NPASS Compound

Natural Product: NPC470916

Natural Product ID	NPC470916
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Schisphenin A
IUPAC Name	n.a.
Synonyms	Schisphenin A
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL2313595
PubChem CID	71566721
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000238] Tannins [CHEMONTID:0001710] Hydrolyzable tannins

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 73 75 0 0 0 0 0 0 0 0999 V2000 6.2929 -1.6533 -0.4459 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4947 -1.9637 -1.6453 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2701 -1.5298 -1.8240 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5437 -1.8986 -3.0729 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6553 -0.7016 -0.7999 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2606 -0.3909 0.2473 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3451 -0.2103 -0.9418 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7502 0.5937 0.0581 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5591 -0.0761 0.6199 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9663 -1.1240 1.4184 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0755 -1.9170 2.1049 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2841 -1.6700 2.0073 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7559 -0.6421 1.2325 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8380 0.1157 0.5632 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6622 1.0475 -0.1976 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6393 0.2609 -0.7334 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6034 0.9099 -1.4640 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5883 2.2822 -1.6555 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5716 3.0407 -1.0979 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5963 2.4453 -0.3649 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5891 3.4662 0.0831 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6603 2.7402 0.5817 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3609 1.9501 -0.4687 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5994 2.6779 -0.9929 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5209 1.8386 -1.5765 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5683 3.8365 1.1386 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5814 2.9069 -2.4009 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.6296 0.1241 -2.0248 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.7900 -0.0825 -1.2340 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5663 -1.0973 -0.5143 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8729 -1.9771 -1.3989 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0859 -0.3103 1.0972 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.7372 0.6194 1.9574 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1721 -2.4868 2.7129 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7361 -3.6559 2.2065 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4989 -2.9760 2.9069 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8280 -3.3441 3.1008 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8640 -2.0353 0.5024 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3117 -2.1189 -0.5147 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4954 -0.5682 -0.3140 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9405 -2.5797 -2.4160 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6000 -1.3454 -3.1621 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2282 -1.6807 -3.9335 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3593 -2.9973 -3.0118 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4627 0.7379 0.9259 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0249 -1.3279 1.5072 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5215 4.1315 -1.2283 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2834 4.0186 -0.8267 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9958 4.0653 0.8910 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3287 2.1410 1.4558 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2658 3.5639 -1.5565 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2655 3.0007 -0.1909 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1149 2.0047 -1.7126 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6394 0.9368 -2.0021 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9632 4.4544 1.8355 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4033 3.4167 1.7249 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9082 4.5170 0.3252 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1873 3.5597 -1.8985 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7414 -1.1417 -0.8872 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8151 0.6040 -0.3492 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7127 0.0553 -1.8361 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6350 -2.7248 -1.7252 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0094 -2.4594 -0.9094 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5287 -1.4565 -2.3154 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7746 0.3133 2.1442 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6608 1.6498 1.5974 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2021 0.5811 2.9411 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8333 -3.7170 2.4529 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2722 -4.5192 2.7474 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5405 -3.8140 1.1331 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8405 -4.4326 3.3824 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3559 -2.7562 3.8859 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3912 -3.2252 2.1551 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 3 5 1 0 5 6 2 0 5 7 1 0 7 8 1 0 8 9 1 0 9 10 2 0 10 11 1 0 11 12 2 0 12 13 1 0 13 14 2 0 14 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 1 0 22 23 1 0 23 24 1 0 23 25 1 0 22 26 1 0 18 27 1 0 17 28 1 0 28 29 1 0 16 30 1 0 30 31 1 0 13 32 1 0 32 33 1 0 12 34 1 0 34 35 1 0 11 36 1 0 36 37 1 0 23 8 1 0 14 9 1 0 20 15 1 0 1 38 1 0 1 39 1 0 1 40 1 0 2 41 1 0 4 42 1 0 4 43 1 0 4 44 1 0 8 45 1 0 10 46 1 0 19 47 1 0 21 48 1 0 21 49 1 0 22 50 1 0 24 51 1 0 24 52 1 0 24 53 1 0 25 54 1 0 26 55 1 0 26 56 1 0 26 57 1 0 27 58 1 0 29 59 1 0 29 60 1 0 29 61 1 0 31 62 1 0 31 63 1 0 31 64 1 0 33 65 1 0 33 66 1 0 33 67 1 0 35 68 1 0 35 69 1 0 35 70 1 0 37 71 1 0 37 72 1 0 37 73 1 0 M END

Standard InCHIKey	OYEBDFXJPSZPAU-MOROAYOKSA-N
Standard InCHI	InChI=1S/C28H36O9/c1-10-14(2)27(30)37-26-17-13-19(32-5)23(34-7)25(36-9)21(17)20-16(11-15(3)28(26,4)31)12-18(29)22(33-6)24(20)35-8/h10,12-13,15,26,29,31H,11H2,1-9H3/b14-10+/t15-,26-,28-/m0/s1
SMILES	CC=C(C)C(=O)OC1C2=CC(=C(C(=C2C3=C(C(=C(C=C3CC(C1(C)O)C)O)OC)OC)OC)OC)OC

Calculated Properties

Physi-Chem Properties

Molecular Weight:	516.24	Volume:	525.195 ? Van der Waals volume.
Dense:	0.983	LogP:	2.724 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.862 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.188 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	8.0	Rigid Bonds:	20.0
TPSA:	112.91 ? Topological Polar Surface Area.	H-Bond Acceptor:	9.0
H-Bond Donor:	2.0	Rings:	3.0
Heavy Atoms:	9.0

MedChem Properties

QED Drug-Likeness Score:	0.403	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.1	Fsp³:	0.464
MCE-18:	83.073 ? 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:	1	PAINS Alert:	0
Colloidal aggregators:	0.046	Fluc inhibitor:	0.215 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.122 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.645 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.241	Promiscuous compounds:	0.172

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.989	MDCK Permeability:	-4.766
Pgp-inhibitor:	0.098	Pgp-substrate:	0.26
PAMPA:	0.37 ? 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):	0.025
20% Bioavailability (F20%):	0.204	30% Bioavailability (F30%):	0.25
50% Bioavailability (F50%):	0.955

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.268	MRP1:	0.999
Plasma Protein Binding (PPB):	90.788%	Volume Distribution (VD):	-0.062
Fu:	10.524% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.684
OATP1B3 inhibitor:	0.982	BCRP inhibitor:	0.118
BSEP inhibitor:	0.935

ADMET: Metabolism

CYP1A2-inhibitor:	0.96	CYP1A2-substrate:	0.064
CYP2C19-inhibitor:	0.998	CYP2C19-substrate:	0.069
CYP2C9-inhibitor:	0.533	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.138	CYP2D6-substrate:	0.498
CYP3A4-inhibitor:	0.999	CYP3A4-substrate:	0.036
CYP2B6-substrate:	0.002	CYP2C8-inhibitor:	0.831
HLM stability:	0.676 ? 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):

3.688

Half-life (T1/2):

1.257

ADMET: Toxicity

hERG Blockers:	0.2	hERG Blockers (10um):	0.622
Human Hepatotoxicity (H-HT):	0.508	Drug-induced Liver Injury (DILI):	0.404
AMES Toxicity:	0.432	Rat Oral Acute Toxicity:	0.36
Maximum Recommended Daily Dose:	0.769	Skin Sensitization:	0.948
Carcinogencity:	0.755	Eye Corrosion:	0.001
Eye Irritation:	0.139	Respiratory Toxicity:	0.758
Drug-induced Neurotoxicity:	0.678	Ototoxicity:	0.704
Hematotoxicity:	0.402	Drug-induced Nephrotoxicity:	0.624
Genotoxicity:	0.169	RPMI-8226 Immunitoxicity:	0.305
A549 Cytotoxicity:	0.474	Hek293 Cytotoxicity:	0.617
BCF:	1.593 ? 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:	3.828 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.405 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.536 ? 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
NPO8584	Schisandra arisanensis	Species	Schisandraceae	Eukaryota	fruits	n.a.	n.a.	PMID[19673515]
NPO8584	Schisandra arisanensis	Species	Schisandraceae	Eukaryota	fruits	n.a.	n.a.	PMID[20536188]
NPO8584	Schisandra arisanensis	Species	Schisandraceae	Eukaryota	fruits	n.a.	n.a.	PMID[23265871]
NPO7385	Schisandra sphenanthera	Species	Schisandraceae	Eukaryota	fruits	n.a.	n.a.	PMID[23265871]
NPO8584	Schisandra arisanensis	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7385	Schisandra sphenanthera	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7385	Schisandra sphenanthera	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8584	Schisandra arisanensis	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7385	Schisandra sphenanthera	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8584	Schisandra arisanensis	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7385	Schisandra sphenanthera	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO7385	Schisandra sphenanthera	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO8584	Schisandra arisanensis	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7385	Schisandra sphenanthera	Species	Schisandraceae	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
Inhibition	1

Activity Type	# Activity
Others	1

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
NPT2	Others	Unspecified	n.a.	Inhibition	=	43.2	%	Open TG-GATES in vivo data: Organ Weight

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 NPC470916 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	9995
0.1-0.2	35385
0.2-0.3	4282
0.3-0.4	114
0.4-0.5	54
0.5-0.6	10
0.6-0.7	4
0.7-0.8	0
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8333	Intermediate Similarity	NPC295297
0.7463	Intermediate Similarity	NPC126405
0.7463	Intermediate Similarity	NPC53669
0.7463	Intermediate Similarity	NPC77237
0.7463	Intermediate Similarity	NPC297271
0.7463	Intermediate Similarity	NPC16791
0.7463	Intermediate Similarity	NPC217708
0.7164	Intermediate Similarity	NPC198461
0.6986	Remote Similarity	NPC485504
0.6761	Remote Similarity	NPC42797
0.6094	Remote Similarity	NPC240279
0.6027	Remote Similarity	NPC224472
0.5833	Remote Similarity	NPC308739
0.5443	Remote Similarity	NPC29727
0.5405	Remote Similarity	NPC471154
0.5238	Remote Similarity	NPC214853
0.5205	Remote Similarity	NPC471183
0.519	Remote Similarity	NPC475592
0.5147	Remote Similarity	NPC87883
0.5072	Remote Similarity	NPC46277
0.5068	Remote Similarity	NPC474393
0.5068	Remote Similarity	NPC474347

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC470916 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3458
0.1-0.2	5558
0.2-0.3	134
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