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. 2021 Aug 30;19(8):e06824. doi: 10.2903/j.efsa.2021.6824
Code/trivial namea IUPAC name/SMILES notation/InChiKeyb Structural formulac
emamectin B1a (10E,14E,16E)‐(1R,4S,5′S,6S,6′R,8R,12S,13S,20R,21R,24S)‐6′‐[(S)‐sec‐butyl]‐21,24‐dihydroxy‐5′,11,13,22‐tetramethyl‐2‐oxo‐(3,7,19‐trioxatetracyclo[15.6.1.14,8.020,24]pentacosa‐10,14,16,22‐tetraene)‐6‐spiro‐2′‐(5′,6′‐dihydro‐2′H‐pyran)‐12‐yl 2,6‐dideoxy‐3‐O‐methyl‐4‐O‐(2,4,6‐trideoxy‐3‐O‐methyl‐4‐methylamino‐α‐L‐lyxo‐hexapyranosyl)‐α‐L‐arabino‐hexapyranoside
CO[C@H]1C[C@@H](O[C@@H]c[C@H]1NC)O[C@@H]2[C@@H](OC)C[C@@H](O[C@H]2C)O[C@@H]3Cc=CC[C@@H]6C[C@H](OC(=O)[C@@H]4C=Cc[C@@H](O)[C@H]5OCC(=CC=C[C@@H]3C)[C@@]45O)C[C@@]7(O6)C=C[C@H]c[C@H](O7)[C@@H]cCC
CXEGAUYXQAKHKJ‐COFQVFHOSA‐N graphic file with name EFS2-19-e06824-g001.jpg
emamectin B1b (10E,14E,16E)‐(1R,4S,5′S,6S,6′R,8R,12S,13S,20R,21R,24S)‐21,24‐dihydroxy‐6′‐isopropyl‐5′,11,13,22‐tetramethyl‐2‐oxo‐(3,7,19‐trioxatetracyclo[15.6.1.14,8.020,24]pentacosa‐10,14,16,22‐tetraene)‐6‐spiro‐2′‐(5′,6′‐dihydro‐2′H‐pyran)‐12‐yl 2,6‐dideoxy‐3‐O‐methyl‐4‐O‐(2,4,6‐trideoxy‐3‐O‐methyl‐4‐methylamino‐α‐L‐lyxo‐hexapyranosyl)‐α‐L‐arabino‐hexapyranoside
CO[C@H]1C[C@@H](O[C@@H]c[C@H]1NC)O[C@@H]2[C@@H](OC)C[C@@H](O[C@H]2C)O[C@@H]3Cc=CC[C@@H]6C[C@H](OC(=O)[C@@H]4C=Cc[C@@H](O)[C@H]5OCC(=CC=C[C@@H]3C)[C@@]45O)C[C@@]7(O6)C=C[C@H]c[C@H](O7)CcC
DXIOOXFZLKCVHK‐VAUHGISYSA‐N graphic file with name EFS2-19-e06824-g016.jpg
emamectin B1a benzoate (10E,14E,16E)‐(1R,4S,5′S,6S,6′R,8R,12S,13S,20R,21R,24S)‐6′‐[(S)‐sec‐butyl]‐21,24‐dihydroxy‐5′,11,13,22‐tetramethyl‐2‐oxo‐(3,7,19‐trioxatetracyclo[15.6.1.14,8.020,24]pentacosa‐10,14,16,22‐tetraene)‐6‐spiro‐2′‐(5′,6′‐dihydro‐2′H‐pyran)‐12‐yl 2,6‐dideoxy‐3‐O‐methyl‐4‐O‐(2,4,6‐trideoxy‐3‐O‐methyl‐4‐methylamino‐α‐L‐lyxo‐hexapyranosyl)‐α‐L‐arabino‐hexapyranosidebenzoate
O=C(O)c1ccccc1.CO[C@H]1C[C@@H](O[C@@H]c[C@H]1NC)O[C@@H]2[C@@H](OC)C[C@@H](O[C@H]2C)O[C@@H]3Cc=CC[C@@H]6C[C@H](OC(=O)[C@@H]4C=Cc[C@@H](O)[C@H]5OCC(=CC=C[C@@H]3C)[C@@]45O)C[C@@]7(O6)C=C[C@H]c[C@H](O7)[C@@H]cCC
GCKZANITAMOIAR‐PEZUHFCHSA‐N graphic file with name EFS2-19-e06824-g002.jpg
emamectin B1b benzoate (10E,14E,16E)‐(1R,4S,5′S,6S,6′R,8R,12S,13S,20R,21R,24S)‐21,24‐dihydroxy‐6′‐isopropyl‐5′,11,13,22‐tetramethyl‐2‐oxo‐(3,7,19‐trioxatetracyclo[15.6.1.14,8.020,24]pentacosa‐10,14,16,22‐tetraene)‐6‐spiro‐2′‐(5′,6′‐dihydro‐2′H‐pyran)‐12‐yl 2,6‐dideoxy‐3‐O‐methyl‐4‐O‐(2,4,6‐trideoxy‐3‐O‐methyl‐4‐methylamino‐α‐L‐lyxo‐hexapyranosyl)‐α‐L‐arabino‐hexapyranoside benzoate
O=C(O)c1ccccc1.CO[C@H]1C[C@@H](O[C@@H]c[C@H]1NC)O[C@@H]2[C@@H](OC)C[C@@H](O[C@H]2C)O[C@@H]3Cc=CC[C@@H]6C[C@H](OC(=O)[C@@H]4C=Cc[C@@H](O)[C@H]5OCC(=CC=C[C@@H]3C)[C@@]45O)C[C@@]7(O6)C=C[C@H]c[C@H](O7)CcC
ISGYOHXFFCGHKT‐WVYDVIEQSA‐N graphic file with name EFS2-19-e06824-g009.jpg
8,9‐Z‐MAB1a
NOA 438376 (1′R,2S,4’S,5S,6R,8’R,10’E,12’S,13’R,14’E,16’Z,20’R,21’R,24’S)‐6‐[(2S)‐butan‐2‐yl]‐21’,24’‐dihydroxy‐5,11’,13’,22’‐tetramethyl‐2’‐oxo‐5,6‐dihydrospiro[pyran‐2,6’‐[3,7,19]trioxatetracyclo[15.6.1.14,8.020,24]pentacosa[10,14,16,22]tetraen]‐12’‐yl 2,6‐dideoxy‐3‐O‐methyl‐4‐O‐[2,4,6‐trideoxy‐3‐O‐methyl‐4‐(methylamino)‐a‐L‐lyxo‐hexopyranosyl]‐a‐L‐arabino‐hexopyranoside
CO[C@H]1C[C@@H](O[C@@H]c[C@H]1NC)O[C@@H]2[C@@H](OC)C[C@@H](O[C@H]2C)O[C@@H]3Cc=CC[C@@H]6C[C@H](OC(=O)[C@@H]4C=Cc[C@@H](O)[C@H]5OCC(=CC=C[C@H]3C)[C@@]45O)C[C@@]7(O6)C=C[C@H]c[C@H](O7)[C@@H]cCC
CXEGAUYXQAKHKJ‐ITVRGKHNSA‐N graphic file with name EFS2-19-e06824-g014.jpg
FAB1a
NOA 415693 (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‐5,11’,13’,22’‐tetramethyl‐2’‐oxo‐5,6‐dihydrospiro[pyran‐2,6’‐[3,7,19]trioxatetracyclo[15.6.1.14,8.020,24]pentacosa[10,14,16,22]tetraen]‐12’‐yl 2,6‐dideoxy‐3‐O‐methyl‐4‐O‐(2,4,6‐trideoxy‐4‐formamido‐3‐O‐methyl‐a‐L‐lyxo‐hexopyranosyl)‐a‐L‐arabino‐hexopyranoside
CO[C@H]1C[C@@H](O[C@@H]c[C@H]1NC=O)O[C@@H]2[C@@H](OC)C[C@@H](O[C@H]2C)O[C@@H]3Cc=CC[C@@H]6C[C@H](OC(=O)[C@@H]4C=Cc[C@@H](O)[C@H]5OCC(=CC=C[C@@H]3C)[C@@]45O)C[C@@]7(O6)C=C[C@H]c[C@H](O7)[C@@H]cCC
CTOLTUCVXLWGDP‐RTHKNZFHSA‐N graphic file with name EFS2-19-e06824-g012.jpg
MFB1a
NOA 415692 (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‐5,11’,13’,22’‐tetramethyl‐2’‐oxo‐5,6‐dihydrospiro[pyran‐2,6’‐[3,7,19]trioxatetracyclo[15.6.1.14,8.020,24]pentacosa[10,14,16,22]tetraen]‐12’‐yl 2,6‐dideoxy‐3‐O‐methyl‐4‐O‐{2,4,6‐trideoxy‐4‐[formyl(methyl)amino]‐3‐O‐methyl‐a‐L‐lyxo‐hexopyranosyl}‐a‐L‐arabino‐hexopyranoside
O=CNc[C@H]1[C@@H](OC)C[C@@H](O[C@H]1C)O[C@@H]2[C@@H](OC)C[C@@H](O[C@H]2C)O[C@@H]3Cc=CC[C@@H]6C[C@H](OC(=O)[C@@H]4C=Cc[C@@H](O)[C@H]5OCC(=CC=C[C@@H]3C)[C@@]45O)C[C@@]7(O6)C=C[C@H]c[C@H](O7)[C@@H]cCC
BNYCLYCAMIDELK‐OCAZNRKKSA‐N graphic file with name EFS2-19-e06824-g010.jpg
AB1a
NOA 438309 (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‐5,11’,13’,22’‐tetramethyl‐2’‐oxo‐5,6‐dihydrospiro[pyran‐2,6’‐[3,7,19]trioxatetracyclo[15.6.1.14,8.020,24]pentacosa[10,14,16,22]tetraen]‐12’‐yl 4‐O‐(4‐amino‐2,4,6‐trideoxy‐3‐O‐methyl‐a‐L‐lyxo‐hexopyranosyl)‐2,6‐dideoxy‐3‐O‐methyl‐a‐L‐arabino‐hexopyranoside
CO[C@H]1C[C@@H](O[C@@H]c[C@H]1N)O[C@@H]2[C@@H](OC)C[C@@H](O[C@H]2C)O[C@@H]3Cc=CC[C@@H]6C[C@H](OC(=O)[C@@H]4C=Cc[C@@H](O)[C@H]5OCC(=CC=C[C@@H]3C)[C@@]45O)C[C@@]7(O6)C=C[C@H]c[C@H](O7)[C@@H]cCC
WDJBWFOPQSVCHG‐RJHRBHNNSA‐N graphic file with name EFS2-19-e06824-g011.jpg
MSB1a
NOA 419150 (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‐5,11’,13’,22’‐tetramethyl‐2’‐oxo‐5,6‐dihydrospiro[pyran‐2,6’‐[3,7,19]trioxatetracyclo[15.6.1.14,8.020,24]pentacosa[10,14,16,22]tetraen]‐12’‐yl 2,6‐dideoxy‐3‐O‐methyl‐a‐L‐arabino‐hexopyranoside
C[C@@H](CC)[C@H]6O[C@]5(O[C@H]2C[C@H](OC(=O)[C@@H]3C=Cc[C@@H](O)[C@H]4OCC(=CC=C[C@H]c[C@H](O[C@H]1C[C@H](OC)[C@@H](O)[C@H]cO1)Cc=CC2)[C@@]34O)C5)C=C[C@@H]6C
ZBVWYDMYMRLKIV‐OESCZRLOSA‐N graphic file with name EFS2-19-e06824-g004.jpg
Aglycone milbemectin B
NOA 419153 (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]‐12’,21’,24’‐trihydroxy‐5,11’,13’,22’‐tetramethyl‐5,6‐dihydro‐2’H‐spiro[pyran‐2,6’‐[3,7,19]trioxatetracyclo[15.6.1.14,8.020,24]pentacosa[10,14,16,22]tetraen]‐2’‐one
C[C@@H](CC)[C@H]5O[C@]4(O[C@H]1C[C@H](OC(=O)[C@@H]2C=Cc[C@@H](O)[C@H]3OCC(=CC=C[C@H]c[C@H](O)Cc=CC1)[C@@]23O)C4)C=C[C@@H]5C
XLEUIYGDSWMLCR‐AOIHNFKZSA‐N graphic file with name EFS2-19-e06824-g008.jpg

IUPAC: International Union of Pure and Applied Chemistry; SMILES: simplified molecular‐input line‐entry system; InChiKey: International Chemical Identifier Key.

a

The metabolite name in bold is the name used in the conclusion.

b

ACD/Name 2020.2.1 ACD/Labs 2020 Release (File version N15E41, Build 116563, 15 June 2020).

c

ACD/ChemSketch 2020.2.1 ACD/Labs 2020 Release (File version C25H41, Build 121153, 22 March 2021).