NP-MRD: Showing NP-Card for (1r,3as,3bs,7s,9ar,9bs,11ar)-1-[(2r,3e,5s)-5,6-dimethylhept-3-en-2-yl]-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-ol (NP0280423)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-09 06:12:48 UTC

Updated at

2022-09-09 06:12:48 UTC

NP-MRD ID

NP0280423

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,3as,3bs,7s,9ar,9bs,11ar)-1-[(2r,3e,5s)-5,6-dimethylhept-3-en-2-yl]-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-ol

Description

Brassicasterol belongs to the class of organic compounds known as ergosterols and derivatives. These are steroids containing ergosta-5,7,22-trien-3beta-ol or a derivative thereof, which is based on the 3beta-hydroxylated ergostane skeleton. Thus, brassicasterol is considered to be a sterol lipid molecule. Its relatively high concentration and stability allows it to be used in the assessment of the origin of organic matter in samples, especially sediments. Brassicasterol is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Outside of the human body, brassicasterol is found, on average, in the highest concentration in common walnuts. Brassicasterol has also been detected, but not quantified in, several different foods, such as pecan nuts, pepper (c. Frutescens), redcurrants, alfalfa, and leeks. This could make brassicasterol a potential biomarker for the consumption of these foods. A list of the algae in which brassicasterol has been identified is shown below together with approximate composition. However, the cholesterol behaves in a similar manner, and the ratio brassicasterol/cholesterol is fairly uniform at all depths, indicating either a comparable degradation rate with no change in source or different degradation rates and a change in source. This means that, in most environmental systems, brassicasterol will be associated with the solid phase. The free sterols are then separated from the polar lipids by partitioning into a less polar solvent (e.G, hexane). (1r,3as,3bs,7s,9ar,9bs,11ar)-1-[(2r,3e,5s)-5,6-dimethylhept-3-en-2-yl]-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-ol is found in Alitta succinea, Aplysina fistularis, Aureoumbra lagunensis, Axinella aruensis, Axinella cannabina, Baccharoides anthelmintica, Brassica juncea, Bugula neritina, Cymodocea nodosa, Dicrateria inornata, Diplopterygium glaucum, Dragmacidon lunaecharta, Echinometra lucunter, Haliclona oculata, Hydrodictyon reticulatum, Kalanchoe petitiana, Mikania campanulata, Nervilia plicata, Petrosia weinbergi, Phallusia nigra, Chrysotila lamellosa, Tuber melanosporum and Verongula gigantea. The mass spectrum for the TMS ether of brassicasterol can be seen in the figure.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652306222023592D          

 38 41  0  0  1  0            999 V2000
   -2.4048    2.5820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2767    3.4590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3921    1.2793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3705    2.3821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5466    1.3336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0307    1.7357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2640    2.1564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2424    1.5050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5754   -0.8489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7633   -0.7037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3367    0.1741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0195   -0.2889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1708    1.0432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7345    1.4789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3587    1.1884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9224    1.6241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9193   -0.3634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5876    2.6948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0812    2.0435    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0596    1.6179    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.1072   -0.2182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4511    0.2673    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4830    0.0722    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5660    0.9666    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6708    0.2174    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0148    0.7029    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.8269    0.5577    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3905    0.9934    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.2632    0.1221    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0469    2.9205    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0685    0.7409    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5749    1.3922    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5533    2.2692    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7314   -0.5086    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9511   -0.5585    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7557    0.8111    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2027    0.8481    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2951   -0.0730    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  8  7  2  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
 19  3  1  1  0  0  0
 19  7  1  0  0  0  0
 19 18  1  0  0  0  0
 20  4  1  1  0  0  0
 20  8  1  0  0  0  0
 21  9  2  0  0  0  0
 21 17  1  0  0  0  0
 22 13  1  0  0  0  0
 22 17  1  0  0  0  0
 23 10  1  0  0  0  0
 24 11  1  0  0  0  0
 24 20  1  6  0  0  0
 25 12  1  0  0  0  0
 25 23  1  0  0  0  0
 26 14  1  0  0  0  0
 26 23  1  0  0  0  0
 27  5  1  6  0  0  0
 27 15  1  0  0  0  0
 27 21  1  0  0  0  0
 27 26  1  0  0  0  0
 28  6  1  6  0  0  0
 28 16  1  0  0  0  0
 28 24  1  0  0  0  0
 28 25  1  0  0  0  0
 22 29  1  6  0  0  0
 30  7  1  0  0  0  0
 31  8  1  0  0  0  0
 19 32  1  6  0  0  0
 20 33  1  6  0  0  0
 22 34  1  1  0  0  0
 23 35  1  6  0  0  0
 24 36  1  1  0  0  0
 25 37  1  1  0  0  0
 26 38  1  1  0  0  0
M  END

     RDKit          3D

 75 78  0  0  0  0  0  0  0  0999 V2000
    7.3576   -1.8323   -1.2186 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4709   -1.4760   -0.0546 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2976   -0.7023    0.9384 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3212   -0.6073   -0.5583 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.8744    0.5750   -1.2898 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4176   -0.2320    0.5641 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1242   -0.5727    0.5643 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1787   -0.2457    1.6188 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9776    0.4689    2.7288 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0141    0.5792    1.3274 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2514    1.9768    0.8077 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0698    2.3859    0.1217 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9670    1.2410    0.4691 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1687    1.0177   -0.3362 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0584    2.2237   -0.4108 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4314    2.0165    0.0438 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9984    0.8269    0.0779 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3831    0.6789    0.5439 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0755   -0.3711   -0.2637 C   0  0  1  0  0  0  0  0  0  0  0  0
   -7.1223    0.0604   -1.6057 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3544   -1.6698   -0.1409 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9103   -1.5743    0.2156 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2268   -0.3650   -0.3484 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.1495   -0.4760   -1.8516 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8659   -0.2036    0.2824 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9837   -1.3939    0.0820 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6505   -1.1776    0.6977 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0262    0.0782    0.2868 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5861    0.0362   -1.0933 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1957   -1.1232   -1.3644 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8271   -2.8282   -1.0106 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7909   -1.8554   -2.1819 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0844   -2.4120    0.3926 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2929   -1.2415    1.9069 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8610    0.3101    1.1030 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3528   -0.5819    0.5959 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7406   -1.2348   -1.2734 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0397    0.3683   -2.3777 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2789    1.5025   -1.1497 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8823    0.7949   -0.8784 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8411    0.3277    1.3829 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8167   -1.1479   -0.2952 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8061   -1.1728    2.1533 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8308   -0.1301    3.0744 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3643    1.3918    2.2663 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3208    0.6691    3.5995 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3751    0.6476    2.2747 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4221    2.6609    1.6729 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0243    2.0247    0.0536 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0591    2.5611   -0.9430 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4492    3.3086    0.6056 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2019    1.2821    1.5568 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9169    0.6947   -1.3796 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5546    3.0327    0.1768 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0705    2.6208   -1.4652 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9913    2.9230    0.3675 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9322    1.6503    0.5529 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3449    0.3433    1.6219 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1409   -0.4405    0.0635 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1003    1.0478   -1.6694 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5471   -2.2605   -1.0602 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8608   -2.2506    0.6832 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3917   -2.4796   -0.2037 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7803   -1.6400    1.3162 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8146   -1.3027   -2.2273 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5042    0.4777   -2.3253 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1440   -0.6825   -2.2424 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0087    0.0270    1.3490 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9642   -1.7229   -0.9606 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4705   -2.2426    0.6475 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0132   -2.0373    0.3898 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7612   -1.2051    1.8026 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0641    0.5128   -1.8757 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5619    0.5594   -1.2246 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7504   -1.0127   -1.4414 H   0  0  0  0  0  0  0  0  0  0  0  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  8 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  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  6
 23 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  6
  6  4  1  0
  4  5  1  0
  4  2  1  0
  2  1  1  0
  2  3  1  0
 28 10  1  0
 28 13  1  0
 25 14  1  0
 23 17  1  0
  6 41  1  0
  7 42  1  0
  8 43  1  1
  9 44  1  0
  9 45  1  0
  9 46  1  0
 10 47  1  1
 11 48  1  0
 11 49  1  0
 12 50  1  0
 12 51  1  0
 13 52  1  1
 14 53  1  6
 15 54  1  0
 15 55  1  0
 16 56  1  0
 18 57  1  0
 18 58  1  0
 19 59  1  1
 20 60  1  0
 21 61  1  0
 21 62  1  0
 22 63  1  0
 22 64  1  0
 24 65  1  0
 24 66  1  0
 24 67  1  0
 25 68  1  1
 26 69  1  0
 26 70  1  0
 27 71  1  0
 27 72  1  0
 29 73  1  0
 29 74  1  0
 29 75  1  0
  4 37  1  6
  5 38  1  0
  5 39  1  0
  5 40  1  0
  2 33  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  3 34  1  0
  3 35  1  0
  3 36  1  0
M  END


  Mrv1652306222023592D          

 38 41  0  0  1  0            999 V2000
   -2.4048    2.5820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2767    3.4590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3921    1.2793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3705    2.3821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5466    1.3336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0307    1.7357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2640    2.1564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2424    1.5050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5754   -0.8489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7633   -0.7037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3367    0.1741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0195   -0.2889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1708    1.0432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7345    1.4789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3587    1.1884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9224    1.6241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9193   -0.3634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5876    2.6948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0812    2.0435    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0596    1.6179    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.1072   -0.2182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4511    0.2673    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4830    0.0722    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5660    0.9666    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6708    0.2174    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0148    0.7029    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.8269    0.5577    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3905    0.9934    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.2632    0.1221    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0469    2.9205    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0685    0.7409    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5749    1.3922    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5533    2.2692    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7314   -0.5086    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9511   -0.5585    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7557    0.8111    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2027    0.8481    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2951   -0.0730    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  8  7  2  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
 19  3  1  1  0  0  0
 19  7  1  0  0  0  0
 19 18  1  0  0  0  0
 20  4  1  1  0  0  0
 20  8  1  0  0  0  0
 21  9  2  0  0  0  0
 21 17  1  0  0  0  0
 22 13  1  0  0  0  0
 22 17  1  0  0  0  0
 23 10  1  0  0  0  0
 24 11  1  0  0  0  0
 24 20  1  6  0  0  0
 25 12  1  0  0  0  0
 25 23  1  0  0  0  0
 26 14  1  0  0  0  0
 26 23  1  0  0  0  0
 27  5  1  6  0  0  0
 27 15  1  0  0  0  0
 27 21  1  0  0  0  0
 27 26  1  0  0  0  0
 28  6  1  6  0  0  0
 28 16  1  0  0  0  0
 28 24  1  0  0  0  0
 28 25  1  0  0  0  0
 22 29  1  6  0  0  0
 30  7  1  0  0  0  0
 31  8  1  0  0  0  0
 19 32  1  6  0  0  0
 20 33  1  6  0  0  0
 22 34  1  1  0  0  0
 23 35  1  6  0  0  0
 24 36  1  1  0  0  0
 25 37  1  1  0  0  0
 26 38  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0280423

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]\C(=C(\[H])[C@@]([H])(C)[C@@]1([H])CC[C@@]2([H])[C@]3([H])CC=C4C[C@@]([H])(O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@@]([H])(C)C(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C28H46O/c1-18(2)19(3)7-8-20(4)24-11-12-25-23-10-9-21-17-22(29)13-15-27(21,5)26(23)14-16-28(24,25)6/h7-9,18-20,22-26,29H,10-17H2,1-6H3/b8-7+/t19-,20-,22+,23+,24-,25+,26+,27+,28-/m1/s1

> <INCHI_KEY>
OILXMJHPFNGGTO-SDMVIZLASA-N

> <FORMULA>
C28H46O

> <MOLECULAR_WEIGHT>
398.6642

> <EXACT_MASS>
398.354866094

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
75

> <JCHEM_AVERAGE_POLARIZABILITY>
50.795204354444316

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,2R,5S,10S,11S,14R,15R)-14-[(2R,3E,5S)-5,6-dimethylhept-3-en-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-5-ol

> <ALOGPS_LOGP>
6.48

> <JCHEM_LOGP>
7.037986470333335

> <ALOGPS_LOGS>
-7.06

> <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>
126.28169999999993

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.47e-05 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2R,5S,10S,11S,14R,15R)-14-[(2R,3E,5S)-5,6-dimethylhept-3-en-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-5-ol

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 22-JUN-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   22-JUN-20         0                                  
HETATM    1  C   UNK     0      -4.489   4.820   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.383   6.457   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.599   2.388   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.558   4.447   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.487   2.489   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.791   3.240   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.493   4.025   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.452   2.809   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.541  -1.585   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.025  -1.314   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.495   0.325   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.770  -0.539   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      11.519   1.947   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.971   2.761   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      10.003   2.218   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.455   3.032   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      11.049  -0.678   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -2.964   5.030   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -2.018   3.815   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.978   3.020   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       9.533  -0.407   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      12.042   0.499   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       6.502   0.135   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       2.923   1.804   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       4.985   0.406   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       7.494   1.312   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       9.010   1.041   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       4.462   1.854   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      13.558   0.228   0.000  0.00  0.00           O+0
HETATM   30  H   UNK     0       0.088   5.452   0.000  0.00  0.00           H+0
HETATM   31  H   UNK     0      -0.128   1.383   0.000  0.00  0.00           H+0
HETATM   32  H   UNK     0      -1.073   2.599   0.000  0.00  0.00           H+0
HETATM   33  H   UNK     0       1.033   4.236   0.000  0.00  0.00           H+0
HETATM   34  H   UNK     0      12.565  -0.949   0.000  0.00  0.00           H+0
HETATM   35  H   UNK     0       5.509  -1.043   0.000  0.00  0.00           H+0
HETATM   36  H   UNK     0       1.411   1.514   0.000  0.00  0.00           H+0
HETATM   37  H   UNK     0       5.978   1.583   0.000  0.00  0.00           H+0
HETATM   38  H   UNK     0       8.018  -0.136   0.000  0.00  0.00           H+0
CONECT    1   18                                                            
CONECT    2   18                                                            
CONECT    3   19                                                            
CONECT    4   20                                                            
CONECT    5   27                                                            
CONECT    6   28                                                            
CONECT    7    8   19   30                                                  
CONECT    8    7   20   31                                                  
CONECT    9   10   21                                                       
CONECT   10    9   23                                                       
CONECT   11   12   24                                                       
CONECT   12   11   25                                                       
CONECT   13   15   22                                                       
CONECT   14   16   26                                                       
CONECT   15   13   27                                                       
CONECT   16   14   28                                                       
CONECT   17   21   22                                                       
CONECT   18    1    2   19                                                  
CONECT   19    3    7   18   32                                             
CONECT   20    4    8   24   33                                             
CONECT   21    9   17   27                                                  
CONECT   22   13   17   29   34                                             
CONECT   23   10   25   26   35                                             
CONECT   24   11   20   28   36                                             
CONECT   25   12   23   28   37                                             
CONECT   26   14   23   27   38                                             
CONECT   27    5   15   21   26                                             
CONECT   28    6   16   24   25                                             
CONECT   29   22                                                            
CONECT   30    7                                                            
CONECT   31    8                                                            
CONECT   32   19                                                            
CONECT   33   20                                                            
CONECT   34   22                                                            
CONECT   35   23                                                            
CONECT   36   24                                                            
CONECT   37   25                                                            
CONECT   38   26                                                            
MASTER        0    0    0    0    0    0    0    0   38    0   82    0
END

View in JSmol

Synonyms

Value	Source
24(R)-Methylcholesta-5,22E-dien-3beta-ol	HMDB
24-Methylcholesta-5,22-dien-3beta-ol	HMDB
5,22-Ergostadien-3beta-ol	HMDB
5,22-Ergostadienol	HMDB
Brassicasterin	HMDB
Ergosta-5,22(e)-dien-3beta-ol	HMDB
Ergosta-5,22-dien-3beta-ol	HMDB
delta25-Crinosterol	HMDB
Crinosterol	MeSH

Chemical Formula

C₂₈H₄₆O

Average Mass

398.6642 Da

Monoisotopic Mass

398.35487 Da

IUPAC Name

(1S,2R,5S,10S,11S,14R,15R)-14-[(2R,3E,5S)-5,6-dimethylhept-3-en-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-5-ol

Traditional Name

(1S,2R,5S,10S,11S,14R,15R)-14-[(2R,3E,5S)-5,6-dimethylhept-3-en-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-5-ol

CAS Registry Number

Not Available

SMILES

[H]\C(=C(\[H])[C@@]([H])(C)[C@@]1([H])CC[C@@]2([H])[C@]3([H])CC=C4C[C@@]([H])(O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@@]([H])(C)C(C)C

InChI Identifier

InChI=1S/C28H46O/c1-18(2)19(3)7-8-20(4)24-11-12-25-23-10-9-21-17-22(29)13-15-27(21,5)26(23)14-16-28(24,25)6/h7-9,18-20,22-26,29H,10-17H2,1-6H3/b8-7+/t19-,20-,22+,23+,24-,25+,26+,27+,28-/m1/s1

InChI Key

OILXMJHPFNGGTO-SDMVIZLASA-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
Alitta succinea	LOTUS Database	35616633
Aplysina fistularis	LOTUS Database	35616633
Aureoumbra lagunensis	LOTUS Database	35616633
Axinella aruensis	LOTUS Database	35616633
Axinella cannabina	LOTUS Database	35616633
Baccharoides anthelmintica	LOTUS Database	35616633
Brassica juncea	LOTUS Database	35616633
Bugula neritina	LOTUS Database	35616633
Cymodocea nodosa	LOTUS Database	35616633
Dicrateria inornata	LOTUS Database	35616633
Diplopterygium glaucum	LOTUS Database	35616633
Dragmacidon lunaecharta	LOTUS Database	35616633
Echinometra lucunter	LOTUS Database	35616633
Haliclona oculata	LOTUS Database	35616633
Hydrodictyon reticulatum	LOTUS Database	35616633
Kalanchoe petitiana	LOTUS Database	35616633
Mikania campanulata	LOTUS Database	35616633
Nervilia plicata	LOTUS Database	35616633
Petrosia weinbergi	LOTUS Database	35616633
Phallusia nigra	LOTUS Database	35616633
Ruttnera lamellosa	LOTUS Database	35616633
Tuber melanosporum	LOTUS Database	35616633
Verongula gigantea	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as ergosterols and derivatives. These are steroids containing ergosta-5,7,22-trien-3beta-ol or a derivative thereof, which is based on the 3beta-hydroxylated ergostane skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Ergostane steroids

Direct Parent

Ergosterols and derivatives

Alternative Parents

Not Available

Substituents

Not Available

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

Not Available

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	6.48	ALOGPS
logP	7.04	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	4	ChemAxon
Refractivity	126.28 m³·mol⁻¹	ChemAxon
Polarizability	50.8 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

HMDB0011181

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Brassicasterol

METLIN ID

Not Available

PubChem Compound

5283660

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1r,3as,3bs,7s,9ar,9bs,11ar)-1-[(2r,3e,5s)-5,6-dimethylhept-3-en-2-yl]-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-ol (NP0280423)

MOL for NP0280423 ((1r,3as,3bs,7s,9ar,9bs,11ar)-1-[(2r,3e,5s)-5,6-dimethylhept-3-en-2-yl]-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-ol)

3D MOL for NP0280423 ((1r,3as,3bs,7s,9ar,9bs,11ar)-1-[(2r,3e,5s)-5,6-dimethylhept-3-en-2-yl]-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-ol)

3D SDF for NP0280423 ((1r,3as,3bs,7s,9ar,9bs,11ar)-1-[(2r,3e,5s)-5,6-dimethylhept-3-en-2-yl]-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-ol)

3D-SDF for NP0280423 ((1r,3as,3bs,7s,9ar,9bs,11ar)-1-[(2r,3e,5s)-5,6-dimethylhept-3-en-2-yl]-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-ol)

PDB for NP0280423 ((1r,3as,3bs,7s,9ar,9bs,11ar)-1-[(2r,3e,5s)-5,6-dimethylhept-3-en-2-yl]-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-ol)

3D PDB for NP0280423 ((1r,3as,3bs,7s,9ar,9bs,11ar)-1-[(2r,3e,5s)-5,6-dimethylhept-3-en-2-yl]-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-ol)

SMILES for NP0280423 ((1r,3as,3bs,7s,9ar,9bs,11ar)-1-[(2r,3e,5s)-5,6-dimethylhept-3-en-2-yl]-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-ol)

INCHI for NP0280423 ((1r,3as,3bs,7s,9ar,9bs,11ar)-1-[(2r,3e,5s)-5,6-dimethylhept-3-en-2-yl]-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-ol)

Structure for NP0280423 ((1r,3as,3bs,7s,9ar,9bs,11ar)-1-[(2r,3e,5s)-5,6-dimethylhept-3-en-2-yl]-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-ol)

3D Structure for NP0280423 ((1r,3as,3bs,7s,9ar,9bs,11ar)-1-[(2r,3e,5s)-5,6-dimethylhept-3-en-2-yl]-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-ol)