(1'R,2S,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,4R,5S,6S)-5-{[(2S,4R,5S,6S)-5-hydroxy-4-methoxy-6-methyloxan-2-yl]oxy}-4-methoxy-6-methyloxan-2-yl]oxy}-5,11',13',22'-tetramethyl-5,6-dihydro-3',7',19'-trioxaspiro[pyran-2,6'-tetracyclo[15.6.1.14,8.020,24]pentacosane]-10',14',16',22'-tetraen-2'-one

• ChemBase ID: 158811
• Molecular Formular: C48H72O14
• Molecular Mass: 873.07688
• Monoisotopic Mass: 872.49220698
• SMILES: [C@H]1(/C(=C/C[C@@H]2C[C@@H](C[C@]3(O2)O[C@@H]([C@H](C=C3)C)[C@@H](C)CC)OC(=O)[C@H]2[C@@]3(/C(=C/C=C/[C@@H]1C)/CO[C@@H]3[C@@H](C(=C2)C)O)O)/C)O[C@H]1C[C@H]([C@H]([C@@H](O1)C)O[C@H]1C[C@H]([C@H]([C@@H](O1)C)O)OC)OC
• Canonical SMILES: CO[C@@H]1C[C@H](O[C@H]2[C@@H](C)/C=C/C=C/3\CO[C@H]4[C@]3(O)[C@@H](C=C([C@H]4O)C)C(=O)O[C@H]3C[C@@H](C/C=C/2\C)O[C@]2(C3)C=C[C@@H]([C@H](O2)[C@H](CC)C)C)O[C@H]([C@@H]1O[C@H]1C[C@@H](OC)[C@H]([C@@H](O1)C)O)C
• InChI: InChI=1S/C48H72O14/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/h12-15,17-19,25-26,28,30-31,33-45,49-50,52H,11,16,20-24H2,1-10H3/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
• InChIKey: RRZXIRBKKLTSOM-RVMVZXQXSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1'R,2S,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,4R,5S,6S)-5-{[(2S,4R,5S,6S)-5-hydroxy-4-methoxy-6-methyloxan-2-yl]oxy}-4-methoxy-6-methyloxan-2-yl]oxy}-5,11',13',22'-tetramethyl-5,6-dihydro-3',7',19'-trioxaspiro[pyran-2,6'-tetracyclo[15.6.1.1^4,^8.0^2^0,^2^4]pentacosane]-10',14',16',22'-tetraen-2'-one
• IUPAC Traditional name: (1'R,2S,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,4R,5S,6S)-5-{[(2S,4R,5S,6S)-5-hydroxy-4-methoxy-6-methyloxan-2-yl]oxy}-4-methoxy-6-methyloxan-2-yl]oxy}-5,11',13',22'-tetramethyl-5,6-dihydro-3',7',19'-trioxaspiro[pyran-2,6'-tetracyclo[15.6.1.1^4,^8.0^2^0,^2^4]pentacosane]-10',14',16',22'-tetraen-2'-one
• Synonyms: Avermectin B1; MK-936; Agri-Mek; Avid; Zephyr; Abamectin

Database IDs

• CAS Number: 71751-41-2
• PubChem SID: 162252946
• PubChem CID: 71312696

CALCULATED PROPERTIES

• Acid pKa: 12.467905
• H Acceptors: 13
• H Donor: 3
• LogD (pH = 5.5): 5.848433
• LogD (pH = 7.4): 5.848429
• Log P: 5.848433
• Molar Refractivity: 231.1798 cm^3
• Polarizability: 91.76681 Å^3
• Polar Surface Area: 170.06 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform; DMSO; Ethyl Acetate
• Apperance: White Solid
• Melting Point: 155-160°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - A107000

Mixture of avermectins, containing at least 80% of avermectin B1a (C48H72O14) and not more than 20% of avermectin B1b (C47H70O14). Used as acaricide, insecticide.

REFERENCES

• Wang, S., et al.: Prog. Clin. Biol. Res., 97, 373 (1982)
• Greenblatt, J.A., et al.: J. Agric. Entomol., 3, 233 (1982)
• Drexler, G., et al.: Eur. J. Pharmacol., 99, 269 (1982)