NPASS Compound

Natural Product: NPC568320

Natural Product ID	NPC568320
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	5-hydroxy-3-(3-hydroxy-4,5-dimethoxy-phenyl)-7-[(2~{R},3~{S},4~{R},5~{R},6~{S})-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-chromen-4-one
IUPAC Name	5-hydroxy-3-(3-hydroxy-4,5-dimethoxy-phenyl)-7-[(2~{R},3~{S},4~{R},5~{R},6~{S})-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-chromen-4-one
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	n.a.
Chemical Classification	CHEMONTID:0000000 [Organic compounds]

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 59 62 0 0 0 0 0 0 0 0999 V2000 6.2462 -2.7894 -0.6091 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0083 -1.6290 -0.8819 O 0 0 0 0 0 0 0 0 0 0 0 0 6.3259 -0.4027 -0.8143 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9842 -0.3212 -0.4996 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3400 0.8965 -0.4404 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9179 1.0167 -0.1094 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4698 1.9670 0.7836 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2080 2.0998 1.0999 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2875 1.3076 0.5621 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0371 1.4388 0.8871 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0549 0.6283 0.3491 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3326 0.8646 0.7574 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.4392 0.1620 0.3269 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.0488 -0.3969 1.4599 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0199 -1.3282 1.0781 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.3770 -2.1467 2.2881 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.3346 -3.1052 2.0256 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.1814 -0.5576 0.5213 C 0 0 2 0 0 0 0 0 0 0 0 0 -8.2167 -1.3742 0.1003 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.6669 0.2134 -0.6892 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.6952 1.0226 -1.2048 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.4664 1.0495 -0.3678 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.8873 1.4277 -1.5925 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6358 -0.3285 -0.5448 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2913 -0.4917 -0.9007 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0836 -1.4704 -1.8064 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6565 0.3305 -0.3414 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9829 0.1927 -0.6723 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3544 -0.6800 -1.4859 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1057 2.0111 -0.7105 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4469 1.9325 -1.0253 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2201 3.0693 -1.2990 O 0 0 0 0 0 0 0 0 0 0 0 0 7.0912 0.7142 -1.0845 C 0 0 0 0 0 0 0 0 0 0 0 0 8.4419 0.6029 -1.3990 O 0 0 0 0 0 0 0 0 0 0 0 0 9.4086 0.6403 -0.3584 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4952 -3.0033 -1.4017 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8928 -3.6883 -0.5157 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6849 -2.7160 0.3426 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4176 -1.2271 -0.2934 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1980 2.6300 1.2403 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2851 2.2274 1.6083 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1624 -0.6161 -0.3900 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6157 -1.9746 0.2609 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6961 -1.4430 3.0907 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4358 -2.6265 2.6423 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0425 -3.6074 1.2274 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5007 0.1700 1.2965 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.4272 -1.2346 -0.8388 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3907 -0.5178 -1.4804 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.6201 1.8861 -0.7134 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7298 1.9276 0.2409 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8208 2.3919 -1.6774 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3613 -0.9851 -0.9965 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3675 -2.3917 -1.8066 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6116 2.9862 -0.6683 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2652 3.3320 -2.2923 H 0 0 0 0 0 0 0 0 0 0 0 0 9.9966 -0.3000 -0.2986 H 0 0 0 0 0 0 0 0 0 0 0 0 8.9008 0.7309 0.6410 H 0 0 0 0 0 0 0 0 0 0 0 0 10.0981 1.4828 -0.4365 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 3 4 2 0 4 5 1 0 5 6 1 0 6 7 2 0 7 8 1 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 14 15 1 0 15 16 1 0 16 17 1 0 15 18 1 0 18 19 1 0 18 20 1 0 20 21 1 0 20 22 1 0 22 23 1 0 11 24 2 0 24 25 1 0 25 26 1 0 25 27 2 0 27 28 1 0 28 29 2 0 5 30 2 0 30 31 1 0 31 32 1 0 31 33 2 0 33 34 1 0 34 35 1 0 33 3 1 0 28 6 1 0 27 9 1 0 22 13 1 0 1 36 1 0 1 37 1 0 1 38 1 0 4 39 1 0 7 40 1 0 10 41 1 0 13 42 1 6 15 43 1 6 16 44 1 0 16 45 1 0 17 46 1 0 18 47 1 1 19 48 1 0 20 49 1 6 21 50 1 0 22 51 1 1 23 52 1 0 24 53 1 0 26 54 1 0 30 55 1 0 32 56 1 0 35 57 1 0 35 58 1 0 35 59 1 0 M END

Standard InCHIKey	MMXONNAQYTURLK-QRDGOAKLSA-N
Standard InCHI	InChI=1S/C23H24O12/c1-31-15-4-9(3-13(26)22(15)32-2)11-8-33-14-6-10(5-12(25)17(14)18(11)27)34-23-21(30)20(29)19(28)16(7-24)35-23/h3-6,8,16,19-21,23-26,28-30H,7H2,1-2H3/t16-,19-,20+,21-,23-/m0/s1
SMILES	COC1=CC(C2=COC3=CC(O[C@H]4O[C@@H](CO)[C@H](O)[C@@H](O)[C@@H]4O)=CC(O)=C3C2=O)=CC(O)=C1OC

Calculated Properties

Physi-Chem Properties

Molecular Weight:	492.13	Volume:	456.529 ? Van der Waals volume.
Dense:	1.078	LogP:	-0.133 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	0.885 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.792 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	6.0	Rigid Bonds:	24.0
TPSA:	188.51 ? Topological Polar Surface Area.	H-Bond Acceptor:	12.0
H-Bond Donor:	6.0	Rings:	4.0
Heavy Atoms:	12.0

MedChem Properties

QED Drug-Likeness Score:	0.272	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.039	Fsp³:	0.348
MCE-18:	89.71 ? 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:	0
Colloidal aggregators:	0.58	Fluc inhibitor:	0.187 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.91 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.826 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.099	Promiscuous compounds:	0.684

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.367	MDCK Permeability:	-5.397
Pgp-inhibitor:	0.001	Pgp-substrate:	0.45
PAMPA:	0.974 ? 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):	0.812
20% Bioavailability (F20%):	0.233	30% Bioavailability (F30%):	0.98
50% Bioavailability (F50%):	0.989

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.046	MRP1:	0.388
Plasma Protein Binding (PPB):	82.83%	Volume Distribution (VD):	-0.063
Fu:	17.019% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.994
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.7
BSEP inhibitor:	0.01

ADMET: Metabolism

CYP1A2-inhibitor:	0.174	CYP1A2-substrate:	0.001
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.001
CYP2C9-inhibitor:	0.11	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.027	CYP2D6-substrate:	0.018
CYP3A4-inhibitor:	0.002	CYP3A4-substrate:	0.226
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.366
HLM stability:	0.11 ? 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):

2.218

Half-life (T1/2):

2.742

ADMET: Toxicity

hERG Blockers:	0.03	hERG Blockers (10um):	0.234
Human Hepatotoxicity (H-HT):	0.608	Drug-induced Liver Injury (DILI):	0.981
AMES Toxicity:	0.758	Rat Oral Acute Toxicity:	0.089
Maximum Recommended Daily Dose:	0.073	Skin Sensitization:	0.883
Carcinogencity:	0.141	Eye Corrosion:	0.0
Eye Irritation:	0.309	Respiratory Toxicity:	0.065
Drug-induced Neurotoxicity:	0.012	Ototoxicity:	0.832
Hematotoxicity:	0.158	Drug-induced Nephrotoxicity:	0.751
Genotoxicity:	0.499	RPMI-8226 Immunitoxicity:	0.271
A549 Cytotoxicity:	0.537	Hek293 Cytotoxicity:	0.212
BCF:	0.464 ? 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:	3.121 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.609 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.774 ? 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
NPO7478	Iris germanica	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19299148]
NPO7478	Iris germanica	Species	Iridaceae	Eukaryota	n.a.	rhizome	n.a.	PMID[22388969]
NPO7478	Iris germanica	Species	Iridaceae	Eukaryota	n.a.	rhizome	n.a.	PMID[25204177]
NPO7478	Iris germanica	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7478	Iris germanica	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7478	Iris germanica	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7478	Iris germanica	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]

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 NPC568320 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	23708
0.1-0.2	22432
0.2-0.3	2571
0.3-0.4	861
0.4-0.5	203
0.5-0.6	61
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
0.8267	Intermediate Similarity	NPC224462
0.7763	Intermediate Similarity	NPC73511
0.7632	Intermediate Similarity	NPC197896
0.7632	Intermediate Similarity	NPC313163
0.7179	Intermediate Similarity	NPC234739
0.6951	Remote Similarity	NPC307518
0.6914	Remote Similarity	NPC80140
0.6667	Remote Similarity	NPC48773
0.6627	Remote Similarity	NPC229729
0.6585	Remote Similarity	NPC205076
0.6506	Remote Similarity	NPC481043
0.65	Remote Similarity	NPC160515
0.6477	Remote Similarity	NPC479405
0.642	Remote Similarity	NPC348541
0.6404	Remote Similarity	NPC479404
0.6145	Remote Similarity	NPC156457
0.6098	Remote Similarity	NPC45165
0.6092	Remote Similarity	NPC479407
0.6047	Remote Similarity	NPC22832
0.6047	Remote Similarity	NPC243930
0.6	Remote Similarity	NPC100720
0.5955	Remote Similarity	NPC487212
0.5952	Remote Similarity	NPC105511
0.5952	Remote Similarity	NPC95090
0.5952	Remote Similarity	NPC161749
0.5952	Remote Similarity	NPC27408
0.5914	Remote Similarity	NPC479403
0.5904	Remote Similarity	NPC135345
0.5814	Remote Similarity	NPC138540
0.5795	Remote Similarity	NPC311830
0.5795	Remote Similarity	NPC607707
0.5747	Remote Similarity	NPC479402
0.5698	Remote Similarity	NPC84362
0.5682	Remote Similarity	NPC284960
0.5682	Remote Similarity	NPC486578
0.5682	Remote Similarity	NPC601607
0.5647	Remote Similarity	NPC289667
0.5647	Remote Similarity	NPC261866
0.5618	Remote Similarity	NPC607201
0.5591	Remote Similarity	NPC303913
0.5581	Remote Similarity	NPC189142
0.5581	Remote Similarity	NPC77660
0.5568	Remote Similarity	NPC285197
0.5556	Remote Similarity	NPC191154
0.5506	Remote Similarity	NPC601144
0.5488	Remote Similarity	NPC134819
0.5465	Remote Similarity	NPC39360
0.5465	Remote Similarity	NPC29763
0.5465	Remote Similarity	NPC210003
0.5455	Remote Similarity	NPC60966
0.5455	Remote Similarity	NPC481044
0.5444	Remote Similarity	NPC479406
0.5402	Remote Similarity	NPC297987
0.5402	Remote Similarity	NPC487213
0.5402	Remote Similarity	NPC258035
0.5402	Remote Similarity	NPC277205
0.5402	Remote Similarity	NPC37919
0.5402	Remote Similarity	NPC136042
0.5393	Remote Similarity	NPC479401
0.5385	Remote Similarity	NPC601586
0.5287	Remote Similarity	NPC58053
0.5269	Remote Similarity	NPC251417
0.5227	Remote Similarity	NPC323593
0.5227	Remote Similarity	NPC203500
0.5227	Remote Similarity	NPC603782
0.5195	Remote Similarity	NPC250557
0.519	Remote Similarity	NPC114192
0.5169	Remote Similarity	NPC22195
0.5169	Remote Similarity	NPC186807
0.5169	Remote Similarity	NPC21190
0.5165	Remote Similarity	NPC605067
0.5165	Remote Similarity	NPC610187
0.5132	Remote Similarity	NPC116632
0.5109	Remote Similarity	NPC116458
0.5109	Remote Similarity	NPC246943
0.5109	Remote Similarity	NPC605784
0.5065	Remote Similarity	NPC303644
0.5055	Remote Similarity	NPC307938
0.5055	Remote Similarity	NPC609451
0.5054	Remote Similarity	NPC267254
0.5051	Remote Similarity	NPC257714
0.505	Remote Similarity	NPC235575

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC568320 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5555
0.1-0.2	3530
0.2-0.3	51
0.3-0.4	9
0.4-0.5	4
0.5-0.6	1
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
0.5952	Remote Similarity	NPD4381	Clinical (unspecified phase)

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