NP-MRD: Showing NP-Card for (2r,5s,6r,10'e,12'e,14'r,16'e,19'r)-7'-hydroxy-5,6,6',10',14',16'-hexamethyl-2',20'-dioxaspiro[oxane-2,21'-tricyclo[17.3.1.0⁴,⁹]tricosane]-4',6',8',10',12',16'-hexaen-3'-one (NP0229852)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-06 10:05:39 UTC

Updated at

2022-09-06 10:05:39 UTC

NP-MRD ID

NP0229852

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2r,5s,6r,10'e,12'e,14'r,16'e,19'r)-7'-hydroxy-5,6,6',10',14',16'-hexamethyl-2',20'-dioxaspiro[oxane-2,21'-tricyclo[17.3.1.0⁴,⁹]tricosane]-4',6',8',10',12',16'-hexaen-3'-one

Description

Milbemycin beta3, also known as milbemycin ALPHA14 or milbeknock, 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. (2r,5s,6r,10'e,12'e,14'r,16'e,19'r)-7'-hydroxy-5,6,6',10',14',16'-hexamethyl-2',20'-dioxaspiro[oxane-2,21'-tricyclo[17.3.1.0⁴,⁹]tricosane]-4',6',8',10',12',16'-hexaen-3'-one is found in Streptomyces hygroscopicus. (2r,5s,6r,10'e,12'e,14'r,16'e,19'r)-7'-hydroxy-5,6,6',10',14',16'-hexamethyl-2',20'-dioxaspiro[oxane-2,21'-tricyclo[17.3.1.0⁴,⁹]tricosane]-4',6',8',10',12',16'-hexaen-3'-one was first documented in 2006 (PMID: 16928055). Based on a literature review a small amount of articles have been published on milbemycin beta3 (PMID: 27589571) (PMID: 27246617) (PMID: 26328934).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309062212052D          

 36 39  0  0  1  0            999 V2000
    7.5203    2.9790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8166    3.7489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6316    3.8772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1502    3.2356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8538    2.4657    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.0389    2.3373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7425    1.5674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2611    0.9258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0761    1.0541    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.8911    1.1824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4097    0.5408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1133   -0.2291    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.6319   -0.8707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2984   -0.3574    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.0020   -1.1274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7797    0.2842    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.3724    1.8241    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9276    1.4391    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6312    0.6691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1498    0.0275    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8163    0.5408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5199   -0.2291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7049   -0.3574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4086   -1.1274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1863    0.2842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3714    0.1559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4827    1.0541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2976    1.1824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5940    1.9524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4090    2.0807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0754    2.5940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3717    3.3639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1867    3.4922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4830    4.2622    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.9644    4.9038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2980    4.3905    0.0000 C   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  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
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  6  0  0  0
 12 14  1  0  0  0  0
 14 15  1  1  0  0  0
 14 16  1  0  0  0  0
  9 16  1  6  0  0  0
  9 17  1  0  0  0  0
  5 17  1  1  0  0  0
  7 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  2  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 27 28  2  0  0  0  0
 21 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  2  0  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  6  0  0  0
 34 36  1  0  0  0  0
  2 36  1  0  0  0  0
M  END

     RDKit          3D

 78 81  0  0  0  0  0  0  0  0999 V2000
   -0.1160    4.7543    1.4733 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3432    3.9405    0.2895 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0639    2.8591    0.4156 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1049    2.3628   -0.5212 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1695    0.8326   -0.4698 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1149    0.2167   -1.3231 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1058   -0.5276   -0.4797 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7949   -1.4427    0.4997 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1957   -0.9761    0.8423 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5698   -1.5401    2.1758 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3492   -2.8364    2.0397 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5979   -2.5517    1.2736 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.7015   -2.0643    2.2199 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3652   -1.5092    0.2218 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.1379   -1.9524   -1.0274 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0572   -1.3517   -0.1603 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1363    0.4255    0.8589 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7700    0.3992    0.1347 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8672    0.0618    0.9216 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9657    0.5963    2.0582 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9283   -0.8752    0.5335 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1602   -1.9102    1.4515 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0571   -2.9323    1.2379 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2836   -4.0169    2.2220 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7606   -2.9273    0.0528 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6759   -3.9476   -0.1990 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5371   -1.9165   -0.8421 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6240   -0.8560   -0.6437 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5527    0.1949   -1.6808 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3032   -0.3396   -3.0782 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7140    1.4924   -1.5659 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2206    2.4695   -0.6446 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0932    3.1141   -0.5414 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3649    3.8943   -1.5454 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1284    3.1111   -2.8265 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0920    4.4739   -1.0340 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6826    5.5328    1.6276 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0579    5.2620    1.2577 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1690    4.1724    2.3906 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9163    2.2146    1.3048 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0015    2.6913   -1.5511 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1323    2.7015   -0.1926 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1596    0.5461   -0.9318 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5560    0.9541   -1.9304 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5345   -0.5069   -2.0787 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5334   -1.1797   -1.1465 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7780   -2.4705    0.1267 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1585   -1.4396    1.4294 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6811   -1.7710    2.8120 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1916   -0.8420    2.7851 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5231   -3.2425    3.0515 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7686   -3.5912    1.4850 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9689   -3.5197    0.8608 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5380   -1.7289    1.5724 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0366   -2.9059    2.8520 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3679   -1.1781    2.7853 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8556   -0.5447    0.5165 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1030   -3.0634   -1.1045 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2083   -1.6068   -0.9570 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6760   -1.4931   -1.9192 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6182   -1.9181    2.4146 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3656   -4.1471    2.4337 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7799   -4.9652    1.9346 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8001   -3.6937    3.1825 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7974   -4.6583    0.4923 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1076   -1.9602   -1.7792 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8885   -1.2657   -3.1697 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7175    0.3469   -3.8447 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2448   -0.5705   -3.2394 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4067    1.9719   -2.3601 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9608    2.7608    0.1556 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6027    3.0705    0.4576 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0021    4.7726   -1.8675 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4814    2.0728   -2.6966 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0108    3.0374   -2.9748 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5082    3.6121   -3.7277 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1054    5.5883   -1.0280 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7269    4.2293   -1.7684 H   0  0  0  0  0  0  0  0  0  0  0  0
 13 12  1  0
 12 11  1  0
 11 10  1  0
 10  9  1  0
  9  8  1  0
  8  7  1  0
  7  6  1  0
  6  5  1  0
  5  4  1  0
  4  3  1  0
  3  2  2  0
  2  1  1  0
  2 36  1  0
 36 34  1  0
 34 35  1  0
 34 33  1  0
 33 32  2  0
 32 31  1  0
 31 29  2  0
 29 30  1  0
 29 28  1  0
 28 27  2  0
 27 25  1  0
 25 26  1  0
 25 23  2  0
 23 24  1  0
 23 22  1  0
 22 21  2  0
 21 19  1  0
 19 20  2  0
 19 18  1  0
  5 17  1  0
  9 16  1  6
 16 14  1  0
 14 15  1  0
 14 12  1  0
 17  9  1  0
 18  7  1  0
 21 28  1  0
 13 54  1  0
 13 55  1  0
 13 56  1  0
 12 53  1  6
 11 51  1  0
 11 52  1  0
 10 49  1  0
 10 50  1  0
  8 47  1  0
  8 48  1  0
  7 46  1  6
  6 44  1  0
  6 45  1  0
  5 43  1  6
  4 41  1  0
  4 42  1  0
  3 40  1  0
  1 37  1  0
  1 38  1  0
  1 39  1  0
 36 77  1  0
 36 78  1  0
 34 73  1  6
 35 74  1  0
 35 75  1  0
 35 76  1  0
 33 72  1  0
 32 71  1  0
 31 70  1  0
 30 67  1  0
 30 68  1  0
 30 69  1  0
 27 66  1  0
 26 65  1  0
 24 62  1  0
 24 63  1  0
 24 64  1  0
 22 61  1  0
 14 57  1  1
 15 58  1  0
 15 59  1  0
 15 60  1  0
M  END


  Mrv1652309062212052D          

 36 39  0  0  1  0            999 V2000
    7.5203    2.9790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8166    3.7489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6316    3.8772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1502    3.2356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8538    2.4657    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.0389    2.3373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7425    1.5674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2611    0.9258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0761    1.0541    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.8911    1.1824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4097    0.5408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1133   -0.2291    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.6319   -0.8707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2984   -0.3574    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.0020   -1.1274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7797    0.2842    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.3724    1.8241    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9276    1.4391    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6312    0.6691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1498    0.0275    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8163    0.5408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5199   -0.2291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7049   -0.3574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4086   -1.1274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1863    0.2842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3714    0.1559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4827    1.0541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2976    1.1824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5940    1.9524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4090    2.0807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0754    2.5940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3717    3.3639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1867    3.4922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4830    4.2622    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.9644    4.9038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2980    4.3905    0.0000 C   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  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
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  6  0  0  0
 12 14  1  0  0  0  0
 14 15  1  1  0  0  0
 14 16  1  0  0  0  0
  9 16  1  6  0  0  0
  9 17  1  0  0  0  0
  5 17  1  1  0  0  0
  7 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  2  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 27 28  2  0  0  0  0
 21 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  2  0  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  6  0  0  0
 34 36  1  0  0  0  0
  2 36  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0229852

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H]1CC[C@]2(CC3C[C@@H](C\C=C(C)\C[C@@H](C)\C=C\C=C(C)\C4=CC(O)=C(C)C=C4C(=O)O3)O2)O[C@@H]1C

> <INCHI_IDENTIFIER>
InChI=1S/C31H42O5/c1-19-8-7-9-22(4)27-17-29(32)23(5)15-28(27)30(33)34-26-16-25(11-10-20(2)14-19)36-31(18-26)13-12-21(3)24(6)35-31/h7-10,15,17,19,21,24-26,32H,11-14,16,18H2,1-6H3/b8-7+,20-10+,22-9+/t19-,21-,24+,25+,26?,31-/m0/s1

> <INCHI_KEY>
PPMBESPRWFQXDF-KEMGXVBCSA-N

> <FORMULA>
C31H42O5

> <MOLECULAR_WEIGHT>
494.672

> <EXACT_MASS>
494.303224452

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
78

> <JCHEM_AVERAGE_POLARIZABILITY>
56.51817236750402

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R,5S,6R,10'E,12'E,14'R,16'E,19'R)-7'-hydroxy-5,6,6',10',14',16'-hexamethyl-2',20'-dioxaspiro[oxane-2,21'-tricyclo[17.3.1.0^{4,9}]tricosane]-4'(9'),5',7',10',12',16'-hexaen-3'-one

> <JCHEM_LOGP>
7.557445274000001

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.7733871631415

> <JCHEM_PKA_STRONGEST_BASIC>
-4.057800889969313

> <JCHEM_POLAR_SURFACE_AREA>
64.99000000000001

> <JCHEM_REFRACTIVITY>
146.449

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(2R,5S,6R,10'E,12'E,14'R,16'E,19'R)-7'-hydroxy-5,6,6',10',14',16'-hexamethyl-2',20'-dioxaspiro[oxane-2,21'-tricyclo[17.3.1.0^{4,9}]tricosane]-4'(9'),5',7',10',12',16'-hexaen-3'-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-22         0                                  
HETATM    1  C   UNK     0      14.038   5.561   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      14.591   6.998   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      16.112   7.237   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      17.080   6.040   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      16.527   4.603   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      15.006   4.363   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      14.453   2.926   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      15.421   1.728   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      16.942   1.968   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      18.463   2.207   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      19.431   1.010   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      18.878  -0.428   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      19.846  -1.625   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      17.357  -0.667   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      16.804  -2.104   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      16.389   0.530   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      17.495   3.405   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      12.931   2.686   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      12.378   1.249   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      13.346   0.051   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      10.857   1.010   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      10.304  -0.428   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       8.783  -0.667   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       8.229  -2.104   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       7.814   0.530   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       6.293   0.291   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       8.368   1.968   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       9.889   2.207   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      10.442   3.644   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      11.963   3.884   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       9.474   4.842   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      10.027   6.279   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      11.548   6.519   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      12.102   7.956   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      11.134   9.154   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      13.623   8.196   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   36                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   17                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   18                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   16   17                                             
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14    9                                                       
CONECT   17    9    5                                                       
CONECT   18    7   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22   28                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28                                                       
CONECT   28   27   21   29                                                  
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34    2                                                       
MASTER        0    0    0    0    0    0    0    0   36    0   78    0
END

View in JSmol

Synonyms

Value	Source
Milbemycin b3	Generator
Milbemycin β3	Generator
Milbeknock	MeSH
Milbemycin a3	MeSH
Milbemycin b	MeSH
Milbemycin alpha14	MeSH
Milbemycin alpha15	MeSH
Milbemycin alpha2	MeSH
Milbemycin alpha4	MeSH
Milbemycin beta1	MeSH
Milbemycin beta12	MeSH
5-Hydroxymilbemycin beta7	MeSH
Milbemectin	MeSH
Milbemycin D	MeSH
Milbemycin alpha10	MeSH
Milbemycin alpha11	MeSH
Milbemycin alpha5	MeSH
Milbemycin alpha9	MeSH
Milbemycins	MeSH
Moxidectin	MeSH
Milbemycin alpha1	MeSH
Milbemycin alpha13	MeSH
Milbemycin alpha7	MeSH
Milbemycin beta2	MeSH
Mixture OF milbemycins a3 and a4	MeSH
Cydectin	MeSH
Milbemycin a4	MeSH
Milbemycin alpha3	MeSH
Milbemycin alpha6	MeSH
Milbemycin alpha8	MeSH

Chemical Formula

C₃₁H₄₂O₅

Average Mass

494.6720 Da

Monoisotopic Mass

494.30322 Da

IUPAC Name

(2R,5S,6R,10'E,12'E,14'R,16'E,19'R)-7'-hydroxy-5,6,6',10',14',16'-hexamethyl-2',20'-dioxaspiro[oxane-2,21'-tricyclo[17.3.1.0^{4,9}]tricosane]-4'(9'),5',7',10',12',16'-hexaen-3'-one

Traditional Name

(2R,5S,6R,10'E,12'E,14'R,16'E,19'R)-7'-hydroxy-5,6,6',10',14',16'-hexamethyl-2',20'-dioxaspiro[oxane-2,21'-tricyclo[17.3.1.0^{4,9}]tricosane]-4'(9'),5',7',10',12',16'-hexaen-3'-one

CAS Registry Number

Not Available

SMILES

C[C@H]1CC[C@]2(CC3C[C@@H](C\C=C(C)\C[C@@H](C)\C=C\C=C(C)\C4=CC(O)=C(C)C=C4C(=O)O3)O2)O[C@@H]1C

InChI Identifier

InChI=1S/C31H42O5/c1-19-8-7-9-22(4)27-17-29(32)23(5)15-28(27)30(33)34-26-16-25(11-10-20(2)14-19)36-31(18-26)13-12-21(3)24(6)35-31/h7-10,15,17,19,21,24-26,32H,11-14,16,18H2,1-6H3/b8-7+,20-10+,22-9+/t19-,21-,24+,25+,26?,31-/m0/s1

InChI Key

PPMBESPRWFQXDF-KEMGXVBCSA-N

Experimental Spectra

Not Available

Predicted Spectra

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

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Streptomyces hygroscopicus	LOTUS Database	35616633

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
1-hydroxy-2-unsubstituted benzenoid
Ketal
Oxane
Benzenoid
Carboxylic acid ester
Lactone
Monocarboxylic acid or derivatives
Acetal
Carboxylic acid derivative
Organoheterocyclic compound
Oxacycle
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

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

Predicted Properties

Property	Value	Source
logP	7.56	ChemAxon
pKa (Strongest Acidic)	8.77	ChemAxon
pKa (Strongest Basic)	-4.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	64.99 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	146.45 m³·mol⁻¹	ChemAxon
Polarizability	56.52 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

57525122

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

71300428

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Li JS, Zhang H, Zhang SY, Wang HY, Zhang J, Chen AL, Wang JD, Xiang WS: New macrocyclic lactones with acaricidal and nematocidal activities from a genetically engineered strain Streptomyces bingchenggensis BCJ60. J Asian Nat Prod Res. 2017 Apr;19(4):339-346. doi: 10.1080/10286020.2016.1211641. Epub 2016 Sep 2. [PubMed:27589571 ]
Pan JJ, Wan X, Zhang SY, Huang J, Zhang H, Chen AL, Wang JD: Three new 16-membered macrolide compounds from a genetically engineered strain S. avermitilis MHJ1011. Bioorg Med Chem Lett. 2016 Jul 15;26(14):3376-3379. doi: 10.1016/j.bmcl.2016.04.033. Epub 2016 May 28. [PubMed:27246617 ]
Pan JJ, Wan X, Zhang H, Chen Z, Huang J, Yang B, Chen AL, Wang JD: Three new milbemycins from a genetically engineered strain S. avermitilis MHJ1011. J Antibiot (Tokyo). 2016 Feb;69(2):104-7. doi: 10.1038/ja.2015.90. Epub 2015 Sep 2. [PubMed:26328934 ]
Li M, O'Doherty GA: De novo asymmetric synthesis of milbemycin beta3 via an iterative asymmetric hydration approach. Org Lett. 2006 Aug 31;8(18):3987-90. doi: 10.1021/ol061439k. [PubMed:16928055 ]
LOTUS database [Link]

Showing NP-Card for (2r,5s,6r,10'e,12'e,14'r,16'e,19'r)-7'-hydroxy-5,6,6',10',14',16'-hexamethyl-2',20'-dioxaspiro[oxane-2,21'-tricyclo[17.3.1.0⁴,⁹]tricosane]-4',6',8',10',12',16'-hexaen-3'-one (NP0229852)

MOL for NP0229852 ((2r,5s,6r,10'e,12'e,14'r,16'e,19'r)-7'-hydroxy-5,6,6',10',14',16'-hexamethyl-2',20'-dioxaspiro[oxane-2,21'-tricyclo[17.3.1.0⁴,⁹]tricosane]-4',6',8',10',12',16'-hexaen-3'-one)

3D MOL for NP0229852 ((2r,5s,6r,10'e,12'e,14'r,16'e,19'r)-7'-hydroxy-5,6,6',10',14',16'-hexamethyl-2',20'-dioxaspiro[oxane-2,21'-tricyclo[17.3.1.0⁴,⁹]tricosane]-4',6',8',10',12',16'-hexaen-3'-one)

3D SDF for NP0229852 ((2r,5s,6r,10'e,12'e,14'r,16'e,19'r)-7'-hydroxy-5,6,6',10',14',16'-hexamethyl-2',20'-dioxaspiro[oxane-2,21'-tricyclo[17.3.1.0⁴,⁹]tricosane]-4',6',8',10',12',16'-hexaen-3'-one)

3D-SDF for NP0229852 ((2r,5s,6r,10'e,12'e,14'r,16'e,19'r)-7'-hydroxy-5,6,6',10',14',16'-hexamethyl-2',20'-dioxaspiro[oxane-2,21'-tricyclo[17.3.1.0⁴,⁹]tricosane]-4',6',8',10',12',16'-hexaen-3'-one)

PDB for NP0229852 ((2r,5s,6r,10'e,12'e,14'r,16'e,19'r)-7'-hydroxy-5,6,6',10',14',16'-hexamethyl-2',20'-dioxaspiro[oxane-2,21'-tricyclo[17.3.1.0⁴,⁹]tricosane]-4',6',8',10',12',16'-hexaen-3'-one)

3D PDB for NP0229852 ((2r,5s,6r,10'e,12'e,14'r,16'e,19'r)-7'-hydroxy-5,6,6',10',14',16'-hexamethyl-2',20'-dioxaspiro[oxane-2,21'-tricyclo[17.3.1.0⁴,⁹]tricosane]-4',6',8',10',12',16'-hexaen-3'-one)

SMILES for NP0229852 ((2r,5s,6r,10'e,12'e,14'r,16'e,19'r)-7'-hydroxy-5,6,6',10',14',16'-hexamethyl-2',20'-dioxaspiro[oxane-2,21'-tricyclo[17.3.1.0⁴,⁹]tricosane]-4',6',8',10',12',16'-hexaen-3'-one)

INCHI for NP0229852 ((2r,5s,6r,10'e,12'e,14'r,16'e,19'r)-7'-hydroxy-5,6,6',10',14',16'-hexamethyl-2',20'-dioxaspiro[oxane-2,21'-tricyclo[17.3.1.0⁴,⁹]tricosane]-4',6',8',10',12',16'-hexaen-3'-one)

Structure for NP0229852 ((2r,5s,6r,10'e,12'e,14'r,16'e,19'r)-7'-hydroxy-5,6,6',10',14',16'-hexamethyl-2',20'-dioxaspiro[oxane-2,21'-tricyclo[17.3.1.0⁴,⁹]tricosane]-4',6',8',10',12',16'-hexaen-3'-one)

3D Structure for NP0229852 ((2r,5s,6r,10'e,12'e,14'r,16'e,19'r)-7'-hydroxy-5,6,6',10',14',16'-hexamethyl-2',20'-dioxaspiro[oxane-2,21'-tricyclo[17.3.1.0⁴,⁹]tricosane]-4',6',8',10',12',16'-hexaen-3'-one)