NPASS Compound

Natural Product: NPC237503

Natural Product ID	NPC237503
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Hederagenin 28-O-Beta-D-Glucopyranosyl Ester
IUPAC Name	[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] (4aS,6aR,6aS,6bR,8aR,9R,10S,12aR,14bS)-10-hydroxy-9-(hydroxymethyl)-2,2,6a,6b,9,12a-hexamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylate
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL1910843
PubChem CID	21120798
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 103108 0 0 0 0 0 0 0 0999 V2000 9.8966 1.7537 -0.4736 O 0 0 0 0 0 0 0 0 0 0 0 0 8.9628 0.7713 -0.1672 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5789 1.3468 -0.3889 C 0 0 1 0 0 0 0 0 0 0 0 0 6.5873 0.4195 -0.1009 O 0 0 0 0 0 0 0 0 0 0 0 0 5.3686 0.7924 -0.6078 C 0 0 1 0 0 0 0 0 0 0 0 0 4.2854 0.2425 0.1557 O 0 0 0 0 0 0 0 0 0 0 0 0 3.2620 -0.4290 -0.4856 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3417 -0.5235 -1.7399 O 0 0 0 0 0 0 0 0 0 0 0 0 2.0958 -1.0253 0.2799 C 0 0 2 0 0 0 0 0 0 0 0 0 2.7935 -2.0309 1.2090 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2705 -3.2188 0.3862 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9717 -3.9144 -0.0048 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2298 -3.0524 -0.9467 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1705 -1.5915 -0.6904 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.2732 -1.1582 -0.5694 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0870 -1.6153 -1.5170 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5354 -1.2951 -1.5622 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9877 -0.5137 -0.3308 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.9619 0.5056 -0.0411 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.7506 -0.2748 0.5252 C 0 0 2 0 0 0 0 0 0 0 0 0 0.3325 0.7120 0.8197 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6063 0.0517 1.1969 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1238 -1.1108 1.6950 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4015 1.2355 -1.2339 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3889 1.5691 0.9462 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7077 2.1245 0.3784 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6877 1.0085 0.5389 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.4043 -0.1045 -0.4249 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.8757 0.1260 -1.8137 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3055 -1.2383 0.1072 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7482 -0.8917 0.0276 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.1437 0.4400 0.5074 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.0996 1.4861 0.5875 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.2951 2.5919 -0.4554 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2628 2.1767 1.9526 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.5528 2.6665 2.1125 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.1674 0.9195 -0.3481 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2031 -4.3454 1.2207 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3615 -5.2065 -0.7349 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2340 2.3096 -0.4140 C 0 0 1 0 0 0 0 0 0 0 0 0 6.0040 2.7671 0.8068 C 0 0 2 0 0 0 0 0 0 0 0 0 7.4790 2.5884 0.4880 C 0 0 2 0 0 0 0 0 0 0 0 0 7.8925 3.7338 -0.1848 O 0 0 0 0 0 0 0 0 0 0 0 0 5.6336 2.0159 1.9199 O 0 0 0 0 0 0 0 0 0 0 0 0 5.6119 3.0181 -1.5282 O 0 0 0 0 0 0 0 0 0 0 0 0 9.5214 2.3361 -1.1782 H 0 0 0 0 0 0 0 0 0 0 0 0 9.0876 -0.0895 -0.8437 H 0 0 0 0 0 0 0 0 0 0 0 0 9.1035 0.4240 0.8698 H 0 0 0 0 0 0 0 0 0 0 0 0 7.5041 1.6496 -1.4551 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2340 0.5919 -1.6805 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6791 -1.5083 1.6124 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1239 -2.4156 1.9852 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9234 -3.8386 0.9997 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7469 -2.8547 -0.5544 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6064 -3.3117 -1.9859 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1770 -3.4816 -0.9819 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4335 -1.1241 -1.7094 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7285 -2.2484 -2.3124 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0870 -2.2560 -1.6591 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7630 -0.6146 -2.4357 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9381 -1.2826 0.4999 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0151 1.3271 1.7123 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5127 1.4170 0.0170 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3780 0.8682 1.3077 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4826 -0.3067 2.2640 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3412 -1.1797 2.4829 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0305 -0.7322 2.2385 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3707 -2.1610 1.4323 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0646 1.3639 -2.0781 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4712 0.7629 -1.6392 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0695 2.2734 -0.9384 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6223 1.1953 1.9382 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6485 2.3888 0.9113 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4658 2.3208 -0.7087 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9984 3.0604 0.8453 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4922 0.5637 1.5642 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3588 0.8533 -2.4206 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9533 0.3722 -1.8723 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7844 -0.8637 -2.3533 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9579 -1.4986 1.1289 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1299 -2.1292 -0.5330 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0967 -1.0789 -1.0322 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2882 -1.7060 0.6001 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.6939 0.3063 1.4887 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4268 2.6075 -1.1764 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2563 2.4834 -0.9955 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3045 3.5960 -0.0009 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5800 3.0094 2.1041 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0934 1.4499 2.7801 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5750 3.6575 2.0029 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.7326 1.5771 0.0878 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5172 -3.6050 1.6239 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9811 -4.5461 2.0133 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7293 -5.3404 1.0446 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5042 -5.4786 -1.3833 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2319 -5.0439 -1.4030 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5132 -6.0416 -0.0341 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1566 2.5812 -0.2154 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7552 3.8162 0.9884 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0214 2.4380 1.4434 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1983 4.4638 -0.1515 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5928 2.5723 2.7521 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1795 2.5780 -2.3200 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 6 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 1 19 24 1 6 19 25 1 0 25 26 1 0 26 27 1 0 27 28 1 0 28 29 1 6 28 30 1 0 30 31 1 0 31 32 1 0 32 33 1 0 33 34 1 6 33 35 1 0 35 36 1 0 32 37 1 0 12 38 1 0 12 39 1 0 5 40 1 0 40 41 1 0 41 42 1 0 42 43 1 0 41 44 1 0 40 45 1 0 42 3 1 0 22 9 1 0 33 27 1 0 14 9 1 0 20 15 1 0 28 18 1 0 1 46 1 0 2 47 1 0 2 48 1 0 3 49 1 6 5 50 1 6 10 51 1 0 10 52 1 0 11 53 1 0 11 54 1 0 13 55 1 0 13 56 1 0 14 57 1 6 16 58 1 0 17 59 1 0 17 60 1 0 18 61 1 1 21 62 1 0 21 63 1 0 22 64 1 0 22 65 1 0 23 66 1 0 23 67 1 0 23 68 1 0 24 69 1 0 24 70 1 0 24 71 1 0 25 72 1 0 25 73 1 0 26 74 1 0 26 75 1 0 27 76 1 1 29 77 1 0 29 78 1 0 29 79 1 0 30 80 1 0 30 81 1 0 31 82 1 0 31 83 1 0 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 38 93 1 0 38 94 1 0 39 95 1 0 39 96 1 0 39 97 1 0 40 98 1 1 41 99 1 1 42100 1 1 43101 1 0 44102 1 0 45103 1 0 M END

Standard InCHIKey	WJMMBVSOQPALFO-DLQTVUGOSA-N
Standard InCHI	InChI=1S/C36H58O9/c1-31(2)13-15-36(30(43)45-29-28(42)27(41)26(40)22(18-37)44-29)16-14-34(5)20(21(36)17-31)7-8-24-32(3)11-10-25(39)33(4,19-38)23(32)9-12-35(24,34)6/h7,21-29,37-42H,8-19H2,1-6H3/t21-,22+,23+,24+,25-,26+,27-,28+,29-,32-,33-,34+,35+,36-/m0/s1
SMILES	OC[C@H]1O[C@@H](OC(=O)[C@@]23CCC(C[C@H]3C3=CC[C@H]4[C@@]([C@@]3(CC2)C)(C)CC[C@@H]2[C@]4(C)CC[C@@H]([C@@]2(C)CO)O)(C)C)[C@@H]([C@H]([C@@H]1O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	634.41	Volume:	653.712 ? Van der Waals volume.
Dense:	0.97	LogP:	2.874 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.979 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.598 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	5.0	Rigid Bonds:	33.0
TPSA:	156.91 ? Topological Polar Surface Area.	H-Bond Acceptor:	9.0
H-Bond Donor:	6.0	Rings:	6.0
Heavy Atoms:	9.0

MedChem Properties

QED Drug-Likeness Score:	0.201	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.321	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:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.934	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.013 ? 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:	0.19	Promiscuous compounds:	0.056

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.87	MDCK Permeability:	-5.236
Pgp-inhibitor:	0.002	Pgp-substrate:	0.002
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):	0.187
20% Bioavailability (F20%):	0.965	30% Bioavailability (F30%):	0.944
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.92	MRP1:	0.068
Plasma Protein Binding (PPB):	75.016%	Volume Distribution (VD):	-0.381
Fu:	18.589% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.809	BCRP inhibitor:	0.264
BSEP inhibitor:	0.529

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.197	CYP2C19-substrate:	0.006
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.005	CYP3A4-substrate:	0.004
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.606
HLM stability:	0.144 ? 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):

1.317

Half-life (T1/2):

2.231

ADMET: Toxicity

hERG Blockers:	0.014	hERG Blockers (10um):	0.032
Human Hepatotoxicity (H-HT):	0.724	Drug-induced Liver Injury (DILI):	0.484
AMES Toxicity:	0.727	Rat Oral Acute Toxicity:	0.061
Maximum Recommended Daily Dose:	0.063	Skin Sensitization:	0.999
Carcinogencity:	0.679	Eye Corrosion:	0.0
Eye Irritation:	0.012	Respiratory Toxicity:	0.087
Drug-induced Neurotoxicity:	0.005	Ototoxicity:	0.974
Hematotoxicity:	0.547	Drug-induced Nephrotoxicity:	0.942
Genotoxicity:	0.366	RPMI-8226 Immunitoxicity:	0.087
A549 Cytotoxicity:	0.794	Hek293 Cytotoxicity:	0.281
BCF:	1.527 ? 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:	3.848 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.532 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.693 ? 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]
NPO30412	Kalopanax pictus	Species	Araliaceae	Eukaryota	stem bark	Purchased from an herbal market at Kumsan, Chungnam, Korea	2009-AUG	PMID[21870831]
NPO30412	Kalopanax pictus	Species	Araliaceae	Eukaryota	n.a.	stem	n.a.	PMID[21870831]
NPO941	Tiliacora triandra	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22418278]
NPO28	Cutleria multifida	Species	Cutleriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO941	Tiliacora triandra	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO30412	Kalopanax pictus	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26573	Artemisia umbelliformis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
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]
NPO4636	Onopordum anatolicum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO941	Tiliacora triandra	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28	Cutleria multifida	Species	Cutleriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26573	Artemisia umbelliformis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5560	Castor fiber	Species	Castoridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3731	Salix japonica	Species	Salicaceae	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	2

Activity Type	# Activity
Individual protein	1
Others	1

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT677	Individual protein	Coagulation factor III	Homo sapiens	IC50	=	0.28	nM	PMID[28109788]

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified	n.a.	IC50	=	9100.0	nM	PMID[21870831]

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 NPC237503 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	20508
0.1-0.2	23448
0.2-0.3	4443
0.3-0.4	964
0.4-0.5	303
0.5-0.6	114
0.6-0.7	56
0.7-0.8	0
0.8-0.85	1
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8904	High Similarity	NPC167383
0.8861	High Similarity	NPC29069
0.8077	Intermediate Similarity	NPC306746
0.7848	Intermediate Similarity	NPC37739
0.7531	Intermediate Similarity	NPC137917
0.7363	Intermediate Similarity	NPC102439
0.7317	Intermediate Similarity	NPC68419
0.7209	Intermediate Similarity	NPC214484
0.7195	Intermediate Similarity	NPC199457
0.7079	Intermediate Similarity	NPC235405
0.7045	Intermediate Similarity	NPC48499
0.7	Intermediate Similarity	NPC191763
0.7	Intermediate Similarity	NPC249848
0.7	Intermediate Similarity	NPC107966
0.6977	Remote Similarity	NPC209894
0.6951	Remote Similarity	NPC46388
0.6923	Remote Similarity	NPC295371
0.6923	Remote Similarity	NPC473884
0.6889	Remote Similarity	NPC475516
0.6813	Remote Similarity	NPC150400
0.6809	Remote Similarity	NPC473459
0.6739	Remote Similarity	NPC39211
0.6739	Remote Similarity	NPC157868
0.6706	Remote Similarity	NPC604133
0.6702	Remote Similarity	NPC104071
0.6702	Remote Similarity	NPC30735
0.6667	Remote Similarity	NPC469946
0.6632	Remote Similarity	NPC40775
0.6629	Remote Similarity	NPC90856
0.6596	Remote Similarity	NPC192791
0.6596	Remote Similarity	NPC223301
0.6596	Remote Similarity	NPC242840
0.6596	Remote Similarity	NPC171544
0.6596	Remote Similarity	NPC112352
0.6562	Remote Similarity	NPC235438
0.6471	Remote Similarity	NPC116794
0.6471	Remote Similarity	NPC190837
0.6458	Remote Similarity	NPC10607
0.6458	Remote Similarity	NPC251768
0.6458	Remote Similarity	NPC159309
0.6458	Remote Similarity	NPC46665
0.6458	Remote Similarity	NPC86222
0.6452	Remote Similarity	NPC473373
0.6437	Remote Similarity	NPC271138
0.6437	Remote Similarity	NPC110139
0.6437	Remote Similarity	NPC108709
0.64	Remote Similarity	NPC246708
0.6392	Remote Similarity	NPC475591
0.6392	Remote Similarity	NPC63159
0.6392	Remote Similarity	NPC236870
0.6364	Remote Similarity	NPC281148
0.6327	Remote Similarity	NPC222580
0.6327	Remote Similarity	NPC297263
0.625	Remote Similarity	NPC102914
0.62	Remote Similarity	NPC104372
0.62	Remote Similarity	NPC114484
0.618	Remote Similarity	NPC220984
0.617	Remote Similarity	NPC139894
0.6146	Remote Similarity	NPC473343
0.6139	Remote Similarity	NPC301449
0.6139	Remote Similarity	NPC601290
0.6081	Remote Similarity	NPC196753
0.6078	Remote Similarity	NPC481030
0.6078	Remote Similarity	NPC80986
0.602	Remote Similarity	NPC109588
0.602	Remote Similarity	NPC309714
0.6019	Remote Similarity	NPC31838
0.6019	Remote Similarity	NPC481078
0.6019	Remote Similarity	NPC187290
0.6	Remote Similarity	NPC609763
0.5977	Remote Similarity	NPC605954
0.5957	Remote Similarity	NPC475208
0.5955	Remote Similarity	NPC310014
0.5955	Remote Similarity	NPC269315
0.5934	Remote Similarity	NPC256798
0.5926	Remote Similarity	NPC100639
0.5922	Remote Similarity	NPC241909
0.5914	Remote Similarity	NPC189884
0.5914	Remote Similarity	NPC138334
0.5851	Remote Similarity	NPC1046
0.5842	Remote Similarity	NPC475504
0.5833	Remote Similarity	NPC135904
0.5825	Remote Similarity	NPC481079
0.5806	Remote Similarity	NPC47063
0.58	Remote Similarity	NPC101744
0.58	Remote Similarity	NPC305267
0.58	Remote Similarity	NPC11551
0.58	Remote Similarity	NPC480475
0.5794	Remote Similarity	NPC79643
0.578	Remote Similarity	NPC475160
0.578	Remote Similarity	NPC470218
0.578	Remote Similarity	NPC473714
0.5778	Remote Similarity	NPC7870
0.5778	Remote Similarity	NPC75747
0.5778	Remote Similarity	NPC48249
0.5769	Remote Similarity	NPC295823
0.5769	Remote Similarity	NPC174720
0.5769	Remote Similarity	NPC475467
0.5761	Remote Similarity	NPC128925
0.5745	Remote Similarity	NPC204458
0.5741	Remote Similarity	NPC481031
0.5701	Remote Similarity	NPC76972
0.5701	Remote Similarity	NPC469782
0.5701	Remote Similarity	NPC204414
0.5688	Remote Similarity	NPC123199
0.5676	Remote Similarity	NPC481080
0.566	Remote Similarity	NPC75287
0.5658	Remote Similarity	NPC101475
0.5657	Remote Similarity	NPC475171
0.5648	Remote Similarity	NPC192600
0.5625	Remote Similarity	NPC476068
0.5625	Remote Similarity	NPC213412
0.5625	Remote Similarity	NPC179434
0.5619	Remote Similarity	NPC96641
0.5619	Remote Similarity	NPC163183
0.5619	Remote Similarity	NPC480474
0.5614	Remote Similarity	NPC65105
0.5579	Remote Similarity	NPC269095
0.5556	Remote Similarity	NPC60557
0.5556	Remote Similarity	NPC67857
0.5545	Remote Similarity	NPC155410
0.5534	Remote Similarity	NPC31193
0.5526	Remote Similarity	NPC41061
0.5526	Remote Similarity	NPC227551
0.5526	Remote Similarity	NPC258617
0.5521	Remote Similarity	NPC78046
0.5517	Remote Similarity	NPC298034
0.5517	Remote Similarity	NPC71065
0.5513	Remote Similarity	NPC230295
0.5513	Remote Similarity	NPC98386
0.5478	Remote Similarity	NPC293330
0.5478	Remote Similarity	NPC43550
0.5472	Remote Similarity	NPC480473
0.5472	Remote Similarity	NPC69811
0.5455	Remote Similarity	NPC58448
0.5455	Remote Similarity	NPC475899
0.5446	Remote Similarity	NPC75417
0.5431	Remote Similarity	NPC305981
0.5431	Remote Similarity	NPC481081
0.5413	Remote Similarity	NPC475287
0.5385	Remote Similarity	NPC235341
0.5385	Remote Similarity	NPC261506
0.5385	Remote Similarity	NPC4328
0.5351	Remote Similarity	NPC57484
0.5347	Remote Similarity	NPC263756
0.5347	Remote Similarity	NPC213674
0.5333	Remote Similarity	NPC64715
0.531	Remote Similarity	NPC488560
0.5269	Remote Similarity	NPC187056
0.5269	Remote Similarity	NPC212968
0.5269	Remote Similarity	NPC606216
0.5269	Remote Similarity	NPC607023
0.5263	Remote Similarity	NPC290598
0.5263	Remote Similarity	NPC30590
0.5258	Remote Similarity	NPC238935
0.525	Remote Similarity	NPC250247
0.5244	Remote Similarity	NPC136313
0.5243	Remote Similarity	NPC160415
0.5221	Remote Similarity	NPC471550
0.5221	Remote Similarity	NPC191827
0.5196	Remote Similarity	NPC471547
0.5196	Remote Similarity	NPC161674
0.5196	Remote Similarity	NPC76497
0.5192	Remote Similarity	NPC164389
0.5181	Remote Similarity	NPC481361
0.5169	Remote Similarity	NPC202828
0.5169	Remote Similarity	NPC119592
0.5143	Remote Similarity	NPC148417
0.5143	Remote Similarity	NPC68175
0.5135	Remote Similarity	NPC300419
0.5125	Remote Similarity	NPC53744
0.5122	Remote Similarity	NPC162107
0.5122	Remote Similarity	NPC46912
0.5096	Remote Similarity	NPC471548
0.5091	Remote Similarity	NPC11242
0.5091	Remote Similarity	NPC815
0.5062	Remote Similarity	NPC267517
0.506	Remote Similarity	NPC191965
0.5054	Remote Similarity	NPC204407
0.5048	Remote Similarity	NPC473401
0.5043	Remote Similarity	NPC25663
0.5042	Remote Similarity	NPC135849
0.5042	Remote Similarity	NPC236638
0.5042	Remote Similarity	NPC294453

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC237503 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7329
0.1-0.2	1745
0.2-0.3	70
0.3-0.4	5
0.4-0.5	0
0.5-0.6	1
0.6-0.7	0
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.575	Remote Similarity	NPD7645	Phase 2

Bioactivity similarity

Similar Natural Products in NPASS

Similarity level is defined by Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.
Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data