NPASS Compound

Natural Product: NPC477958

Natural Product ID	NPC477958
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	(2S)-7-hydroxy-2-[3-hydroxy-2,2-dimethyl-8-(3-methylbut-2-enyl)-3,4-dihydrochromen-6-yl]-8-(3-methylbut-2-enyl)-2,3-dihydrochromen-4-one
IUPAC Name	(2S)-7-hydroxy-2-[3-hydroxy-2,2-dimethyl-8-(3-methylbut-2-enyl)-3,4-dihydrochromen-6-yl]-8-(3-methylbut-2-enyl)-2,3-dihydrochromen-4-one
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	101905252
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0000337] Flavans [CHEMONTID:0003642] 8-prenylated flavans [CHEMONTID:0003508] 8-prenylated flavanones

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 71 74 0 0 0 0 0 0 0 0999 V2000 -3.9788 4.3549 0.1341 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1799 3.3106 1.1651 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0818 2.0348 0.8392 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7757 1.6440 -0.5328 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5234 0.8549 -0.6561 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3563 1.4210 -1.1389 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1858 0.7231 -1.2642 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2011 -0.5965 -0.8855 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3199 -1.2295 -0.3970 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4931 -0.4731 -0.2877 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6012 -1.1289 0.2043 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.7832 -2.5217 0.2647 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6738 -3.2010 -0.4707 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3423 -2.6696 0.0162 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7537 -4.5711 -0.4648 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0838 -2.8186 -0.4923 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8920 -3.0270 1.6870 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0417 1.3648 -1.7844 C 0 0 2 0 0 0 0 0 0 0 0 0 1.1676 1.0416 -3.2357 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3026 0.1593 -3.5765 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6125 0.0255 -4.7765 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0516 -0.5445 -2.5466 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9691 -0.0718 -1.2531 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1837 1.0349 -1.0200 O 0 0 0 0 0 0 0 0 0 0 0 0 3.6479 -0.6756 -0.1980 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4133 -1.7789 -0.5122 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4986 -2.2584 -1.8163 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8161 -1.6383 -2.8310 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1249 -2.4438 0.4810 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5486 -0.1505 1.1933 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3849 1.0698 1.2938 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3909 1.1753 2.1345 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7157 0.0396 3.0246 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2104 2.4299 2.2006 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4899 3.7563 2.5604 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1291 5.3537 0.5464 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7362 4.2289 -0.6781 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9880 4.2754 -0.3603 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2312 1.2910 1.6007 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6111 1.0750 -0.9998 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6429 2.5402 -1.2072 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4128 2.4685 -1.4205 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7081 -1.1728 -0.9726 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7549 -2.8660 -1.5464 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5515 -3.2012 -0.5514 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1955 -2.7862 1.1011 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6823 -4.8204 -0.2343 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6362 -3.5987 0.0711 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7323 -1.9258 -0.5500 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8780 -3.1532 -1.5175 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9512 -3.3502 1.8617 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6163 -2.2067 2.3640 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2625 -3.9056 1.8644 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8988 2.4755 -1.6503 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2544 0.5880 -3.6839 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3232 1.9941 -3.8239 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0994 -3.1262 -2.0684 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8667 -1.9934 -3.8557 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9685 -2.9351 0.2193 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9546 -0.9460 1.8591 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4784 0.0406 1.3976 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1461 1.9117 0.6357 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4916 0.3649 3.7730 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1278 -0.8097 2.4488 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8193 -0.3092 3.5945 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5552 3.1999 2.6558 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0854 2.2748 2.8515 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5277 2.7270 1.1921 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4388 4.3141 2.5787 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5358 2.8756 3.2405 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6826 4.4663 2.8617 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 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 12 13 1 0 13 14 1 0 13 15 1 0 12 16 1 0 12 17 1 0 7 18 1 0 18 19 1 0 19 20 1 0 20 21 2 0 20 22 1 0 22 23 2 0 23 24 1 0 23 25 1 0 25 26 2 0 26 27 1 0 27 28 2 0 26 29 1 0 25 30 1 0 30 31 1 0 31 32 2 3 32 33 1 0 32 34 1 0 2 35 1 0 10 5 1 0 14 9 1 0 24 18 1 0 28 22 1 0 1 36 1 0 1 37 1 0 1 38 1 0 3 39 1 0 4 40 1 0 4 41 1 0 6 42 1 0 8 43 1 0 13 44 1 0 14 45 1 0 14 46 1 0 15 47 1 0 16 48 1 0 16 49 1 0 16 50 1 0 17 51 1 0 17 52 1 0 17 53 1 0 18 54 1 6 19 55 1 0 19 56 1 0 27 57 1 0 28 58 1 0 29 59 1 0 30 60 1 0 30 61 1 0 31 62 1 0 33 63 1 0 33 64 1 0 33 65 1 0 34 66 1 0 34 67 1 0 34 68 1 0 35 69 1 0 35 70 1 0 35 71 1 0 M END

Standard InCHIKey	NUOVQYNGOFQMCJ-QBHOUYDASA-N
Standard InCHI	InChI=1S/C30H36O5/c1-17(2)7-9-19-13-20(14-21-15-27(33)30(5,6)35-28(19)21)26-16-25(32)23-11-12-24(31)22(29(23)34-26)10-8-18(3)4/h7-8,11-14,26-27,31,33H,9-10,15-16H2,1-6H3/t26-,27?/m0/s1
SMILES	CC(=CCC1=CC(=CC2=C1OC(C(C2)O)(C)C)[C@@H]3CC(=O)C4=C(O3)C(=C(C=C4)O)CC=C(C)C)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	476.26	Volume:	513.433 ? Van der Waals volume.
Dense:	0.928	LogP:	5.944 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	4.211 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.321 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	5.0	Rigid Bonds:	25.0
TPSA:	75.99 ? Topological Polar Surface Area.	H-Bond Acceptor:	5.0
H-Bond Donor:	2.0	Rings:	4.0
Heavy Atoms:	5.0

MedChem Properties

QED Drug-Likeness Score:	0.503	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.111	Fsp³:	0.433
MCE-18:	90.512 ? 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:	1
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.981	Fluc inhibitor:	0.382 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.652 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.549 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.104	Promiscuous compounds:	0.011

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.842	MDCK Permeability:	-4.67
Pgp-inhibitor:	0.389	Pgp-substrate:	0.131
PAMPA:	0.411 ? 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):	0.124
20% Bioavailability (F20%):	1.0	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.983
Plasma Protein Binding (PPB):	93.933%	Volume Distribution (VD):	0.2
Fu:	7.353% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.814
OATP1B3 inhibitor:	0.985	BCRP inhibitor:	0.999
BSEP inhibitor:	0.839

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	1.0
CYP2C19-inhibitor:	0.999	CYP2C19-substrate:	1.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.001
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.14
CYP3A4-inhibitor:	0.955	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	1.0 ? 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):

7.876

Half-life (T1/2):

1.071

ADMET: Toxicity

hERG Blockers:	0.147	hERG Blockers (10um):	0.609
Human Hepatotoxicity (H-HT):	0.861	Drug-induced Liver Injury (DILI):	0.794
AMES Toxicity:	0.8	Rat Oral Acute Toxicity:	0.96
Maximum Recommended Daily Dose:	0.905	Skin Sensitization:	0.955
Carcinogencity:	0.585	Eye Corrosion:	0.0
Eye Irritation:	0.02	Respiratory Toxicity:	0.99
Drug-induced Neurotoxicity:	0.899	Ototoxicity:	0.956
Hematotoxicity:	0.364	Drug-induced Nephrotoxicity:	0.96
Genotoxicity:	0.987	RPMI-8226 Immunitoxicity:	0.083
A549 Cytotoxicity:	0.92	Hek293 Cytotoxicity:	0.721
BCF:	2.215 ? 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:	5.3 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	7.44 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	6.842 ? 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
NPO7715	Sophora tonkinensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24345512]
NPO7715	Sophora tonkinensis	Species	Fabaceae	Eukaryota	root	n.a.	n.a.	PMID[24959987]
NPO7715	Sophora tonkinensis	Species	Fabaceae	Eukaryota	Rhizomes	Nanning, Guangxi Province, China	2012-Dec	PMID[26132528]
NPO7715	Sophora tonkinensis	Species	Fabaceae	Eukaryota	Roots; Rhizomes	n.a.	n.a.	PMID[30698432]
NPO7715	Sophora tonkinensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7715	Sophora tonkinensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO7715	Sophora tonkinensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO7715	Sophora tonkinensis	Species	Fabaceae	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
EC50	1

Activity Type	# Activity
Individual protein	1

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT546	Individual protein	Retinoid X receptor alpha	Homo sapiens	EC50	=	780	nM	PMID[24959987]

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 NPC477958 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	13537
0.1-0.2	31604
0.2-0.3	4072
0.3-0.4	505
0.4-0.5	100
0.5-0.6	28
0.6-0.7	7
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	Natural Product ID
0.7286	Intermediate Similarity	NPC477957
0.7123	Intermediate Similarity	NPC132592
0.7077	Intermediate Similarity	NPC236766
0.6923	Remote Similarity	NPC164980
0.6818	Remote Similarity	NPC150408
0.6667	Remote Similarity	NPC474021
0.6471	Remote Similarity	NPC149026
0.6324	Remote Similarity	NPC91560
0.6104	Remote Similarity	NPC101793
0.6	Remote Similarity	NPC479211
0.5946	Remote Similarity	NPC36275
0.5921	Remote Similarity	NPC479213
0.5915	Remote Similarity	NPC68104
0.5694	Remote Similarity	NPC197252
0.5641	Remote Similarity	NPC479215
0.5584	Remote Similarity	NPC479214
0.557	Remote Similarity	NPC479212
0.5556	Remote Similarity	NPC75049
0.55	Remote Similarity	NPC110303
0.55	Remote Similarity	NPC601247
0.5479	Remote Similarity	NPC243171
0.5479	Remote Similarity	NPC482705
0.5342	Remote Similarity	NPC221432
0.5342	Remote Similarity	NPC257097
0.5333	Remote Similarity	NPC474033
0.5309	Remote Similarity	NPC209040
0.5278	Remote Similarity	NPC143896
0.527	Remote Similarity	NPC66515
0.5263	Remote Similarity	NPC161506
0.5256	Remote Similarity	NPC39752
0.5244	Remote Similarity	NPC474023
0.5205	Remote Similarity	NPC107572
0.5205	Remote Similarity	NPC32739
0.52	Remote Similarity	NPC76338
0.52	Remote Similarity	NPC250242
0.5185	Remote Similarity	NPC479217
0.5067	Remote Similarity	NPC17170
0.5067	Remote Similarity	NPC310130

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC477958 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	2973
0.1-0.2	6084
0.2-0.3	85
0.3-0.4	8
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