NPASS Compound

Natural Product: NPC297079

Natural Product ID	NPC297079
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	UPNWIBPHYOJXOA-YDZHOCLMSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	11239826
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000257] Sphingolipids [CHEMONTID:0003258] Glycosphingolipids

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

Chemical Representations

RDKit 2D 146146 0 0 0 0 0 0 0 0999 V2000 36.1622 7.2429 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 34.7527 6.7299 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 33.3431 6.2169 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 31.9336 5.7038 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 30.5240 5.1908 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 29.1145 4.6778 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 27.7050 4.1648 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 26.2954 3.6517 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 24.8859 3.1387 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 23.4763 2.6257 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 22.0668 2.1126 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 20.6573 1.5996 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 19.2477 1.0866 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 17.8382 0.5735 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 16.4287 0.0605 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 15.0191 -0.4525 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 13.6096 -0.9656 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.2000 -1.4786 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.7905 -1.9916 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.3810 -2.5046 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.9714 -3.0177 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.4584 -1.6081 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9812 -1.3477 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 5.4681 0.0619 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0586 -0.4512 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6491 -0.9642 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3886 -2.4414 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9791 -1.9284 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1700 -2.8925 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0905 -4.3698 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5000 -4.8828 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6491 -5.8470 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7981 -6.8111 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6491 -3.9186 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1700 -5.8470 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5796 -3.4056 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1700 -0.9642 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.9551 1.4714 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5456 0.9584 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0325 2.3679 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5195 3.7775 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0065 5.1870 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4935 6.5965 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4576 7.7456 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9348 7.4851 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4121 7.2247 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8893 6.9642 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.3665 6.7037 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.8437 6.4432 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.3209 6.1828 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.7981 5.9223 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 14.2753 5.6618 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 15.7525 5.4014 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1360 0.4454 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.3647 1.9844 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 8.4226 -0.4591 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 8.4844 -4.4272 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 35.6492 8.6525 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 36.6752 5.8334 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 37.5717 7.7560 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 35.2657 5.3204 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 34.2396 8.1394 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 32.8301 7.6264 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 33.8561 4.8073 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 32.4466 4.2943 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 31.4205 7.1134 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 30.0110 6.6004 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 31.0371 3.7813 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 29.6275 3.2682 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 28.6015 6.0873 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 27.1919 5.5743 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 28.2180 2.7552 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 26.8085 2.2422 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 25.7824 5.0613 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 24.3729 4.5482 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 25.3989 1.7292 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 23.9894 1.2161 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 22.9633 4.0352 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 21.5538 3.5222 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 22.5798 0.7031 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 21.1703 0.1901 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 20.1442 3.0091 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 18.7347 2.4961 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 19.7608 -0.3230 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 18.3512 -0.8360 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 17.3252 1.9831 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 15.9156 1.4700 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 16.9417 -1.3490 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 15.5321 -1.8621 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 14.5061 0.9570 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 13.0965 0.4440 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 14.1226 -2.3751 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 12.7131 -2.8881 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 11.6870 -0.0690 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 11.3035 -3.4011 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 10.4531 -0.5300 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 9.8940 -3.9142 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 9.2242 -1.0128 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5619 -3.5307 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8777 0.5749 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6128 0.2097 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7396 -1.7876 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8774 -2.6242 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7291 -0.6293 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9200 -1.5935 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3984 -4.5526 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9139 -6.2636 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8321 -7.1050 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6132 -4.6979 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2077 -6.2981 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7116 -7.0605 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0181 -4.8400 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0905 0.5130 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6177 2.9330 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7023 -0.5334 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5710 2.0305 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3690 3.0489 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9291 4.2905 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1100 3.2644 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5969 4.6740 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4680 5.5244 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0162 6.8570 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9446 9.1551 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1953 8.9623 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8564 5.9872 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6725 8.7019 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1516 5.7475 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6288 5.4870 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1497 8.4414 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 8.6270 8.1809 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 8.1060 5.2265 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 9.5832 4.9660 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 10.1042 7.9205 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 11.5814 7.6600 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 11.0604 4.7056 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 12.5376 4.4451 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 13.0586 7.3995 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 14.5358 7.1390 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 14.0149 4.1846 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 15.4921 3.9241 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 16.0130 6.8786 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 17.2298 5.1409 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8780 1.2623 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6251 3.4617 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 9.9205 -0.5375 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 7.5203 -5.5763 0.0000 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 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 1 0 14 15 1 0 15 16 1 0 16 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 20 21 1 0 21 22 1 0 22 23 2 3 23 24 1 0 24 25 1 0 25 26 1 0 26 27 1 0 27 28 1 0 28 29 1 0 29 30 1 0 30 31 1 0 31 32 1 0 32 33 1 0 31 34 1 0 30 35 1 0 29 36 1 0 28 37 1 0 24 38 1 0 38 39 1 0 39 40 1 0 40 41 1 0 41 42 1 0 42 43 1 0 43 44 2 0 44 45 1 0 45 46 1 0 46 47 1 0 47 48 1 0 48 49 1 0 49 50 1 0 50 51 1 0 51 52 1 0 52 53 1 0 39 54 1 0 38 55 1 0 22 56 1 0 21 57 1 0 34 27 1 0 1 58 1 0 1 59 1 0 1 60 1 0 2 61 1 0 2 62 1 0 3 63 1 0 3 64 1 0 4 65 1 0 4 66 1 0 5 67 1 0 5 68 1 0 6 69 1 0 6 70 1 0 7 71 1 0 7 72 1 0 8 73 1 0 8 74 1 0 9 75 1 0 9 76 1 0 10 77 1 0 10 78 1 0 11 79 1 0 11 80 1 0 12 81 1 0 12 82 1 0 13 83 1 0 13 84 1 0 14 85 1 0 14 86 1 0 15 87 1 0 15 88 1 0 16 89 1 0 16 90 1 0 17 91 1 0 17 92 1 0 18 93 1 0 18 94 1 0 19 95 1 0 19 96 1 0 20 97 1 0 20 98 1 0 21 99 1 6 24100 1 6 25101 1 0 25102 1 0 27103 1 1 28104 1 6 29105 1 1 30106 1 6 31107 1 1 32108 1 0 32109 1 0 33110 1 0 35111 1 0 36112 1 0 37113 1 0 38114 1 6 39115 1 1 40116 1 0 40117 1 0 41118 1 0 41119 1 0 42120 1 0 42121 1 0 43122 1 0 44123 1 0 45124 1 0 45125 1 0 46126 1 0 46127 1 0 47128 1 0 47129 1 0 48130 1 0 48131 1 0 49132 1 0 49133 1 0 50134 1 0 50135 1 0 51136 1 0 51137 1 0 52138 1 0 52139 1 0 53140 1 0 53141 1 0 53142 1 0 54143 1 0 55144 1 0 56145 1 0 57146 1 0 M END

Standard InCHIKey	UPNWIBPHYOJXOA-YDZHOCLMSA-N
Standard InCHI	InChI=1S/C46H89NO10/c1-3-5-7-9-11-13-15-17-18-19-20-21-22-24-26-28-30-32-34-39(50)45(55)47-37(36-56-46-44(54)43(53)42(52)40(35-48)57-46)41(51)38(49)33-31-29-27-25-23-16-14-12-10-8-6-4-2/h25,27,37-44,46,48-54H,3-24,26,28-36H2,1-2H3,(H,47,55)/b27-25-/t37-,38+,39+,40+,41-,42+,43-,44+,46+/m0/s1
SMILES	CCCCCCCCCCCCCCCCCCCC[C@H](C(=N[C@@H](CO[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O)[C@@H]([C@@H](CCC/C=CCCCCCCCCC)O)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	815.65	Volume:	889.241 ? Van der Waals volume.
Dense:	0.917	LogP:	9.362 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	5.436 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.237 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	39.0	Rigid Bonds:	8.0
TPSA:	192.66 ? Topological Polar Surface Area.	H-Bond Acceptor:	11.0
H-Bond Donor:	8.0	Rings:	1.0
Heavy Atoms:	11.0

MedChem Properties

QED Drug-Likeness Score:	0.013	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.107	Fsp³:	0.935
MCE-18:	27.461 ? 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:	0.724	Fluc inhibitor:	0.052 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.007 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.012 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.04	Promiscuous compounds:	0.055

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.364	MDCK Permeability:	-4.765
Pgp-inhibitor:	0.0	Pgp-substrate:	0.012
PAMPA:	0.0 ? 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):	0.989
20% Bioavailability (F20%):	0.997	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.947
Plasma Protein Binding (PPB):	97.799%	Volume Distribution (VD):	0.516
Fu:	1.152% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.661
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.917
BSEP inhibitor:	0.311

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.001
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.999	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.187	CYP2D6-substrate:	0.005
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.0 ? 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):

2.433

Half-life (T1/2):

4.841

ADMET: Toxicity

hERG Blockers:	0.332	hERG Blockers (10um):	0.477
Human Hepatotoxicity (H-HT):	0.993	Drug-induced Liver Injury (DILI):	0.064
AMES Toxicity:	0.034	Rat Oral Acute Toxicity:	0.005
Maximum Recommended Daily Dose:	0.02	Skin Sensitization:	1.0
Carcinogencity:	0.02	Eye Corrosion:	0.001
Eye Irritation:	0.865	Respiratory Toxicity:	0.848
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	0.936
Hematotoxicity:	0.008	Drug-induced Nephrotoxicity:	0.404
Genotoxicity:	0.0	RPMI-8226 Immunitoxicity:	0.037
A549 Cytotoxicity:	0.998	Hek293 Cytotoxicity:	0.381
BCF:	0.591 ? 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:	5.305 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.695 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.692 ? 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
NPO12583	Sauromatum giganteum	Species	Araceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28394604]
NPO12583	Sauromatum giganteum	Species	Araceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO12583	Sauromatum giganteum	Species	Araceae	Eukaryota	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
EC50	1

Activity Type	# Activity
Cell line	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
NPT681	Cell line	PC-12	Rattus norvegicus	EC50	=	6600.0	nM	PMID[28394604]

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 NPC297079 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	19203
0.1-0.2	25649
0.2-0.3	4576
0.3-0.4	344
0.4-0.5	31
0.5-0.6	11
0.6-0.7	16
0.7-0.8	0
0.8-0.85	18
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	NPC61894
0.8065	Intermediate Similarity	NPC263545
0.8065	Intermediate Similarity	NPC473950
0.8065	Intermediate Similarity	NPC111567
0.8065	Intermediate Similarity	NPC186840
0.8065	Intermediate Similarity	NPC144916
0.8065	Intermediate Similarity	NPC486421
0.8065	Intermediate Similarity	NPC309898
0.8065	Intermediate Similarity	NPC273493
0.8065	Intermediate Similarity	NPC475125
0.8065	Intermediate Similarity	NPC486419
0.8065	Intermediate Similarity	NPC15851
0.8065	Intermediate Similarity	NPC115448
0.8065	Intermediate Similarity	NPC20819
0.8065	Intermediate Similarity	NPC486418
0.8065	Intermediate Similarity	NPC473604
0.8065	Intermediate Similarity	NPC486420
0.8065	Intermediate Similarity	NPC479188
0.8065	Intermediate Similarity	NPC81468
0.7692	Intermediate Similarity	NPC158445
0.7692	Intermediate Similarity	NPC157353
0.7692	Intermediate Similarity	NPC282088
0.7538	Intermediate Similarity	NPC156782
0.7538	Intermediate Similarity	NPC54961
0.7042	Intermediate Similarity	NPC8098
0.7042	Intermediate Similarity	NPC183449
0.7042	Intermediate Similarity	NPC197294
0.697	Remote Similarity	NPC282705
0.697	Remote Similarity	NPC182632
0.6716	Remote Similarity	NPC242503
0.6714	Remote Similarity	NPC3568
0.6714	Remote Similarity	NPC17290
0.6714	Remote Similarity	NPC192066
0.6714	Remote Similarity	NPC256570
0.6667	Remote Similarity	NPC43074
0.6667	Remote Similarity	NPC139782
0.6667	Remote Similarity	NPC74672
0.6667	Remote Similarity	NPC209047
0.6081	Remote Similarity	NPC23454
0.6081	Remote Similarity	NPC70323
0.6081	Remote Similarity	NPC262312
0.6081	Remote Similarity	NPC35269
0.6	Remote Similarity	NPC45313
0.5932	Remote Similarity	NPC217095
0.5932	Remote Similarity	NPC264417
0.5915	Remote Similarity	NPC475603
0.5915	Remote Similarity	NPC600808
0.5769	Remote Similarity	NPC201128
0.5479	Remote Similarity	NPC602861
0.5405	Remote Similarity	NPC473581
0.5286	Remote Similarity	NPC488689
0.5147	Remote Similarity	NPC469469
0.5085	Remote Similarity	NPC145627
0.5068	Remote Similarity	NPC21693

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC297079 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5662
0.1-0.2	3305
0.2-0.3	175
0.3-0.4	7
0.4-0.5	0
0.5-0.6	0
0.6-0.7	1
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
0.6667	Remote Similarity	NPD8522	Clinical (unspecified phase)

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