NPASS Compound

Natural Product: NPC21190

Natural Product ID	NPC21190
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Swertianolin
IUPAC Name	1,5-dihydroxy-3-methoxy-8-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyxanthen-9-one
Synonyms	swertianolin
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL468396
PubChem CID	5281662
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000123] Benzopyrans [CHEMONTID:0003410] 1-benzopyrans [CHEMONTID:0002817] Dibenzopyrans [CHEMONTID:0000200] Xanthenes [CHEMONTID:0000204] Xanthones

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 51 54 0 0 0 0 0 0 0 0999 V2000 -5.8625 0.8095 -2.9064 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.4700 0.8150 -2.7049 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1374 -0.0055 -1.4668 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.7734 0.0199 -1.2983 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3741 0.1065 0.0296 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.0009 -0.0393 0.0735 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3711 -1.0053 0.8089 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9702 -1.9597 1.5999 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1979 -2.8829 2.2939 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1685 -2.8609 2.2045 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8087 -1.9104 1.4145 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0310 -1.0153 0.7432 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6591 -0.0734 -0.0394 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9895 0.7782 -0.6818 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0496 -0.0804 -0.1070 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7726 -1.0156 0.5992 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1320 -1.8926 1.3307 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1652 -1.0105 0.5218 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7990 -0.0678 -0.2616 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0398 0.8558 -0.9566 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6685 0.8642 -0.8911 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8790 1.7713 -1.5714 O 0 0 0 0 0 0 0 0 0 0 0 0 7.1864 -0.0552 -0.3446 O 0 0 0 0 0 0 0 0 0 0 0 0 7.8147 0.9252 -1.1578 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9036 -3.7874 2.9031 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8208 1.5050 0.4808 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.3261 1.4067 0.6070 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.9458 0.4104 -0.3020 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.3816 -0.7348 0.4032 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.9275 2.6687 0.5228 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2658 1.8027 1.7187 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.2971 1.6198 -2.5861 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1131 1.8523 -2.6177 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0326 0.3741 -3.6174 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4138 -1.0614 -1.7302 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9772 -0.5987 0.6226 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0495 -1.9700 1.6649 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7248 -3.6033 2.8948 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7172 -1.7586 1.0881 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5173 1.6024 -1.5758 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6905 1.5698 -2.5494 H 0 0 0 0 0 0 0 0 0 0 0 0 7.4955 0.7280 -2.2066 H 0 0 0 0 0 0 0 0 0 0 0 0 8.9011 0.9024 -1.0864 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3899 1.9184 -0.8310 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1564 -4.6456 2.3903 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6005 2.2639 -0.2813 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5156 1.0676 1.6681 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9028 0.8668 -0.6952 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3495 -1.5415 -0.1356 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1927 3.3303 0.5838 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9410 2.7412 1.6825 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 8 9 1 0 9 10 2 0 10 11 1 0 11 12 2 0 12 13 1 0 13 14 2 0 13 15 1 0 15 16 2 0 16 17 1 0 16 18 1 0 18 19 2 0 19 20 1 0 20 21 2 0 21 22 1 0 19 23 1 0 23 24 1 0 10 25 1 0 5 26 1 0 26 27 1 0 27 28 1 0 28 29 1 0 27 30 1 0 26 31 1 0 28 3 1 0 12 7 1 0 21 15 1 0 17 11 1 0 1 32 1 0 2 33 1 0 2 34 1 0 3 35 1 6 5 36 1 1 8 37 1 0 9 38 1 0 18 39 1 0 20 40 1 0 22 41 1 0 24 42 1 0 24 43 1 0 24 44 1 0 25 45 1 0 26 46 1 6 27 47 1 1 28 48 1 6 29 49 1 0 30 50 1 0 31 51 1 0 M END

Standard InCHIKey	XMVBNLMKPMPWAX-DIKOWXHZSA-N
Standard InCHI	InChI=1S/C20H20O11/c1-28-7-4-9(23)13-11(5-7)29-19-8(22)2-3-10(14(19)16(13)25)30-20-18(27)17(26)15(24)12(6-21)31-20/h2-5,12,15,17-18,20-24,26-27H,6H2,1H3/t12-,15-,17+,18-,20-/m1/s1
SMILES	OC[C@H]1O[C@@H](Oc2ccc(c3c2c(=O)c2c(o3)cc(cc2O)OC)O)[C@@H]([C@H]([C@@H]1O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	436.1	Volume:	398.488 ? Van der Waals volume.
Dense:	1.094	LogP:	0.889 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.406 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.709 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	4.0	Rigid Bonds:	23.0
TPSA:	179.28 ? Topological Polar Surface Area.	H-Bond Acceptor:	11.0
H-Bond Donor:	6.0	Rings:	4.0
Heavy Atoms:	11.0

MedChem Properties

QED Drug-Likeness Score:	0.292	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	3.97	Fsp³:	0.35
MCE-18:	87.63 ? 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:	Rejected	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.632	Fluc inhibitor:	0.222 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.882 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.753 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.095	Promiscuous compounds:	0.43

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.215	MDCK Permeability:	-5.247
Pgp-inhibitor:	0.0	Pgp-substrate:	0.211
PAMPA:	0.968 ? 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):	0.956
20% Bioavailability (F20%):	0.287	30% Bioavailability (F30%):	0.994
50% Bioavailability (F50%):	0.991

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.164
Plasma Protein Binding (PPB):	78.911%	Volume Distribution (VD):	-0.017
Fu:	21.06% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.753
BSEP inhibitor:	0.009

ADMET: Metabolism

CYP1A2-inhibitor:	0.241	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.02	CYP2C19-substrate:	0.001
CYP2C9-inhibitor:	0.007	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.023
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.705
HLM stability:	0.256 ? 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):

3.006

Half-life (T1/2):

3.423

ADMET: Toxicity

hERG Blockers:	0.018	hERG Blockers (10um):	0.092
Human Hepatotoxicity (H-HT):	0.662	Drug-induced Liver Injury (DILI):	0.991
AMES Toxicity:	0.936	Rat Oral Acute Toxicity:	0.076
Maximum Recommended Daily Dose:	0.085	Skin Sensitization:	0.983
Carcinogencity:	0.59	Eye Corrosion:	0.0
Eye Irritation:	0.526	Respiratory Toxicity:	0.039
Drug-induced Neurotoxicity:	0.002	Ototoxicity:	0.744
Hematotoxicity:	0.28	Drug-induced Nephrotoxicity:	0.238
Genotoxicity:	0.868	RPMI-8226 Immunitoxicity:	0.076
A549 Cytotoxicity:	0.205	Hek293 Cytotoxicity:	0.243
BCF:	0.418 ? 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:	3.027 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.518 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.608 ? 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
NPO14535	Swertia fasciculata	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1002/cbdv.200490123]
NPO22457	Swertia calycina	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1002/cbdv.200490123]
NPO9389	Swertia bimaculata	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1002/cbdv.200490123]
NPO14238	Swertia punicea	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1002/cbdv.200490123]
NPO23023	Swertia pubescens	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1002/cbdv.200490123]
NPO26491	Swertia nervosa	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1002/cbdv.200490123]
NPO20502	Swertia cincta	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1002/cbdv.200490123]
NPO19705	Gentianella campestris	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1002/hlca.19750580731]
NPO28011	Swertia japonica	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1007/BF02675902]
NPO2355	Swertia macrosperma	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/0031-9422(89)80400-5]
NPO15376	Gentiana ramosa	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/S0031-9422(00)89285-7]
NPO22601	Gentiana germanica	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/S0031-9422(00)89285-7]
NPO9389	Swertia bimaculata	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/S0031-9422(00)98635-7]
NPO15592	Swertia punctata	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/S0031-9422(02)00231-5]
NPO30223	Swertia chirata	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/S0040-4039(00)72792-4]
NPO30223	Swertia chirata	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/S0040-4039(00)95355-3]
NPO14238	Swertia punicea	Species	Gentianaceae	Eukaryota	n.a.	whole plant	n.a.	DOI[10.1021/jo00025a032]
NPO14238	Swertia punicea	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1021/np50072a022]
NPO28011	Swertia japonica	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1055/s-2008-1074888]
NPO30223	Swertia chirata	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1248/cpb.30.4088]
NPO28011	Swertia japonica	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1248/cpb.30.4088]
NPO26420	Swertia perennis	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[1002/hlca.19760590517]
NPO28011	Swertia japonica	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10353265]
NPO21926	Pseudomonas aeruginosa	Species	Pseudomonadaceae	Bacteria	n.a.	n.a.	n.a.	PMID[10556916]
NPO403	Gentiana lutea	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10705751]
NPO19369	Bacillus thuringiensis	Species	Bacillaceae	Bacteria	n.a.	n.a.	n.a.	PMID[11087590]
NPO2743	Swertia purpurascens	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1133711]
NPO28502	Rhabdastrella globostellata	Species	Ancorinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[11858759]
NPO15592	Swertia punctata	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12377236]
NPO403	Gentiana lutea	Species	Gentianaceae	Eukaryota	n.a.	seed	n.a.	PMID[12822897]
NPO19705	Gentianella campestris	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15490334]
NPO28502	Rhabdastrella globostellata	Species	Ancorinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[16499318]
NPO28502	Rhabdastrella globostellata	Species	Ancorinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[16562838]
NPO28502	Rhabdastrella globostellata	Species	Ancorinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[17524651]
NPO403	Gentiana lutea	Species	Gentianaceae	Eukaryota	n.a.	root	n.a.	PMID[18064621]
NPO403	Gentiana lutea	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18064621]
NPO26770	Pteris multifida	Species	Pteridaceae	Eukaryota	Whole plant	n.a.	n.a.	PMID[18181575]
NPO32688	gentianella amarella ssp. acuta	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18336006]
NPO21926	Pseudomonas aeruginosa	Species	Pseudomonadaceae	Bacteria	n.a.	n.a.	n.a.	PMID[19406895]
NPO3494	Swietenia mahagoni	Species	Meliaceae	Eukaryota	fruits	n.a.	n.a.	PMID[19902967]
NPO21926	Pseudomonas aeruginosa	Species	Pseudomonadaceae	Bacteria	n.a.	n.a.	n.a.	PMID[19917748]
NPO28502	Rhabdastrella globostellata	Species	Ancorinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[20627740]
NPO14238	Swertia punicea	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20677781]
NPO28502	Rhabdastrella globostellata	Species	Ancorinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[20718449]
NPO21926	Pseudomonas aeruginosa	Species	Pseudomonadaceae	Bacteria	n.a.	n.a.	n.a.	PMID[20932054]
NPO2355	Swertia macrosperma	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[2239318]
NPO14077	Chamaecyparis lawsoniana	Species	Cupressaceae	Eukaryota	n.a.	stem	n.a.	PMID[23157017]
NPO14077	Chamaecyparis lawsoniana	Species	Cupressaceae	Eukaryota	n.a.	leaf	n.a.	PMID[23157017]
NPO9824	Swertia kouitchensis	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23805995]
NPO403	Gentiana lutea	Species	Gentianaceae	Eukaryota	n.a.	root	n.a.	PMID[24257774]
NPO11601	Chandonanthus hirtellus	Species	Anastrophyllaceae	Eukaryota	n.a.	Chinese liverworts	n.a.	PMID[24491225]
NPO21926	Pseudomonas aeruginosa	Species	Pseudomonadaceae	Bacteria	n.a.	n.a.	n.a.	PMID[25043228]
NPO21926	Pseudomonas aeruginosa	Species	Pseudomonadaceae	Bacteria	n.a.	n.a.	n.a.	PMID[25960261]
NPO28011	Swertia japonica	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26996316]
NPO13626	Aconitum karakolicum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Europe PMC[305622]
NPO21926	Pseudomonas aeruginosa	Species	Pseudomonadaceae	Bacteria	n.a.	n.a.	n.a.	PMID[32603106]
NPO14077	Chamaecyparis lawsoniana	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[37447036]
NPO14077	Chamaecyparis lawsoniana	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[38794396]
NPO26491	Swertia nervosa	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[4472648]
NPO2743	Swertia purpurascens	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[4527698]
NPO30223	Swertia chirata	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[4712626]
NPO28011	Swertia japonica	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[5583807]
NPO21926	Pseudomonas aeruginosa	Species	Pseudomonadaceae	Bacteria	n.a.	Antarctic	n.a.	PMID[8882433]
NPO26420	Swertia perennis	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[931752]
NPO23835	Swertia angustifolia	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[Article]
NPO15376	Gentiana ramosa	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[Article]
NPO19705	Gentianella campestris	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[Article]
NPO30223	Swertia chirata	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[Article]
NPO26491	Swertia nervosa	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[Article]
NPO13236	Viguiera multiflora	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21926	Pseudomonas aeruginosa	Species	Pseudomonadaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO403	Gentiana lutea	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22457	Swertia calycina	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3494	Swietenia mahagoni	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO23835	Swertia angustifolia	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19369	Bacillus thuringiensis	Species	Bacillaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28011	Swertia japonica	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15094	Coriaria myrtifolia	Species	Coriariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28502	Rhabdastrella globostellata	Species	Ancorinidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13626	Aconitum karakolicum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26770	Pteris multifida	Species	Pteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13329	Tephrosia polystachyoides	Species	Geometridae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20502	Swertia cincta	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14535	Swertia fasciculata	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2355	Swertia macrosperma	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26491	Swertia nervosa	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO23023	Swertia pubescens	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14238	Swertia punicea	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16170	Xerula longipes	Species	Physalacriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12294	Kydia calycina	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1890	Lidbeckia pectinata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26420	Swertia perennis	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7994	Derris laxiflora	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7868	Xeromphis obovata	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2743	Swertia purpurascens	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9389	Swertia bimaculata	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO30223	Swertia chirata	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14077	Chamaecyparis lawsoniana	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15801	Hunteria umbellata	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28996	Caloglossa leprieurii	Species	Delesseriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO32688	gentianella amarella ssp. acuta	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14630	Boronia ramosa	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14238	Swertia punicea	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2743	Swertia purpurascens	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8844	Stillingia sylvatica	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13626	Aconitum karakolicum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO30223	Swertia chirata	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28011	Swertia japonica	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2355	Swertia macrosperma	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14535	Swertia fasciculata	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO403	Gentiana lutea	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26420	Swertia perennis	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26491	Swertia nervosa	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23023	Swertia pubescens	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9824	Swertia kouitchensis	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23835	Swertia angustifolia	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15376	Gentiana ramosa	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22601	Gentiana germanica	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26770	Pteris multifida	Species	Pteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22457	Swertia calycina	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2756	Emerita analoga	Species	Hippidae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28996	Caloglossa leprieurii	Species	Delesseriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO20502	Swertia cincta	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26770	Pteris multifida	Species	Pteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23835	Swertia angustifolia	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26420	Swertia perennis	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28011	Swertia japonica	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO403	Gentiana lutea	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22457	Swertia calycina	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9824	Swertia kouitchensis	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8844	Stillingia sylvatica	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28996	Caloglossa leprieurii	Species	Delesseriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2743	Swertia purpurascens	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14535	Swertia fasciculata	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23023	Swertia pubescens	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26491	Swertia nervosa	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15094	Coriaria myrtifolia	Species	Coriariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13626	Aconitum karakolicum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2355	Swertia macrosperma	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14238	Swertia punicea	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20502	Swertia cincta	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19705	Gentianella campestris	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22601	Gentiana germanica	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15376	Gentiana ramosa	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2756	Emerita analoga	Species	Hippidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14238	Swertia punicea	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO13626	Aconitum karakolicum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO403	Gentiana lutea	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO23835	Swertia angustifolia	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO28011	Swertia japonica	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO22457	Swertia calycina	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO2355	Swertia macrosperma	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO30223	Swertia chirata	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO26420	Swertia perennis	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO403	Gentiana lutea	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO28011	Swertia japonica	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO27787	Pseudocentrotus depressus	Species	Echinidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15726	Rudbeckia subtomentosa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19369	Bacillus thuringiensis	Species	Bacillaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO26770	Pteris multifida	Species	Pteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9155	Kageneckia angustifolia	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13360	Passiflora racemosa	Species	Passifloraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21926	Pseudomonas aeruginosa	Species	Pseudomonadaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO15376	Gentiana ramosa	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16170	Xerula longipes	Species	Physalacriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2312	Encephalosphaera lasiandra	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15306	Smilax japonica	Species	Smilacaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15818	Lycianthes marlipoensis	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28502	Rhabdastrella globostellata	Species	Ancorinidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15094	Coriaria myrtifolia	Species	Coriariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15592	Swertia punctata	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9389	Swertia bimaculata	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1890	Lidbeckia pectinata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12517	Tylophora cordifolia	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8611	Cornutia grandifolia	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14077	Chamaecyparis lawsoniana	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7056	Pedinophyllum interruptum	Species	Plagiochilaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11601	Chandonanthus hirtellus	Species	Anastrophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28011	Swertia japonica	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7868	Xeromphis obovata	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO20502	Swertia cincta	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26420	Swertia perennis	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8844	Stillingia sylvatica	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3494	Swietenia mahagoni	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8866	Papaver atlanticum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23442	Cachonina hallii	Species	Heterocapsaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2756	Emerita analoga	Species	Hippidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22601	Gentiana germanica	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11567	Picradeniopsis absinthifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28996	Caloglossa leprieurii	Species	Delesseriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO403	Gentiana lutea	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12294	Kydia calycina	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19705	Gentianella campestris	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10624	Solidago wrightii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14630	Boronia ramosa	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2355	Swertia macrosperma	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29129	Rhodiola heterodonta	Species	Crassulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13626	Aconitum karakolicum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13236	Viguiera multiflora	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13329	Tephrosia polystachyoides	Species	Geometridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14238	Swertia punicea	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14940	Cedronella cana	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15801	Hunteria umbellata	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23835	Swertia angustifolia	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7994	Derris laxiflora	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16479	Tigridia pavonia	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22457	Swertia calycina	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2743	Swertia purpurascens	Species	Gentianaceae	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
Inhibition	3
IC50	2

Activity Type	# Activity
Individual protein	3
Others	1
Protein family	1

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT204	Individual protein	Acetylcholinesterase	Homo sapiens	Inhibition	=	9.8	%	PMID[18336006]
NPT261	Individual protein	Monoamine oxidase A	Homo sapiens	Inhibition	=	43.8	%	PMID[18336006]
NPT582	Individual protein	Monoamine oxidase B	Homo sapiens	Inhibition	=	93.6	%	PMID[18336006]

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified	n.a.	IC50	=	126000.0	nM	PMID[23805995]
NPT28736	Protein family	Alpha-glucosidase	Saccharomyces cerevisiae S288c	IC50	=	389000.0	nM	PMID[30282319]

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 NPC21190 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	22692
0.1-0.2	23073
0.2-0.3	2958
0.3-0.4	827
0.4-0.5	251
0.5-0.6	49
0.6-0.7	2
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC22195
0.7568	Intermediate Similarity	NPC112755
0.7568	Intermediate Similarity	NPC170675
0.6506	Remote Similarity	NPC267254
0.6087	Remote Similarity	NPC179947
0.5974	Remote Similarity	NPC191154
0.5783	Remote Similarity	NPC95090
0.5783	Remote Similarity	NPC27408
0.5747	Remote Similarity	NPC601586
0.5732	Remote Similarity	NPC183357
0.5714	Remote Similarity	NPC84362
0.5714	Remote Similarity	NPC73511
0.5698	Remote Similarity	NPC486578
0.5663	Remote Similarity	NPC95855
0.5632	Remote Similarity	NPC311830
0.5632	Remote Similarity	NPC607707
0.5604	Remote Similarity	NPC102028
0.5595	Remote Similarity	NPC277205
0.5595	Remote Similarity	NPC37919
0.5595	Remote Similarity	NPC323593
0.5595	Remote Similarity	NPC203500
0.5517	Remote Similarity	NPC22832
0.5517	Remote Similarity	NPC243930
0.55	Remote Similarity	NPC134819
0.5476	Remote Similarity	NPC289667
0.5476	Remote Similarity	NPC39360
0.5476	Remote Similarity	NPC44558
0.5476	Remote Similarity	NPC29763
0.5476	Remote Similarity	NPC210003
0.5465	Remote Similarity	NPC60966
0.5422	Remote Similarity	NPC93099
0.5412	Remote Similarity	NPC297987
0.5412	Remote Similarity	NPC136042
0.5412	Remote Similarity	NPC189142
0.5412	Remote Similarity	NPC77660
0.5402	Remote Similarity	NPC285197
0.5341	Remote Similarity	NPC601144
0.5301	Remote Similarity	NPC474434
0.5294	Remote Similarity	NPC210042
0.5294	Remote Similarity	NPC261866
0.5253	Remote Similarity	NPC473618
0.5233	Remote Similarity	NPC197896
0.5233	Remote Similarity	NPC313163
0.5233	Remote Similarity	NPC234739
0.5227	Remote Similarity	NPC307938
0.5172	Remote Similarity	NPC600680
0.5172	Remote Similarity	NPC610763
0.5111	Remote Similarity	NPC116458
0.5111	Remote Similarity	NPC246943
0.5111	Remote Similarity	NPC605784
0.5109	Remote Similarity	NPC239549
0.5059	Remote Similarity	NPC127415
0.5056	Remote Similarity	NPC479402
0.5056	Remote Similarity	NPC80140

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC21190 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5161
0.1-0.2	3896
0.2-0.3	77
0.3-0.4	12
0.4-0.5	4
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