NP-MRD: Showing NP-Card for 6-(but-2-en-2-yl)-3,9'-dihydroxy-10'-(hydroxymethyl)-7'-methoxy-5,6',14',16'-tetramethyl-2',20'-dioxaspiro[oxane-2,21'-tricyclo[17.3.1.0⁴,⁹]tricosane]-5',10',12',16'-tetraen-3'-one (NP0301107)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-10 13:51:52 UTC

Updated at

2022-09-10 13:51:52 UTC

NP-MRD ID

NP0301107

Secondary Accession Numbers

None

Natural Product Identification

Common Name

6-(but-2-en-2-yl)-3,9'-dihydroxy-10'-(hydroxymethyl)-7'-methoxy-5,6',14',16'-tetramethyl-2',20'-dioxaspiro[oxane-2,21'-tricyclo[17.3.1.0⁴,⁹]tricosane]-5',10',12',16'-tetraen-3'-one

Description

6-(But-2-en-2-yl)-3,9'-dihydroxy-10'-(hydroxymethyl)-7'-methoxy-5,6',14',16'-tetramethyl-2',20'-dioxaspiro[oxane-2,21'-tricyclo[17.3.1.0⁴,⁹]Tricosane]-5',10',12',16'-tetraen-3'-one belongs to the class of organic compounds known as milbemycins. These are a group of macrolides with a structure containing a 16-membered lactone ring fused to a 1,7-dioxaspiroundecane ring system and to either a benzofuran (or hydrogenated derivative thereof). In some cases (e.G. Milbemycin E), the tetrahydrofuranyl ring is missing. Milbemycins can be o-glycosylated at C13 to form Avermectins. Milbemycins are produced by Streptomyces species. 6-(But-2-en-2-yl)-3,9'-dihydroxy-10'-(hydroxymethyl)-7'-methoxy-5,6',14',16'-tetramethyl-2',20'-dioxaspiro[oxane-2,21'-tricyclo[17.3.1.0⁴,⁹]Tricosane]-5',10',12',16'-tetraen-3'-one is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004161503342D          

 43 46  0  0  0  0            999 V2000
    7.8306    2.5672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0544    2.2878    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4242    2.8203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5703    3.6322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9402    4.1647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7164    4.4442    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1640    3.8853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8688    2.7566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6480    2.5408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5019    1.7289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0179    3.0733    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2147    2.2721    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2417    2.7939    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6115    3.3264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7576    4.1384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1275    4.6709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2736    5.4828    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6435    6.0153    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7896    6.8273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1595    7.3598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5658    7.1067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1959    6.5742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0498    5.7623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9722    6.8537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6023    6.3212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4562    5.5092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0863    4.9767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8625    5.2562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0087    6.0681    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3513    4.3914    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2052    3.5795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8353    3.0469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0591    2.7675    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2828    2.4880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6527    3.0205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1235    2.7411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7988    3.8325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5750    4.1120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7211    4.9239    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1367    1.6761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3605    1.3966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2144    0.5847    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7669    1.1436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  3  9  1  0  0  0  0
  9 10  1  0  0  0  0
  7 11  1  0  0  0  0
 11 12  2  0  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  1  0  0  0  0
 16 17  1  0  0  0  0
 18 17  1  4  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 24 22  1  4  0  0  0
 24 25  2  0  0  0  0
 26 25  1  4  0  0  0
 26 27  2  0  0  0  0
  5 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 16 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 14 32  1  0  0  0  0
 31 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 35 37  1  0  0  0  0
 37 38  1  0  0  0  0
 31 38  1  0  0  0  0
 38 39  1  0  0  0  0
 34 40  1  0  0  0  0
 40 41  2  0  0  0  0
 41 42  1  4  0  0  0
 40 43  1  0  0  0  0
M  END

     RDKit          3D

 95 98  0  0  0  0  0  0  0  0999 V2000
    6.4380    0.2460   -1.4784 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8370   -0.8351   -0.5638 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0786   -1.4091    0.3197 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6521   -2.5102    1.1838 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6595   -1.0254    0.5188 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.3180   -0.0348   -0.3398 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9485    0.2580   -0.3805 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2106   -1.0175   -0.5788 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8366   -0.8249   -1.1465 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0076    0.0865   -2.3721 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4775    1.4044   -1.7378 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2776    2.5617   -2.6390 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7794    3.7637   -1.9036 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0991    3.7349   -0.9300 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0277    4.6730    0.2290 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2731    2.7957   -0.8840 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5905    3.4944   -0.9312 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.9845    4.1596    0.3649 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6162    2.5375   -1.4205 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4606    1.8647   -0.6677 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1149    1.0757    0.5076 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2016    0.1062    0.5455 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3299    0.0391    1.7553 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4643   -1.1794    2.4209 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0490   -0.8837   -0.5521 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.6604   -0.1565   -1.6729 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3710   -1.5212   -0.8612 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7107   -2.6915   -0.0199 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.3873   -2.2662    1.1474 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6576   -2.7752    1.2499 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6032   -3.5522    0.4035 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8933   -4.9388    0.9828 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3724   -3.1356    0.2837 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9585   -1.8520   -0.2489 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1609   -2.1764   -1.4912 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8508   -2.5833   -2.4604 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2049   -2.0157   -1.4883 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7939    1.1992   -1.3818 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6219    0.9307    0.9351 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4525    2.3258    0.7687 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6549    0.7403    1.9868 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4129   -0.5379    1.9319 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.8147   -1.6213    2.8041 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3012    0.5480   -2.1487 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1319    1.1905   -0.9742 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6593   -0.1112   -2.1823 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8869   -1.1814   -0.6489 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5324   -2.9224    0.6706 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9169   -3.3488    1.2640 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9743   -2.1307    2.1653 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0755   -1.9637    0.3554 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0880   -1.5257    0.3994 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8270   -1.6734   -1.2293 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2366   -0.2852   -0.3866 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8475   -0.3308   -2.9431 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0785    0.2159   -2.9251 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9076    1.5681   -0.8080 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2749    2.7853   -3.1204 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5862    2.3696   -3.4782 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1829    4.7230   -2.2080 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3337    5.6633   -0.1520 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0764    4.8521    0.5372 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5036    4.3186    1.1162 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2335    2.1900    0.0675 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1966    2.1618   -1.7858 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4946    4.3194   -1.6930 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7705    3.5616    1.2580 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6168    5.2047    0.4093 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1098    4.2626    0.3340 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6692    2.3872   -2.5004 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5334    1.8989   -0.9428 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6600    1.3040    1.4433 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6281    0.8059    2.5313 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2743    0.2904    1.5339 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3082   -1.1805    2.9409 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2155   -0.3136   -2.4642 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1561   -0.7490   -0.7075 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4587   -1.8246   -1.9302 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4545   -3.3617   -0.5455 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0830   -2.3721    2.2000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7119   -3.8777    1.3483 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3224   -2.4411    0.4032 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6476   -4.9704    2.0421 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8848   -5.2875    0.7063 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1623   -5.6028    0.4486 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5512   -3.8041    0.6114 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2342   -1.4099    0.4637 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6514    0.5502    1.2937 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3133    2.7875    0.7273 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3547    1.6083    1.9753 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1533    0.7892    2.9956 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4338   -0.3303    2.3701 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7724   -1.3787    3.1138 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4497   -1.8706    3.6784 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8076   -2.5610    2.1811 H   0  0  0  0  0  0  0  0  0  0  0  0
 30 29  1  0
 29 28  1  0
 28 27  1  0
 27 25  1  0
 25 26  1  6
 25 34  1  0
 34 33  1  0
 33 31  2  0
 31 32  1  0
 34 35  1  0
 35 36  2  0
 35 37  1  0
 37  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  1  0
 11 38  1  0
  7 38  1  6
  7  8  1  0
  7  6  1  0
  6  5  1  0
  5 42  1  0
 42 43  1  0
 42 41  1  0
 41 39  1  0
 39 40  1  0
  5  3  1  0
  3  4  1  0
  3  2  2  0
  2  1  1  0
 31 28  1  0
  8  9  1  0
 22 25  1  0
 39  7  1  0
 30 80  1  0
 30 81  1  0
 30 82  1  0
 28 79  1  6
 27 77  1  0
 27 78  1  0
 26 76  1  0
 34 87  1  1
 33 86  1  0
 32 83  1  0
 32 84  1  0
 32 85  1  0
  9 54  1  1
 10 55  1  0
 10 56  1  0
 11 57  1  1
 12 58  1  0
 12 59  1  0
 13 60  1  0
 15 61  1  0
 15 62  1  0
 15 63  1  0
 16 64  1  0
 16 65  1  0
 17 66  1  6
 18 67  1  0
 18 68  1  0
 18 69  1  0
 19 70  1  0
 20 71  1  0
 21 72  1  0
 23 73  1  0
 23 74  1  0
 24 75  1  0
  8 52  1  0
  8 53  1  0
  5 51  1  6
 42 92  1  1
 43 93  1  0
 43 94  1  0
 43 95  1  0
 41 90  1  0
 41 91  1  0
 39 88  1  1
 40 89  1  0
  4 48  1  0
  4 49  1  0
  4 50  1  0
  2 47  1  0
  1 44  1  0
  1 45  1  0
  1 46  1  0
M  END


  Mrv1533004161503342D          

 43 46  0  0  0  0            999 V2000
    7.8306    2.5672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0544    2.2878    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4242    2.8203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5703    3.6322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9402    4.1647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7164    4.4442    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1640    3.8853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8688    2.7566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6480    2.5408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5019    1.7289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0179    3.0733    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2147    2.2721    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2417    2.7939    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6115    3.3264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7576    4.1384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1275    4.6709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2736    5.4828    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6435    6.0153    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7896    6.8273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1595    7.3598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5658    7.1067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1959    6.5742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0498    5.7623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9722    6.8537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6023    6.3212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4562    5.5092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0863    4.9767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8625    5.2562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0087    6.0681    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3513    4.3914    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2052    3.5795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8353    3.0469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0591    2.7675    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2828    2.4880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6527    3.0205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1235    2.7411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7988    3.8325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5750    4.1120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7211    4.9239    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1367    1.6761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3605    1.3966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2144    0.5847    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7669    1.1436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  3  9  1  0  0  0  0
  9 10  1  0  0  0  0
  7 11  1  0  0  0  0
 11 12  2  0  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  1  0  0  0  0
 16 17  1  0  0  0  0
 18 17  1  4  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 24 22  1  4  0  0  0
 24 25  2  0  0  0  0
 26 25  1  4  0  0  0
 26 27  2  0  0  0  0
  5 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 16 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 14 32  1  0  0  0  0
 31 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 35 37  1  0  0  0  0
 37 38  1  0  0  0  0
 31 38  1  0  0  0  0
 38 39  1  0  0  0  0
 34 40  1  0  0  0  0
 40 41  2  0  0  0  0
 41 42  1  4  0  0  0
 40 43  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0301107

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1CC2(O)C(C=C1C)C(=O)OC1CC(CC=C(C)CC(C)C=CC=C2CO)OC2(C1)OC(C(C)CC2O)C(C)=CC

> <INCHI_IDENTIFIER>
InChI=1S/C35H52O8/c1-8-23(4)32-25(6)16-31(37)35(43-32)18-28-17-27(42-35)13-12-22(3)14-21(2)10-9-11-26(20-36)34(39)19-30(40-7)24(5)15-29(34)33(38)41-28/h8-12,15,21,25,27-32,36-37,39H,13-14,16-20H2,1-7H3

> <INCHI_KEY>
RZZQRUATDNDCKY-UHFFFAOYSA-N

> <FORMULA>
C35H52O8

> <MOLECULAR_WEIGHT>
600.793

> <EXACT_MASS>
600.366218634

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
95

> <JCHEM_AVERAGE_POLARIZABILITY>
66.36258419871882

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
6-(but-2-en-2-yl)-3,9'-dihydroxy-10'-(hydroxymethyl)-7'-methoxy-5,6',14',16'-tetramethyl-2',20'-dioxaspiro[oxane-2,21'-tricyclo[17.3.1.0⁴,⁹]tricosane]-5',10',12',16'-tetraen-3'-one

> <ALOGPS_LOGP>
4.95

> <JCHEM_LOGP>
4.336814937333335

> <ALOGPS_LOGS>
-4.75

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.675174989537261

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.040610815870107

> <JCHEM_PKA_STRONGEST_BASIC>
-2.7710049663174017

> <JCHEM_POLAR_SURFACE_AREA>
114.68000000000002

> <JCHEM_REFRACTIVITY>
169.85720000000006

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.07e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6-(but-2-en-2-yl)-3,9'-dihydroxy-10'-(hydroxymethyl)-7'-methoxy-5,6',14',16'-tetramethyl-2',20'-dioxaspiro[oxane-2,21'-tricyclo[17.3.1.0⁴,⁹]tricosane]-5',10',12',16'-tetraen-3'-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 16-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   16-APR-15         0                                  
HETATM    1  C   UNK     0      14.617   4.792   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      13.168   4.270   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      11.992   5.265   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      12.265   6.780   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      11.088   7.774   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      12.537   8.296   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       9.639   7.253   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.089   5.146   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      10.543   4.743   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      10.270   3.227   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.367   5.737   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       9.734   4.241   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       7.918   5.215   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       6.742   6.209   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.014   7.725   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.838   8.719   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.111  10.235   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.934  11.229   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.207  12.744   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.031  13.738   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.656  13.266   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       7.832  12.272   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       7.560  10.756   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       9.281  12.794   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      10.458  11.800   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      10.185  10.284   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      11.361   9.290   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      12.810   9.811   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      13.083  11.327   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0       4.389   8.197   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       4.116   6.682   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       5.293   5.688   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       3.844   5.166   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       2.395   4.644   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       1.218   5.638   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -0.231   5.117   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       1.491   7.154   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       2.940   7.676   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0       3.213   9.191   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0       2.122   3.129   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0       0.673   2.607   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0       0.400   1.091   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0       3.298   2.135   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    9                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    7   27                                             
CONECT    6    5                                                            
CONECT    7    5    8   11                                                  
CONECT    8    7    9                                                       
CONECT    9    8    3   10                                                  
CONECT   10    9                                                            
CONECT   11    7   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13   15   32                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   30                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26    5   28                                                  
CONECT   28   27   29                                                       
CONECT   29   28                                                            
CONECT   30   16   31                                                       
CONECT   31   30   32   33   38                                             
CONECT   32   31   14                                                       
CONECT   33   31   34                                                       
CONECT   34   33   35   40                                                  
CONECT   35   34   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35   38                                                       
CONECT   38   37   31   39                                                  
CONECT   39   38                                                            
CONECT   40   34   41   43                                                  
CONECT   41   40   42                                                       
CONECT   42   41                                                            
CONECT   43   40                                                            
MASTER        0    0    0    0    0    0    0    0   43    0   92    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₅H₅₂O₈

Average Mass

600.7930 Da

Monoisotopic Mass

600.36622 Da

IUPAC Name

6-(but-2-en-2-yl)-3,9'-dihydroxy-10'-(hydroxymethyl)-7'-methoxy-5,6',14',16'-tetramethyl-2',20'-dioxaspiro[oxane-2,21'-tricyclo[17.3.1.0⁴,⁹]tricosane]-5',10',12',16'-tetraen-3'-one

Traditional Name

6-(but-2-en-2-yl)-3,9'-dihydroxy-10'-(hydroxymethyl)-7'-methoxy-5,6',14',16'-tetramethyl-2',20'-dioxaspiro[oxane-2,21'-tricyclo[17.3.1.0⁴,⁹]tricosane]-5',10',12',16'-tetraen-3'-one

CAS Registry Number

Not Available

SMILES

COC1CC2(O)C(C=C1C)C(=O)OC1CC(CC=C(C)CC(C)C=CC=C2CO)OC2(C1)OC(C(C)CC2O)C(C)=CC

InChI Identifier

InChI=1S/C35H52O8/c1-8-23(4)32-25(6)16-31(37)35(43-32)18-28-17-27(42-35)13-12-22(3)14-21(2)10-9-11-26(20-36)34(39)19-30(40-7)24(5)15-29(34)33(38)41-28/h8-12,15,21,25,27-32,36-37,39H,13-14,16-20H2,1-7H3

InChI Key

RZZQRUATDNDCKY-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as milbemycins. These are a group of macrolides with a structure containing a 16-membered lactone ring fused to a 1,7-dioxaspiroundecane ring system and to either a benzofuran (or hydrogenated derivative thereof). In some cases (e.G. Milbemycin E), the tetrahydrofuranyl ring is missing. Milbemycins can be o-glycosylated at C13 to form Avermectins. Milbemycins are produced by Streptomyces species.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Macrolides and analogues

Sub Class

Milbemycins

Direct Parent

Milbemycins

Alternative Parents

Substituents

Milbemycin
Ketal
Oxane
Tertiary alcohol
Carboxylic acid ester
Lactone
Secondary alcohol
Acetal
Carboxylic acid derivative
Dialkyl ether
Ether
Monocarboxylic acid or derivatives
Oxacycle
Organoheterocyclic compound
Carbonyl group
Organic oxide
Hydrocarbon derivative
Alcohol
Organooxygen compound
Organic oxygen compound
Primary alcohol
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	4.95	ALOGPS
logP	4.34	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Acidic)	13.04	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	114.68 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	169.86 m³·mol⁻¹	ChemAxon
Polarizability	66.36 Å³	ChemAxon
Number of Rings	4	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

85237097

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 6-(but-2-en-2-yl)-3,9'-dihydroxy-10'-(hydroxymethyl)-7'-methoxy-5,6',14',16'-tetramethyl-2',20'-dioxaspiro[oxane-2,21'-tricyclo[17.3.1.0⁴,⁹]tricosane]-5',10',12',16'-tetraen-3'-one (NP0301107)

MOL for NP0301107 (6-(but-2-en-2-yl)-3,9'-dihydroxy-10'-(hydroxymethyl)-7'-methoxy-5,6',14',16'-tetramethyl-2',20'-dioxaspiro[oxane-2,21'-tricyclo[17.3.1.0⁴,⁹]tricosane]-5',10',12',16'-tetraen-3'-one)

3D MOL for NP0301107 (6-(but-2-en-2-yl)-3,9'-dihydroxy-10'-(hydroxymethyl)-7'-methoxy-5,6',14',16'-tetramethyl-2',20'-dioxaspiro[oxane-2,21'-tricyclo[17.3.1.0⁴,⁹]tricosane]-5',10',12',16'-tetraen-3'-one)

3D SDF for NP0301107 (6-(but-2-en-2-yl)-3,9'-dihydroxy-10'-(hydroxymethyl)-7'-methoxy-5,6',14',16'-tetramethyl-2',20'-dioxaspiro[oxane-2,21'-tricyclo[17.3.1.0⁴,⁹]tricosane]-5',10',12',16'-tetraen-3'-one)

3D-SDF for NP0301107 (6-(but-2-en-2-yl)-3,9'-dihydroxy-10'-(hydroxymethyl)-7'-methoxy-5,6',14',16'-tetramethyl-2',20'-dioxaspiro[oxane-2,21'-tricyclo[17.3.1.0⁴,⁹]tricosane]-5',10',12',16'-tetraen-3'-one)

PDB for NP0301107 (6-(but-2-en-2-yl)-3,9'-dihydroxy-10'-(hydroxymethyl)-7'-methoxy-5,6',14',16'-tetramethyl-2',20'-dioxaspiro[oxane-2,21'-tricyclo[17.3.1.0⁴,⁹]tricosane]-5',10',12',16'-tetraen-3'-one)

3D PDB for NP0301107 (6-(but-2-en-2-yl)-3,9'-dihydroxy-10'-(hydroxymethyl)-7'-methoxy-5,6',14',16'-tetramethyl-2',20'-dioxaspiro[oxane-2,21'-tricyclo[17.3.1.0⁴,⁹]tricosane]-5',10',12',16'-tetraen-3'-one)

SMILES for NP0301107 (6-(but-2-en-2-yl)-3,9'-dihydroxy-10'-(hydroxymethyl)-7'-methoxy-5,6',14',16'-tetramethyl-2',20'-dioxaspiro[oxane-2,21'-tricyclo[17.3.1.0⁴,⁹]tricosane]-5',10',12',16'-tetraen-3'-one)

INCHI for NP0301107 (6-(but-2-en-2-yl)-3,9'-dihydroxy-10'-(hydroxymethyl)-7'-methoxy-5,6',14',16'-tetramethyl-2',20'-dioxaspiro[oxane-2,21'-tricyclo[17.3.1.0⁴,⁹]tricosane]-5',10',12',16'-tetraen-3'-one)

Structure for NP0301107 (6-(but-2-en-2-yl)-3,9'-dihydroxy-10'-(hydroxymethyl)-7'-methoxy-5,6',14',16'-tetramethyl-2',20'-dioxaspiro[oxane-2,21'-tricyclo[17.3.1.0⁴,⁹]tricosane]-5',10',12',16'-tetraen-3'-one)

3D Structure for NP0301107 (6-(but-2-en-2-yl)-3,9'-dihydroxy-10'-(hydroxymethyl)-7'-methoxy-5,6',14',16'-tetramethyl-2',20'-dioxaspiro[oxane-2,21'-tricyclo[17.3.1.0⁴,⁹]tricosane]-5',10',12',16'-tetraen-3'-one)