Marvin 09271212302D 29 30 0 0 0 0 999 V2000 6.3282 -7.9769 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3270 -8.8043 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0419 -9.2171 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7583 -8.8038 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7554 -7.9733 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0401 -7.5641 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6123 -9.2162 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6116 -10.0412 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.8968 -10.4531 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 6.3257 -10.4543 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3251 -11.2793 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.1827 -10.0401 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4679 -10.4520 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1833 -9.2151 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6391 -10.4514 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0510 -11.1662 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9213 -10.8561 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2111 -10.4363 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9129 -11.6811 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.0405 -10.0423 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 7.7547 -10.4554 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.4695 -10.0435 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.1836 -10.4565 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.8984 -10.0446 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.6126 -10.4577 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 11.3274 -10.0457 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.0415 -10.4588 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.7563 -10.0468 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 13.4704 -10.4599 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 15 13 1 0 0 0 0 16 15 1 0 0 0 0 13 16 1 0 0 0 0 2 7 1 0 0 0 0 3 4 2 0 0 0 0 8 7 1 1 0 0 0 15 17 1 0 0 0 0 17 18 1 0 0 0 0 8 9 1 0 0 0 0 17 19 2 0 0 0 0 4 5 1 0 0 0 0 10 20 1 0 0 0 0 8 10 1 0 0 0 0 20 21 1 0 0 0 0 2 3 1 0 0 0 0 21 22 1 0 0 0 0 10 11 2 0 0 0 0 22 23 1 0 0 0 0 5 6 2 0 0 0 0 23 24 1 0 0 0 0 9 12 1 0 0 0 0 24 25 1 0 0 0 0 6 1 1 0 0 0 0 25 26 1 0 0 0 0 12 13 1 0 0 0 0 26 27 1 0 0 0 0 1 2 2 0 0 0 0 27 28 1 0 0 0 0 12 14 2 0 0 0 0 28 29 1 0 0 0 0 M END > CHEBI:66241 > TMC-52D > An epoxide which is a carboxamide obtained by the formal condensation of one of the carboxy groups of oxirane-2,3-dicarboxylic acid with N-{4-[(3-aminopropyl)amino]butyl}-L-phenylalaninamide. It is a natural product, isolated from Gliocladium sp. F-2665. TMC-52D acts as an inhibitor of cysteine proteinases, particularly cathepsin B (EC 3.4.22.1), cathepsin L (EC 3.4.22.15), and papain (EC 3.4.22.2), with IC50 values of 280 nM, 6 nM, and 49 nM, respectively. The epoxide group has trans configuration but its exact stereochemistry is uncertain: it is either (2R,3R) or (2S,3S). > 3 > (2R*,3R*)-3-{[(2S)-1-({4-[(3-aminopropyl)amino]butyl}amino)-1-oxo-3-phenylpropan-2-yl]carbamoyl}oxirane-2-carboxylic acid > C20H30N4O5 > 406.47600 > 406.22162 > 0 > NCCCNCCCCNC(=O)[C@H](Cc1ccccc1)NC(=O)C1OC1C(O)=O > InChI=1S/C20H30N4O5/c21-9-6-11-22-10-4-5-12-23-18(25)15(13-14-7-2-1-3-8-14)24-19(26)16-17(29-16)20(27)28/h1-3,7-8,15-17,22H,4-6,9-13,21H2,(H,23,25)(H,24,26)(H,27,28)/t15-,16?,17?/m0/s1 > VMUJCCBLIGGNAX-GTPINHCMSA-N > 8169487 > 9727388 $$$$