NP-MRD: Showing NP-Card for Bryoferulic acid (NP0084965)

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Record Information

Version

2.0

Created at

2022-04-29 05:34:09 UTC

Updated at

2022-04-29 05:34:09 UTC

NP-MRD ID

NP0084965

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Bryoferulic acid

Description

(2R,4aS,6aS,8aR,10S,12aS,14aS,14bR)-10-{[(2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}-2,4a,6a,9,9,12a,14a-heptamethyl-1,2,3,4,4a,5,6,6a,8,8a,9,10,11,12,12a,14,14a,14b-octadecahydropicene-2-carboxylic acid belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. Bryoferulic acid is found in Glomus caledonium and Momordica charantia. Based on a literature review very few articles have been published on (2R,4aS,6aS,8aR,10S,12aS,14aS,14bR)-10-{[(2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}-2,4a,6a,9,9,12a,14a-heptamethyl-1,2,3,4,4a,5,6,6a,8,8a,9,10,11,12,12a,14,14a,14b-octadecahydropicene-2-carboxylic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304292207342D          

 48 53  0  0  1  0            999 V2000
    3.6703   -3.8716    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8136   -3.0591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1816   -2.5288    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5888   -2.7770    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.7321   -3.5894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1763   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5888   -1.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4138   -1.3480    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0013   -0.6336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8263   -0.6336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6513   -0.6336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0638   -1.3480    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.4763   -0.6336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8888   -1.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3013   -0.6336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1263   -0.6336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5388   -1.3480    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.9513   -2.0625    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.3638   -1.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2205   -0.5356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1390   -1.0659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7763   -2.0625    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   11.6013   -2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.0138   -1.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8388   -1.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2513   -0.6336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0763   -0.6336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4888    0.0809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3138    0.0809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7263    0.7954    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.3138    1.5099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7263   -0.6336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5513   -0.6336    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.3138   -1.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4888   -1.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6013   -0.6336    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.3638   -2.7770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5388   -2.7770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1263   -2.0625    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.7138   -2.7770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3013   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8888   -2.7770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0638   -2.7770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6513   -2.0625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.2388   -2.7770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8263   -2.0625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0013   -2.0625    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4138   -2.7770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  4  2  1  6  0  0  0
  4  5  1  1  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  1  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  1  0  0  0
 12 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  6  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
 19 22  1  0  0  0  0
 22 23  1  1  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 29 32  2  0  0  0  0
 32 33  1  0  0  0  0
 32 34  1  0  0  0  0
 34 35  2  0  0  0  0
 27 35  1  0  0  0  0
 24 36  2  0  0  0  0
 22 37  1  0  0  0  0
 37 38  1  0  0  0  0
 38 39  1  0  0  0  0
 17 39  1  0  0  0  0
 39 40  1  1  0  0  0
 39 41  1  0  0  0  0
 14 41  1  0  0  0  0
 41 42  2  0  0  0  0
 42 43  1  0  0  0  0
 43 44  1  0  0  0  0
 12 44  1  0  0  0  0
 44 45  1  6  0  0  0
 44 46  1  0  0  0  0
  8 46  1  0  0  0  0
 46 47  1  1  0  0  0
 46 48  1  0  0  0  0
  4 48  1  0  0  0  0
M  END

     RDKit          3D

100105  0  0  0  0  0  0  0  0999 V2000
   12.5371   -0.2781    2.3526 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5832   -0.5225    0.9683 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.4562   -0.5138    0.1682 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2069   -0.2654    0.6667 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0859   -0.2631   -0.1666 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8056    0.0065    0.4424 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6370    0.0468   -0.1750 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4035    0.3302    0.5471 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4462    0.5394    1.7558 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2272    0.3605   -0.1132 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9494    0.6213    0.4604 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3896    1.9374    0.0124 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9391    2.0320    0.4226 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1992    1.0379   -0.4206 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3760    1.3039   -1.8918 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2705    1.0850   -0.1943 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9399    1.9577    0.4939 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3971    1.9316    0.7323 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9925    0.5644    0.3722 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.3786   -0.3802    1.4033 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4967    0.5774    0.4997 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.8504   -0.1613    1.7580 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3055   -0.5429    1.9048 C   0  0  2  0  0  0  0  0  0  0  0  0
   -8.2381    0.6032    2.0644 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3824   -1.4950    3.0517 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3918   -1.8568    3.7276 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6273   -2.0083    3.3866 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5959   -1.3916    0.6567 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6432   -0.3815   -0.4286 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2662    0.2330   -0.7163 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.6539    1.5252   -1.4660 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6109   -0.7392   -1.6467 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1837   -1.0440   -1.4205 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4572    0.1828   -0.9588 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.5701    1.2442   -2.0373 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9912   -0.0310   -0.8019 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3443   -1.1236   -1.1936 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1232   -1.3154   -1.0624 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6312   -0.3480   -0.0183 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0349   -0.5419    0.3790 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6793   -1.5147   -0.6266 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0876   -1.3292    1.7057 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1934   -0.5064   -1.4985 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4726   -0.7608   -2.0100 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5748   -0.7614   -1.1804 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8148   -1.0233   -1.7641 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.8376    0.5483    2.5527 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.1975   -1.1749    2.9238 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.5410    0.0420    2.7141 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.0874   -0.0703    1.7132 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7503    0.2013    1.5183 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6183   -0.1371   -1.2346 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2023    0.7863    1.5349 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5269    2.1796   -1.0370 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8874    2.7970    0.5620 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6258    3.0889    0.2084 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8607    1.7618    1.4788 H   0  0  0  0  0  0  0  0  0  0  0  0
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    1.3872    1.0494   -2.2665 H   0  0  0  0  0  0  0  0  0  0  0  0
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   10.5545   -0.9549   -3.0737 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.6289   -1.0266   -1.1648 H   0  0  0  0  0  0  0  0  0  0  0  0
 39 38  1  0
 38 37  1  0
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 20 65  1  0
 20 66  1  0
 21 67  1  1
 22 68  1  0
 22 69  1  0
 24 70  1  0
 24 71  1  0
 24 72  1  0
 28 74  1  0
 28 75  1  0
 29 76  1  0
 29 77  1  0
 31 78  1  0
 31 79  1  0
 31 80  1  0
 32 81  1  0
 32 82  1  0
 33 83  1  0
 33 84  1  0
 35 85  1  0
 35 86  1  0
 35 87  1  0
 27 73  1  0
 15 58  1  0
 15 59  1  0
 15 60  1  0
 13 56  1  0
 13 57  1  0
 12 54  1  0
 12 55  1  0
 11 53  1  1
  7 52  1  0
  6 51  1  0
  4 50  1  0
  1 47  1  0
  1 48  1  0
  1 49  1  0
 46100  1  0
 44 99  1  0
 43 98  1  0
 41 92  1  0
 41 93  1  0
 41 94  1  0
 42 95  1  0
 42 96  1  0
 42 97  1  0
M  END


  Mrv1652304292207342D          

 48 53  0  0  1  0            999 V2000
    3.6703   -3.8716    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8136   -3.0591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1816   -2.5288    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5888   -2.7770    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.7321   -3.5894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1763   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5888   -1.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4138   -1.3480    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0013   -0.6336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8263   -0.6336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6513   -0.6336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0638   -1.3480    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.4763   -0.6336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8888   -1.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3013   -0.6336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1263   -0.6336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5388   -1.3480    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.9513   -2.0625    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.3638   -1.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2205   -0.5356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1390   -1.0659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7763   -2.0625    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   11.6013   -2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.0138   -1.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8388   -1.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2513   -0.6336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0763   -0.6336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4888    0.0809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3138    0.0809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7263    0.7954    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.3138    1.5099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7263   -0.6336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5513   -0.6336    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.3138   -1.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4888   -1.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6013   -0.6336    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.3638   -2.7770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5388   -2.7770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1263   -2.0625    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.7138   -2.7770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3013   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8888   -2.7770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0638   -2.7770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6513   -2.0625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.2388   -2.7770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8263   -2.0625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0013   -2.0625    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4138   -2.7770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  4  2  1  6  0  0  0
  4  5  1  1  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  1  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  1  0  0  0
 12 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  6  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
 19 22  1  0  0  0  0
 22 23  1  1  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 29 32  2  0  0  0  0
 32 33  1  0  0  0  0
 32 34  1  0  0  0  0
 34 35  2  0  0  0  0
 27 35  1  0  0  0  0
 24 36  2  0  0  0  0
 22 37  1  0  0  0  0
 37 38  1  0  0  0  0
 38 39  1  0  0  0  0
 17 39  1  0  0  0  0
 39 40  1  1  0  0  0
 39 41  1  0  0  0  0
 14 41  1  0  0  0  0
 41 42  2  0  0  0  0
 42 43  1  0  0  0  0
 43 44  1  0  0  0  0
 12 44  1  0  0  0  0
 44 45  1  6  0  0  0
 44 46  1  0  0  0  0
  8 46  1  0  0  0  0
 46 47  1  1  0  0  0
 46 48  1  0  0  0  0
  4 48  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0084965

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@]12CC=C3C(=CC[C@@]4(C)[C@]5([H])C[C@@](C)(CC[C@]5(C)CC[C@]34C)C(O)=O)[C@@]1(C)CC[C@H](OC(=O)\C=C\C1=CC(OC)=C(O)C=C1)C2(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C40H54O6/c1-35(2)30-13-11-27-26(15-18-40(7)31-24-37(4,34(43)44)20-19-36(31,3)21-22-39(27,40)6)38(30,5)17-16-32(35)46-33(42)14-10-25-9-12-28(41)29(23-25)45-8/h9-12,14-15,23,30-32,41H,13,16-22,24H2,1-8H3,(H,43,44)/b14-10+/t30-,31+,32-,36+,37+,38+,39+,40-/m0/s1

> <INCHI_KEY>
MKXOPSSUNSEZJV-COSPWPRJSA-N

> <FORMULA>
C40H54O6

> <MOLECULAR_WEIGHT>
630.866

> <EXACT_MASS>
630.392039459

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
100

> <JCHEM_AVERAGE_POLARIZABILITY>
73.02044817711831

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R,4aS,6aS,8aR,10S,12aS,14aS,14bR)-10-{[(2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}-2,4a,6a,9,9,12a,14a-heptamethyl-1,2,3,4,4a,5,6,6a,8,8a,9,10,11,12,12a,14,14a,14b-octadecahydropicene-2-carboxylic acid

> <ALOGPS_LOGP>
8.23

> <JCHEM_LOGP>
8.761908082666666

> <ALOGPS_LOGS>
-6.40

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.86776324401447

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.587595840866233

> <JCHEM_PKA_STRONGEST_BASIC>
-4.888815256862756

> <JCHEM_POLAR_SURFACE_AREA>
93.06

> <JCHEM_REFRACTIVITY>
182.48629999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.53e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R,4aS,6aS,8aR,10S,12aS,14aS,14bR)-10-{[(2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}-2,4a,6a,9,9,12a,14a-heptamethyl-1,3,4,5,6,8,8a,10,11,12,14,14b-dodecahydropicene-2-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-APR-22         0                                  
HETATM    1  O   UNK     0       6.851  -7.227   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       7.119  -5.710   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       5.939  -4.720   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       8.566  -5.184   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.833  -6.700   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.796  -3.850   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.566  -2.516   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      10.106  -2.516   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.336  -1.183   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      10.876  -1.183   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      12.416  -1.183   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      13.186  -2.516   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      13.956  -1.183   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      14.726  -2.516   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      15.496  -1.183   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      17.036  -1.183   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      17.806  -2.516   0.000  0.00  0.00           C+0
HETATM   18  H   UNK     0      18.576  -3.850   0.000  0.00  0.00           H+0
HETATM   19  C   UNK     0      19.346  -2.516   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      19.078  -1.000   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      20.793  -1.990   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      20.116  -3.850   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      21.656  -3.850   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      22.426  -2.516   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      23.966  -2.516   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      24.736  -1.183   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      26.276  -1.183   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      27.046   0.151   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      28.586   0.151   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      29.356   1.485   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      28.586   2.818   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      29.356  -1.183   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      30.896  -1.183   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      28.586  -2.516   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      27.046  -2.516   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      21.656  -1.183   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0      19.346  -5.184   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      17.806  -5.184   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      17.036  -3.850   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      16.266  -5.184   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      15.496  -3.850   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      14.726  -5.184   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0      13.186  -5.184   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0      12.416  -3.850   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0      11.646  -5.184   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0      10.876  -3.850   0.000  0.00  0.00           C+0
HETATM   47  H   UNK     0       9.336  -3.850   0.000  0.00  0.00           H+0
HETATM   48  C   UNK     0      10.106  -5.184   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5    6   48                                             
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10   46                                             
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   14   44                                             
CONECT   13   12                                                            
CONECT   14   12   15   41                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   19   39                                             
CONECT   18   17                                                            
CONECT   19   17   20   21   22                                             
CONECT   20   19                                                            
CONECT   21   19                                                            
CONECT   22   19   23   37                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25   36                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28   35                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30   32                                                  
CONECT   30   29   31                                                       
CONECT   31   30                                                            
CONECT   32   29   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32   35                                                       
CONECT   35   34   27                                                       
CONECT   36   24                                                            
CONECT   37   22   38                                                       
CONECT   38   37   39                                                       
CONECT   39   38   17   40   41                                             
CONECT   40   39                                                            
CONECT   41   39   14   42                                                  
CONECT   42   41   43                                                       
CONECT   43   42   44                                                       
CONECT   44   43   12   45   46                                             
CONECT   45   44                                                            
CONECT   46   44    8   47   48                                             
CONECT   47   46                                                            
CONECT   48   46    4                                                       
MASTER        0    0    0    0    0    0    0    0   48    0  106    0
END

View in JSmol

Synonyms

Value	Source
(2R,4AS,6as,8ar,10S,12as,14as,14BR)-10-{[(2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}-2,4a,6a,9,9,12a,14a-heptamethyl-1,2,3,4,4a,5,6,6a,8,8a,9,10,11,12,12a,14,14a,14b-octadecahydropicene-2-carboxylate	Generator

Chemical Formula

C₄₀H₅₄O₆

Average Mass

630.8660 Da

Monoisotopic Mass

630.39204 Da

IUPAC Name

Traditional Name

(2R,4aS,6aS,8aR,10S,12aS,14aS,14bR)-10-{[(2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}-2,4a,6a,9,9,12a,14a-heptamethyl-1,3,4,5,6,8,8a,10,11,12,14,14b-dodecahydropicene-2-carboxylic acid

CAS Registry Number

Not Available

SMILES

[H][C@@]12CC=C3C(=CC[C@@]4(C)[C@]5([H])C[C@@](C)(CC[C@]5(C)CC[C@]34C)C(O)=O)[C@@]1(C)CC[C@H](OC(=O)\C=C\C1=CC(OC)=C(O)C=C1)C2(C)C

InChI Identifier

InChI=1S/C40H54O6/c1-35(2)30-13-11-27-26(15-18-40(7)31-24-37(4,34(43)44)20-19-36(31,3)21-22-39(27,40)6)38(30,5)17-16-32(35)46-33(42)14-10-25-9-12-28(41)29(23-25)45-8/h9-12,14-15,23,30-32,41H,13,16-22,24H2,1-8H3,(H,43,44)/b14-10+/t30-,31+,32-,36+,37+,38+,39+,40-/m0/s1

InChI Key

MKXOPSSUNSEZJV-COSPWPRJSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Glomus caledonium	Fungi	KNApSAcK
Momordica charantia	LOTUS Database	35616633

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
Coumaric acid or derivatives
Cinnamic acid or derivatives
Hydroxycinnamic acid or derivatives
Cinnamic acid ester
Methoxyphenol
Anisole
Styrene
Phenol ether
Phenoxy compound
Methoxybenzene
Phenol
Alkyl aryl ether
Fatty acid ester
1-hydroxy-2-unsubstituted benzenoid
Fatty acyl
Benzenoid
Monocyclic benzene moiety
Dicarboxylic acid or derivatives
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Carboxylic acid ester
Carboxylic acid derivative
Carboxylic acid
Ether
Organic oxygen compound
Carbonyl group
Hydrocarbon derivative
Organooxygen compound
Organic oxide
Aromatic homopolycyclic compound

Molecular Framework

Aromatic 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	8.23	ALOGPS
logP	8.76	ChemAxon
logS	-6.4	ALOGPS
pKa (Strongest Acidic)	4.59	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	93.06 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	182.49 m³·mol⁻¹	ChemAxon
Polarizability	73.02 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00054615

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

163184143

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for Bryoferulic acid (NP0084965)

MOL for NP0084965 (Bryoferulic acid)

3D MOL for NP0084965 (Bryoferulic acid)

3D SDF for NP0084965 (Bryoferulic acid)

3D-SDF for NP0084965 (Bryoferulic acid)

PDB for NP0084965 (Bryoferulic acid)

3D PDB for NP0084965 (Bryoferulic acid)

SMILES for NP0084965 (Bryoferulic acid)

INCHI for NP0084965 (Bryoferulic acid)

Structure for NP0084965 (Bryoferulic acid)

3D Structure for NP0084965 (Bryoferulic acid)