NP-MRD: Showing NP-Card for avermectin b2a (NP0204284)

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Record Information

Version

2.0

Created at

2022-09-04 23:55:42 UTC

Updated at

2022-09-04 23:55:42 UTC

NP-MRD ID

NP0204284

Secondary Accession Numbers

None

Natural Product Identification

Common Name

avermectin b2a

Description

Avermectin b2a 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. Thus, avermectin B2A is considered to be a macrolide. Avermectin b2a is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. avermectin b2a is found in Streptomyces avermitilis. avermectin b2a was first documented in 2014 (PMID: 24827692). Based on a literature review a small amount of articles have been published on Avermectin b2a (PMID: 35584200) (PMID: 35542930) (PMID: 27075247).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309052201552D          

 63 69  0  0  1  0            999 V2000
   12.5599    0.2597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   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
   11.0313   -0.3615    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
    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  2  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  2  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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    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
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    4.2158    2.1656    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
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   11.3707    2.0901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  5  3  1  1  0  0  0
  5  6  1  0  0  0  0
  7  6  1  1  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  6  0  0  0
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 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  1  0  0  0
 18 17  1  1  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
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 21 22  1  0  0  0  0
 20 23  1  0  0  0  0
 23 24  1  1  0  0  0
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 25 26  1  0  0  0  0
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 60 61  1  6  0  0  0
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  5 62  1  0  0  0  0
 62 63  1  6  0  0  0
M  END

     RDKit          3D

137143  0  0  0  0  0  0  0  0999 V2000
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    8.6639   -2.4581   -1.3042 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7364   -2.7216    0.5152 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.9449   -2.6922   -0.5686 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.2253   -1.6424    2.3131 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.5014   -3.1255    1.4891 H   0  0  0  0  0  0  0  0  0  0  0  0
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    8.8113   -0.4178   -2.3490 H   0  0  0  0  0  0  0  0  0  0  0  0
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    7.0073    1.7672    0.9428 H   0  0  0  0  0  0  0  0  0  0  0  0
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    0.5220    1.4849   -2.1188 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0876    3.0564   -1.5662 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3130    1.7671   -1.6860 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.8241    1.8396    1.7288 H   0  0  0  0  0  0  0  0  0  0  0  0
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 63137  1  0
M  END


  Mrv1652309052201552D          

 63 69  0  0  1  0            999 V2000
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   10.4933    0.9623    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
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    9.0778    1.1582    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
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    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
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  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
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 16 38  1  0  0  0  0
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 44 45  1  0  0  0  0
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 52 53  1  0  0  0  0
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 53 55  1  0  0  0  0
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 52 56  1  0  0  0  0
 43 56  1  0  0  0  0
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 11 58  1  0  0  0  0
  7 58  1  0  0  0  0
  7 59  1  0  0  0  0
 59 60  1  0  0  0  0
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 60 62  1  0  0  0  0
  5 62  1  0  0  0  0
 62 63  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0204284

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCC(C)[C@H]1O[C@@]2(C[C@@H]3C[C@@H](C\C=C(C)\[C@@H](O[C@H]4C[C@H](OC)[C@@H](O[C@H]5C[C@H](OC)[C@@H](O)[C@H](C)O5)[C@H](C)O4)[C@@H](C)\C=C\C=C4/CO[C@@H]5[C@H](O)C(C)=C[C@@H](C(=O)O3)[C@]45O)O2)C[C@H](O)[C@@H]1C

> <INCHI_IDENTIFIER>
InChI=1S/C48H74O15/c1-11-24(2)43-28(6)35(49)22-47(63-43)21-33-18-32(62-47)16-15-26(4)42(25(3)13-12-14-31-23-56-45-40(50)27(5)17-34(46(52)59-33)48(31,45)53)60-39-20-37(55-10)44(30(8)58-39)61-38-19-36(54-9)41(51)29(7)57-38/h12-15,17,24-25,28-30,32-45,49-51,53H,11,16,18-23H2,1-10H3/b13-12+,26-15+,31-14+/t24?,25-,28-,29-,30-,32+,33-,34-,35-,36-,37-,38-,39-,40+,41-,42-,43+,44-,45+,47-,48+/m0/s1

> <INCHI_KEY>
CWGATOJEFAKFBK-QJDTYEMPSA-N

> <FORMULA>
C48H74O15

> <MOLECULAR_WEIGHT>
891.105

> <EXACT_MASS>
890.502771683

> <JCHEM_ACCEPTOR_COUNT>
14

> <JCHEM_ATOM_COUNT>
137

> <JCHEM_AVERAGE_POLARIZABILITY>
96.29193599878315

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1'R,2R,4S,4'S,5S,6R,8'R,10'E,12'S,13'S,14'E,16'E,20'R,21'R,24'S)-6-(butan-2-yl)-4,21',24'-trihydroxy-12'-{[(2R,4S,5S,6S)-5-{[(2S,4S,5S,6S)-5-hydroxy-4-methoxy-6-methyloxan-2-yl]oxy}-4-methoxy-6-methyloxan-2-yl]oxy}-5,11',13',22'-tetramethyl-3',7',19'-trioxaspiro[oxane-2,6'-tetracyclo[15.6.1.1^{4,8}.0^{20,24}]pentacosane]-10',14',16',22'-tetraen-2'-one

> <JCHEM_LOGP>
4.846834697666666

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.159085315191298

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.465381576730142

> <JCHEM_PKA_STRONGEST_BASIC>
-2.928949392279101

> <JCHEM_POLAR_SURFACE_AREA>
190.29

> <JCHEM_REFRACTIVITY>
231.33070000000006

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1'R,2R,4S,4'S,5S,6R,8'R,10'E,12'S,13'S,14'E,16'E,20'R,21'R,24'S)-4,21',24'-trihydroxy-12'-{[(2R,4S,5S,6S)-5-{[(2S,4S,5S,6S)-5-hydroxy-4-methoxy-6-methyloxan-2-yl]oxy}-4-methoxy-6-methyloxan-2-yl]oxy}-5,11',13',22'-tetramethyl-6-(sec-butyl)-3',7',19'-trioxaspiro[oxane-2,6'-tetracyclo[15.6.1.1^{4,8}.0^{20,24}]pentacosane]-10',14',16',22'-tetraen-2'-one

> <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      23.445   0.485   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      22.230   1.430   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      20.803   0.851   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      20.592  -0.675   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      19.587   1.796   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      18.161   1.216   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      16.945   2.162   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      15.730   3.108   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      14.303   2.528   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      14.092   1.002   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      15.307   0.057   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      15.096  -1.469   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      13.670  -2.049   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      13.458  -3.574   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      14.674  -4.520   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      12.032  -4.154   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      11.820  -5.679   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      10.394  -6.259   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      10.183  -7.785   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       8.756  -8.364   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       8.545  -9.890   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       7.118 -10.470   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       7.540  -7.419   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       6.114  -7.999   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       4.898  -7.053   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       3.472  -7.633   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       2.256  -6.687   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       0.829  -7.267   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       0.618  -8.792   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       2.467  -5.162   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       1.252  -4.216   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       3.894  -4.582   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       4.105  -3.056   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       5.109  -5.527   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       7.752  -5.893   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       6.536  -4.948   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0       9.178  -5.313   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0      10.816  -3.208   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       9.390  -3.788   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      11.027  -1.683   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0       9.812  -0.737   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      10.023   0.788   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0       8.808   1.734   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0       7.272   1.623   0.000  0.00  0.00           C+0
HETATM   45  O   UNK     0       6.692   3.050   0.000  0.00  0.00           O+0
HETATM   46  C   UNK     0       7.869   4.042   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0       7.920   5.582   0.000  0.00  0.00           C+0
HETATM   48  O   UNK     0       6.612   6.395   0.000  0.00  0.00           O+0
HETATM   49  C   UNK     0       9.278   6.307   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0       9.329   7.846   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0      10.586   5.494   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0      10.445   3.839   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0      11.661   2.894   0.000  0.00  0.00           C+0
HETATM   54  O   UNK     0      11.450   1.368   0.000  0.00  0.00           O+0
HETATM   55  O   UNK     0      13.088   3.473   0.000  0.00  0.00           O+0
HETATM   56  C   UNK     0       9.019   3.259   0.000  0.00  0.00           C+0
HETATM   57  O   UNK     0       9.182   4.791   0.000  0.00  0.00           O+0
HETATM   58  O   UNK     0      16.734   0.637   0.000  0.00  0.00           O+0
HETATM   59  C   UNK     0      17.156   3.687   0.000  0.00  0.00           C+0
HETATM   60  C   UNK     0      18.583   4.267   0.000  0.00  0.00           C+0
HETATM   61  O   UNK     0      18.794   5.793   0.000  0.00  0.00           O+0
HETATM   62  C   UNK     0      19.799   3.322   0.000  0.00  0.00           C+0
HETATM   63  C   UNK     0      21.225   3.902   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   62                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   58   59                                             
CONECT    8    7    9                                                       
CONECT    9    8   10   55                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   58                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   38                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   37                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   23                                                  
CONECT   21   20   22                                                       
CONECT   22   21                                                            
CONECT   23   20   24   35                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26   34                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28   30                                                  
CONECT   28   27   29                                                       
CONECT   29   28                                                            
CONECT   30   27   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32   25                                                       
CONECT   35   23   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35   18                                                       
CONECT   38   16   39   40                                                  
CONECT   39   38                                                            
CONECT   40   38   41                                                       
CONECT   41   40   42                                                       
CONECT   42   41   43                                                       
CONECT   43   42   44   56                                                  
CONECT   44   43   45                                                       
CONECT   45   44   46                                                       
CONECT   46   45   47   56                                                  
CONECT   47   46   48   49                                                  
CONECT   48   47                                                            
CONECT   49   47   50   51                                                  
CONECT   50   49                                                            
CONECT   51   49   52                                                       
CONECT   52   51   53   56                                                  
CONECT   53   52   54   55                                                  
CONECT   54   53                                                            
CONECT   55   53    9                                                       
CONECT   56   52   43   46   57                                             
CONECT   57   56                                                            
CONECT   58   11    7                                                       
CONECT   59    7   60                                                       
CONECT   60   59   61   62                                                  
CONECT   61   60                                                            
CONECT   62   60    5   63                                                  
CONECT   63   62                                                            
MASTER        0    0    0    0    0    0    0    0   63    0  138    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₄₈H₇₄O₁₅

Average Mass

891.1050 Da

Monoisotopic Mass

890.50277 Da

IUPAC Name

(1'R,2R,4S,4'S,5S,6R,8'R,10'E,12'S,13'S,14'E,16'E,20'R,21'R,24'S)-6-(butan-2-yl)-4,21',24'-trihydroxy-12'-{[(2R,4S,5S,6S)-5-{[(2S,4S,5S,6S)-5-hydroxy-4-methoxy-6-methyloxan-2-yl]oxy}-4-methoxy-6-methyloxan-2-yl]oxy}-5,11',13',22'-tetramethyl-3',7',19'-trioxaspiro[oxane-2,6'-tetracyclo[15.6.1.1^{4,8}.0^{20,24}]pentacosane]-10',14',16',22'-tetraen-2'-one

Traditional Name

(1'R,2R,4S,4'S,5S,6R,8'R,10'E,12'S,13'S,14'E,16'E,20'R,21'R,24'S)-4,21',24'-trihydroxy-12'-{[(2R,4S,5S,6S)-5-{[(2S,4S,5S,6S)-5-hydroxy-4-methoxy-6-methyloxan-2-yl]oxy}-4-methoxy-6-methyloxan-2-yl]oxy}-5,11',13',22'-tetramethyl-6-(sec-butyl)-3',7',19'-trioxaspiro[oxane-2,6'-tetracyclo[15.6.1.1^{4,8}.0^{20,24}]pentacosane]-10',14',16',22'-tetraen-2'-one

CAS Registry Number

Not Available

SMILES

CCC(C)[C@H]1O[C@@]2(C[C@@H]3C[C@@H](C\C=C(C)\[C@@H](O[C@H]4C[C@H](OC)[C@@H](O[C@H]5C[C@H](OC)[C@@H](O)[C@H](C)O5)[C@H](C)O4)[C@@H](C)\C=C\C=C4/CO[C@@H]5[C@H](O)C(C)=C[C@@H](C(=O)O3)[C@]45O)O2)C[C@H](O)[C@@H]1C

InChI Identifier

InChI=1S/C48H74O15/c1-11-24(2)43-28(6)35(49)22-47(63-43)21-33-18-32(62-47)16-15-26(4)42(25(3)13-12-14-31-23-56-45-40(50)27(5)17-34(46(52)59-33)48(31,45)53)60-39-20-37(55-10)44(30(8)58-39)61-38-19-36(54-9)41(51)29(7)57-38/h12-15,17,24-25,28-30,32-45,49-51,53H,11,16,18-23H2,1-10H3/b13-12+,26-15+,31-14+/t24?,25-,28-,29-,30-,32+,33-,34-,35-,36-,37-,38-,39-,40+,41-,42-,43+,44-,45+,47-,48+/m0/s1

InChI Key

CWGATOJEFAKFBK-QJDTYEMPSA-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 avermitilis	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
Disaccharide
Glycosyl compound
O-glycosyl compound
Ketal
Oxane
Tertiary alcohol
Tetrahydrofuran
Secondary alcohol
Carboxylic acid ester
Lactone
Acetal
Carboxylic acid derivative
Polyol
Dialkyl ether
Ether
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Oxacycle
Alcohol
Organic oxide
Hydrocarbon derivative
Carbonyl group
Organic oxygen compound
Organooxygen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

oligosaccharide (CHEBI:29540 )
Macrolides and lactone polyketides (LMPK04000022 )

Physical Properties

State

Not Available

Experimental Properties

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

Predicted Properties

Property	Value	Source
logP	4.85	ChemAxon
pKa (Strongest Acidic)	12.47	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	14	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	190.29 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	231.33 m³·mol⁻¹	ChemAxon
Polarizability	96.29 Å³	ChemAxon
Number of Rings	7	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00016540

Chemspider ID

10128281

KEGG Compound ID

C11975

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11953986

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Xu Q, Li J, Guo W, Xiang J, Zhou L, Zhang J: High Value Utilization of an Avermectin Fermentation Byproduct: Novel B2a Derivatives as Pesticide Candidates. J Agric Food Chem. 2022 Jun 1;70(21):6377-6384. doi: 10.1021/acs.jafc.2c01035. Epub 2022 May 18. [PubMed:35584200 ]
Sun G, Zhang J, Jin S, Zhang J: Synthesis and insecticidal activities of 5-deoxyavermectin B2a oxime ester derivatives. RSC Adv. 2018 Jan 22;8(7):3774-3781. doi: 10.1039/c7ra13258a. eCollection 2018 Jan 16. [PubMed:35542930 ]
Yamada T, Suzuki K, Hirose T, Furuta T, Ueda Y, Kawabata T, Omura S, Sunazuka T: Organocatalytic Site-Selective Acylation of Avermectin B2a, a Unique Endectocidal Drug. Chem Pharm Bull (Tokyo). 2016 Jul 1;64(7):856-64. doi: 10.1248/cpb.c16-00205. Epub 2016 Apr 12. [PubMed:27075247 ]
Gao C, Wang Y, Chen Y, He B, Zhang R, Xu M, Huang R: Two new avermectin derivatives from the Beibu Gulf gorgonian Anthogorgia caerulea. Chem Biodivers. 2014 May;11(5):812-8. doi: 10.1002/cbdv.201300265. [PubMed:24827692 ]
LOTUS database [Link]

Showing NP-Card for avermectin b2a (NP0204284)

MOL for NP0204284 (avermectin b2a)

3D MOL for NP0204284 (avermectin b2a)

3D SDF for NP0204284 (avermectin b2a)

3D-SDF for NP0204284 (avermectin b2a)

PDB for NP0204284 (avermectin b2a)

3D PDB for NP0204284 (avermectin b2a)

SMILES for NP0204284 (avermectin b2a)

INCHI for NP0204284 (avermectin b2a)

Structure for NP0204284 (avermectin b2a)

3D Structure for NP0204284 (avermectin b2a)