NPASS Compound

Natural Product: NPC232486

Natural Product ID	NPC232486
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	ZBFPGLKEWSMWSG-ZMBNEQANSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	50990065
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

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 79 82 0 0 0 0 0 0 0 0999 V2000 6.3164 -0.6667 2.8559 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0989 0.5304 2.0106 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0478 0.5664 1.2025 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1023 -0.5664 1.1398 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0653 -1.0954 -0.2541 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5854 -0.0902 -1.2864 C 0 0 1 0 0 0 0 0 0 0 0 0 3.6488 -0.8055 -2.6002 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3621 0.6414 -0.9553 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0469 1.6223 -2.0721 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5182 1.7783 -2.0548 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1235 0.3599 -1.7971 C 0 0 2 0 0 0 0 0 0 0 0 0 0.3712 -0.4147 -3.0507 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2679 0.1712 -1.3713 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2634 0.7791 -1.9463 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6878 0.6054 -1.5348 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6803 0.2877 -0.0625 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.0891 0.3128 0.4808 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6186 1.7121 0.1148 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0084 -0.6653 -0.2018 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0730 0.1696 1.9672 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.6855 0.0875 2.5147 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8205 -0.9418 1.8427 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8853 -0.8997 0.3321 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.3855 -2.2155 -0.1632 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5151 -0.7396 -0.2597 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5253 -1.4581 0.2679 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8947 -1.3539 -0.2688 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0783 0.0513 -0.6387 C 0 0 1 0 0 0 0 0 0 0 0 0 0.4677 0.8540 0.5400 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8782 -0.8964 2.4078 O 0 0 0 0 0 0 0 0 0 0 0 0 7.0740 1.6489 2.1043 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2555 -0.5373 3.4212 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4490 -0.8843 3.5126 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4668 -1.5878 2.2218 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9285 1.4504 0.6060 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4881 -1.3783 1.7839 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1155 -0.2965 1.5689 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1584 -1.2705 -0.5248 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6252 -2.1008 -0.3759 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3992 0.6580 -1.3367 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6671 -1.3191 -2.5814 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9554 -1.6186 -2.7582 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7674 -0.0801 -3.4261 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6798 1.3110 -0.0910 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4360 1.3506 -3.0457 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4227 2.6481 -1.8624 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2141 2.4987 -1.3022 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2020 2.1513 -3.0479 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6214 -0.3945 -3.6060 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5690 -1.4866 -2.9247 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0552 0.0763 -3.7734 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0337 1.4537 -2.7776 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2457 1.5553 -1.6632 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0918 -0.2055 -2.1634 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1737 1.1784 0.4216 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8204 2.4542 0.0800 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3627 2.0439 0.8626 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1230 1.6945 -0.8732 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9619 -0.1785 -0.5622 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5713 -1.1287 -1.1097 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3788 -1.4441 0.5286 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5435 1.0803 2.4419 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2396 1.0907 2.5272 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7763 -0.2323 3.5886 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0084 -1.9637 2.2371 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7781 -0.6935 2.1315 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4479 -2.2289 -1.2848 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5725 -2.9693 0.0634 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2862 -2.5914 0.2921 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7848 -2.1119 1.0845 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9381 -2.1151 -1.0400 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5084 -1.7238 0.5798 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1968 1.6512 0.8797 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4333 1.3923 0.2831 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3041 0.2424 1.4246 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8242 -0.6874 2.4168 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4825 2.5987 1.9515 H 0 0 0 0 0 0 0 0 0 0 0 0 7.7730 1.6152 1.2190 H 0 0 0 0 0 0 0 0 0 0 0 0 7.6036 1.6641 3.0621 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 2 3 3 4 1 0 4 5 1 0 5 6 1 0 6 7 1 0 6 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 2 0 14 15 1 0 15 16 1 0 16 17 1 0 17 18 1 0 17 19 1 0 17 20 1 0 20 21 1 0 21 22 1 0 22 23 1 0 23 24 1 6 23 25 1 0 25 26 2 0 26 27 1 0 27 28 1 0 28 29 1 1 20 30 1 0 2 31 1 0 28 8 1 0 28 11 1 0 25 13 1 0 23 16 1 0 1 32 1 0 1 33 1 0 1 34 1 0 3 35 1 0 4 36 1 0 4 37 1 0 5 38 1 0 5 39 1 0 6 40 1 6 7 41 1 0 7 42 1 0 7 43 1 0 8 44 1 0 9 45 1 0 9 46 1 0 10 47 1 0 10 48 1 0 12 49 1 0 12 50 1 0 12 51 1 0 14 52 1 0 15 53 1 0 15 54 1 0 16 55 1 1 18 56 1 0 18 57 1 0 18 58 1 0 19 59 1 0 19 60 1 0 19 61 1 0 20 62 1 1 21 63 1 0 21 64 1 0 22 65 1 0 22 66 1 0 24 67 1 0 24 68 1 0 24 69 1 0 26 70 1 0 27 71 1 0 27 72 1 0 29 73 1 0 29 74 1 0 29 75 1 0 30 76 1 0 31 77 1 0 31 78 1 0 31 79 1 0 M END

Standard InCHIKey	ZBFPGLKEWSMWSG-ZMBNEQANSA-N
Standard InCHI	InChI=1S/C30H48O/c1-20(2)10-9-11-21(3)22-14-18-30(8)24-12-13-25-27(4,5)26(31)16-17-28(25,6)23(24)15-19-29(22,30)7/h10,12,15,21-22,25-26,31H,9,11,13-14,16-19H2,1-8H3/t21-,22?,25+,26+,28-,29+,30-/m1/s1
SMILES	CC(=CCC[C@@H](C)C1CC[C@]2(C)C3=CC[C@H]4C(C)(C)[C@H](CC[C@]4(C)C3=CC[C@@]12C)O)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	424.37	Volume:	494.091 ? Van der Waals volume.
Dense:	0.859	LogP:	7.337 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	4.957 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-7.479 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	4.0	Rigid Bonds:	21.0
TPSA:	20.23 ? Topological Polar Surface Area.	H-Bond Acceptor:	1.0
H-Bond Donor:	1.0	Rings:	4.0
Heavy Atoms:	1.0

MedChem Properties

QED Drug-Likeness Score:	0.45	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.743	Fsp³:	0.8
MCE-18:	76.926 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted	GSK Rule:	Accepted
Golden Triangle Rule:	Rejected	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.836	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.019 ? 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:	0.69	Promiscuous compounds:	0.086

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.619	MDCK Permeability:	-4.634
Pgp-inhibitor:	0.763	Pgp-substrate:	0.073
PAMPA:	0.272 ? 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):	0.0
20% Bioavailability (F20%):	0.028	30% Bioavailability (F30%):	0.022
50% Bioavailability (F50%):	0.991

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.963	MRP1:	0.638
Plasma Protein Binding (PPB):	93.445%	Volume Distribution (VD):	-0.03
Fu:	6.579% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.996	BCRP inhibitor:	0.834
BSEP inhibitor:	0.927

ADMET: Metabolism

CYP1A2-inhibitor:	0.002	CYP1A2-substrate:	0.889
CYP2C19-inhibitor:	0.998	CYP2C19-substrate:	0.181
CYP2C9-inhibitor:	0.006	CYP2C9-substrate:	0.281
CYP2D6-inhibitor:	0.468	CYP2D6-substrate:	0.048
CYP3A4-inhibitor:	0.993	CYP3A4-substrate:	0.994
CYP2B6-substrate:	0.001	CYP2C8-inhibitor:	0.998
HLM stability:	0.963 ? 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):

12.658

Half-life (T1/2):

0.357

ADMET: Toxicity

hERG Blockers:	0.108	hERG Blockers (10um):	0.438
Human Hepatotoxicity (H-HT):	0.584	Drug-induced Liver Injury (DILI):	0.053
AMES Toxicity:	0.146	Rat Oral Acute Toxicity:	0.241
Maximum Recommended Daily Dose:	0.334	Skin Sensitization:	0.942
Carcinogencity:	0.744	Eye Corrosion:	0.426
Eye Irritation:	0.928	Respiratory Toxicity:	0.638
Drug-induced Neurotoxicity:	0.155	Ototoxicity:	0.491
Hematotoxicity:	0.147	Drug-induced Nephrotoxicity:	0.495
Genotoxicity:	0.033	RPMI-8226 Immunitoxicity:	0.105
A549 Cytotoxicity:	0.185	Hek293 Cytotoxicity:	0.234
BCF:	3.094 ? 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:	5.051 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.868 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	6.018 ? 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
NPO10031	Euphorbia antiquorum	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11858748]
NPO10031	Euphorbia antiquorum	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24840014]
NPO10031	Euphorbia antiquorum	Species	Euphorbiaceae	Eukaryota	Stems	n.a.	n.a.	PMID[31180680]
NPO10031	Euphorbia antiquorum	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10031	Euphorbia antiquorum	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO10031	Euphorbia antiquorum	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10031	Euphorbia antiquorum	Species	Euphorbiaceae	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

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

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 NPC232486 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	24233
0.1-0.2	21626
0.2-0.3	3482
0.3-0.4	396
0.4-0.5	71
0.5-0.6	31
0.6-0.7	8
0.7-0.8	0
0.8-0.85	1
0.85-0.9	1
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC205455
0.8679	High Similarity	NPC202389
0.8364	Intermediate Similarity	NPC475772
0.7963	Intermediate Similarity	NPC6707
0.7627	Intermediate Similarity	NPC212948
0.7321	Intermediate Similarity	NPC147568
0.678	Remote Similarity	NPC231310
0.6613	Remote Similarity	NPC84271
0.6613	Remote Similarity	NPC102414
0.6562	Remote Similarity	NPC214697
0.6379	Remote Similarity	NPC46160
0.6379	Remote Similarity	NPC20853
0.6379	Remote Similarity	NPC202642
0.6269	Remote Similarity	NPC484797
0.5882	Remote Similarity	NPC141401
0.5873	Remote Similarity	NPC275740
0.5873	Remote Similarity	NPC86319
0.5846	Remote Similarity	NPC222845
0.5846	Remote Similarity	NPC296577
0.5833	Remote Similarity	NPC72507
0.5821	Remote Similarity	NPC469406
0.5781	Remote Similarity	NPC4166
0.5781	Remote Similarity	NPC311092
0.5714	Remote Similarity	NPC201852
0.5672	Remote Similarity	NPC77168
0.5672	Remote Similarity	NPC138536
0.5574	Remote Similarity	NPC318136
0.5538	Remote Similarity	NPC89077
0.5484	Remote Similarity	NPC186191
0.5469	Remote Similarity	NPC170793
0.5469	Remote Similarity	NPC94755
0.5294	Remote Similarity	NPC44181
0.5294	Remote Similarity	NPC606857
0.5278	Remote Similarity	NPC39082
0.5278	Remote Similarity	NPC610107
0.5211	Remote Similarity	NPC478313
0.5211	Remote Similarity	NPC489790
0.5167	Remote Similarity	NPC85346
0.5167	Remote Similarity	NPC65897
0.5167	Remote Similarity	NPC80237
0.5156	Remote Similarity	NPC214570
0.5147	Remote Similarity	NPC69454
0.5143	Remote Similarity	NPC48647
0.5082	Remote Similarity	NPC240604
0.5072	Remote Similarity	NPC87552

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC232486 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	8021
0.1-0.2	1062
0.2-0.3	64
0.3-0.4	3
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