NP-MRD: Showing NP-Card for epicholestrol (NP0141985)

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Record Information

Version

2.0

Created at

2022-09-01 20:25:17 UTC

Updated at

2022-09-01 20:25:17 UTC

NP-MRD ID

NP0141985

Secondary Accession Numbers

None

Natural Product Identification

Common Name

epicholestrol

Description

Cholesterol belongs to the class of organic compounds known as cholesterols and derivatives. Cholesterols and derivatives are compounds containing a 3-hydroxylated cholestane core. Cholesterol is an extremely weak basic (essentially neutral) compound (based on its pKa). It is an essential component of mammalian cell membranes where it is required to establish proper membrane permeability and fluidity. Within humans, cholesterol participates in a number of enzymatic reactions. In particular, cholesterol can be converted into 7a-hydroxycholesterol through the action of the enzyme cholesterol 7-alpha-monooxygenase. In addition, cholesterol and palmitic acid can be biosynthesized from ce(22:2(13Z,16Z)) through the action of the enzyme lysosomal acid lipase/cholesteryl ester hydrolase. ; Mevalonate is then converted to 3-isopentenyl pyrophosphate in three reactions which require ATP. They carry mostly triglyceride fats and cholesterol (that are from food and especially internal cholesterol secreted by the liver into the bile). In humans, cholesterol is involved in the metabolic disorder called familial hypercholanemia (fhca). Outside of the human body, Cholesterol is found, on average, in the highest concentration within a few different foods, such as sturgeons, eggs, and other fish products and in a lower concentration in liquors, stews, and pot pies. Cholesterol has also been detected, but not quantified in, several different foods, such as horchata, focaccia, sourdoughs, rums, and pecan nuts. This could make cholesterol a potential biomarker for the consumption of these foods. epicholestrol is found in Acanthaster planci, Achillea millefolium, Aframomum sceptrum, Ajuga reptans, Amaranthus caudatus, Amphilectus fucorum, Aplysia depilans, Arabidopsis thaliana, Aureoumbra lagunensis, Axinella aruensis, Axinella cannabina, Azadirachta indica, Azolla nilotica, Bombax anceps, Bugula neritina, Calophyllum inophyllum, Caulerpa prolifera, Clerodendrum chinense, Clerodendrum fragrans, Clerodendrum infortunatum, Cliona celata, Coccinella septempunctata, Cucurbita pepo, Cymodocea nodosa, Cystoseira barbata, Delisea pulchra, Dendronephthya hemprichi, Dictyuchus monosporus, Digitalis lanata, Digitalis purpurea, Diplopterygium glaucum, Dracaena cinnabari, Dragmacidon lunaecharta, Dysidea fragilis, Echinometra lucunter, Ulva linza, Eutreptia viridis, Ficus pumila, Gonimbrasia belina, Gracilaria gracilis, Gryllotalpa orientalis, Halocynthia aurantium, Helianthus annuus, Hibiscus sabdariffa, Holotrichia diomphalia, Hydrodictyon reticulatum, Tristagma uniflorum, Kalanchoe marmorata, Laurencia aldingensis, Laurencia obtusa, Melanothamnus somalensis, Neofibularia nolitangere, Nicotiana tabacum, Nigella sativa, Oocystis polymorpha, Pachliopta aristolochiae, Padina gymnospora, Palisada perforata, Palmaria palmata, Pelargonium hortorum, Petrosia ficiformis, Phallusia nigra, Phyllidiella pustulosa, Pseudophryne corroboree, Pyrocystis lunula, Rhinella arenarum, Salamandra salamandra, Salpa thompsoni, Salsola collina, Salvia fruticosa, Sambucus nigra, Sinapis alba, Solanum lanceolatum, Solanum palitans, Solanum virginianum, Sorghum bicolor, Triticum aestivum, Ulva lactuca, Viburnum opulus, Xestospongia testudinaria, Yucca glauca, Zea mays and Zoanthus sociatus. In healthy individuals the LDL particles are large and relatively few in number.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652310111700402D          

 28 31  0  0  0  0            999 V2000
    3.8779   -3.3644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5923   -2.1269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4502   -2.1269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7872   -1.9011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3053   -2.4768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0213   -2.9519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3068   -3.3644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7357   -3.3644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6364   -3.9119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8294   -4.0835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2509   -4.1848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0579   -4.3564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4012   -1.5581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9803   -2.0727    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5942   -1.7296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1733   -2.2442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6983   -2.9558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5923   -2.9519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4502   -2.9519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8913   -3.1273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9532   -2.1712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2774   -3.4704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1647   -3.3644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4704   -3.6419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5323   -2.6857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3393   -2.5142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9184   -3.0288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7602   -1.9996    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  7  6  1  0  0  0  0
  8  6  1  0  0  0  0
 10  9  1  0  0  0  0
 12 11  1  0  0  0  0
 15 13  1  0  0  0  0
 16 14  1  0  0  0  0
 18  1  1  0  0  0  0
 18  2  1  0  0  0  0
 18  7  1  0  0  0  0
 19  3  1  0  0  0  0
 19  8  1  0  0  0  0
 20  9  2  0  0  0  0
 20 17  1  0  0  0  0
 21 13  1  0  0  0  0
 21 17  1  0  0  0  0
 22 10  1  0  0  0  0
 23 11  1  0  0  0  0
 23 19  1  0  0  0  0
 24 12  1  0  0  0  0
 24 22  1  0  0  0  0
 25 14  1  0  0  0  0
 25 22  1  0  0  0  0
 26  4  1  0  0  0  0
 26 15  1  0  0  0  0
 26 20  1  0  0  0  0
 26 25  1  0  0  0  0
 27  5  1  0  0  0  0
 27 16  1  0  0  0  0
 27 23  1  0  0  0  0
 27 24  1  0  0  0  0
 28 21  1  0  0  0  0
M  END

     RDKit          3D

 74 77  0  0  0  0  0  0  0  0999 V2000
    8.4445   -1.2602    0.1324 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2601   -0.5196    0.7211 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9573   -1.1469    2.0540 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0941   -0.7253   -0.1851 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8418   -0.0236    0.3080 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6921   -0.2661   -0.6491 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4236    0.4314   -0.1770 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7436    1.9420   -0.1169 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2940    0.2374   -1.1395 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0091   -1.2460   -1.3736 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2068   -1.6592   -0.1929 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3671   -0.3971    0.4055 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8099   -0.6236    0.7030 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2912    0.1058    1.9254 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5853    0.8259    1.7193 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4633    0.4742    0.8149 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7443    1.1809    0.6059 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8647    0.2532    0.2533 C   0  0  1  0  0  0  0  0  0  0  0  0
   -7.9375    1.0292   -0.2435 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5371   -0.7778   -0.7769 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1078   -0.7820   -1.2181 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1570   -0.6944   -0.0517 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.2361   -2.0117    0.6892 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7191   -0.5216   -0.4868 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4795    0.6986   -1.3054 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0365    0.6846   -1.7576 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0602    0.6698   -0.6081 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1196    2.0450   -0.0123 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1823   -2.3261    0.0126 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.2744   -1.1655    0.8751 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7576   -0.7984   -0.8461 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4627    0.5501    0.8327 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3221   -0.4773    2.6702 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8992   -1.2990    2.6251 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4834   -2.1449    1.9372 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3180   -0.4251   -1.2486 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8917   -1.8152   -0.2365 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0113    1.0266    0.5752 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6052   -0.5303    1.2924 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5136   -1.3417   -0.6219 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9784    0.1573   -1.6246 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1432    0.1095    0.8104 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8096    2.3088    0.9167 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8031    2.1122   -0.5193 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1294    2.5127   -0.8156 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5323    0.7385   -2.0946 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8872   -1.8772   -1.4394 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4892   -1.3902   -2.3638 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5996   -2.3610   -0.5338 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7800   -2.2205    0.5706 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1435   -0.1271    1.3506 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8660   -1.7260    0.9948 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5022   -0.5856    2.7981 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5334    0.8103    2.3485 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7923    1.6799    2.3583 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6331    1.8928   -0.2635 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0492    1.7724    1.4820 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2537   -0.2166    1.2016 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8361    1.1407   -1.2317 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8956   -1.7592   -0.3979 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1435   -0.6234   -1.7204 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9838   -0.0072   -1.9764 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9263   -1.7722   -1.7161 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2052   -1.9189    1.7731 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2183   -2.5192    0.4588 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4779   -2.7407    0.2799 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4981   -1.4002   -1.1459 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7214    1.6496   -0.8370 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0862    0.6413   -2.2351 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9344   -0.0803   -2.5035 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8795    1.6764   -2.2769 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4957    2.2324    0.8542 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1923    2.1154    0.3994 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1359    2.8158   -0.8068 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  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  1
 22 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  1
 27  9  1  0
 27 12  1  0
 24 13  1  0
 22 16  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  2 32  1  0
  3 33  1  0
  3 34  1  0
  3 35  1  0
  4 36  1  0
  4 37  1  0
  5 38  1  0
  5 39  1  0
  6 40  1  0
  6 41  1  0
  7 42  1  1
  8 43  1  0
  8 44  1  0
  8 45  1  0
  9 46  1  6
 10 47  1  0
 10 48  1  0
 11 49  1  0
 11 50  1  0
 12 51  1  1
 13 52  1  1
 14 53  1  0
 14 54  1  0
 15 55  1  0
 17 56  1  0
 17 57  1  0
 18 58  1  1
 19 59  1  0
 20 60  1  0
 20 61  1  0
 21 62  1  0
 21 63  1  0
 23 64  1  0
 23 65  1  0
 23 66  1  0
 24 67  1  6
 25 68  1  0
 25 69  1  0
 26 70  1  0
 26 71  1  0
 28 72  1  0
 28 73  1  0
 28 74  1  0
M  END


  Mrv1652310111700402D          

 28 31  0  0  0  0            999 V2000
    3.8779   -3.3644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5923   -2.1269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4502   -2.1269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7872   -1.9011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3053   -2.4768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0213   -2.9519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3068   -3.3644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7357   -3.3644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6364   -3.9119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8294   -4.0835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2509   -4.1848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0579   -4.3564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4012   -1.5581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9803   -2.0727    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5942   -1.7296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1733   -2.2442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6983   -2.9558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5923   -2.9519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4502   -2.9519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8913   -3.1273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9532   -2.1712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2774   -3.4704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1647   -3.3644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4704   -3.6419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5323   -2.6857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3393   -2.5142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9184   -3.0288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7602   -1.9996    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  7  6  1  0  0  0  0
  8  6  1  0  0  0  0
 10  9  1  0  0  0  0
 12 11  1  0  0  0  0
 15 13  1  0  0  0  0
 16 14  1  0  0  0  0
 18  1  1  0  0  0  0
 18  2  1  0  0  0  0
 18  7  1  0  0  0  0
 19  3  1  0  0  0  0
 19  8  1  0  0  0  0
 20  9  2  0  0  0  0
 20 17  1  0  0  0  0
 21 13  1  0  0  0  0
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 22 10  1  0  0  0  0
 23 11  1  0  0  0  0
 23 19  1  0  0  0  0
 24 12  1  0  0  0  0
 24 22  1  0  0  0  0
 25 14  1  0  0  0  0
 25 22  1  0  0  0  0
 26  4  1  0  0  0  0
 26 15  1  0  0  0  0
 26 20  1  0  0  0  0
 26 25  1  0  0  0  0
 27  5  1  0  0  0  0
 27 16  1  0  0  0  0
 27 23  1  0  0  0  0
 27 24  1  0  0  0  0
 28 21  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0141985

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)CCCC(C)C1CCC2C3CC=C4CC(O)CCC4(C)C3CCC12C

> <INCHI_IDENTIFIER>
InChI=1S/C27H46O/c1-18(2)7-6-8-19(3)23-11-12-24-22-10-9-20-17-21(28)13-15-26(20,4)25(22)14-16-27(23,24)5/h9,18-19,21-25,28H,6-8,10-17H2,1-5H3

> <INCHI_KEY>
HVYWMOMLDIMFJA-UHFFFAOYSA-N

> <FORMULA>
C27H46O

> <MOLECULAR_WEIGHT>
386.6535

> <EXACT_MASS>
386.354866094

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
74

> <JCHEM_AVERAGE_POLARIZABILITY>
50.17813297327456

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
7.02

> <JCHEM_LOGP>
7.112889030666665

> <ALOGPS_LOGS>
-7.14

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.20428950550382

> <JCHEM_PKA_STRONGEST_BASIC>
-1.3972437702926293

> <JCHEM_POLAR_SURFACE_AREA>
20.23

> <JCHEM_REFRACTIVITY>
120.61649999999993

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.79e-05 g/l

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

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 11-OCT-17   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-OCT-17         0                                  
HETATM    1  C   UNK     0       7.239  -6.280   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.572  -3.970   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      13.907  -3.970   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      20.136  -3.549   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      15.503  -4.623   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      11.240  -5.510   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.906  -6.280   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      12.573  -6.280   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      21.721  -7.302   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      20.215  -7.622   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      15.402  -7.812   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      16.908  -8.132   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      23.149  -2.908   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      18.630  -3.869   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      21.643  -3.229   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      17.123  -4.189   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      23.703  -5.517   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.572  -5.510   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      13.907  -5.510   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      22.197  -5.838   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      24.179  -4.053   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      19.184  -6.478   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      15.241  -6.280   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      17.678  -6.798   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      19.660  -5.013   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      21.167  -4.693   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      16.648  -5.654   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      25.686  -3.733   0.000  0.00  0.00           O+0
CONECT    1   18                                                            
CONECT    2   18                                                            
CONECT    3   19                                                            
CONECT    4   26                                                            
CONECT    5   27                                                            
CONECT    6    7    8                                                       
CONECT    7    6   18                                                       
CONECT    8    6   19                                                       
CONECT    9   10   20                                                       
CONECT   10    9   22                                                       
CONECT   11   12   23                                                       
CONECT   12   11   24                                                       
CONECT   13   15   21                                                       
CONECT   14   16   25                                                       
CONECT   15   13   26                                                       
CONECT   16   14   27                                                       
CONECT   17   20   21                                                       
CONECT   18    1    2    7                                                  
CONECT   19    3    8   23                                                  
CONECT   20    9   17   26                                                  
CONECT   21   13   17   28                                                  
CONECT   22   10   24   25                                                  
CONECT   23   11   19   27                                                  
CONECT   24   12   22   27                                                  
CONECT   25   14   22   26                                                  
CONECT   26    4   15   20   25                                             
CONECT   27    5   16   23   24                                             
CONECT   28   21                                                            
MASTER        0    0    0    0    0    0    0    0   28    0   62    0
END

View in JSmol

Synonyms

Value	Source
Epicholesterol	MeSH

Chemical Formula

C₂₇H₄₆O

Average Mass

386.6535 Da

Monoisotopic Mass

386.35487 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

CC(C)CCCC(C)C1CCC2C3CC=C4CC(O)CCC4(C)C3CCC12C

InChI Identifier

InChI=1S/C27H46O/c1-18(2)7-6-8-19(3)23-11-12-24-22-10-9-20-17-21(28)13-15-26(20,4)25(22)14-16-27(23,24)5/h9,18-19,21-25,28H,6-8,10-17H2,1-5H3

InChI Key

HVYWMOMLDIMFJA-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Acanthaster planci	LOTUS Database	35616633
Achillea millefolium	LOTUS Database	35616633
Aframomum sceptrum	LOTUS Database	35616633
Ajuga reptans	LOTUS Database	35616633
Amaranthus caudatus	LOTUS Database	35616633
Amphilectus fucorum	LOTUS Database	35616633
Aplysia depilans	LOTUS Database	35616633
Arabidopsis thaliana	LOTUS Database	35616633
Aureoumbra lagunensis	LOTUS Database	35616633
Axinella aruensis	LOTUS Database	35616633
Axinella cannabina	LOTUS Database	35616633
Azadirachta indica	LOTUS Database	35616633
Azolla nilotica	LOTUS Database	35616633
Bombax anceps	LOTUS Database	35616633
Bugula neritina	LOTUS Database	35616633
Calophyllum inophyllum	LOTUS Database	35616633
Caulerpa prolifera	LOTUS Database	35616633
Clerodendrum chinense	LOTUS Database	35616633
Clerodendrum fragrans	LOTUS Database	35616633
Clerodendrum infortunatum	LOTUS Database	35616633
Cliona celata	LOTUS Database	35616633
Coccinella septempunctata	LOTUS Database	35616633
Cucurbita pepo	LOTUS Database	35616633
Cymodocea nodosa	LOTUS Database	35616633
Cystoseira barbata	LOTUS Database	35616633
Delisea pulchra	LOTUS Database	35616633
Dendronephthya hemprichi	LOTUS Database	35616633
Dictyuchus monosporus	LOTUS Database	35616633
Digitalis lanata	LOTUS Database	35616633
Digitalis purpurea	LOTUS Database	35616633
Diplopterygium glaucum	LOTUS Database	35616633
Dracaena cinnabari	LOTUS Database	35616633
Dragmacidon lunaecharta	LOTUS Database	35616633
Dysidea fragilis	LOTUS Database	35616633
Echinometra lucunter	LOTUS Database	35616633
Enteromorpha linza	LOTUS Database	35616633
Eutreptia viridis	LOTUS Database	35616633
Ficus pumila	LOTUS Database	35616633
Gonimbrasia belina	LOTUS Database	35616633
Gracilaria gracilis	LOTUS Database	35616633
Gryllotalpa orientalis	LOTUS Database	35616633
Halocynthia aurantium	LOTUS Database	35616633
Helianthus annuus	LOTUS Database	35616633
Hibiscus sabdariffa	LOTUS Database	35616633
Holotrichia diomphalia	LOTUS Database	35616633
Hydrodictyon reticulatum	LOTUS Database	35616633
Ipheion uniflorum	LOTUS Database	35616633
Kalanchoe marmorata	LOTUS Database	35616633
Laurencia aldingensis	LOTUS Database	35616633
Laurencia obtusa	LOTUS Database	35616633
Melanothamnus somalensis	LOTUS Database	35616633
Neofibularia nolitangere	LOTUS Database	35616633
Nicotiana tabacum	LOTUS Database	35616633
Nigella sativa	LOTUS Database	35616633
Oocystis polymorpha	LOTUS Database	35616633
Pachliopta aristolochiae	LOTUS Database	35616633
Padina gymnospora	LOTUS Database	35616633
Palisada perforata	LOTUS Database	35616633
Palmaria palmata	LOTUS Database	35616633
Pelargonium hortorum	LOTUS Database	35616633
Petrosia ficiformis	LOTUS Database	35616633
Phallusia nigra	LOTUS Database	35616633
Phyllidiella pustulosa	LOTUS Database	35616633
Pseudophryne corroboree	LOTUS Database	35616633
Pyrocystis lunula	LOTUS Database	35616633
Rhinella arenarum	LOTUS Database	35616633
Salamandra salamandra	LOTUS Database	35616633
Salpa thompsoni	LOTUS Database	35616633
Salsola collina	LOTUS Database	35616633
Salvia fruticosa	LOTUS Database	35616633
Sambucus nigra	LOTUS Database	35616633
Sinapis alba	LOTUS Database	35616633
Solanum lanceolatum	LOTUS Database	35616633
Solanum palitans	LOTUS Database	35616633
Solanum virginianum	LOTUS Database	35616633
Sorghum bicolor	LOTUS Database	35616633
Triticum aestivum	LOTUS Database	35616633
Ulva lactuca	LOTUS Database	35616633
Viburnum opulus	LOTUS Database	35616633
Xestospongia testudinaria	LOTUS Database	35616633
Yucca glauca Nutt.	LOTUS Database	35616633
Zea mays	LOTUS Database	35616633
Zoanthus sociatus	LOTUS Database	35616633

Chemical Taxonomy

Description

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

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Cholestane steroids

Direct Parent

Cholesterols and derivatives

Alternative Parents

Substituents

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

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

a 3-β-hydroxysterol (CHOLESTEROL )

Physical Properties

State

Not Available

Experimental 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

Predicted Properties

Property	Value	Source
logP	7.02	ALOGPS
logP	7.11	ChemAxon
logS	-7.1	ALOGPS
pKa (Strongest Acidic)	18.2	ChemAxon
pKa (Strongest Basic)	-1.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	20.23 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	120.62 m³·mol⁻¹	ChemAxon
Polarizability	50.18 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

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB013269

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Cholesterol

METLIN ID

Not Available

PubChem Compound

304

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for epicholestrol (NP0141985)

MOL for NP0141985 (epicholestrol)

3D MOL for NP0141985 (epicholestrol)

3D SDF for NP0141985 (epicholestrol)

3D-SDF for NP0141985 (epicholestrol)

PDB for NP0141985 (epicholestrol)

3D PDB for NP0141985 (epicholestrol)

SMILES for NP0141985 (epicholestrol)

INCHI for NP0141985 (epicholestrol)

Structure for NP0141985 (epicholestrol)

3D Structure for NP0141985 (epicholestrol)