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. 2020 Jan 20;25(2):422. doi: 10.3390/molecules25020422

Table 1.

The structure, IC50 for anti-thrombin and docking score of 42 compounds.

graphic file with name molecules-25-00422-i001.jpg

No. Compound R1 R2 R3 R4 R5 R6 R7 R8 R9 IC50(μM) -CDOCKER_
Energy
(Kcal/mol)		 -CDOCKER_INTERACTION_
Energy
(Kcal/mol)
flavonol
1 Galangin OH OH H OH H H H H H 159 ± 0 27.5 32.1
2 Herbacetin OH OH H OH OH H H OH H 133 ± 4 31.0 31.2
3 Kaempferol OH OH H OH H H H OH H 107 ± 2 33.6 40.2
4 Astragaline O-glc OH H OH H H H OH H 217 ± 5 7.92 46.8
5 Kaempferol-7-O-β-D-
glucopyranoside		 OH OH H O-glc H H H OH H >500 22.6 48.5
6 Morin OH OH H OH H OH H OH H 237 ± 26 33.0 39.3
7 Fisetin OH H H OH H H OH OH H 175 ± 18 33.4 36.2
8 Quercetin OH OH H OH H H OH OH H 205 ± 14 32.2 34.3
9 Quercitrin O-rha OH H OH H H OH OH H >500 17.5 51.2
10 Isoquercitrin O-glc OH H OH H H OH OH H >500 13.6 58.8
11 Rutin O-rut OH H OH H H OH OH H 274 ± 23 5.76 61.7
12 Isorhamnetin OH OH H OH H H OCH3 OH H 72.2 ± 4.8 29.2 35.1
13 Isorhamnetin-3-O-
neohesperidoside		 O-glc-rha OH H OH H H OCH3 OH H >500 5.76 57.2
14 Typhaneoside O-rha-(glc)2 OH H OH H H OCH3 OH H >500 2.97 75.8
15 Myricetin OH OH H OH H H OH OH OH 56.5 ± 2.1 36.2 37.7
16 Myricitrin O-rha OH H OH H H OH OH OH 79.5 ± 3.4 17.4 50.3
flavone
17 Chrysin H OH H OH H H H H H >500 25.5 30.3
18 Baicalein H OH OH OH H H H H H 249 ± 31 28.7 28.5
19 Baicalin H OH OH O-glc H H H H H 88.6 ± 8.2 20.5 40.0
20 Wogonin H OH H OH OCH3 H H H H >500 20.1 28.6
21 Wogonoside H OH H O-glu OCH3 H H H H >500 29.5 38.2
22 Hispidulin H OH OCH3 OH H H H OH H 126 ± 6 29.5 38.2
23 Scutellarein H OH OH OH H H H OH H 70.8 ± 2.7 35.1 35.7
24 Apigenin H OH H OH H H H OH H 96.2 ± 10.0 25.9 30.8
25 Genkwanin H OH H OCH3 H H H OH H 212 ± 30 26.1 33.2
26 Hydroxygenkwanin H OH H OCH3 H H OH OH H 99.7 ± 5.5 33.6 38.6
27 Luteolin H OH H OH H H OH OH H 146 ± 10 31.5 36.6
28 Luteoloside H OH H O-glc H H OH OH H 155 ± 18 14.1 45.4
29 Diosmetin H OH H OH H H OH OCH3 H 131 ± 14 31.41 38.4
30 6-Methoxyluteolin H OH OCH3 OH H H OH OH H >500 31.0 38.7
graphic file with name molecules-25-00422-i002.jpg
flavanonol
31 Dihydroquercetin OH OH H OH H H OH OH H >500 34.4 39.7
32 Dihydromyricetin
flavanone		 OH OH H OH H H OH OH OH >500 40.3 43.3
33 Naringenin H OH H OH H H H OH H >500 30.3 35.5
34 Naringin H OH H O-glu-rha H H H OH H 444 ± 59 7.6 56.3
35 Narirutin H OH H O-rut H H H OH H >500 10.8 55.7
36 Hesperetin H OH H OH H H OH OCH3 H >500 35.5 41.9
37 Hesperidin H OH H O-glu-rha H H OH OCH3 H >500 6.28 60.1
38 Neohesperidin H OH H O-(glc)2 H H OH H OCH3 >500 8.64 55.2
graphic file with name molecules-25-00422-i003.jpg
Catechins
39 Epicatechin OH↑ H OH H OH H H OH OH >500 31.5 36.5
40 (-)-epigallocatechin OH↓ H OH H OH H H OH OH >500 33.4 39.3
41 (-)-Epicatechin gallate 1* H OH H OH H H OH OH >500 52.1 54.6
42 Proanthocyanidin B1 OH 2* OH H OH H H OH OH >500.0 42.4 55.9
Argatroban - - - - - - - - - 1.86 ± 0.10 - -

1* Inline graphic; 2* Inline graphic; glc, glucose; glu, glucuronic acid; rha, rhamnose; rut, rutinose.