NPASS Compound

Natural Product: NPC484712

Natural Product ID	NPC484712
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	IKIQWRCLUGSCEA-ITBIZAQQSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	134135392
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 6.9954 1.4384 1.4703 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7859 0.5886 1.2726 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9968 -0.6652 0.9515 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3369 -1.2409 0.7850 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8086 -1.5020 0.7561 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9378 -2.7358 0.4416 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5990 -0.8833 0.9302 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4148 0.4382 0.6310 C 0 0 2 0 0 0 0 0 0 0 0 0 4.4555 1.2196 1.4560 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1086 1.0859 0.7979 C 0 0 1 0 0 0 0 0 0 0 0 0 2.3258 2.5540 0.3610 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9099 0.6032 0.1219 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9906 0.5527 -1.3867 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1231 -0.6268 -1.7265 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.7624 -0.9428 -0.5460 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.1404 -0.4976 -0.6112 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5217 0.5588 -1.6284 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6933 1.3907 -1.2414 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.6450 1.0372 -0.3180 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.3421 2.1466 0.4277 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4135 1.7161 1.3229 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2503 0.5878 1.9975 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0239 -0.1704 1.8205 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6415 -0.8721 2.7699 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2453 -0.1302 0.5773 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.7221 -1.3718 -0.2038 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7783 -0.0275 0.6952 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.1032 -0.6266 1.8649 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6807 -0.0431 1.8164 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1053 -0.5267 0.6186 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8387 -1.7344 1.1603 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0098 0.8131 -1.6165 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7754 -2.3686 -0.5169 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5579 -0.4492 -2.9215 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3143 -1.1978 -4.0510 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5638 -2.0821 -3.9984 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1164 -0.9052 -5.2677 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7786 2.2023 2.2295 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8648 0.8549 1.7666 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2329 1.9679 0.5150 H 0 0 0 0 0 0 0 0 0 0 0 0 7.9067 -0.7067 0.0074 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2640 -2.3074 0.5208 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8383 -1.1822 1.7739 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7904 0.5950 -0.4333 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4805 2.2889 1.1638 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2032 1.1762 2.5360 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8308 1.2184 1.8963 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3596 2.9525 -0.0192 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6600 3.1441 1.2331 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1283 2.5990 -0.3930 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1658 1.5083 0.2445 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0632 0.4051 -1.7240 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7090 1.4943 -1.8946 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8610 -1.4694 -1.9076 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8114 -1.3622 -0.9148 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6570 1.2403 -1.7502 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7962 0.0978 -2.6186 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6930 2.4207 -1.7098 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6206 2.7486 1.0193 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8125 2.8233 -0.3289 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3444 2.3019 1.4467 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0466 0.2539 2.6733 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8210 -1.5233 0.0482 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2424 -2.2885 0.1215 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7493 -1.1834 -1.2952 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5176 1.0804 0.7239 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5138 -0.1354 2.8002 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0901 -1.7116 1.9230 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8314 1.0674 1.7295 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1471 -0.2110 2.7600 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0098 -2.4916 1.4174 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3210 -1.5837 2.1176 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3973 -2.3004 0.3871 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6769 -2.7246 -0.4494 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4940 0.1372 -5.2298 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5243 -1.1212 -6.1573 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0348 -1.5593 -5.2411 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 2 0 3 4 1 0 3 5 1 0 5 6 2 0 5 7 1 0 7 8 1 0 8 9 1 0 8 10 1 0 10 11 1 0 10 12 1 0 12 13 1 0 13 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 0 20 21 1 0 21 22 2 0 22 23 1 0 23 24 2 0 23 25 1 0 25 26 1 6 25 27 1 0 27 28 1 0 28 29 1 0 29 30 1 0 30 31 1 1 19 32 1 6 15 33 1 1 14 34 1 0 34 35 1 0 35 36 2 0 35 37 1 0 9 2 1 0 30 12 1 0 30 15 1 0 27 16 1 0 32 18 1 0 25 19 1 0 1 38 1 0 1 39 1 0 1 40 1 0 4 41 1 0 4 42 1 0 4 43 1 0 8 44 1 6 9 45 1 0 9 46 1 0 10 47 1 1 11 48 1 0 11 49 1 0 11 50 1 0 12 51 1 6 13 52 1 0 13 53 1 0 14 54 1 6 16 55 1 6 17 56 1 0 17 57 1 0 18 58 1 6 20 59 1 0 20 60 1 0 21 61 1 0 22 62 1 0 26 63 1 0 26 64 1 0 26 65 1 0 27 66 1 1 28 67 1 0 28 68 1 0 29 69 1 0 29 70 1 0 31 71 1 0 31 72 1 0 31 73 1 0 33 74 1 0 37 75 1 0 37 76 1 0 37 77 1 0 M END

Standard InCHIKey	IKIQWRCLUGSCEA-ITBIZAQQSA-N
Standard InCHI	InChI=1S/C30H40O7/c1-15-12-22(36-26(33)16(15)2)17(3)20-13-25(35-18(4)31)30(34)21-14-24-29(37-24)10-7-8-23(32)28(29,6)19(21)9-11-27(20,30)5/h7-8,17,19-22,24-25,34H,9-14H2,1-6H3/t17-,19-,20+,21+,22+,24+,25-,27+,28-,29+,30+/m0/s1
SMILES	CC1=C(C)C(=O)O[C@H](C1)[C@@H](C)[C@H]1C[C@@H]([C@@]2([C@@H]3C[C@@H]4[C@@]5(CC=CC(=O)[C@]5(C)[C@H]3CC[C@]12C)O4)O)OC(=O)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	512.28	Volume:	524.447 ? Van der Waals volume.
Dense:	0.977	LogP:	1.84 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.174 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.471 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	4.0	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:	0.449	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.974	Fsp³:	0.767
MCE-18:	151.358 ? 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:	0.659	Fluc inhibitor:	0.032 ? 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:	0.002 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.277	Promiscuous compounds:	0.716

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.979	MDCK Permeability:	-4.667
Pgp-inhibitor:	0.829	Pgp-substrate:	0.233
PAMPA:	0.867 ? 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):	0.001
20% Bioavailability (F20%):	0.323	30% Bioavailability (F30%):	0.473
50% Bioavailability (F50%):	0.966

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.002	MRP1:	0.984
Plasma Protein Binding (PPB):	89.316%	Volume Distribution (VD):	0.195
Fu:	9.974% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.992	BCRP inhibitor:	0.012
BSEP inhibitor:	0.996

ADMET: Metabolism

CYP1A2-inhibitor:	0.964	CYP1A2-substrate:	0.011
CYP2C19-inhibitor:	0.991	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.014	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.002	CYP2D6-substrate:	0.001
CYP3A4-inhibitor:	0.238	CYP3A4-substrate:	0.007
CYP2B6-substrate:	0.029	CYP2C8-inhibitor:	0.942
HLM stability:	0.658 ? 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):

5.171

Half-life (T1/2):

1.616

ADMET: Toxicity

hERG Blockers:	0.027	hERG Blockers (10um):	0.208
Human Hepatotoxicity (H-HT):	0.541	Drug-induced Liver Injury (DILI):	0.253
AMES Toxicity:	0.558	Rat Oral Acute Toxicity:	0.624
Maximum Recommended Daily Dose:	0.705	Skin Sensitization:	0.988
Carcinogencity:	0.766	Eye Corrosion:	0.037
Eye Irritation:	0.61	Respiratory Toxicity:	0.542
Drug-induced Neurotoxicity:	0.156	Ototoxicity:	0.418
Hematotoxicity:	0.504	Drug-induced Nephrotoxicity:	0.661
Genotoxicity:	0.869	RPMI-8226 Immunitoxicity:	0.108
A549 Cytotoxicity:	0.113	Hek293 Cytotoxicity:	0.282
BCF:	0.731 ? 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:	3.59 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.405 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.718 ? 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
NPO1680	Physalis angulata	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17580910]
NPO1680	Physalis angulata	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21954931]
NPO1680	Physalis angulata	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23270478]
NPO1680	Physalis angulata	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25396337]
NPO1680	Physalis angulata	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27295506]
NPO1680	Physalis angulata	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1680	Physalis angulata	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	7

Activity Type	# Activity
Non-molecular	7

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	IC50	=	490.0	nM	PMID[27295506]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	IC50	=	900.0	nM	PMID[27295506]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	IC50	=	390.0	nM	PMID[27295506]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	IC50	=	710.0	nM	PMID[27295506]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	IC50	=	730.0	nM	PMID[27295506]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	IC50	=	7430.0	nM	PMID[27295506]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	IC50	=	1360.0	nM	PMID[27295506]

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 NPC484712 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	18254
0.1-0.2	26649
0.2-0.3	4725
0.3-0.4	130
0.4-0.5	66
0.5-0.6	17
0.6-0.7	10
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	Natural Product ID
0.7703	Intermediate Similarity	NPC484736
0.7467	Intermediate Similarity	NPC484714
0.7013	Intermediate Similarity	NPC166213
0.7013	Intermediate Similarity	NPC605398
0.6835	Remote Similarity	NPC164523
0.6463	Remote Similarity	NPC484719
0.641	Remote Similarity	NPC473203
0.6364	Remote Similarity	NPC158285
0.6329	Remote Similarity	NPC246093
0.6173	Remote Similarity	NPC601815
0.6173	Remote Similarity	NPC607008
0.6154	Remote Similarity	NPC122056
0.6024	Remote Similarity	NPC55621
0.6	Remote Similarity	NPC611165
0.5783	Remote Similarity	NPC604847
0.5595	Remote Similarity	NPC609769
0.5595	Remote Similarity	NPC610140
0.5581	Remote Similarity	NPC204812
0.5422	Remote Similarity	NPC484741
0.5412	Remote Similarity	NPC484737
0.5412	Remote Similarity	NPC484706
0.5393	Remote Similarity	NPC32868
0.5227	Remote Similarity	NPC607675
0.5185	Remote Similarity	NPC484744
0.5176	Remote Similarity	NPC601733
0.5122	Remote Similarity	NPC286528
0.5116	Remote Similarity	NPC600975
0.5116	Remote Similarity	NPC602010
0.5116	Remote Similarity	NPC608655
0.5059	Remote Similarity	NPC285729
0.5057	Remote Similarity	NPC610379

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC484712 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6801
0.1-0.2	2147
0.2-0.3	201
0.3-0.4	0
0.4-0.5	1
0.5-0.6	0
0.6-0.7	0
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
		NPD

Bioactivity similarity

Similar Natural Products in NPASS

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

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data