NPASS Compound

Natural Product: NPC110139

Natural Product ID	NPC110139
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	2Alpha,3Alpha,23Alpha-Trihydroxy-Urs-12-En-28-Oic Acid 28-Obeta-D-Glucopyranoside
IUPAC Name	[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] (1S,2R,4aS,6aR,6aS,6bR,8aR,9R,10S,11R,12aR,14bS)-10,11-dihydroxy-9-(hydroxymethyl)-1,2,6a,6b,9,12a-hexamethyl-2,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydro-1H-picene-4a-carboxylate
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL1956941
PubChem CID	57396551
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0002049] Terpene glycosides [CHEMONTID:0001580] Triterpene glycosides [CHEMONTID:0002358] Triterpene 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 104109 0 0 0 0 0 0 0 0999 V2000 8.4477 -0.7409 -2.8088 O 0 0 0 0 0 0 0 0 0 0 0 0 7.4197 -0.3254 -1.9817 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5969 -0.9050 -0.5807 C 0 0 1 0 0 0 0 0 0 0 0 0 6.5892 -0.5093 0.2552 O 0 0 0 0 0 0 0 0 0 0 0 0 5.3872 -1.1686 0.1201 C 0 0 1 0 0 0 0 0 0 0 0 0 4.4269 -0.3784 -0.5303 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3041 0.0357 0.1243 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1608 -0.3124 1.3240 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2142 0.8737 -0.4519 C 0 0 2 0 0 0 0 0 0 0 0 0 2.9046 2.1720 -0.9006 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4898 2.8179 0.3369 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3451 3.3940 1.1136 C 0 0 2 0 0 0 0 0 0 0 0 0 1.0203 2.7586 0.7475 C 0 0 1 0 0 0 0 0 0 0 0 0 1.2209 1.2841 0.5974 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0334 0.5006 0.5427 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5585 0.0815 1.6580 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7975 -0.7103 1.8340 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6633 -0.3265 0.6297 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.9708 -0.5825 -0.6538 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.6933 0.1902 -0.7297 C 0 0 2 0 0 0 0 0 0 0 0 0 0.3911 -0.5566 -1.5146 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6628 0.2073 -1.6451 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9593 1.4224 -1.5775 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6519 -2.0304 -0.9301 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9217 -0.1618 -1.7713 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3157 -0.7642 -1.5811 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8776 -0.1920 -0.2964 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.0707 -0.8067 0.8053 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.2446 -2.2853 0.9478 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5437 -0.2057 2.1330 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0594 -0.1844 2.2452 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.7115 0.5243 1.1171 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.3383 -0.1994 -0.1693 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.0017 -1.5417 -0.2563 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9391 0.6524 -1.2726 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4978 1.9728 -1.2208 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.2310 1.8292 1.0437 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.3158 0.4461 3.4860 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1205 2.9508 1.9780 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2451 4.8741 0.7299 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5075 -2.5524 -0.4806 C 0 0 1 0 0 0 0 0 0 0 0 0 6.8074 -3.1392 0.0584 C 0 0 2 0 0 0 0 0 0 0 0 0 7.9240 -2.3597 -0.5756 C 0 0 2 0 0 0 0 0 0 0 0 0 9.0777 -2.6444 0.1934 O 0 0 0 0 0 0 0 0 0 0 0 0 6.8908 -4.5113 -0.1883 O 0 0 0 0 0 0 0 0 0 0 0 0 4.4933 -3.4041 -0.0143 O 0 0 0 0 0 0 0 0 0 0 0 0 9.1834 -1.0601 -2.2214 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4227 -0.4699 -2.3915 H 0 0 0 0 0 0 0 0 0 0 0 0 7.5604 0.7890 -1.8568 H 0 0 0 0 0 0 0 0 0 0 0 0 8.5265 -0.3817 -0.1961 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0241 -1.3441 1.1676 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6821 1.9073 -1.6315 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2009 2.8720 -1.3506 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0894 2.0779 0.9398 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2184 3.5820 -0.0040 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5291 3.2547 2.1802 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5692 3.3117 -0.0470 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7391 1.0547 1.5872 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0391 0.3299 2.6063 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3421 -0.3765 2.7487 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6304 -1.7823 1.9301 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7353 0.7841 0.7154 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0638 -0.7446 -2.5613 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6270 -1.5441 -1.0779 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4207 -0.5583 -2.0128 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6415 0.9126 -2.5331 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0141 1.9148 -1.8796 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3115 1.0378 -2.5529 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6150 2.1533 -1.1143 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5983 -2.6489 -1.0175 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9435 -2.4904 -0.2457 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2833 -2.0723 -1.9742 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1044 0.9381 -1.6679 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6148 -0.4862 -2.7662 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3518 -1.8427 -1.6650 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9081 -0.3418 -2.4148 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5608 0.8979 -0.3182 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9358 -2.5546 1.8084 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2785 -2.7237 1.2665 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7093 -2.7927 0.0916 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1058 0.7913 2.3054 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2560 -0.9435 2.9445 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4135 -1.2172 2.3758 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.7921 0.4993 1.2362 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.0903 -1.3370 -0.4882 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6165 -2.0537 -1.1595 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9949 -2.1334 0.6557 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.0512 0.6282 -1.0741 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8151 0.1712 -2.2563 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2578 2.5465 -1.4666 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1308 2.2354 1.9524 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6848 0.0037 4.1280 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6602 2.6044 2.8638 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8750 2.5174 1.8265 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0061 4.0725 2.0545 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8748 5.4556 1.5754 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2467 5.2692 0.4450 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5990 5.0159 -0.1611 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5892 -2.5567 -1.5677 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7830 -2.9776 1.1555 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0759 -2.7496 -1.6226 H 0 0 0 0 0 0 0 0 0 0 0 0 9.0789 -3.5947 0.4564 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5682 -5.0048 0.6291 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8005 -4.3346 -0.2395 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 2 0 9 7 1 1 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 2 0 16 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 20 21 1 0 21 22 1 0 20 23 1 6 19 24 1 6 19 25 1 0 25 26 1 0 26 27 1 0 27 28 1 0 28 29 1 1 28 30 1 0 30 31 1 0 31 32 1 0 32 33 1 0 33 34 1 1 33 35 1 0 35 36 1 0 32 37 1 0 31 38 1 0 13 39 1 0 12 40 1 0 5 41 1 0 41 42 1 0 42 43 1 0 43 44 1 0 42 45 1 0 41 46 1 0 43 3 1 0 22 9 1 0 33 27 1 0 14 9 1 0 20 15 1 0 28 18 1 0 1 47 1 0 2 48 1 0 2 49 1 0 3 50 1 1 5 51 1 1 10 52 1 0 10 53 1 0 11 54 1 0 11 55 1 0 12 56 1 1 13 57 1 6 14 58 1 1 16 59 1 0 17 60 1 0 17 61 1 0 18 62 1 1 21 63 1 0 21 64 1 0 22 65 1 0 22 66 1 0 23 67 1 0 23 68 1 0 23 69 1 0 24 70 1 0 24 71 1 0 24 72 1 0 25 73 1 0 25 74 1 0 26 75 1 0 26 76 1 0 27 77 1 6 29 78 1 0 29 79 1 0 29 80 1 0 30 81 1 0 30 82 1 0 31 83 1 1 32 84 1 1 34 85 1 0 34 86 1 0 34 87 1 0 35 88 1 0 35 89 1 0 36 90 1 0 37 91 1 0 38 92 1 0 39 93 1 0 39 94 1 0 39 95 1 0 40 96 1 0 40 97 1 0 40 98 1 0 41 99 1 6 42100 1 1 43101 1 6 44102 1 0 45103 1 0 46104 1 0 M END

Standard InCHIKey	OEGYWKLSOORPGU-SZZHKNJGSA-N
Standard InCHI	InChI=1S/C36H58O10/c1-18-9-12-36(31(44)46-30-28(42)27(41)26(40)22(16-37)45-30)14-13-34(5)20(25(36)19(18)2)7-8-24-32(3)15-21(39)29(43)33(4,17-38)23(32)10-11-35(24,34)6/h7,18-19,21-30,37-43H,8-17H2,1-6H3/t18-,19+,21-,22-,23-,24-,25+,26-,27+,28-,29-,30+,32+,33+,34-,35-,36+/m1/s1
SMILES	OC[C@H]1O[C@@H](OC(=O)[C@@]23CC[C@H]([C@@H]([C@H]3C3=CC[C@H]4[C@@]([C@@]3(CC2)C)(C)CC[C@@H]2[C@]4(C)C[C@H]([C@H]([C@@]2(C)CO)O)O)C)C)[C@@H]([C@H]([C@@H]1O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	650.4	Volume:	662.503 ? Van der Waals volume.
Dense:	0.982	LogP:	2.186 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.675 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.324 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	5.0	Rigid Bonds:	33.0
TPSA:	177.14 ? Topological Polar Surface Area.	H-Bond Acceptor:	10.0
H-Bond Donor:	7.0	Rings:	6.0
Heavy Atoms:	10.0

MedChem Properties

QED Drug-Likeness Score:	0.177	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.543	Fsp³:	0.917
MCE-18:	128.058 ? 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:	0.807	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.072 ? 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:	0.16	Promiscuous compounds:	0.075

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.984	MDCK Permeability:	-5.185
Pgp-inhibitor:	0.0	Pgp-substrate:	0.565
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):	0.035
20% Bioavailability (F20%):	0.776	30% Bioavailability (F30%):	0.978
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.505	MRP1:	0.083
Plasma Protein Binding (PPB):	73.752%	Volume Distribution (VD):	-0.339
Fu:	20.432% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.931	BCRP inhibitor:	0.251
BSEP inhibitor:	0.273

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:	0.254
HLM stability:	0.031 ? 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):

1.468

Half-life (T1/2):

2.795

ADMET: Toxicity

hERG Blockers:	0.008	hERG Blockers (10um):	0.037
Human Hepatotoxicity (H-HT):	0.513	Drug-induced Liver Injury (DILI):	0.297
AMES Toxicity:	0.652	Rat Oral Acute Toxicity:	0.012
Maximum Recommended Daily Dose:	0.034	Skin Sensitization:	0.996
Carcinogencity:	0.39	Eye Corrosion:	0.0
Eye Irritation:	0.012	Respiratory Toxicity:	0.032
Drug-induced Neurotoxicity:	0.001	Ototoxicity:	0.993
Hematotoxicity:	0.488	Drug-induced Nephrotoxicity:	0.905
Genotoxicity:	0.189	RPMI-8226 Immunitoxicity:	0.055
A549 Cytotoxicity:	0.174	Hek293 Cytotoxicity:	0.153
BCF:	1.035 ? 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:	3.513 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.081 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.259 ? 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
NPO6515	Juglans sinensis	Species	Juglandaceae	Eukaryota	n.a.	twig	n.a.	PMID[21309591]
NPO6515	Juglans sinensis	Species	Juglandaceae	Eukaryota	n.a.	leaf	n.a.	PMID[21309591]
NPO941	Tiliacora triandra	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22418278]
NPO26573	Artemisia umbelliformis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO941	Tiliacora triandra	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28	Cutleria multifida	Species	Cutleriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4636	Onopordum anatolicum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3731	Salix japonica	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5560	Castor fiber	Species	Castoridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26573	Artemisia umbelliformis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28	Cutleria multifida	Species	Cutleriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO941	Tiliacora triandra	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26307	Viburnum ayavacense	Species	Adoxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6515	Juglans sinensis	Species	Juglandaceae	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	4

Activity Type	# Activity
Cell line	3
Non-molecular	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
NPT169	Cell line	B16-F10	Mus musculus	IC50	>	10000.0	nM	PMID[22305494]
NPT1171	Cell line	HEp-2	Homo sapiens	IC50	>	10000.0	nM	PMID[22305494]
NPT83	Cell line	MCF7	Homo sapiens	IC50	>	10000.0	nM	PMID[22305494]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	IC50	>	10000.0	nM	PMID[22305494]

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 NPC110139 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	19950
0.1-0.2	24499
0.2-0.3	4080
0.3-0.4	1026
0.4-0.5	205
0.5-0.6	57
0.6-0.7	24
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	Natural Product ID
1.0	High Similarity	NPC108709
0.7901	Intermediate Similarity	NPC68419
0.7875	Intermediate Similarity	NPC116794
0.7805	Intermediate Similarity	NPC271138
0.7805	Intermediate Similarity	NPC102914
0.75	Intermediate Similarity	NPC220984
0.7447	Intermediate Similarity	NPC134835
0.7386	Intermediate Similarity	NPC179434
0.6905	Remote Similarity	NPC605954
0.686	Remote Similarity	NPC7870
0.686	Remote Similarity	NPC310014
0.686	Remote Similarity	NPC269315
0.686	Remote Similarity	NPC75747
0.6667	Remote Similarity	NPC73318
0.6632	Remote Similarity	NPC475171
0.6552	Remote Similarity	NPC37739
0.6477	Remote Similarity	NPC212968
0.6437	Remote Similarity	NPC237503
0.64	Remote Similarity	NPC601659
0.6364	Remote Similarity	NPC199457
0.6329	Remote Similarity	NPC307335
0.6329	Remote Similarity	NPC74855
0.6292	Remote Similarity	NPC187056
0.6292	Remote Similarity	NPC137917
0.6292	Remote Similarity	NPC606216
0.6292	Remote Similarity	NPC607023
0.6263	Remote Similarity	NPC101744
0.6163	Remote Similarity	NPC191763
0.6136	Remote Similarity	NPC46388
0.6111	Remote Similarity	NPC604133
0.6023	Remote Similarity	NPC167383
0.6	Remote Similarity	NPC479080
0.5955	Remote Similarity	NPC285576
0.5833	Remote Similarity	NPC29069
0.5745	Remote Similarity	NPC256798
0.5729	Remote Similarity	NPC189884
0.5729	Remote Similarity	NPC90856
0.5729	Remote Similarity	NPC138334
0.5657	Remote Similarity	NPC139894
0.5652	Remote Similarity	NPC65590
0.5652	Remote Similarity	NPC125923
0.5652	Remote Similarity	NPC306746
0.5644	Remote Similarity	NPC473343
0.5625	Remote Similarity	NPC47063
0.56	Remote Similarity	NPC150400
0.5579	Remote Similarity	NPC128925
0.5567	Remote Similarity	NPC204458
0.5556	Remote Similarity	NPC40552
0.5446	Remote Similarity	NPC473373
0.5426	Remote Similarity	NPC64106
0.5408	Remote Similarity	NPC214484
0.5408	Remote Similarity	NPC269095
0.5376	Remote Similarity	NPC190837
0.5361	Remote Similarity	NPC209894
0.5354	Remote Similarity	NPC78046
0.5347	Remote Similarity	NPC235405
0.53	Remote Similarity	NPC475208
0.53	Remote Similarity	NPC48499
0.5294	Remote Similarity	NPC58448
0.5294	Remote Similarity	NPC249848
0.5294	Remote Similarity	NPC107966
0.5263	Remote Similarity	NPC48249
0.5243	Remote Similarity	NPC295371
0.5243	Remote Similarity	NPC473884
0.5243	Remote Similarity	NPC39211
0.5222	Remote Similarity	NPC171208
0.5217	Remote Similarity	NPC240125
0.5204	Remote Similarity	NPC607754
0.5196	Remote Similarity	NPC475516
0.5192	Remote Similarity	NPC161674
0.5192	Remote Similarity	NPC469946
0.5182	Remote Similarity	NPC481030
0.5143	Remote Similarity	NPC75417
0.514	Remote Similarity	NPC68175
0.514	Remote Similarity	NPC235438
0.51	Remote Similarity	NPC473481
0.5096	Remote Similarity	NPC157868
0.5094	Remote Similarity	NPC109588
0.5094	Remote Similarity	NPC30735
0.5094	Remote Similarity	NPC160415
0.5094	Remote Similarity	NPC309714
0.5093	Remote Similarity	NPC222580
0.5047	Remote Similarity	NPC40775
0.5047	Remote Similarity	NPC10607
0.5047	Remote Similarity	NPC11551
0.5047	Remote Similarity	NPC46665
0.5047	Remote Similarity	NPC480475
0.5045	Remote Similarity	NPC96641
0.5045	Remote Similarity	NPC163183

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC110139 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7115
0.1-0.2	1970
0.2-0.3	60
0.3-0.4	4
0.4-0.5	1
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