NPASS Compound

Natural Product: NPC182900

Natural Product ID	NPC182900
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Polygonatoside A
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL444418
PubChem CID	11182156
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 134142 0 0 0 0 0 0 0 0999 V2000 12.8642 -0.5888 -2.5336 O 0 0 0 0 0 0 0 0 0 0 0 0 11.6857 -0.3304 -1.8410 C 0 0 0 0 0 0 0 0 0 0 0 0 11.6257 1.1664 -1.6170 C 0 0 1 0 0 0 0 0 0 0 0 0 10.5102 1.5845 -0.9365 O 0 0 0 0 0 0 0 0 0 0 0 0 10.4312 1.1976 0.3798 C 0 0 1 0 0 0 0 0 0 0 0 0 9.9513 -0.1140 0.4351 O 0 0 0 0 0 0 0 0 0 0 0 0 8.7070 -0.1708 1.0614 C 0 0 0 0 0 0 0 0 0 0 0 0 8.2727 -1.6207 1.0778 C 0 0 2 0 0 0 0 0 0 0 0 0 8.1849 -2.0948 -0.3542 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0661 -1.3458 -1.0379 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8144 -1.5176 -0.2508 C 0 0 1 0 0 0 0 0 0 0 0 0 5.9807 -2.3008 0.8883 O 0 0 0 0 0 0 0 0 0 0 0 0 6.9306 -1.7842 1.7430 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2695 -0.2931 0.1774 O 0 0 0 0 0 0 0 0 0 0 0 0 4.0754 -0.6704 0.7412 C 0 0 2 0 0 0 0 0 0 0 0 0 3.4869 -1.6251 -0.2787 C 0 0 2 0 0 0 0 0 0 0 0 0 4.6659 -2.1237 -1.0265 C 0 0 2 0 0 0 0 0 0 0 0 0 4.7403 -3.6390 -0.7992 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5415 -0.7469 -1.0269 C 0 0 2 0 0 0 0 0 0 0 0 0 1.9013 -0.0278 0.1758 C 0 0 1 0 0 0 0 0 0 0 0 0 3.0826 0.4915 0.8707 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9082 0.9351 -0.3747 C 0 0 2 0 0 0 0 0 0 0 0 0 0.4986 2.0132 0.5647 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9037 1.8559 1.0709 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8605 1.2988 0.3426 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4995 0.8271 -1.0100 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.2248 0.0462 -0.8451 C 0 0 1 0 0 0 0 0 0 0 0 0 0.1929 -0.7465 -2.0368 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4600 -1.4436 -1.7155 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5856 -2.6041 -2.0338 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2896 2.0225 -1.9494 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5592 -0.0170 -1.6277 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9106 0.6004 -1.3428 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1584 0.3133 0.1454 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.2109 1.1845 0.9118 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4614 0.5260 0.5180 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0531 -0.6667 0.9277 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.1108 -0.9410 0.0736 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.0868 -1.7279 0.6789 C 0 0 2 0 0 0 0 0 0 0 0 0 -8.9687 -2.2586 -0.4511 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.8804 -0.8545 1.6222 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.9173 -0.0903 2.4921 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.4960 -0.6016 2.3742 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.3531 -1.8582 2.9599 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.9340 1.2808 2.2217 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.6573 0.0043 0.8385 O 0 0 0 0 0 0 0 0 0 0 0 0 -11.0174 -0.1882 1.0530 C 0 0 2 0 0 0 0 0 0 0 0 0 -11.7041 -0.6236 -0.0501 O 0 0 0 0 0 0 0 0 0 0 0 0 -12.8292 0.1444 -0.3358 C 0 0 2 0 0 0 0 0 0 0 0 0 -13.5585 -0.4326 -1.5321 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.7029 -0.4240 -2.6204 O 0 0 0 0 0 0 0 0 0 0 0 0 -12.4878 1.5960 -0.5449 C 0 0 2 0 0 0 0 0 0 0 0 0 -11.8992 2.1485 0.7089 C 0 0 1 0 0 0 0 0 0 0 0 0 -11.5695 1.0561 1.6703 C 0 0 1 0 0 0 0 0 0 0 0 0 -12.6208 0.7738 2.5604 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.7840 2.9573 0.4181 O 0 0 0 0 0 0 0 0 0 0 0 0 -13.6713 2.2663 -0.8620 O 0 0 0 0 0 0 0 0 0 0 0 0 3.1887 0.2621 -1.9290 C 0 0 0 0 0 0 0 0 0 0 0 0 11.7343 1.2241 1.1250 C 0 0 1 0 0 0 0 0 0 0 0 0 12.6463 2.1935 0.4374 C 0 0 2 0 0 0 0 0 0 0 0 0 12.8795 1.6663 -0.9652 C 0 0 2 0 0 0 0 0 0 0 0 0 13.4408 2.7273 -1.6919 O 0 0 0 0 0 0 0 0 0 0 0 0 13.8628 2.1843 1.1199 O 0 0 0 0 0 0 0 0 0 0 0 0 11.5158 1.5599 2.4603 O 0 0 0 0 0 0 0 0 0 0 0 0 12.8164 -1.5270 -2.8324 H 0 0 0 0 0 0 0 0 0 0 0 0 11.7065 -0.9067 -0.8962 H 0 0 0 0 0 0 0 0 0 0 0 0 10.8593 -0.6604 -2.4991 H 0 0 0 0 0 0 0 0 0 0 0 0 11.5731 1.6194 -2.6338 H 0 0 0 0 0 0 0 0 0 0 0 0 9.6581 1.8488 0.8636 H 0 0 0 0 0 0 0 0 0 0 0 0 8.7574 0.2006 2.1095 H 0 0 0 0 0 0 0 0 0 0 0 0 7.9272 0.4105 0.5611 H 0 0 0 0 0 0 0 0 0 0 0 0 9.0525 -2.2641 1.5547 H 0 0 0 0 0 0 0 0 0 0 0 0 9.1539 -1.9685 -0.8766 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8882 -3.1640 -0.3266 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3288 -0.2871 -1.2563 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8889 -1.8289 -2.0395 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5661 -0.8093 2.1273 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9982 -2.4831 2.6126 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1931 -1.2143 1.7014 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8896 -2.4251 0.2083 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6927 -1.9619 -2.0973 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9601 -3.8444 0.2614 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4898 -4.0946 -1.4869 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7614 -4.0749 -1.0950 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4033 -0.8073 0.7701 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4976 1.4431 0.5527 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8339 0.5577 1.9722 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4043 1.4446 -1.2513 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5872 3.0434 0.1103 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1683 2.0685 1.4694 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1612 2.2087 2.0748 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4175 -0.6881 -0.0145 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2811 -0.1239 -2.9543 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6324 -1.4760 -2.2627 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3677 1.8955 -2.5434 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1220 2.1125 -2.6816 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2959 2.9716 -1.3735 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5889 -1.0372 -1.1567 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4439 -0.0744 -2.7294 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8878 1.7162 -1.5116 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6885 0.1129 -1.9558 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9243 -0.7696 0.2680 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5949 2.2170 1.0528 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1934 0.7624 1.9618 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3378 -1.5113 0.8554 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.6723 -2.6213 1.1784 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.2300 -1.4655 -1.1624 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.3869 -3.0924 -0.9123 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.8456 -2.7379 0.0364 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.5297 -1.5103 2.2491 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.2278 -0.2060 3.5535 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8539 0.0977 2.9306 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4148 -2.1328 2.8096 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.7894 1.8288 3.0445 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.1092 -1.0072 1.8257 H 0 0 0 0 0 0 0 0 0 0 0 0 -13.5153 0.0727 0.5232 H 0 0 0 0 0 0 0 0 0 0 0 0 -13.7480 -1.5184 -1.2944 H 0 0 0 0 0 0 0 0 0 0 0 0 -14.5076 0.1047 -1.7021 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.7542 -1.2422 -3.1676 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.8037 1.7511 -1.4043 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.6472 2.8184 1.1982 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.7545 1.4637 2.3403 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.5584 1.2620 3.3969 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.4551 2.6417 -0.4707 H 0 0 0 0 0 0 0 0 0 0 0 0 -13.8211 2.1333 -1.8366 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0805 -0.0675 -2.4561 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4354 0.5018 -2.7377 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4187 1.2281 -1.4624 H 0 0 0 0 0 0 0 0 0 0 0 0 12.2472 0.2339 1.1410 H 0 0 0 0 0 0 0 0 0 0 0 0 12.1593 3.1815 0.4366 H 0 0 0 0 0 0 0 0 0 0 0 0 13.6449 0.8588 -0.8625 H 0 0 0 0 0 0 0 0 0 0 0 0 14.2325 2.4310 -2.1843 H 0 0 0 0 0 0 0 0 0 0 0 0 13.6825 2.5955 2.0057 H 0 0 0 0 0 0 0 0 0 0 0 0 10.7218 2.1302 2.4971 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 1 12 13 1 0 11 14 1 0 14 15 1 0 15 16 1 0 16 17 1 0 17 18 1 0 16 19 1 0 19 20 1 0 20 21 1 0 20 22 1 0 22 23 1 0 23 24 1 0 24 25 2 0 25 26 1 0 26 27 1 0 27 28 1 0 28 29 1 0 29 30 2 0 26 31 1 6 26 32 1 0 32 33 1 0 33 34 1 0 34 35 1 0 34 36 1 0 36 37 1 0 37 38 1 0 38 39 1 0 39 40 1 0 39 41 1 0 41 42 1 0 42 43 1 0 43 44 1 0 42 45 1 0 41 46 1 0 46 47 1 0 47 48 1 0 48 49 1 0 49 50 1 0 50 51 1 0 49 52 1 0 52 53 1 0 53 54 1 0 54 55 1 0 53 56 1 0 52 57 1 0 19 58 1 6 5 59 1 0 59 60 1 0 60 61 1 0 61 62 1 0 60 63 1 0 59 64 1 0 61 3 1 0 13 8 1 0 21 15 1 0 27 22 1 0 43 37 1 0 54 47 1 0 17 11 1 0 29 19 1 0 35 25 1 0 1 65 1 0 2 66 1 0 2 67 1 0 3 68 1 6 5 69 1 1 7 70 1 0 7 71 1 0 8 72 1 1 9 73 1 0 9 74 1 0 10 75 1 0 10 76 1 0 13 77 1 0 13 78 1 0 15 79 1 1 16 80 1 1 17 81 1 6 18 82 1 0 18 83 1 0 18 84 1 0 20 85 1 1 21 86 1 0 21 87 1 0 22 88 1 6 23 89 1 0 23 90 1 0 24 91 1 0 27 92 1 1 28 93 1 0 28 94 1 0 31 95 1 0 31 96 1 0 31 97 1 0 32 98 1 0 32 99 1 0 33100 1 0 33101 1 0 34102 1 6 35103 1 0 35104 1 0 37105 1 1 39106 1 1 40107 1 0 40108 1 0 40109 1 0 41110 1 1 42111 1 1 43112 1 1 44113 1 0 45114 1 0 47115 1 1 49116 1 1 50117 1 0 50118 1 0 51119 1 0 52120 1 6 53121 1 1 54122 1 1 55123 1 0 56124 1 0 57125 1 0 58126 1 0 58127 1 0 58128 1 0 59129 1 1 60130 1 6 61131 1 1 62132 1 0 63133 1 0 64134 1 0 M END

Standard InCHIKey	LVSQNJFSNSFJQF-FAWHBWOFSA-N
Standard InCHI	InChI=1S/C45H70O19/c1-18-30-26(64-45(18)10-7-20(17-58-45)16-57-40-36(54)33(51)31(49)27(14-46)61-40)12-25-23-6-5-21-11-22(8-9-43(21,3)24(23)13-29(48)44(25,30)4)60-41-38(56)35(53)39(19(2)59-41)63-42-37(55)34(52)32(50)28(15-47)62-42/h5,18-20,22-28,30-42,46-47,49-56H,6-17H2,1-4H3/t18-,19+,20-,22-,23+,24-,25-,26-,27+,28+,30-,31+,32+,33-,34-,35+,36+,37+,38+,39-,40+,41-,42-,43-,44+,45+/m0/s1
SMILES	OC[C@H]1O[C@@H](OC[C@@H]2CC[C@@]3(OC2)O[C@@H]2[C@H]([C@@H]3C)[C@@]3([C@@H](C2)[C@@H]2CC=C4[C@]([C@H]2CC3=O)(C)CC[C@@H](C4)O[C@@H]2O[C@H](C)[C@@H]([C@@H]([C@H]2O)O)O[C@@H]2O[C@H](CO)[C@H]([C@@H]([C@H]2O)O)O)C)[C@@H]([C@H]([C@@H]1O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	914.45	Volume:	871.609 ? Van der Waals volume.
Dense:	1.049	LogP:	0.202 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	0.976 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.74 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	9.0	Rigid Bonds:	49.0
TPSA:	293.21 ? Topological Polar Surface Area.	H-Bond Acceptor:	19.0
H-Bond Donor:	10.0	Rings:	9.0
Heavy Atoms:	19.0

MedChem Properties

QED Drug-Likeness Score:	0.116	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	6.827	Fsp³:	0.933
MCE-18:	232.08 ? 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:	0.603	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.004 ? 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:	0.175	Promiscuous compounds:	0.157

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.804	MDCK Permeability:	-4.876
Pgp-inhibitor:	0.0	Pgp-substrate:	0.988
PAMPA:	1.0 ? 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):	0.0
20% Bioavailability (F20%):	0.0	30% Bioavailability (F30%):	0.468
50% Bioavailability (F50%):	0.941

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.002
Plasma Protein Binding (PPB):	43.075%	Volume Distribution (VD):	-0.486
Fu:	52.016% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.024
BSEP inhibitor:	0.063

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.006	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.438
HLM stability:	0.024 ? 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):

0.284

Half-life (T1/2):

3.379

ADMET: Toxicity

hERG Blockers:	0.002	hERG Blockers (10um):	0.006
Human Hepatotoxicity (H-HT):	0.609	Drug-induced Liver Injury (DILI):	0.99
AMES Toxicity:	0.979	Rat Oral Acute Toxicity:	0.005
Maximum Recommended Daily Dose:	0.003	Skin Sensitization:	1.0
Carcinogencity:	0.212	Eye Corrosion:	0.0
Eye Irritation:	0.0	Respiratory Toxicity:	0.0
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	1.0
Hematotoxicity:	0.639	Drug-induced Nephrotoxicity:	0.997
Genotoxicity:	0.731	RPMI-8226 Immunitoxicity:	0.42
A549 Cytotoxicity:	0.839	Hek293 Cytotoxicity:	0.792
BCF:	1.142 ? 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:	3.345 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.607 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.803 ? 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	=	5.06	ug.mL-1	PMID[15620239]

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 NPC182900 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	21369
0.1-0.2	24550
0.2-0.3	3307
0.3-0.4	457
0.4-0.5	118
0.5-0.6	46
0.6-0.7	8
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.914	High Similarity	NPC249553
0.75	Intermediate Similarity	NPC161738
0.7282	Intermediate Similarity	NPC6806
0.678	Remote Similarity	NPC305771
0.678	Remote Similarity	NPC94072
0.678	Remote Similarity	NPC169816
0.6531	Remote Similarity	NPC181845
0.6525	Remote Similarity	NPC15918
0.6132	Remote Similarity	NPC470432
0.6132	Remote Similarity	NPC230507
0.6091	Remote Similarity	NPC477809
0.5983	Remote Similarity	NPC477811
0.5965	Remote Similarity	NPC269297
0.5965	Remote Similarity	NPC222202
0.5826	Remote Similarity	NPC475550
0.5752	Remote Similarity	NPC300557
0.5702	Remote Similarity	NPC480555
0.5702	Remote Similarity	NPC150372
0.5664	Remote Similarity	NPC92890
0.5586	Remote Similarity	NPC113044
0.5586	Remote Similarity	NPC283829
0.5586	Remote Similarity	NPC14704
0.5586	Remote Similarity	NPC161676
0.5583	Remote Similarity	NPC233433
0.5575	Remote Similarity	NPC602423
0.5565	Remote Similarity	NPC224314
0.552	Remote Similarity	NPC477808
0.5508	Remote Similarity	NPC309278
0.547	Remote Similarity	NPC475319
0.5462	Remote Similarity	NPC194207
0.5462	Remote Similarity	NPC22779
0.5439	Remote Similarity	NPC470433
0.5439	Remote Similarity	NPC46190
0.5439	Remote Similarity	NPC171073
0.5391	Remote Similarity	NPC248746
0.5378	Remote Similarity	NPC475333
0.5378	Remote Similarity	NPC224098
0.5378	Remote Similarity	NPC208383
0.5351	Remote Similarity	NPC202898
0.5328	Remote Similarity	NPC480553
0.5276	Remote Similarity	NPC220836
0.525	Remote Similarity	NPC32361
0.5246	Remote Similarity	NPC23808
0.5246	Remote Similarity	NPC87998
0.5242	Remote Similarity	NPC232054
0.5197	Remote Similarity	NPC477807
0.5164	Remote Similarity	NPC108072
0.5164	Remote Similarity	NPC480554
0.5161	Remote Similarity	NPC31896
0.5135	Remote Similarity	NPC107188
0.5118	Remote Similarity	NPC480556
0.5093	Remote Similarity	NPC325828
0.5085	Remote Similarity	NPC42171
0.5082	Remote Similarity	NPC63609
0.5044	Remote Similarity	NPC215408
0.5039	Remote Similarity	NPC94086
0.5039	Remote Similarity	NPC473817

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC182900 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7114
0.1-0.2	1950
0.2-0.3	79
0.3-0.4	4
0.4-0.5	1
0.5-0.6	1
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
0.5093	Remote Similarity	NPD8171	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