NPASS Compound

Natural Product: NPC159707

Natural Product ID	NPC159707
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	7-O-Methyl-Isoginkgetin
IUPAC Name	5-hydroxy-8-[5-(5-hydroxy-7-methoxy-4-oxochromen-2-yl)-2-methoxyphenyl]-2-(4-hydroxyphenyl)-7-methoxychromen-4-one
Synonyms	7-O-methyl-isoginkgetin
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL208578
PubChem CID	12018906
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001586] Biflavonoids and polyflavonoids

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 67 72 0 0 0 0 0 0 0 0999 V2000 4.3914 0.0411 -3.2027 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4630 -0.6656 -2.3672 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2134 -0.0915 -2.2245 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8026 1.0772 -2.8084 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5307 1.6189 -2.6357 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3604 0.9579 -1.8450 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0206 -0.2290 -1.2370 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2942 -0.7382 -1.4314 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6382 -1.9888 -0.7709 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4156 -3.2124 -1.3910 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8552 -3.1751 -2.6568 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5967 -4.3765 -3.3551 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7520 -4.3767 -0.7398 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3061 -4.3083 0.5214 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5273 -3.0812 1.1387 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1946 -1.9012 0.4973 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3910 -0.7301 1.0531 O 0 0 0 0 0 0 0 0 0 0 0 0 2.9141 -0.5650 2.2532 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2587 -1.7084 2.9248 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0789 -2.9869 2.3966 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3944 -4.0306 3.0119 O 0 0 0 0 0 0 0 0 0 0 0 0 3.1093 0.7684 2.8214 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7412 1.8828 2.0949 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9015 3.1651 2.5795 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4435 3.3883 3.8267 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8153 2.2839 4.5627 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6496 0.9863 4.0643 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6123 4.6827 4.3318 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6475 -5.4802 1.1837 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7393 1.4163 -1.5770 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1909 2.5837 -2.1456 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4799 3.0131 -1.8958 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9367 4.0758 -2.3949 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2669 2.2392 -1.0750 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7517 1.0789 -0.5369 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5262 0.7106 -0.8001 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.5698 0.3061 0.2959 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8528 0.6882 0.5736 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3386 1.8470 0.0245 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5680 2.6266 -0.7933 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0162 3.8009 -1.3678 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.6775 -0.0702 1.3997 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.9900 0.3648 1.6554 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5604 1.0577 -2.8196 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8513 0.1622 -4.1818 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2987 -0.5353 -3.3932 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5039 1.6044 -3.4351 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2541 2.5367 -3.1131 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6620 -0.7729 -0.6071 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5657 -4.1396 -4.4487 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4018 -5.1285 -3.2380 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3698 -4.8408 -3.0369 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5814 -5.3253 -1.2159 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6936 -1.6700 3.9131 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3087 1.7409 1.1029 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6105 4.0361 2.0042 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2430 2.4500 5.5458 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9566 0.1736 4.6817 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1392 5.3939 3.8351 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1830 -5.8199 2.0144 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5742 3.2018 -2.7965 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1721 -0.6048 0.7211 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3461 2.1731 0.2257 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6170 4.4557 -0.8774 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.5418 0.5393 0.6864 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.9974 1.3234 2.2325 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.5650 -0.3570 2.2410 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 2 0 6 7 1 0 7 8 2 0 8 9 1 0 9 10 2 0 10 11 1 0 11 12 1 0 10 13 1 0 13 14 2 0 14 15 1 0 15 16 2 0 16 17 1 0 17 18 1 0 18 19 2 0 19 20 1 0 20 21 2 0 18 22 1 0 22 23 2 0 23 24 1 0 24 25 2 0 25 26 1 0 26 27 2 0 25 28 1 0 14 29 1 0 6 30 1 0 30 31 2 0 31 32 1 0 32 33 2 0 32 34 1 0 34 35 2 0 35 36 1 0 35 37 1 0 37 38 2 0 38 39 1 0 39 40 2 0 40 41 1 0 38 42 1 0 42 43 1 0 8 3 1 0 16 9 1 0 27 22 1 0 36 30 1 0 20 15 1 0 40 34 1 0 1 44 1 0 1 45 1 0 1 46 1 0 4 47 1 0 5 48 1 0 7 49 1 0 12 50 1 0 12 51 1 0 12 52 1 0 13 53 1 0 19 54 1 0 23 55 1 0 24 56 1 0 26 57 1 0 27 58 1 0 28 59 1 0 29 60 1 0 31 61 1 0 37 62 1 0 39 63 1 0 41 64 1 0 43 65 1 0 43 66 1 0 43 67 1 0 M END

Standard InCHIKey	UXZIDQIKMJUHLZ-UHFFFAOYSA-N
Standard InCHI	InChI=1S/C33H24O10/c1-39-19-11-21(35)31-22(36)13-27(42-29(31)12-19)17-6-9-25(40-2)20(10-17)30-28(41-3)15-24(38)32-23(37)14-26(43-33(30)32)16-4-7-18(34)8-5-16/h4-15,34-35,38H,1-3H3
SMILES	COc1ccc(cc1c1c(OC)cc(c2c1oc(cc2=O)c1ccc(cc1)O)O)c1cc(=O)c2c(o1)cc(cc2O)OC

Calculated Properties

Physi-Chem Properties

Molecular Weight:	580.14	Volume:	573.704 ? Van der Waals volume.
Dense:	1.011	LogP:	4.18 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.909 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.891 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	6.0	Rigid Bonds:	36.0
TPSA:	148.8 ? Topological Polar Surface Area.	H-Bond Acceptor:	10.0
H-Bond Donor:	3.0	Rings:	6.0
Heavy Atoms:	10.0

MedChem Properties

QED Drug-Likeness Score:	0.213	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	2.977	Fsp³:	0.091
MCE-18:	36.0 ? 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:	0	PAINS Alert:	0
Colloidal aggregators:	0.994	Fluc inhibitor:	0.287 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.955 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.998 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.311	Promiscuous compounds:	0.851

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.038	MDCK Permeability:	-4.765
Pgp-inhibitor:	0.528	Pgp-substrate:	0.096
PAMPA:	0.023 ? 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):	0.003
20% Bioavailability (F20%):	0.099	30% Bioavailability (F30%):	0.429
50% Bioavailability (F50%):	0.988

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.852
Plasma Protein Binding (PPB):	97.134%	Volume Distribution (VD):	-0.114
Fu:	2.258% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.999
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.984
BSEP inhibitor:	0.998

ADMET: Metabolism

CYP1A2-inhibitor:	0.17	CYP1A2-substrate:	0.458
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.003
CYP2C9-inhibitor:	0.931	CYP2C9-substrate:	0.413
CYP2D6-inhibitor:	0.999	CYP2D6-substrate:	1.0
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.041
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.999
HLM stability:	0.755 ? 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):

3.248

Half-life (T1/2):

1.391

ADMET: Toxicity

hERG Blockers:	0.127	hERG Blockers (10um):	0.495
Human Hepatotoxicity (H-HT):	0.5	Drug-induced Liver Injury (DILI):	0.994
AMES Toxicity:	0.74	Rat Oral Acute Toxicity:	0.598
Maximum Recommended Daily Dose:	0.967	Skin Sensitization:	0.204
Carcinogencity:	0.901	Eye Corrosion:	0.001
Eye Irritation:	0.972	Respiratory Toxicity:	0.869
Drug-induced Neurotoxicity:	0.018	Ototoxicity:	0.076
Hematotoxicity:	0.097	Drug-induced Nephrotoxicity:	0.037
Genotoxicity:	0.997	RPMI-8226 Immunitoxicity:	0.131
A549 Cytotoxicity:	0.527	Hek293 Cytotoxicity:	0.927
BCF:	1.347 ? 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:	4.63 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.275 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.925 ? 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
NPO2284	Cephalotaxus koreana	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16574412]
NPO2284	Cephalotaxus koreana	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17994703]
NPO2284	Cephalotaxus koreana	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2284	Cephalotaxus koreana	Species	Taxaceae	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	1
Activity	4

Activity Type	# Activity
Cell line	3
Individual protein	1
Non-molecular	1

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT740	Individual protein	Beta-secretase 1	Homo sapiens	IC50	>	10000.0	nM	PubChem BioAssay data set

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1309	Cell line	Osteoblasts	n.a.	Activity	=	129.7	%	Open TG-GATES in vivo data: Biochemistry
NPT1309	Cell line	Osteoblasts	n.a.	Activity	=	108.4	%	PMID[16539403]
NPT1309	Cell line	Osteoblasts	n.a.	Activity	=	122.0	%	PMID[23002924]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	Activity	=	65.3	%	PMID[26004578]

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 NPC159707 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	30749
0.1-0.2	16346
0.2-0.3	1998
0.3-0.4	530
0.4-0.5	180
0.5-0.6	27
0.6-0.7	14
0.7-0.8	0
0.8-0.85	1
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8923	High Similarity	NPC248739
0.8143	Intermediate Similarity	NPC215203
0.7971	Intermediate Similarity	NPC603508
0.7917	Intermediate Similarity	NPC265624
0.7606	Intermediate Similarity	NPC158027
0.75	Intermediate Similarity	NPC186227
0.7302	Intermediate Similarity	NPC234133
0.7297	Intermediate Similarity	NPC205026
0.7121	Intermediate Similarity	NPC610914
0.7027	Intermediate Similarity	NPC14606
0.6986	Remote Similarity	NPC601984
0.68	Remote Similarity	NPC194593
0.6615	Remote Similarity	NPC29353
0.6494	Remote Similarity	NPC121649
0.6447	Remote Similarity	NPC290830
0.6447	Remote Similarity	NPC71061
0.641	Remote Similarity	NPC601565
0.6364	Remote Similarity	NPC52611
0.6234	Remote Similarity	NPC600396
0.6176	Remote Similarity	NPC108406
0.6173	Remote Similarity	NPC55443
0.6119	Remote Similarity	NPC127447
0.6	Remote Similarity	NPC195202
0.6	Remote Similarity	NPC223579
0.5915	Remote Similarity	NPC137062
0.5897	Remote Similarity	NPC150908
0.5823	Remote Similarity	NPC72425
0.5775	Remote Similarity	NPC124784
0.5667	Remote Similarity	NPC485523
0.5667	Remote Similarity	NPC485524
0.561	Remote Similarity	NPC18699
0.5571	Remote Similarity	NPC33265
0.5571	Remote Similarity	NPC48479
0.5571	Remote Similarity	NPC143799
0.5513	Remote Similarity	NPC280975
0.5432	Remote Similarity	NPC303485
0.5352	Remote Similarity	NPC198826
0.5352	Remote Similarity	NPC250266
0.5352	Remote Similarity	NPC146679
0.5352	Remote Similarity	NPC120163
0.5342	Remote Similarity	NPC177298
0.5301	Remote Similarity	NPC39360
0.5301	Remote Similarity	NPC29763
0.5301	Remote Similarity	NPC210003
0.5294	Remote Similarity	NPC27942
0.5278	Remote Similarity	NPC78913
0.5181	Remote Similarity	NPC331652
0.5139	Remote Similarity	NPC231772
0.5122	Remote Similarity	NPC600972
0.5059	Remote Similarity	NPC95090
0.5059	Remote Similarity	NPC27408

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC159707 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6009
0.1-0.2	3079
0.2-0.3	53
0.3-0.4	6
0.4-0.5	3
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