NP-MRD: Showing NP-Card for dihydroavermectin b1a (NP0301276)

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Record Information

Version

2.0

Created at

2022-09-10 14:07:41 UTC

Updated at

2022-09-10 14:07:42 UTC

NP-MRD ID

NP0301276

Secondary Accession Numbers

None

Natural Product Identification

Common Name

dihydroavermectin b1a

Description

22,23-Dihydroavermectin b1a, also known as avermectin H2b1a, 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. 22,23-Dihydroavermectin b1a is an extremely weak basic (essentially neutral) compound (based on its pKa). 22,23-Dihydroavermectin b1a is a potentially toxic compound. Ivermectin may also impair normal intrauterine development of O. Volvulus microfilariae and may inhibit their release from the uteri of gravid female worms. While in development, it was assigned the code MK-933 by Merck. 22,23-Dihydroavermectin b1a is a component of Ivermectin, a broad-spectrum antiparasitic avermectin medicine. Avermectins cause irritation of skin and eyes, central nervous system depression (incoordination, tremors, lethargy, excitation, pupil dilation, coma), vomiting, convulsions and/or tremors, and respiratory failure at high doses. This binding causes an increase in the permeability of the cell membrane to chloride ions and results in hyperpolarization of the cell, leading to paralysis and death of the parasite. It has low solubility in water and extensive non-specific binding. It is sold under brand names Sklice and Stromectol in the United States, Ivomec in Europe by Merial Animal Health, Mectizan in Canada by Merck and Ivexterm in Mexico by Valeant Pharmaceuticals International. Adverse effects include muscle or joint pain, dizziness, fever, headache, skin rash, fast heartbeat. Ivermectin is mainly used in humans in the treatment of onchocerciasis, but is also effective against other worm infestations (such as strongyloidiasis, ascariasis, trichuriasis and enterobiasis). dihydroavermectin b1a is found in Streptomyces avermitilis. dihydroavermectin b1a was first documented in 1982 (PMID: 6125361). Route of Elimination: Ivermectin is metabolized in the liver, and ivermectin and/or its metabolites are excreted almost exclusively in the feces over an estimated 12 days, with less than 1% of the administered dose excreted in the urine (PMID: 2411323) (PMID: 6148214) (PMID: 6547280).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 05041406012D          

 84 90  0  0  1  0            999 V2000
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M  END

     RDKit          3D

136142  0  0  0  0  0  0  0  0999 V2000
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M  END


  Mrv0541 05041406012D          

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 18 17  1  0  0  0  0
 25  2  1  6  0  0  0
 25 11  1  0  0  0  0
 26  3  1  1  0  0  0
 26 13  1  0  0  0  0
 27  4  1  0  0  0  0
 27 15  2  0  0  0  0
 28  5  1  6  0  0  0
 28 17  1  0  0  0  0
 29  6  1  0  0  0  0
 29 19  2  0  0  0  0
 30  7  1  1  0  0  0
 31  8  1  1  0  0  0
 32 14  2  0  0  0  0
 32 24  1  0  0  0  0
 33 16  1  0  0  0  0
 33 20  1  0  0  0  0
 34 20  1  0  0  0  0
 34 23  1  0  0  0  0
 35 19  1  0  0  0  0
 36 21  1  0  0  0  0
 37 22  1  0  0  0  0
 38 21  1  0  0  0  0
 39 22  1  0  0  0  0
 40 29  1  0  0  0  0
 41 30  1  0  0  0  0
 41 36  1  0  0  0  0
 42 26  1  0  0  0  0
 42 27  1  0  0  0  0
 43 25  1  1  0  0  0
 43 28  1  0  0  0  0
 44 31  1  0  0  0  0
 44 37  1  0  0  0  0
 45 40  1  0  0  0  0
 46 35  1  0  0  0  0
 47 18  1  0  0  0  0
 47 23  1  0  0  0  0
 48 32  1  0  0  0  0
 48 35  1  0  0  0  0
 48 45  1  0  0  0  0
 40 49  1  6  0  0  0
 41 50  1  6  0  0  0
 51 46  2  0  0  0  0
 48 52  1  1  0  0  0
 53  9  1  0  0  0  0
 36 53  1  1  0  0  0
 54 10  1  0  0  0  0
 37 54  1  1  0  0  0
 55 24  1  0  0  0  0
 55 45  1  0  0  0  0
 56 30  1  0  0  0  0
 56 38  1  0  0  0  0
 57 31  1  0  0  0  0
 57 39  1  0  0  0  0
 58 34  1  0  0  0  0
 58 46  1  0  0  0  0
 39 59  1  6  0  0  0
 42 59  1  1  0  0  0
 38 60  1  6  0  0  0
 44 60  1  6  0  0  0
 61 33  1  0  0  0  0
 47 61  1  6  0  0  0
 62 43  1  0  0  0  0
 62 47  1  0  0  0  0
 63 12  1  0  0  0  0
 64 13  1  0  0  0  0
 65 14  1  0  0  0  0
 66 15  1  0  0  0  0
 25 67  1  1  0  0  0
 26 68  1  6  0  0  0
 28 69  1  1  0  0  0
 30 70  1  6  0  0  0
 31 71  1  6  0  0  0
 33 72  1  1  0  0  0
 34 73  1  1  0  0  0
 35 74  1  6  0  0  0
 36 75  1  6  0  0  0
 37 76  1  6  0  0  0
 38 77  1  1  0  0  0
 39 78  1  1  0  0  0
 40 79  1  1  0  0  0
 41 80  1  1  0  0  0
 42 81  1  6  0  0  0
 43 82  1  6  0  0  0
 44 83  1  1  0  0  0
 45 84  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0301276

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]\C1=C(C)/[C@@]([H])(O[C@@]2([H])C[C@]([H])(OC)[C@@]([H])(O[C@@]3([H])C[C@]([H])(OC)[C@@]([H])(O)[C@]([H])(C)O3)[C@]([H])(C)O2)[C@@]([H])(C)\C([H])=C(/[H])\C(\[H])=C2/CO[C@]3([H])[C@]([H])(O)C(C)=C[C@@]([H])(C(=O)O[C@@]4([H])C[C@@]([H])(C1)O[C@@]1(CC[C@]([H])(C)[C@]([H])(O1)[C@@]([H])(C)CC)C4)[C@]23O

> <INCHI_IDENTIFIER>
InChI=1S/C48H74O14/c1-11-25(2)43-28(5)17-18-47(62-43)23-34-20-33(61-47)16-15-27(4)42(26(3)13-12-14-32-24-55-45-40(49)29(6)19-35(46(51)58-34)48(32,45)52)59-39-22-37(54-10)44(31(8)57-39)60-38-21-36(53-9)41(50)30(7)56-38/h12-15,19,25-26,28,30-31,33-45,49-50,52H,11,16-18,20-24H2,1-10H3/b13-12+,27-15+,32-14+/t25-,26-,28-,30-,31-,33+,34-,35-,36-,37-,38-,39-,40+,41-,42-,43+,44-,45+,47+,48+/m0/s1

> <INCHI_KEY>
AZSNMRSAGSSBNP-XPNPUAGNSA-N

> <FORMULA>
C48H74O14

> <MOLECULAR_WEIGHT>
875.0928

> <EXACT_MASS>
874.507857076

> <JCHEM_ACCEPTOR_COUNT>
13

> <JCHEM_AVERAGE_POLARIZABILITY>
98.19843160421854

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1'R,2R,4'S,5S,6R,8'R,10'E,12'S,13'S,14'E,16'E,20'R,21'R,24'S)-6-[(2S)-butan-2-yl]-21',24'-dihydroxy-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[15.6.1.1⁴,⁸.0²⁰,²⁴]pentacosane]-10',14',16',22'-tetraen-2'-one

> <ALOGPS_LOGP>
4.37

> <JCHEM_LOGP>
5.825745655666666

> <ALOGPS_LOGS>
-5.15

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.169097736330777

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.467904937195897

> <JCHEM_PKA_STRONGEST_BASIC>
-3.4490751341790826

> <JCHEM_POLAR_SURFACE_AREA>
170.05999999999997

> <JCHEM_REFRACTIVITY>
230.32760000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
6.14e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
dihydroavermectin B1a

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-MAY-14   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-MAY-14         0                                  
HETATM    1  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   49  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   50  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   51  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   52  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   53  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   54  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   55  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   56  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   57  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   58  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   59  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   60  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   61  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   62  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   63  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   64  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   65  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   66  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   67  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   68  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   69  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   70  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   71  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   72  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   73  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   74  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   75  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   76  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   77  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   78  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   79  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   80  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   81  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   82  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   83  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   84  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
CONECT    1   11                                                            
CONECT    2   25                                                            
CONECT    3   26                                                            
CONECT    4   27                                                            
CONECT    5   28                                                            
CONECT    6   29                                                            
CONECT    7   30                                                            
CONECT    8   31                                                            
CONECT    9   53                                                            
CONECT   10   54                                                            
CONECT   11    1   25                                                       
CONECT   12   13   14   63                                                  
CONECT   13   12   26   64                                                  
CONECT   14   12   32   65                                                  
CONECT   15   16   27   66                                                  
CONECT   16   15   33                                                       
CONECT   17   18   28                                                       
CONECT   18   17   47                                                       
CONECT   19   29   35                                                       
CONECT   20   33   34                                                       
CONECT   21   36   38                                                       
CONECT   22   37   39                                                       
CONECT   23   34   47                                                       
CONECT   24   32   55                                                       
CONECT   25    2   11   43   67                                             
CONECT   26    3   13   42   68                                             
CONECT   27    4   15   42                                                  
CONECT   28    5   17   43   69                                             
CONECT   29    6   19   40                                                  
CONECT   30    7   41   56   70                                             
CONECT   31    8   44   57   71                                             
CONECT   32   14   24   48                                                  
CONECT   33   16   20   61   72                                             
CONECT   34   20   23   58   73                                             
CONECT   35   19   46   48   74                                             
CONECT   36   21   41   53   75                                             
CONECT   37   22   44   54   76                                             
CONECT   38   21   56   60   77                                             
CONECT   39   22   57   59   78                                             
CONECT   40   29   45   49   79                                             
CONECT   41   30   36   50   80                                             
CONECT   42   26   27   59   81                                             
CONECT   43   25   28   62   82                                             
CONECT   44   31   37   60   83                                             
CONECT   45   40   48   55   84                                             
CONECT   46   35   51   58                                                  
CONECT   47   18   23   61   62                                             
CONECT   48   32   35   45   52                                             
CONECT   49   40                                                            
CONECT   50   41                                                            
CONECT   51   46                                                            
CONECT   52   48                                                            
CONECT   53    9   36                                                       
CONECT   54   10   37                                                       
CONECT   55   24   45                                                       
CONECT   56   30   38                                                       
CONECT   57   31   39                                                       
CONECT   58   34   46                                                       
CONECT   59   39   42                                                       
CONECT   60   38   44                                                       
CONECT   61   33   47                                                       
CONECT   62   43   47                                                       
CONECT   63   12                                                            
CONECT   64   13                                                            
CONECT   65   14                                                            
CONECT   66   15                                                            
CONECT   67   25                                                            
CONECT   68   26                                                            
CONECT   69   28                                                            
CONECT   70   30                                                            
CONECT   71   31                                                            
CONECT   72   33                                                            
CONECT   73   34                                                            
CONECT   74   35                                                            
CONECT   75   36                                                            
CONECT   76   37                                                            
CONECT   77   38                                                            
CONECT   78   39                                                            
CONECT   79   40                                                            
CONECT   80   41                                                            
CONECT   81   42                                                            
CONECT   82   43                                                            
CONECT   83   44                                                            
CONECT   84   45                                                            
MASTER        0    0    0    0    0    0    0    0   84    0  180    0
END

View in JSmol

Synonyms

Value	Source
5-O-Demethyl-22,23-dihydroavermectin a1a	ChEBI
Avermectin H2b1a	ChEBI
Dihydroavermectin b1a	ChEBI
H2b1a	ChEBI
Ivermectin b1a	ChEBI
Stromectol	MeSH
Ivermectin merck brand	MeSH
Ivomec	MeSH
Mectizan	MeSH
Merck brand OF ivermectin	MeSH
Eqvalan	MeSH

Chemical Formula

C₄₈H₇₄O₁₄

Average Mass

875.0928 Da

Monoisotopic Mass

874.50786 Da

IUPAC Name

(1'R,2R,4'S,5S,6R,8'R,10'E,12'S,13'S,14'E,16'E,20'R,21'R,24'S)-6-[(2S)-butan-2-yl]-21',24'-dihydroxy-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[15.6.1.1⁴,⁸.0²⁰,²⁴]pentacosane]-10',14',16',22'-tetraen-2'-one

Traditional Name

dihydroavermectin B1a

CAS Registry Number

Not Available

SMILES

[H]\C1=C(C)/[C@@]([H])(O[C@@]2([H])C[C@]([H])(OC)[C@@]([H])(O[C@@]3([H])C[C@]([H])(OC)[C@@]([H])(O)[C@]([H])(C)O3)[C@]([H])(C)O2)[C@@]([H])(C)\C([H])=C(/[H])\C(\[H])=C2/CO[C@]3([H])[C@]([H])(O)C(C)=C[C@@]([H])(C(=O)O[C@@]4([H])C[C@@]([H])(C1)O[C@@]1(CC[C@]([H])(C)[C@]([H])(O1)[C@@]([H])(C)CC)C4)[C@]23O

InChI Identifier

InChI=1S/C48H74O14/c1-11-25(2)43-28(5)17-18-47(62-43)23-34-20-33(61-47)16-15-27(4)42(26(3)13-12-14-32-24-55-45-40(49)29(6)19-35(46(51)58-34)48(32,45)52)59-39-22-37(54-10)44(31(8)57-39)60-38-21-36(53-9)41(50)30(7)56-38/h12-15,19,25-26,28,30-31,33-45,49-50,52H,11,16-18,20-24H2,1-10H3/b13-12+,27-15+,32-14+/t25-,26-,28-,30-,31-,33+,34-,35-,36-,37-,38-,39-,40+,41-,42-,43+,44-,45+,47+,48+/m0/s1

InChI Key

AZSNMRSAGSSBNP-XPNPUAGNSA-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
Tetrahydrofuran
Tertiary alcohol
Carboxylic acid ester
Lactone
Secondary alcohol
Acetal
Carboxylic acid derivative
Dialkyl ether
Ether
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Organic oxide
Carbonyl group
Hydrocarbon derivative
Alcohol
Organic oxygen compound
Organooxygen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

macrocyclic lactone (CHEBI:63941 )

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	4.37	ALOGPS
logP	5.83	ChemAxon
logS	-5.2	ALOGPS
pKa (Strongest Acidic)	12.47	ChemAxon
pKa (Strongest Basic)	-3.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	13	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	170.06 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	230.33 m³·mol⁻¹	ChemAxon
Polarizability	98.2 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

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

6321424

PDB ID

Not Available

ChEBI ID

63941

Good Scents ID

Not Available

References

General References

Duce IR, Scott RH: Actions of dihydroavermectin B1a on insect muscle. Br J Pharmacol. 1985 Jun;85(2):395-401. doi: 10.1111/j.1476-5381.1985.tb08874.x. [PubMed:2411323 ]
Miwa GT, Walsh JS, VandenHeuvel WJ, Arison B, Sestokas E, Buhs R, Rosegay A, Avermitilis S, Lu AY, Walsh MA, Walker RW, Taub R, Jacob TA: The metabolism of avermectins B1a, H2B1a, and H2B1b by liver microsomes. Drug Metab Dispos. 1982 May-Jun;10(3):268-74. [PubMed:6125361 ]
Chiu SH, Sestokas E, Taub R, Smith JL, Arison B, Lu AY: The metabolism of avermectin-H2B1a and -H2B1b by pig liver microsomes. Drug Metab Dispos. 1984 Jul-Aug;12(4):464-9. [PubMed:6148214 ]
Todd KS Jr, Mansfield ME, DiPietro JA: Anthelmintic efficacy of avermectin B1a and dihydroavermectin B1a against ovine gastrointestinal nematodes in 1977. Am J Vet Res. 1984 May;45(5):976-7. [PubMed:6547280 ]
LOTUS database [Link]

Showing NP-Card for dihydroavermectin b1a (NP0301276)

MOL for NP0301276 (dihydroavermectin b1a)

3D MOL for NP0301276 (dihydroavermectin b1a)

3D SDF for NP0301276 (dihydroavermectin b1a)

3D-SDF for NP0301276 (dihydroavermectin b1a)

PDB for NP0301276 (dihydroavermectin b1a)

3D PDB for NP0301276 (dihydroavermectin b1a)

SMILES for NP0301276 (dihydroavermectin b1a)

INCHI for NP0301276 (dihydroavermectin b1a)

Structure for NP0301276 (dihydroavermectin b1a)

3D Structure for NP0301276 (dihydroavermectin b1a)