Hydrogen Ion	details
Cholesterol + NADP → 7-Dehydrocholesterol + NADPH + Hydrogen Ion	details

References

Porter FD: Smith-Lemli-Opitz syndrome: pathogenesis, diagnosis and management. Eur J Hum Genet. 2008 May;16(5):535-41. doi: 10.1038/ejhg.2008.10. Epub 2008 Feb 20. [PubMed:18285838 ]

Enzyme Details

5. Cholesterol side-chain cleavage enzyme, mitochondrial

General function:: Involved in monooxygenase activity
Specific function:: Catalyzes the side-chain cleavage reaction of cholesterol to pregnenolone.
Gene Name:: CYP11A1
Uniprot ID:: P05108
Molecular weight:: 60101.87

References

Guryev O, Carvalho RA, Usanov S, Gilep A, Estabrook RW: A pathway for the metabolism of vitamin D3: unique hydroxylated metabolites formed during catalysis with cytochrome P450scc (CYP11A1). Proc Natl Acad Sci U S A. 2003 Dec 9;100(25):14754-9. Epub 2003 Dec 1. [PubMed:14657394 ]

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

7-Dehydrodesmosterol + NADPH + Hydrogen Ion → 7-Dehydrocholesterol + NADP	details

Showing metabocard for 7-Dehydrocholesterol (HMDB0000032)

MOL for HMDB0000032 (7-Dehydrocholesterol)

3D MOL for HMDB0000032 (7-Dehydrocholesterol)

3D SDF for HMDB0000032 (7-Dehydrocholesterol)

3D-SDF for HMDB0000032 (7-Dehydrocholesterol)

PDB for HMDB0000032 (7-Dehydrocholesterol)

3D PDB for HMDB0000032 (7-Dehydrocholesterol)

SMILES for HMDB0000032 (7-Dehydrocholesterol)

INCHI for HMDB0000032 (7-Dehydrocholesterol)

Structure for HMDB0000032 (7-Dehydrocholesterol)

3D Structure for HMDB0000032 (7-Dehydrocholesterol)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes

References

Reactions

References

References

Reactions

References

References

Reactions