NPASS Compound

Natural Product: NPC5292

Natural Product ID	NPC5292
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	RGHQRULWHKEQHE-GRVQADPTSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL3605564
PubChem CID	NA
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 78 82 0 0 0 0 0 0 0 0999 V2000 -0.5074 -5.5410 -1.2497 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0647 -4.6758 -0.1858 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6934 -5.1209 0.8078 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0990 -3.3203 -0.2886 O 0 0 0 0 0 0 0 0 0 0 0 0 0.4216 -2.4064 0.6953 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0487 -0.9885 0.2508 C 0 0 2 0 0 0 0 0 0 0 0 0 0.6297 -0.7819 -1.0775 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7954 0.0812 -1.3059 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5995 0.6004 -0.1784 C 0 0 1 0 0 0 0 0 0 0 0 0 2.2831 -0.1725 1.1211 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8393 -0.0953 1.2210 C 0 0 1 0 0 0 0 0 0 0 0 0 0.5121 1.2713 1.0160 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1509 -0.3917 2.4925 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2687 -0.0607 1.9645 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3393 -0.7544 0.5936 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.9393 -2.0007 0.9916 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3764 -0.2415 -0.2848 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.3794 1.1137 -0.8355 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.5103 1.5225 -1.7101 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7859 1.7985 -1.0231 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7764 2.2172 0.2210 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5235 2.4004 0.9054 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4295 2.7965 2.0841 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3455 2.1195 0.2124 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0512 2.5084 0.9432 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0670 1.6047 -1.7318 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5316 -0.2014 0.5731 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8450 -1.3026 -1.2938 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9132 0.5099 2.3084 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1337 1.2663 1.9315 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7018 1.3061 0.7693 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0983 0.5115 -0.3704 C 0 0 1 0 0 0 0 0 0 0 0 0 4.6111 -0.8988 -0.2009 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5930 1.0373 -1.6486 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5424 0.3893 -2.7080 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1803 2.3813 -1.7182 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8185 2.9203 -0.6930 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9305 2.1266 0.5478 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5458 -5.8290 -0.9779 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5897 -4.9668 -2.2033 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1385 -6.4178 -1.4711 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1423 -2.7229 1.6198 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4557 -2.5794 0.9101 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8848 -1.8064 -1.5191 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1569 -0.4977 -1.8473 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5350 -0.4369 -1.9951 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5190 0.9843 -1.9386 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4332 1.7001 -0.0058 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8015 -1.1123 0.9932 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4019 1.5279 0.1033 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2401 -1.3496 2.9512 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3848 0.3753 3.2673 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2149 1.0360 1.8169 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0398 -0.3573 2.6574 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1660 -2.5692 0.2596 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4440 1.4045 -1.4047 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2011 2.5765 -2.0785 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6256 0.9927 -2.6622 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3998 3.5052 0.6679 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8666 2.4097 2.0276 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7686 1.6994 0.6446 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9569 1.6259 -2.8353 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8115 2.3967 -1.4882 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5132 0.6261 -1.4692 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6916 -1.1124 0.9309 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3304 -0.8451 -2.1824 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0299 -1.9618 -1.6370 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6401 -1.9603 -0.8880 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2180 -0.2709 3.0341 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1742 1.1545 2.8298 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5829 1.8496 2.7563 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9380 -1.6418 -0.6896 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5776 -0.9602 -0.7436 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8352 -1.1566 0.8516 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1048 2.9787 -2.6290 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2596 3.9003 -0.7141 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0735 2.8584 1.3867 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7907 1.4239 0.5253 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 6 5 1 1 6 7 1 0 7 8 1 0 8 9 1 0 9 10 1 0 10 11 1 0 11 12 1 6 11 13 1 0 13 14 1 0 14 15 1 0 15 16 1 1 15 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 20 21 2 0 21 22 1 0 22 23 2 0 22 24 1 0 21 25 1 0 20 26 1 0 17 27 1 1 17 28 1 0 10 29 1 0 29 30 1 0 30 31 2 0 31 32 1 0 32 33 1 1 32 34 1 0 34 35 2 0 34 36 1 0 36 37 2 0 37 38 1 0 11 6 1 0 24 18 1 0 38 31 1 0 15 6 1 0 32 9 1 0 1 39 1 0 1 40 1 0 1 41 1 0 5 42 1 0 5 43 1 0 7 44 1 0 7 45 1 0 8 46 1 0 8 47 1 0 9 48 1 1 10 49 1 6 12 50 1 0 13 51 1 0 13 52 1 0 14 53 1 0 14 54 1 0 16 55 1 0 18 56 1 6 19 57 1 0 19 58 1 0 25 59 1 0 25 60 1 0 25 61 1 0 26 62 1 0 26 63 1 0 26 64 1 0 27 65 1 0 28 66 1 0 28 67 1 0 28 68 1 0 29 69 1 0 29 70 1 0 30 71 1 0 33 72 1 0 33 73 1 0 33 74 1 0 36 75 1 0 37 76 1 0 38 77 1 0 38 78 1 0 M END

Standard InCHIKey	RGHQRULWHKEQHE-GRVQADPTSA-N
Standard InCHI	InChI=1S/C30H40O8/c1-17-15-24(38-25(33)18(17)2)27(5,34)30(36)14-13-29(35)22-10-9-20-7-6-8-23(32)26(20,4)21(22)11-12-28(29,30)16-37-19(3)31/h6,8-9,21-22,24,34-36H,7,10-16H2,1-5H3/t21-,22+,24+,26-,27-,28+,29+,30+/m0/s1
SMILES	CC(=O)OC[C@]12CC[C@H]3[C@H]([C@]1(O)CC[C@@]2(O)[C@]([C@H]1CC(=C(C(=O)O1)C)C)(O)C)CC=C1[C@]3(C)C(=O)C=CC1

Calculated Properties

Physi-Chem Properties

Molecular Weight:	528.27	Volume:	539.157 ? Van der Waals volume.
Dense:	0.98	LogP:	1.728 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.827 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.869 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	5.0	Rigid Bonds:	29.0
TPSA:	130.36 ? Topological Polar Surface Area.	H-Bond Acceptor:	8.0
H-Bond Donor:	3.0	Rings:	5.0
Heavy Atoms:	8.0

MedChem Properties

QED Drug-Likeness Score:	0.375	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.472	Fsp³:	0.7
MCE-18:	99.412 ? 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:	0.248	Fluc inhibitor:	0.106 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.006 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.017 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.392	Promiscuous compounds:	0.38

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.903	MDCK Permeability:	-4.567
Pgp-inhibitor:	0.01	Pgp-substrate:	0.347
PAMPA:	0.985 ? 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):	0.014
20% Bioavailability (F20%):	0.889	30% Bioavailability (F30%):	0.929
50% Bioavailability (F50%):	0.978

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.02	MRP1:	0.982
Plasma Protein Binding (PPB):	94.617%	Volume Distribution (VD):	0.112
Fu:	3.908% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.998
OATP1B3 inhibitor:	0.994	BCRP inhibitor:	0.002
BSEP inhibitor:	0.985

ADMET: Metabolism

CYP1A2-inhibitor:	1.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.988	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.635	CYP2C9-substrate:	0.001
CYP2D6-inhibitor:	0.123	CYP2D6-substrate:	0.002
CYP3A4-inhibitor:	0.006	CYP3A4-substrate:	0.963
CYP2B6-substrate:	0.005	CYP2C8-inhibitor:	0.999
HLM stability:	0.982 ? 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):

2.687

Half-life (T1/2):

2.469

ADMET: Toxicity

hERG Blockers:	0.027	hERG Blockers (10um):	0.214
Human Hepatotoxicity (H-HT):	0.689	Drug-induced Liver Injury (DILI):	0.203
AMES Toxicity:	0.317	Rat Oral Acute Toxicity:	0.193
Maximum Recommended Daily Dose:	0.816	Skin Sensitization:	0.991
Carcinogencity:	0.867	Eye Corrosion:	0.001
Eye Irritation:	0.15	Respiratory Toxicity:	0.212
Drug-induced Neurotoxicity:	0.182	Ototoxicity:	0.465
Hematotoxicity:	0.267	Drug-induced Nephrotoxicity:	0.719
Genotoxicity:	0.851	RPMI-8226 Immunitoxicity:	0.104
A549 Cytotoxicity:	0.089	Hek293 Cytotoxicity:	0.525
BCF:	0.616 ? 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:	3.474 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.317 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.556 ? 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
NPO13447	Physalis chenopodifolia	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13447	Physalis chenopodifolia	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
IC50	15
TGI	1
EC50	4
Selectivity ratio	4
MTD	1

Activity Type	# Activity
Individual protein	8
Cell line	11
Unchecked	5
Organism	1

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT153	Individual protein	Androgen Receptor	Homo sapiens	IC50	=	580.0	nM	PMID[26305181]
NPT153	Individual protein	Androgen Receptor	Homo sapiens	IC50	=	750.0	nM	PMID[26305181]
NPT153	Individual protein	Androgen Receptor	Homo sapiens	IC50	=	770.0	nM	PMID[26305181]
NPT2816	Individual protein	Bromodomain-containing protein 4	Homo sapiens	IC50	=	3917.0	nM	PMID[36577036]
NPT2816	Individual protein	Bromodomain-containing protein 4	Homo sapiens	IC50	=	19.3	nM	PMID[36577036]
NPT3899	Individual protein	Bromodomain-containing protein 3	Homo sapiens	IC50	=	15820.0	nM	PMID[36577036]
NPT3899	Individual protein	Bromodomain-containing protein 3	Homo sapiens	IC50	=	18.0	nM	PMID[36577036]

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT858	Cell line	LNCaP	Homo sapiens	IC50	=	70.0	nM	PMID[26305181]
NPT306	Cell line	PC-3	Homo sapiens	IC50	=	130.0	nM	PMID[26305181]
NPT83	Cell line	MCF7	Homo sapiens	IC50	=	1900.0	nM	PMID[26305181]
NPT397	Cell line	NCI-H460	Homo sapiens	IC50	=	1200.0	nM	PMID[26305181]
NPT395	Cell line	SF-268	Homo sapiens	IC50	=	3400.0	nM	PMID[26305181]
NPT859	Cell line	HFF	Homo sapiens	IC50	>	3100.0	nM	PMID[26305181]
NPT306	Cell line	PC-3	Homo sapiens	TGI	=	66.0	%	PMID[26305181]
NPT369	Cell line	ACHN	Homo sapiens	IC50	=	564.0	nM	PMID[28257574]
NPT306	Cell line	PC-3	Homo sapiens	EC50	=	130.0	nM	PMID[36577036]
NPT859	Cell line	HFF	Homo sapiens	EC50	>	3000.0	nM	PMID[36577036]
NPT858	Cell line	LNCaP	Homo sapiens	EC50	=	130.0	nM	PMID[36577036]
NPT28438	Unchecked	Unchecked	n.a.	EC50	=	70.0	nM	PMID[36577036]
NPT28438	Unchecked	Unchecked	n.a.	Selectivity ratio	=	30.0	n.a.	PMID[36577036]

In vivo activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT32	Organism	Mus musculus	Mus musculus	MTD	=	50.0	mg kg-1	PMID[26305181]

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 NPC5292 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	18983
0.1-0.2	26392
0.2-0.3	4337
0.3-0.4	102
0.4-0.5	20
0.5-0.6	10
0.6-0.7	10
0.7-0.8	0
0.8-0.85	0
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8873	High Similarity	NPC484718
0.7973	Intermediate Similarity	NPC484717
0.7857	Intermediate Similarity	NPC153440
0.7308	Intermediate Similarity	NPC484725
0.6933	Remote Similarity	NPC107493
0.6867	Remote Similarity	NPC484715
0.6842	Remote Similarity	NPC103045
0.6711	Remote Similarity	NPC79579
0.6579	Remote Similarity	NPC190286
0.6543	Remote Similarity	NPC55621
0.6364	Remote Similarity	NPC176840
0.6154	Remote Similarity	NPC484742
0.6064	Remote Similarity	NPC484726
0.6	Remote Similarity	NPC484716
0.5949	Remote Similarity	NPC225826
0.5802	Remote Similarity	NPC46570
0.5679	Remote Similarity	NPC191620
0.5667	Remote Similarity	NPC484720
0.5632	Remote Similarity	NPC484719
0.561	Remote Similarity	NPC44428
0.561	Remote Similarity	NPC78691
0.5556	Remote Similarity	NPC270850
0.5556	Remote Similarity	NPC305260
0.5542	Remote Similarity	NPC470961

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC5292 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6673
0.1-0.2	2335
0.2-0.3	142
0.3-0.4	0
0.4-0.5	0
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