NPASS Compound

Natural Product: NPC515784

Natural Product ID	NPC515784
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	EiM08-29243
IUPAC Name	(5~{a}~{S},8~{a}~{S},9~{S})-9-(3,4,5-trimethoxyphenyl)-5~{a},6,8~{a},9-tetrahydroisobenzofuro[5,6-f][1,3]benzodioxole-5,8-dione
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 50 54 0 0 0 0 0 0 0 0999 V2000 -2.0288 -0.2856 3.7508 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8531 0.0353 2.6304 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3696 -0.0185 1.3366 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0506 -0.3895 1.0609 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5517 -0.4485 -0.2228 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8283 -0.8328 -0.5781 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7884 0.3011 -0.5841 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4545 1.5023 -1.2287 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3252 2.5709 -1.2695 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5677 2.5112 -0.6781 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9147 1.3529 -0.0446 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0378 0.2814 -0.0052 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4490 -0.9582 0.7026 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6443 -1.2684 0.7616 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3165 -1.7094 1.2814 C 0 0 2 0 0 0 0 0 0 0 0 0 2.6453 -3.1623 1.6046 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3128 -3.7027 1.5903 O 0 0 0 0 0 0 0 0 0 0 0 0 0.4959 -2.9510 0.7470 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7326 -3.1440 0.6471 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3962 -1.9949 0.1011 C 0 0 1 0 0 0 0 0 0 0 0 0 4.2472 3.7164 -0.8622 O 0 0 0 0 0 0 0 0 0 0 0 0 3.6040 4.3523 -1.9490 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2619 3.8540 -1.8245 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4735 -0.1074 -1.2200 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7610 0.2572 -0.9859 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6034 0.5789 -2.0405 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.1243 0.5275 -3.3506 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2239 0.3043 0.3177 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5377 0.6799 0.5060 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.5651 -0.2949 0.5231 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0472 0.2281 3.6297 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5059 0.0280 4.6868 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9110 -1.3871 3.7749 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4145 -0.6357 1.8939 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7656 -1.1194 -1.6919 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4722 1.5550 -1.6977 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9016 1.2682 0.4378 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8403 -1.2091 2.1162 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1393 -3.2908 2.5623 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1572 -3.5795 0.7330 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0605 -2.5636 -0.6209 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0311 4.0854 -2.9246 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6290 5.4449 -1.7473 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1035 -0.1495 -2.2347 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8574 0.8623 -4.1024 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2203 1.1834 -3.5028 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7851 -0.4916 -3.6531 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1630 -1.3173 0.2948 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3599 -0.0864 -0.2010 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0434 -0.3827 1.5295 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 6 7 1 0 7 8 2 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 13 15 1 0 15 16 1 0 16 17 1 0 17 18 1 0 18 19 2 0 18 20 1 0 10 21 1 0 21 22 1 0 22 23 1 0 5 24 2 0 24 25 1 0 25 26 1 0 26 27 1 0 25 28 2 0 28 29 1 0 29 30 1 0 28 3 1 0 20 6 1 0 12 7 1 0 20 15 1 0 23 9 1 0 1 31 1 0 1 32 1 0 1 33 1 0 4 34 1 0 6 35 1 6 8 36 1 0 11 37 1 0 15 38 1 1 16 39 1 0 16 40 1 0 20 41 1 6 22 42 1 0 22 43 1 0 24 44 1 0 27 45 1 0 27 46 1 0 27 47 1 0 30 48 1 0 30 49 1 0 30 50 1 0 M END

Standard InCHIKey	ISCQYPPCSYRZOT-ZNZDAUKMSA-N
Standard InCHI	InChI=1S/C22H20O8/c1-25-16-4-10(5-17(26-2)21(16)27-3)18-11-6-14-15(30-9-29-14)7-12(11)20(23)13-8-28-22(24)19(13)18/h4-7,13,18-19H,8-9H2,1-3H3/t13-,18+,19-/m1/s1
SMILES	COC1=CC([C@H]2C3=CC4=C(C=C3C(=O)[C@@H]3COC(=O)[C@@H]23)OCO4)=CC(OC)=C1OC

Calculated Properties

Physi-Chem Properties

Molecular Weight:	412.12	Volume:	395.516 ? Van der Waals volume.
Dense:	1.042	LogP:	2.275 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.441 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.88 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	4.0	Rigid Bonds:	27.0
TPSA:	89.52 ? Topological Polar Surface Area.	H-Bond Acceptor:	8.0
H-Bond Donor:	0.0	Rings:	5.0
Heavy Atoms:	8.0

MedChem Properties

QED Drug-Likeness Score:	0.708	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	3.622	Fsp³:	0.364
MCE-18:	93.333 ? 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:	0.142	Fluc inhibitor:	0.144 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.273 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.357 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.245	Promiscuous compounds:	0.459

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.819	MDCK Permeability:	-4.719
Pgp-inhibitor:	0.123	Pgp-substrate:	0.002
PAMPA:	0.038 ? 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%):	0.002	30% Bioavailability (F30%):	0.0
50% Bioavailability (F50%):	0.112

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.973	MRP1:	0.991
Plasma Protein Binding (PPB):	96.307%	Volume Distribution (VD):	0.118
Fu:	4.32% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.934
OATP1B3 inhibitor:	0.964	BCRP inhibitor:	0.002
BSEP inhibitor:	1.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.988	CYP1A2-substrate:	0.635
CYP2C19-inhibitor:	1.0	CYP2C19-substrate:	1.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.985
CYP3A4-inhibitor:	1.0	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.963
HLM stability:	0.671 ? 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):

2.867

Half-life (T1/2):

2.374

ADMET: Toxicity

hERG Blockers:	0.246	hERG Blockers (10um):	0.597
Human Hepatotoxicity (H-HT):	0.942	Drug-induced Liver Injury (DILI):	0.992
AMES Toxicity:	0.683	Rat Oral Acute Toxicity:	0.212
Maximum Recommended Daily Dose:	0.48	Skin Sensitization:	0.982
Carcinogencity:	0.788	Eye Corrosion:	0.001
Eye Irritation:	0.701	Respiratory Toxicity:	0.235
Drug-induced Neurotoxicity:	0.302	Ototoxicity:	0.833
Hematotoxicity:	0.947	Drug-induced Nephrotoxicity:	0.985
Genotoxicity:	0.983	RPMI-8226 Immunitoxicity:	0.24
A549 Cytotoxicity:	0.123	Hek293 Cytotoxicity:	0.537
BCF:	1.531 ? 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:	4.04 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.538 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.234 ? 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
NPO20275	Juniperus sabina	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[34203980]
NPO20275	Juniperus sabina	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[37894884]
NPO22413	Dysosma aurantiocaulis	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27647	Diphylleia cymosa	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO23382	Podophyllum emodii	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO52168	Podophyllum hexandrum	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO30046	Dysosma majorensis	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26868	Diphylleia sinensis	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27244	Dysosma pleiantha	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20275	Juniperus sabina	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22413	Dysosma aurantiocaulis	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23382	Podophyllum emodii	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26868	Diphylleia sinensis	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO30046	Dysosma majorensis	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO20275	Juniperus sabina	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO27244	Dysosma pleiantha	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22413	Dysosma aurantiocaulis	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27647	Diphylleia cymosa	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26868	Diphylleia sinensis	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27244	Dysosma pleiantha	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20275	Juniperus sabina	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23382	Podophyllum emodii	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20275	Juniperus sabina	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO26868	Diphylleia sinensis	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO27647	Diphylleia cymosa	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22413	Dysosma aurantiocaulis	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27244	Dysosma pleiantha	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20275	Juniperus sabina	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26868	Diphylleia sinensis	Species	Berberidaceae	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 NPC515784 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	29052
0.1-0.2	19352
0.2-0.3	1220
0.3-0.4	156
0.4-0.5	40
0.5-0.6	21
0.6-0.7	14
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC239890
1.0	High Similarity	NPC209411
0.6557	Remote Similarity	NPC237946
0.6557	Remote Similarity	NPC32373
0.65	Remote Similarity	NPC80230
0.65	Remote Similarity	NPC104024
0.65	Remote Similarity	NPC101755
0.65	Remote Similarity	NPC304687
0.65	Remote Similarity	NPC65574
0.6129	Remote Similarity	NPC262455
0.6129	Remote Similarity	NPC177476
0.6094	Remote Similarity	NPC210642
0.6094	Remote Similarity	NPC13985
0.6094	Remote Similarity	NPC207584
0.6094	Remote Similarity	NPC19947
0.6032	Remote Similarity	NPC149505
0.5909	Remote Similarity	NPC119910
0.5781	Remote Similarity	NPC480477
0.5588	Remote Similarity	NPC115281
0.5517	Remote Similarity	NPC151423
0.5362	Remote Similarity	NPC288149
0.5362	Remote Similarity	NPC470637
0.5345	Remote Similarity	NPC218841
0.5323	Remote Similarity	NPC477698
0.5294	Remote Similarity	NPC91634
0.5294	Remote Similarity	NPC150943
0.5294	Remote Similarity	NPC268718
0.5246	Remote Similarity	NPC86455
0.5246	Remote Similarity	NPC125134
0.5246	Remote Similarity	NPC137920
0.5167	Remote Similarity	NPC475000
0.5161	Remote Similarity	NPC164082
0.5147	Remote Similarity	NPC30009
0.5147	Remote Similarity	NPC103197
0.5077	Remote Similarity	NPC218092
0.5077	Remote Similarity	NPC246474
0.5077	Remote Similarity	NPC162851

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC515784 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5555
0.1-0.2	3511
0.2-0.3	72
0.3-0.4	4
0.4-0.5	4
0.5-0.6	1
0.6-0.7	3
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
0.6557	Remote Similarity	NPD4965	Approved
0.6557	Remote Similarity	NPD4966	Phase 4
0.6557	Remote Similarity	NPD4967	Phase 2
0.5455	Remote Similarity	NPD37	Approved

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