NPASS Compound

Natural Product: NPC163961

Natural Product ID	NPC163961
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Lyngbyastatin 4
IUPAC Name	[(2R)-3-[[(2S)-1-[[(2S)-1-[[(2S,5S,8S,11R,12S,15Z,18S,21R)-2-benzyl-15-ethylidene-21-hydroxy-5-[(4-hydroxyphenyl)methyl]-4,11-dimethyl-3,6,9,13,16,22-hexaoxo-8-propan-2-yl-10-oxa-1,4,7,14,17-pentazabicyclo[16.3.1]docosan-12-yl]amino]-4-(4-hydroxyphenyl)-1-oxobutan-2-yl]amino]-1-oxopropan-2-yl]amino]-2-hydroxy-3-oxopropyl] hydrogen sulfate
Synonyms	Lyngbyastatin 4
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL252952
PubChem CID	16104920
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 148152 0 0 0 0 0 0 0 0999 V2000 1.4425 -4.2275 -2.7832 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0274 -4.3440 -2.3507 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3645 -3.5298 -1.3511 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7597 -3.6572 -0.9356 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2654 -2.9547 0.0226 N 0 0 0 0 0 0 0 0 0 0 0 0 -3.6038 -3.0334 0.4722 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.7849 -4.0300 1.6183 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7344 -3.5242 2.6542 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9595 -2.8152 2.0925 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.6038 -1.7457 1.2258 N 0 0 0 0 0 0 0 0 0 0 0 0 -6.5528 -0.7368 0.7207 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.8445 -0.8484 1.4447 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.9384 0.0554 1.0537 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.8132 -0.2868 0.0105 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.8773 0.4640 -0.3731 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.1332 1.6453 0.2929 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.3070 2.0459 1.3360 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.2221 1.2335 1.6914 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8927 0.5700 0.7552 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3794 1.0129 1.7515 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.7785 1.4400 -0.3442 N 0 0 0 0 0 0 0 0 0 0 0 0 -6.4874 1.0242 -1.4969 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0204 2.6421 -0.3448 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.3657 3.8144 0.4538 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6621 4.4703 0.1435 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6257 5.3283 -0.9761 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7573 6.0219 -1.3163 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.9394 5.9314 -0.6258 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.9393 5.0735 0.4760 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.8119 4.3518 0.8550 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.0635 6.6503 -1.0050 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5221 2.3154 -0.3379 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1002 1.4052 -1.0116 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.0952 0.6196 -1.4743 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.1118 0.4460 -3.0163 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9759 1.7795 -3.6904 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3155 -0.3272 -3.4454 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6939 0.8916 -1.1290 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3011 1.9684 -0.6599 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2162 -0.1148 -1.3410 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5686 -0.1063 -1.0981 C 0 0 2 0 0 0 0 0 0 0 0 0 2.3318 -0.2383 -2.3824 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0275 -1.0388 0.0005 C 0 0 1 0 0 0 0 0 0 0 0 0 1.4182 -2.3915 -0.0584 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5199 -2.6561 -0.8335 N 0 0 0 0 0 0 0 0 0 0 0 0 1.9247 -3.3382 0.8166 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4227 -0.9437 0.0941 N 0 0 0 0 0 0 0 0 0 0 0 0 4.4181 -1.5650 -0.2704 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8104 -1.0364 0.0883 C 0 0 2 0 0 0 0 0 0 0 0 0 5.6937 -0.1118 1.2766 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1619 -0.8702 2.4587 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1175 -1.9597 2.8148 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1473 -1.6016 3.6931 C 0 0 0 0 0 0 0 0 0 0 0 0 8.0729 -2.5386 4.0841 C 0 0 0 0 0 0 0 0 0 0 0 0 7.9905 -3.8290 3.6170 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9730 -4.1612 2.7584 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0445 -3.2391 2.3595 C 0 0 0 0 0 0 0 0 0 0 0 0 8.9582 -4.7499 4.0458 O 0 0 0 0 0 0 0 0 0 0 0 0 6.3967 -0.4378 -1.0378 N 0 0 0 0 0 0 0 0 0 0 0 0 7.4351 -0.2439 -1.6185 C 0 0 0 0 0 0 0 0 0 0 0 0 8.8544 -0.6269 -1.3554 C 0 0 2 0 0 0 0 0 0 0 0 0 8.9475 -1.4973 -0.0998 C 0 0 0 0 0 0 0 0 0 0 0 0 9.7411 0.3951 -1.3341 N 0 0 0 0 0 0 0 0 0 0 0 0 10.4003 1.3564 -1.4971 C 0 0 0 0 0 0 0 0 0 0 0 0 11.5619 1.7429 -0.6252 C 0 0 1 0 0 0 0 0 0 0 0 0 11.2495 3.0828 0.0569 C 0 0 0 0 0 0 0 0 0 0 0 0 10.9537 4.0630 -0.8886 O 0 0 0 0 0 0 0 0 0 0 0 0 10.2916 5.3779 -0.0710 S 0 0 0 0 0 0 0 0 0 0 0 0 9.1743 5.8993 -0.9085 O 0 0 0 0 0 0 0 0 0 0 0 0 11.3414 6.4120 0.1874 O 0 0 0 0 0 0 0 0 0 0 0 0 9.6508 4.8722 1.4026 O 0 0 0 0 0 0 0 0 0 0 0 0 11.8322 0.8288 0.3606 O 0 0 0 0 0 0 0 0 0 0 0 0 10.1609 2.2651 -2.5506 O 0 0 0 0 0 0 0 0 0 0 0 0 7.3306 0.5229 -2.8418 O 0 0 0 0 0 0 0 0 0 0 0 0 4.4181 -2.7431 -1.0107 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6998 3.0988 0.4586 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2303 -1.7957 0.9446 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6494 -0.7687 1.1297 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.8071 -2.5345 3.1394 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5532 -4.5538 -1.5884 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1419 -4.5549 -1.9812 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5863 -5.0249 -3.5787 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6992 -3.2792 -3.2634 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6610 -5.0527 -2.8175 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2211 -3.4930 -0.3629 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7850 -4.1184 2.1325 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0329 -5.0098 1.1903 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2484 -2.9221 3.4479 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1424 -4.4231 3.2029 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4661 -3.5878 1.4494 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6729 -0.9784 -0.3808 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.6131 -0.5556 2.5199 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.2076 -1.9037 1.5173 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.6130 -1.2092 -0.5089 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.5399 0.1562 -1.2027 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.9915 2.2231 -0.0407 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.5131 2.9598 1.8646 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.5928 1.5699 2.5041 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4785 0.5936 -1.3466 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5681 1.8786 -2.2341 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8159 0.2836 -2.0341 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1383 3.0646 -1.4517 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4125 3.6106 1.5661 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5688 4.6228 0.3736 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7039 5.4271 -1.5510 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.7271 6.6869 -2.1898 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.8599 5.0195 1.0099 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.8307 3.7021 1.7172 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.9735 6.5256 -0.5876 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2772 -0.4584 -1.1377 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2114 -0.1507 -3.2427 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0013 2.1650 -3.8568 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5174 2.5125 -2.9577 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4069 1.7319 -4.6304 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7771 -0.8650 -2.5958 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0839 0.3983 -3.8055 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0832 -1.0529 -4.2591 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8180 0.9285 -0.7009 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7445 -0.8931 -3.0834 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3688 -0.5452 -2.2530 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2816 0.7739 -2.8900 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6109 -0.5623 0.9518 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9073 -4.3324 0.6290 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4019 -1.9099 0.3863 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0753 0.7838 1.0433 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7066 0.2954 1.4962 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2101 -1.3642 2.2035 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0403 -0.1787 3.3249 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2031 -0.5998 4.0498 H 0 0 0 0 0 0 0 0 0 0 0 0 8.8842 -2.2576 4.7742 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9463 -5.1966 2.4129 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2616 -3.5340 1.6917 H 0 0 0 0 0 0 0 0 0 0 0 0 8.7101 -5.6611 4.3520 H 0 0 0 0 0 0 0 0 0 0 0 0 9.1524 -1.3672 -2.1845 H 0 0 0 0 0 0 0 0 0 0 0 0 8.5687 -1.0184 0.7978 H 0 0 0 0 0 0 0 0 0 0 0 0 8.5468 -2.4984 -0.3228 H 0 0 0 0 0 0 0 0 0 0 0 0 10.0460 -1.6857 0.1094 H 0 0 0 0 0 0 0 0 0 0 0 0 12.4573 1.9140 -1.2507 H 0 0 0 0 0 0 0 0 0 0 0 0 12.0971 3.3754 0.6751 H 0 0 0 0 0 0 0 0 0 0 0 0 10.3237 2.9275 0.6676 H 0 0 0 0 0 0 0 0 0 0 0 0 9.8891 5.5147 2.1185 H 0 0 0 0 0 0 0 0 0 0 0 0 12.0070 -0.0772 0.0585 H 0 0 0 0 0 0 0 0 0 0 0 0 9.5426 2.0545 -3.3189 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4264 0.7605 -3.2129 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7672 -2.8535 -1.8045 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0888 2.6671 1.1750 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5644 -2.9683 3.9895 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5172 -4.3490 -1.8937 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 2 0 3 4 1 0 4 5 2 0 5 6 1 0 6 7 1 0 7 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 0 14 15 1 0 15 16 2 0 16 17 1 0 17 18 2 0 11 19 1 0 19 20 2 0 19 21 1 0 21 22 1 0 21 23 1 0 23 24 1 0 24 25 1 0 25 26 2 0 26 27 1 0 27 28 2 0 28 29 1 0 29 30 2 0 28 31 1 0 23 32 1 0 32 33 2 3 33 34 1 0 34 35 1 0 35 36 1 0 35 37 1 0 34 38 1 0 38 39 2 0 38 40 1 0 40 41 1 0 41 42 1 0 41 43 1 0 43 44 1 0 44 45 2 0 44 46 1 0 43 47 1 0 47 48 2 3 48 49 1 0 49 50 1 0 50 51 1 0 51 52 1 0 52 53 2 0 53 54 1 0 54 55 2 0 55 56 1 0 56 57 2 0 55 58 1 0 49 59 1 0 59 60 2 3 60 61 1 0 61 62 1 0 61 63 1 0 63 64 2 3 64 65 1 0 65 66 1 0 66 67 1 0 67 68 1 0 68 69 2 0 68 70 2 0 68 71 1 0 65 72 1 0 64 73 1 0 60 74 1 0 48 75 1 0 32 76 1 0 10 77 1 0 77 78 2 0 9 79 1 0 4 80 1 0 45 3 1 0 57 52 1 0 77 6 1 0 18 13 1 0 30 25 1 0 1 81 1 0 1 82 1 0 1 83 1 0 2 84 1 0 6 85 1 6 7 86 1 0 7 87 1 0 8 88 1 0 8 89 1 0 9 90 1 6 11 91 1 6 12 92 1 0 12 93 1 0 14 94 1 0 15 95 1 0 16 96 1 0 17 97 1 0 18 98 1 0 22 99 1 0 22100 1 0 22101 1 0 23102 1 6 24103 1 0 24104 1 0 26105 1 0 27106 1 0 29107 1 0 30108 1 0 31109 1 0 34110 1 1 35111 1 0 36112 1 0 36113 1 0 36114 1 0 37115 1 0 37116 1 0 37117 1 0 41118 1 1 42119 1 0 42120 1 0 42121 1 0 43122 1 1 46123 1 0 49124 1 1 50125 1 0 50126 1 0 51127 1 0 51128 1 0 53129 1 0 54130 1 0 56131 1 0 57132 1 0 58133 1 0 61134 1 6 62135 1 0 62136 1 0 62137 1 0 65138 1 6 66139 1 0 66140 1 0 71141 1 0 72142 1 0 73143 1 0 74144 1 0 75145 1 0 76146 1 0 79147 1 0 80148 1 0 M END

Standard InCHIKey	QVBXBGIPSMEBEL-RNXFLSOQSA-N
Standard InCHI	InChI=1S/C53H68N8O18S/c1-7-36-46(67)57-38-23-24-42(65)61(51(38)72)40(26-32-11-9-8-10-12-32)52(73)60(6)39(25-33-15-20-35(63)21-16-33)48(69)58-43(28(2)3)53(74)79-30(5)44(50(71)55-36)59-47(68)37(22-17-31-13-18-34(62)19-14-31)56-45(66)29(4)54-49(70)41(64)27-78-80(75,76)77/h7-16,18-21,28-30,37-44,62-65H,17,22-27H2,1-6H3,(H,54,70)(H,55,71)(H,56,66)(H,57,67)(H,58,69)(H,59,68)(H,75,76,77)/b36-7-/t29-,30+,37-,38-,39-,40-,41+,42+,43-,44-/m0/s1
SMILES	C/C=C1/C(=N[C@H]2CC[C@H](N([C@@H](Cc3ccccc3)C(=O)N(C)[C@@H](Cc3ccc(cc3)O)C(=N[C@@H](C(C)C)C(=O)O[C@H](C)[C@@H](C(=N1)O)N=C([C@H](CCc1ccc(cc1)O)N=C([C@H](C)N=C([C@@H](COS(=O)(=O)O)O)O)O)O)O)C2=O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	1136.44	Volume:	1097.076 ? Van der Waals volume.
Dense:	1.036	LogP:	-0.292 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.287 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.12 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	17.0	Rigid Bonds:	50.0
TPSA:	406.98 ? Topological Polar Surface Area.	H-Bond Acceptor:	26.0
H-Bond Donor:	11.0	Rings:	5.0
Heavy Atoms:	27.0

MedChem Properties

QED Drug-Likeness Score:	0.039	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	7.862	Fsp³:	0.453
MCE-18:	148.753 ? 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:	0.38	Fluc inhibitor:	0.183 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.022 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.941 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.006	Promiscuous compounds:	0.018

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.719	MDCK Permeability:	-4.989
Pgp-inhibitor:	0.039	Pgp-substrate:	1.0
PAMPA:	0.981 ? 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):	0.091
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:	0.788
Plasma Protein Binding (PPB):	59.357%	Volume Distribution (VD):	-0.522
Fu:	35.27% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.001
BSEP inhibitor:	0.995

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.001	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.003	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.0
HLM stability:	0.005 ? 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):

-0.13

Half-life (T1/2):

3.076

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:	0.084	Rat Oral Acute Toxicity:	0.613
Maximum Recommended Daily Dose:	1.0	Skin Sensitization:	1.0
Carcinogencity:	0.672	Eye Corrosion:	0.0
Eye Irritation:	0.0	Respiratory Toxicity:	0.997
Drug-induced Neurotoxicity:	0.013	Ototoxicity:	1.0
Hematotoxicity:	0.007	Drug-induced Nephrotoxicity:	1.0
Genotoxicity:	1.0	RPMI-8226 Immunitoxicity:	0.0
A549 Cytotoxicity:	0.0	Hek293 Cytotoxicity:	0.078
BCF:	0.403 ? 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:	3.274 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.071 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.203 ? 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
NPO23339	Lyngbya confervoides	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[11809060]
NPO23339	Lyngbya confervoides	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[17253864]
NPO23339	Lyngbya confervoides	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[18220404]
NPO23339	Lyngbya confervoides	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO23339	Lyngbya confervoides	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]

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	9
Activity	1

Activity Type	# Activity
Individual protein	1
Others	9

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT279	Individual protein	Leukocyte elastase	Homo sapiens	IC50	=	49.0	nM	PMID[18710917]

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified	n.a.	IC50	=	30.0	nM	PMID[18955526]
NPT2	Others	Unspecified	n.a.	IC50	=	300.0	nM	PMID[23819826]
NPT2	Others	Unspecified	n.a.	IC50	=	13.9	nM	PMID[16417306]
NPT2	Others	Unspecified	n.a.	IC50	=	4300.0	nM	PMID[22783984]
NPT2	Others	Unspecified	n.a.	Activity	=	72.2	%	Open TG-GATES in vivo data: Hematology
NPT2	Others	Unspecified	n.a.	IC50	>	10000.0	nM	PMID[22705001]
NPT2	Others	Unspecified	n.a.	IC50	=	614.0	nM	Open TG-GATES in vivo data: Hematology
NPT2	Others	Unspecified	n.a.	IC50	=	41.0	nM	PMID[11000021]

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 NPC163961 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	11407
0.1-0.2	36563
0.2-0.3	1734
0.3-0.4	91
0.4-0.5	21
0.5-0.6	25
0.6-0.7	8
0.7-0.8	0
0.8-0.85	1
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8818	High Similarity	NPC294951
0.8264	Intermediate Similarity	NPC473305
0.735	Intermediate Similarity	NPC279871
0.7273	Intermediate Similarity	NPC302715
0.7227	Intermediate Similarity	NPC194671
0.7107	Intermediate Similarity	NPC269750
0.696	Remote Similarity	NPC488263
0.6748	Remote Similarity	NPC471050
0.6555	Remote Similarity	NPC306804
0.648	Remote Similarity	NPC471526
0.6406	Remote Similarity	NPC102959
0.6328	Remote Similarity	NPC471048
0.616	Remote Similarity	NPC471052
0.6111	Remote Similarity	NPC137627
0.5954	Remote Similarity	NPC159767
0.5952	Remote Similarity	NPC50016
0.594	Remote Similarity	NPC61332
0.5923	Remote Similarity	NPC473407
0.5909	Remote Similarity	NPC155506
0.5891	Remote Similarity	NPC471053
0.5859	Remote Similarity	NPC489102
0.5769	Remote Similarity	NPC471051
0.5766	Remote Similarity	NPC240130
0.5692	Remote Similarity	NPC22883
0.5597	Remote Similarity	NPC487289
0.553	Remote Similarity	NPC45037
0.5481	Remote Similarity	NPC60516
0.5401	Remote Similarity	NPC65714
0.5401	Remote Similarity	NPC473371
0.5259	Remote Similarity	NPC63040
0.5246	Remote Similarity	NPC163392
0.5227	Remote Similarity	NPC248670
0.52	Remote Similarity	NPC239762
0.5145	Remote Similarity	NPC40234
0.5076	Remote Similarity	NPC273755
0.5074	Remote Similarity	NPC217804
0.507	Remote Similarity	NPC220060
0.507	Remote Similarity	NPC473404
0.5037	Remote Similarity	NPC5719

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC163961 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	6063
0.2-0.3	291
0.3-0.4	2
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