NPASS Compound

Natural Product: NPC475333

Natural Product ID	NPC475333
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	HSOMTBUZSIVDQK-OJQSNVAUSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL503620
PubChem CID	44575743
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001013] Steroidal glycosides [CHEMONTID:0002364] Steroidal saponins

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 130138 0 0 0 0 0 0 0 0999 V2000 -5.1390 -3.7723 1.1074 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.7364 -2.5534 1.4645 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1983 -1.4496 0.6170 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.8043 -1.4093 0.8606 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4541 -0.0698 0.6547 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.0673 0.0371 0.6672 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6676 0.7910 1.7639 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8265 -0.0816 2.6772 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2308 -0.7301 1.8016 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1367 0.3236 1.1733 C 0 0 1 0 0 0 0 0 0 0 0 0 0.6335 1.6722 1.4529 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4139 2.6702 1.7505 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8955 2.5711 1.8421 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3760 1.3275 1.1189 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5515 0.1627 1.5642 C 0 0 2 0 0 0 0 0 0 0 0 0 3.1429 -1.1555 1.0890 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5345 -1.2980 1.6404 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3663 -0.2030 1.0191 C 0 0 1 0 0 0 0 0 0 0 0 0 4.7914 1.0947 1.5545 C 0 0 1 0 0 0 0 0 0 0 0 0 5.8027 2.0713 1.0727 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1092 1.3332 1.4122 C 0 0 1 0 0 0 0 0 0 0 0 0 6.7631 -0.1172 1.5106 C 0 0 2 0 0 0 0 0 0 0 0 0 7.7576 -0.8573 0.6499 C 0 0 2 0 0 0 0 0 0 0 0 0 8.3337 -1.9756 1.4965 C 0 0 0 0 0 0 0 0 0 0 0 0 8.7797 0.2464 0.3912 C 0 0 2 0 0 0 0 0 0 0 0 0 8.0574 1.4370 0.4327 O 0 0 0 0 0 0 0 0 0 0 0 0 9.3111 0.0209 -1.0137 C 0 0 0 0 0 0 0 0 0 0 0 0 10.3394 -1.0881 -0.9427 C 0 0 0 0 0 0 0 0 0 0 0 0 11.4969 -0.6895 -0.0763 C 0 0 2 0 0 0 0 0 0 0 0 0 11.0322 0.3514 0.9075 C 0 0 0 0 0 0 0 0 0 0 0 0 9.7464 0.1607 1.3613 O 0 0 0 0 0 0 0 0 0 0 0 0 12.5609 -0.0740 -0.9756 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2647 -0.3067 -0.4807 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8509 1.9895 1.4025 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0242 0.1252 -0.3481 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0446 0.4570 -0.6355 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.4512 -0.6670 -1.5625 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.3472 -1.6702 -0.8664 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.6399 -1.5370 -1.3299 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.1423 -2.6704 -1.9414 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.4247 -2.5161 -3.2830 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.2600 -3.7587 -3.8944 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.8280 -4.8925 -3.0704 C 0 0 2 0 0 0 0 0 0 0 0 0 -8.8448 -4.4150 -2.0698 C 0 0 2 0 0 0 0 0 0 0 0 0 -8.3343 -3.2458 -1.2540 C 0 0 2 0 0 0 0 0 0 0 0 0 -9.3596 -2.2952 -1.2160 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.1151 -5.4828 -1.1942 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.8279 -5.6672 -2.4809 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2812 -1.2552 -2.0247 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0822 1.3391 -0.3942 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.7465 2.5940 -0.8708 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.8625 3.4906 0.1802 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.2106 3.7132 0.4163 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.4716 4.1736 1.8357 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6649 4.7822 -0.5828 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.8367 4.5646 -1.8420 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.6878 3.0494 -1.9743 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.1218 2.8092 -3.2227 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.5535 5.0848 -1.6411 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.0297 4.7026 -0.8373 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.4595 -4.5095 1.6664 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8183 -2.6056 1.5658 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3481 -2.3585 2.5088 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6380 -0.4992 0.9613 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8656 0.4814 1.5218 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5458 1.1189 2.3472 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4117 0.4980 3.5011 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4783 -0.8836 3.0559 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2926 -1.2526 0.9899 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8495 -1.4336 2.3462 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0056 3.6593 1.9534 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1606 2.5287 2.9127 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3424 3.4869 1.4197 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3206 1.5664 0.0466 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6074 0.1370 2.6823 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0752 -1.2677 -0.0038 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5484 -1.9648 1.5411 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4896 -1.1131 2.7256 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9708 -2.2881 1.4707 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7875 0.9932 2.6651 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7214 2.2011 -0.0054 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7661 3.0439 1.6438 H 0 0 0 0 0 0 0 0 0 0 0 0 7.4792 1.7624 2.3655 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8029 -0.4236 2.5717 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3204 -1.2305 -0.2809 H 0 0 0 0 0 0 0 0 0 0 0 0 9.3251 -1.7246 1.8934 H 0 0 0 0 0 0 0 0 0 0 0 0 8.3188 -2.9596 0.9458 H 0 0 0 0 0 0 0 0 0 0 0 0 7.6772 -2.1720 2.3949 H 0 0 0 0 0 0 0 0 0 0 0 0 9.7813 0.9411 -1.4202 H 0 0 0 0 0 0 0 0 0 0 0 0 8.4867 -0.3590 -1.6690 H 0 0 0 0 0 0 0 0 0 0 0 0 9.8611 -2.0308 -0.6404 H 0 0 0 0 0 0 0 0 0 0 0 0 10.6753 -1.2467 -2.0070 H 0 0 0 0 0 0 0 0 0 0 0 0 11.9261 -1.5728 0.4502 H 0 0 0 0 0 0 0 0 0 0 0 0 11.1865 1.3741 0.5270 H 0 0 0 0 0 0 0 0 0 0 0 0 11.7008 0.2519 1.8057 H 0 0 0 0 0 0 0 0 0 0 0 0 12.7497 0.9820 -0.6742 H 0 0 0 0 0 0 0 0 0 0 0 0 12.2170 -0.0261 -2.0282 H 0 0 0 0 0 0 0 0 0 0 0 0 13.5074 -0.6520 -0.9428 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3294 0.0691 -0.8850 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3436 -1.3775 -0.7520 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0862 0.2268 -0.9996 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0273 2.3557 0.3817 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1007 2.8111 2.1029 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7164 -0.9207 -0.5727 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9308 0.4182 -0.8763 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1926 0.7678 -0.6932 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2327 1.0099 -1.1456 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9555 -0.2155 -2.4379 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9222 -2.6798 -1.0695 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3133 -3.4358 -1.8854 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1626 -3.9368 -3.9711 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.6479 -3.7539 -4.9305 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.3639 -5.5643 -3.7903 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.7897 -4.1998 -2.6024 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.1416 -3.5297 -0.2001 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.4752 -1.9735 -2.1628 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.3549 -6.2627 -1.7542 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1429 -5.8985 -1.5666 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6164 -0.5178 -2.1913 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7205 2.6042 -1.3343 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7669 2.7645 0.2624 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1808 3.3689 2.5150 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9711 5.1264 2.0652 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5667 4.3079 1.9212 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3996 5.7551 -0.1328 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2787 5.0257 -2.7298 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6699 2.5471 -1.9419 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1380 2.7087 -3.1815 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5096 6.0495 -1.9320 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.4929 4.6550 0.0180 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 2 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 1 0 23 24 1 0 23 25 1 0 25 26 1 6 25 27 1 0 27 28 1 0 28 29 1 0 29 30 1 0 30 31 1 0 29 32 1 0 18 33 1 6 11 34 1 0 10 35 1 6 5 36 1 0 36 37 1 0 37 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 1 0 44 45 1 0 45 46 1 0 44 47 1 0 43 48 1 0 37 49 1 0 36 50 1 0 50 51 1 0 51 52 1 0 52 53 1 0 53 54 1 0 53 55 1 0 55 56 1 0 56 57 1 0 57 58 1 0 56 59 1 0 55 60 1 0 38 3 1 0 45 40 1 0 57 51 1 0 34 7 1 0 15 10 1 0 22 18 1 0 31 25 1 0 19 14 1 0 26 21 1 0 1 61 1 0 2 62 1 0 2 63 1 0 3 64 1 1 5 65 1 1 7 66 1 1 8 67 1 0 8 68 1 0 9 69 1 0 9 70 1 0 12 71 1 0 13 72 1 0 13 73 1 0 14 74 1 6 15 75 1 1 16 76 1 0 16 77 1 0 17 78 1 0 17 79 1 0 19 80 1 1 20 81 1 0 20 82 1 0 21 83 1 1 22 84 1 1 23 85 1 6 24 86 1 0 24 87 1 0 24 88 1 0 27 89 1 0 27 90 1 0 28 91 1 0 28 92 1 0 29 93 1 1 30 94 1 0 30 95 1 0 32 96 1 0 32 97 1 0 32 98 1 0 33 99 1 0 33100 1 0 33101 1 0 34102 1 0 34103 1 0 35104 1 0 35105 1 0 35106 1 0 36107 1 6 37108 1 6 38109 1 1 40110 1 6 42111 1 0 42112 1 0 43113 1 6 44114 1 6 45115 1 1 46116 1 0 47117 1 0 48118 1 0 49119 1 0 51120 1 6 53121 1 6 54122 1 0 54123 1 0 54124 1 0 55125 1 1 56126 1 6 57127 1 6 58128 1 0 59129 1 0 60130 1 0 M END

Standard InCHIKey	HSOMTBUZSIVDQK-OJQSNVAUSA-N
Standard InCHI	InChI=1S/C44H70O16/c1-19-8-13-44(54-17-19)20(2)30-28(60-44)15-26-24-7-6-22-14-23(9-11-42(22,4)25(24)10-12-43(26,30)5)56-41-38(59-40-35(51)33(49)31(47)21(3)55-40)36(52)37(29(16-45)57-41)58-39-34(50)32(48)27(46)18-53-39/h6,19-21,23-41,45-52H,7-18H2,1-5H3/t19-,20+,21+,23+,24-,25+,26+,27-,28+,29-,30+,31+,32-,33-,34+,35-,36+,37-,38-,39+,40+,41-,42+,43+,44-/m1/s1
SMILES	OC[C@H]1O[C@@H](O[C@H]2CC[C@]3(C(=CC[C@@H]4[C@@H]3CC[C@]3([C@H]4C[C@H]4[C@@H]3[C@H](C)[C@]3(O4)CC[C@H](CO3)C)C)C2)C)[C@@H]([C@H]([C@@H]1O[C@@H]1OC[C@H]([C@H]([C@@H]1O)O)O)O)O[C@@H]1O[C@@H](C)[C@@H]([C@H]([C@H]1O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	854.47	Volume:	830.579 ? Van der Waals volume.
Dense:	1.029	LogP:	2.64 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.439 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.756 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	7.0	Rigid Bonds:	48.0
TPSA:	235.68 ? Topological Polar Surface Area.	H-Bond Acceptor:	16.0
H-Bond Donor:	8.0	Rings:	9.0
Heavy Atoms:	16.0

MedChem Properties

QED Drug-Likeness Score:	0.166	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	6.65	Fsp³:	0.955
MCE-18:	226.395 ? 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:	0.816	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.005 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.0 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.208	Promiscuous compounds:	0.016

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.142	MDCK Permeability:	-5.071
Pgp-inhibitor:	0.0	Pgp-substrate:	0.948
PAMPA:	0.999 ? 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):	0.007
20% Bioavailability (F20%):	0.621	30% Bioavailability (F30%):	0.921
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.048
Plasma Protein Binding (PPB):	63.814%	Volume Distribution (VD):	-0.388
Fu:	28.193% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.478
BSEP inhibitor:	0.284

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.001	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.002
CYP3A4-inhibitor:	1.0	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.969
HLM stability:	0.979 ? 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):

0.381

Half-life (T1/2):

2.712

ADMET: Toxicity

hERG Blockers:	0.051	hERG Blockers (10um):	0.187
Human Hepatotoxicity (H-HT):	0.323	Drug-induced Liver Injury (DILI):	0.94
AMES Toxicity:	0.803	Rat Oral Acute Toxicity:	0.016
Maximum Recommended Daily Dose:	0.051	Skin Sensitization:	1.0
Carcinogencity:	0.04	Eye Corrosion:	0.0
Eye Irritation:	0.001	Respiratory Toxicity:	0.002
Drug-induced Neurotoxicity:	0.001	Ototoxicity:	0.997
Hematotoxicity:	0.106	Drug-induced Nephrotoxicity:	0.693
Genotoxicity:	0.003	RPMI-8226 Immunitoxicity:	0.333
A549 Cytotoxicity:	0.745	Hek293 Cytotoxicity:	0.842
BCF:	1.923 ? 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:	3.587 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.83 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.187 ? 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
NPO19123	Polygonatum zanlanscianense	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15620239]
NPO19123	Polygonatum zanlanscianense	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19123	Polygonatum zanlanscianense	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19123	Polygonatum zanlanscianense	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19123	Polygonatum zanlanscianense	Species	Asparagaceae	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
IC50	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
NPT165	Cell line	HeLa	Homo sapiens	IC50	=	14.57	ug.mL-1	PMID[20196571]

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 NPC475333 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	24095
0.1-0.2	22320
0.2-0.3	2538
0.3-0.4	633
0.4-0.5	120
0.5-0.6	75
0.6-0.7	34
0.7-0.8	0
0.8-0.85	6
0.85-0.9	6
0.9-0.95	4
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC224098
1.0	High Similarity	NPC208383
0.9255	High Similarity	NPC470433
0.9255	High Similarity	NPC46190
0.9255	High Similarity	NPC171073
0.9126	High Similarity	NPC480556
0.8969	High Similarity	NPC480555
0.8969	High Similarity	NPC150372
0.8835	High Similarity	NPC232054
0.87	High Similarity	NPC269297
0.87	High Similarity	NPC222202
0.8571	High Similarity	NPC248746
0.8447	Intermediate Similarity	NPC480554
0.835	Intermediate Similarity	NPC194207
0.835	Intermediate Similarity	NPC22779
0.8286	Intermediate Similarity	NPC480553
0.8165	Intermediate Similarity	NPC224314
0.8119	Intermediate Similarity	NPC42171
0.78	Intermediate Similarity	NPC113044
0.78	Intermediate Similarity	NPC283829
0.78	Intermediate Similarity	NPC161676
0.7778	Intermediate Similarity	NPC470432
0.7778	Intermediate Similarity	NPC230507
0.7573	Intermediate Similarity	NPC602423
0.757	Intermediate Similarity	NPC32361
0.7431	Intermediate Similarity	NPC249265
0.7429	Intermediate Similarity	NPC300557
0.73	Intermediate Similarity	NPC19400
0.7264	Intermediate Similarity	NPC471464
0.717	Intermediate Similarity	NPC477809
0.7115	Intermediate Similarity	NPC14704
0.7103	Intermediate Similarity	NPC6806
0.7091	Intermediate Similarity	NPC13193
0.7087	Intermediate Similarity	NPC485595
0.7087	Intermediate Similarity	NPC6295
0.7041	Intermediate Similarity	NPC181845
0.7009	Intermediate Similarity	NPC477808
0.6972	Remote Similarity	NPC73243
0.6972	Remote Similarity	NPC244086
0.6972	Remote Similarity	NPC84956
0.6944	Remote Similarity	NPC124677
0.6937	Remote Similarity	NPC309278
0.6881	Remote Similarity	NPC475182
0.6847	Remote Similarity	NPC247037
0.6638	Remote Similarity	NPC31896
0.6609	Remote Similarity	NPC23808
0.6609	Remote Similarity	NPC87998
0.6604	Remote Similarity	NPC94272
0.6577	Remote Similarity	NPC128572
0.641	Remote Similarity	NPC477811
0.6404	Remote Similarity	NPC475550
0.6396	Remote Similarity	NPC122819
0.6389	Remote Similarity	NPC141433
0.6389	Remote Similarity	NPC195297
0.6356	Remote Similarity	NPC308140
0.633	Remote Similarity	NPC305423
0.6286	Remote Similarity	NPC250393
0.626	Remote Similarity	NPC210569
0.6239	Remote Similarity	NPC218571
0.6239	Remote Similarity	NPC487615
0.6228	Remote Similarity	NPC294129
0.6182	Remote Similarity	NPC160426
0.6168	Remote Similarity	NPC306131
0.6168	Remote Similarity	NPC200802
0.6126	Remote Similarity	NPC475351
0.6117	Remote Similarity	NPC165439
0.6091	Remote Similarity	NPC70204
0.6083	Remote Similarity	NPC287885
0.6053	Remote Similarity	NPC274200
0.6038	Remote Similarity	NPC477451
0.6	Remote Similarity	NPC15918
0.5984	Remote Similarity	NPC305771
0.5984	Remote Similarity	NPC94072
0.5984	Remote Similarity	NPC169816
0.5983	Remote Similarity	NPC486386
0.5948	Remote Similarity	NPC97700
0.5948	Remote Similarity	NPC30856
0.5932	Remote Similarity	NPC475625
0.5929	Remote Similarity	NPC98696
0.5882	Remote Similarity	NPC254255
0.5812	Remote Similarity	NPC102016
0.5812	Remote Similarity	NPC95051
0.5789	Remote Similarity	NPC40440
0.5739	Remote Similarity	NPC265275
0.5736	Remote Similarity	NPC263359
0.5727	Remote Similarity	NPC211354
0.5701	Remote Similarity	NPC297348
0.5701	Remote Similarity	NPC249204
0.5701	Remote Similarity	NPC48339
0.5701	Remote Similarity	NPC141769
0.5701	Remote Similarity	NPC477547
0.5657	Remote Similarity	NPC100451
0.5641	Remote Similarity	NPC249553
0.5625	Remote Similarity	NPC107962
0.562	Remote Similarity	NPC232037
0.561	Remote Similarity	NPC132080
0.5603	Remote Similarity	NPC475643
0.5556	Remote Similarity	NPC325828
0.5556	Remote Similarity	NPC177834
0.5546	Remote Similarity	NPC475247
0.5517	Remote Similarity	NPC473601
0.5514	Remote Similarity	NPC485594
0.5508	Remote Similarity	NPC51172
0.5508	Remote Similarity	NPC49032
0.55	Remote Similarity	NPC115165
0.5496	Remote Similarity	NPC244431
0.5495	Remote Similarity	NPC206003
0.5495	Remote Similarity	NPC473610
0.5424	Remote Similarity	NPC469348
0.541	Remote Similarity	NPC116756
0.5405	Remote Similarity	NPC222731
0.5403	Remote Similarity	NPC476112
0.5403	Remote Similarity	NPC307534
0.5391	Remote Similarity	NPC475670
0.5378	Remote Similarity	NPC182900
0.5372	Remote Similarity	NPC475319
0.5349	Remote Similarity	NPC477807
0.531	Remote Similarity	NPC107188
0.5304	Remote Similarity	NPC15249
0.5304	Remote Similarity	NPC25455
0.53	Remote Similarity	NPC235126
0.53	Remote Similarity	NPC242419
0.5299	Remote Similarity	NPC112274
0.529	Remote Similarity	NPC329807
0.5285	Remote Similarity	NPC473518
0.5267	Remote Similarity	NPC79900
0.5263	Remote Similarity	NPC264101
0.5254	Remote Similarity	NPC42482
0.5254	Remote Similarity	NPC486388
0.5238	Remote Similarity	NPC233433
0.5177	Remote Similarity	NPC481189
0.5172	Remote Similarity	NPC306991
0.5159	Remote Similarity	NPC83137
0.5141	Remote Similarity	NPC329727
0.5116	Remote Similarity	NPC470866
0.51	Remote Similarity	NPC207617
0.51	Remote Similarity	NPC607440
0.5094	Remote Similarity	NPC144790
0.5094	Remote Similarity	NPC149400
0.5094	Remote Similarity	NPC88962
0.5089	Remote Similarity	NPC294686
0.5089	Remote Similarity	NPC234352
0.5082	Remote Similarity	NPC150057
0.5082	Remote Similarity	NPC147753
0.5041	Remote Similarity	NPC184617
0.5039	Remote Similarity	NPC167183

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC475333 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7667
0.1-0.2	1396
0.2-0.3	77
0.3-0.4	5
0.4-0.5	1
0.5-0.6	3
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
0.6396	Remote Similarity	NPD8449	Approved
0.5556	Remote Similarity	NPD8171	Phase 2
0.5082	Remote Similarity	NPD8450	Suspended
0.5043	Remote Similarity	NPD8170	Phase 2

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