NPASS Compound

Natural Product: NPC158319

Natural Product ID	NPC158319
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	REOWXEUUAXLCRM-DTRRUJLXSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	14216306
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 5.6712 1.2518 -2.1614 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8957 1.1776 -0.8679 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0197 2.2072 -0.0777 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8495 3.3963 -0.3778 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2825 2.1537 1.2020 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3421 3.0983 2.0197 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5337 1.0358 1.4584 O 0 0 0 0 0 0 0 0 0 0 0 0 3.9065 -0.1883 0.8642 C 0 0 2 0 0 0 0 0 0 0 0 0 4.0716 -0.0292 -0.6262 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0979 -1.3466 1.2764 C 0 0 1 0 0 0 0 0 0 0 0 0 3.2264 -1.4944 2.8012 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7196 -1.4721 0.7853 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4118 -2.4329 -0.1240 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0370 -2.3708 -0.4724 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.2868 -0.9248 -0.2491 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6794 -0.4784 -0.2169 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.1986 -0.4004 -1.6568 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6867 -0.0477 -1.5498 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.9260 1.1595 -0.7231 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.4216 1.2971 -0.4914 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6717 2.6243 0.1699 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7466 3.1428 0.9763 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4812 2.4764 1.2554 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7012 3.0610 2.0420 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2051 1.1809 0.6070 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.7443 0.1153 1.5557 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7478 0.9390 0.2871 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8410 1.3123 1.3752 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5407 0.6954 1.3032 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4666 -0.7669 1.0849 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.3024 -1.4267 2.2080 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5125 2.2786 -1.4394 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.4426 -1.1508 -1.2300 O 0 0 0 0 0 0 0 0 0 0 0 0 0.4108 -0.1342 -1.1686 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3452 -2.9027 -1.7003 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1526 -4.0206 -1.8419 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5868 -4.5191 -0.7750 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4662 -4.5699 -3.1809 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8711 2.3023 -2.4476 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6485 0.7438 -2.0725 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0710 0.8148 -2.9997 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9411 4.0284 0.5218 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4173 4.0355 -1.1780 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9078 3.0976 -0.6350 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9715 -0.3730 1.2281 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1389 0.0995 -1.1771 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6246 -0.9332 -0.9770 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7232 -2.2619 0.9465 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7585 -0.6404 3.3216 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3189 -1.4163 3.0005 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9056 -2.4776 3.1469 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0601 -3.1677 -0.5752 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5485 -2.9607 0.3174 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3923 -1.1505 0.3017 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1740 -1.3753 -2.1733 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6528 0.3540 -2.2433 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9727 0.2250 -2.6096 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9676 1.2408 -1.4378 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7704 0.5033 0.1778 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6169 3.0921 -0.0562 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9972 4.1038 1.4176 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2318 -0.7175 1.0518 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9725 -0.2776 2.2314 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5344 0.5536 2.2354 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5311 1.6266 -0.5870 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2642 1.1747 2.3909 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6278 2.4228 1.2968 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9763 0.9048 2.3004 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0428 1.1822 0.4615 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5392 -0.6450 2.9544 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3211 -2.2486 2.6692 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2367 -1.8925 1.9068 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2730 2.8181 -1.7529 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8813 -1.9372 -1.0482 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9024 -0.6849 -1.8047 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5289 -4.8485 -3.2872 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2795 -3.7618 -3.9234 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8710 -5.4805 -3.4081 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 2 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 1 25 27 1 0 27 28 1 0 28 29 1 0 29 30 1 0 30 31 1 1 19 32 1 6 18 33 1 0 15 34 1 6 14 35 1 0 35 36 1 0 36 37 2 0 36 38 1 0 9 2 1 0 30 12 1 0 30 15 1 0 27 16 1 0 25 19 1 0 1 39 1 0 1 40 1 0 1 41 1 0 4 42 1 0 4 43 1 0 4 44 1 0 8 45 1 1 9 46 1 0 9 47 1 0 10 48 1 6 11 49 1 0 11 50 1 0 11 51 1 0 13 52 1 0 14 53 1 1 16 54 1 1 17 55 1 0 17 56 1 0 18 57 1 6 20 58 1 0 20 59 1 0 21 60 1 0 22 61 1 0 26 62 1 0 26 63 1 0 26 64 1 0 27 65 1 6 28 66 1 0 28 67 1 0 29 68 1 0 29 69 1 0 31 70 1 0 31 71 1 0 31 72 1 0 32 73 1 0 33 74 1 0 34 75 1 0 38 76 1 0 38 77 1 0 38 78 1 0 M END

Standard InCHIKey	REOWXEUUAXLCRM-DTRRUJLXSA-N
Standard InCHI	InChI=1S/C30H40O8/c1-15-12-22(38-26(34)16(15)2)17(3)20-14-25(37-18(4)31)30(36)21-13-24(33)29(35)10-7-8-23(32)28(29,6)19(21)9-11-27(20,30)5/h7-8,14,17,19,21-22,24-25,33,35-36H,9-13H2,1-6H3/t17-,19-,21+,22+,24+,25-,27+,28-,29-,30-/m0/s1
SMILES	CC1=C(C)C(=O)O[C@H](C1)[C@@H](C)C1=C[C@@H]([C@]2([C@@H]3C[C@H]([C@]4(CC=CC(=O)[C@]4(C)[C@H]3CC[C@]12C)O)O)O)OC(=O)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	528.27	Volume:	539.157 ? Van der Waals volume.
Dense:	0.98	LogP:	1.033 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.432 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.132 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	4.0	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:	0.377	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.611	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:	0.636	Fluc inhibitor:	0.022 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.03 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.007 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.257	Promiscuous compounds:	0.425

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.863	MDCK Permeability:	-4.485
Pgp-inhibitor:	0.228	Pgp-substrate:	0.78
PAMPA:	0.995 ? 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):	0.006
20% Bioavailability (F20%):	0.918	30% Bioavailability (F30%):	0.954
50% Bioavailability (F50%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.029	MRP1:	0.962
Plasma Protein Binding (PPB):	82.511%	Volume Distribution (VD):	-0.025
Fu:	16.328% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.998
OATP1B3 inhibitor:	0.967	BCRP inhibitor:	0.049
BSEP inhibitor:	0.999

ADMET: Metabolism

CYP1A2-inhibitor:	0.211	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.407	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.093	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.005	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.995
HLM stability:	0.067 ? 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):

5.282

Half-life (T1/2):

1.913

ADMET: Toxicity

hERG Blockers:	0.017	hERG Blockers (10um):	0.133
Human Hepatotoxicity (H-HT):	0.777	Drug-induced Liver Injury (DILI):	0.456
AMES Toxicity:	0.537	Rat Oral Acute Toxicity:	0.382
Maximum Recommended Daily Dose:	0.66	Skin Sensitization:	0.981
Carcinogencity:	0.884	Eye Corrosion:	0.002
Eye Irritation:	0.54	Respiratory Toxicity:	0.198
Drug-induced Neurotoxicity:	0.087	Ototoxicity:	0.688
Hematotoxicity:	0.314	Drug-induced Nephrotoxicity:	0.938
Genotoxicity:	0.94	RPMI-8226 Immunitoxicity:	0.112
A549 Cytotoxicity:	0.105	Hek293 Cytotoxicity:	0.288
BCF:	0.55 ? 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:	3.395 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.159 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.345 ? 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	9
CC50	2

Activity Type	# Activity
Cell line	2
Organism	2
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
NPT460	Cell line	MT2	Homo sapiens	CC50	>	100000.0	nM	PMID[34549952]
NPT1114	Organism	Human immunodeficiency virus	Human immunodeficiency virus	IC50	=	67900.0	nM	PMID[34549952]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	IC50	>	10000.0	nM	PMID[27295506]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	IC50	=	64060.0	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 NPC158319 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	17571
0.1-0.2	27143
0.2-0.3	4955
0.3-0.4	132
0.4-0.5	21
0.5-0.6	15
0.6-0.7	14
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC484699
0.9394	High Similarity	NPC484700
0.9394	High Similarity	NPC484701
0.7778	Intermediate Similarity	NPC606803
0.7639	Intermediate Similarity	NPC484696
0.7639	Intermediate Similarity	NPC484697
0.7297	Intermediate Similarity	NPC484702
0.6883	Remote Similarity	NPC62608
0.6883	Remote Similarity	NPC601528
0.6842	Remote Similarity	NPC246093
0.6753	Remote Similarity	NPC41988
0.6582	Remote Similarity	NPC484703
0.65	Remote Similarity	NPC83438
0.6456	Remote Similarity	NPC606764
0.6364	Remote Similarity	NPC607253
0.6265	Remote Similarity	NPC484713
0.625	Remote Similarity	NPC166213
0.625	Remote Similarity	NPC605398
0.6076	Remote Similarity	NPC484708
0.6071	Remote Similarity	NPC484698
0.6	Remote Similarity	NPC601733
0.5976	Remote Similarity	NPC484707
0.5974	Remote Similarity	NPC147912
0.5926	Remote Similarity	NPC600975
0.5926	Remote Similarity	NPC602010
0.5904	Remote Similarity	NPC602882
0.5765	Remote Similarity	NPC610734
0.5581	Remote Similarity	NPC609088
0.5476	Remote Similarity	NPC610379
0.5476	Remote Similarity	NPC610735
0.5366	Remote Similarity	NPC484709
0.5349	Remote Similarity	NPC64449
0.5227	Remote Similarity	NPC607882
0.5176	Remote Similarity	NPC470959
0.5176	Remote Similarity	NPC476965
0.5054	Remote Similarity	NPC476966

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC158319 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6311
0.1-0.2	2674
0.2-0.3	164
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	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