NPASS Compound

Natural Product: NPC181616

Natural Product ID	NPC181616
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	5-Hydroxy-2-Methylchromone-7-O-Rutinoside
IUPAC Name	5,6-dihydroxy-2-methyl-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxymethyl]oxan-2-yl]oxychromen-4-one
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL562227
PubChem CID	44139363
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0000011] Carbohydrates and carbohydrate conjugates [CHEMONTID:0002105] Glycosyl compounds [CHEMONTID:0004165] Phenolic 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 64 67 0 0 0 0 0 0 0 0999 V2000 5.5908 4.1464 0.6265 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5927 2.6521 0.7514 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7745 2.0709 1.1746 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7831 0.6954 1.2918 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8122 0.0845 1.6689 O 0 0 0 0 0 0 0 0 0 0 0 0 5.6291 -0.0229 0.9855 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4986 0.6325 0.5724 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3300 -0.0805 0.2610 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3045 -1.4466 0.3666 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4706 -2.0736 0.7886 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6100 -1.3774 1.0922 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7566 -2.0535 1.5122 O 0 0 0 0 0 0 0 0 0 0 0 0 4.4300 -3.4524 0.8905 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1816 -2.1599 0.0696 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9328 -1.7168 -0.3640 C 0 0 1 0 0 0 0 0 0 0 0 0 0.7402 -2.2183 -1.7733 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.6336 -1.7690 -2.2715 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.5957 -2.4112 -1.2925 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.3562 -1.6655 0.0163 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.4480 -1.9837 0.9810 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6569 -1.5150 0.5628 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.7843 -0.1304 0.5070 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.2467 0.2948 -0.8419 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.1984 1.4995 -0.7630 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.6968 2.3145 0.4264 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.0094 1.4878 1.6539 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.3571 2.1409 2.8277 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7496 0.1593 1.4992 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.3783 3.5188 0.5339 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1524 2.2551 -1.9205 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2274 0.7131 -1.6986 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0938 -2.0047 0.5005 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8860 -2.3642 -1.7087 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8562 -2.1510 -3.5722 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7495 -1.8056 -2.6047 O 0 0 0 0 0 0 0 0 0 0 0 0 4.5458 1.9360 0.4789 O 0 0 0 0 0 0 0 0 0 0 0 0 4.5702 4.5551 0.7531 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2369 4.5639 1.4302 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0613 4.4265 -0.3386 H 0 0 0 0 0 0 0 0 0 0 0 0 7.6450 2.6682 1.4010 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5066 0.5384 -0.0515 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9049 -2.9712 1.1007 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2821 -3.9711 0.0374 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9539 -0.6133 -0.4486 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7106 -3.3285 -1.7824 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7242 -0.6628 -2.1190 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2714 -3.4774 -1.1953 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3499 -0.6068 -0.2128 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5261 -3.1180 0.9864 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1923 -1.6831 2.0264 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8191 0.3306 0.7821 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8642 -0.4947 -1.3539 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2136 1.1582 -0.4983 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5913 2.4659 0.3293 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1269 1.5828 1.7986 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0184 2.9732 3.1708 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2462 1.4551 3.7033 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3896 2.6311 2.5700 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0026 3.6174 -0.2086 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8243 1.8992 -2.5579 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3866 0.3179 -2.6031 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0101 -2.3746 -2.6836 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1454 -2.7819 -3.8734 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4252 -1.2997 -3.3910 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 2 0 3 4 1 0 4 5 2 0 4 6 1 0 6 7 2 0 7 8 1 0 8 9 2 0 9 10 1 0 10 11 2 0 11 12 1 0 10 13 1 0 9 14 1 0 14 15 1 0 15 16 1 0 16 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 20 21 1 0 21 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 26 27 1 0 26 28 1 0 25 29 1 0 24 30 1 0 23 31 1 0 19 32 1 0 18 33 1 0 17 34 1 0 16 35 1 0 7 36 1 0 36 2 1 0 11 6 1 0 32 15 1 0 28 22 1 0 1 37 1 0 1 38 1 0 1 39 1 0 3 40 1 0 8 41 1 0 12 42 1 0 13 43 1 0 15 44 1 6 16 45 1 1 17 46 1 6 18 47 1 1 19 48 1 6 20 49 1 0 20 50 1 0 22 51 1 1 23 52 1 6 24 53 1 1 25 54 1 6 26 55 1 1 27 56 1 0 27 57 1 0 27 58 1 0 29 59 1 0 30 60 1 0 31 61 1 0 33 62 1 0 34 63 1 0 35 64 1 0 M END

Standard InCHIKey	JYIVYVFUUKYCSU-GCCWPOOFSA-N
Standard InCHI	InChI=1S/C22H28O14/c1-6-3-8(23)12-9(33-6)4-10(14(25)16(12)27)35-22-20(31)18(29)15(26)11(36-22)5-32-21-19(30)17(28)13(24)7(2)34-21/h3-4,7,11,13,15,17-22,24-31H,5H2,1-2H3/t7-,11+,13-,15+,17+,18-,19+,20+,21+,22+/m0/s1
SMILES	Cc1cc(=O)c2c(cc(c(c2O)O)O[C@H]2[C@@H]([C@H]([C@@H]([C@@H](CO[C@H]3[C@@H]([C@@H]([C@H]([C@H](C)O3)O)O)O)O2)O)O)O)o1

Calculated Properties

Physi-Chem Properties

Molecular Weight:	516.15	Volume:	464.723 ? Van der Waals volume.
Dense:	1.111	LogP:	-1.2 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	0.122 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-0.79 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	5.0	Rigid Bonds:	24.0
TPSA:	228.97 ? Topological Polar Surface Area.	H-Bond Acceptor:	14.0
H-Bond Donor:	8.0	Rings:	4.0
Heavy Atoms:	14.0

MedChem Properties

QED Drug-Likeness Score:	0.193	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.704	Fsp³:	0.591
MCE-18:	103.571 ? 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:	0
Chelating Alert:	1	PAINS Alert:	1
Colloidal aggregators:	0.533	Fluc inhibitor:	0.11 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.179 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.226 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.059	Promiscuous compounds:	0.31

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.368	MDCK Permeability:	-5.174
Pgp-inhibitor:	0.0	Pgp-substrate:	0.725
PAMPA:	1.0 ? 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):	0.075
20% Bioavailability (F20%):	0.223	30% Bioavailability (F30%):	0.946
50% Bioavailability (F50%):	0.974

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.892
Plasma Protein Binding (PPB):	74.479%	Volume Distribution (VD):	-0.275
Fu:	26.13% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.999	BCRP inhibitor:	0.027
BSEP inhibitor:	0.012

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:	0.0
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.003
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.005
HLM stability:	0.0 ? 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):

1.47

Half-life (T1/2):

4.507

ADMET: Toxicity

hERG Blockers:	0.022	hERG Blockers (10um):	0.161
Human Hepatotoxicity (H-HT):	0.35	Drug-induced Liver Injury (DILI):	0.747
AMES Toxicity:	0.866	Rat Oral Acute Toxicity:	0.015
Maximum Recommended Daily Dose:	0.015	Skin Sensitization:	0.941
Carcinogencity:	0.033	Eye Corrosion:	0.0
Eye Irritation:	0.179	Respiratory Toxicity:	0.004
Drug-induced Neurotoxicity:	0.001	Ototoxicity:	0.954
Hematotoxicity:	0.146	Drug-induced Nephrotoxicity:	0.431
Genotoxicity:	0.227	RPMI-8226 Immunitoxicity:	0.143
A549 Cytotoxicity:	0.142	Hek293 Cytotoxicity:	0.149
BCF:	0.209 ? 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:	2.731 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.3 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.395 ? 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
NPO27978	Crossosoma bigelovii	Species	Crossosomataceae	Eukaryota	n.a.	twig	n.a.	DOI[10.1021/np8006342]
NPO27978	Crossosoma bigelovii	Species	Crossosomataceae	Eukaryota	n.a.	fruit	n.a.	DOI[10.1021/np8006342]
NPO27978	Crossosoma bigelovii	Species	Crossosomataceae	Eukaryota	n.a.	leaf	n.a.	DOI[10.1021/np8006342]
NPO27978	Crossosoma bigelovii	Species	Crossosomataceae	Eukaryota	n.a.	flower	n.a.	DOI[10.1021/np8006342]
NPO27978	Crossosoma bigelovii	Species	Crossosomataceae	Eukaryota	n.a.	fruit	n.a.	PMID[19405508]
NPO27978	Crossosoma bigelovii	Species	Crossosomataceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19405508]
NPO27978	Crossosoma bigelovii	Species	Crossosomataceae	Eukaryota	n.a.	leaf	n.a.	PMID[19405508]
NPO27978	Crossosoma bigelovii	Species	Crossosomataceae	Eukaryota	n.a.	flower	n.a.	PMID[19405508]
NPO27978	Crossosoma bigelovii	Species	Crossosomataceae	Eukaryota	n.a.	twig	n.a.	PMID[19405508]
NPO27978	Crossosoma bigelovii	Species	Crossosomataceae	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
GI50	3

Activity Type	# Activity
Cell line	3

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
NPT139	Cell line	HT-29	Homo sapiens	GI50	=	6000.0	nM	PMID[7731021]
NPT81	Cell line	A549	Homo sapiens	GI50	=	400.0	nM	PMID[26091285]
NPT83	Cell line	MCF7	Homo sapiens	GI50	=	800.0	nM	PMID[17552563]

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 NPC181616 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	19803
0.1-0.2	26347
0.2-0.3	2924
0.3-0.4	608
0.4-0.5	136
0.5-0.6	34
0.6-0.7	1
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
0.7595	Intermediate Similarity	NPC99957
0.6087	Remote Similarity	NPC470443
0.5699	Remote Similarity	NPC213052
0.5484	Remote Similarity	NPC44931
0.5426	Remote Similarity	NPC210073
0.5426	Remote Similarity	NPC303913
0.5326	Remote Similarity	NPC477848
0.5319	Remote Similarity	NPC67105
0.5306	Remote Similarity	NPC294722
0.5263	Remote Similarity	NPC22062
0.5263	Remote Similarity	NPC65563
0.5263	Remote Similarity	NPC473634
0.5263	Remote Similarity	NPC470949
0.5263	Remote Similarity	NPC138811
0.5208	Remote Similarity	NPC204693
0.5208	Remote Similarity	NPC186816
0.5204	Remote Similarity	NPC209296
0.5181	Remote Similarity	NPC191154
0.5172	Remote Similarity	NPC114740
0.5158	Remote Similarity	NPC173582
0.5158	Remote Similarity	NPC265885
0.5158	Remote Similarity	NPC181465
0.5158	Remote Similarity	NPC215710
0.5158	Remote Similarity	NPC473438
0.5158	Remote Similarity	NPC227508
0.5158	Remote Similarity	NPC253788
0.5104	Remote Similarity	NPC203259
0.5104	Remote Similarity	NPC33054
0.5104	Remote Similarity	NPC176740
0.5104	Remote Similarity	NPC471725
0.5104	Remote Similarity	NPC134532
0.5104	Remote Similarity	NPC602582
0.506	Remote Similarity	NPC469621
0.5053	Remote Similarity	NPC187379
0.5052	Remote Similarity	NPC473571
0.5052	Remote Similarity	NPC110941

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC181616 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4546
0.1-0.2	4542
0.2-0.3	50
0.3-0.4	6
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
0.5204	Remote Similarity	NPD7054	Phase 4
0.5104	Remote Similarity	NPD6797	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