NPASS Compound

Natural Product: NPC475368

Natural Product ID	NPC475368
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	3-O-Beta-D-Galactopyranosyl-(1->2)-[Beta-D-Xylopyranosyl-(1->3)]-Beta-D-Glucopyranosylgypsogenin-28-O-Beta-D-Xylopyranosyl-(1->3)-Beta-D-Xylopyranosyl-(1->4)-Alpha-L-Rhamnopyranosyl-(1->4)-[Alpha-L-Rhamnopyranosyl-(1->3)]-Beta-D-Fucopyranoside
IUPAC Name	(2S,3S,4S,5R,6R)-6-[[(3S,4S,4aR,6aR,6bS,8aS,12aS,14aR,14bR)-8a-[(2S,3R,4R,5S,6R)-5-[(2S,3R,4S,5R,6S)-5-[(2S,3R,4S,5R)-3,5-dihydroxy-4-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxyoxan-2-yl]oxy-3,4-dihydroxy-6-methyloxan-2-yl]oxy-3-hydroxy-6-methyl-4-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxycarbonyl-4-formyl-4,6a,6b,11,11,14b-hexamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy]-3-hydroxy-5-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxyoxane-2-carboxylic acid
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL504401
PubChem CID	44558934
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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38149 1 0 39150 1 0 40151 1 0 41152 1 0 42153 1 0 43154 1 0 44155 1 0 44156 1 0 44157 1 0 49158 1 0 49159 1 0 50160 1 0 50161 1 0 52162 1 0 52163 1 0 53164 1 0 55165 1 0 56166 1 0 56167 1 0 57168 1 0 59169 1 0 59170 1 0 60171 1 0 60172 1 0 61173 1 0 63174 1 0 64175 1 0 64176 1 0 65177 1 0 65178 1 0 68179 1 0 68180 1 0 69181 1 0 69182 1 0 70183 1 0 70184 1 0 70185 1 0 71186 1 0 71187 1 0 71188 1 0 72189 1 0 72190 1 0 72191 1 0 73192 1 0 76193 1 0 77194 1 0 78195 1 0 79196 1 0 80197 1 0 84198 1 0 85199 1 0 87200 1 0 88201 1 0 89202 1 0 90203 1 0 91204 1 0 91205 1 0 93206 1 0 94207 1 0 95208 1 0 97209 1 0 98210 1 0 99211 1 0 100212 1 0 101213 1 0 103214 1 0 103215 1 0 104216 1 0 105217 1 0 106218 1 0 107219 1 0 108220 1 0 108221 1 0 108222 1 0 109223 1 0 109224 1 0 109225 1 0 110226 1 0 110227 1 0 110228 1 0 111229 1 0 112230 1 0 113231 1 0 114232 1 0 M END

Standard InCHIKey	PHKMXPRTJWCJJJ-KAUSCZHPSA-N
Standard InCHI	InChI=1S/C75H118O39/c1-26-38(81)42(85)47(90)64(102-26)111-57-52(95)67(104-28(3)54(57)108-65-49(92)44(87)53(27(2)103-65)107-63-51(94)55(33(80)24-101-63)109-61-45(88)39(82)31(78)22-99-61)114-69(98)75-18-16-70(4,5)20-30(75)29-10-11-36-71(6)14-13-37(72(7,25-77)35(71)12-15-74(36,9)73(29,8)17-19-75)106-68-59(113-66-48(91)43(86)41(84)34(21-76)105-66)56(50(93)58(112-68)60(96)97)110-62-46(89)40(83)32(79)23-100-62/h10,25-28,30-59,61-68,76,78-95H,11-24H2,1-9H3,(H,96,97)/t26-,27-,28+,30-,31+,32+,33+,34+,35+,36+,37-,38-,39-,40-,41-,42+,43-,44-,45+,46+,47+,48+,49+,50-,51+,52+,53-,54-,55-,56-,57+,58-,59+,61-,62-,63-,64-,65-,66-,67-,68+,71-,72-,73+,74+,75-/m0/s1
SMILES	CC1C(C(C(C(O1)OC2C(C(OC(C2OC3C(C(C(C(O3)C)OC4C(C(C(CO4)O)OC5C(C(C(CO5)O)O)O)O)O)O)C)OC(=O)C67CCC(CC6C8=CCC9C1(CCC(C(C1CCC9(C8(CC7)C)C)(C)C=O)OC1C(C(C(C(O1)C(=O)O)O)OC1C(C(C(CO1)O)O)O)OC1C(C(C(C(O1)CO)O)O)O)C)(C)C)O)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	1642.73	Volume:	1526.794 ? Van der Waals volume.
Dense:	1.076	LogP:	-1.717 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	-0.629 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.905 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	20.0	Rigid Bonds:	77.0
TPSA:	603.49 ? Topological Polar Surface Area.	H-Bond Acceptor:	39.0
H-Bond Donor:	20.0	Rings:	13.0
Heavy Atoms:	39.0

MedChem Properties

QED Drug-Likeness Score:	0.025	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	7.51	Fsp³:	0.933
MCE-18:	285.586 ? 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:	0	PAINS Alert:	0
Colloidal aggregators:	0.001	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.003 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.579 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.425	Promiscuous compounds:	0.001

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-7.376	MDCK Permeability:	-4.826
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%):	0.989	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):	13.236%	Volume Distribution (VD):	-0.424
Fu:	32.055% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.0
OATP1B3 inhibitor:	0.001	BCRP inhibitor:	0.0
BSEP inhibitor:	0.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	1.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	1.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.009	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.0
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):

-2.441

Half-life (T1/2):

7.231

ADMET: Toxicity

hERG Blockers:	0.001	hERG Blockers (10um):	0.035
Human Hepatotoxicity (H-HT):	0.182	Drug-induced Liver Injury (DILI):	0.495
AMES Toxicity:	0.521	Rat Oral Acute Toxicity:	0.095
Maximum Recommended Daily Dose:	0.111	Skin Sensitization:	0.0
Carcinogencity:	0.0	Eye Corrosion:	0.0
Eye Irritation:	0.0	Respiratory Toxicity:	0.0
Drug-induced Neurotoxicity:	0.186	Ototoxicity:	1.0
Hematotoxicity:	0.0	Drug-induced Nephrotoxicity:	0.034
Genotoxicity:	0.036	RPMI-8226 Immunitoxicity:	0.174
A549 Cytotoxicity:	0.002	Hek293 Cytotoxicity:	0.926
BCF:	-0.126 ? 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:	3.905 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.292 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.996 ? 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
NPO24517	Acanthophyllum squarrosum	Species	Caryophyllaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11087591]
NPO24517	Acanthophyllum squarrosum	Species	Caryophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24517	Acanthophyllum squarrosum	Species	Caryophyllaceae	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
Activity	1

Activity Type	# Activity
Non-molecular	1

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
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	Activity	=	40.0	%	PMID[11087591]

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 NPC475368 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	25257
0.1-0.2	21258
0.2-0.3	2343
0.3-0.4	553
0.4-0.5	272
0.5-0.6	146
0.6-0.7	20
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
0.72	Intermediate Similarity	NPC187290
0.672	Remote Similarity	NPC475591
0.672	Remote Similarity	NPC236870
0.6579	Remote Similarity	NPC485563
0.6547	Remote Similarity	NPC302543
0.6308	Remote Similarity	NPC114484
0.6277	Remote Similarity	NPC488560
0.6268	Remote Similarity	NPC70809
0.6241	Remote Similarity	NPC481081
0.6224	Remote Similarity	NPC224381
0.6204	Remote Similarity	NPC475160
0.6204	Remote Similarity	NPC473714
0.6187	Remote Similarity	NPC57484
0.6164	Remote Similarity	NPC480422
0.6136	Remote Similarity	NPC301449
0.6136	Remote Similarity	NPC601290
0.6124	Remote Similarity	NPC46665
0.6094	Remote Similarity	NPC242840
0.6032	Remote Similarity	NPC475516
0.6	Remote Similarity	NPC159309
0.6	Remote Similarity	NPC86222
0.5986	Remote Similarity	NPC258617
0.5957	Remote Similarity	NPC476068
0.5926	Remote Similarity	NPC481078
0.5887	Remote Similarity	NPC85154
0.5857	Remote Similarity	NPC283417
0.5857	Remote Similarity	NPC100639
0.5857	Remote Similarity	NPC200049
0.585	Remote Similarity	NPC250247
0.5833	Remote Similarity	NPC476779
0.5827	Remote Similarity	NPC284449
0.5793	Remote Similarity	NPC202828
0.5793	Remote Similarity	NPC119592
0.5793	Remote Similarity	NPC236638
0.5793	Remote Similarity	NPC294453
0.5793	Remote Similarity	NPC305981
0.5775	Remote Similarity	NPC481080
0.5764	Remote Similarity	NPC484942
0.5758	Remote Similarity	NPC251768
0.5753	Remote Similarity	NPC261506
0.5753	Remote Similarity	NPC298034
0.5753	Remote Similarity	NPC71065
0.5753	Remote Similarity	NPC4328
0.5725	Remote Similarity	NPC112352
0.5724	Remote Similarity	NPC293330
0.5704	Remote Similarity	NPC281148
0.5694	Remote Similarity	NPC473452
0.5694	Remote Similarity	NPC286457
0.5674	Remote Similarity	NPC135904
0.5674	Remote Similarity	NPC123199
0.5655	Remote Similarity	NPC41061
0.5655	Remote Similarity	NPC227551
0.5639	Remote Similarity	NPC44716
0.562	Remote Similarity	NPC295823
0.562	Remote Similarity	NPC174720
0.562	Remote Similarity	NPC241909
0.562	Remote Similarity	NPC475467
0.5606	Remote Similarity	NPC192791
0.56	Remote Similarity	NPC480417
0.5594	Remote Similarity	NPC47995
0.5578	Remote Similarity	NPC110700
0.5578	Remote Similarity	NPC476777
0.5571	Remote Similarity	NPC475287
0.5547	Remote Similarity	NPC481079
0.554	Remote Similarity	NPC11242
0.5532	Remote Similarity	NPC79643
0.553	Remote Similarity	NPC263756
0.553	Remote Similarity	NPC469946
0.5524	Remote Similarity	NPC471550
0.5524	Remote Similarity	NPC191827
0.5517	Remote Similarity	NPC21691
0.551	Remote Similarity	NPC65105
0.551	Remote Similarity	NPC43550
0.5506	Remote Similarity	NPC472268
0.5461	Remote Similarity	NPC60557
0.5461	Remote Similarity	NPC76972
0.5461	Remote Similarity	NPC469782
0.5461	Remote Similarity	NPC300419
0.5461	Remote Similarity	NPC67857
0.5461	Remote Similarity	NPC204414
0.5455	Remote Similarity	NPC473884
0.5455	Remote Similarity	NPC157868
0.5448	Remote Similarity	NPC4749
0.5443	Remote Similarity	NPC297950
0.5441	Remote Similarity	NPC475504
0.5436	Remote Similarity	NPC309223
0.543	Remote Similarity	NPC279915
0.543	Remote Similarity	NPC476778
0.5407	Remote Similarity	NPC40775
0.5395	Remote Similarity	NPC102505
0.5395	Remote Similarity	NPC478825
0.5395	Remote Similarity	NPC488514
0.5361	Remote Similarity	NPC472269
0.5347	Remote Similarity	NPC155410
0.5338	Remote Similarity	NPC295371
0.5333	Remote Similarity	NPC30735
0.5328	Remote Similarity	NPC31193
0.5328	Remote Similarity	NPC297263
0.531	Remote Similarity	NPC470218
0.531	Remote Similarity	NPC602995
0.5303	Remote Similarity	NPC235405
0.5299	Remote Similarity	NPC213674
0.5294	Remote Similarity	NPC10607
0.529	Remote Similarity	NPC302887
0.5286	Remote Similarity	NPC160452
0.5278	Remote Similarity	NPC475899
0.527	Remote Similarity	NPC473645
0.527	Remote Similarity	NPC265841
0.527	Remote Similarity	NPC13998
0.5263	Remote Similarity	NPC478823
0.5263	Remote Similarity	NPC249848
0.5263	Remote Similarity	NPC107966
0.5255	Remote Similarity	NPC63159
0.5248	Remote Similarity	NPC104137
0.5248	Remote Similarity	NPC26626
0.5235	Remote Similarity	NPC470876
0.5232	Remote Similarity	NPC37860
0.5208	Remote Similarity	NPC192600
0.5203	Remote Similarity	NPC237191
0.5203	Remote Similarity	NPC484061
0.5203	Remote Similarity	NPC484062
0.5203	Remote Similarity	NPC473386
0.5185	Remote Similarity	NPC161674
0.5182	Remote Similarity	NPC473459
0.5177	Remote Similarity	NPC187618
0.5177	Remote Similarity	NPC96641
0.5177	Remote Similarity	NPC163183
0.5177	Remote Similarity	NPC80986
0.5175	Remote Similarity	NPC470475
0.517	Remote Similarity	NPC473918
0.5145	Remote Similarity	NPC68175
0.5145	Remote Similarity	NPC235438
0.5141	Remote Similarity	NPC31838
0.5135	Remote Similarity	NPC487505
0.5133	Remote Similarity	NPC475514
0.5132	Remote Similarity	NPC144644
0.5132	Remote Similarity	NPC170407
0.5115	Remote Similarity	NPC90856
0.5109	Remote Similarity	NPC117714
0.5108	Remote Similarity	NPC609763
0.5103	Remote Similarity	NPC123522
0.5099	Remote Similarity	NPC484059
0.5099	Remote Similarity	NPC484060
0.5097	Remote Similarity	NPC293031
0.5077	Remote Similarity	NPC209894
0.5074	Remote Similarity	NPC22956
0.507	Remote Similarity	NPC480473
0.5067	Remote Similarity	NPC488308
0.5067	Remote Similarity	NPC110633
0.5067	Remote Similarity	NPC480418
0.5067	Remote Similarity	NPC476780
0.5066	Remote Similarity	NPC136768
0.5065	Remote Similarity	NPC220160
0.5065	Remote Similarity	NPC267694
0.5064	Remote Similarity	NPC489209
0.5063	Remote Similarity	NPC480421
0.5061	Remote Similarity	NPC485564
0.5038	Remote Similarity	NPC48499
0.5037	Remote Similarity	NPC58448
0.5036	Remote Similarity	NPC223301
0.5036	Remote Similarity	NPC171544
0.5034	Remote Similarity	NPC71391
0.5034	Remote Similarity	NPC470476
0.5033	Remote Similarity	NPC271610
0.5033	Remote Similarity	NPC312650
0.5031	Remote Similarity	NPC478822
0.503	Remote Similarity	NPC220838

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC475368 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7319
0.1-0.2	1787
0.2-0.3	40
0.3-0.4	4
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