NP-MRD: Showing NP-Card for methyl 3-[(1r,2r,5s,6r,10r,13s,14s)-2-hydroxy-5,10,14-trimethyl-6-[(2s)-2-methyloxiran-2-yl]-3,8-dioxo-14-(3-oxopentyl)-15-oxatetracyclo[8.6.0.0¹,¹³.0⁴,⁹]hexadec-4(9)-en-5-yl]propanoate (NP0169247)

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Record Information

Version

2.0

Created at

2022-09-03 05:10:05 UTC

Updated at

2022-09-03 05:10:05 UTC

NP-MRD ID

NP0169247

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl 3-[(1r,2r,5s,6r,10r,13s,14s)-2-hydroxy-5,10,14-trimethyl-6-[(2s)-2-methyloxiran-2-yl]-3,8-dioxo-14-(3-oxopentyl)-15-oxatetracyclo[8.6.0.0¹,¹³.0⁴,⁹]hexadec-4(9)-en-5-yl]propanoate

Description

Ganoboninone D belongs to the class of organic compounds known as fatty acid esters. These are carboxylic ester derivatives of a fatty acid. methyl 3-[(1r,2r,5s,6r,10r,13s,14s)-2-hydroxy-5,10,14-trimethyl-6-[(2s)-2-methyloxiran-2-yl]-3,8-dioxo-14-(3-oxopentyl)-15-oxatetracyclo[8.6.0.0¹,¹³.0⁴,⁹]hexadec-4(9)-en-5-yl]propanoate is found in Ganoderma orbiforme. Based on a literature review very few articles have been published on Ganoboninone D.

Structure

MOL 3D MOL SDF PDB SMILES InChI

  Mrv1652309032207102D          

 38 42  0  0  1  0            999 V2000
   -4.0443   -0.4414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2870   -0.1140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6249   -0.6061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7200   -1.4256    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8676   -0.2787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2054   -0.7708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4482   -0.4434    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8530    0.2755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2017   -1.2307    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6232   -1.2396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8866   -0.4578    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2244    0.0343    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4878    0.8161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3128    0.8072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5592    0.0199    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1783    0.5653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3092   -0.3238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3866   -1.1451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7140   -1.6228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7914   -2.4442    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9640   -1.2792    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2913   -1.7568    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1366   -1.4888    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6679   -2.1677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7239   -2.0683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5157   -2.8666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1029   -3.4460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8983   -3.2272    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8947   -4.2443    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4819   -4.8238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8093   -1.0111    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.5593   -1.3548    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.3511   -2.1531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0280   -0.6758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3816   -1.4212    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7319   -0.1897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9819    0.1539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9045    0.9753    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  7  6  1  1  0  0  0
  7  8  1  6  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 11 10  1  1  0  0  0
 11 12  1  0  0  0  0
  7 12  1  0  0  0  0
 12 13  1  1  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 11 15  1  0  0  0  0
 15 16  1  6  0  0  0
 15 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
 11 21  1  0  0  0  0
 21 22  1  6  0  0  0
 18 23  1  0  0  0  0
 23 24  1  1  0  0  0
 23 25  1  6  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 27 29  1  0  0  0  0
 29 30  1  0  0  0  0
 23 31  1  0  0  0  0
 31 32  1  1  0  0  0
 32 33  1  6  0  0  0
 32 34  1  0  0  0  0
 34 35  1  0  0  0  0
 32 35  1  1  0  0  0
 31 36  1  0  0  0  0
 36 37  1  0  0  0  0
 17 37  1  0  0  0  0
 37 38  2  0  0  0  0
M  END

     RDKit          3D

 80 84  0  0  0  0  0  0  0  0999 V2000
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    4.3810   -0.7147   -0.7904 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.5633   -0.6834    1.5124 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1331   -1.3636   -0.2877 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9360   -0.7089   -0.3185 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1417    0.6971    0.1454 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5784    0.8519   -0.2322 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4305    0.8781   -1.7648 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0990    1.5215   -2.0370 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4751    1.7458   -0.7141 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8563    3.1350   -0.2588 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9791    1.6569   -0.6834 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5342    1.0158    0.3842 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7537    0.9460    1.6048 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.8994   -0.2622   -1.1516 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5857   -0.2062    1.2079 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0330   -1.5045    1.6889 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9568   -2.5890    0.6779 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8900   -2.8521    0.0729 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.6808    1.8561   -0.1030 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.1454    1.7248    0.1131 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.0253    0.8382   -0.6956 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7302    2.3690    1.3717 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7316    3.0851    0.2036 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3143    2.4587   -1.4248 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8521    2.2221   -1.6785 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4177    2.5450   -2.8168 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7983   -1.4919    0.4591 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6689   -1.8271   -0.9518 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4835   -0.3700    0.1199 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4727   -3.3102    1.0223 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8907   -1.9706    2.0253 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2101   -2.7666   -1.1916 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7790   -2.1110   -1.6206 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2506   -0.2989   -1.8275 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1865    0.0034   -0.3909 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6575   -0.7569    1.6724 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1037   -1.5491    2.0202 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3323    0.2727    2.1076 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4812   -0.7818   -1.3235 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2588   -1.2210    0.3928 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1167    1.6944    0.1617 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3044   -0.1756   -2.1561 H   0  0  0  0  0  0  0  0  0  0  0  0
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    0.4367    0.9389   -2.7069 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2967    2.4766   -2.5972 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9178    3.3092   -0.1279 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5297    3.8233   -1.0958 H   0  0  0  0  0  0  0  0  0  0  0  0
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    1.0005    0.0472    2.2458 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9424    2.1663    3.0306 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5487   -1.1358   -1.1457 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8789   -0.5757   -1.4262 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2585    0.3419   -2.0252 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6115   -0.4827    0.7833 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8920    0.4555    2.0710 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7356   -1.9423    2.4803 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0059   -1.4420    2.1392 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2907   -3.9192   -1.5676 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.9244   -5.0823   -0.3856 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -5.5387    0.1168   -1.3414 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7257    0.2831   -0.0355 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9570    2.6054    2.1284 H   0  0  0  0  0  0  0  0  0  0  0  0
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  1  2  1  0
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  3  4  2  0
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  7  6  1  6
  7  8  1  0
  7  9  1  0
  9 10  1  0
 11 10  1  6
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 23 24  1  6
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 29 30  1  0
 23 31  1  0
 31 36  1  0
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 37 38  2  0
 31 32  1  0
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 32 34  1  0
 34 35  1  0
 12  7  1  0
 37 17  1  0
 35 32  1  0
 15 11  1  0
 21 11  1  0
  1 39  1  0
  1 40  1  0
  1 41  1  0
  2 42  1  0
  2 43  1  0
  5 44  1  0
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  6 46  1  0
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  8 48  1  0
  8 49  1  0
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 16 59  1  0
 16 60  1  0
 21 61  1  1
 22 62  1  0
 24 63  1  0
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 25 66  1  0
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 30 70  1  0
 30 71  1  0
 30 72  1  0
 31 73  1  1
 36 79  1  0
 36 80  1  0
 33 74  1  0
 33 75  1  0
 33 76  1  0
 34 77  1  0
 34 78  1  0
M  END

  Mrv1652309032207102D          

 38 42  0  0  1  0            999 V2000
   -4.0443   -0.4414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2870   -0.1140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6249   -0.6061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7200   -1.4256    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8676   -0.2787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2054   -0.7708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4482   -0.4434    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8530    0.2755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2017   -1.2307    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6232   -1.2396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8866   -0.4578    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2244    0.0343    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4878    0.8161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3128    0.8072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5592    0.0199    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1783    0.5653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.2913   -1.7568    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1366   -1.4888    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6679   -2.1677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7239   -2.0683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5157   -2.8666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1029   -3.4460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8983   -3.2272    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8947   -4.2443    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4819   -4.8238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8093   -1.0111    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.5593   -1.3548    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.3511   -2.1531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0280   -0.6758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3816   -1.4212    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7319   -0.1897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9819    0.1539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9045    0.9753    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  7  6  1  1  0  0  0
  7  8  1  6  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 11 10  1  1  0  0  0
 11 12  1  0  0  0  0
  7 12  1  0  0  0  0
 12 13  1  1  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 11 15  1  0  0  0  0
 15 16  1  6  0  0  0
 15 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
 11 21  1  0  0  0  0
 21 22  1  6  0  0  0
 18 23  1  0  0  0  0
 23 24  1  1  0  0  0
 23 25  1  6  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 27 29  1  0  0  0  0
 29 30  1  0  0  0  0
 23 31  1  0  0  0  0
 31 32  1  1  0  0  0
 32 33  1  6  0  0  0
 32 34  1  0  0  0  0
 34 35  1  0  0  0  0
 32 35  1  1  0  0  0
 31 36  1  0  0  0  0
 36 37  1  0  0  0  0
 17 37  1  0  0  0  0
 37 38  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0169247

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCC(=O)CC[C@]1(C)OC[C@@]23[C@@H]1CC[C@@]2(C)C1=C(C(=O)[C@@H]3O)[C@@](C)(CCC(=O)OC)[C@@H](CC1=O)[C@@]1(C)CO1

> <INCHI_IDENTIFIER>
InChI=1S/C30H42O8/c1-7-17(31)8-13-28(4)19-9-12-27(3)22-18(32)14-20(29(5)15-37-29)26(2,11-10-21(33)36-6)23(22)24(34)25(35)30(19,27)16-38-28/h19-20,25,35H,7-16H2,1-6H3/t19-,20-,25+,26+,27+,28+,29-,30+/m1/s1

> <INCHI_KEY>
WHVXPOKOWPLVPS-CAYUPQFCSA-N

> <FORMULA>
C30H42O8

> <MOLECULAR_WEIGHT>
530.658

> <EXACT_MASS>
530.287968312

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
80

> <JCHEM_AVERAGE_POLARIZABILITY>
57.59901632363149

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl 3-[(1R,2R,5S,6R,10R,13S,14S)-2-hydroxy-5,10,14-trimethyl-6-[(2S)-2-methyloxiran-2-yl]-3,8-dioxo-14-(3-oxopentyl)-15-oxatetracyclo[8.6.0.0^{1,13}.0^{4,9}]hexadec-4(9)-en-5-yl]propanoate

> <ALOGPS_LOGP>
3.12

> <JCHEM_LOGP>
2.548358644333331

> <ALOGPS_LOGS>
-5.00

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
17.93680208954721

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.8331618552081

> <JCHEM_PKA_STRONGEST_BASIC>
-3.7464785244357275

> <JCHEM_POLAR_SURFACE_AREA>
119.50000000000001

> <JCHEM_REFRACTIVITY>
139.09859999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.29e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl 3-[(1R,2R,5S,6R,10R,13S,14S)-2-hydroxy-5,10,14-trimethyl-6-[(2S)-2-methyloxiran-2-yl]-3,8-dioxo-14-(3-oxopentyl)-15-oxatetracyclo[8.6.0.0^{1,13}.0^{4,9}]hexadec-4(9)-en-5-yl]propanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 03-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-SEP-22         0                                  
HETATM    1  C   UNK     0      -7.549  -0.824   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -6.136  -0.213   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.900  -1.131   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -5.077  -2.661   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      -3.486  -0.520   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.250  -1.439   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.837  -0.828   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.592   0.514   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -0.377  -2.297   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       1.163  -2.314   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.655  -0.855   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.419   0.064   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.911   1.523   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.451   1.507   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.911   0.037   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.066   1.055   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.311  -0.604   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.455  -2.138   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.199  -3.029   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       3.344  -4.562   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       1.799  -2.388   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       0.544  -3.279   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       5.855  -2.779   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       4.980  -4.046   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       6.951  -3.861   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       6.563  -5.351   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       7.659  -6.433   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       9.144  -6.024   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0       7.270  -7.923   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       8.366  -9.004   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       7.111  -1.887   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       8.511  -2.529   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       8.122  -4.019   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       9.386  -1.262   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      10.046  -2.653   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0       6.966  -0.354   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       5.566   0.287   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0       5.422   1.821   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9   12                                             
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   15   21                                             
CONECT   12   11    7   13                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   11   16   17                                             
CONECT   16   15                                                            
CONECT   17   15   18   37                                                  
CONECT   18   17   19   23                                                  
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   11   22                                                  
CONECT   22   21                                                            
CONECT   23   18   24   25   31                                             
CONECT   24   23                                                            
CONECT   25   23   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30                                                       
CONECT   30   29                                                            
CONECT   31   23   32   36                                                  
CONECT   32   31   33   34   35                                             
CONECT   33   32                                                            
CONECT   34   32   35                                                       
CONECT   35   34   32                                                       
CONECT   36   31   37                                                       
CONECT   37   36   17   38                                                  
CONECT   38   37                                                            
MASTER        0    0    0    0    0    0    0    0   38    0   84    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₀H₄₂O₈

Average Mass

530.6580 Da

Monoisotopic Mass

530.28797 Da

IUPAC Name

methyl 3-[(1R,2R,5S,6R,10R,13S,14S)-2-hydroxy-5,10,14-trimethyl-6-[(2S)-2-methyloxiran-2-yl]-3,8-dioxo-14-(3-oxopentyl)-15-oxatetracyclo[8.6.0.0^{1,13}.0^{4,9}]hexadec-4(9)-en-5-yl]propanoate

Traditional Name

methyl 3-[(1R,2R,5S,6R,10R,13S,14S)-2-hydroxy-5,10,14-trimethyl-6-[(2S)-2-methyloxiran-2-yl]-3,8-dioxo-14-(3-oxopentyl)-15-oxatetracyclo[8.6.0.0^{1,13}.0^{4,9}]hexadec-4(9)-en-5-yl]propanoate

CAS Registry Number

Not Available

SMILES

CCC(=O)CC[C@]1(C)OC[C@@]23[C@@H]1CC[C@@]2(C)C1=C(C(=O)[C@@H]3O)[C@@](C)(CCC(=O)OC)[C@@H](CC1=O)[C@@]1(C)CO1

InChI Identifier

InChI=1S/C30H42O8/c1-7-17(31)8-13-28(4)19-9-12-27(3)22-18(32)14-20(29(5)15-37-29)26(2,11-10-21(33)36-6)23(22)24(34)25(35)30(19,27)16-38-28/h19-20,25,35H,7-16H2,1-6H3/t19-,20-,25+,26+,27+,28+,29-,30+/m1/s1

InChI Key

WHVXPOKOWPLVPS-CAYUPQFCSA-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
Ganoderma orbiforme	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as fatty acid esters. These are carboxylic ester derivatives of a fatty acid.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acid esters

Direct Parent

Fatty acid esters

Alternative Parents

Substituents

Cyclohexenone
Fatty acid ester
Methyl ester
Tetrahydrofuran
Secondary alcohol
Ketone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Ether
Oxirane
Dialkyl ether
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic 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	3.12	ALOGPS
logP	2.55	ChemAxon
logS	-5	ALOGPS
pKa (Strongest Acidic)	12.83	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	119.5 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	139.1 m³·mol⁻¹	ChemAxon
Polarizability	57.6 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	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

Not Available

Chemspider ID

78438354

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

122370817

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for methyl 3-[(1r,2r,5s,6r,10r,13s,14s)-2-hydroxy-5,10,14-trimethyl-6-[(2s)-2-methyloxiran-2-yl]-3,8-dioxo-14-(3-oxopentyl)-15-oxatetracyclo[8.6.0.0¹,¹³.0⁴,⁹]hexadec-4(9)-en-5-yl]propanoate (NP0169247)

MOL for NP0169247 (methyl 3-[(1r,2r,5s,6r,10r,13s,14s)-2-hydroxy-5,10,14-trimethyl-6-[(2s)-2-methyloxiran-2-yl]-3,8-dioxo-14-(3-oxopentyl)-15-oxatetracyclo[8.6.0.0¹,¹³.0⁴,⁹]hexadec-4(9)-en-5-yl]propanoate)

3D MOL for NP0169247 (methyl 3-[(1r,2r,5s,6r,10r,13s,14s)-2-hydroxy-5,10,14-trimethyl-6-[(2s)-2-methyloxiran-2-yl]-3,8-dioxo-14-(3-oxopentyl)-15-oxatetracyclo[8.6.0.0¹,¹³.0⁴,⁹]hexadec-4(9)-en-5-yl]propanoate)

3D SDF for NP0169247 (methyl 3-[(1r,2r,5s,6r,10r,13s,14s)-2-hydroxy-5,10,14-trimethyl-6-[(2s)-2-methyloxiran-2-yl]-3,8-dioxo-14-(3-oxopentyl)-15-oxatetracyclo[8.6.0.0¹,¹³.0⁴,⁹]hexadec-4(9)-en-5-yl]propanoate)

3D-SDF for NP0169247 (methyl 3-[(1r,2r,5s,6r,10r,13s,14s)-2-hydroxy-5,10,14-trimethyl-6-[(2s)-2-methyloxiran-2-yl]-3,8-dioxo-14-(3-oxopentyl)-15-oxatetracyclo[8.6.0.0¹,¹³.0⁴,⁹]hexadec-4(9)-en-5-yl]propanoate)

PDB for NP0169247 (methyl 3-[(1r,2r,5s,6r,10r,13s,14s)-2-hydroxy-5,10,14-trimethyl-6-[(2s)-2-methyloxiran-2-yl]-3,8-dioxo-14-(3-oxopentyl)-15-oxatetracyclo[8.6.0.0¹,¹³.0⁴,⁹]hexadec-4(9)-en-5-yl]propanoate)

3D PDB for NP0169247 (methyl 3-[(1r,2r,5s,6r,10r,13s,14s)-2-hydroxy-5,10,14-trimethyl-6-[(2s)-2-methyloxiran-2-yl]-3,8-dioxo-14-(3-oxopentyl)-15-oxatetracyclo[8.6.0.0¹,¹³.0⁴,⁹]hexadec-4(9)-en-5-yl]propanoate)

SMILES for NP0169247 (methyl 3-[(1r,2r,5s,6r,10r,13s,14s)-2-hydroxy-5,10,14-trimethyl-6-[(2s)-2-methyloxiran-2-yl]-3,8-dioxo-14-(3-oxopentyl)-15-oxatetracyclo[8.6.0.0¹,¹³.0⁴,⁹]hexadec-4(9)-en-5-yl]propanoate)

INCHI for NP0169247 (methyl 3-[(1r,2r,5s,6r,10r,13s,14s)-2-hydroxy-5,10,14-trimethyl-6-[(2s)-2-methyloxiran-2-yl]-3,8-dioxo-14-(3-oxopentyl)-15-oxatetracyclo[8.6.0.0¹,¹³.0⁴,⁹]hexadec-4(9)-en-5-yl]propanoate)

Structure for NP0169247 (methyl 3-[(1r,2r,5s,6r,10r,13s,14s)-2-hydroxy-5,10,14-trimethyl-6-[(2s)-2-methyloxiran-2-yl]-3,8-dioxo-14-(3-oxopentyl)-15-oxatetracyclo[8.6.0.0¹,¹³.0⁴,⁹]hexadec-4(9)-en-5-yl]propanoate)

3D Structure for NP0169247 (methyl 3-[(1r,2r,5s,6r,10r,13s,14s)-2-hydroxy-5,10,14-trimethyl-6-[(2s)-2-methyloxiran-2-yl]-3,8-dioxo-14-(3-oxopentyl)-15-oxatetracyclo[8.6.0.0¹,¹³.0⁴,⁹]hexadec-4(9)-en-5-yl]propanoate)