NPASS Compound

Natural Product: NPC20302

Natural Product ID	NPC20302
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	ARTYOOFBEGPUAU-NSXHFEBNSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL2047407
PubChem CID	57328756
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001125] Steroid lactones [CHEMONTID:0001560] Withanolides 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 77 82 0 0 0 0 0 0 0 0999 V2000 9.3702 1.1439 -0.4541 C 0 0 0 0 0 0 0 0 0 0 0 0 8.1179 0.3838 -0.1010 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5540 0.6547 0.9846 O 0 0 0 0 0 0 0 0 0 0 0 0 7.5879 -0.5761 -0.9161 O 0 0 0 0 0 0 0 0 0 0 0 0 6.4342 -1.3208 -0.6541 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2778 -0.4335 -0.4889 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5870 -0.4153 0.6318 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9443 -1.3042 1.7894 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4657 0.5415 0.7364 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7081 0.8583 -0.4711 C 0 0 1 0 0 0 0 0 0 0 0 0 3.7088 1.2463 -1.4537 O 0 0 0 0 0 0 0 0 0 0 0 0 4.8462 0.4197 -1.5863 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5298 0.3858 -2.6490 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7901 -0.0356 -1.1285 C 0 0 2 0 0 0 0 0 0 0 0 0 0.5949 -0.6128 -0.5210 C 0 0 1 0 0 0 0 0 0 0 0 0 0.6886 -1.4849 0.6680 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5421 -1.1462 1.5362 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4627 -0.6546 0.4665 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.5510 0.3361 -0.2435 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.2333 1.4440 0.6824 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2756 0.7861 -1.4697 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5940 1.4190 -0.9948 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4703 0.3419 -0.4010 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.7580 -0.1279 0.8712 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.5993 -1.3152 1.3637 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8814 -0.7350 1.8441 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.5399 0.2494 1.0325 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.8778 0.7253 -0.2036 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.9736 2.2495 -0.3642 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6570 0.1723 -1.3638 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4411 0.6174 -2.5295 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.6654 -0.8677 -1.2126 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.3559 -0.9087 -0.0849 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.0398 0.1161 0.9336 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.7004 1.3047 0.7284 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.9639 0.5846 2.2501 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4930 -1.1894 -1.8690 C 0 0 0 0 0 0 0 0 0 0 0 0 9.7187 0.8091 -1.4466 H 0 0 0 0 0 0 0 0 0 0 0 0 10.0904 0.9914 0.3491 H 0 0 0 0 0 0 0 0 0 0 0 0 9.0564 2.2022 -0.5739 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2720 -2.0545 -1.4875 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5514 -1.9775 0.2530 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6678 -2.3414 1.4360 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2358 -1.0765 2.5988 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9879 -1.2705 2.0747 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0187 1.5211 0.9909 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8750 0.4088 1.6711 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2123 1.8645 -0.2878 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3856 0.5640 -2.0171 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1505 -1.2654 -1.3424 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5012 -2.5825 0.4217 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6053 -1.5090 1.2354 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9173 -2.0364 2.0664 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3061 -0.3289 2.2278 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6108 -1.4938 -0.2545 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1031 2.3801 0.0616 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1046 1.7141 1.3534 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6013 1.2769 1.3738 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5632 -0.1152 -2.0504 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7059 1.4940 -2.0874 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2865 2.1727 -0.2404 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0493 1.8994 -1.8846 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3763 -0.5389 -1.1041 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7909 0.6125 1.6608 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7439 -2.0467 0.5351 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0432 -1.8232 2.1669 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4796 -1.4241 2.4822 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9382 2.6422 -0.0029 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1855 2.7776 0.1684 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9541 2.4840 -1.4631 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8627 -1.5977 -1.9863 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.1029 -1.6782 0.0295 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3944 -0.2688 1.9308 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.1777 1.2771 -0.1502 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0954 -0.8500 -2.7093 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6282 -1.7433 -2.3606 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9265 -1.9220 -1.1934 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 2 0 2 4 1 0 4 5 1 0 5 6 1 0 6 7 2 0 7 8 1 0 7 9 1 0 9 10 1 0 10 11 1 0 11 12 1 0 12 13 2 0 10 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 1 19 21 1 0 21 22 1 0 22 23 1 0 23 24 1 0 24 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 2 0 30 32 1 0 32 33 2 0 33 34 1 0 34 35 1 0 27 36 1 1 14 37 1 0 12 6 1 0 19 15 1 0 28 23 1 0 24 18 1 0 36 26 1 0 34 27 1 0 1 38 1 0 1 39 1 0 1 40 1 0 5 41 1 0 5 42 1 0 8 43 1 0 8 44 1 0 8 45 1 0 9 46 1 0 9 47 1 0 10 48 1 1 14 49 1 6 15 50 1 6 16 51 1 0 16 52 1 0 17 53 1 0 17 54 1 0 18 55 1 6 20 56 1 0 20 57 1 0 20 58 1 0 21 59 1 0 21 60 1 0 22 61 1 0 22 62 1 0 23 63 1 6 24 64 1 1 25 65 1 0 25 66 1 0 26 67 1 1 29 68 1 0 29 69 1 0 29 70 1 0 32 71 1 0 33 72 1 0 34 73 1 1 35 74 1 0 37 75 1 0 37 76 1 0 37 77 1 0 M END

Standard InCHIKey	ARTYOOFBEGPUAU-NSXHFEBNSA-N
Standard InCHI	InChI=1S/C30H40O7/c1-15-12-23(36-27(34)19(15)14-35-17(3)31)16(2)20-6-7-21-18-13-26-30(37-26)25(33)9-8-24(32)29(30,5)22(18)10-11-28(20,21)4/h8-9,16,18,20-23,25-26,33H,6-7,10-14H2,1-5H3/t16-,18-,20+,21-,22-,23+,25-,26+,28+,29-,30+/m0/s1
SMILES	CC(=O)OCC1=C(C)C[C@@H](OC1=O)[C@H]([C@H]1CC[C@@H]2[C@]1(C)CC[C@H]1[C@H]2C[C@@H]2[C@]3([C@]1(C)C(=O)C=C[C@@H]3O)O2)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	512.28	Volume:	524.447 ? Van der Waals volume.
Dense:	0.977	LogP:	3.115 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.324 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.519 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	5.0	Rigid Bonds:	31.0
TPSA:	102.43 ? Topological Polar Surface Area.	H-Bond Acceptor:	7.0
H-Bond Donor:	1.0	Rings:	6.0
Heavy Atoms:	7.0

MedChem Properties

QED Drug-Likeness Score:	0.45	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.723	Fsp³:	0.767
MCE-18:	144.151 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Rejected	GSK Rule:	Accepted
Golden Triangle Rule:	Accepted	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.759	Fluc inhibitor:	0.066 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.011 ? 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:	0.139	Promiscuous compounds:	0.585

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.188	MDCK Permeability:	-4.989
Pgp-inhibitor:	0.993	Pgp-substrate:	0.012
PAMPA:	0.008 ? 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):	0.003
20% Bioavailability (F20%):	0.199	30% Bioavailability (F30%):	0.958
50% Bioavailability (F50%):	0.989

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.01	MRP1:	0.299
Plasma Protein Binding (PPB):	88.15%	Volume Distribution (VD):	-0.495
Fu:	9.914% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.056
BSEP inhibitor:	0.997

ADMET: Metabolism

CYP1A2-inhibitor:	0.026	CYP1A2-substrate:	0.001
CYP2C19-inhibitor:	0.722	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.006	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.037	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.998 ? 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):

9.794

Half-life (T1/2):

1.109

ADMET: Toxicity

hERG Blockers:	0.065	hERG Blockers (10um):	0.235
Human Hepatotoxicity (H-HT):	0.282	Drug-induced Liver Injury (DILI):	0.909
AMES Toxicity:	0.902	Rat Oral Acute Toxicity:	0.38
Maximum Recommended Daily Dose:	0.803	Skin Sensitization:	0.999
Carcinogencity:	0.991	Eye Corrosion:	0.014
Eye Irritation:	0.553	Respiratory Toxicity:	0.778
Drug-induced Neurotoxicity:	0.114	Ototoxicity:	0.237
Hematotoxicity:	0.586	Drug-induced Nephrotoxicity:	0.909
Genotoxicity:	0.853	RPMI-8226 Immunitoxicity:	0.191
A549 Cytotoxicity:	0.089	Hek293 Cytotoxicity:	0.639
BCF:	1.177 ? 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:	4.3 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.923 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.489 ? 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
NPO20281	Withania aristata	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22705001]
NPO20281	Withania aristata	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20281	Withania aristata	Species	Solanaceae	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
FC	1
IC50	30
Ratio IC50	1
Inhibition	1

Activity Type	# Activity
Individual protein	2
Cell line	24
Single protein	1
Unchecked	2
Protein complex group	1
Non-molecular	3

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT28317	Single protein	ATP-dependent Clp protease ATP-binding subunit clpX-like, mitochondrial	Homo sapiens	IC50	=	9500.0	nM	PMID[31550150]
NPT4582	Individual protein	Transitional endoplasmic reticulum ATPase	Homo sapiens	IC50	=	22000.0	nM	PMID[31550150]
NPT4377	Individual protein	Heat shock 70 kDa protein 6	Homo sapiens	FC	=	3.81	n.a.	PMID[19738026]
NPT29671	Protein complex group	Nuclear factor NF-kappa-B complex	Homo sapiens	IC50	=	70.0	nM	PMID[34445874]

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT165	Cell line	HeLa	Homo sapiens	IC50	=	7700.0	nM	PubChem BioAssay data set
NPT81	Cell line	A549	Homo sapiens	IC50	=	6700.0	nM	PMID[21458999]
NPT165	Cell line	HeLa	Homo sapiens	IC50	=	4700.0	nM	PubChem BioAssay data set
NPT81	Cell line	A549	Homo sapiens	IC50	=	4400.0	nM	PMID[18809939]
NPT83	Cell line	MCF7	Homo sapiens	IC50	=	5300.0	nM	PMID[24144848]
NPT83	Cell line	MCF7	Homo sapiens	IC50	=	2000.0	nM	PMID[25682561]
NPT189	Cell line	Vero	Chlorocebus aethiops	IC50	=	11400.0	nM	DrugMatrix in vivo data: Pathology
NPT189	Cell line	Vero	Chlorocebus aethiops	IC50	=	8500.0	nM	PMID[26034885]
NPT189	Cell line	Vero	Chlorocebus aethiops	Ratio IC50	=	2.2	n.a.	DrugMatrix in vitro pharmacology data
NPT165	Cell line	HeLa	Homo sapiens	IC50	=	10200.0	nM	PMID[28923386]
NPT83	Cell line	MCF7	Homo sapiens	IC50	=	4600.0	nM	PMID[28923386]
NPT189	Cell line	Vero	Chlorocebus aethiops	IC50	=	5900.0	nM	PMID[28923386]
NPT858	Cell line	LNCaP	Homo sapiens	IC50	=	1900.0	nM	PMID[38414352]
NPT389	Cell line	RPMI-8226	Homo sapiens	IC50	=	212.0	nM	PMID[34445874]
NPT389	Cell line	RPMI-8226	Homo sapiens	IC50	=	1510.0	nM	PMID[34445874]
NPT859	Cell line	HFF	Homo sapiens	IC50	=	1900.0	nM	PMID[38414352]
NPT90	Cell line	DU-145	Homo sapiens	IC50	=	800.0	nM	PMID[38414352]
NPT306	Cell line	PC-3	Homo sapiens	IC50	=	300.0	nM	PMID[38414352]
NPT28438	Unchecked	Unchecked	n.a.	IC50	=	107.0	nM	PMID[34445874]
NPT28438	Unchecked	Unchecked	n.a.	IC50	=	1400.0	nM	PMID[38414352]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	IC50	=	250.0	nM	PMID[24625088]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	Inhibition	>	80.0	%	PMID[24625088]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	IC50	=	230.0	nM	PMID[24625088]
NPT25439	Cell line	MM1.S	Homo sapiens	IC50	=	114.0	nM	PMID[34445874]

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 NPC20302 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	18266
0.1-0.2	25949
0.2-0.3	5438
0.3-0.4	123
0.4-0.5	32
0.5-0.6	28
0.6-0.7	10
0.7-0.8	0
0.8-0.85	4
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8592	High Similarity	NPC470494
0.8235	Intermediate Similarity	NPC286528
0.8133	Intermediate Similarity	NPC3381
0.8	Intermediate Similarity	NPC140055
0.8	Intermediate Similarity	NPC167606
0.7531	Intermediate Similarity	NPC231240
0.7333	Intermediate Similarity	NPC251226
0.6892	Remote Similarity	NPC50774
0.6842	Remote Similarity	NPC474370
0.68	Remote Similarity	NPC709
0.6703	Remote Similarity	NPC316915
0.6203	Remote Similarity	NPC183580
0.6203	Remote Similarity	NPC470495
0.6154	Remote Similarity	NPC470265
0.6076	Remote Similarity	NPC609580
0.6049	Remote Similarity	NPC312824
0.6	Remote Similarity	NPC88326
0.5949	Remote Similarity	NPC122056
0.5897	Remote Similarity	NPC243065
0.5854	Remote Similarity	NPC264954
0.5833	Remote Similarity	NPC23786
0.5802	Remote Similarity	NPC470493
0.575	Remote Similarity	NPC284915
0.575	Remote Similarity	NPC268530
0.5679	Remote Similarity	NPC154491
0.5679	Remote Similarity	NPC473274
0.5663	Remote Similarity	NPC600975
0.5663	Remote Similarity	NPC602010
0.5556	Remote Similarity	NPC270929
0.5556	Remote Similarity	NPC30923
0.5556	Remote Similarity	NPC610236
0.5542	Remote Similarity	NPC153700
0.5476	Remote Similarity	NPC8369
0.5476	Remote Similarity	NPC67569
0.5476	Remote Similarity	NPC608655
0.5465	Remote Similarity	NPC473593
0.5422	Remote Similarity	NPC159456
0.5422	Remote Similarity	NPC470878
0.5412	Remote Similarity	NPC609769
0.5412	Remote Similarity	NPC610140
0.5349	Remote Similarity	NPC606886
0.5294	Remote Similarity	NPC470492
0.5238	Remote Similarity	NPC61520
0.5227	Remote Similarity	NPC120994
0.5176	Remote Similarity	NPC473253

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC20302 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6299
0.1-0.2	2661
0.2-0.3	188
0.3-0.4	1
0.4-0.5	0
0.5-0.6	0
0.6-0.7	0
0.7-0.8	0
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
0.8	Intermediate Similarity	NPD7115	Discovery

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