NP-MRD: Showing NP-Card for 6-ethyl-21',24'-dihydroxy-5,11',13',22'-tetramethyl-3',7',19'-trioxaspiro[oxane-2,6'-tetracyclo[15.6.1.1⁴,⁸.0²⁰,²⁴]pentacosane]-10',14',16',22'-tetraen-2'-one (NP0230604)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-06 11:06:17 UTC

Updated at

2022-09-06 11:06:17 UTC

NP-MRD ID

NP0230604

Secondary Accession Numbers

None

Natural Product Identification

Common Name

6-ethyl-21',24'-dihydroxy-5,11',13',22'-tetramethyl-3',7',19'-trioxaspiro[oxane-2,6'-tetracyclo[15.6.1.1⁴,⁸.0²⁰,²⁴]pentacosane]-10',14',16',22'-tetraen-2'-one

Description

Milbemycin A4, also known as milbemycin ALPHA2 or milbemectin, 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-ethyl-21',24'-dihydroxy-5,11',13',22'-tetramethyl-3',7',19'-trioxaspiro[oxane-2,6'-tetracyclo[15.6.1.1⁴,⁸.0²⁰,²⁴]pentacosane]-10',14',16',22'-tetraen-2'-one is found in Streptomyces bingchenggensis. Milbemycin A4 is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004251510112D          

 39 43  0  0  0  0            999 V2000
   11.9087    0.7663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1444    0.4557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4933    0.9623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7290    0.6516    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0778    1.1582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1910    1.9754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9553    2.2861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6064    1.7795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3707    2.0901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4267    1.6648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6624    1.3542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5492    0.5370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2004    0.0304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0873   -0.7868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3230   -1.0974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2098   -1.9146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8610   -2.4212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4455   -2.2252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7944   -1.7187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0301   -2.0293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9075   -0.9015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2564   -0.3949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3695    0.4223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7184    0.9289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8955    0.8697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5849    1.6340    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2158    2.1656    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2429    2.9901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5423    3.4259    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9705    3.3789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6710    2.9432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5958    2.0567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2469    1.5502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1338    0.7330    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0112    1.8608    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8315    1.7461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9188    2.5665    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9976    4.2035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9647    0.3410    0.0000 O   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
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  3  8  1  0  0  0  0
  8  9  1  0  0  0  0
  5 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 15 14  1  4  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 21 19  1  4  0  0  0
 21 22  2  0  0  0  0
 23 22  1  4  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 28 30  1  0  0  0  0
 30 31  2  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 33 35  1  0  0  0  0
 11 35  1  0  0  0  0
 32 36  1  0  0  0  0
 24 36  1  0  0  0  0
 27 36  1  0  0  0  0
 36 37  1  0  0  0  0
 30 38  1  0  0  0  0
 13 39  1  0  0  0  0
  5 39  1  0  0  0  0
M  END

     RDKit          3D

 85 89  0  0  0  0  0  0  0  0999 V2000
    6.9293    0.3644    0.1182 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4593    0.4761   -0.0370 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5775   -0.3206    0.8173 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2573   -0.1002    0.5494 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7487   -0.5644   -0.6509 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5083   -1.7788   -1.1974 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1870   -2.6007   -0.1698 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7644   -1.7845    0.9523 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.1326   -2.2458    1.3726 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3452   -1.0147   -0.3972 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2599   -0.3627   -1.1747 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7420    0.5715   -2.2542 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9882    1.3066   -1.8781 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7953    2.4952   -1.0010 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8822    2.3323    0.1424 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2334    3.0114    0.3717 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7224    3.2391    1.7752 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0695    3.5851   -0.7143 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4396    2.8944   -0.6518 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.4665    3.9434   -0.2502 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7709    2.2511   -1.9243 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7921    1.4555   -2.1810 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7829    0.9710   -1.2395 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5938    0.2804   -0.1335 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0625    0.6660    1.2574 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4335   -0.6338    1.7070 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2342   -1.2441    1.5486 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.1329   -2.7015    1.7650 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.8672   -3.4894    0.8931 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6830   -3.0096    1.5207 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1164   -4.1857    2.2410 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9744   -2.2577    0.7054 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4501   -1.0646   -0.0572 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9739   -1.3187   -1.4343 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8275   -1.5878   -2.3077 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6570   -1.2640   -1.7401 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9362   -1.0043    0.0555 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.4916   -2.0494   -0.6610 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9448    0.4173   -1.5623 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3949   -0.5635   -0.2115 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3095    0.7346    1.1168 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3624    1.1467   -0.5843 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2337    0.3704   -1.1191 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2362    1.5789    0.1358 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7090    0.0893    1.8753 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1611   -1.5148   -2.0625 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7309   -2.4435   -1.6844 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4992   -3.4238    0.1864 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9942   -3.1832   -0.7096 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1046   -2.0612    1.8441 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7167   -2.7119    0.5617 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0787   -3.0633    2.1564 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6385   -1.4159    1.8983 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2225   -2.1278   -0.5997 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0996   -0.9834    0.7117 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3129    0.2714   -0.4677 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0243    1.3101   -2.5535 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9468   -0.0247   -3.1847 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3533    1.7591   -2.8675 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7813    2.8897   -0.6108 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4044    3.3707   -1.6019 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1358    1.5856    0.8877 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8130    3.1556    1.8497 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3249    4.1907    2.1833 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3119    2.4346    2.4505 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1929    4.6728   -0.5549 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6222    3.4740   -1.7169 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4561    2.1315    0.1531 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2639    3.4585    0.3098 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9504    4.6758    0.3880 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8275    4.4939   -1.1458 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0889    2.4571   -2.7710 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9445    1.0981   -3.2304 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8445    1.2304   -1.5139 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1862    0.9373    1.8621 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9046    1.3419    1.2733 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4241   -0.7548    2.1303 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4175   -3.0131    2.8098 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8390   -3.4293    1.0340 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6026   -4.2033    3.2596 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4437   -5.1113    1.7373 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0377   -4.1166    2.4169 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9073   -2.5552    0.5807 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9657   -0.1913    0.4370 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2177   -1.6449   -1.2343 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  5  4  1  1
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  5 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 19 20  1  0
 19 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 28 30  1  0
 30 31  1  0
 30 32  2  0
 32 33  1  0
 33 34  1  0
 34 35  2  0
 34 36  1  0
 33 37  1  0
 37 38  1  6
 13 39  1  0
  8  3  1  0
 36 11  1  0
 39  5  1  0
 37 24  1  0
 37 27  1  0
  1 40  1  0
  1 41  1  0
  1 42  1  0
  2 43  1  0
  2 44  1  0
  3 45  1  1
  6 46  1  0
  6 47  1  0
  7 48  1  0
  7 49  1  0
  8 50  1  1
  9 51  1  0
  9 52  1  0
  9 53  1  0
 10 54  1  0
 10 55  1  0
 11 56  1  1
 12 57  1  0
 12 58  1  0
 13 59  1  6
 14 60  1  0
 14 61  1  0
 15 62  1  0
 17 63  1  0
 17 64  1  0
 17 65  1  0
 18 66  1  0
 18 67  1  0
 19 68  1  1
 20 69  1  0
 20 70  1  0
 20 71  1  0
 21 72  1  0
 22 73  1  0
 23 74  1  0
 25 75  1  0
 25 76  1  0
 27 77  1  1
 28 78  1  1
 29 79  1  0
 31 80  1  0
 31 81  1  0
 31 82  1  0
 32 83  1  0
 33 84  1  1
 38 85  1  0
M  END


  Mrv1533004251510112D          

 39 43  0  0  0  0            999 V2000
   11.9087    0.7663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1444    0.4557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4933    0.9623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7290    0.6516    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0778    1.1582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1910    1.9754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9553    2.2861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6064    1.7795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3707    2.0901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4267    1.6648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6624    1.3542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5492    0.5370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2004    0.0304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0873   -0.7868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3230   -1.0974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2098   -1.9146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8610   -2.4212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4455   -2.2252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7944   -1.7187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0301   -2.0293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9075   -0.9015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2564   -0.3949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3695    0.4223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7184    0.9289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8955    0.8697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5849    1.6340    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2158    2.1656    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2429    2.9901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5423    3.4259    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9705    3.3789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6710    2.9432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5958    2.0567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2469    1.5502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1338    0.7330    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0112    1.8608    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8315    1.7461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9188    2.5665    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9976    4.2035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9647    0.3410    0.0000 O   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
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  3  8  1  0  0  0  0
  8  9  1  0  0  0  0
  5 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 15 14  1  4  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 21 19  1  4  0  0  0
 21 22  2  0  0  0  0
 23 22  1  4  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 28 30  1  0  0  0  0
 30 31  2  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 33 35  1  0  0  0  0
 11 35  1  0  0  0  0
 32 36  1  0  0  0  0
 24 36  1  0  0  0  0
 27 36  1  0  0  0  0
 36 37  1  0  0  0  0
 30 38  1  0  0  0  0
 13 39  1  0  0  0  0
  5 39  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0230604

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCC1OC2(CCC1C)CC1CC(CC=C(C)CC(C)C=CC=C3COC4C(O)C(C)=CC(C(=O)O1)C34O)O2

> <INCHI_IDENTIFIER>
InChI=1S/C32H46O7/c1-6-27-21(4)12-13-31(39-27)17-25-16-24(38-31)11-10-20(3)14-19(2)8-7-9-23-18-36-29-28(33)22(5)15-26(30(34)37-25)32(23,29)35/h7-10,15,19,21,24-29,33,35H,6,11-14,16-18H2,1-5H3

> <INCHI_KEY>
VOZIAWLUULBIPN-UHFFFAOYSA-N

> <FORMULA>
C32H46O7

> <MOLECULAR_WEIGHT>
542.713

> <EXACT_MASS>
542.324353821

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
85

> <JCHEM_AVERAGE_POLARIZABILITY>
61.021333945285676

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
6-ethyl-21',24'-dihydroxy-5,11',13',22'-tetramethyl-3',7',19'-trioxaspiro[oxane-2,6'-tetracyclo[15.6.1.1⁴,⁸.0²⁰,²⁴]pentacosane]-10',14',16',22'-tetraen-2'-one

> <ALOGPS_LOGP>
5.48

> <JCHEM_LOGP>
4.529383725999999

> <ALOGPS_LOGS>
-4.74

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.665894791669544

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.553557465703225

> <JCHEM_PKA_STRONGEST_BASIC>
-3.449075134179056

> <JCHEM_POLAR_SURFACE_AREA>
94.45

> <JCHEM_REFRACTIVITY>
151.5963

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
9.97e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6-ethyl-21',24'-dihydroxy-5,11',13',22'-tetramethyl-3',7',19'-trioxaspiro[oxane-2,6'-tetracyclo[15.6.1.1⁴,⁸.0²⁰,²⁴]pentacosane]-10',14',16',22'-tetraen-2'-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 25-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-APR-15         0                                  
HETATM    1  C   UNK     0      22.230   1.430   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      20.803   0.851   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      19.587   1.796   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      18.161   1.216   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      16.945   2.162   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      17.156   3.687   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      18.583   4.267   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      19.799   3.322   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      21.225   3.902   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      15.730   3.108   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      14.303   2.528   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      14.092   1.002   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      15.307   0.057   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      15.096  -1.469   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      13.670  -2.049   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      13.458  -3.574   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      14.674  -4.520   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      12.032  -4.154   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      10.816  -3.208   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       9.390  -3.788   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      11.027  -1.683   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       9.812  -0.737   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      10.023   0.788   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       8.808   1.734   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       7.272   1.623   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       6.692   3.050   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       7.869   4.042   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       7.920   5.582   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       6.612   6.395   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       9.278   6.307   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      10.586   5.494   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      10.445   3.839   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      11.661   2.894   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      11.450   1.368   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0      13.088   3.473   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0       9.019   3.259   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0       9.182   4.791   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0       9.329   7.846   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0      16.734   0.637   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    8                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   10   39                                             
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    3    9                                                  
CONECT    9    8                                                            
CONECT   10    5   11                                                       
CONECT   11   10   12   35                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   39                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25   36                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28   36                                                  
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31   38                                                  
CONECT   31   30   32                                                       
CONECT   32   31   33   36                                                  
CONECT   33   32   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33   11                                                       
CONECT   36   32   24   27   37                                             
CONECT   37   36                                                            
CONECT   38   30                                                            
CONECT   39   13    5                                                       
MASTER        0    0    0    0    0    0    0    0   39    0   86    0
END

View in JSmol

Synonyms

Value	Source
Milbemycin a3	MeSH
Milbemycin b	MeSH
Milbemycin alpha2	MeSH
Milbemycin alpha1	MeSH
Milbemycin alpha13	MeSH
Milbemycin alpha7	MeSH
Milbemectin	MeSH
Milbemycin alpha10	MeSH
Milbemycin alpha5	MeSH
5-Hydroxymilbemycin beta7	MeSH
Milbemycin beta1	MeSH
Milbemycin alpha4	MeSH
Milbemycin alpha11	MeSH
Milbemycin alpha9	MeSH
Milbemycin beta2	MeSH
Milbemycin alpha8	MeSH
Milbemycins	MeSH
Milbemycin beta12	MeSH
Cydectin	MeSH
Milbemycin	MeSH
Milbemycin alpha14	MeSH
Milbemycin alpha15	MeSH
Milbemycin D	MeSH
Moxidectin	MeSH
Milbemycin alpha3	MeSH
Milbemycin alpha6	MeSH
Milbemycin beta3	MeSH

Chemical Formula

C₃₂H₄₆O₇

Average Mass

542.7130 Da

Monoisotopic Mass

542.32435 Da

IUPAC Name

6-ethyl-21',24'-dihydroxy-5,11',13',22'-tetramethyl-3',7',19'-trioxaspiro[oxane-2,6'-tetracyclo[15.6.1.1⁴,⁸.0²⁰,²⁴]pentacosane]-10',14',16',22'-tetraen-2'-one

Traditional Name

6-ethyl-21',24'-dihydroxy-5,11',13',22'-tetramethyl-3',7',19'-trioxaspiro[oxane-2,6'-tetracyclo[15.6.1.1⁴,⁸.0²⁰,²⁴]pentacosane]-10',14',16',22'-tetraen-2'-one

CAS Registry Number

Not Available

SMILES

CCC1OC2(CCC1C)CC1CC(CC=C(C)CC(C)C=CC=C3COC4C(O)C(C)=CC(C(=O)O1)C34O)O2

InChI Identifier

InChI=1S/C32H46O7/c1-6-27-21(4)12-13-31(39-27)17-25-16-24(38-31)11-10-20(3)14-19(2)8-7-9-23-18-36-29-28(33)22(5)15-26(30(34)37-25)32(23,29)35/h7-10,15,19,21,24-29,33,35H,6,11-14,16-18H2,1-5H3

InChI Key

VOZIAWLUULBIPN-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

Species Name	Source	Reference
Streptomyces bingchenggensis	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
Ketal
Oxane
Oxolane
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
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	5.48	ALOGPS
logP	4.53	ChemAxon
logS	-4.7	ALOGPS
pKa (Strongest Acidic)	12.55	ChemAxon
pKa (Strongest Basic)	-3.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	94.45 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	151.6 m³·mol⁻¹	ChemAxon
Polarizability	61.02 Å³	ChemAxon
Number of Rings	5	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

53397745

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 6-ethyl-21',24'-dihydroxy-5,11',13',22'-tetramethyl-3',7',19'-trioxaspiro[oxane-2,6'-tetracyclo[15.6.1.1⁴,⁸.0²⁰,²⁴]pentacosane]-10',14',16',22'-tetraen-2'-one (NP0230604)

MOL for NP0230604 (6-ethyl-21',24'-dihydroxy-5,11',13',22'-tetramethyl-3',7',19'-trioxaspiro[oxane-2,6'-tetracyclo[15.6.1.1⁴,⁸.0²⁰,²⁴]pentacosane]-10',14',16',22'-tetraen-2'-one)

3D MOL for NP0230604 (6-ethyl-21',24'-dihydroxy-5,11',13',22'-tetramethyl-3',7',19'-trioxaspiro[oxane-2,6'-tetracyclo[15.6.1.1⁴,⁸.0²⁰,²⁴]pentacosane]-10',14',16',22'-tetraen-2'-one)

3D SDF for NP0230604 (6-ethyl-21',24'-dihydroxy-5,11',13',22'-tetramethyl-3',7',19'-trioxaspiro[oxane-2,6'-tetracyclo[15.6.1.1⁴,⁸.0²⁰,²⁴]pentacosane]-10',14',16',22'-tetraen-2'-one)

3D-SDF for NP0230604 (6-ethyl-21',24'-dihydroxy-5,11',13',22'-tetramethyl-3',7',19'-trioxaspiro[oxane-2,6'-tetracyclo[15.6.1.1⁴,⁸.0²⁰,²⁴]pentacosane]-10',14',16',22'-tetraen-2'-one)

PDB for NP0230604 (6-ethyl-21',24'-dihydroxy-5,11',13',22'-tetramethyl-3',7',19'-trioxaspiro[oxane-2,6'-tetracyclo[15.6.1.1⁴,⁸.0²⁰,²⁴]pentacosane]-10',14',16',22'-tetraen-2'-one)

3D PDB for NP0230604 (6-ethyl-21',24'-dihydroxy-5,11',13',22'-tetramethyl-3',7',19'-trioxaspiro[oxane-2,6'-tetracyclo[15.6.1.1⁴,⁸.0²⁰,²⁴]pentacosane]-10',14',16',22'-tetraen-2'-one)

SMILES for NP0230604 (6-ethyl-21',24'-dihydroxy-5,11',13',22'-tetramethyl-3',7',19'-trioxaspiro[oxane-2,6'-tetracyclo[15.6.1.1⁴,⁸.0²⁰,²⁴]pentacosane]-10',14',16',22'-tetraen-2'-one)

INCHI for NP0230604 (6-ethyl-21',24'-dihydroxy-5,11',13',22'-tetramethyl-3',7',19'-trioxaspiro[oxane-2,6'-tetracyclo[15.6.1.1⁴,⁸.0²⁰,²⁴]pentacosane]-10',14',16',22'-tetraen-2'-one)

Structure for NP0230604 (6-ethyl-21',24'-dihydroxy-5,11',13',22'-tetramethyl-3',7',19'-trioxaspiro[oxane-2,6'-tetracyclo[15.6.1.1⁴,⁸.0²⁰,²⁴]pentacosane]-10',14',16',22'-tetraen-2'-one)

3D Structure for NP0230604 (6-ethyl-21',24'-dihydroxy-5,11',13',22'-tetramethyl-3',7',19'-trioxaspiro[oxane-2,6'-tetracyclo[15.6.1.1⁴,⁸.0²⁰,²⁴]pentacosane]-10',14',16',22'-tetraen-2'-one)