NPASS Compound

Natural Product: NPC473531

Natural Product ID	NPC473531
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	[(2S,3R,4R,5S,6R)-4,5-Diacetyloxy-6-[[9-(1,3-Benzodioxol-5-Yl)-6,7-Dimethoxy-1-Oxo-3H-Benzo[F][2]Benzofuran-4-Yl]Oxy]-2-Methyloxan-3-Yl] Acetate
IUPAC Name	[(2S,3R,4R,5S,6R)-4,5-diacetyloxy-6-[[9-(1,3-benzodioxol-5-yl)-6,7-dimethoxy-1-oxo-3H-benzo[f][2]benzofuran-4-yl]oxy]-2-methyloxan-3-yl] acetate
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL444750
PubChem CID	11285224
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0001392] Lignans, neolignans and related compounds [CHEMONTID:0001511] Lignan glycosides

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 84 0 0 0 0 0 0 0 0999 V2000 -2.9356 -1.9799 2.1302 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1018 -2.0277 0.6104 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3410 -1.2774 0.2725 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0674 0.1973 0.4807 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9702 0.5028 -0.5240 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7699 -0.2496 -0.1065 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9528 -1.5940 0.0466 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7035 -0.0226 -0.9942 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6009 0.2636 -0.6414 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9837 1.5631 -0.3907 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2245 2.8589 -0.3926 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1501 3.8614 -0.1118 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4052 3.3507 0.1462 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4764 3.9177 0.4710 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2717 1.9070 -0.0373 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1937 0.8795 0.0628 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8830 -0.4440 -0.1729 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8511 -1.4251 -0.0683 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5510 -2.7297 -0.3132 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2627 -3.0321 -0.6652 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2850 -2.0404 -0.7708 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5812 -0.7323 -0.5253 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9711 -4.3746 -0.9133 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6630 -4.7365 -1.2779 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5449 -3.7001 -0.2005 O 0 0 0 0 0 0 0 0 0 0 0 0 5.8634 -3.4093 0.1579 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5821 1.2066 0.4399 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4918 1.4936 -0.5365 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7857 1.7980 -0.1789 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1786 1.8185 1.1415 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2466 1.5263 2.1104 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9541 1.2220 1.7576 C 0 0 0 0 0 0 0 0 0 0 0 0 8.5229 2.1537 1.1913 O 0 0 0 0 0 0 0 0 0 0 0 0 8.8866 2.5783 -0.0938 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8755 2.1194 -0.9710 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8018 1.8377 -0.7853 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0587 2.4030 -2.0225 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4628 1.6205 -2.9179 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8491 3.8580 -2.2165 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2089 0.9957 0.2884 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.6311 1.8057 1.3386 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0133 1.8311 2.4394 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.8320 2.6896 1.2323 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4488 -1.7488 0.9630 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.5782 -2.2917 0.3591 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5812 -2.3534 -0.9080 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.7521 -2.7918 1.0793 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4005 -2.8781 2.5017 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3480 -1.0628 2.3906 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9365 -1.9795 2.6034 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2585 -3.0967 0.3546 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5124 -1.4076 -0.8356 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6121 0.3020 1.4804 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3355 0.0179 -1.4822 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4289 0.1257 0.9031 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2064 3.0072 -1.3880 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5616 2.7722 0.3966 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8641 -1.0941 0.2205 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3079 -2.3267 -1.0605 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3722 -4.1274 -2.1524 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0331 -4.4737 -0.4556 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6352 -5.8200 -1.5028 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9576 -2.9748 1.1760 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2666 -2.6538 -0.5786 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4936 -4.3058 0.0240 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2357 1.4935 -1.6183 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5381 1.5390 3.1325 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2654 1.0000 2.5762 H 0 0 0 0 0 0 0 0 0 0 0 0 9.8751 2.1330 -0.3952 H 0 0 0 0 0 0 0 0 0 0 0 0 8.9617 3.6872 -0.1143 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6471 4.2399 -2.9192 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9966 4.4252 -1.2823 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8930 4.0734 -2.7247 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4767 2.3115 0.4042 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4524 2.6544 2.1534 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5453 3.7576 1.0926 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.7744 -3.8737 1.2255 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.6557 -2.5479 0.4474 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.9247 -2.2163 2.0283 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 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 2 0 10 11 1 0 11 12 1 0 12 13 1 0 13 14 2 0 13 15 1 0 15 16 2 0 16 17 1 0 17 18 2 0 18 19 1 0 19 20 2 0 20 21 1 0 21 22 2 0 20 23 1 0 23 24 1 0 19 25 1 0 25 26 1 0 16 27 1 0 27 28 2 0 28 29 1 0 29 30 2 0 30 31 1 0 31 32 2 0 30 33 1 0 33 34 1 0 34 35 1 0 5 36 1 0 36 37 1 0 37 38 2 0 37 39 1 0 4 40 1 0 40 41 1 0 41 42 2 0 41 43 1 0 3 44 1 0 44 45 1 0 45 46 2 0 45 47 1 0 7 2 1 0 22 9 1 0 15 10 1 0 22 17 1 0 32 27 1 0 35 29 1 0 1 48 1 0 1 49 1 0 1 50 1 0 2 51 1 0 3 52 1 0 4 53 1 0 5 54 1 0 6 55 1 0 11 56 1 0 11 57 1 0 18 58 1 0 21 59 1 0 24 60 1 0 24 61 1 0 24 62 1 0 26 63 1 0 26 64 1 0 26 65 1 0 28 66 1 0 31 67 1 0 32 68 1 0 34 69 1 0 34 70 1 0 39 71 1 0 39 72 1 0 39 73 1 0 43 74 1 0 43 75 1 0 43 76 1 0 47 77 1 0 47 78 1 0 47 79 1 0 M END

Standard InCHIKey	BWGZOLFCSSJAKB-SNNYXJDNSA-N
Standard InCHI	InChI=1S/C33H32O14/c1-14-28(44-15(2)34)30(45-16(3)35)31(46-17(4)36)33(43-14)47-29-20-11-24(39-6)23(38-5)10-19(20)26(27-21(29)12-40-32(27)37)18-7-8-22-25(9-18)42-13-41-22/h7-11,14,28,30-31,33H,12-13H2,1-6H3/t14-,28+,30+,31-,33+/m0/s1
SMILES	CC1C(C(C(C(O1)OC2=C3COC(=O)C3=C(C4=CC(=C(C=C42)OC)OC)C5=CC6=C(C=C5)OCO6)OC(=O)C)OC(=O)C)OC(=O)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	652.18	Volume:	619.411 ? Van der Waals volume.
Dense:	1.053	LogP:	3.138 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.038 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.021 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	11.0	Rigid Bonds:	35.0
TPSA:	160.58 ? Topological Polar Surface Area.	H-Bond Acceptor:	14.0
H-Bond Donor:	0.0	Rings:	6.0
Heavy Atoms:	14.0

MedChem Properties

QED Drug-Likeness Score:	0.255	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.369	Fsp³:	0.394
MCE-18:	125.565 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected	GSK Rule:	Accepted
Golden Triangle Rule:	Accepted	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.553	Fluc inhibitor:	0.007 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.753 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.333 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.118	Promiscuous compounds:	0.198

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.937	MDCK Permeability:	-4.595
Pgp-inhibitor:	0.952	Pgp-substrate:	0.799
PAMPA:	0.905 ? 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):	0.337
20% Bioavailability (F20%):	0.471	30% Bioavailability (F30%):	0.072
50% Bioavailability (F50%):	0.992

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.001	MRP1:	0.983
Plasma Protein Binding (PPB):	97.128%	Volume Distribution (VD):	-0.207
Fu:	3.541% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.937
OATP1B3 inhibitor:	0.996	BCRP inhibitor:	0.151
BSEP inhibitor:	1.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.157	CYP1A2-substrate:	0.108
CYP2C19-inhibitor:	0.984	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.001	CYP2C9-substrate:	1.0
CYP2D6-inhibitor:	0.01	CYP2D6-substrate:	0.895
CYP3A4-inhibitor:	0.122	CYP3A4-substrate:	0.057
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.996
HLM stability:	0.819 ? 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):

1.827

Half-life (T1/2):

1.331

ADMET: Toxicity

hERG Blockers:	0.098	hERG Blockers (10um):	0.472
Human Hepatotoxicity (H-HT):	0.888	Drug-induced Liver Injury (DILI):	0.995
AMES Toxicity:	0.94	Rat Oral Acute Toxicity:	0.644
Maximum Recommended Daily Dose:	0.892	Skin Sensitization:	0.969
Carcinogencity:	0.925	Eye Corrosion:	0.0
Eye Irritation:	0.003	Respiratory Toxicity:	0.044
Drug-induced Neurotoxicity:	0.722	Ototoxicity:	0.895
Hematotoxicity:	0.936	Drug-induced Nephrotoxicity:	0.914
Genotoxicity:	0.99	RPMI-8226 Immunitoxicity:	0.285
A549 Cytotoxicity:	0.327	Hek293 Cytotoxicity:	0.723
BCF:	0.993 ? 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:	3.845 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.089 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.217 ? 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
NPO20590	Justicia patentiflora	Species	Acanthaceae	Eukaryota	n.a.	Vietnamese	n.a.	PMID[15921419]
NPO20590	Justicia patentiflora	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20590	Justicia patentiflora	Species	Acanthaceae	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	3

Activity Type	# Activity
Cell line	3

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
NPT91	Cell line	KB	Homo sapiens	IC50	=	20.0	nM	PMID[7525959]
NPT83	Cell line	MCF7	Homo sapiens	IC50	=	45.0	nM	PMID[26026364]
NPT393	Cell line	HCT-116	Homo sapiens	IC50	=	35.0	nM	PMID[11520227]

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 NPC473531 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	19885
0.1-0.2	29189
0.2-0.3	728
0.3-0.4	15
0.4-0.5	11
0.5-0.6	6
0.6-0.7	19
0.7-0.8	0
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8125	Intermediate Similarity	NPC471923
0.8095	Intermediate Similarity	NPC473697
0.7176	Intermediate Similarity	NPC292712
0.6944	Remote Similarity	NPC239113
0.686	Remote Similarity	NPC471921
0.6782	Remote Similarity	NPC471922
0.6712	Remote Similarity	NPC19600
0.6706	Remote Similarity	NPC114550
0.6706	Remote Similarity	NPC312006
0.6706	Remote Similarity	NPC602979
0.6705	Remote Similarity	NPC471920
0.6471	Remote Similarity	NPC474075
0.6471	Remote Similarity	NPC483381
0.6437	Remote Similarity	NPC129930
0.6437	Remote Similarity	NPC20114
0.6421	Remote Similarity	NPC275690
0.6395	Remote Similarity	NPC184624
0.6267	Remote Similarity	NPC115123
0.6263	Remote Similarity	NPC161609
0.6211	Remote Similarity	NPC35266
0.6211	Remote Similarity	NPC167045
0.6211	Remote Similarity	NPC114120
0.5769	Remote Similarity	NPC78944
0.557	Remote Similarity	NPC15212
0.5413	Remote Similarity	NPC286301
0.5413	Remote Similarity	NPC313063
0.5122	Remote Similarity	NPC22130
0.5062	Remote Similarity	NPC299820

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC473531 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5099
0.1-0.2	4028
0.2-0.3	22
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