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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (3) Show 3 proteins XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2022-03-07 02:49:08 UTC

HMDB ID

HMDB0001188

Secondary Accession Numbers

HMDB0059621
HMDB01188
HMDB59621

Metabolite Identification

Common Name

(S)-2,3-Epoxysqualene

Description

(S)-2,3-Epoxysqualene, also known as 2,3-oxidosqualene or (S)-squalene-2,3-epoxide, belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. Thus, (S)-2,3-epoxysqualene is considered to be an isoprenoid lipid molecule. (S)-2,3-Epoxysqualene is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. (S)-2,3-Epoxysqualene is an intermediate in the biosynthesis of terpenoid. It is a substrate for squalene monooxygenase and lanosterol synthase.

Structure

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


  Mrv1652309042000192D          

 31 31  0  0  0  0            999 V2000
 9992.9586 9998.7576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9993.6732 9999.1697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9994.3882 9998.7576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.1028 9999.1697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.8175 9998.7576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.5342 9999.1697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.2491 9998.7576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.9638 9999.1697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.6784 9998.7576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.3941 9999.1697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.1076 9998.7576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.8231 9999.1697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.5365 9998.7576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.2520 9999.1697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.9675 9998.7576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.6809 9999.1697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.3964 9998.7576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10005.1120 9999.1697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10005.8254 9998.7576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10006.5409 9999.1697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10007.2543 9998.7576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10006.5409 9999.9944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.6809 9999.9944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.8231 9999.9944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.2491 9997.9323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9994.3882 9997.9323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9992.2439 9999.1697    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9991.4125 9999.1697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9991.8282 9999.8810    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9991.2548 9998.3604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9990.6423 9999.4665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
 27  1  1  1  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3 26  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7 25  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 12 24  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 16 23  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 28 30  1  0  0  0  0
 28 31  1  0  0  0  0
 28 29  1  0  0  0  0
 29 27  1  0  0  0  0
 27 28  1  0  0  0  0
M  END

HMDB0001188
     RDKit          3D
(S)-2,3-Epoxysqualene
 81 81  0  0  0  0  0  0  0  0999 V2000
    8.6777   -2.8143   -0.0533 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4597   -1.6216   -0.4603 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8201   -1.3964    0.0691 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9060   -0.7699   -1.3066 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5456   -0.9703   -1.8522 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6117    0.1273   -1.4982 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4282    0.2588   -0.0349 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5400    0.5946    0.8864 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1822    0.0805    0.4367 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9338    0.1968    1.8868 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9515    1.3302    2.0953 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6738    1.0265    1.3711 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9022   -0.1965    1.7284 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1914    1.8037    0.4161 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9223    1.4451   -0.2596 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0463    2.6063   -0.0074 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3545    2.3787   -0.6278 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4379    2.3371    0.1066 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4615    2.5067    1.5695 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7412    2.0993   -0.5983 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3365    0.8178   -0.0255 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6166    0.5891   -0.7215 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9065   -0.4804   -1.4436 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8759   -1.5412   -1.5740 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2195   -0.6273   -2.1083 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9675   -1.8534   -1.6316 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2285   -1.7974   -0.1408 C   0  0  2  0  0  0  0  0  0  0  0  0
   -8.9075   -2.8688    0.4070 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5528   -1.6115    0.4154 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6613   -0.8749    1.7264 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.8032   -1.5746   -0.4166 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7530   -2.5270    0.4489 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4939   -3.4041   -0.9963 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.3297   -3.4631    0.5622 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.7701   -0.6587    0.9000 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.4968   -1.0441   -0.7183 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.2436   -2.3276    0.4937 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.4967    0.1050   -1.6065 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5716   -1.1635   -2.9530 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1431   -1.9409   -1.4319 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6366    0.0457   -2.0247 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0455    1.1053   -1.8648 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2218    1.4009    1.6069 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4234    0.9720    0.3138 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8520   -0.2508    1.5130 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3789   -0.1483   -0.2728 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8037    0.3401    2.5149 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4261   -0.7628    2.2043 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7056    1.5115    3.1414 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3326    2.2795    1.6673 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4093   -0.7512    2.5453 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7840   -0.8925    0.8818 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8855    0.0473    2.0995 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7112    2.6959    0.1233 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5056    0.4911    0.0852 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0597    1.3410   -1.3675 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0908    2.7512    1.0877 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4711    3.5205   -0.4117 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4213    2.2449   -1.6974 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8711    3.4375    1.8001 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0944    1.6430    2.1369 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4906    2.7382    1.9076 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6062    1.9192   -1.6775 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4652    2.9016   -0.3677 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6405   -0.0320   -0.0984 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5626    0.9457    1.0574 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3790    1.3533   -0.6365 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1696   -2.2270   -2.3954 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8803   -1.1617   -1.8029 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9062   -2.1594   -0.6392 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7847    0.3018   -1.9855 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0362   -0.7680   -3.1962 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9638   -1.8253   -2.1253 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3802   -2.7365   -1.9301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3597   -1.4563    0.4465 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6498   -0.7661    2.1794 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.3456   -1.3935    2.4190 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.9970    0.1560    1.4888 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.6652   -1.8357    0.2469 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.0183   -0.5529   -0.8024 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.8015   -2.3249   -1.2237 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 23 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 29 31  1  0
 29 27  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
  3 35  1  0
  3 36  1  0
  3 37  1  0
  4 38  1  0
  5 39  1  0
  5 40  1  0
  6 41  1  0
  6 42  1  0
  8 43  1  0
  8 44  1  0
  8 45  1  0
  9 46  1  0
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 19 60  1  0
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 21 66  1  0
 22 67  1  0
 24 68  1  0
 24 69  1  0
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 25 71  1  0
 25 72  1  0
 26 73  1  0
 26 74  1  0
 27 75  1  1
 30 76  1  0
 30 77  1  0
 30 78  1  0
 31 79  1  0
 31 80  1  0
 31 81  1  0
M  END


  Mrv1652309042000192D          

 31 31  0  0  0  0            999 V2000
 9992.9586 9998.7576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9993.6732 9999.1697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9994.3882 9998.7576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.1028 9999.1697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.8175 9998.7576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.5342 9999.1697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.2491 9998.7576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.9638 9999.1697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.6784 9998.7576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.3941 9999.1697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.1076 9998.7576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.8231 9999.1697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.5365 9998.7576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.2520 9999.1697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.9675 9998.7576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.6809 9999.1697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.3964 9998.7576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10005.1120 9999.1697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10005.8254 9998.7576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10006.5409 9999.1697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10007.2543 9998.7576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10006.5409 9999.9944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.6809 9999.9944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.8231 9999.9944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.2491 9997.9323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9994.3882 9997.9323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9992.2439 9999.1697    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9991.4125 9999.1697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9991.8282 9999.8810    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9991.2548 9998.3604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9990.6423 9999.4665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
 27  1  1  1  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3 26  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7 25  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 12 24  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 16 23  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 28 30  1  0  0  0  0
 28 31  1  0  0  0  0
 28 29  1  0  0  0  0
 29 27  1  0  0  0  0
 27 28  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0001188

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(C)=CCC\C(C)=C\CC\C(C)=C\CC\C=C(/C)CC\C=C(/C)CC[C@@H]1OC1(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C30H50O/c1-24(2)14-11-17-27(5)20-12-18-25(3)15-9-10-16-26(4)19-13-21-28(6)22-23-29-30(7,8)31-29/h14-16,20-21,29H,9-13,17-19,22-23H2,1-8H3/b25-15+,26-16+,27-20+,28-21+/t29-/m0/s1

> <INCHI_KEY>
QYIMSPSDBYKPPY-RSKUXYSASA-N

> <FORMULA>
C30H50O

> <MOLECULAR_WEIGHT>
426.7174

> <EXACT_MASS>
426.386166222

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
81

> <JCHEM_AVERAGE_POLARIZABILITY>
57.01860427813887

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3S)-2,2-dimethyl-3-[(3E,7E,11E,15E)-3,7,12,16,20-pentamethylhenicosa-3,7,11,15,19-pentaen-1-yl]oxirane

> <ALOGPS_LOGP>
8.58

> <JCHEM_LOGP>
9.443276314333334

> <ALOGPS_LOGS>
-6.01

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.2224203123390325

> <JCHEM_POLAR_SURFACE_AREA>
12.53

> <JCHEM_REFRACTIVITY>
143.45530000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
15

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.16e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
squalene 2,3-oxide

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0001188
     RDKit          3D
(S)-2,3-Epoxysqualene
 81 81  0  0  0  0  0  0  0  0999 V2000
    8.6777   -2.8143   -0.0533 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4597   -1.6216   -0.4603 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8201   -1.3964    0.0691 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9060   -0.7699   -1.3066 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5456   -0.9703   -1.8522 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6117    0.1273   -1.4982 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4282    0.2588   -0.0349 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5400    0.5946    0.8864 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1822    0.0805    0.4367 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9338    0.1968    1.8868 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9515    1.3302    2.0953 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6738    1.0265    1.3711 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9022   -0.1965    1.7284 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1914    1.8037    0.4161 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9223    1.4451   -0.2596 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0463    2.6063   -0.0074 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3545    2.3787   -0.6278 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4379    2.3371    0.1066 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4615    2.5067    1.5695 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7412    2.0993   -0.5983 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3365    0.8178   -0.0255 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6166    0.5891   -0.7215 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9065   -0.4804   -1.4436 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8759   -1.5412   -1.5740 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2195   -0.6273   -2.1083 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9675   -1.8534   -1.6316 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2285   -1.7974   -0.1408 C   0  0  2  0  0  0  0  0  0  0  0  0
   -8.9075   -2.8688    0.4070 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5528   -1.6115    0.4154 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6613   -0.8749    1.7264 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.8032   -1.5746   -0.4166 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7530   -2.5270    0.4489 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4939   -3.4041   -0.9963 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.3297   -3.4631    0.5622 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.7701   -0.6587    0.9000 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.4968   -1.0441   -0.7183 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.2436   -2.3276    0.4937 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.4967    0.1050   -1.6065 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5716   -1.1635   -2.9530 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1431   -1.9409   -1.4319 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6366    0.0457   -2.0247 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0455    1.1053   -1.8648 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2218    1.4009    1.6069 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4234    0.9720    0.3138 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8520   -0.2508    1.5130 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3789   -0.1483   -0.2728 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8037    0.3401    2.5149 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4261   -0.7628    2.2043 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7056    1.5115    3.1414 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3326    2.2795    1.6673 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4093   -0.7512    2.5453 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7840   -0.8925    0.8818 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8855    0.0473    2.0995 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7112    2.6959    0.1233 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5056    0.4911    0.0852 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0597    1.3410   -1.3675 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0908    2.7512    1.0877 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4711    3.5205   -0.4117 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4213    2.2449   -1.6974 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8711    3.4375    1.8001 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0944    1.6430    2.1369 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4906    2.7382    1.9076 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6062    1.9192   -1.6775 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4652    2.9016   -0.3677 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6405   -0.0320   -0.0984 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5626    0.9457    1.0574 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3790    1.3533   -0.6365 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1696   -2.2270   -2.3954 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8803   -1.1617   -1.8029 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9062   -2.1594   -0.6392 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7847    0.3018   -1.9855 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0362   -0.7680   -3.1962 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9638   -1.8253   -2.1253 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3802   -2.7365   -1.9301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3597   -1.4563    0.4465 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6498   -0.7661    2.1794 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.3456   -1.3935    2.4190 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.9970    0.1560    1.4888 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.6652   -1.8357    0.2469 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.0183   -0.5529   -0.8024 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.8015   -2.3249   -1.2237 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 23 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 29 31  1  0
 29 27  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
  3 35  1  0
  3 36  1  0
  3 37  1  0
  4 38  1  0
  5 39  1  0
  5 40  1  0
  6 41  1  0
  6 42  1  0
  8 43  1  0
  8 44  1  0
  8 45  1  0
  9 46  1  0
 10 47  1  0
 10 48  1  0
 11 49  1  0
 11 50  1  0
 13 51  1  0
 13 52  1  0
 13 53  1  0
 14 54  1  0
 15 55  1  0
 15 56  1  0
 16 57  1  0
 16 58  1  0
 17 59  1  0
 19 60  1  0
 19 61  1  0
 19 62  1  0
 20 63  1  0
 20 64  1  0
 21 65  1  0
 21 66  1  0
 22 67  1  0
 24 68  1  0
 24 69  1  0
 24 70  1  0
 25 71  1  0
 25 72  1  0
 26 73  1  0
 26 74  1  0
 27 75  1  1
 30 76  1  0
 30 77  1  0
 30 78  1  0
 31 79  1  0
 31 80  1  0
 31 81  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    8653.5238664.348   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8654.8578665.117   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8656.1918664.348   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    8657.5258665.117   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0    8658.8598664.348   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    8660.1978665.117   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    8661.5328664.348   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8662.8668665.117   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8664.2008664.348   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8665.5368665.117   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8666.8688664.348   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8668.2038665.117   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8669.5358664.348   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8670.8708665.117   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8672.2068664.348   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8673.5388665.117   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8674.8738664.348   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    8676.2098665.117   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0    8677.5418664.348   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0    8678.8768665.117   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0    8680.2088664.348   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0    8678.8768666.656   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0    8673.5388666.656   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0    8668.2038666.656   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0    8661.5328662.807   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0    8656.1918662.807   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0    8652.1898665.117   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0    8650.6378665.117   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0    8651.4138666.445   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0    8650.3428663.606   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0    8649.1998665.671   0.000  0.00  0.00           C+0
CONECT    1    2   27                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4   26                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   25                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   24                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   23                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20                                                            
CONECT   23   16                                                            
CONECT   24   12                                                            
CONECT   25    7                                                            
CONECT   26    3                                                            
CONECT   27    1   29   28                                                  
CONECT   28   30   31   29   27                                             
CONECT   29   28   27                                                       
CONECT   30   28                                                            
CONECT   31   28                                                            
MASTER        0    0    0    0    0    0    0    0   31    0   62    0
END

COMPND    HMDB0001188
HETATM    1  C1  UNL     1       8.678  -2.814  -0.053  1.00  0.00           C  
HETATM    2  C2  UNL     1       9.460  -1.622  -0.460  1.00  0.00           C  
HETATM    3  C3  UNL     1      10.820  -1.396   0.069  1.00  0.00           C  
HETATM    4  C4  UNL     1       8.906  -0.770  -1.307  1.00  0.00           C  
HETATM    5  C5  UNL     1       7.546  -0.970  -1.852  1.00  0.00           C  
HETATM    6  C6  UNL     1       6.612   0.127  -1.498  1.00  0.00           C  
HETATM    7  C7  UNL     1       6.428   0.259  -0.035  1.00  0.00           C  
HETATM    8  C8  UNL     1       7.540   0.595   0.886  1.00  0.00           C  
HETATM    9  C9  UNL     1       5.182   0.080   0.437  1.00  0.00           C  
HETATM   10  C10 UNL     1       4.934   0.197   1.887  1.00  0.00           C  
HETATM   11  C11 UNL     1       3.952   1.330   2.095  1.00  0.00           C  
HETATM   12  C12 UNL     1       2.674   1.026   1.371  1.00  0.00           C  
HETATM   13  C13 UNL     1       1.902  -0.196   1.728  1.00  0.00           C  
HETATM   14  C14 UNL     1       2.191   1.804   0.416  1.00  0.00           C  
HETATM   15  C15 UNL     1       0.922   1.445  -0.260  1.00  0.00           C  
HETATM   16  C16 UNL     1      -0.046   2.606  -0.007  1.00  0.00           C  
HETATM   17  C17 UNL     1      -1.355   2.379  -0.628  1.00  0.00           C  
HETATM   18  C18 UNL     1      -2.438   2.337   0.107  1.00  0.00           C  
HETATM   19  C19 UNL     1      -2.461   2.507   1.569  1.00  0.00           C  
HETATM   20  C20 UNL     1      -3.741   2.099  -0.598  1.00  0.00           C  
HETATM   21  C21 UNL     1      -4.337   0.818  -0.026  1.00  0.00           C  
HETATM   22  C22 UNL     1      -5.617   0.589  -0.722  1.00  0.00           C  
HETATM   23  C23 UNL     1      -5.907  -0.480  -1.444  1.00  0.00           C  
HETATM   24  C24 UNL     1      -4.876  -1.541  -1.574  1.00  0.00           C  
HETATM   25  C25 UNL     1      -7.220  -0.627  -2.108  1.00  0.00           C  
HETATM   26  C26 UNL     1      -7.967  -1.853  -1.632  1.00  0.00           C  
HETATM   27  C27 UNL     1      -8.229  -1.797  -0.141  1.00  0.00           C  
HETATM   28  O1  UNL     1      -8.908  -2.869   0.407  1.00  0.00           O  
HETATM   29  C28 UNL     1      -9.553  -1.611   0.415  1.00  0.00           C  
HETATM   30  C29 UNL     1      -9.661  -0.875   1.726  1.00  0.00           C  
HETATM   31  C30 UNL     1     -10.803  -1.575  -0.417  1.00  0.00           C  
HETATM   32  H1  UNL     1       7.753  -2.527   0.449  1.00  0.00           H  
HETATM   33  H2  UNL     1       8.494  -3.404  -0.996  1.00  0.00           H  
HETATM   34  H3  UNL     1       9.330  -3.463   0.562  1.00  0.00           H  
HETATM   35  H4  UNL     1      10.770  -0.659   0.900  1.00  0.00           H  
HETATM   36  H5  UNL     1      11.497  -1.044  -0.718  1.00  0.00           H  
HETATM   37  H6  UNL     1      11.244  -2.328   0.494  1.00  0.00           H  
HETATM   38  H7  UNL     1       9.497   0.105  -1.606  1.00  0.00           H  
HETATM   39  H8  UNL     1       7.572  -1.163  -2.953  1.00  0.00           H  
HETATM   40  H9  UNL     1       7.143  -1.941  -1.432  1.00  0.00           H  
HETATM   41  H10 UNL     1       5.637   0.046  -2.025  1.00  0.00           H  
HETATM   42  H11 UNL     1       7.045   1.105  -1.865  1.00  0.00           H  
HETATM   43  H12 UNL     1       7.222   1.401   1.607  1.00  0.00           H  
HETATM   44  H13 UNL     1       8.423   0.972   0.314  1.00  0.00           H  
HETATM   45  H14 UNL     1       7.852  -0.251   1.513  1.00  0.00           H  
HETATM   46  H15 UNL     1       4.379  -0.148  -0.273  1.00  0.00           H  
HETATM   47  H16 UNL     1       5.804   0.340   2.515  1.00  0.00           H  
HETATM   48  H17 UNL     1       4.426  -0.763   2.204  1.00  0.00           H  
HETATM   49  H18 UNL     1       3.706   1.512   3.141  1.00  0.00           H  
HETATM   50  H19 UNL     1       4.333   2.279   1.667  1.00  0.00           H  
HETATM   51  H20 UNL     1       2.409  -0.751   2.545  1.00  0.00           H  
HETATM   52  H21 UNL     1       1.784  -0.893   0.882  1.00  0.00           H  
HETATM   53  H22 UNL     1       0.885   0.047   2.100  1.00  0.00           H  
HETATM   54  H23 UNL     1       2.711   2.696   0.123  1.00  0.00           H  
HETATM   55  H24 UNL     1       0.506   0.491   0.085  1.00  0.00           H  
HETATM   56  H25 UNL     1       1.060   1.341  -1.368  1.00  0.00           H  
HETATM   57  H26 UNL     1      -0.091   2.751   1.088  1.00  0.00           H  
HETATM   58  H27 UNL     1       0.471   3.521  -0.412  1.00  0.00           H  
HETATM   59  H28 UNL     1      -1.421   2.245  -1.697  1.00  0.00           H  
HETATM   60  H29 UNL     1      -1.871   3.438   1.800  1.00  0.00           H  
HETATM   61  H30 UNL     1      -2.094   1.643   2.137  1.00  0.00           H  
HETATM   62  H31 UNL     1      -3.491   2.738   1.908  1.00  0.00           H  
HETATM   63  H32 UNL     1      -3.606   1.919  -1.677  1.00  0.00           H  
HETATM   64  H33 UNL     1      -4.465   2.902  -0.368  1.00  0.00           H  
HETATM   65  H34 UNL     1      -3.640  -0.032  -0.098  1.00  0.00           H  
HETATM   66  H35 UNL     1      -4.563   0.946   1.057  1.00  0.00           H  
HETATM   67  H36 UNL     1      -6.379   1.353  -0.637  1.00  0.00           H  
HETATM   68  H37 UNL     1      -5.170  -2.227  -2.395  1.00  0.00           H  
HETATM   69  H38 UNL     1      -3.880  -1.162  -1.803  1.00  0.00           H  
HETATM   70  H39 UNL     1      -4.906  -2.159  -0.639  1.00  0.00           H  
HETATM   71  H40 UNL     1      -7.785   0.302  -1.986  1.00  0.00           H  
HETATM   72  H41 UNL     1      -7.036  -0.768  -3.196  1.00  0.00           H  
HETATM   73  H42 UNL     1      -8.964  -1.825  -2.125  1.00  0.00           H  
HETATM   74  H43 UNL     1      -7.380  -2.737  -1.930  1.00  0.00           H  
HETATM   75  H44 UNL     1      -7.360  -1.456   0.446  1.00  0.00           H  
HETATM   76  H45 UNL     1      -8.650  -0.766   2.179  1.00  0.00           H  
HETATM   77  H46 UNL     1     -10.346  -1.394   2.419  1.00  0.00           H  
HETATM   78  H47 UNL     1      -9.997   0.156   1.489  1.00  0.00           H  
HETATM   79  H48 UNL     1     -11.665  -1.836   0.247  1.00  0.00           H  
HETATM   80  H49 UNL     1     -11.018  -0.553  -0.802  1.00  0.00           H  
HETATM   81  H50 UNL     1     -10.802  -2.325  -1.224  1.00  0.00           H  
CONECT    1    2   32   33   34
CONECT    2    3    4    4
CONECT    3   35   36   37
CONECT    4    5   38
CONECT    5    6   39   40
CONECT    6    7   41   42
CONECT    7    8    9    9
CONECT    8   43   44   45
CONECT    9   10   46
CONECT   10   11   47   48
CONECT   11   12   49   50
CONECT   12   13   14   14
CONECT   13   51   52   53
CONECT   14   15   54
CONECT   15   16   55   56
CONECT   16   17   57   58
CONECT   17   18   18   59
CONECT   18   19   20
CONECT   19   60   61   62
CONECT   20   21   63   64
CONECT   21   22   65   66
CONECT   22   23   23   67
CONECT   23   24   25
CONECT   24   68   69   70
CONECT   25   26   71   72
CONECT   26   27   73   74
CONECT   27   28   29   75
CONECT   28   29
CONECT   29   30   31
CONECT   30   76   77   78
CONECT   31   79   80   81
END

HMDB0001188
     RDKit          3D
(S)-2,3-Epoxysqualene
 81 81  0  0  0  0  0  0  0  0999 V2000
    8.6777   -2.8143   -0.0533 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4597   -1.6216   -0.4603 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8201   -1.3964    0.0691 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9060   -0.7699   -1.3066 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5456   -0.9703   -1.8522 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6117    0.1273   -1.4982 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4282    0.2588   -0.0349 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5400    0.5946    0.8864 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1822    0.0805    0.4367 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9338    0.1968    1.8868 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9515    1.3302    2.0953 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6738    1.0265    1.3711 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9022   -0.1965    1.7284 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1914    1.8037    0.4161 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9223    1.4451   -0.2596 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0463    2.6063   -0.0074 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3545    2.3787   -0.6278 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4379    2.3371    0.1066 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4615    2.5067    1.5695 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7412    2.0993   -0.5983 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3365    0.8178   -0.0255 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6166    0.5891   -0.7215 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9065   -0.4804   -1.4436 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8759   -1.5412   -1.5740 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2195   -0.6273   -2.1083 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9675   -1.8534   -1.6316 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2285   -1.7974   -0.1408 C   0  0  2  0  0  0  0  0  0  0  0  0
   -8.9075   -2.8688    0.4070 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5528   -1.6115    0.4154 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6613   -0.8749    1.7264 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.8032   -1.5746   -0.4166 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7530   -2.5270    0.4489 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4939   -3.4041   -0.9963 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.3297   -3.4631    0.5622 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.7701   -0.6587    0.9000 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.4968   -1.0441   -0.7183 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.2436   -2.3276    0.4937 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.4967    0.1050   -1.6065 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5716   -1.1635   -2.9530 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1431   -1.9409   -1.4319 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6366    0.0457   -2.0247 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0455    1.1053   -1.8648 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2218    1.4009    1.6069 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4234    0.9720    0.3138 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8520   -0.2508    1.5130 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3789   -0.1483   -0.2728 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8037    0.3401    2.5149 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4261   -0.7628    2.2043 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7056    1.5115    3.1414 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3326    2.2795    1.6673 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4093   -0.7512    2.5453 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7840   -0.8925    0.8818 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8855    0.0473    2.0995 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7112    2.6959    0.1233 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5056    0.4911    0.0852 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0597    1.3410   -1.3675 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0908    2.7512    1.0877 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4711    3.5205   -0.4117 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4213    2.2449   -1.6974 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8711    3.4375    1.8001 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0944    1.6430    2.1369 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4906    2.7382    1.9076 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6062    1.9192   -1.6775 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4652    2.9016   -0.3677 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6405   -0.0320   -0.0984 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5626    0.9457    1.0574 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3790    1.3533   -0.6365 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1696   -2.2270   -2.3954 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8803   -1.1617   -1.8029 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9062   -2.1594   -0.6392 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7847    0.3018   -1.9855 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0362   -0.7680   -3.1962 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9638   -1.8253   -2.1253 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3802   -2.7365   -1.9301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3597   -1.4563    0.4465 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6498   -0.7661    2.1794 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.3456   -1.3935    2.4190 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.9970    0.1560    1.4888 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.6652   -1.8357    0.2469 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.0183   -0.5529   -0.8024 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.8015   -2.3249   -1.2237 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 23 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 29 31  1  0
 29 27  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
  3 35  1  0
  3 36  1  0
  3 37  1  0
  4 38  1  0
  5 39  1  0
  5 40  1  0
  6 41  1  0
  6 42  1  0
  8 43  1  0
  8 44  1  0
  8 45  1  0
  9 46  1  0
 10 47  1  0
 10 48  1  0
 11 49  1  0
 11 50  1  0
 13 51  1  0
 13 52  1  0
 13 53  1  0
 14 54  1  0
 15 55  1  0
 15 56  1  0
 16 57  1  0
 16 58  1  0
 17 59  1  0
 19 60  1  0
 19 61  1  0
 19 62  1  0
 20 63  1  0
 20 64  1  0
 21 65  1  0
 21 66  1  0
 22 67  1  0
 24 68  1  0
 24 69  1  0
 24 70  1  0
 25 71  1  0
 25 72  1  0
 26 73  1  0
 26 74  1  0
 27 75  1  1
 30 76  1  0
 30 77  1  0
 30 78  1  0
 31 79  1  0
 31 80  1  0
 31 81  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(3S)-2,3-Dihydro-2,3-epoxysqualene	ChEBI
(3S)-2,3-Epoxy-2,3-dihydrosqualene	ChEBI
(S)-2,3-Dihydro-2,3-epoxysqualene	ChEBI
(S)-2,3-Epoxy-2,3-dihydrosqualene	ChEBI
(S)-2,3-Oxidosqualene	ChEBI
(S)-Squalene-2,3-epoxide	ChEBI
2,3-EDSQ	ChEBI
2,3-Epoxisqualene	ChEBI
2,3-Oxidosqualene	ChEBI
Oxidosqualene	ChEBI
Squalene 2,3-epoxide	ChEBI
Squalene 2,3-oxide	ChEBI
2,3-Epoxy-2,3-dihydrosqualene	HMDB
2,3-Oxidosqualene, (R)-isomer	HMDB
2,3-Oxidosqualene, (R-(all-e))-isomer	HMDB
2,3-Oxidosqualene, (all-e)-(+-)-isomer	HMDB
Squalene monohydroperoxide	HMDB
Squalene-2,3-epoxide	HMDB
(3S)-Oxidosqualene	HMDB
2,3-Oxidosqualene, (S-(all-e))-isomer	HMDB
Squalene-2,3-oxide	HMDB
2,3-Oxidosqualene, (S)-isomer	HMDB
Squslene oxide	HMDB
Squalene peroxide	HMDB
(3S)-2,3-Epoxysqualene	HMDB
(3S)-2,3-Oxidosqualene	HMDB
(3S)-Squalene-2,3-epoxide	HMDB
(S)-Squalene 2,3-epoxide	HMDB
2,3(S)-Oxidosqualene	HMDB
3(S)-Oxidosqualene	HMDB
Squalene 2,3(S)-oxide	HMDB
(3R,S)-Oxidosqualene	HMDB
(R,S)-Squalene 2,3-epoxide	HMDB
(RS)-2,3-Epoxy-2,3-dihydrosqualene	HMDB
(±)-2,3-epoxysqualene	HMDB
(±)-squalene oxide	HMDB
2,3-Epoxysqualene	HMDB
Squalene epoxide	HMDB
Squalene oxide	HMDB
(3S)-2,2-Dimethyl-3-[(3E,7E,11E,15E)-3,7,12,16,20-pentamethyl-3,7,11,15,19-heneicosapentaen-1-yl]oxirane	HMDB
(S)-2,3-Epoxysqualene	HMDB

Chemical Formula

C₃₀H₅₀O

Average Molecular Weight

426.7174

Monoisotopic Molecular Weight

426.386166222

IUPAC Name

(3S)-2,2-dimethyl-3-[(3E,7E,11E,15E)-3,7,12,16,20-pentamethylhenicosa-3,7,11,15,19-pentaen-1-yl]oxirane

Traditional Name

squalene 2,3-oxide

CAS Registry Number

54910-48-4

SMILES

CC(C)=CCC\C(C)=C\CC\C(C)=C\CC\C=C(/C)CC\C=C(/C)CC[C@@H]1OC1(C)C

InChI Identifier

InChI=1S/C30H50O/c1-24(2)14-11-17-27(5)20-12-18-25(3)15-9-10-16-26(4)19-13-21-28(6)22-23-29-30(7,8)31-29/h14-16,20-21,29H,9-13,17-19,22-23H2,1-8H3/b25-15+,26-16+,27-20+,28-21+/t29-/m0/s1

InChI Key

QYIMSPSDBYKPPY-RSKUXYSASA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Triterpenoids

Direct Parent

Triterpenoids

Alternative Parents

Substituents

Triterpenoid
Oxacycle
Organoheterocyclic compound
Ether
Oxirane
Dialkyl ether
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

2,3-epoxysqualene (CHEBI:15441 )
Acyclic triterpenoids (C01054 )
Liner triterpenes (C01054 )
Acyclic triterpenoids (LMPR0106010010 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Organelle

Endoplasmic reticulum (HMDB: HMDB0001188)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0001188)

Source

Endogenous

Endogenous (HMDB: HMDB0001188)

Plant

Animal

Animal (HMDB: HMDB0001188)

Exogenous

Food

Food (HMDB: HMDB0001188)

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: HMDB0001188)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0001188)

Biochemical pathway

Drug action pathway

Alendronate Action Pathway (HMDB: HMDB0001188)
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: HMDB0001188)
Steroid Biosynthesis (PathBank: SMP0087326)
Steroid Biosynthesis (PathBank: SMP0002381)
Cholesterol Biosynthesis and Metabolism CE(14:0) (PathBank: SMP0002435)
Cholesterol Biosynthesis and Metabolism CE(10:0) (PathBank: SMP0002436)
Cholesterol Biosynthesis and Metabolism CE(12:0) (PathBank: SMP0002438)
Cholesterol Biosynthesis and Metabolism CE(16:0) (PathBank: SMP0002440)
Cholesterol Biosynthesis and Metabolism CE(18:0) (PathBank: SMP0002441)
Epoxysqualene Biosynthesis (PathBank: SMP0012042)
Cholesterol Biosynthesis and Metabolism (PathBank: SMP0070041)
Mevalonate Pathway (PathBank: SMP0121055)
Sesquiterpenoid Biosynthesis (PathBank: SMP0121205)
Triterpenoid Biosynthesis (PathBank: SMP0121207)

Disease pathway

Smith-Lemli-Opitz Syndrome (SLOS) (PathBank: SMP0120515)
Desmosterolosis (PathBank: SMP0120692)
Mevalonic Aciduria (PathBank: SMP0120794)
Chondrodysplasia Punctata II, X-Linked Dominant (CDPX2) (HMDB: HMDB0001188)
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: HMDB0001188)

Cellular process

Cell signaling (HMDB: HMDB0001188)

Biochemical process

Lipid transport (HMDB: HMDB0001188)

Role

Biological role

Energy source (HMDB: HMDB0001188)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0001188)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.00042 g/L	ALOGPS
logP	8.58	ALOGPS
logP	9.44	ChemAxon
logS	-6	ALOGPS
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	12.53 Å²	ChemAxon
Rotatable Bond Count	15	ChemAxon
Refractivity	143.46 m³·mol⁻¹	ChemAxon
Polarizability	57.02 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	205.828	31661259
DarkChem	[M-H]-	200.435	31661259
AllCCS	[M+H]+	222.262	32859911
AllCCS	[M-H]-	208.063	32859911
DeepCCS	[M+H]+	221.307	30932474
DeepCCS	[M-H]-	218.949	30932474
DeepCCS	[M-2H]-	251.836	30932474
DeepCCS	[M+Na]+	227.401	30932474
AllCCS	[M+H]+	222.3	32859911
AllCCS	[M+H-H2O]+	220.2	32859911
AllCCS	[M+NH4]+	224.1	32859911
AllCCS	[M+Na]+	224.7	32859911
AllCCS	[M-H]-	208.1	32859911
AllCCS	[M+Na-2H]-	210.7	32859911
AllCCS	[M+HCOO]-	213.7	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022.	9.39 minutes	32390414
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022.	9.62 minutes	32390414
Predicted by Siyang on May 30, 2022	31.2686 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.58 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	41.6 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
(S)-2,3-Epoxysqualene	CC(C)=CCC\C(C)=C\CC\C(C)=C\CC\C=C(/C)CC\C=C(/C)CC[C@@H]1OC1(C)C	3057.7	Standard polar	33892256
(S)-2,3-Epoxysqualene	CC(C)=CCC\C(C)=C\CC\C(C)=C\CC\C=C(/C)CC\C=C(/C)CC[C@@H]1OC1(C)C	2838.1	Standard non polar	33892256
(S)-2,3-Epoxysqualene	CC(C)=CCC\C(C)=C\CC\C(C)=C\CC\C=C(/C)CC\C=C(/C)CC[C@@H]1OC1(C)C	2987.6	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 - (S)-2,3-Epoxysqualene GC-MS (Non-derivatized) - 70eV, Positive	splash10-01rf-3696400000-dd04dae2363e5ff874a8	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (S)-2,3-Epoxysqualene 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 - (S)-2,3-Epoxysqualene 10V, Positive-QTOF	splash10-004i-0424900000-7fc557d70c5c9e3da792	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-2,3-Epoxysqualene 20V, Positive-QTOF	splash10-014i-4859200000-154cc236135feb13b7fe	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-2,3-Epoxysqualene 40V, Positive-QTOF	splash10-0gb9-7493000000-f50f29f61b0b15da33f7	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-2,3-Epoxysqualene 10V, Negative-QTOF	splash10-004i-0000900000-51b63741b5f02135d106	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-2,3-Epoxysqualene 20V, Negative-QTOF	splash10-004i-2000900000-5a6929cb0f28227226e9	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-2,3-Epoxysqualene 40V, Negative-QTOF	splash10-0a4i-9105300000-2fc6b31bfdb56acb80f9	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-2,3-Epoxysqualene 10V, Negative-QTOF	splash10-004i-0000900000-590c9e4adfdd12b64d93	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-2,3-Epoxysqualene 20V, Negative-QTOF	splash10-004i-1101900000-db9a88388cd111945a57	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-2,3-Epoxysqualene 40V, Negative-QTOF	splash10-052u-2339100000-6f4e24f11b72c0cb1c24	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-2,3-Epoxysqualene 10V, Positive-QTOF	splash10-05rr-4545900000-9f67cba78f15989d34a8	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-2,3-Epoxysqualene 20V, Positive-QTOF	splash10-066r-5609300000-19d2e2da63dd111fdd58	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-2,3-Epoxysqualene 40V, Positive-QTOF	splash10-053u-9603000000-d795105f1da47d79c7dd	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane (predicted from logP)
Endoplasmic reticulum

Biospecimen Locations

Not Available

Tissue Locations

Not Available

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

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

2,3-Oxidosqualene

METLIN ID

Not Available

PubChem Compound

5459811

PDB ID

Not Available

ChEBI ID

15441

Food Biomarker Ontology

Not Available

VMH ID

SSQ23EPX

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

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 ]
Kimura M, Kushiro T, Shibuya M, Ebizuka Y, Abe I: Protostadienol synthase from Aspergillus fumigatus: functional conversion into lanosterol synthase. Biochem Biophys Res Commun. 2010 Jan 1;391(1):899-902. doi: 10.1016/j.bbrc.2009.11.160. Epub 2009 Nov 29. [PubMed:19951700 ]
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Enzymes

Enzyme Details

1. Squalene monooxygenase

General function:: Involved in oxidoreductase activity
Specific function:: Catalyzes the first oxygenation step in sterol biosynthesis and is suggested to be one of the rate-limiting enzymes in this pathway.
Gene Name:: SQLE
Uniprot ID:: Q14534
Molecular weight:: 63922.505

Reactions

Squalene + Reduced acceptor + Oxygen → (S)-2,3-Epoxysqualene + Acceptor + Water	details
Squalene + Oxygen + NADPH + Hydrogen Ion → (S)-2,3-Epoxysqualene + NADP + Water	details

Enzyme Details

2. Lanosterol synthase

General function:: Involved in catalytic activity
Specific function:: Catalyzes the cyclization of (S)-2,3 oxidosqualene to lanosterol, a reaction that forms the sterol nucleus.
Gene Name:: LSS
Uniprot ID:: P48449
Molecular weight:: 83308.065

Reactions

(S)-2,3-Epoxysqualene → Lanosterol	details

Enzyme Details

3. Putative uncharacterized protein DKFZp686B0215

General function:: Involved in oxidoreductase activity
Specific function:: Not Available
Gene Name:: DKFZp686B0215
Uniprot ID:: Q5HYI4
Molecular weight:: 63793.4

Showing metabocard for (S)-2,3-Epoxysqualene (HMDB0001188)

MOL for HMDB0001188 ((S)-2,3-Epoxysqualene)

3D MOL for HMDB0001188 ((S)-2,3-Epoxysqualene)

3D SDF for HMDB0001188 ((S)-2,3-Epoxysqualene)

3D-SDF for HMDB0001188 ((S)-2,3-Epoxysqualene)

PDB for HMDB0001188 ((S)-2,3-Epoxysqualene)

3D PDB for HMDB0001188 ((S)-2,3-Epoxysqualene)

SMILES for HMDB0001188 ((S)-2,3-Epoxysqualene)

INCHI for HMDB0001188 ((S)-2,3-Epoxysqualene)

Structure for HMDB0001188 ((S)-2,3-Epoxysqualene)

3D Structure for HMDB0001188 ((S)-2,3-Epoxysqualene)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

Reactions

Reactions