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Avermectin

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Name

Avermectin

EINECS N/A
CAS No. 73989-17-0 Density 1.27 g/cm3
PSA 170.06000 LogP 4.18670
Solubility N/A Melting Point N/A
Formula C44H66O14 Boiling Point 923.5 °C at 760 mmHg
Molecular Weight 818.99 Flash Point 269.8 °C
Transport Information N/A Appearance N/A
Safety Risk Codes N/A
Molecular Structure Molecular Structure of 73989-17-0 (Avermectin) Hazard Symbols N/A
Synonyms

Aifuding;3',4',5',6,6',10,11,14,15,17,17a,20,20a,20b-Tetradecahydro-2H,7H-spiro[11,15-methanofuro[4,3,2-pq][2,6]benzodioxacyclooctadeci ne-13,2'-pyran]-7-yl 2,6-dideoxy-4-O-(2,6-dideoxy-3-O-methyl-α-L-arabino-hexopyranosyl)-3-O-methyl-L-arabino-hexopyranoside;(2aZ,4Z,5'S,7S,8Z,20R,20bS)-20,20b-Dihydroxy-5',6,8,19-tetramethyl-17-oxo-3',4',5',6,6',10,11,14,15,17,17a,20,20a,20b-tetradecahydro-2H,7H-spiro[11,15-methanofuro[4,3,2-pq][2,6]benzodioxacyclooctadeci ne-13,2'-pyran]-7-yl 2,6-dideoxy-4-O-(2,6-dideoxy-3-O-methyl-α-L-arabino-hexopyranosyl)-3-O-methyl-L-arabino-hexopyranoside;LS-22263;

 

Avermectin History

In 1978, an actinomycete was isolated at The Kitasato Institute from a soil sample collected at Kawana, Ito City, Shizuoka Prefecture, Japan. Later that year, the isolated actinomycete was sent to Merck Sharp & Dohme Research Laboratories for testing. Various, carefully controlled broths were fermented using the isolated actinomycete. Early tests indicated that some of the whole, fermented broths were active against Nematospiroides dubius in mice over at least an eightfold range without notable toxicity. Subsequently, the anthelmintic activity was isolated and identified as a family of closely related compounds. In early October 1978, a team from Merck Sharp & Dohme Research Laboratories led by Richard W Burg, and Ruiko Oiwa and Satoshi Omura of The Kitasato Institute and Kitasato University, presented their findings at the 18th Interscience Conference on Antimicrobial Agents and Chemotherapy, Atlanta, Georgia.In 2002, Yoko Takahashi and others at the Kitasato Institute for Life Sciences, Kitasato University and at The Kitasato Institute, proposed that Streptomyces avermitilis be renamed Streptomyces avermectinius.

Avermectin Specification

The Avermectin with CAS registry number of 73989-17-0 is also known as 3',4',5',6,6',10,11,14,15,17,17a,20,20a,20b-Tetradecahydro-2H,7H-spiro[11,15-methanofuro[4,3,2-pq][2,6]benzodioxacyclooctadeci ne-13,2'-pyran]-7-yl 2,6-dideoxy-4-O-(2,6-dideoxy-3-O-methyl-α-L-arabino-hexopyranosyl)-3-O-methyl-L-arabino-hexopyranoside. The systematic name and product name are tha same. In addition, the formula is C44H66O14 and the molecular weight is 818.99.

Physical properties about Avermectin are: (1)ACD/LogP: 4.71; (2)# of Rule of 5 Violations: 2; (3)ACD/LogD (pH 5.5): 4.71; (4)ACD/LogD (pH 7.4): 4.71; (5)ACD/BCF (pH 5.5): 2233.43; (6)ACD/BCF (pH 7.4): 2233.4; (7)ACD/KOC (pH 5.5): 8685.41; (8)ACD/KOC (pH 7.4): 8685.29; (9)#H bond acceptors: 14; (10)#H bond donors: 3; (11)#Freely Rotating Bonds: 9; (12)Index of Refraction: 1.573; (13)Molar Refractivity: 212.24 cm3; (14)Molar Volume: 643.2 cm3; (15)Surface Tension: 54.1 dyne/cm; (16)Density: 1.27 g/cm3; (17)Flash Point: 269.8 °C; (18)Enthalpy of Vaporization: 152.43 kJ/mol; (19)Boiling Point: 923.5 °C at 760 mmHg; (20)Vapour Pressure: 0 mmHg at 25 °C.

You can still convert the following datas into molecular structure:
1. Canonical SMILES: CC1CCC2(CC3CC(O2)CC=C(C(C(C=CC=C4COC5C4(C(C=C(C5O)C)C(=O)O3)O)C)OC6CC(C(C(O6)C)OC7CC(C(C(O7)C)O)OC)OC)C)OC1
2. Isomeric SMILES: C[C@H]1CCC2(CC3CC(O2)C/C=C(\[C@H](C(/C=C\C=C/4\COC5[C@@]4(C(C=C([C@H]5O)C)C(=O)O3)O)C)OC6C[C@@H]([C@H]([C@@H](O6)C)O[C@H]7C[C@@H]([C@H]([C@@H](O7)C)O)OC)OC)/C)OC1
3. InChI: InChI=1S/C44H66O14/c1-23-14-15-43(52-21-23)20-31-17-30(58-43)13-12-25(3)39(24(2)10-9-11-29-22-51-41-37(45)26(4)16-32(42(47)55-31)44(29,41)48)56-36-19-34(50-8)40(28(6)54-36)57-35-18-33(49-7)38(46)27(5)53-35/h9-12,16,23-24,27-28,30-41,45-46,48H,13-15,17-22H2,1-8H3/b10-9-,25-12-,29-11-/t23-,24?,27-,28-,30?,31?,32?,33-,34-,35-,36?,37+,38-,39-,40-,41?,43?,44+/m0/s1
4. InChIKey: UWHFYBDCEDSMAI-ZYARWCFOSA-N

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