NP-MRD: Showing NP-Card for 6-(but-2-en-2-yl)-7',9'-dihydroxy-5,6',14',16'-tetramethyl-3'-oxo-2',20'-dioxaspiro[oxane-2,21'-tricyclo[17.3.1.0⁴,⁹]tricosane]-5',10',12',16'-tetraene-10'-carbaldehyde (NP0317366)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-11 17:13:04 UTC

Updated at

2022-09-11 17:13:04 UTC

NP-MRD ID

NP0317366

Secondary Accession Numbers

None

Natural Product Identification

Common Name

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

Description

6-(But-2-en-2-yl)-7',9'-dihydroxy-5,6',14',16'-tetramethyl-3'-oxo-2',20'-dioxaspiro[oxane-2,21'-tricyclo[17.3.1.0⁴,⁹]Tricosane]-5',10',12',16'-tetraene-10'-carbaldehyde 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)-7',9'-dihydroxy-5,6',14',16'-tetramethyl-3'-oxo-2',20'-dioxaspiro[oxane-2,21'-tricyclo[17.3.1.0⁴,⁹]Tricosane]-5',10',12',16'-tetraene-10'-carbaldehyde is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 04121517372D          

 41 44  0  0  0  0            999 V2000
   10.6929   -1.4752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7607   -2.2974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0826   -2.7672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1504   -3.5895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3366   -2.4149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6584   -2.8847    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9125   -2.5323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8447   -1.7101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5228   -1.2403    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2688   -1.5927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9469   -1.1228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1665   -2.1800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4884   -2.6498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5562   -3.4720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3022   -3.8244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3700   -4.6466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6918   -5.1164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9459   -4.7640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8781   -3.9418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2677   -5.2339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5218   -4.8815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4539   -4.0593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8436   -5.3513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0977   -4.9990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0298   -4.1767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7080   -3.7069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9620   -3.3545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2839   -3.8244    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6402   -2.8847    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8154   -2.8662    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8942   -2.5323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8264   -1.7101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0804   -1.3578    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5045   -1.2403    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2505   -1.5927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3183   -2.4149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0643   -2.7672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1321   -3.5895    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7424   -2.2974    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4367   -0.4181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9803   -3.3545    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  4  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  5 10  1  0  0  0  0
 10 11  1  0  0  0  0
  7 12  1  0  0  0  0
 12 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
 17 16  1  4  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 23 21  1  4  0  0  0
 23 24  2  0  0  0  0
 25 24  1  4  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 26 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 32 34  1  0  0  0  0
 34 35  2  0  0  0  0
 35 36  1  0  0  0  0
 29 36  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  2  0  0  0  0
 37 39  1  0  0  0  0
 13 39  1  0  0  0  0
 34 40  1  0  0  0  0
 15 41  1  0  0  0  0
  7 41  1  0  0  0  0
M  END

     RDKit          3D

 89 92  0  0  0  0  0  0  0  0999 V2000
    5.0236    3.8587    0.2622 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3071    3.1198    1.5088 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1476    1.8050    1.6280 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4590    1.1417    2.9275 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6636    1.0623    0.4506 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4896    0.4199    0.8353 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7538   -0.0729   -0.2433 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6277   -0.1164   -1.5055 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9542   -0.7239   -1.1717 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6235    0.0004   -0.0217 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.9119    0.5829   -0.5537 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6585    0.9041   -0.5132 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6019    0.7437    0.5538 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1186   -0.6765    0.3974 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2720   -1.5912    0.7356 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8639   -3.0489    0.5621 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2780   -3.2201   -0.3405 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3855   -3.9390   -0.1172 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0334   -4.6379   -1.3016 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0353   -4.1344    1.1699 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2192   -3.2428    1.4861 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.9924   -2.9755    0.2649 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8411   -2.0867    2.3171 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2541   -0.8773    2.4081 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4073   -0.1306    1.9726 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7878    0.2978    0.7912 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2259    0.0591    0.4706 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6412    0.4404   -0.6426 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0420    0.9949   -0.2587 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.5142    0.4149   -1.4778 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4420    2.4468   -0.3856 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0535    2.9914   -1.7061 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.9054    4.3837   -1.5498 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8471    2.3785   -2.2550 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3741    2.9183   -3.6039 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1862    1.4283   -1.6629 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5644    0.8152   -0.3204 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7625    1.5762    0.6524 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3470    2.1169    1.6196 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4251    1.6836    0.4929 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4110   -1.3537    0.0561 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5952    3.4793   -0.6046 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2747    4.9251    0.4208 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9261    3.8494    0.0229 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6632    3.6605    2.3772 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9413    0.1543    3.0058 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0734    1.7499    3.7688 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5577    1.0478    3.0918 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5076    1.7694   -0.3789 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1026   -0.8111   -2.2061 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6803    0.8515   -2.0018 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5735   -0.7095   -2.1001 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8088   -1.8004   -0.9324 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8334   -0.6846    0.8028 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7306    1.4567   -1.2172 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4324   -0.1669   -1.1861 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6309    0.8259    0.2692 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1745    0.6474   -1.4906 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0707    1.9198   -0.5577 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1249    0.8590    1.5412 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6934   -0.8003    1.1293 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1478   -0.8433   -0.6454 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4652   -1.4491    1.8172 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7137   -3.5532    1.5471 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7273   -3.6135    0.0991 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2598   -2.7231   -1.3274 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6786   -5.4584   -0.9730 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6003   -3.9262   -1.9286 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2676   -5.0817   -1.9760 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3046   -5.2133    1.2853 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2638   -3.8880    1.9603 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8632   -3.8817    2.1758 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9872   -2.5384    0.5946 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5608   -2.2865   -0.4743 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3057   -3.8887   -0.2783 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9947   -2.4206    2.9997 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5460   -0.2151    3.0007 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1704    0.1898    2.7597 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9187   -0.4096    1.1194 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8006    0.1170   -2.0573 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1099    3.0805    0.4576 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5618    2.4710   -0.3225 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8786    2.7831   -2.4464 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6370    4.7285   -0.9611 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5365    2.3091   -3.9439 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2060    3.0310   -4.2971 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9824    3.9355   -3.3649 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2989    1.0160   -2.1219 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3567   -0.2509   -0.3841 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
  3  5  1  0
  5  6  1  0
  7  6  1  1
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
  7 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 21 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 26 29  1  0
 29 30  1  6
 29 31  1  0
 31 32  1  0
 32 33  1  0
 32 34  1  0
 34 35  1  0
 34 36  2  0
 36 37  1  0
 37 38  1  0
 38 39  2  0
 38 40  1  0
 15 41  1  0
 10  5  1  0
 40 13  1  0
 41  7  1  0
 37 29  1  0
  1 42  1  0
  1 43  1  0
  1 44  1  0
  2 45  1  0
  4 46  1  0
  4 47  1  0
  4 48  1  0
  5 49  1  6
  8 50  1  0
  8 51  1  0
  9 52  1  0
  9 53  1  0
 10 54  1  1
 11 55  1  0
 11 56  1  0
 11 57  1  0
 12 58  1  0
 12 59  1  0
 13 60  1  1
 14 61  1  0
 14 62  1  0
 15 63  1  1
 16 64  1  0
 16 65  1  0
 17 66  1  0
 19 67  1  0
 19 68  1  0
 19 69  1  0
 20 70  1  0
 20 71  1  0
 21 72  1  1
 22 73  1  0
 22 74  1  0
 22 75  1  0
 23 76  1  0
 24 77  1  0
 25 78  1  0
 27 79  1  0
 30 80  1  0
 31 81  1  0
 31 82  1  0
 32 83  1  6
 33 84  1  0
 35 85  1  0
 35 86  1  0
 35 87  1  0
 36 88  1  0
 37 89  1  6
M  END


  Mrv0541 04121517372D          

 41 44  0  0  0  0            999 V2000
   10.6929   -1.4752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7607   -2.2974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0826   -2.7672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1504   -3.5895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3366   -2.4149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6584   -2.8847    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9125   -2.5323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8447   -1.7101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5228   -1.2403    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2688   -1.5927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9469   -1.1228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1665   -2.1800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4884   -2.6498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5562   -3.4720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3022   -3.8244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3700   -4.6466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6918   -5.1164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9459   -4.7640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8781   -3.9418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2677   -5.2339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5218   -4.8815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4539   -4.0593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8436   -5.3513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0977   -4.9990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0298   -4.1767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7080   -3.7069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9620   -3.3545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2839   -3.8244    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6402   -2.8847    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8154   -2.8662    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8942   -2.5323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8264   -1.7101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0804   -1.3578    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5045   -1.2403    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2505   -1.5927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3183   -2.4149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0643   -2.7672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1321   -3.5895    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7424   -2.2974    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4367   -0.4181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9803   -3.3545    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  4  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  5 10  1  0  0  0  0
 10 11  1  0  0  0  0
  7 12  1  0  0  0  0
 12 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
 17 16  1  4  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 23 21  1  4  0  0  0
 23 24  2  0  0  0  0
 25 24  1  4  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 26 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 32 34  1  0  0  0  0
 34 35  2  0  0  0  0
 35 36  1  0  0  0  0
 29 36  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  2  0  0  0  0
 37 39  1  0  0  0  0
 13 39  1  0  0  0  0
 34 40  1  0  0  0  0
 15 41  1  0  0  0  0
  7 41  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0317366

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC=C(C)C1OC2(CCC1C)CC1CC(CC=C(C)CC(C)C=CC=C(C=O)C3(O)CC(O)C(C)=CC3C(=O)O1)O2

> <INCHI_IDENTIFIER>
InChI=1S/C34H48O7/c1-7-23(4)31-24(5)13-14-33(41-31)18-28-17-27(40-33)12-11-22(3)15-21(2)9-8-10-26(20-35)34(38)19-30(36)25(6)16-29(34)32(37)39-28/h7-11,16,20-21,24,27-31,36,38H,12-15,17-19H2,1-6H3

> <INCHI_KEY>
CHCOJVIDIGKSLY-UHFFFAOYSA-N

> <FORMULA>
C34H48O7

> <MOLECULAR_WEIGHT>
568.751

> <EXACT_MASS>
568.340003886

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
89

> <JCHEM_AVERAGE_POLARIZABILITY>
63.25459956256593

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
5.28

> <JCHEM_LOGP>
4.853738078000001

> <ALOGPS_LOGS>
-5.06

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.6470960948119

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.333445503706859

> <JCHEM_PKA_STRONGEST_BASIC>
-3.0113736036453407

> <JCHEM_POLAR_SURFACE_AREA>
102.29000000000002

> <JCHEM_REFRACTIVITY>
162.872

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.95e-03 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 12-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-APR-15         0                                  
HETATM    1  C   UNK     0      19.960  -2.754   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      20.087  -4.289   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      18.821  -5.166   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      18.947  -6.700   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      17.428  -4.508   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      16.162  -5.385   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      14.770  -4.727   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      14.643  -3.192   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      15.909  -2.315   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      17.302  -2.973   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      18.568  -2.096   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      13.378  -4.069   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      12.112  -4.946   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      12.238  -6.481   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      13.631  -7.139   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      13.757  -8.674   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      12.491  -9.551   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      11.099  -8.893   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      10.972  -7.358   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       9.833  -9.770   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       8.441  -9.112   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       8.314  -7.577   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       7.175  -9.989   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       5.782  -9.331   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       5.656  -7.797   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       6.922  -6.920   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       5.529  -6.262   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       4.263  -7.139   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       6.795  -5.385   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       5.255  -5.350   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       5.403  -4.727   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       5.276  -3.192   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       3.883  -2.534   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       6.542  -2.315   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       7.934  -2.973   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       8.061  -4.508   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       9.453  -5.166   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0       9.580  -6.700   0.000  0.00  0.00           O+0
HETATM   39  O   UNK     0      10.719  -4.289   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0       6.415  -0.780   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0      14.897  -6.262   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   10                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   12   41                                             
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9    5   11                                                  
CONECT   11   10                                                            
CONECT   12    7   13                                                       
CONECT   13   12   14   39                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   41                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27   29                                                  
CONECT   27   26   28                                                       
CONECT   28   27                                                            
CONECT   29   26   30   31   36                                             
CONECT   30   29                                                            
CONECT   31   29   32                                                       
CONECT   32   31   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32   35   40                                                  
CONECT   35   34   36                                                       
CONECT   36   35   29   37                                                  
CONECT   37   36   38   39                                                  
CONECT   38   37                                                            
CONECT   39   37   13                                                       
CONECT   40   34                                                            
CONECT   41   15    7                                                       
MASTER        0    0    0    0    0    0    0    0   41    0   88    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₄H₄₈O₇

Average Mass

568.7510 Da

Monoisotopic Mass

568.34000 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

CC=C(C)C1OC2(CCC1C)CC1CC(CC=C(C)CC(C)C=CC=C(C=O)C3(O)CC(O)C(C)=CC3C(=O)O1)O2

InChI Identifier

InChI=1S/C34H48O7/c1-7-23(4)31-24(5)13-14-33(41-31)18-28-17-27(40-33)12-11-22(3)15-21(2)9-8-10-26(20-35)34(38)19-30(36)25(6)16-29(34)32(37)39-28/h7-11,16,20-21,24,27-31,36,38H,12-15,17-19H2,1-6H3

InChI Key

CHCOJVIDIGKSLY-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
Monocarboxylic acid or derivatives
Oxacycle
Organoheterocyclic compound
Organic oxide
Organic oxygen compound
Alcohol
Hydrocarbon derivative
Aldehyde
Organooxygen compound
Carbonyl group
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	5.28	ALOGPS
logP	4.85	ChemAxon
logS	-5.1	ALOGPS
pKa (Strongest Acidic)	13.33	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	102.29 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	162.87 m³·mol⁻¹	ChemAxon
Polarizability	63.25 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

85149185

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)-7',9'-dihydroxy-5,6',14',16'-tetramethyl-3'-oxo-2',20'-dioxaspiro[oxane-2,21'-tricyclo[17.3.1.0⁴,⁹]tricosane]-5',10',12',16'-tetraene-10'-carbaldehyde (NP0317366)

MOL for NP0317366 (6-(but-2-en-2-yl)-7',9'-dihydroxy-5,6',14',16'-tetramethyl-3'-oxo-2',20'-dioxaspiro[oxane-2,21'-tricyclo[17.3.1.0⁴,⁹]tricosane]-5',10',12',16'-tetraene-10'-carbaldehyde)

3D MOL for NP0317366 (6-(but-2-en-2-yl)-7',9'-dihydroxy-5,6',14',16'-tetramethyl-3'-oxo-2',20'-dioxaspiro[oxane-2,21'-tricyclo[17.3.1.0⁴,⁹]tricosane]-5',10',12',16'-tetraene-10'-carbaldehyde)

3D SDF for NP0317366 (6-(but-2-en-2-yl)-7',9'-dihydroxy-5,6',14',16'-tetramethyl-3'-oxo-2',20'-dioxaspiro[oxane-2,21'-tricyclo[17.3.1.0⁴,⁹]tricosane]-5',10',12',16'-tetraene-10'-carbaldehyde)

3D-SDF for NP0317366 (6-(but-2-en-2-yl)-7',9'-dihydroxy-5,6',14',16'-tetramethyl-3'-oxo-2',20'-dioxaspiro[oxane-2,21'-tricyclo[17.3.1.0⁴,⁹]tricosane]-5',10',12',16'-tetraene-10'-carbaldehyde)

PDB for NP0317366 (6-(but-2-en-2-yl)-7',9'-dihydroxy-5,6',14',16'-tetramethyl-3'-oxo-2',20'-dioxaspiro[oxane-2,21'-tricyclo[17.3.1.0⁴,⁹]tricosane]-5',10',12',16'-tetraene-10'-carbaldehyde)

3D PDB for NP0317366 (6-(but-2-en-2-yl)-7',9'-dihydroxy-5,6',14',16'-tetramethyl-3'-oxo-2',20'-dioxaspiro[oxane-2,21'-tricyclo[17.3.1.0⁴,⁹]tricosane]-5',10',12',16'-tetraene-10'-carbaldehyde)

SMILES for NP0317366 (6-(but-2-en-2-yl)-7',9'-dihydroxy-5,6',14',16'-tetramethyl-3'-oxo-2',20'-dioxaspiro[oxane-2,21'-tricyclo[17.3.1.0⁴,⁹]tricosane]-5',10',12',16'-tetraene-10'-carbaldehyde)

INCHI for NP0317366 (6-(but-2-en-2-yl)-7',9'-dihydroxy-5,6',14',16'-tetramethyl-3'-oxo-2',20'-dioxaspiro[oxane-2,21'-tricyclo[17.3.1.0⁴,⁹]tricosane]-5',10',12',16'-tetraene-10'-carbaldehyde)

Structure for NP0317366 (6-(but-2-en-2-yl)-7',9'-dihydroxy-5,6',14',16'-tetramethyl-3'-oxo-2',20'-dioxaspiro[oxane-2,21'-tricyclo[17.3.1.0⁴,⁹]tricosane]-5',10',12',16'-tetraene-10'-carbaldehyde)

3D Structure for NP0317366 (6-(but-2-en-2-yl)-7',9'-dihydroxy-5,6',14',16'-tetramethyl-3'-oxo-2',20'-dioxaspiro[oxane-2,21'-tricyclo[17.3.1.0⁴,⁹]tricosane]-5',10',12',16'-tetraene-10'-carbaldehyde)