NPASS Compound

Natural Product: NPC476227

Natural Product ID	NPC476227
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Micropeptin 88 N
IUPAC Name	(2R,3S)-2-[3-[[(2S,5S,8S,11R,12S,15S,18S,21R)-5-benzyl-8-[(2S)-butan-2-yl]-21-hydroxy-15-[(4-hydroxyphenyl)methyl]-4,11-dimethyl-3,6,9,13,16,22-hexaoxo-2-propan-2-yl-10-oxa-1,4,7,14,17-pentazabicyclo[16.3.1]docosan-12-yl]amino]-3-oxopropyl]-3-(butanoylamino)-5-methylhexanoic acid
Synonyms	Micropeptin 88 N
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL556534
PubChem CID	45269584
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0001813] Peptidomimetics [CHEMONTID:0001961] Depsipeptides [CHEMONTID:0001994] Cyclic depsipeptides

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 150153 0 0 0 0 0 0 0 0999 V2000 8.0767 -4.3981 2.4366 C 0 0 0 0 0 0 0 0 0 0 0 0 8.3427 -3.5046 1.2325 C 0 0 0 0 0 0 0 0 0 0 0 0 8.4079 -2.0411 1.6457 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6666 -1.1910 0.4820 C 0 0 0 0 0 0 0 0 0 0 0 0 7.9476 -0.2575 0.0183 N 0 0 0 0 0 0 0 0 0 0 0 0 6.6852 0.2171 0.5109 C 0 0 2 0 0 0 0 0 0 0 0 0 5.5821 -0.4461 -0.2652 C 0 0 2 0 0 0 0 0 0 0 0 0 5.7109 -0.1382 -1.6962 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9487 -1.0969 -2.5157 O 0 0 0 0 0 0 0 0 0 0 0 0 5.5998 1.1024 -2.2813 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2161 0.0012 0.2420 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1536 -0.7359 -0.5814 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8259 -0.2759 -0.0961 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8626 0.1171 -0.8218 N 0 0 0 0 0 0 0 0 0 0 0 0 0.9311 0.1702 -2.2971 C 0 0 2 0 0 0 0 0 0 0 0 0 1.3324 1.4893 -2.7990 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0060 2.5571 -2.2929 N 0 0 0 0 0 0 0 0 0 0 0 0 0.2551 3.0716 -1.2258 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9703 4.2507 -0.5430 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1997 5.3655 -1.4833 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3409 5.4662 -2.2449 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5485 6.5106 -3.1244 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6003 7.5048 -3.2695 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4501 7.4066 -2.5045 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2501 6.3670 -1.6331 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7820 8.5767 -4.1544 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1231 3.4454 -1.5847 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1310 3.2114 -0.9192 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.4275 2.5785 0.3148 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.0849 3.6336 1.4007 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2715 3.9039 2.2941 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8822 2.6300 2.7692 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.4705 1.8582 1.6517 N 0 0 0 0 0 0 0 0 0 0 0 0 -3.8564 2.2985 0.4718 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6442 2.4311 -0.4223 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.4740 0.9206 1.8803 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.2342 -0.4946 1.5316 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3129 -0.9401 0.4035 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.8811 -1.5231 2.4283 N 0 0 0 0 0 0 0 0 0 0 0 0 -4.7233 -2.9100 2.1516 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.7659 -3.2876 1.1233 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2548 -2.5211 0.2598 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.3106 -2.8569 -0.7651 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.8670 -1.5406 -1.3591 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4186 -0.4582 -1.0322 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8349 -1.4636 -2.2840 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4869 -0.1748 -2.7756 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.4861 -0.2147 -4.2657 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0074 -3.6872 -1.8187 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.0357 -4.0757 -2.9302 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8919 -4.8807 -2.3646 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1200 -2.8636 -2.4242 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3622 -4.6390 1.0734 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.1067 -3.5432 1.8898 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0098 -4.9900 1.6055 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8716 -5.4402 0.3128 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7788 -6.7715 -0.0148 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8219 -7.7303 0.9721 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9591 -7.3114 2.2757 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0519 -5.9650 2.5920 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6417 -1.0337 3.7453 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8929 1.2974 1.5263 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.3945 2.4983 2.2696 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.2590 1.2739 0.0888 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7799 2.7836 3.7945 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2785 4.1369 -2.8034 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1539 1.5591 -3.9580 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6219 -0.2792 1.2798 O 0 0 0 0 0 0 0 0 0 0 0 0 6.5632 1.7005 0.4391 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6383 2.3960 1.2741 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5246 1.9878 2.7327 C 0 0 0 0 0 0 0 0 0 0 0 0 9.0185 2.1996 0.7327 C 0 0 0 0 0 0 0 0 0 0 0 0 9.8701 -1.4384 -0.2139 O 0 0 0 0 0 0 0 0 0 0 0 0 8.6252 -5.3774 2.3328 H 0 0 0 0 0 0 0 0 0 0 0 0 8.4199 -3.9254 3.3843 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0018 -4.6681 2.5231 H 0 0 0 0 0 0 0 0 0 0 0 0 9.2789 -3.8262 0.7437 H 0 0 0 0 0 0 0 0 0 0 0 0 7.4688 -3.6089 0.5496 H 0 0 0 0 0 0 0 0 0 0 0 0 7.5501 -1.7631 2.2542 H 0 0 0 0 0 0 0 0 0 0 0 0 9.3085 -1.9628 2.3187 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5257 -0.1438 1.5800 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7081 -1.5472 -0.1128 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9996 1.3651 -3.1792 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0812 -0.1471 1.3104 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0894 1.0621 -0.0187 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3283 -0.4888 -1.6601 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2285 -1.8208 -0.4538 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5508 -0.6709 -2.6061 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1694 2.3118 -0.4223 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9585 3.8830 -0.1340 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4223 4.6227 0.3319 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1255 4.7080 -2.1712 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4547 6.5864 -3.7250 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3005 8.1792 -2.6080 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6400 6.2856 -1.0355 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1481 8.6335 -4.9595 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7646 1.7005 0.4733 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8468 4.6162 0.9271 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2571 3.2831 2.0150 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9761 4.6281 1.8555 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8714 4.4107 3.2189 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0441 1.9963 3.1394 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5714 0.8625 3.0328 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4174 -3.4118 3.1261 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4348 -3.4113 -0.4169 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1146 0.6347 -2.4124 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5387 -0.1581 -4.6762 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0112 0.7324 -4.6396 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0347 -1.1067 -4.6800 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3414 -4.6224 -1.3485 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7294 -3.2298 -3.5472 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5956 -4.7722 -3.5954 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0815 -4.3269 -2.3966 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7023 -5.8151 -2.9306 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0566 -5.1953 -1.3151 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0578 -2.9395 -3.5442 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9232 -1.7756 -2.2211 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1170 -3.0829 -2.0449 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4245 -4.9254 0.8070 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6250 -3.0226 1.0607 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7411 -3.3937 2.7926 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8346 -4.7289 -0.4792 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6687 -7.1066 -1.0387 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7477 -8.8028 0.7266 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9903 -8.1018 3.0259 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1593 -5.6545 3.6197 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9533 -0.1343 3.6839 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5343 -0.8421 4.3425 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0188 -1.7582 4.3342 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4952 0.4474 1.9903 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.4420 2.6671 1.9398 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4457 2.2963 3.3614 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8509 3.4164 2.1134 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6544 0.6254 -0.5676 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3743 2.3125 -0.3472 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.3106 0.8683 -0.0800 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7532 2.0463 4.4470 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1810 4.4187 -3.1584 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8290 2.3047 -4.0660 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6989 -0.0511 1.6527 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6083 2.0555 0.8464 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7769 2.0253 -0.6032 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3988 3.4784 1.2351 H 0 0 0 0 0 0 0 0 0 0 0 0 7.6361 2.8418 3.4270 H 0 0 0 0 0 0 0 0 0 0 0 0 8.3695 1.2913 2.9518 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5294 1.5212 2.9454 H 0 0 0 0 0 0 0 0 0 0 0 0 9.0502 1.9176 -0.3356 H 0 0 0 0 0 0 0 0 0 0 0 0 9.6497 3.1314 0.8056 H 0 0 0 0 0 0 0 0 0 0 0 0 9.5467 1.4616 1.3831 H 0 0 0 0 0 0 0 0 0 0 0 0 9.9855 -1.1077 -1.1654 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 3 4 1 0 4 5 2 3 5 6 1 0 6 7 1 0 7 8 1 0 8 9 2 0 8 10 1 0 7 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 2 3 17 18 1 0 18 19 1 0 19 20 1 0 20 21 2 0 21 22 1 0 22 23 2 0 23 24 1 0 24 25 2 0 23 26 1 0 18 27 1 0 27 28 2 3 28 29 1 0 29 30 1 0 30 31 1 0 31 32 1 0 32 33 1 0 33 34 1 0 34 35 2 0 33 36 1 0 36 37 1 0 37 38 2 0 37 39 1 0 39 40 1 0 40 41 1 0 41 42 2 3 42 43 1 0 43 44 1 0 44 45 2 0 44 46 1 0 46 47 1 0 47 48 1 0 43 49 1 0 49 50 1 0 50 51 1 0 49 52 1 0 41 53 1 0 40 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 39 61 1 0 36 62 1 0 62 63 1 0 62 64 1 0 32 65 1 0 27 66 1 0 16 67 1 0 13 68 1 0 6 69 1 0 69 70 1 0 70 71 1 0 70 72 1 0 4 73 1 0 47 15 1 0 60 55 1 0 25 20 1 0 34 29 1 0 1 74 1 0 1 75 1 0 1 76 1 0 2 77 1 0 2 78 1 0 3 79 1 0 3 80 1 0 6 81 1 1 7 82 1 6 10 83 1 0 11 84 1 0 11 85 1 0 12 86 1 0 12 87 1 0 15 88 1 6 18 89 1 1 19 90 1 0 19 91 1 0 21 92 1 0 22 93 1 0 24 94 1 0 25 95 1 0 26 96 1 0 29 97 1 1 30 98 1 0 30 99 1 0 31100 1 0 31101 1 0 32102 1 1 36103 1 1 40104 1 1 43105 1 1 47106 1 6 48107 1 0 48108 1 0 48109 1 0 49110 1 1 50111 1 0 50112 1 0 51113 1 0 51114 1 0 51115 1 0 52116 1 0 52117 1 0 52118 1 0 53119 1 0 54120 1 0 54121 1 0 56122 1 0 57123 1 0 58124 1 0 59125 1 0 60126 1 0 61127 1 0 61128 1 0 61129 1 0 62130 1 0 63131 1 0 63132 1 0 63133 1 0 64134 1 0 64135 1 0 64136 1 0 65137 1 0 66138 1 0 67139 1 0 68140 1 0 69141 1 0 69142 1 0 70143 1 0 71144 1 0 71145 1 0 71146 1 0 72147 1 0 72148 1 0 72149 1 0 73150 1 0 M END

Standard InCHIKey	NAWKUZLOHRHOJE-UYNUVXRESA-N
Standard InCHI	InChI=1S/C53H77N7O13/c1-10-15-41(62)54-38(26-29(3)4)36(52(70)71)22-24-42(63)57-45-32(8)73-53(72)44(31(7)11-2)58-48(66)40(28-33-16-13-12-14-17-33)59(9)51(69)46(30(5)6)60-43(64)25-23-37(50(60)68)55-47(65)39(56-49(45)67)27-34-18-20-35(61)21-19-34/h12-14,16-21,29-32,36-40,43-46,61,64H,10-11,15,22-28H2,1-9H3,(H,54,62)(H,55,65)(H,56,67)(H,57,63)(H,58,66)(H,70,71)/t31-,32+,36+,37-,38-,39-,40-,43+,44-,45-,46-/m0/s1
SMILES	CCCC(=N[C@H]([C@H](C(=O)O)CCC(=N[C@@H]1C(=N[C@@H](Cc2ccc(cc2)O)C(=N[C@H]2CC[C@H](N(C2=O)[C@H](C(=O)N([C@H](C(=N[C@H](C(=O)O[C@@H]1C)[C@H](CC)C)O)Cc1ccccc1)C)C(C)C)O)O)O)O)CC(C)C)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	1019.56	Volume:	1042.721 ? Van der Waals volume.
Dense:	0.978	LogP:	3.423 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.641 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.469 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	18.0	Rigid Bonds:	41.0
TPSA:	307.63 ? Topological Polar Surface Area.	H-Bond Acceptor:	20.0
H-Bond Donor:	8.0	Rings:	4.0
Heavy Atoms:	20.0

MedChem Properties

QED Drug-Likeness Score:	0.043	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	7.626	Fsp³:	0.604
MCE-18:	126.176 ? 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:	1
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.77	Fluc inhibitor:	0.003 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.046 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.737 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.005	Promiscuous compounds:	0.008

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.37	MDCK Permeability:	-5.041
Pgp-inhibitor:	0.139	Pgp-substrate:	0.991
PAMPA:	0.998 ? 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):	0.426
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:	0.675
Plasma Protein Binding (PPB):	81.226%	Volume Distribution (VD):	-0.581
Fu:	17.286% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.001
BSEP inhibitor:	1.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.006	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	1.0	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.0
HLM stability:	0.157 ? 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):

0.453

Half-life (T1/2):

2.616

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:	0.164	Rat Oral Acute Toxicity:	0.129
Maximum Recommended Daily Dose:	0.015	Skin Sensitization:	1.0
Carcinogencity:	0.232	Eye Corrosion:	0.0
Eye Irritation:	0.003	Respiratory Toxicity:	0.006
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	0.998
Hematotoxicity:	0.964	Drug-induced Nephrotoxicity:	1.0
Genotoxicity:	1.0	RPMI-8226 Immunitoxicity:	0.0
A549 Cytotoxicity:	0.0	Hek293 Cytotoxicity:	0.001
BCF:	0.333 ? 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:	3.322 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.158 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.065 ? 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
NPO33392	cyanobacterium microcystis aeruginosa nies-88	Species	Cyanobacteriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[15679310]

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
IC50	2

Activity Type	# Activity
Others	2

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
NPT2	Others	Unspecified	n.a.	IC50	=	15000.0	nM	DOI[10.1016/j.indcrop.2012.05.026]
NPT2	Others	Unspecified	n.a.	IC50	>	100000.0	nM	DOI[10.1016/j.indcrop.2012.05.026]

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 NPC476227 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	11770
0.1-0.2	36055
0.2-0.3	1775
0.3-0.4	185
0.4-0.5	40
0.5-0.6	23
0.6-0.7	8
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
0.7807	Intermediate Similarity	NPC230611
0.686	Remote Similarity	NPC40234
0.6721	Remote Similarity	NPC159767
0.6667	Remote Similarity	NPC155506
0.6423	Remote Similarity	NPC107938
0.6393	Remote Similarity	NPC45037
0.6371	Remote Similarity	NPC294516
0.6107	Remote Similarity	NPC240130
0.608	Remote Similarity	NPC471526
0.5739	Remote Similarity	NPC163392
0.5714	Remote Similarity	NPC279871
0.5682	Remote Similarity	NPC61332
0.5659	Remote Similarity	NPC473407
0.5645	Remote Similarity	NPC273755
0.5625	Remote Similarity	NPC194671
0.561	Remote Similarity	NPC306804
0.5591	Remote Similarity	NPC489102
0.5556	Remote Similarity	NPC50016
0.5546	Remote Similarity	NPC239762
0.5469	Remote Similarity	NPC5719
0.5455	Remote Similarity	NPC60516
0.542	Remote Similarity	NPC269750
0.5414	Remote Similarity	NPC46009
0.5308	Remote Similarity	NPC22883
0.5255	Remote Similarity	NPC473404
0.5238	Remote Similarity	NPC62104
0.5231	Remote Similarity	NPC137627
0.5227	Remote Similarity	NPC63040
0.5224	Remote Similarity	NPC302715
0.5182	Remote Similarity	NPC471592
0.5038	Remote Similarity	NPC471053
0.5038	Remote Similarity	NPC471051

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC476227 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	2794
0.1-0.2	5998
0.2-0.3	349
0.3-0.4	9
0.4-0.5	0
0.5-0.6	0
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
		NPD

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