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. 2022 Jun 23;20(6):e07328. doi: 10.2903/j.efsa.2022.7328
Code/trivial name (a) IUPAC name/SMILES notation/InChiKey (b) Structural formula (c)
Isoflucypram

N‐(5‐chloro‐2‐isopropylbenzyl)‐N‐cyclopropyl‐3‐(difluoromethyl)‐5‐fluoro‐1‐methyl‐1H‐pyrazole‐4‐carboxamide

FC(F)c1nn(C)c(F)c1C(=O)N(Cc1cc(Cl)ccc1C(C)C)C1CC1

JEFUQUGZXLEHLD‐UHFFFAOYSA‐N

graphic file with name EFS2-20-e07328-g016.jpg
BCS‐CN45153

N‐cyclopropyl‐3‐(difluoromethyl)‐5‐fluoro‐1‐methyl‐N‐{[2‐(propan‐2‐yl)phenyl]methyl}‐1H‐pyrazole‐4‐carboxamide

FC(F)c1nn(C)c(F)c1C(=O)N(Cc1ccccc1C(C)C)C1CC1

YBQARPUVLHEOSY‐UHFFFAOYSA‐N

graphic file with name EFS2-20-e07328-g005.jpg
BCS‐CR73065

3‐(difluoromethyl)‐5‐fluoro‐1‐methyl‐1H‐pyrazole‐4‐carboxylic acid

FC(F)c1nn(C)c(F)c1C(=O)O

AXJCNOQHTJLWDH‐UHFFFAOYSA‐N

graphic file with name EFS2-20-e07328-g009.jpg
BCS‐AA10447

N,N‐dimethylcyclohexanamine

CN(C)C1CCCCC1

SVYKKECYCPFKGB‐UHFFFAOYSA‐N

graphic file with name EFS2-20-e07328-g021.jpg
M01

N‐{[5‐chloro‐2‐(1‐hydroxypropan‐2‐yl)phenyl]methyl}‐N‐cyclopropyl‐3‐(difluoromethyl)‐5‐fluoro‐1‐methyl‐1H‐pyrazole‐4‐carboxamide

FC(F)c1nn(C)c(F)c1C(=O)N(Cc1cc(Cl)ccc1C(C)CO)C1CC1

NELOYSZGILQIFZ‐UHFFFAOYSA‐N

graphic file with name EFS2-20-e07328-g029.jpg
M02

N‐{[5‐chloro‐2‐(2‐hydroxypropan‐2‐yl)phenyl]methyl}‐N‐cyclopropyl‐3‐(difluoromethyl)‐5‐fluoro‐1‐methyl‐1H‐pyrazole‐4‐carboxamide

FC(F)c1nn(C)c(F)c1C(=O)N(Cc1cc(Cl)ccc1C(C)(C)O)C1CC1

FJMAZWFCKUQOAG‐UHFFFAOYSA‐N

graphic file with name EFS2-20-e07328-g002.jpg
M06

N‐{[5‐chloro‐2‐(1‐hydroxypropan‐2‐yl)phenyl]methyl}‐N‐cyclopropyl‐3‐(difluoromethyl)‐5‐fluoro‐1H‐pyrazole‐4‐carboxamide

O = C(c1c(F)[NH]nc1C(F)F)N(Cc1cc(Cl)ccc1C(C)CO)C1CC1

PEDLIUVLEKOYPV‐UHFFFAOYSA‐N

graphic file with name EFS2-20-e07328-g030.jpg
M07

N‐{[5‐chloro‐2‐(1,2‐dihydroxypropan‐2‐yl)phenyl]methyl}‐N‐cyclopropyl‐3‐(difluoromethyl)‐5‐fluoro‐1H‐pyrazole‐4‐carboxamide

O = C(c1c(F)[NH]nc1C(F)F)N(Cc1cc(Cl)ccc1C(C)(O)CO)C1CC1

VELFOSPEHKZBRI‐UHFFFAOYSA‐N

graphic file with name EFS2-20-e07328-g013.jpg
M10

2‐[4‐chloro‐2‐({cyclopropyl[3‐(difluoromethyl)‐5‐fluoro‐1‐methyl‐1H‐pyrazole‐4‐carbonyl]amino}methyl)phenyl]‐2‐hydroxypropanoic acid

FC(F)c1nn(C)c(F)c1C(=O)N(Cc1cc(Cl)ccc1C(C)(O)C(=O)O)C1CC1

AYYZWAPTXFPNLH‐UHFFFAOYSA‐N

graphic file with name EFS2-20-e07328-g001.jpg
M11

2‐[4‐chloro‐2‐({cyclopropyl[3‐(difluoromethyl)‐5‐fluoro‐1H‐pyrazole‐4‐carbonyl]amino}methyl)phenyl]propanoic acid

O = C(c1c(F)[NH]nc1C(F)F)N(Cc1cc(Cl)ccc1C(C)C(=O)O)C1CC1

MYSBOVXTSKIGOQ‐UHFFFAOYSA‐N

graphic file with name EFS2-20-e07328-g028.jpg
M12

2‐[4‐chloro‐2‐({cyclopropyl[3‐(difluoromethyl)‐5‐fluoro‐1‐methyl‐1H‐pyrazole‐4‐carbonyl]amino}methyl)phenyl]propanoic acid

FC(F)c1nn(C)c(F)c1C(=O)N(Cc1cc(Cl)ccc1C(C)C(=O)O)C1CC1

OMGLNQVRAOPJGW‐UHFFFAOYSA‐N

graphic file with name EFS2-20-e07328-g020.jpg
M18

N‐({5‐chloro‐2‐[1‐(hexopyranosyloxy)propan‐2‐yl]phenyl}methyl)‐N‐cyclopropyl‐3‐(difluoromethyl)‐5‐fluoro‐1‐methyl‐1H‐pyrazole‐4‐carboxamide

FC(F)c1nn(C)c(F)c1C(=O)N(Cc1cc(Cl)ccc1C(C)COC1OC(CO)C(O)C(O)C1O)C1CC1

ZGRIZDAXCQBTRM‐UHFFFAOYSA‐N

graphic file with name EFS2-20-e07328-g031.jpg
M19

2‐[4‐chloro‐2‐({cyclopropyl[3‐(difluoromethyl)‐5‐fluoro‐1‐methyl‐1H‐pyrazole‐4‐carbonyl]amino}methyl)phenyl]propyl D‐glucopyranosiduronic acid

FC(F)c1nn(C)c(F)c1C(=O)N(Cc1cc(Cl)ccc1C(C)COC1O[C@@H]([C@@H](O)[C@H](O)[C@H]1O)C(=O)O)C1CC1

NXQJMWUDBHPCJU‐QNOCGIROSA‐N

graphic file with name EFS2-20-e07328-g019.jpg
M20

2‐[4‐chloro‐2‐({cyclopropyl[3‐(difluoromethyl)‐5‐fluoro‐1‐methyl‐1H‐pyrazole‐4‐carbonyl]amino}methyl)phenyl]propan‐2‐yl β‐D‐glucopyranosiduronic acid

CC(C)(O[C@@H]1O[C@@H]([C@@H](O)[C@H](O)[C@H]1O)C(=O)O)c1ccc(Cl)cc1CN(C(=O)c1c(F)n(C)nc1C(F)F)C1CC1

ATWUWYHOIMNQFY‐APLYEEPTSA‐N

graphic file with name EFS2-20-e07328-g015.jpg
M21

2‐[4‐chloro‐2‐({cyclopropyl[3‐(difluoromethyl)‐5‐fluoro‐1‐methyl‐1H‐pyrazole‐4‐carbonyl]amino}methyl)phenyl]propyl 6‐O‐(carboxyacetyl)hexopyranoside

FC(F)c1nn(C)c(F)c1C(=O)N(Cc1cc(Cl)ccc1C(C)COC1OC(COC(=O)CC(=O)O)C(O)C(O)C1O)C1CC1

YMALPXVTVDULQT‐UHFFFAOYSA‐N

graphic file with name EFS2-20-e07328-g017.jpg
M22

2‐[4‐chloro‐2‐({cyclopropyl[3‐(difluoromethyl)‐5‐fluoro‐1‐methyl‐1H‐pyrazole‐4‐carbonyl]amino}methyl)phenyl]propan‐2‐yl 6‐O‐(carboxyacetyl)hexopyranoside

CC(C)(OC1OC(COC(=O)CC(=O)O)C(O)C(O)C1O)c1ccc(Cl)cc1CN(C(=O)c1c(F)n(C)nc1C(F)F)C1CC1

YFINTVDEQJHUBQ‐UHFFFAOYSA‐N

graphic file with name EFS2-20-e07328-g010.jpg
M36

N‐{[5‐chloro‐2‐(1,2‐dihydroxypropan‐2‐yl)phenyl]methyl}‐N‐cyclopropyl‐3‐(difluoromethyl)‐5‐fluoro‐1‐D‐glucopyranuronosyl‐1H‐pyrazole‐4‐carboxamide

CC(O)(CO)c1ccc(Cl)cc1CN(C1CC1)C(=O)c1c(nn(C2O[C@@H]([C@@H](O)[C@H](O)[C@H]2O)C(=O)O)c1F)C(F)F

QVFQBXXQPXJYKT‐FIERSJMVSA‐N

graphic file with name EFS2-20-e07328-g006.jpg
M37

N‐{[5‐chloro‐2‐(1‐hydroxypropan‐2‐yl)phenyl]methyl}‐N‐cyclopropyl‐3‐(difluoromethyl)‐5‐fluoro‐1‐D‐glucopyranuronosyl‐1H‐pyrazole‐4‐carboxamide

CC(CO)c1ccc(Cl)cc1CN(C1CC1)C(=O)c1c(nn(C2O[C@@H]([C@@H](O)[C@H](O)[C@H]2O)C(=O)O)c1F)C(F)F

ZSRYNFOARFWRTN‐WUVSAPJJSA‐N

graphic file with name EFS2-20-e07328-g022.jpg
M41

2‐[4‐chloro‐2‐({cyclopropyl[3‐(difluoromethyl)‐5‐fluoro‐1H‐pyrazole‐4‐carbonyl]amino}methyl)phenyl]propyl 6‐O‐(carboxyacetyl)hexopyranoside

FC(F)c1n[NH]c(F)c1C(=O)N(Cc1cc(Cl)ccc1C(C)COC1OC(COC(=O)CC(=O)O)C(O)C(O)C1O)C1CC1

QSAYSOVDHNPHEP‐UHFFFAOYSA‐N

graphic file with name EFS2-20-e07328-g027.jpg
M44

γ‐glutamyl‐S‐{4‐[{[5‐chloro‐2‐(propan‐2‐yl)phenyl]methyl}(cyclopropyl)carbamoyl]‐3‐(difluoromethyl)‐1‐methyl‐1H‐pyrazol‐5‐yl}cysteinyl‐β‐alanine

FC(F)c1nn(C)c(SCC(NC(=O)CCC(N)C(=O)O)C(=O)NCCC(=O)O)c1C(=O)N(Cc1cc(Cl)ccc1C(C)C)C1CC1

FLNRZLRDOXPINC‐UHFFFAOYSA‐N

graphic file with name EFS2-20-e07328-g012.jpg
M45

N‐(carboxyacetyl)‐S‐{4‐[{[5‐chloro‐2‐(propan‐2‐yl)phenyl]methyl}(cyclopropyl)carbamoyl]‐3‐(difluoromethyl)‐1‐methyl‐1H‐pyrazol‐5‐yl}cysteine

FC(F)c1nn(C)c(SCC(NC(=O)CC(=O)O)C(=O)O)c1C(=O)N(Cc1cc(Cl)ccc1C(C)C)C1CC1

DMLPCMKVBJJXFK‐UHFFFAOYSA‐N

graphic file with name EFS2-20-e07328-g004.jpg
M46 Structure undefined, a unique name/SMILES/InChiKey cannot be allocated graphic file with name EFS2-20-e07328-g014.jpg
M47

3‐({4‐[{[5‐chloro‐2‐(propan‐2‐yl)phenyl]methyl}(cyclopropyl)carbamoyl]‐3‐(difluoromethyl)‐1‐methyl‐1H‐pyrazol‐5‐yl}sulfanyl)‐2‐(hexopyranosyloxy)propanoic acid

CC(C)c1ccc(Cl)cc1CN(C1CC1)C(=O)c1c(nn(C)c1SCC(OC1OC(CO)C(O)C(O)C1O)C(=O)O)C(F)F

UZIHNDQMMSECCA‐UHFFFAOYSA‐N

graphic file with name EFS2-20-e07328-g018.jpg
M48 Structure undefined, a unique name/SMILES/InChiKey cannot be allocated graphic file with name EFS2-20-e07328-g033.jpg
M49

N‐cyclopropyl‐3‐(difluoromethyl)‐5‐fluoro‐1‐methyl‐1H‐pyrazole‐4‐carboxamide

FC(F)c1nn(C)c(F)c1C(=O)NC1CC1

RPDXNEFSTLSRNP‐UHFFFAOYSA‐N

graphic file with name EFS2-20-e07328-g035.jpg
M50

3‐(difluoromethyl)‐5‐fluoro‐1‐methyl‐1H‐pyrazole‐4‐carboxylic acid

FC(F)c1nn(C)c(F)c1C(=O)O

AXJCNOQHTJLWDH‐UHFFFAOYSA‐N

graphic file with name EFS2-20-e07328-g025.jpg
M52 Structure undefined, a unique name/SMILES/InChiKey cannot be allocated graphic file with name EFS2-20-e07328-g023.jpg
M54 Structure undefined, a unique name/SMILES/InChiKey cannot be allocated graphic file with name EFS2-20-e07328-g007.jpg
M57 Structure undefined, a unique name/SMILES/InChiKey cannot be allocated graphic file with name EFS2-20-e07328-g008.jpg
M58

N‐cyclopropyl‐3‐(difluoromethyl)‐5‐fluoro‐1H‐pyrazole‐4‐carboxamide

O = C(NC1CC1)c1c(F)[NH]nc1C(F)F

PZVFCYMYIARZJC‐UHFFFAOYSA‐N

graphic file with name EFS2-20-e07328-g034.jpg
M62 Structure undefined, a unique name/SMILES/InChiKey cannot be allocated graphic file with name EFS2-20-e07328-g032.jpg
M66

3‐[4‐(cyclopropylcarbamoyl)‐3‐(difluoromethyl)‐5‐fluoro‐1H‐pyrazol‐1‐yl]alanine

NC(Cn1nc(C(F)F)c(c1F)C(=O)NC1CC1)C(=O)O

VIXFWVNWSIKQNG‐UHFFFAOYSA‐N

graphic file with name EFS2-20-e07328-g024.jpg
M67

3‐[4‐(cyclopropylcarbamoyl)‐3‐(difluoromethyl)‐1H‐pyrazol‐1‐yl]alanine

NC(Cn1cc(c(n1)C(F)F)C(=O)NC1CC1)C(=O)O

MTKWGTYFOHNAJD‐UHFFFAOYSA‐N

graphic file with name EFS2-20-e07328-g026.jpg
M77

N‐{[5‐chloro‐2‐(1‐hydroxypropan‐2‐yl)phenyl]methyl}‐N‐cyclopropyl‐5‐fluoro‐3‐formyl‐1H‐pyrazole‐4‐carboxamide

O = C(c1c(F)[NH]nc1C=O)N(Cc1cc(Cl)ccc1C(C)CO)C1CC1

GTFGDIVWVRNVNC‐UHFFFAOYSA‐N

graphic file with name EFS2-20-e07328-g003.jpg
M69 Structure undefined, a unique name/SMILES/InChiKey cannot be allocated graphic file with name EFS2-20-e07328-g011.jpg
(a)

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

(b)

ACD/Name 2021.1.3 ACD/Labs 2021.1.3 (File Version N15E41, Build 123232, 7 July 2021).

(c)

ACD/ChemSketch 2021.1.3 ACD/Labs 2021.1.3 (File Version C25H41, Build 123835, 28 August 2021).