NP-MRD: Showing NP-Card for (1'r,2r,4's,5s,6r,8'r,10'e,13'r,14'e,16'e,20'r,21'r,24's)-21',24'-dihydroxy-5,6,11',13'-tetramethyl-2'-oxo-3',7',19'-trioxaspiro[oxane-2,6'-tetracyclo[15.6.1.1⁴,⁸.0²⁰,²⁴]pentacosane]-10',14',16',22'-tetraen-22'-ylmethyl propanoate (NP0212596)

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Record Information

Version

2.0

Created at

2022-09-05 11:18:23 UTC

Updated at

2022-09-05 11:18:23 UTC

NP-MRD ID

NP0212596

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1'r,2r,4's,5s,6r,8'r,10'e,13'r,14'e,16'e,20'r,21'r,24's)-21',24'-dihydroxy-5,6,11',13'-tetramethyl-2'-oxo-3',7',19'-trioxaspiro[oxane-2,6'-tetracyclo[15.6.1.1⁴,⁸.0²⁰,²⁴]pentacosane]-10',14',16',22'-tetraen-22'-ylmethyl propanoate

Description

Milbemycin alpha22, also known as milbemycin α22, 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. (1'r,2r,4's,5s,6r,8'r,10'e,13'r,14'e,16'e,20'r,21'r,24's)-21',24'-dihydroxy-5,6,11',13'-tetramethyl-2'-oxo-3',7',19'-trioxaspiro[oxane-2,6'-tetracyclo[15.6.1.1⁴,⁸.0²⁰,²⁴]pentacosane]-10',14',16',22'-tetraen-22'-ylmethyl propanoate is found in Streptomyces hygroscopicus. Based on a literature review very few articles have been published on Milbemycin alpha22.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309052213182D          

 43 47  0  0  1  0            999 V2000
    3.6507    6.7241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6236    5.8995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3242    5.4638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0518    5.8526    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2971    4.6392    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
    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  1  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
    7.6624    1.3542    0.0000 C   0  0  1  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
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  1  2  1  0  0  0  0
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  9  8  1  1  0  0  0
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 13 43  1  0  0  0  0
M  END

     RDKit          3D

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M  END


  Mrv1652309052213182D          

 43 47  0  0  1  0            999 V2000
    3.6507    6.7241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6236    5.8995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3242    5.4638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0518    5.8526    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2971    4.6392    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
    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  1  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
    7.6624    1.3542    0.0000 C   0  0  1  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  1  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  1  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  2  0  0  0  0  0  0  0  0  0
    4.2429    2.9901    0.0000 C   0  0  2  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
    4.8315    1.7461    0.0000 C   0  0  2  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
    8.9647    0.3410    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0778    1.1582    0.0000 C   0  0  2  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  2  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
   10.4933    0.9623    0.0000 C   0  0  1  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
    9.7290    0.6516    0.0000 O   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
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  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  2  0  0  0  0
  9  8  1  1  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  6  0  0  0
 15 14  1  6  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  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  1  0  0  0
 21 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 29 28  1  6  0  0  0
 29 30  1  0  0  0  0
  7 30  1  0  0  0  0
 30 31  1  6  0  0  0
 29 32  1  0  0  0  0
 26 32  1  0  0  0  0
  9 32  1  0  0  0  0
 32 33  1  1  0  0  0
 15 34  1  0  0  0  0
 35 34  1  6  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  1  0  0  0  0
 38 39  1  6  0  0  0
 38 40  1  0  0  0  0
 40 41  1  1  0  0  0
 40 42  1  0  0  0  0
 35 42  1  0  0  0  0
 35 43  1  0  0  0  0
 13 43  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0212596

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCC(=O)OCC1=C[C@H]2C(=O)O[C@H]3C[C@@H](C\C=C(C)\C[C@@H](C)\C=C\C=C4/CO[C@H]([C@@H]1O)[C@]24O)O[C@@]1(CC[C@H](C)[C@@H](C)O1)C3

> <INCHI_IDENTIFIER>
InChI=1S/C34H48O9/c1-6-29(35)39-18-24-15-28-32(37)41-27-16-26(43-33(17-27)13-12-22(4)23(5)42-33)11-10-21(3)14-20(2)8-7-9-25-19-40-31(30(24)36)34(25,28)38/h7-10,15,20,22-23,26-28,30-31,36,38H,6,11-14,16-19H2,1-5H3/b8-7+,21-10+,25-9+/t20-,22-,23+,26+,27-,28-,30+,31+,33-,34+/m0/s1

> <INCHI_KEY>
XLQIVSCKAHVDRB-ITOYOHLKSA-N

> <FORMULA>
C34H48O9

> <MOLECULAR_WEIGHT>
600.749

> <EXACT_MASS>
600.329833126

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
91

> <JCHEM_AVERAGE_POLARIZABILITY>
66.07175558931738

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[(1'R,2R,4'S,5S,6R,8'R,10'E,13'R,14'E,20'R,21'R,24'S)-21',24'-dihydroxy-5,6,11',13'-tetramethyl-2'-oxo-3',7',19'-trioxaspiro[oxane-2,6'-tetracyclo[15.6.1.1^{4,8}.0^{20,24}]pentacosane]-10',14',16',22'-tetraen-22'-yl]methyl propanoate

> <JCHEM_LOGP>
3.867751431666665

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.601640570323013

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.544711278555578

> <JCHEM_PKA_STRONGEST_BASIC>
-3.480930425841466

> <JCHEM_POLAR_SURFACE_AREA>
120.75000000000001

> <JCHEM_REFRACTIVITY>
162.62540000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1'R,2R,4'S,5S,6R,8'R,10'E,13'R,14'E,20'R,21'R,24'S)-21',24'-dihydroxy-5,6,11',13'-tetramethyl-2'-oxo-3',7',19'-trioxaspiro[oxane-2,6'-tetracyclo[15.6.1.1^{4,8}.0^{20,24}]pentacosane]-10',14',16',22'-tetraen-22'-ylmethyl propanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-22         0                                  
HETATM    1  C   UNK     0       6.815  12.552   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.764  11.012   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.072  10.199   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       9.430  10.925   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0       8.021   8.660   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       9.329   7.846   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.278   6.307   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      10.586   5.494   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      10.445   3.839   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      11.661   2.894   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      11.450   1.368   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      13.088   3.473   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      14.303   2.528   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      14.092   1.002   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      15.307   0.057   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      15.096  -1.469   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      13.670  -2.049   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      13.458  -3.574   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      14.674  -4.520   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      12.032  -4.154   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      10.816  -3.208   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       9.390  -3.788   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      11.027  -1.683   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       9.812  -0.737   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      10.023   0.788   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       8.808   1.734   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       7.272   1.623   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       6.692   3.050   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       7.869   4.042   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       7.920   5.582   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       6.612   6.395   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       9.019   3.259   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       9.182   4.791   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0      16.734   0.637   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0      16.945   2.162   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      17.156   3.687   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      18.583   4.267   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      19.799   3.322   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      21.225   3.902   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      19.587   1.796   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      20.803   0.851   0.000  0.00  0.00           C+0
HETATM   42  O   UNK     0      18.161   1.216   0.000  0.00  0.00           O+0
HETATM   43  C   UNK     0      15.730   3.108   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   30                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   32                                                  
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14   43                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   34                                                  
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   32                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30   32                                                  
CONECT   30   29    7   31                                                  
CONECT   31   30                                                            
CONECT   32   29   26    9   33                                             
CONECT   33   32                                                            
CONECT   34   15   35                                                       
CONECT   35   34   36   42   43                                             
CONECT   36   35   37                                                       
CONECT   37   36   38                                                       
CONECT   38   37   39   40                                                  
CONECT   39   38                                                            
CONECT   40   38   41   42                                                  
CONECT   41   40                                                            
CONECT   42   40   35                                                       
CONECT   43   35   13                                                       
MASTER        0    0    0    0    0    0    0    0   43    0   94    0
END

View in JSmol

Synonyms

Value	Source
Milbemycin a22	Generator
Milbemycin α22	Generator

Chemical Formula

C₃₄H₄₈O₉

Average Mass

600.7490 Da

Monoisotopic Mass

600.32983 Da

IUPAC Name

[(1'R,2R,4'S,5S,6R,8'R,10'E,13'R,14'E,20'R,21'R,24'S)-21',24'-dihydroxy-5,6,11',13'-tetramethyl-2'-oxo-3',7',19'-trioxaspiro[oxane-2,6'-tetracyclo[15.6.1.1^{4,8}.0^{20,24}]pentacosane]-10',14',16',22'-tetraen-22'-yl]methyl propanoate

Traditional Name

(1'R,2R,4'S,5S,6R,8'R,10'E,13'R,14'E,20'R,21'R,24'S)-21',24'-dihydroxy-5,6,11',13'-tetramethyl-2'-oxo-3',7',19'-trioxaspiro[oxane-2,6'-tetracyclo[15.6.1.1^{4,8}.0^{20,24}]pentacosane]-10',14',16',22'-tetraen-22'-ylmethyl propanoate

CAS Registry Number

Not Available

SMILES

CCC(=O)OCC1=C[C@H]2C(=O)O[C@H]3C[C@@H](C\C=C(C)\C[C@@H](C)\C=C\C=C4/CO[C@H]([C@@H]1O)[C@]24O)O[C@@]1(CC[C@H](C)[C@@H](C)O1)C3

InChI Identifier

InChI=1S/C34H48O9/c1-6-29(35)39-18-24-15-28-32(37)41-27-16-26(43-33(17-27)13-12-22(4)23(5)42-33)11-10-21(3)14-20(2)8-7-9-25-19-40-31(30(24)36)34(25,28)38/h7-10,15,20,22-23,26-28,30-31,36,38H,6,11-14,16-19H2,1-5H3/b8-7+,21-10+,25-9+/t20-,22-,23+,26+,27-,28-,30+,31+,33-,34+/m0/s1

InChI Key

XLQIVSCKAHVDRB-ITOYOHLKSA-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
Ketal
Dicarboxylic acid or derivatives
Oxane
Tertiary alcohol
Oxolane
Carboxylic acid ester
Lactone
Secondary alcohol
Acetal
Carboxylic acid derivative
Dialkyl ether
Ether
Oxacycle
Organoheterocyclic compound
Organic oxide
Carbonyl group
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	3.87	ChemAxon
pKa (Strongest Acidic)	12.54	ChemAxon
pKa (Strongest Basic)	-3.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	120.75 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	162.63 m³·mol⁻¹	ChemAxon
Polarizability	66.07 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

8683202

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10507801

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1'r,2r,4's,5s,6r,8'r,10'e,13'r,14'e,16'e,20'r,21'r,24's)-21',24'-dihydroxy-5,6,11',13'-tetramethyl-2'-oxo-3',7',19'-trioxaspiro[oxane-2,6'-tetracyclo[15.6.1.1⁴,⁸.0²⁰,²⁴]pentacosane]-10',14',16',22'-tetraen-22'-ylmethyl propanoate (NP0212596)

MOL for NP0212596 ((1'r,2r,4's,5s,6r,8'r,10'e,13'r,14'e,16'e,20'r,21'r,24's)-21',24'-dihydroxy-5,6,11',13'-tetramethyl-2'-oxo-3',7',19'-trioxaspiro[oxane-2,6'-tetracyclo[15.6.1.1⁴,⁸.0²⁰,²⁴]pentacosane]-10',14',16',22'-tetraen-22'-ylmethyl propanoate)

3D MOL for NP0212596 ((1'r,2r,4's,5s,6r,8'r,10'e,13'r,14'e,16'e,20'r,21'r,24's)-21',24'-dihydroxy-5,6,11',13'-tetramethyl-2'-oxo-3',7',19'-trioxaspiro[oxane-2,6'-tetracyclo[15.6.1.1⁴,⁸.0²⁰,²⁴]pentacosane]-10',14',16',22'-tetraen-22'-ylmethyl propanoate)

3D SDF for NP0212596 ((1'r,2r,4's,5s,6r,8'r,10'e,13'r,14'e,16'e,20'r,21'r,24's)-21',24'-dihydroxy-5,6,11',13'-tetramethyl-2'-oxo-3',7',19'-trioxaspiro[oxane-2,6'-tetracyclo[15.6.1.1⁴,⁸.0²⁰,²⁴]pentacosane]-10',14',16',22'-tetraen-22'-ylmethyl propanoate)

3D-SDF for NP0212596 ((1'r,2r,4's,5s,6r,8'r,10'e,13'r,14'e,16'e,20'r,21'r,24's)-21',24'-dihydroxy-5,6,11',13'-tetramethyl-2'-oxo-3',7',19'-trioxaspiro[oxane-2,6'-tetracyclo[15.6.1.1⁴,⁸.0²⁰,²⁴]pentacosane]-10',14',16',22'-tetraen-22'-ylmethyl propanoate)

PDB for NP0212596 ((1'r,2r,4's,5s,6r,8'r,10'e,13'r,14'e,16'e,20'r,21'r,24's)-21',24'-dihydroxy-5,6,11',13'-tetramethyl-2'-oxo-3',7',19'-trioxaspiro[oxane-2,6'-tetracyclo[15.6.1.1⁴,⁸.0²⁰,²⁴]pentacosane]-10',14',16',22'-tetraen-22'-ylmethyl propanoate)

3D PDB for NP0212596 ((1'r,2r,4's,5s,6r,8'r,10'e,13'r,14'e,16'e,20'r,21'r,24's)-21',24'-dihydroxy-5,6,11',13'-tetramethyl-2'-oxo-3',7',19'-trioxaspiro[oxane-2,6'-tetracyclo[15.6.1.1⁴,⁸.0²⁰,²⁴]pentacosane]-10',14',16',22'-tetraen-22'-ylmethyl propanoate)

SMILES for NP0212596 ((1'r,2r,4's,5s,6r,8'r,10'e,13'r,14'e,16'e,20'r,21'r,24's)-21',24'-dihydroxy-5,6,11',13'-tetramethyl-2'-oxo-3',7',19'-trioxaspiro[oxane-2,6'-tetracyclo[15.6.1.1⁴,⁸.0²⁰,²⁴]pentacosane]-10',14',16',22'-tetraen-22'-ylmethyl propanoate)

INCHI for NP0212596 ((1'r,2r,4's,5s,6r,8'r,10'e,13'r,14'e,16'e,20'r,21'r,24's)-21',24'-dihydroxy-5,6,11',13'-tetramethyl-2'-oxo-3',7',19'-trioxaspiro[oxane-2,6'-tetracyclo[15.6.1.1⁴,⁸.0²⁰,²⁴]pentacosane]-10',14',16',22'-tetraen-22'-ylmethyl propanoate)

Structure for NP0212596 ((1'r,2r,4's,5s,6r,8'r,10'e,13'r,14'e,16'e,20'r,21'r,24's)-21',24'-dihydroxy-5,6,11',13'-tetramethyl-2'-oxo-3',7',19'-trioxaspiro[oxane-2,6'-tetracyclo[15.6.1.1⁴,⁸.0²⁰,²⁴]pentacosane]-10',14',16',22'-tetraen-22'-ylmethyl propanoate)

3D Structure for NP0212596 ((1'r,2r,4's,5s,6r,8'r,10'e,13'r,14'e,16'e,20'r,21'r,24's)-21',24'-dihydroxy-5,6,11',13'-tetramethyl-2'-oxo-3',7',19'-trioxaspiro[oxane-2,6'-tetracyclo[15.6.1.1⁴,⁸.0²⁰,²⁴]pentacosane]-10',14',16',22'-tetraen-22'-ylmethyl propanoate)