NPASS Compound

Natural Product: NPC193893

Natural Product ID	NPC193893
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Gitoxin
IUPAC Name	3-[(3S,5R,8R,9S,10S,13R,14S,16S,17R)-3-[(2R,4S,5S,6R)-5-[(2S,4S,5S,6R)-5-[(2S,4S,5S,6R)-4,5-dihydroxy-6-methyloxan-2-yl]oxy-4-hydroxy-6-methyloxan-2-yl]oxy-4-hydroxy-6-methyloxan-2-yl]oxy-14,16-dihydroxy-10,13-dimethyl-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl]-2H-furan-5-one
Synonyms	Gitoxin
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL109317
PubChem CID	91540
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001125] Steroid lactones [CHEMONTID:0001555] Cardenolides and derivatives [CHEMONTID:0001559] Cardenolide glycosides and derivatives

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 119126 0 0 0 0 0 0 0 0999 V2000 14.5388 -1.5751 -0.0743 O 0 0 0 0 0 0 0 0 0 0 0 0 13.3960 -1.3155 0.3831 C 0 0 0 0 0 0 0 0 0 0 0 0 12.8420 -1.7777 1.5563 O 0 0 0 0 0 0 0 0 0 0 0 0 11.5670 -1.2532 1.6820 C 0 0 0 0 0 0 0 0 0 0 0 0 11.3603 -0.4096 0.4790 C 0 0 0 0 0 0 0 0 0 0 0 0 12.4400 -0.4540 -0.2768 C 0 0 0 0 0 0 0 0 0 0 0 0 10.1094 0.3387 0.2702 C 0 0 1 0 0 0 0 0 0 0 0 0 10.0928 1.3207 -0.8451 C 0 0 1 0 0 0 0 0 0 0 0 0 10.5574 0.8719 -2.0637 O 0 0 0 0 0 0 0 0 0 0 0 0 8.5675 1.5747 -0.9506 C 0 0 0 0 0 0 0 0 0 0 0 0 8.0951 0.1454 -0.9544 C 0 0 1 0 0 0 0 0 0 0 0 0 8.8658 -0.5166 0.1605 C 0 0 1 0 0 0 0 0 0 0 0 0 9.1375 -1.9337 -0.2588 C 0 0 0 0 0 0 0 0 0 0 0 0 8.1798 -0.5295 1.4838 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7874 -1.1300 1.2926 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0536 -0.1080 0.4660 C 0 0 1 0 0 0 0 0 0 0 0 0 6.6382 -0.0625 -0.9203 C 0 0 1 0 0 0 0 0 0 0 0 0 5.8659 0.9812 -1.6815 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4350 0.5891 -1.7793 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0099 -0.5407 -0.8704 C 0 0 1 0 0 0 0 0 0 0 0 0 4.5920 -0.3226 0.4731 C 0 0 1 0 0 0 0 0 0 0 0 0 4.2560 -1.5526 1.3288 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8676 0.8315 1.1411 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4743 0.3629 1.3915 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7740 0.1440 0.0985 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5204 -0.6511 -0.9128 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5345 -0.4387 0.3696 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5280 0.3933 0.0305 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.3188 -0.3134 -1.0676 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5809 0.4642 -1.3729 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.3424 1.6724 -1.9938 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3207 0.6278 -0.0427 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.3929 1.4356 0.8339 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.3159 0.6123 1.1573 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0566 1.9818 2.0561 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5665 1.1692 -0.2132 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.5301 0.2481 0.1818 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.2820 0.8214 1.3339 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.6570 0.2388 1.5295 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.6134 -1.0968 1.9249 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.3612 0.3768 0.1935 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.5692 -0.3565 -0.8127 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.2530 -0.0870 -0.9123 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.1901 -0.1389 -2.1807 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.6439 -0.1526 0.2302 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.6488 0.7396 -0.0151 C 0 0 1 0 0 0 0 0 0 0 0 0 -11.5905 0.3925 -1.1156 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.4706 -0.7915 -0.7940 C 0 0 2 0 0 0 0 0 0 0 0 0 -13.4590 -0.8870 -1.7620 O 0 0 0 0 0 0 0 0 0 0 0 0 -13.1393 -0.5390 0.5249 C 0 0 1 0 0 0 0 0 0 0 0 0 -12.0708 -0.1977 1.5407 C 0 0 2 0 0 0 0 0 0 0 0 0 -11.3272 0.9130 1.2139 O 0 0 0 0 0 0 0 0 0 0 0 0 -11.2380 -1.4096 1.8995 C 0 0 0 0 0 0 0 0 0 0 0 0 -13.9776 0.5564 0.3968 O 0 0 0 0 0 0 0 0 0 0 0 0 8.5782 -0.4214 -2.1590 O 0 0 0 0 0 0 0 0 0 0 0 0 11.4127 -0.6715 2.6205 H 0 0 0 0 0 0 0 0 0 0 0 0 10.8510 -2.1188 1.7128 H 0 0 0 0 0 0 0 0 0 0 0 0 12.5338 0.0850 -1.2161 H 0 0 0 0 0 0 0 0 0 0 0 0 10.0127 0.9812 1.2056 H 0 0 0 0 0 0 0 0 0 0 0 0 10.5431 2.2995 -0.5967 H 0 0 0 0 0 0 0 0 0 0 0 0 10.1339 1.3113 -2.8330 H 0 0 0 0 0 0 0 0 0 0 0 0 8.3990 2.1059 -1.8945 H 0 0 0 0 0 0 0 0 0 0 0 0 8.2756 2.1318 -0.0477 H 0 0 0 0 0 0 0 0 0 0 0 0 8.5133 -2.2042 -1.1603 H 0 0 0 0 0 0 0 0 0 0 0 0 8.8777 -2.6762 0.5244 H 0 0 0 0 0 0 0 0 0 0 0 0 10.1743 -2.1291 -0.5692 H 0 0 0 0 0 0 0 0 0 0 0 0 7.9837 0.5249 1.8344 H 0 0 0 0 0 0 0 0 0 0 0 0 8.7714 -1.0932 2.2040 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3524 -1.2614 2.2804 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9505 -2.0714 0.7238 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3040 0.8901 0.9340 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4021 -1.0519 -1.4141 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9085 1.9791 -1.1820 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2699 1.1121 -2.7164 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7322 1.4387 -1.5754 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1815 0.2947 -2.8421 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4616 -1.4731 -1.2970 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2458 -1.2899 2.4067 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2922 -1.9948 0.9791 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0018 -2.3576 1.2103 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3313 1.1004 2.1111 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8239 1.6932 0.4443 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3975 -0.5141 2.0478 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9702 1.1921 1.9741 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5403 1.1607 -0.3200 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2549 -1.7216 -0.7792 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1540 -0.3748 -1.9233 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1271 1.3208 -0.3740 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6685 -1.3077 -0.6855 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6550 -0.4402 -1.9252 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1709 -0.1545 -2.0789 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2080 1.9670 -2.3993 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3548 -0.4211 0.3763 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9759 2.2435 0.1779 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4343 2.7914 2.5205 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9758 2.5311 1.7001 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2992 1.1681 2.7632 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0028 -0.6619 0.5306 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6924 0.7124 2.2735 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4150 1.9149 1.1577 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.1517 0.8492 2.3185 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8945 -1.2378 2.5650 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.3699 1.4590 -0.0485 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.6849 -1.4601 -0.5975 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.6860 0.8640 -2.2184 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.9457 -0.9088 -2.4202 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3981 -0.0985 -2.9859 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.2457 1.7741 -0.2202 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.2536 1.2918 -1.2722 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.0517 0.1833 -2.0365 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.8496 -1.7057 -0.8047 H 0 0 0 0 0 0 0 0 0 0 0 0 -13.1515 -0.5157 -2.6269 H 0 0 0 0 0 0 0 0 0 0 0 0 -13.6633 -1.4385 0.9129 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.6311 0.0764 2.4827 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.0272 -2.0469 1.0291 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.3167 -1.1035 2.4183 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.8037 -2.0584 2.6328 H 0 0 0 0 0 0 0 0 0 0 0 0 -14.6791 0.3828 -0.2758 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0345 -0.1085 -2.9363 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 2 3 1 0 3 4 1 0 4 5 1 0 5 6 2 0 5 7 1 0 7 8 1 0 8 9 1 0 8 10 1 0 10 11 1 0 11 12 1 0 12 13 1 6 12 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 1 21 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 25 27 1 0 27 28 1 0 28 29 1 0 29 30 1 0 30 31 1 0 30 32 1 0 32 33 1 0 33 34 1 0 33 35 1 0 32 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 42 44 1 0 41 45 1 0 45 46 1 0 46 47 1 0 47 48 1 0 48 49 1 0 48 50 1 0 50 51 1 0 51 52 1 0 51 53 1 0 50 54 1 0 11 55 1 6 6 2 1 0 12 7 1 0 21 16 1 0 34 28 1 0 43 37 1 0 52 46 1 0 17 11 1 0 26 20 1 0 4 56 1 0 4 57 1 0 6 58 1 0 7 59 1 1 8 60 1 1 9 61 1 0 10 62 1 0 10 63 1 0 13 64 1 0 13 65 1 0 13 66 1 0 14 67 1 0 14 68 1 0 15 69 1 0 15 70 1 0 16 71 1 1 17 72 1 6 18 73 1 0 18 74 1 0 19 75 1 0 19 76 1 0 20 77 1 6 22 78 1 0 22 79 1 0 22 80 1 0 23 81 1 0 23 82 1 0 24 83 1 0 24 84 1 0 25 85 1 6 26 86 1 0 26 87 1 0 28 88 1 6 29 89 1 0 29 90 1 0 30 91 1 6 31 92 1 0 32 93 1 1 33 94 1 6 35 95 1 0 35 96 1 0 35 97 1 0 37 98 1 1 38 99 1 0 38100 1 0 39101 1 1 40102 1 0 41103 1 6 42104 1 1 44105 1 0 44106 1 0 44107 1 0 46108 1 6 47109 1 0 47110 1 0 48111 1 1 49112 1 0 50113 1 1 51114 1 1 53115 1 0 53116 1 0 53117 1 0 54118 1 0 55119 1 0 M END

Standard InCHIKey	LKRDZKPBAOKJBT-CNPIRKNPSA-N
Standard InCHI	InChI=1S/C41H64O14/c1-19-36(47)27(42)14-33(50-19)54-38-21(3)52-34(16-29(38)44)55-37-20(2)51-32(15-28(37)43)53-24-8-10-39(4)23(13-24)6-7-26-25(39)9-11-40(5)35(22-12-31(46)49-18-22)30(45)17-41(26,40)48/h12,19-21,23-30,32-38,42-45,47-48H,6-11,13-18H2,1-5H3/t19-,20-,21-,23-,24+,25+,26-,27+,28+,29+,30+,32+,33+,34+,35+,36-,37-,38-,39+,40-,41+/m1/s1
SMILES	O=C1OCC(=C1)[C@H]1[C@@H](O)C[C@]2([C@]1(C)CC[C@H]1[C@H]2CC[C@H]2[C@]1(C)CC[C@@H](C2)O[C@H]1C[C@H](O)[C@@H]([C@H](O1)C)O[C@H]1C[C@H](O)[C@@H]([C@H](O1)C)O[C@H]1C[C@H](O)[C@@H]([C@H](O1)C)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	780.43	Volume:	767.03 ? Van der Waals volume.
Dense:	1.017	LogP:	1.831 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.486 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.735 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	7.0	Rigid Bonds:	44.0
TPSA:	203.06 ? Topological Polar Surface Area.	H-Bond Acceptor:	14.0
H-Bond Donor:	6.0	Rings:	8.0
Heavy Atoms:	14.0

MedChem Properties

QED Drug-Likeness Score:	0.162	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	6.11	Fsp³:	0.927
MCE-18:	150.278 ? 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:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.736	Fluc inhibitor:	0.001 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.017 ? 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:	0.25	Promiscuous compounds:	0.715

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.643	MDCK Permeability:	-5.222
Pgp-inhibitor:	0.008	Pgp-substrate:	0.979
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):	0.001
20% Bioavailability (F20%):	0.077	30% Bioavailability (F30%):	0.05
50% Bioavailability (F50%):	0.853

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.917
Plasma Protein Binding (PPB):	66.726%	Volume Distribution (VD):	-0.566
Fu:	27.263% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.995
OATP1B3 inhibitor:	0.881	BCRP inhibitor:	0.003
BSEP inhibitor:	0.984

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.031	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.998	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.953
HLM stability:	0.012 ? 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):

1.26

Half-life (T1/2):

4.855

ADMET: Toxicity

hERG Blockers:	0.049	hERG Blockers (10um):	0.775
Human Hepatotoxicity (H-HT):	0.264	Drug-induced Liver Injury (DILI):	0.993
AMES Toxicity:	0.994	Rat Oral Acute Toxicity:	0.991
Maximum Recommended Daily Dose:	0.999	Skin Sensitization:	1.0
Carcinogencity:	0.631	Eye Corrosion:	0.0
Eye Irritation:	0.0	Respiratory Toxicity:	0.996
Drug-induced Neurotoxicity:	0.043	Ototoxicity:	0.971
Hematotoxicity:	0.966	Drug-induced Nephrotoxicity:	0.984
Genotoxicity:	0.987	RPMI-8226 Immunitoxicity:	0.861
A549 Cytotoxicity:	0.957	Hek293 Cytotoxicity:	0.945
BCF:	0.491 ? 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:	3.252 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.88 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.93 ? 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
NPO4443	Digitalis purpurea	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1007/s00253-012-4489-y]
NPO17774	Hemerocallis fulva	Species	Xanthorrhoeaceae	Eukaryota	Flowers	n.a.	n.a.	DOI[10.1016/j.lwt.2014.11.023]
NPO22245	Digitalis lanata	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/S0176-1617(89)80112-9]
NPO4443	Digitalis purpurea	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1093/oxfordjournals.pcp.a076462]
NPO4443	Digitalis purpurea	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9834166]
NPO12474	Cordyline fruticosa	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22245	Digitalis lanata	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1551	Luffa aegyptiaca	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18930	Rubus coreanus	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27168	Atropa belladona	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4443	Digitalis purpurea	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13401	Phoenix canariensis	Species	Arecaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18180	Erysimum repandum	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1551	Luffa aegyptiaca	Species	Cucurbitaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO1551	Luffa aegyptiaca	Species	Cucurbitaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO1551	Luffa aegyptiaca	Species	Cucurbitaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO1551	Luffa aegyptiaca	Species	Cucurbitaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO4443	Digitalis purpurea	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13401	Phoenix canariensis	Species	Arecaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22245	Digitalis lanata	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17774	Hemerocallis fulva	Species	Xanthorrhoeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19015	Begonia glabra	Species	Begoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22245	Digitalis lanata	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19015	Begonia glabra	Species	Begoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1551	Luffa aegyptiaca	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17774	Hemerocallis fulva	Species	Xanthorrhoeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4443	Digitalis purpurea	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13401	Phoenix canariensis	Species	Arecaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17774	Hemerocallis fulva	Species	Xanthorrhoeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO22245	Digitalis lanata	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO19015	Begonia glabra	Species	Begoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO4443	Digitalis purpurea	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO4443	Digitalis purpurea	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO17774	Hemerocallis fulva	Species	Xanthorrhoeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO1551	Luffa aegyptiaca	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO18930	Rubus coreanus	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO22245	Digitalis lanata	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO19093	Streptomyces aburaviensis	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO27168	Atropa belladona	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19175	Iguana iguana	Species	Iguanidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19441	Strychnos splendens	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12474	Cordyline fruticosa	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13401	Phoenix canariensis	Species	Arecaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19015	Begonia glabra	Species	Begoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4443	Digitalis purpurea	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18180	Erysimum repandum	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22245	Digitalis lanata	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17635	Aria arguta	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17774	Hemerocallis fulva	Species	Xanthorrhoeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1551	Luffa aegyptiaca	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18930	Rubus coreanus	Species	Rosaceae	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
Potency	19
Inhibition	2
IC50 ratio	4
Relative Ki	1
Ratio IC50	1
IC50	5
GI50	59

Activity Type	# Activity
Individual protein	11
Cell line	64
Organism	2
Others	14

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT152	Individual protein	Nuclear factor erythroid 2-related factor 2	Homo sapiens	Potency	n.a.	92.0	nM	PubChem BioAssay data set
NPT135	Individual protein	Chromobox protein homolog 1	Homo sapiens	Potency	n.a.	89125.1	nM	PubChem BioAssay data set
NPT154	Individual protein	Mothers against decapentaplegic homolog 3	Homo sapiens	Potency	n.a.	316.2	nM	PubChem BioAssay data set
NPT10	Individual protein	Geminin	Homo sapiens	Potency	n.a.	461.1	nM	PubChem BioAssay data set
NPT10	Individual protein	Geminin	Homo sapiens	Potency	n.a.	1835.6	nM	PubChem BioAssay data set
NPT101	Individual protein	Glucagon-like peptide 1 receptor	Homo sapiens	Potency	n.a.	501.2	nM	PubChem BioAssay data set
NPT72	Individual protein	Solute carrier organic anion transporter family member 1B3	Homo sapiens	Inhibition	=	102.16	%	PMID[23571415]
NPT698	Individual protein	Regulator of G-protein signaling 4	Homo sapiens	Potency	n.a.	70794.6	nM	PubChem BioAssay data set
NPT73	Individual protein	Solute carrier organic anion transporter family member 1B1	Homo sapiens	Inhibition	=	103.38	%	PMID[23571415]
NPT478	Individual protein	Ataxin-2	Homo sapiens	Potency	n.a.	89.1	nM	PubChem BioAssay data set
NPT861	Individual protein	Isocitrate dehydrogenase [NADP] cytoplasmic	Homo sapiens	Potency	n.a.	1032.3	nM	PubChem BioAssay data set

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT384	Cell line	TK-10	Homo sapiens	IC50	=	131.2	nM	PMID[16309315]
NPT83	Cell line	MCF7	Homo sapiens	IC50	=	251.9	nM	PMID[16309315]
NPT398	Cell line	UACC-62	Homo sapiens	IC50	=	369.4	nM	PMID[16309315]
NPT65	Cell line	HepG2	Homo sapiens	Potency	n.a.	446.7	nM	PubChem BioAssay data set
NPT71	Cell line	HEK293	Homo sapiens	Potency	n.a.	316.2	nM	PubChem BioAssay data set
NPT368	Cell line	SN12C	Homo sapiens	GI50	n.a.	164.44	nM	PubChem BioAssay data set
NPT367	Cell line	MDA-N	Homo sapiens	GI50	n.a.	266.07	nM	PubChem BioAssay data set
NPT369	Cell line	ACHN	Homo sapiens	GI50	n.a.	94.84	nM	PubChem BioAssay data set
NPT370	Cell line	NCI-H23	Homo sapiens	GI50	n.a.	86.9	nM	PubChem BioAssay data set
NPT371	Cell line	UO-31	Homo sapiens	GI50	n.a.	218.78	nM	PubChem BioAssay data set
NPT116	Cell line	HL-60	Homo sapiens	GI50	n.a.	116.41	nM	PubChem BioAssay data set
NPT372	Cell line	HOP-92	Homo sapiens	GI50	n.a.	401.79	nM	PubChem BioAssay data set
NPT90	Cell line	DU-145	Homo sapiens	GI50	n.a.	82.22	nM	PubChem BioAssay data set
NPT374	Cell line	SF-539	Homo sapiens	GI50	n.a.	100.0	nM	PubChem BioAssay data set
NPT373	Cell line	SK-MEL-5	Homo sapiens	GI50	n.a.	118.3	nM	PubChem BioAssay data set
NPT375	Cell line	Malme-3M	Homo sapiens	GI50	n.a.	205.59	nM	PubChem BioAssay data set
NPT376	Cell line	A498	Homo sapiens	GI50	n.a.	236.59	nM	PubChem BioAssay data set
NPT111	Cell line	K562	Homo sapiens	GI50	n.a.	361.41	nM	PubChem BioAssay data set
NPT377	Cell line	OVCAR-3	Homo sapiens	GI50	n.a.	130.02	nM	PubChem BioAssay data set
NPT112	Cell line	MOLT-4	Homo sapiens	GI50	n.a.	27.73	nM	PubChem BioAssay data set
NPT378	Cell line	NCI/ADR-RES	Homo sapiens	GI50	n.a.	197.24	nM	PubChem BioAssay data set
NPT379	Cell line	HOP-62	Homo sapiens	GI50	n.a.	566.24	nM	PubChem BioAssay data set
NPT380	Cell line	U-251	Homo sapiens	GI50	n.a.	258.23	nM	PubChem BioAssay data set
NPT382	Cell line	OVCAR-5	Homo sapiens	GI50	n.a.	656.15	nM	PubChem BioAssay data set
NPT381	Cell line	OVCAR-8	Homo sapiens	GI50	n.a.	226.46	nM	PubChem BioAssay data set
NPT82	Cell line	MDA-MB-231	Homo sapiens	GI50	n.a.	1202.26	nM	PubChem BioAssay data set
NPT383	Cell line	SNB-19	Homo sapiens	GI50	n.a.	714.5	nM	PubChem BioAssay data set
NPT385	Cell line	SR	Homo sapiens	GI50	n.a.	287.08	nM	PubChem BioAssay data set
NPT384	Cell line	TK-10	Homo sapiens	GI50	n.a.	254.1	nM	PubChem BioAssay data set
NPT323	Cell line	SW-620	Homo sapiens	GI50	n.a.	257.63	nM	PubChem BioAssay data set
NPT455	Cell line	NCI-H522	Homo sapiens	GI50	n.a.	23.82	nM	PubChem BioAssay data set
NPT386	Cell line	KM12	Homo sapiens	GI50	n.a.	657.66	nM	PubChem BioAssay data set
NPT387	Cell line	M14	Homo sapiens	GI50	n.a.	475.34	nM	PubChem BioAssay data set
NPT388	Cell line	NCI-H322M	Homo sapiens	GI50	n.a.	234.96	nM	PubChem BioAssay data set
NPT389	Cell line	RPMI-8226	Homo sapiens	GI50	n.a.	196.79	nM	PubChem BioAssay data set
NPT456	Cell line	OVCAR-4	Homo sapiens	GI50	n.a.	271.02	nM	PubChem BioAssay data set
NPT390	Cell line	LOX IMVI	Homo sapiens	GI50	n.a.	215.28	nM	PubChem BioAssay data set
NPT457	Cell line	BT-549	Homo sapiens	GI50	n.a.	115.88	nM	PubChem BioAssay data set
NPT147	Cell line	SK-MEL-2	Homo sapiens	GI50	n.a.	543.25	nM	PubChem BioAssay data set
NPT391	Cell line	HCC 2998	Homo sapiens	GI50	n.a.	4187.94	nM	PubChem BioAssay data set
NPT81	Cell line	A549	Homo sapiens	GI50	n.a.	71.94	nM	PubChem BioAssay data set
NPT392	Cell line	SNB-75	Homo sapiens	GI50	n.a.	703.07	nM	PubChem BioAssay data set
NPT148	Cell line	HCT-15	Homo sapiens	GI50	n.a.	592.93	nM	PubChem BioAssay data set
NPT393	Cell line	HCT-116	Homo sapiens	GI50	n.a.	126.77	nM	PubChem BioAssay data set
NPT395	Cell line	SF-268	Homo sapiens	GI50	n.a.	151.71	nM	PubChem BioAssay data set
NPT306	Cell line	PC-3	Homo sapiens	GI50	n.a.	259.42	nM	PubChem BioAssay data set
NPT394	Cell line	EKVX	Homo sapiens	GI50	n.a.	164.44	nM	PubChem BioAssay data set
NPT146	Cell line	SK-OV-3	Homo sapiens	GI50	n.a.	389.94	nM	PubChem BioAssay data set
NPT397	Cell line	NCI-H460	Homo sapiens	GI50	n.a.	131.83	nM	PubChem BioAssay data set
NPT396	Cell line	T47D	Homo sapiens	GI50	n.a.	419.76	nM	PubChem BioAssay data set
NPT398	Cell line	UACC-62	Homo sapiens	GI50	n.a.	417.83	nM	PubChem BioAssay data set
NPT400	Cell line	MDA-MB-435	Homo sapiens	GI50	n.a.	364.75	nM	PubChem BioAssay data set
NPT308	Cell line	CAKI-1	Homo sapiens	GI50	n.a.	106.91	nM	PubChem BioAssay data set
NPT458	Cell line	IGROV-1	Homo sapiens	GI50	n.a.	415.91	nM	PubChem BioAssay data set
NPT399	Cell line	SF-295	Homo sapiens	GI50	n.a.	168.66	nM	PubChem BioAssay data set
NPT401	Cell line	786-0	Homo sapiens	GI50	n.a.	151.01	nM	PubChem BioAssay data set
NPT402	Cell line	Hs-578T	Homo sapiens	GI50	n.a.	562.34	nM	PubChem BioAssay data set
NPT403	Cell line	UACC-257	Homo sapiens	GI50	n.a.	522.4	nM	PubChem BioAssay data set
NPT404	Cell line	CCRF-CEM	Homo sapiens	GI50	n.a.	108.89	nM	PubChem BioAssay data set
NPT405	Cell line	NCI-H226	Homo sapiens	GI50	n.a.	855.07	nM	PubChem BioAssay data set
NPT170	Cell line	SK-MEL-28	Homo sapiens	GI50	n.a.	1145.51	nM	PubChem BioAssay data set
NPT139	Cell line	HT-29	Homo sapiens	GI50	n.a.	176.6	nM	PubChem BioAssay data set
NPT406	Cell line	RXF 393	Homo sapiens	GI50	n.a.	99.08	nM	PubChem BioAssay data set
NPT407	Cell line	COLO 205	Homo sapiens	GI50	n.a.	797.99	nM	PubChem BioAssay data set
NPT20555	Organism	SARS-CoV-2	Severe acute respiratory syndrome coronavirus 2	IC50	>	20000.0	nM	DOI[10.6019/CHEMBL4651402]
NPT20555	Organism	SARS-CoV-2	Severe acute respiratory syndrome coronavirus 2	IC50	>	19952.62	nM	DOI[10.6019/CHEMBL4651402]
NPT897	Others	Monoclonal antibody (mAb)	n.a.	IC50 ratio	=	11.0	n.a.	PMID[12109909]
NPT897	Others	Monoclonal antibody (mAb)	n.a.	IC50 ratio	=	81.0	n.a.	PMID[12109909]
NPT897	Others	Monoclonal antibody (mAb)	n.a.	IC50 ratio	=	73.0	n.a.	PMID[12109909]
NPT897	Others	Monoclonal antibody (mAb)	n.a.	IC50 ratio	=	130.0	n.a.	PMID[12109909]
NPT897	Others	Monoclonal antibody (mAb)	n.a.	Relative Ki	=	16.0	n.a.	PMID[12109909]
NPT2	Others	Unspecified	n.a.	Ratio IC50	=	46.0	n.a.	PMID[2089119]
NPT2	Others	Unspecified	n.a.	Potency	n.a.	461.1	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	n.a.	125.9	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	n.a.	354.8	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	n.a.	1412.5	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	n.a.	580.5	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	n.a.	354813.4	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	n.a.	316.2	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	n.a.	89.1	nM	PubChem BioAssay data set

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
-	Cavia porcellus	LD50	>	130.0	mg/kg	ToxVal

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 NPC193893 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	15521
0.1-0.2	29982
0.2-0.3	4007
0.3-0.4	164
0.4-0.5	104
0.5-0.6	56
0.6-0.7	13
0.7-0.8	2
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8375	Intermediate Similarity	NPC72260
0.7619	Intermediate Similarity	NPC173555
0.75	Intermediate Similarity	NPC471633
0.7108	Intermediate Similarity	NPC99080
0.6706	Remote Similarity	NPC479356
0.6706	Remote Similarity	NPC479355
0.6703	Remote Similarity	NPC231518
0.6703	Remote Similarity	NPC488944
0.6702	Remote Similarity	NPC475219
0.663	Remote Similarity	NPC55532
0.6429	Remote Similarity	NPC120390
0.6429	Remote Similarity	NPC74259
0.6392	Remote Similarity	NPC475590
0.6289	Remote Similarity	NPC479360
0.6289	Remote Similarity	NPC479359
0.6279	Remote Similarity	NPC99620
0.6277	Remote Similarity	NPC208193
0.5938	Remote Similarity	NPC125077
0.5909	Remote Similarity	NPC473852
0.5889	Remote Similarity	NPC84949
0.5889	Remote Similarity	NPC480562
0.5889	Remote Similarity	NPC74945
0.5889	Remote Similarity	NPC31354
0.5889	Remote Similarity	NPC69576
0.5882	Remote Similarity	NPC117445
0.5882	Remote Similarity	NPC308262
0.5789	Remote Similarity	NPC236973
0.5778	Remote Similarity	NPC5311
0.5745	Remote Similarity	NPC103534
0.5745	Remote Similarity	NPC44899
0.5745	Remote Similarity	NPC304260
0.5745	Remote Similarity	NPC29639
0.5625	Remote Similarity	NPC220217
0.5618	Remote Similarity	NPC474418
0.5612	Remote Similarity	NPC486143
0.5612	Remote Similarity	NPC486142
0.5612	Remote Similarity	NPC486149
0.5591	Remote Similarity	NPC93883
0.5543	Remote Similarity	NPC199428
0.5543	Remote Similarity	NPC109448
0.5543	Remote Similarity	NPC310341
0.549	Remote Similarity	NPC488943
0.549	Remote Similarity	NPC488942
0.5435	Remote Similarity	NPC469750
0.5429	Remote Similarity	NPC474908
0.5426	Remote Similarity	NPC484202
0.5421	Remote Similarity	NPC474423
0.5417	Remote Similarity	NPC488935
0.5417	Remote Similarity	NPC5883
0.5417	Remote Similarity	NPC488936
0.5376	Remote Similarity	NPC76572
0.5376	Remote Similarity	NPC193382
0.5361	Remote Similarity	NPC30483
0.5361	Remote Similarity	NPC470897
0.5347	Remote Similarity	NPC486146
0.5333	Remote Similarity	NPC475419
0.5306	Remote Similarity	NPC292467
0.5288	Remote Similarity	NPC486144
0.5288	Remote Similarity	NPC486145
0.5288	Remote Similarity	NPC486147
0.5288	Remote Similarity	NPC486148
0.5253	Remote Similarity	NPC475556
0.5253	Remote Similarity	NPC311706
0.5192	Remote Similarity	NPC488938
0.5192	Remote Similarity	NPC488937
0.5185	Remote Similarity	NPC488945
0.5185	Remote Similarity	NPC488946
0.5152	Remote Similarity	NPC40749
0.5104	Remote Similarity	NPC179412
0.5104	Remote Similarity	NPC471356
0.5104	Remote Similarity	NPC471353
0.505	Remote Similarity	NPC488941
0.505	Remote Similarity	NPC488940

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC193893 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6268
0.1-0.2	2775
0.2-0.3	91
0.3-0.4	6
0.4-0.5	2
0.5-0.6	0
0.6-0.7	5
0.7-0.8	2
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8375	Intermediate Similarity	NPD8294	Phase 4
0.7619	Intermediate Similarity	NPD8296	Phase 4
0.7	Intermediate Similarity	NPD8377	Phase 4
0.6703	Remote Similarity	NPD8033	Approved
0.6667	Remote Similarity	NPD8380	Approved
0.6552	Remote Similarity	NPD8335	Phase 4
0.6383	Remote Similarity	NPD8378	Pre-clinical
0.6383	Remote Similarity	NPD8379	Approved

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