NPASS Compound

Natural Product: NPC469775

Natural Product ID	NPC469775
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Clematochinenoside E
IUPAC Name	[(2S,3R,4S,5S,6R)-6-[[(2R,3R,4R,5S,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxymethyl]-3,4,5-trihydroxyoxan-2-yl] (4aS,6aR,6aS,6bR,8aR,9R,10S,12aR,14bS)-10-[(2S,3R,4S,5R)-3-[(2S,3R,4R,5S,6S)-4-[(2S,3R,4S,5R)-5-[(2R,3R,4R,5S,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(E)-3-(3-hydroxy-4-methoxyphenyl)prop-2-enoyl]oxymethyl]oxan-2-yl]oxyoxan-2-yl]oxy-3,4-dihydroxyoxan-2-yl]oxy-3,5-dihydroxy-6-methyloxan-2-yl]oxy-4,5-dihydroxyoxan-2-yl]oxy-9-(hydroxymethyl)-2,2,6a,6b,9,12a-hexamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylate
Synonyms	Clematochinenoside E
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL1171254
PubChem CID	49799227
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0002049] Terpene glycosides [CHEMONTID:0001580] Triterpene glycosides [CHEMONTID:0002358] Triterpene saponins

The Chemical Classification was calculated by Classyfire, a software for chemical taxonomy calculation. Reference: DOI:10.1186/s13321-016-0174-y.

Chemical Representations

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22 1 0 22 23 1 0 23 24 1 0 23 25 1 0 25 26 1 0 26 27 2 0 26 28 1 0 28 29 1 0 29 30 1 0 30 31 1 0 31 32 1 0 32 33 1 0 33 34 1 0 34 35 2 0 35 36 1 0 36 37 1 0 37 38 1 0 38 39 1 0 39 40 1 0 40 41 1 0 41 42 1 0 42 43 1 0 43 44 1 0 44 45 1 0 45 46 1 0 46 47 1 0 47 48 1 0 48 49 1 0 47 50 1 0 46 51 1 0 42 52 1 0 42 53 1 0 53 54 1 0 41 55 1 0 55 56 1 0 56 57 1 0 57 58 1 0 58 59 1 0 59 60 1 0 60 61 1 0 59 62 1 0 58 63 1 0 57 64 1 0 64 65 1 0 65 66 1 0 66 67 1 0 67 68 1 0 68 69 1 0 69 70 1 0 69 71 1 0 68 72 1 0 67 73 1 0 73 74 1 0 74 75 1 0 75 76 1 0 76 77 1 0 77 78 1 0 78 79 1 0 77 80 1 0 80 81 1 0 81 82 1 0 82 83 1 0 83 84 1 0 84 85 1 0 85 86 1 0 85 87 1 0 87 88 1 0 84 89 1 0 89 90 1 0 90 91 1 0 91 92 1 0 92 93 1 0 93 94 1 0 94 95 1 0 94 96 1 0 96 97 1 0 97 98 1 0 98 99 2 0 98100 1 0 100101 2 3 101102 1 0 102103 2 0 103104 1 0 104105 2 0 105106 1 0 106107 2 0 105108 1 0 108109 1 0 104110 1 0 93111 1 0 92112 1 0 91113 1 0 83114 1 0 82115 1 0 76116 1 0 75117 1 0 66118 1 0 38119 1 0 31120 1 0 31121 1 0 22122 1 0 21123 1 0 20124 1 0 10125 1 0 125126 1 0 5127 1 0 4128 1 0 3129 1 0 7 2 1 0 70 65 1 0 79 74 1 0 86 81 1 0 95 90 1 0 107102 1 0 14 9 1 0 24 19 1 0 33 28 1 0 49 28 1 0 47 34 1 0 46 37 1 0 43 38 1 0 61 56 1 0 1130 1 0 1131 1 0 1132 1 0 2133 1 0 3134 1 0 4135 1 0 5136 1 0 6137 1 0 9138 1 0 10139 1 0 12140 1 0 13141 1 0 14142 1 0 15143 1 0 16144 1 0 18145 1 0 18146 1 0 19147 1 0 20148 1 0 21149 1 0 22150 1 0 23151 1 0 29152 1 0 29153 1 0 30154 1 0 30155 1 0 32156 1 0 32157 1 0 33158 1 0 35159 1 0 36160 1 0 36161 1 0 37162 1 0 39163 1 0 39164 1 0 40165 1 0 40166 1 0 41167 1 0 43168 1 0 44169 1 0 44170 1 0 45171 1 0 45172 1 0 48173 1 0 48174 1 0 49175 1 0 49176 1 0 50177 1 0 50178 1 0 50179 1 0 51180 1 0 51181 1 0 51182 1 0 52183 1 0 52184 1 0 52185 1 0 53186 1 0 53187 1 0 54188 1 0 56189 1 0 57190 1 0 58191 1 0 59192 1 0 60193 1 0 60194 1 0 62195 1 0 63196 1 0 65197 1 0 66198 1 0 67199 1 0 68200 1 0 69201 1 0 71202 1 0 71203 1 0 71204 1 0 72205 1 0 74206 1 0 75207 1 0 76208 1 0 77209 1 0 78210 1 0 78211 1 0 81212 1 0 82213 1 0 83214 1 0 84215 1 0 85216 1 0 87217 1 0 87218 1 0 88219 1 0 90220 1 0 91221 1 0 92222 1 0 93223 1 0 94224 1 0 96225 1 0 96226 1 0 100227 1 0 101228 1 0 103229 1 0 106230 1 0 107231 1 0 109232 1 0 109233 1 0 109234 1 0 110235 1 0 111236 1 0 112237 1 0 113238 1 0 114239 1 0 115240 1 0 116241 1 0 117242 1 0 118243 1 0 119244 1 0 119245 1 0 119246 1 0 120247 1 0 120248 1 0 120249 1 0 121250 1 0 121251 1 0 121252 1 0 122253 1 0 123254 1 0 124255 1 0 125256 1 0 125257 1 0 126258 1 0 127259 1 0 128260 1 0 129261 1 0 M END

Standard InCHIKey	VHCSZQUYNKUEQK-XAOHDVSWSA-N
Standard InCHI	InChI=1S/C86H132O43/c1-33-50(93)56(99)62(105)74(117-33)125-68-41(26-87)119-72(65(108)59(68)102)115-30-44-54(97)58(101)64(107)77(123-44)129-80(111)86-22-20-81(3,4)25-37(86)36-12-14-47-82(5)18-17-48(83(6,32-89)46(82)16-19-85(47,8)84(36,7)21-23-86)124-79-71(52(95)39(91)28-114-79)128-78-67(110)70(51(94)34(2)118-78)127-73-61(104)55(98)45(31-116-73)121-75-66(109)60(103)69(42(27-88)120-75)126-76-63(106)57(100)53(96)43(122-76)29-113-49(92)15-11-35-10-13-40(112-9)38(90)24-35/h10-13,15,24,33-34,37,39,41-48,50-79,87-91,93-110H,14,16-23,25-32H2,1-9H3/b15-11+/t33-,34-,37-,39+,41+,42+,43+,44+,45+,46+,47+,48-,50-,51-,52-,53+,54+,55+,56+,57-,58-,59+,60+,61+,62+,63+,64+,65+,66+,67+,68+,69+,70+,71+,72+,73-,74-,75-,76-,77-,78-,79-,82-,83-,84+,85+,86-/m0/s1
SMILES	CC1C(C(C(C(O1)OC2C(OC(C(C2O)O)OCC3C(C(C(C(O3)OC(=O)C45CCC(CC4C6=CCC7C8(CCC(C(C8CCC7(C6(CC5)C)C)(C)CO)OC9C(C(C(CO9)O)O)OC1C(C(C(C(O1)C)O)OC1C(C(C(CO1)OC1C(C(C(C(O1)CO)OC1C(C(C(C(O1)COC(=O)C=CC1=CC(=C(C=C1)OC)O)O)O)O)O)O)O)O)O)C)(C)C)O)O)O)CO)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	1852.81	Volume:	1735.745 ? Van der Waals volume.
Dense:	1.067	LogP:	-1.971 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	-0.867 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.966 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	27.0	Rigid Bonds:	83.0
TPSA:	665.57 ? Topological Polar Surface Area.	H-Bond Acceptor:	43.0
H-Bond Donor:	23.0	Rings:	14.0
Heavy Atoms:	43.0

MedChem Properties

QED Drug-Likeness Score:	0.019	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	8.126	Fsp³:	0.86
MCE-18:	405.0 ? 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:	1	PAINS Alert:	0
Colloidal aggregators:	0.243	Fluc inhibitor:	0.265 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.092 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.645 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.386	Promiscuous compounds:	0.002

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-7.834	MDCK Permeability:	-4.766
Pgp-inhibitor:	0.0	Pgp-substrate:	1.0
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):	1.0
20% Bioavailability (F20%):	0.999	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	1.0
Plasma Protein Binding (PPB):	21.972%	Volume Distribution (VD):	-0.337
Fu:	28.082% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.0
OATP1B3 inhibitor:	0.205	BCRP inhibitor:	0.0
BSEP inhibitor:	0.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.892	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.997	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.055
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):

-2.398

Half-life (T1/2):

7.185

ADMET: Toxicity

hERG Blockers:	0.001	hERG Blockers (10um):	0.197
Human Hepatotoxicity (H-HT):	0.158	Drug-induced Liver Injury (DILI):	0.524
AMES Toxicity:	0.877	Rat Oral Acute Toxicity:	0.037
Maximum Recommended Daily Dose:	0.139	Skin Sensitization:	0.053
Carcinogencity:	0.0	Eye Corrosion:	0.0
Eye Irritation:	0.0	Respiratory Toxicity:	0.0
Drug-induced Neurotoxicity:	0.444	Ototoxicity:	1.0
Hematotoxicity:	0.0	Drug-induced Nephrotoxicity:	0.007
Genotoxicity:	0.0	RPMI-8226 Immunitoxicity:	0.396
A549 Cytotoxicity:	0.034	Hek293 Cytotoxicity:	0.993
BCF:	-0.094 ? 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:	4.105 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.654 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.304 ? 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
NPO6583	Clematis chinensis	Species	Ranunculaceae	Eukaryota	roots	n.a.	n.a.	PMID[15387651]
NPO6583	Clematis chinensis	Species	Ranunculaceae	Eukaryota	roots and rhizomes	Shaoguan, Guangdong Province, China	2007-Dec	PMID[20540535]
NPO6583	Clematis chinensis	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6583	Clematis chinensis	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO6583	Clematis chinensis	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6583	Clematis chinensis	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO6583	Clematis chinensis	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO6583	Clematis chinensis	Species	Ranunculaceae	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	2

Activity Type	# Activity
Individual protein	2

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT30	Individual protein	Cyclooxygenase-1	Homo sapiens	IC50	=	8900.0	nM	DrugMatrix in vivo data: Pathology
NPT31	Individual protein	Cyclooxygenase-2	Homo sapiens	IC50	=	7900.0	nM	PubChem BioAssay data set

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 NPC469775 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	15769
0.1-0.2	30272
0.2-0.3	2820
0.3-0.4	720
0.4-0.5	195
0.5-0.6	31
0.6-0.7	23
0.7-0.8	0
0.8-0.85	1
0.85-0.9	7
0.9-0.95	3
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.9424	High Similarity	NPC469776
0.9225	High Similarity	NPC469774
0.9034	High Similarity	NPC100925
0.8912	High Similarity	NPC469777
0.8733	High Similarity	NPC469772
0.8699	High Similarity	NPC32723
0.8639	High Similarity	NPC481323
0.8639	High Similarity	NPC469778
0.8618	High Similarity	NPC469773
0.8523	High Similarity	NPC135334
0.8247	Intermediate Similarity	NPC295941
0.7756	Intermediate Similarity	NPC481324
0.7754	Intermediate Similarity	NPC298034
0.7754	Intermediate Similarity	NPC71065
0.7681	Intermediate Similarity	NPC202828
0.7681	Intermediate Similarity	NPC119592
0.7259	Intermediate Similarity	NPC76972
0.7259	Intermediate Similarity	NPC469782
0.7259	Intermediate Similarity	NPC204414
0.7254	Intermediate Similarity	NPC261506
0.7254	Intermediate Similarity	NPC4328
0.7183	Intermediate Similarity	NPC236638
0.7183	Intermediate Similarity	NPC294453
0.7183	Intermediate Similarity	NPC305981
0.7113	Intermediate Similarity	NPC65105
0.7042	Intermediate Similarity	NPC41061
0.7042	Intermediate Similarity	NPC227551
0.6763	Remote Similarity	NPC60557
0.6763	Remote Similarity	NPC67857
0.6759	Remote Similarity	NPC293330
0.6644	Remote Similarity	NPC43550
0.6644	Remote Similarity	NPC250247
0.662	Remote Similarity	NPC135904
0.6503	Remote Similarity	NPC155410
0.6479	Remote Similarity	NPC79643
0.6475	Remote Similarity	NPC241909
0.6395	Remote Similarity	NPC110633
0.637	Remote Similarity	NPC481080
0.6358	Remote Similarity	NPC220160
0.6345	Remote Similarity	NPC100639
0.6294	Remote Similarity	NPC475287
0.6276	Remote Similarity	NPC123199
0.625	Remote Similarity	NPC192600
0.6207	Remote Similarity	NPC165204
0.6187	Remote Similarity	NPC475504
0.6081	Remote Similarity	NPC488560
0.6053	Remote Similarity	NPC481081
0.6014	Remote Similarity	NPC295823
0.6014	Remote Similarity	NPC174720
0.6014	Remote Similarity	NPC475467
0.5948	Remote Similarity	NPC136768
0.5906	Remote Similarity	NPC475160
0.5906	Remote Similarity	NPC473714
0.5894	Remote Similarity	NPC476068
0.5862	Remote Similarity	NPC481078
0.5817	Remote Similarity	NPC258617
0.5816	Remote Similarity	NPC102439
0.5779	Remote Similarity	NPC161717
0.5775	Remote Similarity	NPC63159
0.5745	Remote Similarity	NPC104071
0.5563	Remote Similarity	NPC112352
0.5535	Remote Similarity	NPC224381
0.5423	Remote Similarity	NPC295371
0.5385	Remote Similarity	NPC57484
0.5359	Remote Similarity	NPC133818
0.529	Remote Similarity	NPC471550
0.528	Remote Similarity	NPC70809
0.5238	Remote Similarity	NPC148417
0.522	Remote Similarity	NPC475514
0.5212	Remote Similarity	NPC480422
0.5188	Remote Similarity	NPC471385
0.5139	Remote Similarity	NPC473373
0.5102	Remote Similarity	NPC309714
0.5099	Remote Similarity	NPC481079
0.5062	Remote Similarity	NPC473452
0.5035	Remote Similarity	NPC48499
0.5034	Remote Similarity	NPC150400
0.5032	Remote Similarity	NPC475209
0.5032	Remote Similarity	NPC219180
0.5032	Remote Similarity	NPC251263
0.5029	Remote Similarity	NPC472268

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC469775 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6084
0.1-0.2	3023
0.2-0.3	41
0.3-0.4	2
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