NPASS Compound

Natural Product: NPC141957

Natural Product ID	NPC141957
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Cycloleonuripeptide F
IUPAC Name	n.a.
Synonyms	Cycloleonuripeptide F
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL503303
PubChem CID	11651008
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0000265] Carboxylic acids and derivatives [CHEMONTID:0000013] Amino acids, peptides, and analogues [CHEMONTID:0000348] Peptides [CHEMONTID:0004831] Oligopeptides

The Chemical Classification was calculated by Classyfire, a software for chemical taxonomy calculation. Reference: DOI:10.1186/s13321-016-0174-y.

Chemical Representations

RDKit 3D 144151 0 0 0 0 0 0 0 0999 V2000 3.6380 -8.0268 -2.0465 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7939 -6.4968 -1.8267 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9096 -6.4029 -0.7988 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4857 -6.0263 -1.3229 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3999 -4.5150 -1.0615 C 0 0 1 0 0 0 0 0 0 0 0 0 1.0051 -4.2488 -0.5367 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0592 -4.3148 -1.3282 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6688 -3.9350 0.7740 N 0 0 0 0 0 0 0 0 0 0 0 0 1.4417 -3.7868 1.9405 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6013 -4.2421 3.1127 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7634 -4.4614 2.5195 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7096 -3.7186 1.1731 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.0469 -2.2906 1.4036 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0031 -1.6499 0.8683 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.9648 -2.1688 -0.0789 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.0273 -3.0213 0.5494 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8188 -2.2704 1.5643 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4828 -2.2131 2.8947 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1894 -1.5319 3.8377 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3186 -0.8526 3.4339 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7063 -0.8757 2.0963 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9651 -1.5764 1.1740 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5985 -1.0267 -0.8185 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4769 0.1796 -0.4244 N 0 0 0 0 0 0 0 0 0 0 0 0 -4.0725 1.2948 -1.1180 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.5868 1.1837 -0.9384 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2820 2.3016 -1.6308 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5403 3.5189 -1.0527 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.2001 4.5224 -1.7412 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.6235 4.3281 -3.0463 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.3698 3.1111 -3.6371 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7035 2.1090 -2.9288 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.2863 5.3364 -3.7360 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5667 2.5185 -0.4544 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3169 3.5116 -1.1471 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3348 2.6976 0.9354 N 0 0 0 0 0 0 0 0 0 0 0 0 -3.6540 1.8629 1.9855 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9533 2.4050 3.2019 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2941 3.6810 2.7784 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7349 3.9149 1.3896 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6227 4.3198 0.4980 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7431 3.4896 0.2920 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4699 5.5257 -0.1222 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.1757 6.7462 -0.1094 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0639 7.7393 0.2522 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1072 7.1847 -0.5698 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3454 5.8312 -1.0466 C 0 0 1 0 0 0 0 0 0 0 0 0 0.6890 4.8140 -1.0044 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6521 3.8612 -1.8342 N 0 0 0 0 0 0 0 0 0 0 0 0 1.4791 2.7401 -2.0518 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7923 2.9700 -2.6541 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9103 2.5217 -2.4064 N 0 0 0 0 0 0 0 0 0 0 0 0 4.5345 1.6236 -1.5063 C 0 0 1 0 0 0 0 0 0 0 0 0 4.6528 2.1730 -0.1247 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2992 1.3297 0.8854 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6774 1.3512 1.1073 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2763 0.5936 2.0727 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5443 -0.2321 2.8788 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1738 -0.2823 2.6907 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5743 0.4855 1.7130 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1435 -1.0092 3.8664 O 0 0 0 0 0 0 0 0 0 0 0 0 4.0105 0.2495 -1.6173 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8234 0.0561 -1.9140 O 0 0 0 0 0 0 0 0 0 0 0 0 4.7325 -0.9324 -1.4275 N 0 0 0 0 0 0 0 0 0 0 0 0 6.1071 -1.1477 -1.1620 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4773 -2.4162 -1.9386 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1494 -2.8689 -2.5675 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1578 -2.2582 -1.5566 C 0 0 1 0 0 0 0 0 0 0 0 0 4.1639 -3.0482 -0.3172 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3616 -4.0495 -0.1363 N 0 0 0 0 0 0 0 0 0 0 0 0 5.0171 -2.7972 0.7514 O 0 0 0 0 0 0 0 0 0 0 0 0 2.7675 3.9015 -3.7558 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6973 4.8890 -0.0711 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3285 -1.3249 -1.9520 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2364 -1.5918 2.2903 O 0 0 0 0 0 0 0 0 0 0 0 0 4.6137 -8.5018 -1.9605 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0132 -8.3725 -1.2016 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1572 -8.1780 -3.0294 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0879 -6.0596 -2.7729 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5391 -6.6197 0.2252 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6238 -7.2493 -1.0410 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5085 -5.5031 -0.8433 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1170 -6.5974 -0.4362 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7274 -6.2163 -2.1346 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4234 -4.0573 -2.0678 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8310 -2.7545 2.0999 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3003 -4.5223 1.9063 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5610 -3.4157 3.8806 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9987 -5.1143 3.6298 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5161 -3.9757 3.1667 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0466 -5.5038 2.3899 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3456 -4.1954 0.4073 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3913 -2.7548 -0.8178 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7288 -3.3446 -0.2734 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6583 -3.9384 1.0012 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5995 -2.7473 3.2056 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8713 -1.5209 4.8924 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9164 -0.2910 4.1607 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.6030 -0.3180 1.8531 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2764 -1.5921 0.1323 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7904 1.2297 -2.1674 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9989 0.2474 -1.3582 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8432 1.1538 0.1509 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2173 3.6817 -0.0472 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4132 5.4820 -1.3110 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.7026 2.9705 -4.6571 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5263 1.1582 -3.4506 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.2227 5.6262 -3.5305 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4142 0.7738 1.8396 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7844 1.9433 2.1572 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1460 1.6595 3.4674 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6504 2.5427 4.0572 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1854 3.6532 2.9066 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6357 4.4692 3.5004 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4538 4.7693 1.3979 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0018 6.8020 0.6285 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5204 7.0297 -1.1303 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3248 8.7559 -0.0327 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8976 7.5950 1.3435 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2124 7.8930 -1.4447 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0271 7.1445 0.0373 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8139 5.9538 -2.0662 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9229 1.9914 -2.6666 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6504 2.2813 -1.0290 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6176 1.5340 -1.8754 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6106 2.3927 0.2477 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2291 3.1483 -0.1550 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2425 2.0184 0.4521 H 0 0 0 0 0 0 0 0 0 0 0 0 8.3439 0.6560 2.1926 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6123 -0.9406 3.3380 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4910 0.3955 1.6235 H 0 0 0 0 0 0 0 0 0 0 0 0 8.1099 -0.9282 4.0708 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6938 -0.3351 -1.6926 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3859 -1.2180 -0.1130 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8558 -3.1722 -1.2222 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1687 -2.2385 -2.7586 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1517 -3.9555 -2.5640 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9460 -2.3830 -3.5205 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1531 -2.1732 -1.9761 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7658 -3.0727 1.6916 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6216 4.4648 -3.8932 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6117 4.5162 -0.2023 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3309 -0.6964 -2.7544 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4968 -0.7379 2.7318 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 2 4 1 0 4 5 1 0 5 6 1 0 6 7 2 0 6 8 1 0 8 9 1 0 9 10 1 0 10 11 1 0 11 12 1 0 12 13 1 0 13 14 2 3 14 15 1 0 15 16 1 0 16 17 1 0 17 18 2 0 18 19 1 0 19 20 2 0 20 21 1 0 21 22 2 0 15 23 1 0 23 24 2 3 24 25 1 0 25 26 1 0 26 27 1 0 27 28 2 0 28 29 1 0 29 30 2 0 30 31 1 0 31 32 2 0 30 33 1 0 25 34 1 0 34 35 2 0 34 36 1 0 36 37 1 0 37 38 1 0 38 39 1 0 39 40 1 0 40 41 1 0 41 42 2 0 41 43 1 0 43 44 1 0 44 45 1 0 45 46 1 0 46 47 1 0 47 48 1 0 48 49 2 3 49 50 1 0 50 51 1 0 51 52 2 3 52 53 1 0 53 54 1 0 54 55 1 0 55 56 2 0 56 57 1 0 57 58 2 0 58 59 1 0 59 60 2 0 58 61 1 0 53 62 1 0 62 63 2 0 62 64 1 0 64 65 1 0 65 66 1 0 66 67 1 0 67 68 1 0 68 69 1 0 69 70 2 3 69 71 1 0 51 72 1 0 48 73 1 0 23 74 1 0 13 75 1 0 70 5 1 0 12 8 1 0 22 17 1 0 32 27 1 0 40 36 1 0 47 43 1 0 60 55 1 0 68 64 1 0 1 76 1 0 1 77 1 0 1 78 1 0 2 79 1 0 3 80 1 0 3 81 1 0 3 82 1 0 4 83 1 0 4 84 1 0 5 85 1 6 9 86 1 0 9 87 1 0 10 88 1 0 10 89 1 0 11 90 1 0 11 91 1 0 12 92 1 6 15 93 1 6 16 94 1 0 16 95 1 0 18 96 1 0 19 97 1 0 20 98 1 0 21 99 1 0 22100 1 0 25101 1 6 26102 1 0 26103 1 0 28104 1 0 29105 1 0 31106 1 0 32107 1 0 33108 1 0 37109 1 0 37110 1 0 38111 1 0 38112 1 0 39113 1 0 39114 1 0 40115 1 1 44116 1 0 44117 1 0 45118 1 0 45119 1 0 46120 1 0 46121 1 0 47122 1 6 50123 1 0 50124 1 0 53125 1 6 54126 1 0 54127 1 0 56128 1 0 57129 1 0 59130 1 0 60131 1 0 61132 1 0 65133 1 0 65134 1 0 66135 1 0 66136 1 0 67137 1 0 67138 1 0 68139 1 6 71140 1 0 72141 1 0 73142 1 0 74143 1 0 75144 1 0 M END

Standard InCHIKey	KUJSGRJPNYKNOJ-QVWIHFFISA-N
Standard InCHI	InChI=1S/C55H69N9O11/c1-33(2)28-40-52(72)61-24-7-13-44(61)50(70)58-39(29-34-10-4-3-5-11-34)48(68)59-42(31-36-18-22-38(66)23-19-36)54(74)64-27-9-15-46(64)55(75)63-26-6-12-43(63)49(69)56-32-47(67)57-41(30-35-16-20-37(65)21-17-35)53(73)62-25-8-14-45(62)51(71)60-40/h3-5,10-11,16-23,33,39-46,65-66H,6-9,12-15,24-32H2,1-2H3,(H,56,69)(H,57,67)(H,58,70)(H,59,68)(H,60,71)/t39-,40-,41-,42-,43-,44-,45-,46-/m0/s1
SMILES	CC(C)C[C@H]1C(=O)N2CCC[C@H]2C(=N[C@@H](Cc2ccccc2)C(=N[C@@H](Cc2ccc(cc2)O)C(=O)N2CCC[C@H]2C(=O)N2CCC[C@H]2C(=NCC(=N[C@@H](Cc2ccc(cc2)O)C(=O)N2CCC[C@H]2C(=N1)O)O)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	1031.51	Volume:	1039.591 ? Van der Waals volume.
Dense:	0.992	LogP:	1.165 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.874 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.026 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	8.0	Rigid Bonds:	65.0
TPSA:	284.65 ? Topological Polar Surface Area.	H-Bond Acceptor:	20.0
H-Bond Donor:	7.0	Rings:	8.0
Heavy Atoms:	20.0

MedChem Properties

QED Drug-Likeness Score:	0.15	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	6.355	Fsp³:	0.509
MCE-18:	178.807 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected	GSK Rule:	Accepted
Golden Triangle Rule:	Accepted	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.631	Fluc inhibitor:	0.037 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.003 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.885 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.001	Promiscuous compounds:	0.007

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.081	MDCK Permeability:	-4.93
Pgp-inhibitor:	0.977	Pgp-substrate:	1.0
PAMPA:	0.096 ? The experimental data for Peff was logarithmically transformed (logPeff). Molecules with log Peff values below 2.0 were classified as low-permeability (Category 0), while those with log Peff values exceeding 2.5 were classified as high-permeability (Category 1).	Human Intestinal Absorption (HIA):	0.389
20% Bioavailability (F20%):	1.0	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.987
Plasma Protein Binding (PPB):	54.4%	Volume Distribution (VD):	-0.216
Fu:	41.088% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.999
OATP1B3 inhibitor:	0.57	BCRP inhibitor:	0.109
BSEP inhibitor:	0.999

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.302	CYP2C19-substrate:	0.016
CYP2C9-inhibitor:	0.002	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	1.0
CYP3A4-inhibitor:	1.0	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.0
HLM stability:	0.575 ? Human liver microsomal (HLM) stability. Category 0: stable+ (HLM > 30 min); Category 1: unstable- (HLM ≤ 30 min). The output value is the probability of human liver microsomal instability, where a value closer to 1 indicates a higher likelihood of instability.

ADMET: Excretion

Clearance (CL):

1.484

Half-life (T1/2):

2.931

ADMET: Toxicity

hERG Blockers:	0.0	hERG Blockers (10um):	0.0
Human Hepatotoxicity (H-HT):	1.0	Drug-induced Liver Injury (DILI):	1.0
AMES Toxicity:	0.0	Rat Oral Acute Toxicity:	0.914
Maximum Recommended Daily Dose:	1.0	Skin Sensitization:	1.0
Carcinogencity:	0.005	Eye Corrosion:	0.0
Eye Irritation:	0.0	Respiratory Toxicity:	1.0
Drug-induced Neurotoxicity:	0.986	Ototoxicity:	1.0
Hematotoxicity:	0.017	Drug-induced Nephrotoxicity:	1.0
Genotoxicity:	1.0	RPMI-8226 Immunitoxicity:	0.0
A549 Cytotoxicity:	0.0	Hek293 Cytotoxicity:	0.014
BCF:	0.516 ? Bioconcentration factors are used for considering secondary poisoning potential and assessing risks to human health via the food chain. The unit is -log10[(mg/L)/(1000*MW)].	IGC50:	3.549 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.111 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.394 ? 96 hour fathead minnow LC50. The unit of LC50FM is -log10[(mg/L)/(1000*MW)].

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO30707	Leonurus heterophyllus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16724855]
NPO30707	Leonurus heterophyllus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO30707	Leonurus heterophyllus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO30707	Leonurus heterophyllus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]

Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	Organism Name	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
Activity	1

Activity Type	# Activity
Tissue	1

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT177	Tissue	Aorta	Rattus norvegicus	Activity	=	40.0	%	PMID[16124782]

In vivo activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference

Experimental ADME

Experiment Model	Experiment Tissue	ADME Type	ADME Relation	ADME Value	ADME Unit	Reference

Experimental Toxicity

Quantitative toxicity

Experiment Model	Experiment Organism	Toxicity Type	Toxicity Relation	Toxicity Value	Toxicity Unit	Reference

Common Abbreviations:
LC: Lethal Concentration; LD: Lethal Dose; LT:Lethal Time; NOAEL: No-observed-adverse-effect Level; BMDL: Benchmark Dose Lower Confidence Limit; BMD: Benchmark Dose; BMC:Benchmark Concentration; LOAEL: Lowest Observed Adverse Effect Level; RfD:Reference Dose; RfC:Reference Concentration; MRL: Minimal Risk Level; MEG: Maximum Exposure Guideline; PAC: Protective Action Criteria

Categorical toxicity labels

Hepatotoxicity	Carcinogenicity	Mutagenicity	Cardiotoxicity	Respiratory Toxicity	Eye Irritation	Endocrine Disruption

Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP toxicity records from domain-specific databases. These databases include:
☉ ToxValDB: a curated database that compiles quantitative toxicity values for chemicals from diverse public sources to support toxicological research and risk assessment.
☉ TOXRIC: a comprehensive, free-to-access, online database providing toxicological/feature data. The toxicity labels are retrieved from this database. [PMID: 36400569]

Chemically structural similarity

Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes approximately 50,000 NPs with experimentally-derived bioactivity available in NPASS)

Similarity is measured using the Tanimoto coefficient (Tc) , which compares the binary fingerprints of two molecules. Tc is calculated as the intersection divided by the union of '1' bits in the fingerprints, ranging from 0 to 1, with 1 indicating highest similarity.

● The left chart: Distribution of similarity level between NPC141957 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	16679
0.1-0.2	30807
0.2-0.3	1897
0.3-0.4	317
0.4-0.5	116
0.5-0.6	25
0.6-0.7	13
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.7125	Intermediate Similarity	NPC486664
0.6977	Remote Similarity	NPC56685
0.6854	Remote Similarity	NPC262166
0.6854	Remote Similarity	NPC241794
0.6629	Remote Similarity	NPC136797
0.6556	Remote Similarity	NPC489825
0.6556	Remote Similarity	NPC489826
0.6421	Remote Similarity	NPC489828
0.6395	Remote Similarity	NPC489829
0.6353	Remote Similarity	NPC255447
0.6277	Remote Similarity	NPC302597
0.6196	Remote Similarity	NPC261934
0.6186	Remote Similarity	NPC275110
0.6154	Remote Similarity	NPC130309
0.593	Remote Similarity	NPC224315
0.5909	Remote Similarity	NPC202198
0.5909	Remote Similarity	NPC489557
0.587	Remote Similarity	NPC5194
0.5825	Remote Similarity	NPC489823
0.5814	Remote Similarity	NPC242482
0.5789	Remote Similarity	NPC242159
0.5684	Remote Similarity	NPC101679
0.5667	Remote Similarity	NPC202521
0.5652	Remote Similarity	NPC6975
0.5644	Remote Similarity	NPC328649
0.5568	Remote Similarity	NPC489593
0.5506	Remote Similarity	NPC485876
0.5495	Remote Similarity	NPC485094
0.5444	Remote Similarity	NPC489591
0.5263	Remote Similarity	NPC285926
0.5263	Remote Similarity	NPC14672
0.5217	Remote Similarity	NPC479068
0.5172	Remote Similarity	NPC487674
0.5158	Remote Similarity	NPC489556
0.5102	Remote Similarity	NPC479070
0.5093	Remote Similarity	NPC296968
0.5089	Remote Similarity	NPC473003
0.5057	Remote Similarity	NPC200589
0.5053	Remote Similarity	NPC479072

Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

● The left chart: Distribution of similarity level between NPC141957 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	2734
0.1-0.2	5955
0.2-0.3	410
0.3-0.4	44
0.4-0.5	6
0.5-0.6	1
0.6-0.7	0
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.587	Remote Similarity	NPD7118	Phase 2

Bioactivity similarity

Similar Natural Products in NPASS

Similarity level is defined by Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.
Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data