NP-MRD: Showing NP-Card for Tetrahydrobisvertinolone (NP0006028)

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Record Information

Version

2.0

Created at

2020-12-09 03:06:27 UTC

Updated at

2021-07-15 16:53:38 UTC

NP-MRD ID

NP0006028

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Tetrahydrobisvertinolone

Provided By

NPAtlas

Description

Tetrahydrobisvertinolone is found in Penicillium terrestre. Tetrahydrobisvertinolone was first documented in 2005 (PMID: 16161481). Based on a literature review very few articles have been published on (1R,2R,6S,7R,9S)-4,13-bis[(4E)-hex-4-enoyl]-3,6,7,10,12-pentahydroxy-2,6,9,11-tetramethyl-8-oxatricyclo[7.4.0.0²,⁷]Trideca-3,10,12-trien-5-one.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242118253D          

 73 75  0  0  0  0            999 V2000
   -4.1161    5.0055    2.6898 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7701    3.7353    2.2403 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0362    2.8888    1.5296 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6206    1.6055    1.0476 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.8484    0.4288    1.6075 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4327    0.4398    1.2239 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6370    1.2223    1.8492 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8584   -0.3749    0.1787 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5598   -0.3457   -0.1567 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2618    0.5030    0.5354 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0579   -1.1976   -1.2310 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4377   -0.5343   -2.5649 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4049   -1.5321   -1.1844 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2891   -0.6595   -0.4293 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6068    0.6802   -0.8385 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4649    1.3506   -0.1512 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0570    1.3932   -1.9839 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8085    2.7043   -2.2554 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7196    3.6129   -1.0916 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7308    4.0810   -0.3876 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5364    4.9989    0.7780 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9518   -1.0909    0.6723 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.8546   -2.4598    1.1458 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5586   -2.9461    2.3613 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1114   -3.3006    0.4702 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9831   -4.6438    0.9014 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3787   -2.9632   -0.7448 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9622   -3.8641   -1.8535 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0841   -3.3852   -0.5831 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7318   -2.5584   -1.3017 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6180   -2.9986   -2.6505 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1579   -2.6151   -0.9296 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.9969   -3.1901   -2.0441 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3887   -3.4521    0.1838 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7034   -1.3026   -0.5611 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8763   -0.9749   -0.8727 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7518    5.5980    3.3484 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9267    5.5903    1.7525 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1453    4.7564    3.1695 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8227    3.5145    2.4894 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9984    3.1626    1.3101 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6551    1.5457    1.4416 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7036    1.5612   -0.0604 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9062    0.5420    2.7288 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3682   -0.5106    1.3676 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1976    1.5249    0.4741 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3613   -0.7182   -3.2828 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3268   -1.1190   -2.9562 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7822    0.4972   -2.4475 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7537   -1.5168   -2.2562 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0128    1.7481   -1.7671 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0767    0.8334   -2.9237 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3462    3.2204   -3.1225 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8643    2.5288   -2.4971 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7278    3.9336   -0.7782 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7293    3.7766   -0.6789 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7286    5.7345    0.5999 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4441    5.5363    1.0532 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2154    4.3864    1.6538 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6600   -0.5907    1.7178 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5349   -3.3650    2.0641 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6385   -2.1264    3.1008 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9650   -3.7682    2.8470 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0453   -4.8779    1.2643 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5509   -4.8628   -1.7004 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0725   -3.8786   -1.6678 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8147   -3.4278   -2.8509 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5471   -3.9917   -2.6797 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4909   -3.1793   -3.0098 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9576   -2.6153   -2.1511 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3066   -4.2568   -1.8345 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7497   -3.2502    0.9235 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  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
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  6  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
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 14 22  2  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
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 24 26  2  0  0  0  0
 26 27  1  0  0  0  0
 26 28  1  0  0  0  0
 28 29  1  6  0  0  0
 28 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  6  0  0  0
 31 33  1  0  0  0  0
 33 34  1  0  0  0  0
 33 35  1  1  0  0  0
 33 36  1  0  0  0  0
 36 37  2  0  0  0  0
 36  8  1  0  0  0  0
 31 11  1  0  0  0  0
 28 13  1  0  0  0  0
  1 38  1  0  0  0  0
  1 39  1  0  0  0  0
  1 40  1  0  0  0  0
  2 41  1  0  0  0  0
  3 42  1  0  0  0  0
  4 43  1  0  0  0  0
  4 44  1  0  0  0  0
  5 45  1  0  0  0  0
  5 46  1  0  0  0  0
 10 47  1  0  0  0  0
 12 48  1  0  0  0  0
 12 49  1  0  0  0  0
 12 50  1  0  0  0  0
 13 51  1  6  0  0  0
 17 52  1  0  0  0  0
 17 53  1  0  0  0  0
 18 54  1  0  0  0  0
 18 55  1  0  0  0  0
 19 56  1  0  0  0  0
 20 57  1  0  0  0  0
 21 58  1  0  0  0  0
 21 59  1  0  0  0  0
 21 60  1  0  0  0  0
 23 61  1  0  0  0  0
 25 62  1  0  0  0  0
 25 63  1  0  0  0  0
 25 64  1  0  0  0  0
 27 65  1  0  0  0  0
 29 66  1  0  0  0  0
 29 67  1  0  0  0  0
 29 68  1  0  0  0  0
 32 69  1  0  0  0  0
 34 70  1  0  0  0  0
 34 71  1  0  0  0  0
 34 72  1  0  0  0  0
 35 73  1  0  0  0  0
M  END

     RDKit          3D

 73 75  0  0  0  0  0  0  0  0999 V2000
   -4.1161    5.0055    2.6898 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7701    3.7353    2.2403 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0362    2.8888    1.5296 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6206    1.6055    1.0476 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8484    0.4288    1.6075 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4327    0.4398    1.2239 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6370    1.2223    1.8492 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8584   -0.3749    0.1787 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5598   -0.3457   -0.1567 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.0579   -1.1976   -1.2310 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4377   -0.5343   -2.5649 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4049   -1.5321   -1.1844 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2891   -0.6595   -0.4293 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6068    0.6802   -0.8385 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4649    1.3506   -0.1512 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0570    1.3932   -1.9839 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8085    2.7043   -2.2554 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7196    3.6129   -1.0916 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7308    4.0810   -0.3876 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5364    4.9989    0.7780 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9518   -1.0909    0.6723 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7832   -0.1960    1.3802 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8546   -2.4598    1.1458 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5586   -2.9461    2.3613 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1114   -3.3006    0.4702 C   0  0  0  0  0  0  0  0  0  0  0  0
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  1 40  1  0
  2 41  1  0
  3 42  1  0
  4 43  1  0
  4 44  1  0
  5 45  1  0
  5 46  1  0
 10 47  1  0
 12 48  1  0
 12 49  1  0
 12 50  1  0
 13 51  1  6
 17 52  1  0
 17 53  1  0
 18 54  1  0
 18 55  1  0
 19 56  1  0
 20 57  1  0
 21 58  1  0
 21 59  1  0
 21 60  1  0
 23 61  1  0
 25 62  1  0
 25 63  1  0
 25 64  1  0
 27 65  1  0
 29 66  1  0
 29 67  1  0
 29 68  1  0
 32 69  1  0
 34 70  1  0
 34 71  1  0
 34 72  1  0
 35 73  1  0
M  END


  Mrv1652306242118253D          

 73 75  0  0  0  0            999 V2000
   -4.1161    5.0055    2.6898 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7701    3.7353    2.2403 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0362    2.8888    1.5296 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6206    1.6055    1.0476 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.8484    0.4288    1.6075 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4327    0.4398    1.2239 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6370    1.2223    1.8492 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8584   -0.3749    0.1787 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5598   -0.3457   -0.1567 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2618    0.5030    0.5354 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0579   -1.1976   -1.2310 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4377   -0.5343   -2.5649 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4049   -1.5321   -1.1844 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2891   -0.6595   -0.4293 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6068    0.6802   -0.8385 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4649    1.3506   -0.1512 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0570    1.3932   -1.9839 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8085    2.7043   -2.2554 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7196    3.6129   -1.0916 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7308    4.0810   -0.3876 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5364    4.9989    0.7780 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9518   -1.0909    0.6723 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7832   -0.1960    1.3802 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8546   -2.4598    1.1458 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5586   -2.9461    2.3613 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1114   -3.3006    0.4702 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9831   -4.6438    0.9014 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3787   -2.9632   -0.7448 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9622   -3.8641   -1.8535 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0841   -3.3852   -0.5831 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7318   -2.5584   -1.3017 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6180   -2.9986   -2.6505 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1579   -2.6151   -0.9296 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.9969   -3.1901   -2.0441 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3887   -3.4521    0.1838 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7034   -1.3026   -0.5611 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8763   -0.9749   -0.8727 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7518    5.5980    3.3484 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9267    5.5903    1.7525 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1453    4.7564    3.1695 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8227    3.5145    2.4894 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9984    3.1626    1.3101 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6551    1.5457    1.4416 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7036    1.5612   -0.0604 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9062    0.5420    2.7288 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3682   -0.5106    1.3676 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1976    1.5249    0.4741 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3613   -0.7182   -3.2828 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3268   -1.1190   -2.9562 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7822    0.4972   -2.4475 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7537   -1.5168   -2.2562 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0128    1.7481   -1.7671 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0767    0.8334   -2.9237 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3462    3.2204   -3.1225 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8643    2.5288   -2.4971 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7278    3.9336   -0.7782 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7293    3.7766   -0.6789 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7286    5.7345    0.5999 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4441    5.5363    1.0532 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2154    4.3864    1.6538 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6600   -0.5907    1.7178 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5349   -3.3650    2.0641 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6385   -2.1264    3.1008 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9650   -3.7682    2.8470 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0453   -4.8779    1.2643 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5509   -4.8628   -1.7004 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0725   -3.8786   -1.6678 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8147   -3.4278   -2.8509 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5471   -3.9917   -2.6797 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4909   -3.1793   -3.0098 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9576   -2.6153   -2.1511 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3066   -4.2568   -1.8345 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7497   -3.2502    0.9235 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  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
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  6  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 14 22  2  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  2  0  0  0  0
 26 27  1  0  0  0  0
 26 28  1  0  0  0  0
 28 29  1  6  0  0  0
 28 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  6  0  0  0
 31 33  1  0  0  0  0
 33 34  1  0  0  0  0
 33 35  1  1  0  0  0
 33 36  1  0  0  0  0
 36 37  2  0  0  0  0
 36  8  1  0  0  0  0
 31 11  1  0  0  0  0
 28 13  1  0  0  0  0
  1 38  1  0  0  0  0
  1 39  1  0  0  0  0
  1 40  1  0  0  0  0
  2 41  1  0  0  0  0
  3 42  1  0  0  0  0
  4 43  1  0  0  0  0
  4 44  1  0  0  0  0
  5 45  1  0  0  0  0
  5 46  1  0  0  0  0
 10 47  1  0  0  0  0
 12 48  1  0  0  0  0
 12 49  1  0  0  0  0
 12 50  1  0  0  0  0
 13 51  1  6  0  0  0
 17 52  1  0  0  0  0
 17 53  1  0  0  0  0
 18 54  1  0  0  0  0
 18 55  1  0  0  0  0
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 21 58  1  0  0  0  0
 21 59  1  0  0  0  0
 21 60  1  0  0  0  0
 23 61  1  0  0  0  0
 25 62  1  0  0  0  0
 25 63  1  0  0  0  0
 25 64  1  0  0  0  0
 27 65  1  0  0  0  0
 29 66  1  0  0  0  0
 29 67  1  0  0  0  0
 29 68  1  0  0  0  0
 32 69  1  0  0  0  0
 34 70  1  0  0  0  0
 34 71  1  0  0  0  0
 34 72  1  0  0  0  0
 35 73  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0006028

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C(C(=O)C([H])([H])C([H])([H])C(\[H])=C(/[H])C([H])([H])[H])[C@@]2([H])[C@](O[C@]3(O[H])[C@]2(C(O[H])=C(C(=O)C([H])([H])C([H])([H])C(\[H])=C(/[H])C([H])([H])[H])C(=O)[C@@]3(O[H])C([H])([H])[H])C([H])([H])[H])(C(O[H])=C1C([H])([H])[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C28H36O9/c1-7-9-11-13-16(29)18-20(31)15(3)22(32)26(5)21(18)25(4)23(33)19(17(30)14-12-10-8-2)24(34)27(6,35)28(25,36)37-26/h7-10,21,31-33,35-36H,11-14H2,1-6H3/b9-7+,10-8+/t21-,25-,26+,27+,28-/m1/s1

> <INCHI_KEY>
FEQQKMZNFKCWST-QCNVSJCTSA-N

> <FORMULA>
C28H36O9

> <MOLECULAR_WEIGHT>
516.587

> <EXACT_MASS>
516.235932739

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
73

> <JCHEM_AVERAGE_POLARIZABILITY>
54.46590187046469

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,2R,6S,7R,9S)-4,13-bis[(4E)-hex-4-enoyl]-3,6,7,10,12-pentahydroxy-2,6,9,11-tetramethyl-8-oxatricyclo[7.4.0.0^{2,7}]trideca-3,10,12-trien-5-one

> <ALOGPS_LOGP>
2.24

> <JCHEM_LOGP>
2.9502601409999993

> <ALOGPS_LOGS>
-4.32

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
6.196257389002387

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.122097904883491

> <JCHEM_PKA_STRONGEST_BASIC>
-4.3875486179683785

> <JCHEM_POLAR_SURFACE_AREA>
161.59

> <JCHEM_REFRACTIVITY>
141.42250000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.47e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2R,6S,7R,9S)-4,13-bis[(4E)-hex-4-enoyl]-3,6,7,10,12-pentahydroxy-2,6,9,11-tetramethyl-8-oxatricyclo[7.4.0.0^{2,7}]trideca-3,10,12-trien-5-one

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 73 75  0  0  0  0  0  0  0  0999 V2000
   -4.1161    5.0055    2.6898 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7701    3.7353    2.2403 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0362    2.8888    1.5296 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6206    1.6055    1.0476 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8484    0.4288    1.6075 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4327    0.4398    1.2239 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6370    1.2223    1.8492 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8584   -0.3749    0.1787 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5598   -0.3457   -0.1567 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2618    0.5030    0.5354 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0579   -1.1976   -1.2310 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4377   -0.5343   -2.5649 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4049   -1.5321   -1.1844 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2891   -0.6595   -0.4293 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6068    0.6802   -0.8385 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4649    1.3506   -0.1512 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0570    1.3932   -1.9839 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8085    2.7043   -2.2554 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7196    3.6129   -1.0916 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7308    4.0810   -0.3876 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5364    4.9989    0.7780 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9518   -1.0909    0.6723 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7832   -0.1960    1.3802 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8546   -2.4598    1.1458 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5586   -2.9461    2.3613 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1114   -3.3006    0.4702 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9831   -4.6438    0.9014 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3787   -2.9632   -0.7448 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9622   -3.8641   -1.8535 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0841   -3.3852   -0.5831 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7318   -2.5584   -1.3017 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6180   -2.9986   -2.6505 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1579   -2.6151   -0.9296 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.9969   -3.1901   -2.0441 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3887   -3.4521    0.1838 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7034   -1.3026   -0.5611 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8763   -0.9749   -0.8727 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7518    5.5980    3.3484 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.1453    4.7564    3.1695 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8227    3.5145    2.4894 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9984    3.1626    1.3101 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6551    1.5457    1.4416 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7036    1.5612   -0.0604 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9062    0.5420    2.7288 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3682   -0.5106    1.3676 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1976    1.5249    0.4741 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3613   -0.7182   -3.2828 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3268   -1.1190   -2.9562 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7822    0.4972   -2.4475 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7537   -1.5168   -2.2562 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0128    1.7481   -1.7671 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0767    0.8334   -2.9237 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3462    3.2204   -3.1225 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8643    2.5288   -2.4971 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7278    3.9336   -0.7782 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7293    3.7766   -0.6789 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7286    5.7345    0.5999 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4441    5.5363    1.0532 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2154    4.3864    1.6538 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6600   -0.5907    1.7178 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5349   -3.3650    2.0641 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6385   -2.1264    3.1008 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9650   -3.7682    2.8470 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0453   -4.8779    1.2643 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5509   -4.8628   -1.7004 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0725   -3.8786   -1.6678 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8147   -3.4278   -2.8509 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5471   -3.9917   -2.6797 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4909   -3.1793   -3.0098 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9576   -2.6153   -2.1511 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3066   -4.2568   -1.8345 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7497   -3.2502    0.9235 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  2  0
  9 10  1  0
  9 11  1  0
 11 12  1  6
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 14 22  2  0
 22 23  1  0
 22 24  1  0
 24 25  1  0
 24 26  2  0
 26 27  1  0
 26 28  1  0
 28 29  1  6
 28 30  1  0
 30 31  1  0
 31 32  1  6
 31 33  1  0
 33 34  1  0
 33 35  1  1
 33 36  1  0
 36 37  2  0
 36  8  1  0
 31 11  1  0
 28 13  1  0
  1 38  1  0
  1 39  1  0
  1 40  1  0
  2 41  1  0
  3 42  1  0
  4 43  1  0
  4 44  1  0
  5 45  1  0
  5 46  1  0
 10 47  1  0
 12 48  1  0
 12 49  1  0
 12 50  1  0
 13 51  1  6
 17 52  1  0
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 21 58  1  0
 21 59  1  0
 21 60  1  0
 23 61  1  0
 25 62  1  0
 25 63  1  0
 25 64  1  0
 27 65  1  0
 29 66  1  0
 29 67  1  0
 29 68  1  0
 32 69  1  0
 34 70  1  0
 34 71  1  0
 34 72  1  0
 35 73  1  0
M  END

HEADER    PROTEIN                                 24-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-JUN-21         0                                  
HETATM    1  C   UNK     0      -4.116   5.005   2.690  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.770   3.735   2.240  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.036   2.889   1.530  0.00  0.00           C+0
HETATM    4  C   UNK     0      -4.621   1.605   1.048  0.00  0.00           C+0
HETATM    5  C   UNK     0      -3.848   0.429   1.607  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.433   0.440   1.224  0.00  0.00           C+0
HETATM    7  O   UNK     0      -1.637   1.222   1.849  0.00  0.00           O+0
HETATM    8  C   UNK     0      -1.858  -0.375   0.179  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.560  -0.346  -0.157  0.00  0.00           C+0
HETATM   10  O   UNK     0       0.262   0.503   0.535  0.00  0.00           O+0
HETATM   11  C   UNK     0      -0.058  -1.198  -1.231  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.438  -0.534  -2.565  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.405  -1.532  -1.184  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.289  -0.660  -0.429  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.607   0.680  -0.839  0.00  0.00           C+0
HETATM   16  O   UNK     0       3.465   1.351  -0.151  0.00  0.00           O+0
HETATM   17  C   UNK     0       2.057   1.393  -1.984  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.809   2.704  -2.255  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.720   3.613  -1.092  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.731   4.081  -0.388  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.536   4.999   0.778  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.952  -1.091   0.672  0.00  0.00           C+0
HETATM   23  O   UNK     0       3.783  -0.196   1.380  0.00  0.00           O+0
HETATM   24  C   UNK     0       2.855  -2.460   1.146  0.00  0.00           C+0
HETATM   25  C   UNK     0       3.559  -2.946   2.361  0.00  0.00           C+0
HETATM   26  C   UNK     0       2.111  -3.301   0.470  0.00  0.00           C+0
HETATM   27  O   UNK     0       1.983  -4.644   0.901  0.00  0.00           O+0
HETATM   28  C   UNK     0       1.379  -2.963  -0.745  0.00  0.00           C+0
HETATM   29  C   UNK     0       1.962  -3.864  -1.853  0.00  0.00           C+0
HETATM   30  O   UNK     0       0.084  -3.385  -0.583  0.00  0.00           O+0
HETATM   31  C   UNK     0      -0.732  -2.558  -1.302  0.00  0.00           C+0
HETATM   32  O   UNK     0      -0.618  -2.999  -2.651  0.00  0.00           O+0
HETATM   33  C   UNK     0      -2.158  -2.615  -0.930  0.00  0.00           C+0
HETATM   34  C   UNK     0      -2.997  -3.190  -2.044  0.00  0.00           C+0
HETATM   35  O   UNK     0      -2.389  -3.452   0.184  0.00  0.00           O+0
HETATM   36  C   UNK     0      -2.703  -1.303  -0.561  0.00  0.00           C+0
HETATM   37  O   UNK     0      -3.876  -0.975  -0.873  0.00  0.00           O+0
HETATM   38  H   UNK     0      -4.752   5.598   3.348  0.00  0.00           H+0
HETATM   39  H   UNK     0      -3.927   5.590   1.753  0.00  0.00           H+0
HETATM   40  H   UNK     0      -3.145   4.756   3.170  0.00  0.00           H+0
HETATM   41  H   UNK     0      -5.823   3.515   2.489  0.00  0.00           H+0
HETATM   42  H   UNK     0      -2.998   3.163   1.310  0.00  0.00           H+0
HETATM   43  H   UNK     0      -5.655   1.546   1.442  0.00  0.00           H+0
HETATM   44  H   UNK     0      -4.704   1.561  -0.060  0.00  0.00           H+0
HETATM   45  H   UNK     0      -3.906   0.542   2.729  0.00  0.00           H+0
HETATM   46  H   UNK     0      -4.368  -0.511   1.368  0.00  0.00           H+0
HETATM   47  H   UNK     0       0.198   1.525   0.474  0.00  0.00           H+0
HETATM   48  H   UNK     0       0.361  -0.718  -3.283  0.00  0.00           H+0
HETATM   49  H   UNK     0      -1.327  -1.119  -2.956  0.00  0.00           H+0
HETATM   50  H   UNK     0      -0.782   0.497  -2.447  0.00  0.00           H+0
HETATM   51  H   UNK     0       1.754  -1.517  -2.256  0.00  0.00           H+0
HETATM   52  H   UNK     0       1.013   1.748  -1.767  0.00  0.00           H+0
HETATM   53  H   UNK     0       2.077   0.833  -2.924  0.00  0.00           H+0
HETATM   54  H   UNK     0       2.346   3.220  -3.123  0.00  0.00           H+0
HETATM   55  H   UNK     0       3.864   2.529  -2.497  0.00  0.00           H+0
HETATM   56  H   UNK     0       1.728   3.934  -0.778  0.00  0.00           H+0
HETATM   57  H   UNK     0       4.729   3.777  -0.679  0.00  0.00           H+0
HETATM   58  H   UNK     0       2.729   5.734   0.600  0.00  0.00           H+0
HETATM   59  H   UNK     0       4.444   5.536   1.053  0.00  0.00           H+0
HETATM   60  H   UNK     0       3.215   4.386   1.654  0.00  0.00           H+0
HETATM   61  H   UNK     0       4.660  -0.591   1.718  0.00  0.00           H+0
HETATM   62  H   UNK     0       4.535  -3.365   2.064  0.00  0.00           H+0
HETATM   63  H   UNK     0       3.639  -2.126   3.101  0.00  0.00           H+0
HETATM   64  H   UNK     0       2.965  -3.768   2.847  0.00  0.00           H+0
HETATM   65  H   UNK     0       1.045  -4.878   1.264  0.00  0.00           H+0
HETATM   66  H   UNK     0       1.551  -4.863  -1.700  0.00  0.00           H+0
HETATM   67  H   UNK     0       3.072  -3.879  -1.668  0.00  0.00           H+0
HETATM   68  H   UNK     0       1.815  -3.428  -2.851  0.00  0.00           H+0
HETATM   69  H   UNK     0      -0.547  -3.992  -2.680  0.00  0.00           H+0
HETATM   70  H   UNK     0      -2.491  -3.179  -3.010  0.00  0.00           H+0
HETATM   71  H   UNK     0      -3.958  -2.615  -2.151  0.00  0.00           H+0
HETATM   72  H   UNK     0      -3.307  -4.257  -1.835  0.00  0.00           H+0
HETATM   73  H   UNK     0      -1.750  -3.250   0.924  0.00  0.00           H+0
CONECT    1    2   38   39   40                                             
CONECT    2    1    3   41                                                  
CONECT    3    2    4   42                                                  
CONECT    4    3    5   43   44                                             
CONECT    5    4    6   45   46                                             
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   36                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9   47                                                       
CONECT   11    9   12   13   31                                             
CONECT   12   11   48   49   50                                             
CONECT   13   11   14   28   51                                             
CONECT   14   13   15   22                                                  
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   52   53                                             
CONECT   18   17   19   54   55                                             
CONECT   19   18   20   56                                                  
CONECT   20   19   21   57                                                  
CONECT   21   20   58   59   60                                             
CONECT   22   14   23   24                                                  
CONECT   23   22   61                                                       
CONECT   24   22   25   26                                                  
CONECT   25   24   62   63   64                                             
CONECT   26   24   27   28                                                  
CONECT   27   26   65                                                       
CONECT   28   26   29   30   13                                             
CONECT   29   28   66   67   68                                             
CONECT   30   28   31                                                       
CONECT   31   30   32   33   11                                             
CONECT   32   31   69                                                       
CONECT   33   31   34   35   36                                             
CONECT   34   33   70   71   72                                             
CONECT   35   33   73                                                       
CONECT   36   33   37    8                                                  
CONECT   37   36                                                            
CONECT   38    1                                                            
CONECT   39    1                                                            
CONECT   40    1                                                            
CONECT   41    2                                                            
CONECT   42    3                                                            
CONECT   43    4                                                            
CONECT   44    4                                                            
CONECT   45    5                                                            
CONECT   46    5                                                            
CONECT   47   10                                                            
CONECT   48   12                                                            
CONECT   49   12                                                            
CONECT   50   12                                                            
CONECT   51   13                                                            
CONECT   52   17                                                            
CONECT   53   17                                                            
CONECT   54   18                                                            
CONECT   55   18                                                            
CONECT   56   19                                                            
CONECT   57   20                                                            
CONECT   58   21                                                            
CONECT   59   21                                                            
CONECT   60   21                                                            
CONECT   61   23                                                            
CONECT   62   25                                                            
CONECT   63   25                                                            
CONECT   64   25                                                            
CONECT   65   27                                                            
CONECT   66   29                                                            
CONECT   67   29                                                            
CONECT   68   29                                                            
CONECT   69   32                                                            
CONECT   70   34                                                            
CONECT   71   34                                                            
CONECT   72   34                                                            
CONECT   73   35                                                            
MASTER        0    0    0    0    0    0    0    0   73    0  150    0
END

RDKit          3D

73 75  0  0  0  0  0  0  0  0999 V2000
   -4.1161    5.0055    2.6898 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7701    3.7353    2.2403 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0362    2.8888    1.5296 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6206    1.6055    1.0476 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8484    0.4288    1.6075 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4327    0.4398    1.2239 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6370    1.2223    1.8492 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8584   -0.3749    0.1787 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5598   -0.3457   -0.1567 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2618    0.5030    0.5354 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0579   -1.1976   -1.2310 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4377   -0.5343   -2.5649 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4049   -1.5321   -1.1844 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2891   -0.6595   -0.4293 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6068    0.6802   -0.8385 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4649    1.3506   -0.1512 O   0  0  0  0  0  0  0  0  0  0  0  0
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    2.8085    2.7043   -2.2554 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7196    3.6129   -1.0916 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7308    4.0810   -0.3876 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5364    4.9989    0.7780 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9518   -1.0909    0.6723 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7832   -0.1960    1.3802 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8546   -2.4598    1.1458 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5586   -2.9461    2.3613 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1114   -3.3006    0.4702 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9831   -4.6438    0.9014 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3787   -2.9632   -0.7448 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9622   -3.8641   -1.8535 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0841   -3.3852   -0.5831 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7318   -2.5584   -1.3017 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6180   -2.9986   -2.6505 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1579   -2.6151   -0.9296 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.9969   -3.1901   -2.0441 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3887   -3.4521    0.1838 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7034   -1.3026   -0.5611 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8763   -0.9749   -0.8727 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7518    5.5980    3.3484 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9267    5.5903    1.7525 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1453    4.7564    3.1695 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8227    3.5145    2.4894 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9984    3.1626    1.3101 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6551    1.5457    1.4416 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7036    1.5612   -0.0604 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9062    0.5420    2.7288 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3682   -0.5106    1.3676 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1976    1.5249    0.4741 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3613   -0.7182   -3.2828 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3268   -1.1190   -2.9562 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7822    0.4972   -2.4475 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7537   -1.5168   -2.2562 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0128    1.7481   -1.7671 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0767    0.8334   -2.9237 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3462    3.2204   -3.1225 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8643    2.5288   -2.4971 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7278    3.9336   -0.7782 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7293    3.7766   -0.6789 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7286    5.7345    0.5999 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4441    5.5363    1.0532 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2154    4.3864    1.6538 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6600   -0.5907    1.7178 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5349   -3.3650    2.0641 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6385   -2.1264    3.1008 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9650   -3.7682    2.8470 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0453   -4.8779    1.2643 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5509   -4.8628   -1.7004 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0725   -3.8786   -1.6678 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8147   -3.4278   -2.8509 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5471   -3.9917   -2.6797 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4909   -3.1793   -3.0098 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9576   -2.6153   -2.1511 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3066   -4.2568   -1.8345 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7497   -3.2502    0.9235 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  2  0
  9 10  1  0
  9 11  1  0
 11 12  1  6
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 14 22  2  0
 22 23  1  0
 22 24  1  0
 24 25  1  0
 24 26  2  0
 26 27  1  0
 26 28  1  0
 28 29  1  6
 28 30  1  0
 30 31  1  0
 31 32  1  6
 31 33  1  0
 33 34  1  0
 33 35  1  1
 33 36  1  0
 36 37  2  0
 36  8  1  0
 31 11  1  0
 28 13  1  0
  1 38  1  0
  1 39  1  0
  1 40  1  0
  2 41  1  0
  3 42  1  0
  4 43  1  0
  4 44  1  0
  5 45  1  0
  5 46  1  0
 10 47  1  0
 12 48  1  0
 12 49  1  0
 12 50  1  0
 13 51  1  6
 17 52  1  0
 17 53  1  0
 18 54  1  0
 18 55  1  0
 19 56  1  0
 20 57  1  0
 21 58  1  0
 21 59  1  0
 21 60  1  0
 23 61  1  0
 25 62  1  0
 25 63  1  0
 25 64  1  0
 27 65  1  0
 29 66  1  0
 29 67  1  0
 29 68  1  0
 32 69  1  0
 34 70  1  0
 34 71  1  0
 34 72  1  0
 35 73  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Not Available

Chemical Formula

C₂₈H₃₆O₉

Average Mass

516.5870 Da

Monoisotopic Mass

516.23593 Da

IUPAC Name

(1R,2R,6S,7R,9S)-4,13-bis[(4E)-hex-4-enoyl]-3,6,7,10,12-pentahydroxy-2,6,9,11-tetramethyl-8-oxatricyclo[7.4.0.0^{2,7}]trideca-3,10,12-trien-5-one

Traditional Name

(1R,2R,6S,7R,9S)-4,13-bis[(4E)-hex-4-enoyl]-3,6,7,10,12-pentahydroxy-2,6,9,11-tetramethyl-8-oxatricyclo[7.4.0.0^{2,7}]trideca-3,10,12-trien-5-one

CAS Registry Number

Not Available

SMILES

C\C=C\CCC(=O)C1=C(O)C(C)=C(O)[C@@]2(C)O[C@]3(O)[C@](C)([C@@H]12)C(O)=C(C(=O)CC\C=C\C)C(=O)[C@]3(C)O

InChI Identifier

InChI=1S/C28H36O9/c1-7-9-11-13-16(29)18-20(31)15(3)22(32)26(5)21(18)25(4)23(33)19(17(30)14-12-10-8-2)24(34)27(6,35)28(25,36)37-26/h7-10,21,31-33,35-36H,11-14H2,1-6H3/b9-7+,10-8+/t21-,25-,26+,27+,28-/m1/s1

InChI Key

FEQQKMZNFKCWST-QCNVSJCTSA-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
Penicillium terrestre	NPAtlas	16161481

Chemical Taxonomy

Classification

Not classified

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	2.24	ALOGPS
logP	2.95	ChemAxon
logS	-4.3	ALOGPS
pKa (Strongest Acidic)	3.12	ChemAxon
pKa (Strongest Basic)	-4.4	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	161.59 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	141.42 m³·mol⁻¹	ChemAxon
Polarizability	54.47 Å³	ChemAxon
Number of Rings	3	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

NPAtlas ID

NPA018375

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

9447318

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11272310

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Liu W, Gu Q, Zhu W, Cui C, Fan G: Two new benzoquinone derivatives and two new bisorbicillinoids were isolated from a marine-derived fungus Penicillium terrestre. J Antibiot (Tokyo). 2005 Jul;58(7):441-6. doi: 10.1038/ja.2005.57. [PubMed:16161481 ]

Showing NP-Card for Tetrahydrobisvertinolone (NP0006028)

MOL for NP0006028 (Tetrahydrobisvertinolone)

3D MOL for NP0006028 (Tetrahydrobisvertinolone)

3D SDF for NP0006028 (Tetrahydrobisvertinolone)

3D-SDF for NP0006028 (Tetrahydrobisvertinolone)

PDB for NP0006028 (Tetrahydrobisvertinolone)

3D PDB for NP0006028 (Tetrahydrobisvertinolone)

SMILES for NP0006028 (Tetrahydrobisvertinolone)

INCHI for NP0006028 (Tetrahydrobisvertinolone)

Structure for NP0006028 (Tetrahydrobisvertinolone)

3D Structure for NP0006028 (Tetrahydrobisvertinolone)