NPASS Compound

Natural Product: NPC488654

Natural Product ID	NPC488654
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	VVYSQKPHSHRIBJ-IXSFYWCRSA-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 77 79 0 0 0 0 0 0 0 0999 V2000 4.7885 5.0185 -0.4942 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6591 3.7364 -0.3583 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4842 2.9772 -0.7380 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4487 1.6539 -0.5555 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2753 0.8127 -0.9212 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7425 0.0379 0.2906 C 0 0 2 0 0 0 0 0 0 0 0 0 1.3450 1.0399 1.2906 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8969 -0.7837 0.8580 C 0 0 2 0 0 0 0 0 0 0 0 0 3.6961 -1.4979 -0.1660 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4918 -1.7268 1.9289 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0563 -2.0728 2.0333 C 0 0 1 0 0 0 0 0 0 0 0 0 0.3744 -2.0566 0.6998 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.1100 -2.3163 0.8500 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0287 -1.3711 0.6355 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6008 0.0100 0.2236 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.5043 -0.2378 -0.7907 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7060 -0.9137 -0.1907 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.6858 0.5745 -0.4850 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2778 1.7744 -0.1428 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8109 2.3796 0.8542 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.4070 2.3714 -0.8717 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8110 3.6780 -0.2476 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9723 4.2867 -1.0012 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1165 3.5672 1.2098 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1746 -3.7458 1.2163 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.3490 -4.3507 0.7468 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.1382 -4.8806 1.7372 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0480 -4.3314 0.7743 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6992 -3.4353 0.0778 C 0 0 1 0 0 0 0 0 0 0 0 0 0.4446 -3.4366 -1.3121 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4292 -3.7629 -2.2309 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5693 -4.0634 -1.8016 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2108 -3.7769 -3.6919 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0099 -3.4052 2.5340 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2973 3.6162 -1.3416 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0505 5.6847 -0.9021 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7129 5.5244 -0.1822 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5201 3.1981 0.0821 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3368 1.2234 -0.1183 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3956 0.2113 -1.8122 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4652 1.5710 -1.1418 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7204 1.8660 0.8293 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7793 0.7328 2.1600 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2405 1.5969 1.6935 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5650 0.0003 1.3313 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7476 -1.1073 -0.2040 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8426 -2.5760 0.1389 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3066 -1.4916 -1.1829 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8087 -1.3470 2.9489 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0813 -2.6913 1.8456 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4942 -1.5172 2.8161 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0756 -1.5605 0.7487 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3479 0.6703 1.0383 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9557 -0.9956 -1.5011 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2172 0.6052 -1.3839 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2047 -1.3924 -1.1005 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0661 2.6038 -1.9172 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2552 1.6612 -0.9518 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9420 4.3677 -0.3638 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6044 3.4608 -1.3717 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5709 4.9503 -0.3286 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5650 4.8319 -1.8666 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2847 2.5212 1.4993 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0108 4.1861 1.4594 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2886 3.9597 1.8331 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2295 -3.8811 2.3254 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4711 -4.1076 2.4704 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6269 -5.7126 2.2899 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0091 -5.3529 1.2387 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7594 -3.7150 0.2279 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8937 -4.8152 -3.9657 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4992 -3.0064 -4.0420 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1910 -3.6209 -4.2156 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4256 -3.3407 3.4412 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0051 3.1333 -2.3046 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4677 4.6888 -1.5470 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4166 3.6134 -0.6342 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 2 3 1 0 3 4 2 0 4 5 1 0 6 5 1 6 6 7 1 0 6 8 1 0 8 9 1 0 8 10 1 0 10 11 1 0 11 12 1 0 12 13 1 1 13 14 2 0 14 15 1 0 15 16 1 0 16 17 1 0 15 18 1 0 18 19 1 0 19 20 2 0 19 21 1 0 21 22 1 0 22 23 1 0 22 24 1 0 13 25 1 0 25 26 1 0 26 27 1 0 25 28 1 0 28 29 1 0 29 30 1 0 30 31 1 0 31 32 2 0 31 33 1 0 11 34 1 0 3 35 1 0 17 6 1 0 17 12 1 0 29 12 1 0 1 36 1 0 1 37 1 0 2 38 1 0 4 39 1 0 5 40 1 0 5 41 1 0 7 42 1 0 7 43 1 0 7 44 1 0 8 45 1 1 9 46 1 0 9 47 1 0 9 48 1 0 10 49 1 0 10 50 1 0 11 51 1 1 14 52 1 0 15 53 1 1 16 54 1 0 16 55 1 0 17 56 1 6 21 57 1 0 21 58 1 0 22 59 1 0 23 60 1 0 23 61 1 0 23 62 1 0 24 63 1 0 24 64 1 0 24 65 1 0 25 66 1 1 27 67 1 0 27 68 1 0 27 69 1 0 29 70 1 6 33 71 1 0 33 72 1 0 33 73 1 0 34 74 1 0 35 75 1 0 35 76 1 0 35 77 1 0 M END

Standard InCHIKey	VVYSQKPHSHRIBJ-IXSFYWCRSA-N
Standard InCHI	InChI=1S/C28H42O7/c1-9-17(4)10-11-27(7)18(5)13-23(30)28-21(25(32-8)35-26(28)33-19(6)29)14-20(15-22(27)28)34-24(31)12-16(2)3/h9-10,14,16,18,20,22-23,25-26,30H,1,11-13,15H2,2-8H3/b17-10+/t18-,20+,22+,23+,25+,26-,27-,28-/m1/s1
SMILES	C=C/C(=C/C[C@]1(C)[C@H](C)C[C@@H]([C@@]23C(=C[C@@H](C[C@@H]12)OC(=O)CC(C)C)[C@@H](OC)O[C@H]3OC(=O)C)O)/C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	490.29	Volume:	515.524 ? Van der Waals volume.
Dense:	0.951	LogP:	3.886 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.597 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.131 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	10.0	Rigid Bonds:	19.0
TPSA:	91.29 ? Topological Polar Surface Area.	H-Bond Acceptor:	7.0
H-Bond Donor:	1.0	Rings:	3.0
Heavy Atoms:	7.0

MedChem Properties

QED Drug-Likeness Score:	0.3	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.776	Fsp³:	0.714
MCE-18:	88.833 ? 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:	Rejected	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.671	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.004 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.001 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.331	Promiscuous compounds:	0.567

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.987	MDCK Permeability:	-4.808
Pgp-inhibitor:	0.038	Pgp-substrate:	0.89
PAMPA:	0.62 ? 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):	0.007
20% Bioavailability (F20%):	0.962	30% Bioavailability (F30%):	0.956
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.04	MRP1:	0.915
Plasma Protein Binding (PPB):	74.102%	Volume Distribution (VD):	-0.021
Fu:	17.805% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.999
OATP1B3 inhibitor:	0.964	BCRP inhibitor:	0.127
BSEP inhibitor:	0.991

ADMET: Metabolism

CYP1A2-inhibitor:	0.195	CYP1A2-substrate:	0.964
CYP2C19-inhibitor:	0.771	CYP2C19-substrate:	0.28
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.03
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.049
CYP3A4-inhibitor:	0.173	CYP3A4-substrate:	0.821
CYP2B6-substrate:	0.009	CYP2C8-inhibitor:	0.999
HLM stability:	0.997 ? 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):

8.256

Half-life (T1/2):

1.107

ADMET: Toxicity

hERG Blockers:	0.157	hERG Blockers (10um):	0.558
Human Hepatotoxicity (H-HT):	0.604	Drug-induced Liver Injury (DILI):	0.707
AMES Toxicity:	0.922	Rat Oral Acute Toxicity:	0.967
Maximum Recommended Daily Dose:	0.994	Skin Sensitization:	0.974
Carcinogencity:	0.649	Eye Corrosion:	0.0
Eye Irritation:	0.031	Respiratory Toxicity:	0.982
Drug-induced Neurotoxicity:	0.897	Ototoxicity:	0.791
Hematotoxicity:	0.742	Drug-induced Nephrotoxicity:	0.882
Genotoxicity:	0.974	RPMI-8226 Immunitoxicity:	0.439
A549 Cytotoxicity:	0.684	Hek293 Cytotoxicity:	0.389
BCF:	1.256 ? 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:	3.904 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.693 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.054 ? 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
NPO40063	Casearia graveolens	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26474353]
NPO40063	Casearia graveolens	Species	Salicaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[31916761]

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	2

Activity Type	# Activity
Cell line	2

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
NPT81	Cell line	A549	Homo sapiens	IC50	>	10000.0	nM	PMID[31916761]
NPT65	Cell line	HepG2	Homo sapiens	IC50	>	10000.0	nM	PMID[31916761]

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 NPC488654 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	17667
0.1-0.2	28300
0.2-0.3	3747
0.3-0.4	42
0.4-0.5	41
0.5-0.6	21
0.6-0.7	11
0.7-0.8	0
0.8-0.85	7
0.85-0.9	7
0.9-0.95	6
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.9322	High Similarity	NPC81567
0.9322	High Similarity	NPC488652
0.931	High Similarity	NPC488653
0.9138	High Similarity	NPC488659
0.9138	High Similarity	NPC604149
0.9	High Similarity	NPC134270
0.8689	High Similarity	NPC488660
0.8689	High Similarity	NPC488657
0.8689	High Similarity	NPC609880
0.8571	High Similarity	NPC252296
0.8548	High Similarity	NPC488658
0.8548	High Similarity	NPC488655
0.85	High Similarity	NPC602188
0.8387	Intermediate Similarity	NPC201880
0.8254	Intermediate Similarity	NPC609715
0.8095	Intermediate Similarity	NPC329623
0.8095	Intermediate Similarity	NPC609711
0.8065	Intermediate Similarity	NPC488656
0.8	Intermediate Similarity	NPC488964
0.8	Intermediate Similarity	NPC184512
0.7969	Intermediate Similarity	NPC330003
0.7969	Intermediate Similarity	NPC470321
0.7969	Intermediate Similarity	NPC264867
0.7969	Intermediate Similarity	NPC473207
0.7812	Intermediate Similarity	NPC479491
0.7273	Intermediate Similarity	NPC479940
0.7273	Intermediate Similarity	NPC316974
0.7273	Intermediate Similarity	NPC479497
0.7015	Intermediate Similarity	NPC311223
0.68	Remote Similarity	NPC109376
0.6716	Remote Similarity	NPC479943
0.6667	Remote Similarity	NPC238397
0.662	Remote Similarity	NPC119550
0.6533	Remote Similarity	NPC116292
0.6522	Remote Similarity	NPC7644
0.6197	Remote Similarity	NPC475889
0.6197	Remote Similarity	NPC7613
0.6197	Remote Similarity	NPC479942
0.6111	Remote Similarity	NPC479941
0.6027	Remote Similarity	NPC471363
0.5942	Remote Similarity	NPC600724
0.5867	Remote Similarity	NPC127933
0.5833	Remote Similarity	NPC128795
0.5797	Remote Similarity	NPC606965
0.5758	Remote Similarity	NPC604446
0.5735	Remote Similarity	NPC603601
0.55	Remote Similarity	NPC179128
0.5479	Remote Similarity	NPC473204
0.5417	Remote Similarity	NPC88507
0.5417	Remote Similarity	NPC488235
0.5402	Remote Similarity	NPC320734
0.5366	Remote Similarity	NPC486751
0.5357	Remote Similarity	NPC224660
0.5333	Remote Similarity	NPC217921
0.5333	Remote Similarity	NPC135015
0.52	Remote Similarity	NPC311166
0.5181	Remote Similarity	NPC316708
0.5132	Remote Similarity	NPC88013
0.5132	Remote Similarity	NPC218158
0.5122	Remote Similarity	NPC87630
0.5114	Remote Similarity	NPC481025

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC488654 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6816
0.1-0.2	2307
0.2-0.3	27
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