NPASS Compound

Natural Product: NPC325976

Natural Product ID	NPC325976
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Tyrocidine C
IUPAC Name	3-[(3R,6S,9S,12S,15S,18S,21S,24R,27S,30S)-21-(2-amino-2-oxoethyl)-9-(3-aminopropyl)-3-benzyl-15-[(4-hydroxyphenyl)methyl]-24,27-bis(1H-indol-3-ylmethyl)-6-(2-methylpropyl)-2,5,8,11,14,17,20,23,26,29-decaoxo-12-propan-2-yl-1,4,7,10,13,16,19,22,25,28-decazabicyclo[28.3.0]tritriacontan-18-yl]propanamide
Synonyms	Tyrocidine C
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL576465
PubChem CID	45485349
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 187194 0 0 0 0 0 0 0 0999 V2000 5.2760 0.0363 4.4532 N 0 0 0 0 0 0 0 0 0 0 0 0 4.8028 -0.8728 3.4499 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5111 -0.5956 2.1264 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9768 -1.5750 1.1420 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5976 -1.4367 -0.2387 C 0 0 2 0 0 0 0 0 0 0 0 0 5.3726 -0.1475 -0.7974 N 0 0 0 0 0 0 0 0 0 0 0 0 6.1688 0.8252 -0.6547 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3316 0.6899 0.0695 O 0 0 0 0 0 0 0 0 0 0 0 0 5.8017 2.1221 -1.3049 C 0 0 1 0 0 0 0 0 0 0 0 0 5.7036 3.1388 -0.3078 N 0 0 0 0 0 0 0 0 0 0 0 0 4.7475 3.9675 -0.1264 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8882 4.8746 0.9249 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4974 4.0334 -0.9579 C 0 0 2 0 0 0 0 0 0 0 0 0 3.8462 4.7433 -2.2886 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3468 6.1018 -2.0234 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6896 6.3577 -1.8275 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1489 7.6467 -1.5745 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2652 8.6991 -1.5131 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9136 8.4679 -1.7056 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4857 7.1749 -1.9567 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7809 9.9744 -1.2534 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4499 4.6866 -0.3235 N 0 0 0 0 0 0 0 0 0 0 0 0 1.6238 4.6190 0.5778 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4922 3.5435 1.4473 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7008 5.8438 0.7070 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9715 6.3433 2.1017 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2653 7.5889 2.4977 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6031 7.9701 3.9201 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3320 8.0581 4.8016 N 0 0 0 0 0 0 0 0 0 0 0 0 1.9001 8.2316 4.3124 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5814 5.4547 0.3677 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.2347 4.4831 -0.0321 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6792 3.2403 -0.2945 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7271 4.6161 -0.2729 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.1492 5.9212 0.3456 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9736 5.9797 1.8116 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7824 6.7687 2.4526 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.0426 5.2840 2.5512 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4779 3.4843 -0.0652 N 0 0 0 0 0 0 0 0 0 0 0 0 -4.4927 3.2129 0.5886 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1556 4.1502 1.3474 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1186 1.8120 0.6241 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.4275 0.8840 -0.1293 N 0 0 0 0 0 0 0 0 0 0 0 0 -4.2666 -0.3436 -0.2509 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8212 -1.5061 0.4568 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.0467 -2.7296 0.2878 N 0 0 0 0 0 0 0 0 0 0 0 0 -3.9957 -3.3695 -0.8102 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2387 -4.6140 -1.0511 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.2570 -4.9285 -0.0372 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.8871 -4.9664 -0.3154 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6229 -4.7505 -1.5221 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2393 -5.2159 0.5778 C 0 0 2 0 0 0 0 0 0 0 0 0 1.5174 -5.0997 -0.0251 N 0 0 0 0 0 0 0 0 0 0 0 0 2.0355 -4.2113 -0.7400 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4622 -4.3739 -1.2510 C 0 0 1 0 0 0 0 0 0 0 0 0 4.1811 -3.3019 -0.6681 N 0 0 0 0 0 0 0 0 0 0 0 0 4.9934 -2.4841 -1.1483 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3727 -2.4791 -2.4635 O 0 0 0 0 0 0 0 0 0 0 0 0 3.8799 -5.7500 -0.8844 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2623 -6.1615 -1.2810 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3504 -5.3303 -0.6951 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4152 -6.2830 -2.7817 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3115 -3.0741 -1.0674 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2176 -6.5301 1.3199 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2146 -7.7224 0.4790 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9756 -8.2465 0.0395 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0286 -9.3888 -0.7589 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1603 -10.0056 -1.1138 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3642 -9.5019 -0.6877 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3672 -8.3758 0.0962 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9975 -5.1768 1.1447 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3904 -5.6298 0.6852 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1929 -5.8193 -0.8294 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7228 -2.8494 -1.8962 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1407 -1.2197 1.8940 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6509 -2.4574 2.5920 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9621 -3.2010 3.5290 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7268 -4.2190 3.9389 N 0 0 0 0 0 0 0 0 0 0 0 0 -6.9113 -4.1872 3.3076 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8608 -3.0827 2.4662 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.9869 -2.8354 1.6974 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.0844 -3.6643 1.7875 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.1368 -4.7580 2.6202 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.0227 -5.0129 3.3895 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3381 -0.6741 -1.3197 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.6105 1.9334 0.4012 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.0136 2.5757 -0.8421 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.3948 3.8935 -0.9384 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.6706 4.1344 -2.2206 N 0 0 0 0 0 0 0 0 0 0 0 0 -7.4857 3.0286 -2.9613 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.0681 2.0362 -2.0910 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8115 0.7640 -2.6178 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9532 0.4595 -3.9522 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.3695 1.4706 -4.7962 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.6321 2.7368 -4.3060 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9357 2.4676 -2.2634 C 0 0 0 0 0 0 0 0 0 0 0 0 8.2326 2.5968 -1.5054 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0361 1.3100 -3.2591 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8219 0.8221 4.0406 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4678 0.5009 4.9463 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9901 -1.9314 3.7343 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7053 -0.7712 3.2829 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5831 -0.7269 2.2881 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2169 0.4273 1.7952 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0656 -2.6282 1.4824 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8812 -1.3989 1.0089 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6711 -1.6745 -0.1026 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8973 -0.1374 0.0139 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8733 2.0163 -1.8972 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5961 4.6723 1.6157 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2368 3.0010 -1.2345 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8787 4.8690 -2.8522 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4866 4.1420 -2.9314 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4412 5.5830 -1.8585 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2079 7.8488 -1.4229 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2366 9.3042 -1.6538 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4134 7.0381 -2.1015 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2494 10.4790 -1.9859 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9225 2.6356 1.2343 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1651 6.6003 0.0168 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8884 5.5304 2.8587 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0771 6.5944 2.1166 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7977 7.6551 2.3636 H 0 0 0 0 0 0 0 0 0 0 0 0 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H 0 0 0 0 0 0 0 0 0 0 0 0 6.4397 1.5332 -4.1659 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0966 1.0876 -3.4912 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 1 0 6 7 2 3 7 8 1 0 7 9 1 0 9 10 1 0 10 11 2 3 11 12 1 0 11 13 1 0 13 14 1 0 14 15 1 0 15 16 2 0 16 17 1 0 17 18 2 0 18 19 1 0 19 20 2 0 18 21 1 0 13 22 1 0 22 23 2 3 23 24 1 0 23 25 1 0 25 26 1 0 26 27 1 0 27 28 1 0 28 29 2 3 28 30 1 0 25 31 1 0 31 32 2 3 32 33 1 0 32 34 1 0 34 35 1 0 35 36 1 0 36 37 2 3 36 38 1 0 34 39 1 0 39 40 2 3 40 41 1 0 40 42 1 0 42 43 1 0 43 44 2 3 44 45 1 0 45 46 1 0 46 47 2 3 47 48 1 0 48 49 1 0 49 50 1 0 50 51 2 0 50 52 1 0 52 53 1 0 53 54 2 3 54 55 1 0 55 56 1 0 56 57 2 3 57 58 1 0 55 59 1 0 59 60 1 0 60 61 1 0 60 62 1 0 54 63 1 0 52 64 1 0 64 65 1 0 65 66 2 0 66 67 1 0 67 68 2 0 68 69 1 0 69 70 2 0 49 71 1 0 71 72 1 0 72 73 1 0 47 74 1 0 45 75 1 0 75 76 1 0 76 77 2 0 77 78 1 0 78 79 1 0 79 80 2 0 80 81 1 0 81 82 2 0 82 83 1 0 83 84 2 0 44 85 1 0 42 86 1 0 86 87 1 0 87 88 2 0 88 89 1 0 89 90 1 0 90 91 2 0 91 92 1 0 92 93 2 0 93 94 1 0 94 95 2 0 9 96 1 0 96 97 1 0 96 98 1 0 57 5 1 0 70 65 1 0 80 76 1 0 91 87 1 0 20 15 1 0 73 48 1 0 84 79 1 0 95 90 1 0 1 99 1 0 1100 1 0 2101 1 0 2102 1 0 3103 1 0 3104 1 0 4105 1 0 4106 1 0 5107 1 1 8108 1 0 9109 1 6 12110 1 0 13111 1 6 14112 1 0 14113 1 0 16114 1 0 17115 1 0 19116 1 0 20117 1 0 21118 1 0 24119 1 0 25120 1 6 26121 1 0 26122 1 0 27123 1 0 27124 1 0 29125 1 0 30126 1 0 33127 1 0 34128 1 6 35129 1 0 35130 1 0 37131 1 0 38132 1 0 41133 1 0 42134 1 1 45135 1 6 48136 1 6 52137 1 1 55138 1 6 58139 1 0 59140 1 0 59141 1 0 60142 1 0 61143 1 0 61144 1 0 61145 1 0 62146 1 0 62147 1 0 62148 1 0 63149 1 0 64150 1 0 64151 1 0 66152 1 0 67153 1 0 68154 1 0 69155 1 0 70156 1 0 71157 1 0 71158 1 0 72159 1 0 72160 1 0 73161 1 0 73162 1 0 74163 1 0 75164 1 0 75165 1 0 77166 1 0 78167 1 0 81168 1 0 82169 1 0 83170 1 0 84171 1 0 85172 1 0 86173 1 0 86174 1 0 88175 1 0 89176 1 0 92177 1 0 93178 1 0 94179 1 0 95180 1 0 96181 1 0 97182 1 0 97183 1 0 97184 1 0 98185 1 0 98186 1 0 98187 1 0 M END

Standard InCHIKey	NJMWWUADORPGGY-AJOXBXEMSA-N
Standard InCHI	InChI=1S/C70H89N15O13/c1-38(2)30-51-63(91)83-56(32-40-14-6-5-7-15-40)70(98)85-29-13-21-57(85)68(96)82-54(34-43-37-75-48-19-11-9-17-46(43)48)65(93)80-53(33-42-36-74-47-18-10-8-16-45(42)47)64(92)81-55(35-59(73)88)66(94)76-50(26-27-58(72)87)62(90)79-52(31-41-22-24-44(86)25-23-41)67(95)84-60(39(3)4)69(97)77-49(20-12-28-71)61(89)78-51/h5-11,14-19,22-25,36-39,49-57,60,74-75,86H,12-13,20-21,26-35,71H2,1-4H3,(H2,72,87)(H2,73,88)(H,76,94)(H,77,97)(H,78,89)(H,79,90)(H,80,93)(H,81,92)(H,82,96)(H,83,91)(H,84,95)/t49-,50-,51-,52-,53+,54-,55-,56+,57-,60-/m0/s1
SMILES	NCCC[C@@H]1N=C(O)[C@@H](N=C(O)[C@H](Cc2ccc(cc2)O)N=C(O)[C@H](CCC(=N)O)N=C(O)[C@H](CC(=N)O)N=C(O)[C@H](N=C([C@@H](N=C([C@H]2N(C(=O)[C@H](N=C([C@@H](N=C1O)CC(C)C)O)Cc1ccccc1)CCC2)O)Cc1c[nH]c2c1cccc2)O)Cc1c[nH]c2c1cccc2)C(C)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	1347.68	Volume:	1361.5 ? Van der Waals volume.
Dense:	0.99	LogP:	0.245 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	0.985 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.317 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	19.0	Rigid Bonds:	69.0
TPSA:	479.61 ? Topological Polar Surface Area.	H-Bond Acceptor:	28.0
H-Bond Donor:	18.0	Rings:	8.0
Heavy Atoms:	28.0

MedChem Properties

QED Drug-Likeness Score:	0.026	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	7.751	Fsp³:	0.429
MCE-18:	189.08 ? 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:	0.999	Fluc inhibitor:	0.268 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.185 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.897 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.004	Promiscuous compounds:	0.262

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.33	MDCK Permeability:	-5.192
Pgp-inhibitor:	0.813	Pgp-substrate:	1.0
PAMPA:	0.989 ? 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):	0.057
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:	0.749
Plasma Protein Binding (PPB):	68.064%	Volume Distribution (VD):	-0.274
Fu:	28.806% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.978	BCRP inhibitor:	0.025
BSEP inhibitor:	1.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	1.0	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:	0.052 ? 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):

-0.315

Half-life (T1/2):

2.976

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:	0.002	Rat Oral Acute Toxicity:	0.98
Maximum Recommended Daily Dose:	0.962	Skin Sensitization:	1.0
Carcinogencity:	0.227	Eye Corrosion:	0.0
Eye Irritation:	0.0	Respiratory Toxicity:	0.614
Drug-induced Neurotoxicity:	0.167	Ototoxicity:	1.0
Hematotoxicity:	0.696	Drug-induced Nephrotoxicity:	1.0
Genotoxicity:	1.0	RPMI-8226 Immunitoxicity:	0.0
A549 Cytotoxicity:	0.0	Hek293 Cytotoxicity:	0.0
BCF:	0.216 ? 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:	3.348 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.979 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.952 ? 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
NPO23673	Brevibacillus brevis	Species	Paenibacillaceae	Bacteria	n.a.	n.a.	n.a.	PMID[4320358]

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	2
IC50	3
ICmax	3

Activity Type	# Activity
Organism	8

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
NPT729	Organism	Micrococcus luteus	Micrococcus luteus	IC50	=	6400.0	nM	PMID[19586775]
NPT729	Organism	Micrococcus luteus	Micrococcus luteus	ICmax	=	9.0	uM	PMID[19586775]
NPT564	Organism	Listeria monocytogenes	Listeria monocytogenes	Activity	=	1.48	%	PMID[19586775]
NPT564	Organism	Listeria monocytogenes	Listeria monocytogenes	Activity	=	66.0	%	PMID[19586775]
NPT564	Organism	Listeria monocytogenes	Listeria monocytogenes	IC50	=	9500.0	nM	PMID[19586775]
NPT564	Organism	Listeria monocytogenes	Listeria monocytogenes	ICmax	=	13.0	uM	PMID[19586775]
NPT564	Organism	Listeria monocytogenes	Listeria monocytogenes	IC50	=	7000.0	nM	PMID[19586775]
NPT564	Organism	Listeria monocytogenes	Listeria monocytogenes	ICmax	=	11.0	uM	PMID[19586775]

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
Listeria monocytogenes	n.a.	T1/2	=	0.52	hr	PMID[19586775]

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 NPC325976 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	25195
0.1-0.2	23002
0.2-0.3	1163
0.3-0.4	311
0.4-0.5	128
0.5-0.6	43
0.6-0.7	9
0.7-0.8	1
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC326363
0.7981	Intermediate Similarity	NPC328649
0.7863	Intermediate Similarity	NPC489555
0.7027	Intermediate Similarity	NPC31385
0.6609	Remote Similarity	NPC110602
0.6609	Remote Similarity	NPC479071
0.6555	Remote Similarity	NPC479076
0.6522	Remote Similarity	NPC484874
0.6356	Remote Similarity	NPC479075
0.6333	Remote Similarity	NPC479073
0.6218	Remote Similarity	NPC162860
0.6179	Remote Similarity	NPC75726
0.6026	Remote Similarity	NPC479141
0.5984	Remote Similarity	NPC479065
0.5968	Remote Similarity	NPC479066
0.5789	Remote Similarity	NPC489625
0.5726	Remote Similarity	NPC293917
0.5714	Remote Similarity	NPC479574
0.5702	Remote Similarity	NPC241794
0.5691	Remote Similarity	NPC155143
0.5656	Remote Similarity	NPC54420
0.5548	Remote Similarity	NPC75634
0.5546	Remote Similarity	NPC107077
0.5546	Remote Similarity	NPC483341
0.5538	Remote Similarity	NPC100321
0.5537	Remote Similarity	NPC223791
0.5536	Remote Similarity	NPC487314
0.5529	Remote Similarity	NPC477634
0.5505	Remote Similarity	NPC202198
0.5489	Remote Similarity	NPC483985
0.5455	Remote Similarity	NPC486515
0.5455	Remote Similarity	NPC489829
0.5431	Remote Similarity	NPC482066
0.5422	Remote Similarity	NPC484965
0.5412	Remote Similarity	NPC485244
0.5391	Remote Similarity	NPC136797
0.5357	Remote Similarity	NPC479072
0.5291	Remote Similarity	NPC477633
0.5273	Remote Similarity	NPC489225
0.5269	Remote Similarity	NPC477635
0.5268	Remote Similarity	NPC314603
0.5259	Remote Similarity	NPC486528
0.5253	Remote Similarity	NPC320968
0.5226	Remote Similarity	NPC153400
0.5207	Remote Similarity	NPC486506
0.5207	Remote Similarity	NPC485247
0.5207	Remote Similarity	NPC486514
0.5197	Remote Similarity	NPC284549
0.5139	Remote Similarity	NPC484875
0.5134	Remote Similarity	NPC479872
0.5126	Remote Similarity	NPC213629
0.512	Remote Similarity	NPC489538
0.5109	Remote Similarity	NPC69843
0.5094	Remote Similarity	NPC17059
0.5081	Remote Similarity	NPC487116
0.503	Remote Similarity	NPC489535

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC325976 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3656
0.1-0.2	5203
0.2-0.3	244
0.3-0.4	31
0.4-0.5	12
0.5-0.6	3
0.6-0.7	0
0.7-0.8	1
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
0.7232	Intermediate Similarity	NPD8405	Pre-clinical
0.5726	Remote Similarity	NPD7621	Clinical (unspecified phase)
0.5255	Remote Similarity	NPD8493	Clinical (unspecified phase)
0.5041	Remote Similarity	NPD7948	Phase 1

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