NPASS Compound

Natural Product: NPC594468

Natural Product ID	NPC594468
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Uralsaponin A
IUPAC Name	(2~{S},3~{S},4~{S},5~{R},6~{R})-6-[(2~{R},3~{R},4~{S},5~{S},6~{S})-2-[[(3~{S},4~{a}~{R},6~{a}~{R},6~{b}~{S},8~{a}~{S},11~{S},12~{a}~{R},14~{a}~{R},14~{b}~{S})-11-carboxy-4,4,6~{a},6~{b},8~{a},11,14~{b}-heptamethyl-14-oxo-2,3,4~{a},5,6,7,8,9,10,12,12~{a},14~{a}-dodecahydro-1~{H}-picen-3-yl]oxy]-6-carboxy-4,5-dihydroxy-tetrahydropyran-3-yl]oxy-3,4,5-trihydroxy-tetrahydropyran-2-carboxylic acid
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	n.a.
Chemical Classification	CHEMONTID:0000000 [Organic compounds]

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 120126 0 0 0 0 0 0 0 0999 V2000 2.3309 0.1858 -1.2184 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6772 -0.3160 0.0412 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1212 -1.7799 0.2079 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1761 0.4094 1.2289 C 0 0 1 0 0 0 0 0 0 0 0 0 3.4735 0.9209 1.0239 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3875 0.4327 1.9036 C 0 0 2 0 0 0 0 0 0 0 0 0 4.8663 1.3976 2.8290 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1146 0.7666 4.0113 C 0 0 2 0 0 0 0 0 0 0 0 0 5.9897 1.5990 4.8880 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3668 2.7123 4.4850 O 0 0 0 0 0 0 0 0 0 0 0 0 6.3718 1.1262 6.1364 O 0 0 0 0 0 0 0 0 0 0 0 0 5.6165 -0.6107 3.8554 C 0 0 1 0 0 0 0 0 0 0 0 0 4.6843 -1.5747 4.2810 O 0 0 0 0 0 0 0 0 0 0 0 0 6.1881 -1.0170 2.5431 C 0 0 2 0 0 0 0 0 0 0 0 0 7.5757 -0.8695 2.5490 O 0 0 0 0 0 0 0 0 0 0 0 0 5.6125 -0.2111 1.3611 C 0 0 1 0 0 0 0 0 0 0 0 0 5.4817 -0.9412 0.2196 O 0 0 0 0 0 0 0 0 0 0 0 0 6.3599 -0.5013 -0.7648 C 0 0 2 0 0 0 0 0 0 0 0 0 5.7278 -0.0036 -1.9007 O 0 0 0 0 0 0 0 0 0 0 0 0 6.6663 0.7641 -2.5895 C 0 0 2 0 0 0 0 0 0 0 0 0 6.0831 1.4336 -3.7667 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8881 1.3482 -4.1331 O 0 0 0 0 0 0 0 0 0 0 0 0 6.9135 2.2289 -4.5458 O 0 0 0 0 0 0 0 0 0 0 0 0 7.9311 0.0058 -2.9018 C 0 0 1 0 0 0 0 0 0 0 0 0 8.9694 0.3179 -2.0027 O 0 0 0 0 0 0 0 0 0 0 0 0 7.6367 -1.4730 -2.6854 C 0 0 2 0 0 0 0 0 0 0 0 0 6.6299 -1.8832 -3.5368 O 0 0 0 0 0 0 0 0 0 0 0 0 7.2685 -1.6290 -1.2217 C 0 0 1 0 0 0 0 0 0 0 0 0 8.4654 -1.6353 -0.5063 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3607 1.5839 1.6854 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0857 1.2604 1.6289 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5680 0.8589 0.2267 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.3270 1.9834 -0.7040 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0254 0.5032 0.3688 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.9331 1.6419 0.5653 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6231 2.7307 1.1407 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3046 1.4829 0.0452 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8235 0.3297 -0.3285 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2383 0.2586 -0.8500 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.9814 1.3164 -0.1090 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.4610 1.2105 -0.0515 C 0 0 1 0 0 0 0 0 0 0 0 0 -8.8961 2.1347 1.1088 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.1446 1.7964 -1.2416 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.8848 1.0393 -1.9122 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.9795 3.1217 -1.6049 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.9017 -0.1863 0.2073 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7877 -1.1669 0.3436 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8196 -1.1014 -0.8334 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.6874 -1.3145 -2.0882 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8968 -2.2552 -0.7426 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4596 -1.9858 -1.0329 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9393 -0.8573 -0.2098 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.8329 -1.3474 1.2178 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5714 -0.3664 -0.7130 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.8222 0.3711 -2.0057 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6888 -1.5481 -1.0386 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2822 -0.9982 -1.3474 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1796 -0.3962 -0.0751 C 0 0 1 0 0 0 0 0 0 0 0 0 2.8918 1.1494 -1.0697 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6143 0.2718 -2.0820 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0867 -0.5434 -1.5738 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2744 -2.4131 0.5890 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4289 -2.2176 -0.7515 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9890 -1.8106 0.8717 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1819 -0.3106 2.1000 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8380 -0.3264 2.5394 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0987 0.6858 4.5266 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5129 1.8167 6.8698 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4651 -0.7264 4.6050 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9870 -2.4509 3.9833 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9413 -2.1091 2.3890 H 0 0 0 0 0 0 0 0 0 0 0 0 7.9023 -1.0401 3.4597 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3971 0.5857 1.1493 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9994 0.3533 -0.4070 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9724 1.5860 -1.8779 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5518 2.9222 -5.1962 H 0 0 0 0 0 0 0 0 0 0 0 0 8.3145 0.2074 -3.9161 H 0 0 0 0 0 0 0 0 0 0 0 0 8.9701 1.2911 -1.8013 H 0 0 0 0 0 0 0 0 0 0 0 0 8.5761 -2.0546 -2.8350 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8749 -2.7730 -3.8825 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7206 -2.6035 -1.1203 H 0 0 0 0 0 0 0 0 0 0 0 0 9.0575 -2.3407 -0.8616 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6960 2.4749 1.1497 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6073 1.7523 2.7627 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7213 1.9814 2.1268 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2130 0.3004 2.2200 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3065 1.6961 -1.7751 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1521 2.7511 -0.6485 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5985 2.5680 -0.5296 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0742 -0.0756 1.3393 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8890 2.4067 -0.0150 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2320 0.5863 -1.9398 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7749 2.3054 -0.6309 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6162 1.3963 0.9611 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.5616 3.1590 0.7731 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.3213 1.8193 1.9822 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.9805 2.1012 1.1962 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.2659 3.3803 -2.5595 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.6692 -0.5095 -0.5432 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.4588 -0.2006 1.1830 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.2194 -2.1831 0.4479 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1981 -0.8962 1.2412 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2025 -2.0783 -2.7669 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.6713 -0.3825 -2.6817 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.6725 -1.7102 -1.8526 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2047 -3.0576 -1.4877 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0432 -2.7859 0.2337 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8916 -2.9102 -0.7233 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2893 -1.8887 -2.1175 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9502 -0.5362 1.9647 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8830 -1.9303 1.3731 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6247 -2.0820 1.4738 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8864 0.2341 -2.3602 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6894 1.4520 -1.9372 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2200 -0.0489 -2.8600 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1095 -2.0549 -1.9216 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5593 -2.1969 -0.1534 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3165 -0.2943 -2.1881 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2990 -1.8777 -1.6766 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1285 -1.1181 0.7462 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 2 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 2 0 9 11 1 0 8 12 1 0 12 13 1 0 12 14 1 0 14 15 1 0 14 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 2 0 21 23 1 0 20 24 1 0 24 25 1 0 24 26 1 0 26 27 1 0 26 28 1 0 28 29 1 0 4 30 1 0 30 31 1 0 31 32 1 0 32 33 1 6 32 34 1 0 34 35 1 0 35 36 2 0 35 37 1 0 37 38 2 0 38 39 1 0 39 40 1 0 40 41 1 0 41 42 1 1 41 43 1 0 43 44 2 0 43 45 1 0 41 46 1 0 46 47 1 0 47 48 1 0 48 49 1 6 48 50 1 0 50 51 1 0 51 52 1 0 52 53 1 1 52 54 1 0 54 55 1 6 54 56 1 0 56 57 1 0 57 58 1 0 58 2 1 0 16 6 1 0 28 18 1 0 58 32 1 0 54 34 1 0 52 38 1 0 48 39 1 0 1 59 1 0 1 60 1 0 1 61 1 0 3 62 1 0 3 63 1 0 3 64 1 0 4 65 1 1 6 66 1 1 8 67 1 1 11 68 1 0 12 69 1 1 13 70 1 0 14 71 1 6 15 72 1 0 16 73 1 6 18 74 1 1 20 75 1 1 23 76 1 0 24 77 1 6 25 78 1 0 26 79 1 6 27 80 1 0 28 81 1 6 29 82 1 0 30 83 1 0 30 84 1 0 31 85 1 0 31 86 1 0 33 87 1 0 33 88 1 0 33 89 1 0 34 90 1 1 37 91 1 0 39 92 1 6 40 93 1 0 40 94 1 0 42 95 1 0 42 96 1 0 42 97 1 0 45 98 1 0 46 99 1 0 46100 1 0 47101 1 0 47102 1 0 49103 1 0 49104 1 0 49105 1 0 50106 1 0 50107 1 0 51108 1 0 51109 1 0 53110 1 0 53111 1 0 53112 1 0 55113 1 0 55114 1 0 55115 1 0 56116 1 0 56117 1 0 57118 1 0 57119 1 0 58120 1 1 M END

Standard InCHIKey	LPLVUJXQOOQHMX-MOGLOQIBSA-N
Standard InCHI	InChI=1S/C42H62O16/c1-37(2)21-8-11-42(7)31(20(43)16-18-19-17-39(4,36(53)54)13-12-38(19,3)14-15-41(18,42)6)40(21,5)10-9-22(37)55-35-30(26(47)25(46)29(57-35)33(51)52)58-34-27(48)23(44)24(45)28(56-34)32(49)50/h16,19,21-31,34-35,44-48H,8-15,17H2,1-7H3,(H,49,50)(H,51,52)(H,53,54)/t19-,21-,22-,23-,24-,25-,26-,27+,28-,29-,30+,31+,34-,35+,38+,39-,40-,41+,42+/m0/s1
SMILES	CC1(C)[C@@H](O[C@@H]2O[C@H](C(=O)O)[C@@H](O)[C@H](O)[C@H]2O[C@@H]2O[C@H](C(=O)O)[C@@H](O)[C@H](O)[C@H]2O)CC[C@]2(C)[C@H]3C(=O)C=C4[C@@H]5C[C@@](C)(C(=O)O)CC[C@]5(C)CC[C@@]4(C)[C@]3(C)CC[C@@H]12

Calculated Properties

Physi-Chem Properties

Molecular Weight:	822.4	Volume:	802.554 ? Van der Waals volume.
Dense:	1.025	LogP:	1.455 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.929 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.838 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	7.0	Rigid Bonds:	42.0
TPSA:	267.04 ? Topological Polar Surface Area.	H-Bond Acceptor:	16.0
H-Bond Donor:	8.0	Rings:	7.0
Heavy Atoms:	16.0

MedChem Properties

QED Drug-Likeness Score:	0.171	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.929	Fsp³:	0.857
MCE-18:	159.128 ? 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:	0.796	Fluc inhibitor:	0.005 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.114 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.001 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.167	Promiscuous compounds:	0.272

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.071	MDCK Permeability:	-5.09
Pgp-inhibitor:	0.0	Pgp-substrate:	0.122
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%):	0.059	30% Bioavailability (F30%):	0.001
50% Bioavailability (F50%):	0.573

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.999
Plasma Protein Binding (PPB):	67.183%	Volume Distribution (VD):	-0.562
Fu:	25.697% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.01
OATP1B3 inhibitor:	0.0	BCRP inhibitor:	0.0
BSEP inhibitor:	0.0

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:	0.997	CYP3A4-substrate:	0.001
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.001
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):

0.292

Half-life (T1/2):

3.971

ADMET: Toxicity

hERG Blockers:	0.002	hERG Blockers (10um):	0.001
Human Hepatotoxicity (H-HT):	0.583	Drug-induced Liver Injury (DILI):	0.958
AMES Toxicity:	0.095	Rat Oral Acute Toxicity:	0.035
Maximum Recommended Daily Dose:	0.022	Skin Sensitization:	0.999
Carcinogencity:	0.047	Eye Corrosion:	0.0
Eye Irritation:	0.041	Respiratory Toxicity:	0.03
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	0.974
Hematotoxicity:	0.257	Drug-induced Nephrotoxicity:	0.998
Genotoxicity:	0.97	RPMI-8226 Immunitoxicity:	0.042
A549 Cytotoxicity:	0.003	Hek293 Cytotoxicity:	0.009
BCF:	0.427 ? 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:	3.499 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.224 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.276 ? 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
NPO2865	Abrus precatorius	Species	Fabaceae	Eukaryota	aerial parts	n.a.	n.a.	PMID[19299148]
NPO2865	Abrus precatorius	Species	Fabaceae	Eukaryota	n.a.	leaf	n.a.	PMID[22210168]
NPO2865	Abrus precatorius	Species	Fabaceae	Eukaryota	n.a.	stem	n.a.	PMID[22210168]
NPO2865	Abrus precatorius	Species	Fabaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[2691636]
NPO2865	Abrus precatorius	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[2691636]
NPO2865	Abrus precatorius	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2865	Abrus precatorius	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2865	Abrus precatorius	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2865	Abrus precatorius	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO2865	Abrus precatorius	Species	Fabaceae	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

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

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 NPC594468 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	20511
0.1-0.2	25636
0.2-0.3	3036
0.3-0.4	516
0.4-0.5	103
0.5-0.6	7
0.6-0.7	13
0.7-0.8	0
0.8-0.85	7
0.85-0.9	4
0.9-0.95	4
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC482747
1.0	High Similarity	NPC202666
1.0	High Similarity	NPC471961
1.0	High Similarity	NPC242015
0.9	High Similarity	NPC482741
0.9	High Similarity	NPC482745
0.9	High Similarity	NPC482743
0.9	High Similarity	NPC146753
0.8901	High Similarity	NPC471965
0.8901	High Similarity	NPC482749
0.8837	High Similarity	NPC482752
0.8526	High Similarity	NPC262199
0.8404	Intermediate Similarity	NPC14617
0.8152	Intermediate Similarity	NPC482750
0.8085	Intermediate Similarity	NPC482746
0.8041	Intermediate Similarity	NPC482734
0.8041	Intermediate Similarity	NPC182342
0.8041	Intermediate Similarity	NPC482727
0.8041	Intermediate Similarity	NPC471964
0.7957	Intermediate Similarity	NPC309780
0.7526	Intermediate Similarity	NPC482717
0.7374	Intermediate Similarity	NPC285091
0.7353	Intermediate Similarity	NPC247315
0.7353	Intermediate Similarity	NPC482728
0.7255	Intermediate Similarity	NPC482755
0.7228	Intermediate Similarity	NPC482722
0.7228	Intermediate Similarity	NPC471963
0.7228	Intermediate Similarity	NPC482729
0.7228	Intermediate Similarity	NPC482742
0.7228	Intermediate Similarity	NPC482744
0.7204	Intermediate Similarity	NPC471967
0.7143	Intermediate Similarity	NPC482748
0.7115	Intermediate Similarity	NPC482737
0.7115	Intermediate Similarity	NPC482735
0.701	Intermediate Similarity	NPC482726
0.7009	Intermediate Similarity	NPC471962
0.6667	Remote Similarity	NPC482739
0.6607	Remote Similarity	NPC482736
0.6607	Remote Similarity	NPC482738
0.6569	Remote Similarity	NPC482751
0.6389	Remote Similarity	NPC482740
0.6222	Remote Similarity	NPC482712
0.6222	Remote Similarity	NPC74751
0.6154	Remote Similarity	NPC275343
0.6	Remote Similarity	NPC4036
0.6	Remote Similarity	NPC65120
0.6	Remote Similarity	NPC145067
0.6	Remote Similarity	NPC233455
0.6	Remote Similarity	NPC158030
0.5364	Remote Similarity	NPC472949
0.5326	Remote Similarity	NPC96095
0.5192	Remote Similarity	NPC286347
0.5175	Remote Similarity	NPC251768
0.5093	Remote Similarity	NPC480938
0.5085	Remote Similarity	NPC301449
0.5085	Remote Similarity	NPC601290

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC594468 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6404
0.1-0.2	2700
0.2-0.3	38
0.3-0.4	1
0.4-0.5	3
0.5-0.6	1
0.6-0.7	2
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
1.0	High Similarity	NPD8328	Phase 2
0.6222	Remote Similarity	NPD7748	Pre-clinical
0.6	Remote Similarity	NPD7515	Phase 2
0.5895	Remote Similarity	NPD7902	Phase 4

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