NPASS Compound

Natural Product: NPC471051

Natural Product ID	NPC471051
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Symplostatin 7
IUPAC Name	sodium;[(2R)-3-[[(2S,3S)-1-[[(2S,5S,8S,11R,12S,15Z,18S,21R)-2,5-dibenzyl-8-[(2R)-butan-2-yl]-15-ethylidene-21-hydroxy-4,11-dimethyl-3,6,9,13,16,22-hexaoxo-10-oxa-1,4,7,14,17-pentazabicyclo[16.3.1]docosan-12-yl]amino]-3-methyl-1-oxopentan-2-yl]amino]-2-methoxy-3-oxopropyl] sulfate
Synonyms	symplostatin 7
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL2338552
PubChem CID	71717727
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 138140 0 0 0 0 0 0 0 0999 V2000 -1.3543 2.0984 3.1510 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5955 0.9540 3.8339 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3684 -0.3402 3.6888 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.5631 -0.6903 2.2096 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.3046 -1.8559 1.9956 N 0 0 0 0 0 0 0 0 0 0 0 0 -3.4974 -2.1231 1.8335 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7589 -3.5234 1.6374 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.5938 -1.1794 1.8270 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.8640 -1.6848 2.5298 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6847 -1.9959 3.9491 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8505 -0.9715 4.8916 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6912 -1.2000 6.2385 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3582 -2.4596 6.7277 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1973 -3.4622 5.8081 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3589 -3.2232 4.4611 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0401 -0.6507 0.5699 N 0 0 0 0 0 0 0 0 0 0 0 0 -5.5706 -1.5281 -0.3998 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0557 0.6955 0.2823 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7538 1.3800 1.2741 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.3631 1.4939 -0.9288 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.7463 1.9837 -0.8064 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.3280 2.8224 -1.8373 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9541 4.1714 -1.8925 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.5112 5.0532 -2.7907 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.4585 4.6397 -3.6696 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.8575 3.3161 -3.6500 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.2853 2.4469 -2.7396 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8668 0.8983 -2.1254 N 0 0 0 0 0 0 0 0 0 0 0 0 -5.4802 0.5526 -3.3229 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.6086 -0.2691 -3.2066 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.6851 -0.0066 -4.4470 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3088 -0.4975 -4.2048 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6434 0.5662 -3.3320 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.4807 0.5949 -2.1277 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0273 0.3500 -1.0320 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2702 0.2912 -3.0873 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.4139 0.6864 -3.9509 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9957 0.4293 -3.7488 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8829 0.8539 -4.6763 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3288 0.6170 -4.5188 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4836 -0.2504 -2.6516 N 0 0 0 0 0 0 0 0 0 0 0 0 1.8740 0.1951 -1.5351 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3593 -0.8020 -0.5500 C 0 0 2 0 0 0 0 0 0 0 0 0 2.0400 -0.4173 0.8557 C 0 0 2 0 0 0 0 0 0 0 0 0 0.6730 -0.1140 1.1494 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1176 -0.9885 1.8069 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2892 -2.1338 2.1500 O 0 0 0 0 0 0 0 0 0 0 0 0 2.9917 0.5493 1.4628 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6899 -1.1245 -0.7730 N 0 0 0 0 0 0 0 0 0 0 0 0 4.7388 -0.6628 -1.1311 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9542 -1.5749 -1.1782 C 0 0 2 0 0 0 0 0 0 0 0 0 5.6842 -2.9229 -0.5961 C 0 0 2 0 0 0 0 0 0 0 0 0 5.2670 -2.9506 0.8356 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2455 -2.3782 1.8027 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0174 -3.6866 -0.6653 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0864 -0.9109 -0.7995 N 0 0 0 0 0 0 0 0 0 0 0 0 7.5180 0.0647 -0.1756 C 0 0 0 0 0 0 0 0 0 0 0 0 9.0129 0.2612 -0.1314 C 0 0 1 0 0 0 0 0 0 0 0 0 9.3228 1.5635 -0.8262 C 0 0 0 0 0 0 0 0 0 0 0 0 10.6703 1.8168 -0.7762 O 0 0 0 0 0 0 0 0 0 0 0 0 10.9445 3.1895 -1.7317 S 0 0 0 0 0 0 0 0 0 0 0 0 9.7297 3.5596 -2.5169 O 0 0 0 0 0 0 0 0 0 0 0 0 12.0287 2.7972 -2.7023 O 0 0 0 0 0 0 0 0 0 0 0 0 11.3858 4.5105 -0.7940 O 0 0 0 0 0 0 0 0 0 0 0 0 9.3970 0.3135 1.1845 O 0 0 0 0 0 0 0 0 0 0 0 0 10.3190 -0.6421 1.5590 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6647 0.9408 0.4555 O 0 0 0 0 0 0 0 0 0 0 0 0 4.9918 0.6464 -1.5246 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8275 1.5589 -1.3010 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8125 1.3625 -5.0891 O 0 0 0 0 0 1 0 0 0 0 0 0 -2.5379 -0.4100 4.5665 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 Na 0 0 0 0 0 15 0 0 0 0 0 0 -2.4452 2.0282 3.3527 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1147 2.0958 2.0815 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9971 3.0309 3.6028 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3912 0.9051 3.3606 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4599 1.2511 4.8735 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6271 -1.1245 4.1108 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8664 0.2188 1.6961 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0410 -4.0655 1.1737 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2481 -0.2729 2.4198 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6172 -0.8709 2.3735 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2594 -2.5769 2.0105 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1073 0.0224 4.5634 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8227 -0.3861 6.9712 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2371 -2.6207 7.8054 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9408 -4.4504 6.1437 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2278 -4.0627 3.7872 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7307 -2.5561 0.0354 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8502 -1.6939 -1.2139 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5983 -1.2462 -0.7413 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7166 2.4502 -0.8124 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4645 1.1731 -0.4626 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7443 2.6411 0.1334 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1892 4.5369 -1.1966 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1928 6.0939 -2.8019 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.9359 5.2977 -4.4056 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.6079 2.9426 -4.3315 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.6349 1.4318 -2.7505 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9293 1.5234 -3.7627 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2489 -1.2043 -3.2519 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2317 -0.8748 -4.9559 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6426 0.7334 -5.3256 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7675 -0.5019 -5.1652 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2564 -1.4941 -3.7483 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7137 1.5112 -3.9289 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4868 1.3664 -5.5255 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5065 -0.1140 -3.6988 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9076 1.5170 -4.2837 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7511 0.1814 -5.4708 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7268 -1.7577 -0.7947 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1886 -1.4186 1.4226 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7927 -0.0099 2.0097 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5527 1.1820 0.7303 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4340 1.1914 2.1837 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0225 -1.7774 -2.3116 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9151 -3.4127 -1.2078 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1392 -4.0502 1.0927 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2594 -2.5276 1.0358 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9220 -1.4254 2.2762 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3426 -3.0940 2.6706 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2615 -2.3410 1.3622 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1268 -4.3997 0.1528 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9897 -4.2460 -1.6217 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8843 -2.9805 -0.6722 H 0 0 0 0 0 0 0 0 0 0 0 0 9.5258 -0.5517 -0.6837 H 0 0 0 0 0 0 0 0 0 0 0 0 8.8122 2.3916 -0.2472 H 0 0 0 0 0 0 0 0 0 0 0 0 8.8936 1.6145 -1.8454 H 0 0 0 0 0 0 0 0 0 0 0 0 11.4147 4.2065 0.1554 H 0 0 0 0 0 0 0 0 0 0 0 0 10.5219 -0.4619 2.6547 H 0 0 0 0 0 0 0 0 0 0 0 0 9.9619 -1.6875 1.4009 H 0 0 0 0 0 0 0 0 0 0 0 0 11.2584 -0.5098 1.0104 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8927 0.6023 1.0169 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3556 1.2596 -1.9392 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4362 2.2442 -1.9080 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2974 0.3766 4.4828 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9695 -1.4411 4.4828 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1361 -0.4061 5.6358 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 1 0 5 6 2 3 6 7 1 0 6 8 1 0 8 9 1 0 9 10 1 0 10 11 2 0 11 12 1 0 12 13 2 0 13 14 1 0 14 15 2 0 8 16 1 0 16 17 1 0 16 18 1 0 18 19 2 0 18 20 1 0 20 21 1 0 21 22 1 0 22 23 2 0 23 24 1 0 24 25 2 0 25 26 1 0 26 27 2 0 20 28 1 0 28 29 1 0 29 30 1 0 29 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 2 0 37 38 1 0 38 39 2 0 39 40 1 0 38 41 1 0 41 42 2 0 42 43 1 0 43 44 1 0 44 45 1 0 45 46 1 0 46 47 2 0 44 48 1 0 43 49 1 0 49 50 2 3 50 51 1 0 51 52 1 0 52 53 1 0 53 54 1 0 52 55 1 0 51 56 1 0 56 57 2 3 57 58 1 0 58 59 1 0 59 60 1 0 60 61 1 0 61 62 2 0 61 63 2 0 61 64 1 0 58 65 1 0 65 66 1 0 57 67 1 0 50 68 1 0 42 69 1 0 37 70 1 0 3 71 1 0 46 4 1 0 15 10 1 0 27 22 1 0 34 28 1 0 1 73 1 0 1 74 1 0 1 75 1 0 2 76 1 0 2 77 1 0 3 78 1 1 4 79 1 6 7 80 1 0 8 81 1 1 9 82 1 0 9 83 1 0 11 84 1 0 12 85 1 0 13 86 1 0 14 87 1 0 15 88 1 0 17 89 1 0 17 90 1 0 17 91 1 0 20 92 1 1 21 93 1 0 21 94 1 0 23 95 1 0 24 96 1 0 25 97 1 0 26 98 1 0 27 99 1 0 29100 1 6 30101 1 0 31102 1 0 31103 1 0 32104 1 0 32105 1 0 33106 1 6 39107 1 0 40108 1 0 40109 1 0 40110 1 0 43111 1 6 44112 1 1 48113 1 0 48114 1 0 48115 1 0 51116 1 6 52117 1 6 53118 1 0 53119 1 0 54120 1 0 54121 1 0 54122 1 0 55123 1 0 55124 1 0 55125 1 0 58126 1 6 59127 1 0 59128 1 0 64129 1 0 66130 1 0 66131 1 0 66132 1 0 67133 1 0 68134 1 0 69135 1 0 71136 1 0 71137 1 0 71138 1 0 M CHG 2 70 -1 72 1 M END

Standard InCHIKey	PQKKBRUUQQKZIM-OFYOIGKZSA-M
Standard InCHI	InChI=1S/C48H67N7O15S.Na/c1-9-27(4)38(51-43(59)36(68-8)26-69-71(65,66)67)44(60)53-40-29(6)70-48(64)39(28(5)10-2)52-42(58)34(24-30-18-14-12-15-19-30)54(7)47(63)35(25-31-20-16-13-17-21-31)55-37(56)23-22-33(46(55)62)50-41(57)32(11-3)49-45(40)61;/h11-21,27-29,33-40,56H,9-10,22-26H2,1-8H3,(H,49,61)(H,50,57)(H,51,59)(H,52,58)(H,53,60)(H,65,66,67);/q;+1/p-1/b32-11-;/t27-,28+,29+,33-,34-,35-,36+,37+,38-,39-,40-;/m0./s1
SMILES	CC[C@H]([C@@H]1N=C(O)[C@H](Cc2ccccc2)N(C)C(=O)[C@H](Cc2ccccc2)N2[C@H](O)CC[C@@H](C2=O)N=C(/C(=C/C)/N=C([C@H]([C@H](OC1=O)C)N=C([C@H]([C@H](CC)C)N=C([C@@H](COS(=O)(=O)O)OC)O)O)O)[O-])C.[Na+]

Calculated Properties

Physi-Chem Properties

Molecular Weight:	1012.43	Volume:	991.013 ? Van der Waals volume.
Dense:	1.022	LogP:	-0.425 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.494 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.001 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	16.0	Rigid Bonds:	43.0
TPSA:	325.76 ? Topological Polar Surface Area.	H-Bond Acceptor:	22.0
H-Bond Donor:	6.0	Rings:	4.0
Heavy Atoms:	23.0

MedChem Properties

QED Drug-Likeness Score:	0.061	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	7.683	Fsp³:	0.542
MCE-18:	126.486 ? 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:	0.629	Fluc inhibitor:	0.07 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.031 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.811 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.023	Promiscuous compounds:	0.013

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.613	MDCK Permeability:	-5.062
Pgp-inhibitor:	0.988	Pgp-substrate:	0.997
PAMPA:	0.331 ? 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):	0.904
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:	0.493
Plasma Protein Binding (PPB):	71.532%	Volume Distribution (VD):	-0.629
Fu:	29.624% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.989	BCRP inhibitor:	0.001
BSEP inhibitor:	0.98

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.004	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.998	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.0
HLM stability:	0.008 ? 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):

0.352

Half-life (T1/2):

2.017

ADMET: Toxicity

hERG Blockers:	0.001	hERG Blockers (10um):	0.0
Human Hepatotoxicity (H-HT):	1.0	Drug-induced Liver Injury (DILI):	1.0
AMES Toxicity:	0.085	Rat Oral Acute Toxicity:	0.341
Maximum Recommended Daily Dose:	0.976	Skin Sensitization:	1.0
Carcinogencity:	0.318	Eye Corrosion:	0.0
Eye Irritation:	0.0	Respiratory Toxicity:	0.938
Drug-induced Neurotoxicity:	0.01	Ototoxicity:	1.0
Hematotoxicity:	0.346	Drug-induced Nephrotoxicity:	1.0
Genotoxicity:	1.0	RPMI-8226 Immunitoxicity:	0.0
A549 Cytotoxicity:	0.0	Hek293 Cytotoxicity:	0.006
BCF:	0.429 ? 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:	3.254 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.893 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.094 ? 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
NPO33098	cyanobacteria	Phylum	n.a.	Bacteria	n.a.	n.a.	n.a.	PMID[19715320]
NPO33098	cyanobacteria	Phylum	n.a.	Bacteria	n.a.	n.a.	n.a.	PMID[23350733]
NPO33098	cyanobacteria	Phylum	n.a.	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]

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	4
Activity	1

Activity Type	# Activity
Individual protein	1
Others	4

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	=	195.0	nM	PMID[23357036]

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified	n.a.	Activity	=	70.7	%	PMID[8691207]
NPT2	Others	Unspecified	n.a.	IC50	>	10000.0	nM	PMID[19161316]
NPT2	Others	Unspecified	n.a.	IC50	=	515.0	nM	PMID[24417634]
NPT2	Others	Unspecified	n.a.	IC50	=	77.0	nM	PMID[18364258]

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 NPC471051 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	11221
0.1-0.2	36842
0.2-0.3	1647
0.3-0.4	91
0.4-0.5	24
0.5-0.6	27
0.6-0.7	2
0.7-0.8	0
0.8-0.85	1
0.85-0.9	0
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.96	High Similarity	NPC471053
0.9109	High Similarity	NPC471052
0.8182	Intermediate Similarity	NPC471048
0.7434	Intermediate Similarity	NPC471050
0.6417	Remote Similarity	NPC471526
0.6016	Remote Similarity	NPC63040
0.584	Remote Similarity	NPC473407
0.5802	Remote Similarity	NPC489837
0.5769	Remote Similarity	NPC163961
0.5736	Remote Similarity	NPC61332
0.56	Remote Similarity	NPC22883
0.5597	Remote Similarity	NPC489838
0.5564	Remote Similarity	NPC489835
0.5564	Remote Similarity	NPC489836
0.552	Remote Similarity	NPC5719
0.5504	Remote Similarity	NPC302715
0.5448	Remote Similarity	NPC240130
0.5433	Remote Similarity	NPC194671
0.541	Remote Similarity	NPC306804
0.5397	Remote Similarity	NPC279871
0.5385	Remote Similarity	NPC60516
0.5349	Remote Similarity	NPC269750
0.5349	Remote Similarity	NPC294951
0.5349	Remote Similarity	NPC15068
0.5308	Remote Similarity	NPC230611
0.5263	Remote Similarity	NPC488263
0.5161	Remote Similarity	NPC62104
0.5152	Remote Similarity	NPC159767
0.5147	Remote Similarity	NPC25539
0.5113	Remote Similarity	NPC155506
0.5077	Remote Similarity	NPC217804
0.5039	Remote Similarity	NPC137627
0.5038	Remote Similarity	NPC476227

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC471051 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	2277
0.1-0.2	6487
0.2-0.3	384
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