NP-MRD: Showing NP-Card for virgaurin C (NP0041806)

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Record Information

Version

2.0

Created at

2021-06-20 23:37:41 UTC

Updated at

2021-06-30 00:16:32 UTC

NP-MRD ID

NP0041806

Secondary Accession Numbers

None

Natural Product Identification

Common Name

virgaurin C

Provided By

JEOL Database JEOL Logo

Description

(4AS,5S)-3-[(2S,5R,6R,7R)-6-hydroxy-2,7,13,15-tetramethyl-8,11-dioxatetracyclo[7.6.1.0⁵,¹⁶.0¹⁰,¹⁴]Hexadeca-1(15),9(16),10(14),12-tetraen-7-yl]-4a,5-dimethyl-2,4a,5,6,7,8-hexahydronaphthalen-2-one belongs to the class of organic compounds known as eremophilane, 8,9-secoeremophilane and furoeremophilane sesquiterpenoids. These are sesquiterpenoids with a structure based either on the eremophilane skeleton, its 8,9-seco derivative, or the furoeremophilane skeleton. Eremophilanes have been shown to be derived from eudesmanes by migration of the methyl group at C-10 to C-5. virgaurin C is found in Ligularia virgaurea. virgaurin C was first documented in 2012 (Saito, Y., et al.). Based on a literature review very few articles have been published on (4aS,5S)-3-[(2S,5R,6R,7R)-6-hydroxy-2,7,13,15-tetramethyl-8,11-dioxatetracyclo[7.6.1.0⁵,¹⁶.0¹⁰,¹⁴]Hexadeca-1(15),9(16),10(14),12-tetraen-7-yl]-4a,5-dimethyl-2,4a,5,6,7,8-hexahydronaphthalen-2-one.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306212101373D          

 70 75  0  0  0  0            999 V2000
    1.6254    2.1818   -5.7430 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1027    1.3082   -4.6647 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1021    0.3704   -4.8127 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1599   -0.2482   -3.6410 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6771    0.2854   -2.7060 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7091   -0.0963   -1.3659 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6230    0.5713   -0.5374 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4580    1.6037   -1.0538 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4416    1.9222   -2.4555 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3521    2.9706   -3.0438 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4951    1.2502   -3.2793 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3152    2.4301   -0.0842 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6935    3.8211    0.1246 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5443    1.7537    1.2770 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2481    1.1970    1.8433 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7345    0.1082    0.9019 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4095   -0.5005    1.3851 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5529    0.5595    1.5478 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0707   -1.5933    0.3801 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9088   -2.7844    0.2780 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4667   -2.1281    0.7563 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5594   -2.0358   -0.0304 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9562   -2.5600    0.2690 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.2462   -3.6469   -0.7906 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0191   -3.1872    1.6599 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9515   -3.2959    2.4659 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6157   -2.7971    2.0800 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6812   -2.9222    2.8631 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3806   -3.6367    2.1300 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.3647   -2.4740    2.0789 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.3999   -1.8185    0.7009 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.9963   -1.3841    0.2209 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.1413   -0.7103   -1.1525 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.6434    1.8871   -6.0159 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6312    3.2295   -5.4273 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4985    0.0473   -5.6517 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6802    2.6761   -4.0444 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8258    3.9270   -3.1141 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2721    3.1115   -2.4744 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3164    2.5574   -0.5099 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6605    4.3969   -0.8046 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6656    3.7566    0.4975 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2790    4.4054    0.8427 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2673    0.9356    1.1583 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9922    2.4588    1.9873 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5140    1.9993    1.9757 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4355    0.7703    2.8359 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4923   -0.6881    0.9026 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5731   -0.9234    2.3817 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3842    0.1638    1.8580 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1987   -3.1746    1.2578 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4640   -3.6052   -0.2986 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8254   -2.5161   -0.2587 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4448   -1.5653   -1.0067 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5757   -4.5075   -0.6692 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0996   -3.2718   -1.8103 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2709   -4.0268   -0.7322 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0114   -3.7336    3.4565 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3417   -4.0244    3.1553 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7365   -4.4622    1.5033 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0870   -1.7229    2.8296 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3677   -2.8286    2.3426 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8511   -2.5107   -0.0204 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0617   -0.9445    0.7452 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6499   -0.6036    0.9160 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5157   -1.4066   -1.9092 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8524    0.1218   -1.0943 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1946   -0.2924   -1.5050 H   0  0  0  0  0  0  0  0  0  0  0  0
  7  8  2  0  0  0  0
 25 26  2  0  0  0  0
 23 32  1  0  0  0  0
  8  9  1  0  0  0  0
  9 11  2  0  0  0  0
  5  6  2  0  0  0  0
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 25 29  1  0  0  0  0
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 23 25  1  0  0  0  0
 11  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
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  2  1  1  0  0  0  0
 12 13  1  0  0  0  0
 26 27  1  0  0  0  0
 16  7  1  0  0  0  0
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 27 21  1  0  0  0  0
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 15 14  1  0  0  0  0
 22 23  1  0  0  0  0
 16 17  1  0  0  0  0
  7  6  1  0  0  0  0
  6 34  1  0  0  0  0
 34 19  1  0  0  0  0
 19 17  1  0  0  0  0
 22 21  2  0  0  0  0
 17 18  1  0  0  0  0
 16 50  1  6  0  0  0
 15 16  1  0  0  0  0
 19 20  1  6  0  0  0
 14 12  1  0  0  0  0
 23 24  1  6  0  0  0
 12  8  1  0  0  0  0
  9 10  1  0  0  0  0
 26 60  1  0  0  0  0
 22 56  1  0  0  0  0
 29 61  1  0  0  0  0
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 30 63  1  0  0  0  0
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 31 65  1  0  0  0  0
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 32 67  1  1  0  0  0
 33 68  1  0  0  0  0
 33 69  1  0  0  0  0
 33 70  1  0  0  0  0
 15 48  1  0  0  0  0
 15 49  1  0  0  0  0
 14 46  1  0  0  0  0
 14 47  1  0  0  0  0
 12 42  1  6  0  0  0
  3 38  1  0  0  0  0
  1 35  1  0  0  0  0
  1 36  1  0  0  0  0
  1 37  1  0  0  0  0
 13 43  1  0  0  0  0
 13 44  1  0  0  0  0
 13 45  1  0  0  0  0
 17 51  1  1  0  0  0
 18 52  1  0  0  0  0
 20 53  1  0  0  0  0
 20 54  1  0  0  0  0
 20 55  1  0  0  0  0
 24 57  1  0  0  0  0
 24 58  1  0  0  0  0
 24 59  1  0  0  0  0
 10 39  1  0  0  0  0
 10 40  1  0  0  0  0
 10 41  1  0  0  0  0
M  END

     RDKit          3D

 70 75  0  0  0  0  0  0  0  0999 V2000
    1.6254    2.1818   -5.7430 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1027    1.3082   -4.6647 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1021    0.3704   -4.8127 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1599   -0.2482   -3.6410 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6771    0.2854   -2.7060 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7091   -0.0963   -1.3659 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6230    0.5713   -0.5374 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4580    1.6037   -1.0538 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4416    1.9222   -2.4555 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3521    2.9706   -3.0438 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4951    1.2502   -3.2793 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3152    2.4301   -0.0842 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6935    3.8211    0.1246 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5443    1.7537    1.2770 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2481    1.1970    1.8433 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7345    0.1082    0.9019 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4095   -0.5005    1.3851 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5529    0.5595    1.5478 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0707   -1.5933    0.3801 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9088   -2.7844    0.2780 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4667   -2.1281    0.7563 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5594   -2.0358   -0.0304 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.2462   -3.6469   -0.7906 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0191   -3.1872    1.6599 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9515   -3.2959    2.4659 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.1673   -1.0584   -0.9598 O   0  0  0  0  0  0  0  0  0  0  0  0
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    4.3164    2.5574   -0.5099 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6605    4.3969   -0.8046 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6656    3.7566    0.4975 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2790    4.4054    0.8427 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2673    0.9356    1.1583 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9922    2.4588    1.9873 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5140    1.9993    1.9757 H   0  0  0  0  0  0  0  0  0  0  0  0
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    2.4923   -0.6881    0.9026 H   0  0  0  0  0  0  0  0  0  0  0  0
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  7  8  2  0
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 29 61  1  0
 29 62  1  0
 30 63  1  0
 30 64  1  0
 31 65  1  0
 31 66  1  0
 32 67  1  1
 33 68  1  0
 33 69  1  0
 33 70  1  0
 15 48  1  0
 15 49  1  0
 14 46  1  0
 14 47  1  0
 12 42  1  6
  3 38  1  0
  1 35  1  0
  1 36  1  0
  1 37  1  0
 13 43  1  0
 13 44  1  0
 13 45  1  0
 17 51  1  1
 18 52  1  0
 20 53  1  0
 20 54  1  0
 20 55  1  0
 24 57  1  0
 24 58  1  0
 24 59  1  0
 10 39  1  0
 10 40  1  0
 10 41  1  0
M  END


  Mrv1652306212101373D          

 70 75  0  0  0  0            999 V2000
    1.6254    2.1818   -5.7430 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1027    1.3082   -4.6647 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1021    0.3704   -4.8127 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1599   -0.2482   -3.6410 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6771    0.2854   -2.7060 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7091   -0.0963   -1.3659 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6230    0.5713   -0.5374 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4580    1.6037   -1.0538 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4416    1.9222   -2.4555 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3521    2.9706   -3.0438 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4951    1.2502   -3.2793 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3152    2.4301   -0.0842 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6935    3.8211    0.1246 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5443    1.7537    1.2770 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2481    1.1970    1.8433 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7345    0.1082    0.9019 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4095   -0.5005    1.3851 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5529    0.5595    1.5478 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0707   -1.5933    0.3801 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9088   -2.7844    0.2780 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4667   -2.1281    0.7563 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5594   -2.0358   -0.0304 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9562   -2.5600    0.2690 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.2462   -3.6469   -0.7906 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0191   -3.1872    1.6599 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9515   -3.2959    2.4659 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6157   -2.7971    2.0800 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6812   -2.9222    2.8631 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3806   -3.6367    2.1300 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.3647   -2.4740    2.0789 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.3999   -1.8185    0.7009 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.9963   -1.3841    0.2209 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.1413   -0.7103   -1.1525 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1673   -1.0584   -0.9598 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0058    2.1128   -6.6435 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6434    1.8871   -6.0159 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6312    3.2295   -5.4273 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4985    0.0473   -5.6517 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6802    2.6761   -4.0444 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8258    3.9270   -3.1141 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2721    3.1115   -2.4744 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3164    2.5574   -0.5099 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6605    4.3969   -0.8046 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6656    3.7566    0.4975 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2790    4.4054    0.8427 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2673    0.9356    1.1583 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9922    2.4588    1.9873 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5140    1.9993    1.9757 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4355    0.7703    2.8359 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4923   -0.6881    0.9026 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5731   -0.9234    2.3817 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3842    0.1638    1.8580 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1987   -3.1746    1.2578 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4640   -3.6052   -0.2986 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8254   -2.5161   -0.2587 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4448   -1.5653   -1.0067 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5757   -4.5075   -0.6692 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0996   -3.2718   -1.8103 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2709   -4.0268   -0.7322 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0114   -3.7336    3.4565 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3417   -4.0244    3.1553 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7365   -4.4622    1.5033 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0870   -1.7229    2.8296 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3677   -2.8286    2.3426 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8511   -2.5107   -0.0204 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0617   -0.9445    0.7452 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6499   -0.6036    0.9160 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5157   -1.4066   -1.9092 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8524    0.1218   -1.0943 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1946   -0.2924   -1.5050 H   0  0  0  0  0  0  0  0  0  0  0  0
  7  8  2  0  0  0  0
 25 26  2  0  0  0  0
 23 32  1  0  0  0  0
  8  9  1  0  0  0  0
  9 11  2  0  0  0  0
  5  6  2  0  0  0  0
  5 11  1  0  0  0  0
 25 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 23 25  1  0  0  0  0
 11  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
 32 33  1  0  0  0  0
  2  1  1  0  0  0  0
 12 13  1  0  0  0  0
 26 27  1  0  0  0  0
 16  7  1  0  0  0  0
 27 28  2  0  0  0  0
 27 21  1  0  0  0  0
 21 19  1  0  0  0  0
 15 14  1  0  0  0  0
 22 23  1  0  0  0  0
 16 17  1  0  0  0  0
  7  6  1  0  0  0  0
  6 34  1  0  0  0  0
 34 19  1  0  0  0  0
 19 17  1  0  0  0  0
 22 21  2  0  0  0  0
 17 18  1  0  0  0  0
 16 50  1  6  0  0  0
 15 16  1  0  0  0  0
 19 20  1  6  0  0  0
 14 12  1  0  0  0  0
 23 24  1  6  0  0  0
 12  8  1  0  0  0  0
  9 10  1  0  0  0  0
 26 60  1  0  0  0  0
 22 56  1  0  0  0  0
 29 61  1  0  0  0  0
 29 62  1  0  0  0  0
 30 63  1  0  0  0  0
 30 64  1  0  0  0  0
 31 65  1  0  0  0  0
 31 66  1  0  0  0  0
 32 67  1  1  0  0  0
 33 68  1  0  0  0  0
 33 69  1  0  0  0  0
 33 70  1  0  0  0  0
 15 48  1  0  0  0  0
 15 49  1  0  0  0  0
 14 46  1  0  0  0  0
 14 47  1  0  0  0  0
 12 42  1  6  0  0  0
  3 38  1  0  0  0  0
  1 35  1  0  0  0  0
  1 36  1  0  0  0  0
  1 37  1  0  0  0  0
 13 43  1  0  0  0  0
 13 44  1  0  0  0  0
 13 45  1  0  0  0  0
 17 51  1  1  0  0  0
 18 52  1  0  0  0  0
 20 53  1  0  0  0  0
 20 54  1  0  0  0  0
 20 55  1  0  0  0  0
 24 57  1  0  0  0  0
 24 58  1  0  0  0  0
 24 59  1  0  0  0  0
 10 39  1  0  0  0  0
 10 40  1  0  0  0  0
 10 41  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0041806

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]O[C@]1([H])[C@@]2([H])C3=C(C(=C4C(OC([H])=C4C([H])([H])[H])=C3O[C@@]1(C1=C([H])[C@]3(C(=C([H])C1=O)C([H])([H])C([H])([H])C([H])([H])[C@]3([H])C([H])([H])[H])C([H])([H])[H])C([H])([H])[H])C([H])([H])[H])[C@@]([H])(C([H])([H])[H])C([H])([H])C2([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C30H36O4/c1-15-10-11-20-25-23(15)18(4)24-16(2)14-33-26(24)27(25)34-30(6,28(20)32)21-13-29(5)17(3)8-7-9-19(29)12-22(21)31/h12-15,17,20,28,32H,7-11H2,1-6H3/t15-,17-,20+,28+,29+,30+/m0/s1

> <INCHI_KEY>
PXLCJVXPHFFDDN-QYICRBEBSA-N

> <FORMULA>
C30H36O4

> <MOLECULAR_WEIGHT>
460.614

> <EXACT_MASS>
460.261359639

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
70

> <JCHEM_AVERAGE_POLARIZABILITY>
53.48479945474839

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(4aS,5S)-3-[(2S,5R,6R,7R)-6-hydroxy-2,7,13,15-tetramethyl-8,11-dioxatetracyclo[7.6.1.0^{5,16}.0^{10,14}]hexadeca-1(16),9,12,14-tetraen-7-yl]-4a,5-dimethyl-2,4a,5,6,7,8-hexahydronaphthalen-2-one

> <ALOGPS_LOGP>
6.26

> <JCHEM_LOGP>
6.557749763666665

> <ALOGPS_LOGS>
-5.11

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
19.042288285109297

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.496001350801716

> <JCHEM_PKA_STRONGEST_BASIC>
-2.794657762641787

> <JCHEM_POLAR_SURFACE_AREA>
59.67

> <JCHEM_REFRACTIVITY>
135.44399999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.56e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(4aS,5S)-3-[(2S,5R,6R,7R)-6-hydroxy-2,7,13,15-tetramethyl-8,11-dioxatetracyclo[7.6.1.0^{5,16}.0^{10,14}]hexadeca-1(16),9,12,14-tetraen-7-yl]-4a,5-dimethyl-5,6,7,8-tetrahydronaphthalen-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 70 75  0  0  0  0  0  0  0  0999 V2000
    1.6254    2.1818   -5.7430 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1027    1.3082   -4.6647 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1021    0.3704   -4.8127 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1599   -0.2482   -3.6410 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6771    0.2854   -2.7060 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7091   -0.0963   -1.3659 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6230    0.5713   -0.5374 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4580    1.6037   -1.0538 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4416    1.9222   -2.4555 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3521    2.9706   -3.0438 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4951    1.2502   -3.2793 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3152    2.4301   -0.0842 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6935    3.8211    0.1246 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5443    1.7537    1.2770 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2481    1.1970    1.8433 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7345    0.1082    0.9019 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4095   -0.5005    1.3851 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5529    0.5595    1.5478 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0707   -1.5933    0.3801 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9088   -2.7844    0.2780 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4667   -2.1281    0.7563 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5594   -2.0358   -0.0304 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9562   -2.5600    0.2690 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.2462   -3.6469   -0.7906 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0191   -3.1872    1.6599 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9515   -3.2959    2.4659 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6157   -2.7971    2.0800 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6812   -2.9222    2.8631 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3806   -3.6367    2.1300 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3647   -2.4740    2.0789 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3999   -1.8185    0.7009 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9963   -1.3841    0.2209 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.1413   -0.7103   -1.1525 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1673   -1.0584   -0.9598 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0058    2.1128   -6.6435 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6434    1.8871   -6.0159 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6312    3.2295   -5.4273 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4985    0.0473   -5.6517 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6802    2.6761   -4.0444 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8258    3.9270   -3.1141 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2721    3.1115   -2.4744 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3164    2.5574   -0.5099 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6605    4.3969   -0.8046 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6656    3.7566    0.4975 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2790    4.4054    0.8427 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2673    0.9356    1.1583 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9922    2.4588    1.9873 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5140    1.9993    1.9757 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4355    0.7703    2.8359 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4923   -0.6881    0.9026 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5731   -0.9234    2.3817 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3842    0.1638    1.8580 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1987   -3.1746    1.2578 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4640   -3.6052   -0.2986 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8254   -2.5161   -0.2587 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4448   -1.5653   -1.0067 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5757   -4.5075   -0.6692 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0996   -3.2718   -1.8103 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2709   -4.0268   -0.7322 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0114   -3.7336    3.4565 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3417   -4.0244    3.1553 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7365   -4.4622    1.5033 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0870   -1.7229    2.8296 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3677   -2.8286    2.3426 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8511   -2.5107   -0.0204 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0617   -0.9445    0.7452 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6499   -0.6036    0.9160 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5157   -1.4066   -1.9092 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8524    0.1218   -1.0943 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1946   -0.2924   -1.5050 H   0  0  0  0  0  0  0  0  0  0  0  0
  7  8  2  0
 25 26  2  0
 23 32  1  0
  8  9  1  0
  9 11  2  0
  5  6  2  0
  5 11  1  0
 25 29  1  0
 29 30  1  0
 30 31  1  0
 31 32  1  0
 23 25  1  0
 11  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
 32 33  1  0
  2  1  1  0
 12 13  1  0
 26 27  1  0
 16  7  1  0
 27 28  2  0
 27 21  1  0
 21 19  1  0
 15 14  1  0
 22 23  1  0
 16 17  1  0
  7  6  1  0
  6 34  1  0
 34 19  1  0
 19 17  1  0
 22 21  2  0
 17 18  1  0
 16 50  1  6
 15 16  1  0
 19 20  1  6
 14 12  1  0
 23 24  1  6
 12  8  1  0
  9 10  1  0
 26 60  1  0
 22 56  1  0
 29 61  1  0
 29 62  1  0
 30 63  1  0
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 31 65  1  0
 31 66  1  0
 32 67  1  1
 33 68  1  0
 33 69  1  0
 33 70  1  0
 15 48  1  0
 15 49  1  0
 14 46  1  0
 14 47  1  0
 12 42  1  6
  3 38  1  0
  1 35  1  0
  1 36  1  0
  1 37  1  0
 13 43  1  0
 13 44  1  0
 13 45  1  0
 17 51  1  1
 18 52  1  0
 20 53  1  0
 20 54  1  0
 20 55  1  0
 24 57  1  0
 24 58  1  0
 24 59  1  0
 10 39  1  0
 10 40  1  0
 10 41  1  0
M  END

HEADER    PROTEIN                                 21-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   21-JUN-21         0                                  
HETATM    1  C   UNK     0       1.625   2.182  -5.743  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.103   1.308  -4.665  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.102   0.370  -4.813  0.00  0.00           C+0
HETATM    4  O   UNK     0      -0.160  -0.248  -3.641  0.00  0.00           O+0
HETATM    5  C   UNK     0       0.677   0.285  -2.706  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.709  -0.096  -1.366  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.623   0.571  -0.537  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.458   1.604  -1.054  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.442   1.922  -2.455  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.352   2.971  -3.044  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.495   1.250  -3.279  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.315   2.430  -0.084  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.693   3.821   0.125  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.544   1.754   1.277  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.248   1.197   1.843  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.734   0.108   0.902  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.410  -0.500   1.385  0.00  0.00           C+0
HETATM   18  O   UNK     0      -0.553   0.560   1.548  0.00  0.00           O+0
HETATM   19  C   UNK     0      -0.071  -1.593   0.380  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.909  -2.784   0.278  0.00  0.00           C+0
HETATM   21  C   UNK     0      -1.467  -2.128   0.756  0.00  0.00           C+0
HETATM   22  C   UNK     0      -2.559  -2.036  -0.030  0.00  0.00           C+0
HETATM   23  C   UNK     0      -3.956  -2.560   0.269  0.00  0.00           C+0
HETATM   24  C   UNK     0      -4.246  -3.647  -0.791  0.00  0.00           C+0
HETATM   25  C   UNK     0      -4.019  -3.187   1.660  0.00  0.00           C+0
HETATM   26  C   UNK     0      -2.951  -3.296   2.466  0.00  0.00           C+0
HETATM   27  C   UNK     0      -1.616  -2.797   2.080  0.00  0.00           C+0
HETATM   28  O   UNK     0      -0.681  -2.922   2.863  0.00  0.00           O+0
HETATM   29  C   UNK     0      -5.381  -3.637   2.130  0.00  0.00           C+0
HETATM   30  C   UNK     0      -6.365  -2.474   2.079  0.00  0.00           C+0
HETATM   31  C   UNK     0      -6.400  -1.819   0.701  0.00  0.00           C+0
HETATM   32  C   UNK     0      -4.996  -1.384   0.221  0.00  0.00           C+0
HETATM   33  C   UNK     0      -5.141  -0.710  -1.153  0.00  0.00           C+0
HETATM   34  O   UNK     0      -0.167  -1.058  -0.960  0.00  0.00           O+0
HETATM   35  H   UNK     0       1.006   2.113  -6.644  0.00  0.00           H+0
HETATM   36  H   UNK     0       2.643   1.887  -6.016  0.00  0.00           H+0
HETATM   37  H   UNK     0       1.631   3.229  -5.427  0.00  0.00           H+0
HETATM   38  H   UNK     0      -0.499   0.047  -5.652  0.00  0.00           H+0
HETATM   39  H   UNK     0       3.680   2.676  -4.044  0.00  0.00           H+0
HETATM   40  H   UNK     0       2.826   3.927  -3.114  0.00  0.00           H+0
HETATM   41  H   UNK     0       4.272   3.111  -2.474  0.00  0.00           H+0
HETATM   42  H   UNK     0       4.316   2.557  -0.510  0.00  0.00           H+0
HETATM   43  H   UNK     0       2.660   4.397  -0.805  0.00  0.00           H+0
HETATM   44  H   UNK     0       1.666   3.757   0.498  0.00  0.00           H+0
HETATM   45  H   UNK     0       3.279   4.405   0.843  0.00  0.00           H+0
HETATM   46  H   UNK     0       4.267   0.936   1.158  0.00  0.00           H+0
HETATM   47  H   UNK     0       3.992   2.459   1.987  0.00  0.00           H+0
HETATM   48  H   UNK     0       1.514   1.999   1.976  0.00  0.00           H+0
HETATM   49  H   UNK     0       2.436   0.770   2.836  0.00  0.00           H+0
HETATM   50  H   UNK     0       2.492  -0.688   0.903  0.00  0.00           H+0
HETATM   51  H   UNK     0       0.573  -0.923   2.382  0.00  0.00           H+0
HETATM   52  H   UNK     0      -1.384   0.164   1.858  0.00  0.00           H+0
HETATM   53  H   UNK     0       1.199  -3.175   1.258  0.00  0.00           H+0
HETATM   54  H   UNK     0       0.464  -3.605  -0.299  0.00  0.00           H+0
HETATM   55  H   UNK     0       1.825  -2.516  -0.259  0.00  0.00           H+0
HETATM   56  H   UNK     0      -2.445  -1.565  -1.007  0.00  0.00           H+0
HETATM   57  H   UNK     0      -3.576  -4.508  -0.669  0.00  0.00           H+0
HETATM   58  H   UNK     0      -4.100  -3.272  -1.810  0.00  0.00           H+0
HETATM   59  H   UNK     0      -5.271  -4.027  -0.732  0.00  0.00           H+0
HETATM   60  H   UNK     0      -3.011  -3.734   3.457  0.00  0.00           H+0
HETATM   61  H   UNK     0      -5.342  -4.024   3.155  0.00  0.00           H+0
HETATM   62  H   UNK     0      -5.737  -4.462   1.503  0.00  0.00           H+0
HETATM   63  H   UNK     0      -6.087  -1.723   2.830  0.00  0.00           H+0
HETATM   64  H   UNK     0      -7.368  -2.829   2.343  0.00  0.00           H+0
HETATM   65  H   UNK     0      -6.851  -2.511  -0.020  0.00  0.00           H+0
HETATM   66  H   UNK     0      -7.062  -0.945   0.745  0.00  0.00           H+0
HETATM   67  H   UNK     0      -4.650  -0.604   0.916  0.00  0.00           H+0
HETATM   68  H   UNK     0      -5.516  -1.407  -1.909  0.00  0.00           H+0
HETATM   69  H   UNK     0      -5.852   0.122  -1.094  0.00  0.00           H+0
HETATM   70  H   UNK     0      -4.195  -0.292  -1.505  0.00  0.00           H+0
CONECT    1    2   35   36   37                                             
CONECT    2   11    3    1                                                  
CONECT    3    2    4   38                                                  
CONECT    4    3    5                                                       
CONECT    5    6   11    4                                                  
CONECT    6    5    7   34                                                  
CONECT    7    8   16    6                                                  
CONECT    8    7    9   12                                                  
CONECT    9    8   11   10                                                  
CONECT   10    9   39   40   41                                             
CONECT   11    9    5    2                                                  
CONECT   12   13   14    8   42                                             
CONECT   13   12   43   44   45                                             
CONECT   14   15   12   46   47                                             
CONECT   15   14   16   48   49                                             
CONECT   16    7   17   50   15                                             
CONECT   17   16   19   18   51                                             
CONECT   18   17   52                                                       
CONECT   19   21   34   17   20                                             
CONECT   20   19   53   54   55                                             
CONECT   21   27   19   22                                                  
CONECT   22   23   21   56                                                  
CONECT   23   32   25   22   24                                             
CONECT   24   23   57   58   59                                             
CONECT   25   26   29   23                                                  
CONECT   26   25   27   60                                                  
CONECT   27   26   28   21                                                  
CONECT   28   27                                                            
CONECT   29   25   30   61   62                                             
CONECT   30   29   31   63   64                                             
CONECT   31   30   32   65   66                                             
CONECT   32   23   31   33   67                                             
CONECT   33   32   68   69   70                                             
CONECT   34    6   19                                                       
CONECT   35    1                                                            
CONECT   36    1                                                            
CONECT   37    1                                                            
CONECT   38    3                                                            
CONECT   39   10                                                            
CONECT   40   10                                                            
CONECT   41   10                                                            
CONECT   42   12                                                            
CONECT   43   13                                                            
CONECT   44   13                                                            
CONECT   45   13                                                            
CONECT   46   14                                                            
CONECT   47   14                                                            
CONECT   48   15                                                            
CONECT   49   15                                                            
CONECT   50   16                                                            
CONECT   51   17                                                            
CONECT   52   18                                                            
CONECT   53   20                                                            
CONECT   54   20                                                            
CONECT   55   20                                                            
CONECT   56   22                                                            
CONECT   57   24                                                            
CONECT   58   24                                                            
CONECT   59   24                                                            
CONECT   60   26                                                            
CONECT   61   29                                                            
CONECT   62   29                                                            
CONECT   63   30                                                            
CONECT   64   30                                                            
CONECT   65   31                                                            
CONECT   66   31                                                            
CONECT   67   32                                                            
CONECT   68   33                                                            
CONECT   69   33                                                            
CONECT   70   33                                                            
MASTER        0    0    0    0    0    0    0    0   70    0  150    0
END

RDKit          3D

70 75  0  0  0  0  0  0  0  0999 V2000
    1.6254    2.1818   -5.7430 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1027    1.3082   -4.6647 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1021    0.3704   -4.8127 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1599   -0.2482   -3.6410 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6771    0.2854   -2.7060 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7091   -0.0963   -1.3659 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6230    0.5713   -0.5374 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4580    1.6037   -1.0538 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4416    1.9222   -2.4555 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3521    2.9706   -3.0438 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4951    1.2502   -3.2793 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3152    2.4301   -0.0842 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6935    3.8211    0.1246 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5443    1.7537    1.2770 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2481    1.1970    1.8433 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7345    0.1082    0.9019 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4095   -0.5005    1.3851 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5529    0.5595    1.5478 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0707   -1.5933    0.3801 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9088   -2.7844    0.2780 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4667   -2.1281    0.7563 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5594   -2.0358   -0.0304 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9562   -2.5600    0.2690 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.2462   -3.6469   -0.7906 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0191   -3.1872    1.6599 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9515   -3.2959    2.4659 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6157   -2.7971    2.0800 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6812   -2.9222    2.8631 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3806   -3.6367    2.1300 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3647   -2.4740    2.0789 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3999   -1.8185    0.7009 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9963   -1.3841    0.2209 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.1413   -0.7103   -1.1525 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1673   -1.0584   -0.9598 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0058    2.1128   -6.6435 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6434    1.8871   -6.0159 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6312    3.2295   -5.4273 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4985    0.0473   -5.6517 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6802    2.6761   -4.0444 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8258    3.9270   -3.1141 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2721    3.1115   -2.4744 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3164    2.5574   -0.5099 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6605    4.3969   -0.8046 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6656    3.7566    0.4975 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2790    4.4054    0.8427 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2673    0.9356    1.1583 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9922    2.4588    1.9873 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5140    1.9993    1.9757 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4355    0.7703    2.8359 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4923   -0.6881    0.9026 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5731   -0.9234    2.3817 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3842    0.1638    1.8580 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1987   -3.1746    1.2578 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4640   -3.6052   -0.2986 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8254   -2.5161   -0.2587 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4448   -1.5653   -1.0067 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5757   -4.5075   -0.6692 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0996   -3.2718   -1.8103 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2709   -4.0268   -0.7322 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0114   -3.7336    3.4565 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3417   -4.0244    3.1553 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7365   -4.4622    1.5033 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0870   -1.7229    2.8296 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3677   -2.8286    2.3426 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8511   -2.5107   -0.0204 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0617   -0.9445    0.7452 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6499   -0.6036    0.9160 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5157   -1.4066   -1.9092 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8524    0.1218   -1.0943 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1946   -0.2924   -1.5050 H   0  0  0  0  0  0  0  0  0  0  0  0
  7  8  2  0
 25 26  2  0
 23 32  1  0
  8  9  1  0
  9 11  2  0
  5  6  2  0
  5 11  1  0
 25 29  1  0
 29 30  1  0
 30 31  1  0
 31 32  1  0
 23 25  1  0
 11  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
 32 33  1  0
  2  1  1  0
 12 13  1  0
 26 27  1  0
 16  7  1  0
 27 28  2  0
 27 21  1  0
 21 19  1  0
 15 14  1  0
 22 23  1  0
 16 17  1  0
  7  6  1  0
  6 34  1  0
 34 19  1  0
 19 17  1  0
 22 21  2  0
 17 18  1  0
 16 50  1  6
 15 16  1  0
 19 20  1  6
 14 12  1  0
 23 24  1  6
 12  8  1  0
  9 10  1  0
 26 60  1  0
 22 56  1  0
 29 61  1  0
 29 62  1  0
 30 63  1  0
 30 64  1  0
 31 65  1  0
 31 66  1  0
 32 67  1  1
 33 68  1  0
 33 69  1  0
 33 70  1  0
 15 48  1  0
 15 49  1  0
 14 46  1  0
 14 47  1  0
 12 42  1  6
  3 38  1  0
  1 35  1  0
  1 36  1  0
  1 37  1  0
 13 43  1  0
 13 44  1  0
 13 45  1  0
 17 51  1  1
 18 52  1  0
 20 53  1  0
 20 54  1  0
 20 55  1  0
 24 57  1  0
 24 58  1  0
 24 59  1  0
 10 39  1  0
 10 40  1  0
 10 41  1  0
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₀H₃₆O₄

Average Mass

460.6140 Da

Monoisotopic Mass

460.26136 Da

IUPAC Name

(4aS,5S)-3-[(2S,5R,6R,7R)-6-hydroxy-2,7,13,15-tetramethyl-8,11-dioxatetracyclo[7.6.1.0^{5,16}.0^{10,14}]hexadeca-1(16),9,12,14-tetraen-7-yl]-4a,5-dimethyl-2,4a,5,6,7,8-hexahydronaphthalen-2-one

Traditional Name

(4aS,5S)-3-[(2S,5R,6R,7R)-6-hydroxy-2,7,13,15-tetramethyl-8,11-dioxatetracyclo[7.6.1.0^{5,16}.0^{10,14}]hexadeca-1(16),9,12,14-tetraen-7-yl]-4a,5-dimethyl-5,6,7,8-tetrahydronaphthalen-2-one

CAS Registry Number

Not Available

SMILES

[H]O[C@]1([H])[C@@]2([H])C3=C(C(=C4C(OC([H])=C4C([H])([H])[H])=C3O[C@@]1(C1=C([H])[C@]3(C(=C([H])C1=O)C([H])([H])C([H])([H])C([H])([H])[C@]3([H])C([H])([H])[H])C([H])([H])[H])C([H])([H])[H])C([H])([H])[H])[C@@]([H])(C([H])([H])[H])C([H])([H])C2([H])[H]

InChI Identifier

InChI=1S/C30H36O4/c1-15-10-11-20-25-23(15)18(4)24-16(2)14-33-26(24)27(25)34-30(6,28(20)32)21-13-29(5)17(3)8-7-9-19(29)12-22(21)31/h12-15,17,20,28,32H,7-11H2,1-6H3/t15-,17-,20+,28+,29+,30+/m0/s1

InChI Key

PXLCJVXPHFFDDN-QYICRBEBSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, C₆D₆, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, C₆D₆, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, C₆D₆, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, C₆D₆, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, C₆D₆, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, C₆D₆, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, C₆D₆, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, C₆D₆, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, C₆D₆, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, C₆D₆, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, C₆D₆, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, C₆D₆, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, C₆D₆, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, C₆D₆, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, C₆D₆, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, C₆D₆, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, C₆D₆, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, C₆D₆, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, C₆D₆, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, C₆D₆, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Ligularia virgaurea	JEOL database	Saito, Y., et al, Tetrahedron 68, 10011 (2012)

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as eremophilane, 8,9-secoeremophilane and furoeremophilane sesquiterpenoids. These are sesquiterpenoids with a structure based either on the eremophilane skeleton, its 8,9-seco derivative, or the furoeremophilane skeleton. Eremophilanes have been shown to be derived from eudesmanes by migration of the methyl group at C-10 to C-5.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Eremophilane, 8,9-secoeremophilane and furoeremophilane sesquiterpenoids

Alternative Parents

Substituents

Eremophilane sesquiterpenoid
Naphthofuran
Chromane
Benzopyran
1-benzopyran
Tetralin
Benzofuran
Alkyl aryl ether
Benzenoid
Heteroaromatic compound
Furan
Cyclic ketone
Secondary alcohol
Ketone
Oxacycle
Ether
Organoheterocyclic compound
Carbonyl group
Alcohol
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic 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	6.26	ALOGPS
logP	6.56	ChemAxon
logS	-5.1	ALOGPS
pKa (Strongest Acidic)	13.5	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	59.67 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	135.44 m³·mol⁻¹	ChemAxon
Polarizability	53.48 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	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

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

102306567

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Saito, Y., et al. (2012). Saito, Y., et al, Tetrahedron 68, 10011 (2012). Tetrahedron.

Showing NP-Card for virgaurin C (NP0041806)

MOL for NP0041806 (virgaurin C)

3D MOL for NP0041806 (virgaurin C)

3D SDF for NP0041806 (virgaurin C)

3D-SDF for NP0041806 (virgaurin C)

PDB for NP0041806 (virgaurin C)

3D PDB for NP0041806 (virgaurin C)

SMILES for NP0041806 (virgaurin C)

INCHI for NP0041806 (virgaurin C)

Structure for NP0041806 (virgaurin C)

3D Structure for NP0041806 (virgaurin C)