NPASS Compound

Natural Product: NPC536038

Natural Product ID	NPC536038
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	5'-Methoxybilobetin
IUPAC Name	8-[5-(5,7-dihydroxy-4-oxo-chromen-2-yl)-2,3-dimethoxy-phenyl]-5,7-dihydroxy-2-(4-hydroxyphenyl)chromen-4-one
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 65 70 0 0 0 0 0 0 0 0999 V2000 3.0943 -2.6855 2.2962 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8099 -3.0157 1.8074 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3140 -2.2351 0.7554 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0183 -1.1959 0.2075 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5179 -0.4304 -0.8330 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3600 0.6628 -1.3460 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9706 1.4882 -2.3742 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7912 2.5209 -2.8432 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4513 3.2735 -3.7712 O 0 0 0 0 0 0 0 0 0 0 0 0 4.0228 2.7127 -2.2558 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8908 3.7100 -2.6614 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4720 4.5293 -3.7022 O 0 0 0 0 0 0 0 0 0 0 0 0 6.1277 3.8824 -2.0524 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4727 3.0326 -1.0287 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7178 3.2060 -0.4155 O 0 0 0 0 0 0 0 0 0 0 0 0 5.5969 2.0462 -0.6383 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3550 1.8508 -1.2287 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5435 0.9007 -0.8325 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2750 -0.7044 -1.3492 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4665 -1.7413 -0.8268 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7900 -2.1026 -1.3103 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0343 -3.0097 -2.3201 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9206 -3.6083 -2.9020 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3330 -3.3100 -2.7352 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4023 -2.6894 -2.1263 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7198 -2.9381 -2.4861 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1797 -1.7842 -1.1199 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8714 -1.4926 -0.7138 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6672 -0.6269 0.2480 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.6220 0.0153 0.8882 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2798 0.9712 1.9579 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2298 1.6631 2.6527 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8407 2.5586 3.6594 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5230 2.7800 3.9893 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1845 3.6758 4.9930 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5586 2.0706 3.2763 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9610 1.1963 2.2919 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9150 -0.2549 0.5064 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2347 -1.1582 -0.5042 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3984 -1.4060 -0.8528 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0591 -2.4855 0.2093 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6415 -3.5501 0.7835 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4958 -3.3432 1.8698 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1159 -1.6835 2.7754 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8501 -2.6419 1.4752 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4680 -3.4829 2.9891 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0094 -0.9583 0.6010 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0109 1.3503 -2.8429 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7688 5.2237 -3.4711 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7810 4.6751 -2.3978 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0111 2.5922 0.3369 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9122 1.4022 0.1711 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1444 -0.1369 -2.1509 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9655 -4.3324 -3.5938 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4765 -4.0139 -3.5157 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2400 -3.5622 -1.8884 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2782 1.5431 2.4517 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5900 3.1055 4.2088 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1815 4.6756 4.8601 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5380 2.2449 3.5350 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2023 0.6558 1.7503 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7279 0.2372 0.9915 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5182 -2.2724 2.1421 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5080 -3.7168 1.6171 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1481 -3.8837 2.7928 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 2 0 7 8 1 0 8 9 2 0 8 10 1 0 10 11 2 0 11 12 1 0 11 13 1 0 13 14 2 0 14 15 1 0 14 16 1 0 16 17 2 0 17 18 1 0 5 19 2 0 19 20 1 0 20 21 1 0 21 22 2 0 22 23 1 0 22 24 1 0 24 25 2 0 25 26 1 0 25 27 1 0 27 28 2 0 28 29 1 0 29 30 1 0 30 31 1 0 31 32 2 0 32 33 1 0 33 34 2 0 34 35 1 0 34 36 1 0 36 37 2 0 30 38 2 0 38 39 1 0 39 40 2 0 20 41 2 0 41 42 1 0 42 43 1 0 41 3 1 0 18 6 1 0 28 21 1 0 37 31 1 0 17 10 1 0 39 27 1 0 1 44 1 0 1 45 1 0 1 46 1 0 4 47 1 0 7 48 1 0 12 49 1 0 13 50 1 0 15 51 1 0 16 52 1 0 19 53 1 0 23 54 1 0 24 55 1 0 26 56 1 0 32 57 1 0 33 58 1 0 35 59 1 0 36 60 1 0 37 61 1 0 38 62 1 0 43 63 1 0 43 64 1 0 43 65 1 0 M END

Standard InCHIKey	RQNXAFVREOYDNA-UHFFFAOYSA-N
Standard InCHI	InChI=1S/C32H22O11/c1-40-27-8-15(25-12-22(38)29-19(35)9-17(34)10-26(29)42-25)7-18(31(27)41-2)28-20(36)11-21(37)30-23(39)13-24(43-32(28)30)14-3-5-16(33)6-4-14/h3-13,33-37H,1-2H3
SMILES	COC1=CC(C2=CC(=O)C3=C(O)C=C(O)C=C3O2)=CC(C2=C(O)C=C(O)C3=C2OC(C2=CC=C(O)C=C2)=CC3=O)=C1OC

Calculated Properties

Physi-Chem Properties

Molecular Weight:	582.12	Volume:	565.198 ? Van der Waals volume.
Dense:	1.03	LogP:	4.263 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.429 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.025 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	5.0	Rigid Bonds:	36.0
TPSA:	180.03 ? Topological Polar Surface Area.	H-Bond Acceptor:	11.0
H-Bond Donor:	5.0	Rings:	6.0
Heavy Atoms:	11.0

MedChem Properties

QED Drug-Likeness Score:	0.174	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	3.126	Fsp³:	0.062
MCE-18:	37.0 ? 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:	1
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.985	Fluc inhibitor:	0.312 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.956 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.997 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.352	Promiscuous compounds:	0.892

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.056	MDCK Permeability:	-4.806
Pgp-inhibitor:	0.009	Pgp-substrate:	0.661
PAMPA:	0.339 ? 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%):	0.235	30% Bioavailability (F30%):	0.872
50% Bioavailability (F50%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.952
Plasma Protein Binding (PPB):	96.633%	Volume Distribution (VD):	-0.368
Fu:	2.841% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.865
OATP1B3 inhibitor:	0.989	BCRP inhibitor:	0.99
BSEP inhibitor:	0.99

ADMET: Metabolism

CYP1A2-inhibitor:	0.826	CYP1A2-substrate:	0.024
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.005
CYP2C9-inhibitor:	0.498	CYP2C9-substrate:	0.818
CYP2D6-inhibitor:	1.0	CYP2D6-substrate:	1.0
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.003
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.9 ? 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):

1.526

Half-life (T1/2):

1.991

ADMET: Toxicity

hERG Blockers:	0.057	hERG Blockers (10um):	0.507
Human Hepatotoxicity (H-HT):	0.458	Drug-induced Liver Injury (DILI):	0.978
AMES Toxicity:	0.678	Rat Oral Acute Toxicity:	0.632
Maximum Recommended Daily Dose:	0.984	Skin Sensitization:	0.508
Carcinogencity:	0.86	Eye Corrosion:	0.002
Eye Irritation:	0.992	Respiratory Toxicity:	0.878
Drug-induced Neurotoxicity:	0.006	Ototoxicity:	0.052
Hematotoxicity:	0.03	Drug-induced Nephrotoxicity:	0.011
Genotoxicity:	1.0	RPMI-8226 Immunitoxicity:	0.133
A549 Cytotoxicity:	0.717	Hek293 Cytotoxicity:	0.978
BCF:	1.193 ? 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:	4.345 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.841 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.492 ? 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
NPO26293	Ginkgo biloba	Species	Ginkgoaceae	Eukaryota	n.a.	leaf	n.a.	DOI[10.1016/S0031-9422(01)00320-X]
NPO26293	Ginkgo biloba	Species	Ginkgoaceae	Eukaryota	n.a.	leaf	n.a.	PMID[11738417]
NPO26293	Ginkgo biloba	Species	Ginkgoaceae	Eukaryota	n.a.	fruit	n.a.	PMID[21462031]
NPO26293	Ginkgo biloba	Species	Ginkgoaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26293	Ginkgo biloba	Species	Ginkgoaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26293	Ginkgo biloba	Species	Ginkgoaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26293	Ginkgo biloba	Species	Ginkgoaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO26293	Ginkgo biloba	Species	Ginkgoaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO26293	Ginkgo biloba	Species	Ginkgoaceae	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 NPC536038 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	32365
0.1-0.2	14888
0.2-0.3	1657
0.3-0.4	728
0.4-0.5	155
0.5-0.6	33
0.6-0.7	22
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
0.8235	Intermediate Similarity	NPC71061
0.7324	Intermediate Similarity	NPC150908
0.7059	Intermediate Similarity	NPC138299
0.7027	Intermediate Similarity	NPC215203
0.6986	Remote Similarity	NPC290830
0.6986	Remote Similarity	NPC303485
0.6842	Remote Similarity	NPC265624
0.6533	Remote Similarity	NPC72425
0.6528	Remote Similarity	NPC254351
0.6452	Remote Similarity	NPC50898
0.6447	Remote Similarity	NPC194593
0.6364	Remote Similarity	NPC62536
0.6351	Remote Similarity	NPC259757
0.6349	Remote Similarity	NPC222713
0.6324	Remote Similarity	NPC12200
0.6282	Remote Similarity	NPC601565
0.625	Remote Similarity	NPC288840
0.6234	Remote Similarity	NPC186227
0.6232	Remote Similarity	NPC183950
0.6184	Remote Similarity	NPC600972
0.6143	Remote Similarity	NPC67322
0.6119	Remote Similarity	NPC231772
0.6087	Remote Similarity	NPC606638
0.6049	Remote Similarity	NPC55443
0.6026	Remote Similarity	NPC14606
0.6	Remote Similarity	NPC610480
0.5882	Remote Similarity	NPC120464
0.5882	Remote Similarity	NPC483773
0.5823	Remote Similarity	NPC63454
0.5823	Remote Similarity	NPC183851
0.5823	Remote Similarity	NPC272064
0.575	Remote Similarity	NPC121649
0.5676	Remote Similarity	NPC111112
0.5658	Remote Similarity	NPC183
0.5652	Remote Similarity	NPC601901
0.5634	Remote Similarity	NPC52005
0.5625	Remote Similarity	NPC159707
0.5616	Remote Similarity	NPC605634
0.5571	Remote Similarity	NPC600900
0.557	Remote Similarity	NPC603508
0.5522	Remote Similarity	NPC279121
0.5507	Remote Similarity	NPC241498
0.5455	Remote Similarity	NPC78540
0.5455	Remote Similarity	NPC196179
0.5429	Remote Similarity	NPC234133
0.5395	Remote Similarity	NPC291746
0.5342	Remote Similarity	NPC610914
0.5301	Remote Similarity	NPC18699
0.5301	Remote Similarity	NPC205026
0.5294	Remote Similarity	NPC274121
0.5286	Remote Similarity	NPC301323
0.5286	Remote Similarity	NPC103342
0.5256	Remote Similarity	NPC34089
0.5211	Remote Similarity	NPC120163
0.5195	Remote Similarity	NPC112954
0.5172	Remote Similarity	NPC172202
0.5172	Remote Similarity	NPC284127
0.5125	Remote Similarity	NPC606549
0.507	Remote Similarity	NPC47815

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC536038 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6479
0.1-0.2	2619
0.2-0.3	43
0.3-0.4	6
0.4-0.5	2
0.5-0.6	1
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
0.5522	Remote Similarity	NPD1511	Phase 2

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