NPASS Compound

Natural Product: NPC482307

Natural Product ID	NPC482307
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	PDRWXFDCQXKDSK-REVJNMIYSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	n.a.
Chemical Classification	CHEMONTID:0000000 [Organic compounds]

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 83 85 0 0 0 0 0 0 0 0999 V2000 2.2308 4.3246 -0.2232 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8441 3.3681 -1.2686 C 0 0 1 0 0 0 0 0 0 0 0 0 2.7350 2.1836 -1.4152 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6750 1.7615 -0.5959 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4740 0.4955 -0.9312 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6445 0.3513 -0.0530 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9089 0.5626 -2.3668 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4759 -0.6602 -0.8155 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2592 -1.3954 -1.7444 O 0 0 0 0 0 0 0 0 0 0 0 0 2.7545 -0.8773 0.4592 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5305 -1.6362 0.4985 C 0 0 2 0 0 0 0 0 0 0 0 0 0.2434 -1.3946 -0.1155 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0437 -2.2571 -1.1907 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9121 -0.5176 0.0779 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.0305 0.9100 -0.2414 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6650 1.6585 0.9071 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.5453 2.5091 1.4756 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.4902 2.5941 2.9475 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7230 1.7572 0.8936 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2919 1.5502 -0.4735 C 0 0 2 0 0 0 0 0 0 0 0 0 0.3931 2.8765 -1.1311 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4689 3.5385 -1.5346 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8377 0.7443 -1.4504 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1682 0.7464 -2.6974 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8345 1.3827 -2.9984 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7587 -0.1250 -3.7680 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2534 0.8740 1.8914 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.6082 1.0511 2.1738 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2954 1.9170 1.5404 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3326 0.2655 3.2062 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0782 -1.1226 -0.5623 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0452 -1.8225 0.0854 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9526 -1.9896 1.3283 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2115 -2.3969 -0.6410 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3508 -2.2328 -1.9911 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4277 -2.7671 -2.6513 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3792 -3.4757 -1.9516 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2634 -3.6572 -0.5849 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1693 -3.1073 0.0478 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1925 -1.8219 1.9324 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3242 -3.0065 2.5760 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7449 -4.0120 1.9751 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9831 -3.2011 4.0291 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3493 4.6168 0.3833 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0352 4.0347 0.4756 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5763 5.2834 -0.7053 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8311 3.8863 -2.2425 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6841 1.5914 -2.3274 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9533 2.2402 0.3353 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5579 0.7175 -0.5960 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8409 -0.7200 0.1488 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5399 0.9494 0.8687 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1494 1.5886 -2.7110 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8187 -0.1012 -2.4501 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1460 0.0680 -3.0077 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7960 0.0736 1.0027 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5498 -1.5173 1.0522 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8724 -2.7311 0.2808 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8636 -2.2008 -1.7473 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7791 -2.9736 -1.4700 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1903 -0.7100 1.1859 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7044 1.0644 -1.1357 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4354 2.3558 0.4453 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6406 3.5041 1.0357 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6722 3.6316 3.3429 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5547 2.3485 3.2936 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2370 1.9579 3.4733 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8055 0.8662 1.5665 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5309 2.4186 1.1551 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5998 0.3708 -4.7678 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3285 -1.1386 -3.7597 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8557 -0.2023 -3.6815 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6616 -0.1054 3.9959 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9384 -0.5519 2.7361 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0849 0.9186 3.7209 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6285 -1.6874 -2.5635 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5502 -2.6401 -3.7429 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2367 -3.8993 -2.4891 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0216 -4.2172 -0.0539 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0558 -3.2362 1.1229 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7957 -3.8294 4.4478 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0375 -3.7380 4.1632 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0108 -2.2324 4.5708 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 3 4 2 0 4 5 1 0 5 6 1 0 5 7 1 0 5 8 1 0 8 9 2 0 8 10 1 0 10 11 1 0 11 12 1 0 12 13 2 0 12 14 1 0 14 15 1 0 15 16 1 0 16 17 1 0 17 18 1 0 17 19 1 0 19 20 1 0 20 21 1 0 21 22 2 0 20 23 1 6 23 24 1 0 24 25 2 0 24 26 1 0 16 27 1 0 27 28 1 0 28 29 2 0 28 30 1 0 14 31 1 0 31 32 1 0 32 33 2 0 32 34 1 0 34 35 2 0 35 36 1 0 36 37 2 0 37 38 1 0 38 39 2 0 11 40 1 0 40 41 1 0 41 42 2 0 41 43 1 0 21 2 1 0 39 34 1 0 20 15 1 0 1 44 1 0 1 45 1 0 1 46 1 0 2 47 1 6 3 48 1 0 4 49 1 0 6 50 1 0 6 51 1 0 6 52 1 0 7 53 1 0 7 54 1 0 7 55 1 0 10 56 1 0 10 57 1 0 11 58 1 6 13 59 1 0 13 60 1 0 14 61 1 1 15 62 1 6 16 63 1 6 17 64 1 6 18 65 1 0 18 66 1 0 18 67 1 0 19 68 1 0 19 69 1 0 26 70 1 0 26 71 1 0 26 72 1 0 30 73 1 0 30 74 1 0 30 75 1 0 35 76 1 0 36 77 1 0 37 78 1 0 38 79 1 0 39 80 1 0 43 81 1 0 43 82 1 0 43 83 1 0 M END

Standard InCHIKey	PDRWXFDCQXKDSK-REVJNMIYSA-N
Standard InCHI	InChI=1S/C33H40O10/c1-18-14-15-32(7,8)26(37)16-25(40-21(4)34)20(3)29(42-31(39)24-12-10-9-11-13-24)27-28(41-22(5)35)19(2)17-33(27,30(18)38)43-23(6)36/h9-15,18-19,25,27-29H,3,16-17H2,1-2,4-8H3/b15-14+/t18-,19-,25+,27+,28-,29-,33+/m0/s1
SMILES	C[C@H]1/C=C/C(C)(C)C(=O)C[C@H](C(=C)[C@@H]([C@H]2[C@H]([C@@H](C)C[C@@]2(C1=O)OC(=O)C)OC(=O)C)OC(=O)c1ccccc1)OC(=O)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	596.26	Volume:	612.556 ? Van der Waals volume.
Dense:	0.973	LogP:	2.961 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.985 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.312 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	9.0	Rigid Bonds:	29.0
TPSA:	139.34 ? Topological Polar Surface Area.	H-Bond Acceptor:	10.0
H-Bond Donor:	0.0	Rings:	3.0
Heavy Atoms:	10.0

MedChem Properties

QED Drug-Likeness Score:	0.274	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.386	Fsp³:	0.515
MCE-18:	98.6 ? 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:	0.793	Fluc inhibitor:	0.003 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.01 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.03 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.312	Promiscuous compounds:	0.185

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.128	MDCK Permeability:	-4.738
Pgp-inhibitor:	1.0	Pgp-substrate:	0.004
PAMPA:	0.061 ? 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%):	0.375	30% Bioavailability (F30%):	0.87
50% Bioavailability (F50%):	0.968

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.998
Plasma Protein Binding (PPB):	93.456%	Volume Distribution (VD):	-0.125
Fu:	7.962% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.999	BCRP inhibitor:	0.007
BSEP inhibitor:	1.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.008
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.002
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.025
CYP3A4-inhibitor:	0.067	CYP3A4-substrate:	0.722
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.973 ? 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):

6.057

Half-life (T1/2):

0.498

ADMET: Toxicity

hERG Blockers:	0.009	hERG Blockers (10um):	0.115
Human Hepatotoxicity (H-HT):	0.602	Drug-induced Liver Injury (DILI):	0.998
AMES Toxicity:	0.95	Rat Oral Acute Toxicity:	0.266
Maximum Recommended Daily Dose:	0.389	Skin Sensitization:	1.0
Carcinogencity:	0.843	Eye Corrosion:	0.007
Eye Irritation:	0.38	Respiratory Toxicity:	0.231
Drug-induced Neurotoxicity:	0.924	Ototoxicity:	0.294
Hematotoxicity:	0.581	Drug-induced Nephrotoxicity:	0.977
Genotoxicity:	0.999	RPMI-8226 Immunitoxicity:	0.181
A549 Cytotoxicity:	0.748	Hek293 Cytotoxicity:	0.739
BCF:	0.697 ? 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:	3.54 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.153 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.768 ? 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
NPO40845	Euphorbia glomerulans	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[30860373]

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
Ratio IC50	1
IC50	3

Activity Type	# Activity
Cell line	2
Individual protein	2

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT668	Individual protein	P-glycoprotein 1	Homo sapiens	Ratio IC50	=	4.6	n.a.	PMID[30860373]
NPT668	Individual protein	P-glycoprotein 1	Homo sapiens	IC50	=	14200.0	nM	PMID[30860373]

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT378	Cell line	NCI/ADR-RES	Homo sapiens	IC50	>	100000.0	nM	PMID[30860373]
NPT83	Cell line	MCF7	Homo sapiens	IC50	>	100000.0	nM	PMID[30860373]

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 NPC482307 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	14245
0.1-0.2	33321
0.2-0.3	1788
0.3-0.4	395
0.4-0.5	66
0.5-0.6	23
0.6-0.7	12
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
0.8824	High Similarity	NPC482308
0.7917	Intermediate Similarity	NPC482314
0.7368	Intermediate Similarity	NPC482301
0.72	Intermediate Similarity	NPC86772
0.7105	Intermediate Similarity	NPC290833
0.7105	Intermediate Similarity	NPC482249
0.6974	Remote Similarity	NPC482300
0.6892	Remote Similarity	NPC196683
0.6753	Remote Similarity	NPC482315
0.6667	Remote Similarity	NPC265459
0.6667	Remote Similarity	NPC482265
0.6623	Remote Similarity	NPC325805
0.6528	Remote Similarity	NPC470188
0.65	Remote Similarity	NPC482310
0.65	Remote Similarity	NPC482302
0.642	Remote Similarity	NPC482252
0.625	Remote Similarity	NPC475262
0.625	Remote Similarity	NPC482304
0.5909	Remote Similarity	NPC482258
0.5904	Remote Similarity	NPC482272
0.5663	Remote Similarity	NPC82467
0.5663	Remote Similarity	NPC482270
0.5568	Remote Similarity	NPC482250
0.5568	Remote Similarity	NPC470190
0.5542	Remote Similarity	NPC276652
0.5541	Remote Similarity	NPC105725
0.5529	Remote Similarity	NPC205389
0.5455	Remote Similarity	NPC317191
0.5366	Remote Similarity	NPC153617
0.5357	Remote Similarity	NPC604953
0.5357	Remote Similarity	NPC605971
0.5349	Remote Similarity	NPC482268
0.5349	Remote Similarity	NPC482269
0.5294	Remote Similarity	NPC272523
0.5233	Remote Similarity	NPC482251
0.5176	Remote Similarity	NPC600781
0.5176	Remote Similarity	NPC611288
0.5132	Remote Similarity	NPC49393
0.5119	Remote Similarity	NPC42234
0.5116	Remote Similarity	NPC242355
0.5114	Remote Similarity	NPC482263

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC482307 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4381
0.1-0.2	4679
0.2-0.3	89
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