NPASS Compound

Natural Product: NPC474265

Natural Product ID	NPC474265
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Bryonioside B
IUPAC Name	(3S,8S,9R,10R,13R,14S,17R)-3-[(2R,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-17-[(2R,5R)-5,6-dihydroxy-6-methylheptan-2-yl]-4,4,9,13,14-pentamethyl-1,2,3,7,8,10,12,15,16,17-decahydrocyclopenta[a]phenanthren-11-one
Synonyms	bryonioside B
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL464459
PubChem CID	10865639
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 [CHEMONTID:0001687] Cucurbitacin glycosides

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 125130 0 0 0 0 0 0 0 0999 V2000 -9.6775 -3.5580 0.1325 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.9161 -2.3482 0.6424 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.2527 -2.7365 1.9357 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7753 -2.8971 1.8012 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1315 -1.7140 1.1118 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.0767 -1.0698 0.1194 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.0187 -1.9701 -0.3528 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.3774 -0.4013 -0.8777 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.5596 0.9743 -0.8015 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.2975 1.5506 -1.9959 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8274 2.9642 -2.2146 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4187 3.7039 -0.9957 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6833 2.9815 -0.0607 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.3113 1.7690 -0.6467 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2368 1.1431 -0.1006 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0904 1.1812 -0.9143 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6953 -0.1281 -1.4419 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4988 -0.8602 -0.9827 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4177 -0.0988 -0.2529 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6767 1.3231 -0.5204 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1946 2.0736 -1.0758 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5295 1.6690 -1.5183 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8307 0.2101 -1.4103 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9751 -0.5853 -0.4942 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6483 -0.8067 0.8282 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9378 -0.9046 1.8022 O 0 0 0 0 0 0 0 0 0 0 0 0 3.1204 -0.9120 1.0063 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8964 -0.0368 0.1087 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2817 -0.0314 -1.2649 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1511 0.9844 -1.9573 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5378 0.5661 -1.4497 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2738 -0.3431 -0.2669 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4058 -0.1299 0.7129 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3352 -0.9603 1.9291 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6434 -0.3843 -0.0765 C 0 0 0 0 0 0 0 0 0 0 0 0 8.9732 -0.2571 0.4991 C 0 0 0 0 0 0 0 0 0 0 0 0 9.4367 -1.1472 1.5997 C 0 0 0 0 0 0 0 0 0 0 0 0 10.8815 -0.7812 2.0018 C 0 0 0 0 0 0 0 0 0 0 0 0 11.2904 -1.6202 3.1890 C 0 0 0 0 0 0 0 0 0 0 0 0 11.8313 -1.0627 0.8726 C 0 0 0 0 0 0 0 0 0 0 0 0 10.9233 0.5567 2.3777 O 0 0 0 0 0 0 0 0 0 0 0 0 9.4192 -2.4968 1.2456 O 0 0 0 0 0 0 0 0 0 0 0 0 3.6405 -1.3435 -1.9389 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9005 1.3387 0.7717 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7873 -2.0424 -0.9724 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0099 1.8294 -0.1139 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1350 3.3355 -0.2643 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2874 1.5388 1.3525 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.5914 4.3757 -0.3091 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.3477 5.1124 -1.1960 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.9560 3.6424 -2.7471 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.0706 0.8244 -3.1565 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0343 -2.2048 0.4111 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.2354 -2.9509 3.1052 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.8621 -3.8829 2.4569 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.1661 -4.0539 1.0227 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.4314 -3.3280 -0.6275 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.9464 -4.3046 -0.2503 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.5957 -1.4791 0.7828 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.4898 -1.9238 2.6827 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5464 -3.8667 1.3291 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8459 -0.9836 1.8676 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.6317 -0.2941 0.7098 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2343 1.2155 0.0779 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.3994 1.5058 -1.8133 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0803 3.0447 -3.0608 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7442 4.5330 -1.3327 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9676 2.0917 -1.6826 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3188 1.8335 -1.8084 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5469 0.0074 -2.5780 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5847 -0.8532 -1.4592 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9748 -1.3294 -1.8675 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8753 -1.7226 -0.3693 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5873 -0.2940 0.8806 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0246 3.1532 -1.2667 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2203 2.3250 -0.9014 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6652 2.0664 -2.5497 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5829 -0.1993 -2.4463 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2410 -0.5576 2.0839 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4042 -1.9738 0.9962 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0651 0.8122 -3.0540 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9707 2.0207 -1.7790 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0723 1.4983 -1.1540 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0814 0.0510 -2.2866 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4494 -1.3784 -0.6432 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4721 0.9845 0.9716 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3251 -1.3202 2.2328 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8868 -1.9056 1.7342 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6778 -0.3929 2.8173 H 0 0 0 0 0 0 0 0 0 0 0 0 7.5335 -1.4736 -0.4281 H 0 0 0 0 0 0 0 0 0 0 0 0 7.6042 0.1533 -1.0795 H 0 0 0 0 0 0 0 0 0 0 0 0 9.7110 -0.4767 -0.3594 H 0 0 0 0 0 0 0 0 0 0 0 0 9.2639 0.8263 0.7162 H 0 0 0 0 0 0 0 0 0 0 0 0 8.8603 -1.0023 2.5056 H 0 0 0 0 0 0 0 0 0 0 0 0 10.4616 -1.7785 3.9118 H 0 0 0 0 0 0 0 0 0 0 0 0 12.1601 -1.1801 3.7208 H 0 0 0 0 0 0 0 0 0 0 0 0 11.6371 -2.6189 2.8376 H 0 0 0 0 0 0 0 0 0 0 0 0 12.2697 -0.1425 0.4369 H 0 0 0 0 0 0 0 0 0 0 0 0 12.6842 -1.6645 1.2423 H 0 0 0 0 0 0 0 0 0 0 0 0 11.3358 -1.6844 0.0756 H 0 0 0 0 0 0 0 0 0 0 0 0 11.0202 0.6345 3.3613 H 0 0 0 0 0 0 0 0 0 0 0 0 9.1841 -2.6405 0.2973 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9271 -1.4935 -2.7837 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7456 -2.1932 -1.2764 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6347 -1.2915 -2.4831 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5777 1.1927 1.6723 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3669 2.1197 0.1882 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9263 1.5845 1.2463 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1057 -2.5123 -0.5103 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7847 -2.0633 -2.0562 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6028 -2.7067 -0.5467 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4188 3.6290 -1.2757 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2711 3.8551 0.1706 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0046 3.6317 0.3911 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5020 1.9158 2.0175 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5204 0.4678 1.5189 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2249 2.1003 1.6087 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.2179 3.5898 0.1857 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2475 5.0516 0.5058 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.3300 5.0833 -1.0073 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.2014 3.1392 -3.5818 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5694 -0.0121 -2.9924 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2052 -3.0766 0.0002 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6060 -2.2168 3.6767 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.3655 -4.7103 2.1836 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 6 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 2 0 21 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 25 26 2 0 25 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 33 34 1 0 33 35 1 0 35 36 1 0 36 37 1 0 37 38 1 0 38 39 1 0 38 40 1 0 38 41 1 0 37 42 1 0 29 43 1 0 28 44 1 0 24 45 1 0 20 46 1 0 46 47 1 0 46 48 1 0 12 49 1 0 49 50 1 0 11 51 1 0 10 52 1 0 5 53 1 0 4 54 1 0 3 55 1 0 7 2 1 0 14 9 1 0 46 16 1 0 24 19 1 0 29 23 1 0 32 28 1 0 1 56 1 0 1 57 1 0 1 58 1 0 2 59 1 0 3 60 1 0 4 61 1 0 5 62 1 0 6 63 1 0 9 64 1 0 10 65 1 0 11 66 1 0 12 67 1 0 14 68 1 0 16 69 1 0 17 70 1 0 17 71 1 0 18 72 1 0 18 73 1 0 19 74 1 0 21 75 1 0 22 76 1 0 22 77 1 0 23 78 1 0 27 79 1 0 27 80 1 0 30 81 1 0 30 82 1 0 31 83 1 0 31 84 1 0 32 85 1 0 33 86 1 0 34 87 1 0 34 88 1 0 34 89 1 0 35 90 1 0 35 91 1 0 36 92 1 0 36 93 1 0 37 94 1 0 39 95 1 0 39 96 1 0 39 97 1 0 40 98 1 0 40 99 1 0 40100 1 0 41101 1 0 42102 1 0 43103 1 0 43104 1 0 43105 1 0 44106 1 0 44107 1 0 44108 1 0 45109 1 0 45110 1 0 45111 1 0 47112 1 0 47113 1 0 47114 1 0 48115 1 0 48116 1 0 48117 1 0 49118 1 0 49119 1 0 50120 1 0 51121 1 0 52122 1 0 53123 1 0 54124 1 0 55125 1 0 M END

Standard InCHIKey	BQYXEGPEDSNOPN-UEOQDMPUSA-N
Standard InCHI	InChI=1S/C42H70O13/c1-20(10-14-27(44)39(5,6)51)22-16-17-40(7)26-13-11-23-24(42(26,9)28(45)18-41(22,40)8)12-15-29(38(23,3)4)54-37-35(33(49)31(47)25(19-43)53-37)55-36-34(50)32(48)30(46)21(2)52-36/h11,20-22,24-27,29-37,43-44,46-51H,10,12-19H2,1-9H3/t20-,21+,22-,24-,25-,26+,27-,29+,30+,31-,32-,33+,34-,35-,36+,37+,40+,41-,42+/m1/s1
SMILES	CC1C(C(C(C(O1)OC2C(C(C(OC2OC3CCC4C(=CCC5C4(C(=O)CC6(C5(CCC6C(C)CCC(C(C)(C)O)O)C)C)C)C3(C)C)CO)O)O)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	782.48	Volume:	792.649 ? Van der Waals volume.
Dense:	0.987	LogP:	2.045 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.908 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.779 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	10.0	Rigid Bonds:	33.0
TPSA:	215.83 ? Topological Polar Surface Area.	H-Bond Acceptor:	13.0
H-Bond Donor:	8.0	Rings:	6.0
Heavy Atoms:	13.0

MedChem Properties

QED Drug-Likeness Score:	0.15	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.951	Fsp³:	0.929
MCE-18:	132.222 ? 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:	0.066	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.008 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.197 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.166	Promiscuous compounds:	0.002

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.991	MDCK Permeability:	-5.085
Pgp-inhibitor:	0.0	Pgp-substrate:	0.919
PAMPA:	0.998 ? 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):	0.088
20% Bioavailability (F20%):	0.002	30% Bioavailability (F30%):	0.366
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.303	MRP1:	1.0
Plasma Protein Binding (PPB):	65.826%	Volume Distribution (VD):	-0.372
Fu:	24.419% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.0
OATP1B3 inhibitor:	0.921	BCRP inhibitor:	0.025
BSEP inhibitor:	0.349

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.999	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.489	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.001
CYP3A4-inhibitor:	0.993	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.002	CYP2C8-inhibitor:	0.99
HLM stability:	0.004 ? 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):

1.079

Half-life (T1/2):

2.91

ADMET: Toxicity

hERG Blockers:	0.047	hERG Blockers (10um):	0.337
Human Hepatotoxicity (H-HT):	0.578	Drug-induced Liver Injury (DILI):	0.205
AMES Toxicity:	0.27	Rat Oral Acute Toxicity:	0.147
Maximum Recommended Daily Dose:	0.505	Skin Sensitization:	0.135
Carcinogencity:	0.067	Eye Corrosion:	0.0
Eye Irritation:	0.0	Respiratory Toxicity:	0.019
Drug-induced Neurotoxicity:	0.491	Ototoxicity:	0.998
Hematotoxicity:	0.046	Drug-induced Nephrotoxicity:	0.08
Genotoxicity:	0.092	RPMI-8226 Immunitoxicity:	0.089
A549 Cytotoxicity:	0.109	Hek293 Cytotoxicity:	0.69
BCF:	0.894 ? 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:	3.85 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.71 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.24 ? 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
NPO33132	bryonia dioica	Species	Cucurbitaceae	Eukaryota	Roots	n.a.	n.a.	PMID[11858752]
NPO33132	bryonia dioica	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17503850]

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
Inhibition	4
Activity	2
ID50	1

Activity Type	# Activity
Cell line	1
Organism	2
Others	4

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
NPT80	Cell line	Raji	Homo sapiens	Activity	=	60.0	%	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Inhibition	=	0.0	%	PMID[22037378]
NPT2	Others	Unspecified	n.a.	Inhibition	=	29.9	%	PMID[25729554]
NPT2	Others	Unspecified	n.a.	Inhibition	=	72.7	%	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Inhibition	=	97.4	%	DOI[10.6019/CHEMBL1201861]

In vivo activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT32	Organism	Mus musculus	Mus musculus	ID50	=	0.2	mg	PMID[2853205]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	94.0	%	PMID[2853205]

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 NPC474265 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	21580
0.1-0.2	23298
0.2-0.3	3846
0.3-0.4	1021
0.4-0.5	86
0.5-0.6	16
0.6-0.7	5
0.7-0.8	0
0.8-0.85	3
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8736	High Similarity	NPC474557
0.8193	Intermediate Similarity	NPC154856
0.8132	Intermediate Similarity	NPC473882
0.8068	Intermediate Similarity	NPC485578
0.7396	Intermediate Similarity	NPC485579
0.7079	Intermediate Similarity	NPC130427
0.6889	Remote Similarity	NPC74727
0.6771	Remote Similarity	NPC279638
0.6735	Remote Similarity	NPC168899
0.6735	Remote Similarity	NPC69273
0.6731	Remote Similarity	NPC485580
0.5909	Remote Similarity	NPC241008
0.5865	Remote Similarity	NPC302057
0.5686	Remote Similarity	NPC210420
0.5625	Remote Similarity	NPC34562
0.5625	Remote Similarity	NPC52241
0.5521	Remote Similarity	NPC221562
0.5472	Remote Similarity	NPC293623
0.5392	Remote Similarity	NPC309448
0.534	Remote Similarity	NPC485581
0.5306	Remote Similarity	NPC187400
0.5288	Remote Similarity	NPC190395
0.5258	Remote Similarity	NPC75608
0.5227	Remote Similarity	NPC32830
0.5179	Remote Similarity	NPC162574
0.51	Remote Similarity	NPC475317
0.5045	Remote Similarity	NPC485582

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC474265 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7274
0.1-0.2	1812
0.2-0.3	58
0.3-0.4	6
0.4-0.5	0
0.5-0.6	0
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
		NPD

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