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Eprinomectin

Eprinomectin

Synopsis, Chemistry

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Also known as: Avermectin b1, 4''-(acetylamino)-4''-deoxy-, (4''r)-, Unii-75kp30fd8o, 75kp30fd8o, Eprinomectin [usan:usp:inn], Zinc306122586, Db11405

Molecular Formula

C₄₉H₇₃NO₁₄

Molecular Weight

900.1 g/mol

InChI Key

WPNHOHPRXXCPRA-TVXIRPTOSA-N

1 2D Structure

Eprinomectin

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

N-[(2S,3R,4R,6S)-6-[(2S,3R,4S,6R)-6-[(1'R,2R,3S,4'S,6S,8'R,10'Z,12'S,13'S,14'Z,16'Z,20'R,21'R,24'S)-21',24'-dihydroxy-3,11',13',22'-tetramethyl-2'-oxo-2-propan-2-ylspiro[2,3-dihydropyran-6,6'-3,7,19-trioxatetracyclo[15.6.1.14,8.020,24]pentacosa-10,14,16,22-tetraene]-12'-yl]oxy-4-methoxy-2-methyloxan-3-yl]oxy-4-methoxy-2-methyloxan-3-yl]acetamide

2.1.2 InChI

InChI=1S/C49H73NO14/c1-25(2)43-28(5)17-18-48(64-43)23-35-20-34(63-48)16-15-27(4)44(26(3)13-12-14-33-24-57-46-42(52)29(6)19-36(47(53)60-35)49(33,46)54)61-40-22-38(56-11)45(31(8)59-40)62-39-21-37(55-10)41(30(7)58-39)50-32(9)51/h12-15,17-19,25-26,28,30-31,34-46,52,54H,16,20-24H2,1-11H3,(H,50,51)/b13-12-,27-15-,33-14-/t26-,28-,30-,31-,34+,35-,36-,37+,38-,39-,40-,41+,42+,43+,44-,45+,46+,48+,49+/m0/s1

2.1.3 InChI Key

WPNHOHPRXXCPRA-TVXIRPTOSA-N

2.1.4 Canonical SMILES

CC1C=CC=C2COC3C2(C(C=C(C3O)C)C(=O)OC4CC(CC=C(C1OC5CC(C(C(O5)C)OC6CC(C(C(O6)C)NC(=O)C)OC)OC)C)OC7(C4)C=CC(C(O7)C(C)C)C)O

2.1.5 Isomeric SMILES

C[C@H]1/C=C\C=C/2\CO[C@H]3[C@@]2([C@@H](C=C([C@H]3O)C)C(=O)O[C@H]4C[C@@H](C/C=C(\[C@H]1O[C@H]5C[C@@H]([C@@H]([C@@H](O5)C)O[C@H]6C[C@H]([C@@H]([C@@H](O6)C)NC(=O)C)OC)OC)/C)O[C@]7(C4)C=C[C@@H]([C@H](O7)C(C)C)C)O

2.2 Synonyms

2.2.1 MeSH Synonyms

1. 4''-epi-methylamino-4''-deoxyavermectin B1

2. 4''-epiacetylamino-4''-deoxyavermectin B1

3. 4''-epiacetylamino-4''-deoxyavermectin B1, (4''r)-isomer

4. Avermectin B1, 4''-(acetylamino)-4''-deoxy-, (4''r)-

5. Emamectin

6. Gwn-1972

7. Mk 243

8. Mk-243

2.2.2 Depositor-Supplied Synonyms

1. Avermectin B1, 4''-(acetylamino)-4''-deoxy-, (4''r)-

2. Unii-75kp30fd8o

3. 75kp30fd8o

4. Eprinomectin [usan:usp:inn]

5. Zinc306122586

6. Db11405

7. A Mixture Of Two Components Having A Ratio Of 90% Or More Of Epinometin Component B1a And 10% Or Less Of Eprinometin Component B1b

8. A Mixture Of Two Components Having A Ratio Of 90% Or More Of Eprinomectin Component B1a And 10% Or Less Of Eprinomectin Component B1b

9. N-[(2s,3r,4r,6s)-6-[(2s,3r,4s,6r)-6-[(1'r,2r,3s,4's,6s,8'r,10'z,12's,13's,14'z,16'z,20'r,21'r,24's)-21',24'-dihydroxy-3,11',13',22'-tetramethyl-2'-oxo-2-propan-2-ylspiro[2,3-dihydropyran-6,6'-3,7,19-trioxatetracyclo[15.6.1.14,8.020,24]pentacosa-10,14,16,22-tetraene]-12'-yl]oxy-4-methoxy-2-methyloxan-3-yl]oxy-4-methoxy-2-methyloxan-3-yl]acetamide

2.3 Create Date

2006-04-29

3 Chemical and Physical Properties

Molecular Formula	C₄₉H₇₃NO₁₄
Molecular Weight	900.1 g/mol
XLogP3	3.5
Hydrogen Bond Donor Count	3
Hydrogen Bond Acceptor Count	14
Rotatable Bond Count	8
Exact Mass	899.50310600 g/mol
Monoisotopic Mass	899.50310600 g/mol
Topological Polar Surface Area	179 Å²
Heavy Atom Count	64
Formal Charge	0
Complexity	1830
Isotope Atom Count	0
Defined Atom Stereocenter Count	19
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	3
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Pharmacology and Biochemistry

4.1 MeSH Pharmacological Classification

Insecticides

Pesticides designed to control insects that are harmful to man. The insects may be directly harmful, as those acting as disease vectors, or indirectly harmful, as destroyers of crops, food products, or textile fabrics. (See all compounds classified as Insecticides.)