Table 2.
The bonding energies (kcal/mol) and the detailed interactions of all synthesized compounds on 3EQM target using AutoDock Vina
| Entry | Amino Acid | Ligand involved moiety | Type of interaction | B.E (kcal/mol) | Entry | Amino Acid | Ligand involved moiety | Type of interaction | B.E (kcal/mol) |
|---|---|---|---|---|---|---|---|---|---|
| 7a | Met 374 | benzyl | pi-sulfur | − 9.9 | 10c | HEM 600 | benzoyl | pi-cation | − 9.2 |
| Leu 477, Ile 133, Ala 306, Val 370 | 1,2,4-triazole & benzoyl | pi-alkyl | Phe 134, Phe 221 | 1,2,4-triazole & benzoyl | pi-pi | ||||
| HEM 600 | benzoyl | pi-cation | Leu 372, Ser 478 | 1,2,4-triazole & C = O | Carbon hydrogen bond | ||||
| Thr 310, Arg 115, Val 373, Phe 134, Leu 372, Phe 221, Ser 478, Trp 224 | – | Vander waals | Ala 306, Ile 133, Val 370, Met 374 | benzoyl & 1,2,4-triazole | pi-alkyl & alkyl | ||||
| 7b | Val 370, Leu 477, Val 373, Ala 306, Ile 133, Ile 305, Phe 221, Trp 224 | benzyl & benzoyl & 1,2,4-triazole | pi-alkyl & alkyl | − 10.5 | Arg 115, Trp 224, Val 373, Thr 310, Leu 477, Asp 309 | – | Vander waals | ||
| HEM 600 | benzyl & benzoyl | pi-pi | 10d | Ala 306 | benzoyl | halogen | − 7.9 | ||
| Arg 115 | benzyl | pi-cation | HEM 600 | benzoyl | pi-cation | ||||
| Glu 302, Ser 478, Phe 134, Met 374, Leu 372, Thr 310, Asp 309 | – | Vander waals | Leu 477 | benzoyl | pi-sigma | ||||
| 7c | Tyr 424 | di-phenyl | pi-pi | − 8.2 | Phe 221 | benzoyl | pi-pi | ||
| Lys 440 | di-phenyl | pi-cation | Val 370, Val 369, Leu 372, Met 374, Ile 133, HEM 600, Phe 221 | benzoyl & 1,2,4-triazole | alkyl & pi-alkyl | ||||
| Phe 418, Val 422, Tyr 361, Pro 429 | benzoyl & di-phenyl | pi-alkyl &| alkyl | Asp 309, Ser 478, Phe 134, Trp 224, Thr 310, Val 373, Arg 115 | – | Vander waals | ||||
| Asn 421, Lys 354, Glu 357, Phe 427, Phe 430, Met 444, Gln 428, Phe 432, Tyr 441 | – | Vander waals | 10e | Arg 115 | 1,2,4- triazole | Hydrogen bond | − 9.7 | ||
| 7d | Lys 440 | di-phenyl | pi-alkyl | − 7.9 | Ser 478 | C = O | Carbon hydrogen bond | ||
| Tyr 424, Tyr 441 | benzoyl & di-phenyl | pi-pi | HEM 600 | benzoyl | pi-cation | ||||
| Gln 428 | C = O | Hydrogen bond | HEM 600 | benzoyl | pi-sigma | ||||
| Phe 432, Phe 430, Met 444, Tyr 361, Pro 429, Phe 427, Val 422, Phe 418 | – | Vander waals | Ile 133, Phe 134, Ala 306, Val 370, Met 374, Val 373 | benzoyl & 1,2,4-triazole | alkyl & pi-alkyl | ||||
| 7e | Tyr 441, Phe 430, Met 444, Lys 440, Pro 429 | 1,2,4-triazole & benzoyl | pi-alkyl & alkyl | − 7.3 | Leu 372, Leu 477, Phe 221, Asp 309, Trp 224, Thr 310 | – | Vander waals | ||
| Tyr 424 | di-phenyl | pi-pi | 10f | Lys 440 | C = O | Carbon hydrogen bond | − 8.9 | ||
| Lys 440 | 1,2,4-triazole | pi-cation | Tyr 361 | benzoyl | pi-pi | ||||
| Pro 429 | 1,2,4-triazole | Carbon hydrogen bond | Tyr 424 | phenyl | pi-pi | ||||
| Lys 440 | 1,2,4-triazole | Hydrogen bond | Pro 429 | benzoyl | pi-alkyl | ||||
| Phe 432, Gln 428, Phe 427 | – | Vander waals | Val 422, Phe 427, Phe 432, Gln 428, Met 444, Phe 430, Tyr 441 | – | Vander waals | ||||
| 8a | Arg 115 | benzyl | pi-cation | 9.4 | 10 g | Tyr 424 | phenyl | pi-pi | − 7.5 |
| HEM 600 | benzyl | pi-pi | Pro 429 | benzoyl | pi-alkyl | ||||
| Met 374, Ala 306, Thr 310, Ile 133, Trp 224, Phe 221, Ser 478, Phe 134, Leu 372 | – | Vander waals | Phe 418, Tyr 361, Tyr 441, Lys 440, Phe 430, Phe 432, Gln 428, Val 422, Phe 427 | – | Vander waals | ||||
| Val 373, Val 370, Leu 477 | benzyl | pi-alkyl | 10 h | Glu 357 | benzoyl | pi-anion | -7.2 | ||
| 8b | Phe 432, Tyr 424, Pro 429, Met 444 | benzyl & di-phenyl | pi-alky | − 7.8 | Tyr 424, Tyr 361 | benzoyl & phenyl | pi-pi | ||
| Tyr 424, Tyr 441 | benzyl & di-phenyl | pi-pi | Val 422 | benzoyl | pi-alkyl | ||||
| Tyr 361 | di-phenyl | pi-donor hydrogen bond | Phe 432, Tyr 441, Lys 440, Gln 428, Phe 430, Pro 429, Phe 427, Phe 418, Lys 354, Asn 421 | – | Vander waals | ||||
| Phe 427, Gln 428, Gly 433, Lys 440, Phe 430 | – | Vander waals | 10i | Tyr 244 | 1,2,4-triazole | Hydrogen bond | − 6.7 | ||
| 8c | Met 444, Val 422, Tyr 441 | benzyl & di-phenyl | pi-alkyl & alkyl | − 7.8 | Asp 476 | phenyl | pi-anion | ||
| Tyr 441, Tyr 424 | benzyl & 1,2,4-triazole | pi-pi | Ile 474 | benzoyl | pi-sigma | ||||
| Tyr 361 | benzyl | pi-donor hydrogen bond | Ala 226, Ile 474 | 1,2,4-triazole & benzoyl | alkyl & pi-alkyl | ||||
| Lys 440 | 1,2,4-triazole | pi-cation | His 475, Gln 225, Lys 230, Gly 69, Ile 229, Phe 65, Leu 66, Trp 67 | – | Vander waals | ||||
| Phe 430, Phe 418, Phe 427, Asn 421, Gln 428, Phe 432 | – | Vander waals | 10j | Lys 440, Gln 428 | 1,2,4-triazole & C = O | Hydrogen bond | − 7.8 | ||
| 10a | Ser 478 | C = O | Carbon hydrogen bond | − 9.4 | Lys 440 | 1,2,4-triazole | pi-cation | ||
| HEM 600 | 1,2,4-triazole | pi-cation | Tyr 361 | phenyl | pi-donor hydrogen bond | ||||
| Leu 477 | benzoyl | pi-sigma | Tyr 424, Tyr 441 | benzoyl & 1,2,4-triazole & phenyl | pi-pi | ||||
| HEM 600 | benzoyl | pi-pi | Pro 429, Met 444 | Benzoyl & phenyl | pi-alkyl | ||||
| Val 373, Ile 133, Val 370, Ala 306 | 1,2,4-triazole & benzoyl | pi-alkyl | Phe 432, Val 422, Phe 418, Phe 427, Phe 430, | ––- | Vander waals | ||||
| Arg 115, Met 374, Phe 221, Leu 372, Phe 134, Thr 310, Trp 224 | – | Vander waals | 10 k | Asn 421 | 1,2,4-triazole | Hydrogen bond | − 7.3 | ||
| 10b | Met 374 | benzoyl | pi-sulfur | − 9.3 | Glu 357 | phenyl | pi-anion | ||
| HEM 600 | 1,2,4-triazole | pi-cation | Tyr 361 | phenyl | pi-pi | ||||
| Phe 221, Val 370, Val 369, Ala 306, Ile 133 | 1,2,4-triazole & benzoyl | alkyl & pi-alkyl | Tyr 424, Lys 440, Tyr 441, Phe 430, Pro 429 | benzoyl | alkyl & pi-alkyl | ||||
| Thr 310, Asp 309, Ser 478, Trp 224, Leu 477, Phe 134, Arg 115, Val 373, Leu 372 | – | Vander waals | Met 444, Lys 354, Phe 418, Gln 428, Phe 427, Val 422, | – | Vander waals |