NPASS Compound

Natural Product: NPC226294

Natural Product ID	NPC226294
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	2-(3,4-Dihydroxyphenyl)-5,6-dihydroxy-7-(alpha-L-rhamnopyranosyloxy)-4H-1-benzopyran-4-one
IUPAC Name	2-(3,4-dihydroxyphenyl)-5,6-dihydroxy-7-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxychromen-4-one
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	49798951
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001111] Flavonoid glycosides [CHEMONTID:0001583] Flavonoid O-glycosides [CHEMONTID:0003533] Flavonoid-7-O-glycosides

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 52 55 0 0 0 0 0 0 0 0999 V2000 5.3401 2.2116 1.1318 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7755 1.4091 -0.0281 C 0 0 1 0 0 0 0 0 0 0 0 0 5.3578 0.0229 -0.0926 C 0 0 1 0 0 0 0 0 0 0 0 0 4.8178 -0.9027 0.9557 C 0 0 2 0 0 0 0 0 0 0 0 0 3.5087 -0.3851 1.4649 C 0 0 2 0 0 0 0 0 0 0 0 0 2.7347 0.3974 0.4369 C 0 0 1 0 0 0 0 0 0 0 0 0 3.4222 1.4705 -0.0744 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3029 -0.3939 -0.6360 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0161 -0.6633 -1.0242 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8495 -1.4856 -2.1336 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4128 -1.8127 -2.5988 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5296 -1.3314 -1.9738 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3968 -0.5144 -0.8723 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1162 -0.1902 -0.4106 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4654 -0.0519 -0.2715 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.7051 -0.3309 -0.6716 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8711 -1.1427 -1.7669 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7719 -1.6712 -2.4557 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8650 -2.4087 -3.4497 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.8521 0.2144 0.0390 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6694 1.0414 1.1549 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7497 1.5628 1.8347 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.0530 1.2872 1.4383 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.2343 0.4856 0.3566 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1488 -0.0348 -0.3218 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.1632 1.7917 2.0949 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.5891 2.3852 2.9441 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5623 -2.6322 -3.7042 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9297 -2.0182 -2.8284 O 0 0 0 0 0 0 0 0 0 0 0 0 3.6467 0.3134 2.6391 O 0 0 0 0 0 0 0 0 0 0 0 0 5.7017 -1.0381 2.0344 O 0 0 0 0 0 0 0 0 0 0 0 0 5.2395 -0.5001 -1.3826 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0274 3.0143 0.7968 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9514 1.5679 1.8170 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5254 2.7421 1.6954 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1527 1.9181 -0.9669 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4594 0.1312 0.0966 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7411 -1.9168 0.5016 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8773 -1.2917 1.7016 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8436 0.7974 0.9555 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0595 0.4520 0.4544 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8331 -1.4224 -2.1623 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6554 1.2772 1.4920 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.2218 0.2421 0.0097 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3678 -0.6657 -1.1746 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.9684 2.1556 1.5628 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6717 3.3933 2.8918 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5066 -3.6436 -3.5081 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7262 -2.4276 -2.4019 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4865 0.0459 3.1222 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4454 -1.6086 1.7155 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5607 0.1542 -2.0255 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 3 4 1 0 4 5 1 0 5 6 1 0 6 7 1 0 6 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 13 15 1 0 15 16 1 0 16 17 2 0 17 18 1 0 18 19 2 0 16 20 1 0 20 21 2 0 21 22 1 0 22 23 2 0 23 24 1 0 24 25 2 0 23 26 1 0 22 27 1 0 11 28 1 0 10 29 1 0 5 30 1 0 4 31 1 0 3 32 1 0 7 2 1 0 14 9 1 0 18 12 1 0 25 20 1 0 1 33 1 0 1 34 1 0 1 35 1 0 2 36 1 6 3 37 1 1 4 38 1 6 5 39 1 1 6 40 1 1 14 41 1 0 17 42 1 0 21 43 1 0 24 44 1 0 25 45 1 0 26 46 1 0 27 47 1 0 28 48 1 0 29 49 1 0 30 50 1 0 31 51 1 0 32 52 1 0 M END

Standard InCHIKey	WBSLGYBCKVSSQR-DGZYFPJZSA-N
Standard InCHI	InChI=1S/C21H20O11/c1-7-16(25)19(28)20(29)21(30-7)32-14-6-13-15(18(27)17(14)26)11(24)5-12(31-13)8-2-3-9(22)10(23)4-8/h2-7,16,19-23,25-29H,1H3/t7-,16-,19+,20+,21-/m0/s1
SMILES	C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)OC2=C(C(=C3C(=C2)OC(=CC3=O)C4=CC(=C(C=C4)O)O)O)O)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	448.1	Volume:	413.147 ? Van der Waals volume.
Dense:	1.085	LogP:	1.213 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.438 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.996 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	3.0	Rigid Bonds:	24.0
TPSA:	190.28 ? Topological Polar Surface Area.	H-Bond Acceptor:	11.0
H-Bond Donor:	7.0	Rings:	4.0
Heavy Atoms:	11.0

MedChem Properties

QED Drug-Likeness Score:	0.276	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.048	Fsp³:	0.286
MCE-18:	91.0 ? 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:	Rejected	BMS Rule:	0
Chelating Alert:	1	PAINS Alert:	1
Colloidal aggregators:	0.596	Fluc inhibitor:	0.309 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.972 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.805 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.238	Promiscuous compounds:	0.86

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.155	MDCK Permeability:	-4.948
Pgp-inhibitor:	0.0	Pgp-substrate:	0.176
PAMPA:	0.998 ? 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):	0.662
20% Bioavailability (F20%):	0.989	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.001	MRP1:	0.757
Plasma Protein Binding (PPB):	82.227%	Volume Distribution (VD):	-0.007
Fu:	15.57% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.996
OATP1B3 inhibitor:	0.999	BCRP inhibitor:	0.954
BSEP inhibitor:	0.002

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.047
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.237
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.712
HLM stability:	0.025 ? 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):

3.823

Half-life (T1/2):

4.727

ADMET: Toxicity

hERG Blockers:	0.028	hERG Blockers (10um):	0.357
Human Hepatotoxicity (H-HT):	0.444	Drug-induced Liver Injury (DILI):	0.954
AMES Toxicity:	0.772	Rat Oral Acute Toxicity:	0.181
Maximum Recommended Daily Dose:	0.247	Skin Sensitization:	0.994
Carcinogencity:	0.119	Eye Corrosion:	0.002
Eye Irritation:	0.939	Respiratory Toxicity:	0.15
Drug-induced Neurotoxicity:	0.003	Ototoxicity:	0.788
Hematotoxicity:	0.103	Drug-induced Nephrotoxicity:	0.18
Genotoxicity:	0.938	RPMI-8226 Immunitoxicity:	0.083
A549 Cytotoxicity:	0.88	Hek293 Cytotoxicity:	0.355
BCF:	0.721 ? 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:	3.32 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.768 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.235 ? 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
NPO20259	Vriesea sanguinolenta	Species	Bromeliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19299148]
NPO20259	Vriesea sanguinolenta	Species	Bromeliaceae	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 NPC226294 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	22169
0.1-0.2	24341
0.2-0.3	2387
0.3-0.4	608
0.4-0.5	239
0.5-0.6	90
0.6-0.7	16
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
0.8451	Intermediate Similarity	NPC58716
0.7671	Intermediate Similarity	NPC19709
0.7333	Intermediate Similarity	NPC146792
0.6988	Remote Similarity	NPC3583
0.6974	Remote Similarity	NPC45618
0.6623	Remote Similarity	NPC473043
0.6623	Remote Similarity	NPC331652
0.6582	Remote Similarity	NPC245014
0.6471	Remote Similarity	NPC162313
0.6456	Remote Similarity	NPC189142
0.6456	Remote Similarity	NPC77660
0.6395	Remote Similarity	NPC210073
0.6375	Remote Similarity	NPC45638
0.6296	Remote Similarity	NPC201292
0.619	Remote Similarity	NPC190003
0.6145	Remote Similarity	NPC43211
0.6125	Remote Similarity	NPC238376
0.6047	Remote Similarity	NPC254540
0.6	Remote Similarity	NPC470443
0.5976	Remote Similarity	NPC271692
0.5976	Remote Similarity	NPC27640
0.5854	Remote Similarity	NPC168822
0.5833	Remote Similarity	NPC237435
0.5783	Remote Similarity	NPC84265
0.5778	Remote Similarity	NPC115674
0.5761	Remote Similarity	NPC150767
0.5732	Remote Similarity	NPC127546
0.5732	Remote Similarity	NPC57625
0.5732	Remote Similarity	NPC173637
0.5732	Remote Similarity	NPC317489
0.5732	Remote Similarity	NPC223424
0.5732	Remote Similarity	NPC600591
0.5698	Remote Similarity	NPC605784
0.5667	Remote Similarity	NPC607513
0.5595	Remote Similarity	NPC305811
0.5581	Remote Similarity	NPC115760
0.5581	Remote Similarity	NPC601144
0.5581	Remote Similarity	NPC605067
0.5581	Remote Similarity	NPC606560
0.5568	Remote Similarity	NPC477848
0.5556	Remote Similarity	NPC44931
0.5542	Remote Similarity	NPC39360
0.5542	Remote Similarity	NPC249281
0.5542	Remote Similarity	NPC29763
0.5542	Remote Similarity	NPC210003
0.5529	Remote Similarity	NPC59534
0.5484	Remote Similarity	NPC65711
0.5476	Remote Similarity	NPC93337
0.5426	Remote Similarity	NPC209296
0.5426	Remote Similarity	NPC229409
0.5417	Remote Similarity	NPC198826
0.5412	Remote Similarity	NPC46420
0.5412	Remote Similarity	NPC105025
0.5402	Remote Similarity	NPC22832
0.5402	Remote Similarity	NPC181616
0.5357	Remote Similarity	NPC261866
0.5357	Remote Similarity	NPC108831
0.5357	Remote Similarity	NPC182634
0.5349	Remote Similarity	NPC27942
0.5341	Remote Similarity	NPC311830
0.5341	Remote Similarity	NPC602805
0.5333	Remote Similarity	NPC8856
0.5306	Remote Similarity	NPC603856
0.5294	Remote Similarity	NPC158674
0.5287	Remote Similarity	NPC191306
0.5287	Remote Similarity	NPC20505
0.5281	Remote Similarity	NPC469931
0.527	Remote Similarity	NPC212678
0.5238	Remote Similarity	NPC111929
0.5238	Remote Similarity	NPC320283
0.5238	Remote Similarity	NPC41121
0.5227	Remote Similarity	NPC601710
0.5222	Remote Similarity	NPC294629
0.5222	Remote Similarity	NPC172807
0.5222	Remote Similarity	NPC131407
0.5217	Remote Similarity	NPC67105
0.5176	Remote Similarity	NPC58053
0.5176	Remote Similarity	NPC476405
0.5169	Remote Similarity	NPC116458
0.5169	Remote Similarity	NPC246943
0.5161	Remote Similarity	NPC22062
0.5161	Remote Similarity	NPC473634
0.5161	Remote Similarity	NPC138811
0.5158	Remote Similarity	NPC483414
0.5158	Remote Similarity	NPC483415
0.5135	Remote Similarity	NPC25270
0.5116	Remote Similarity	NPC95090
0.5116	Remote Similarity	NPC277205
0.5116	Remote Similarity	NPC27408
0.5116	Remote Similarity	NPC37919
0.5116	Remote Similarity	NPC136042
0.5114	Remote Similarity	NPC611303
0.5111	Remote Similarity	NPC276377
0.5106	Remote Similarity	NPC204693
0.5104	Remote Similarity	NPC483416
0.5068	Remote Similarity	NPC275722
0.5059	Remote Similarity	NPC135599
0.5059	Remote Similarity	NPC73855
0.5059	Remote Similarity	NPC113968
0.5059	Remote Similarity	NPC328940
0.5059	Remote Similarity	NPC277174
0.5059	Remote Similarity	NPC606877
0.5057	Remote Similarity	NPC186807
0.5057	Remote Similarity	NPC84362
0.5057	Remote Similarity	NPC181712
0.5057	Remote Similarity	NPC610763
0.5055	Remote Similarity	NPC4390
0.5055	Remote Similarity	NPC265115
0.5054	Remote Similarity	NPC78734

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC226294 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5503
0.1-0.2	3588
0.2-0.3	46
0.3-0.4	7
0.4-0.5	4
0.5-0.6	2
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
0.5833	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.5426	Remote Similarity	NPD7054	Phase 4

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