NPASS Compound

Natural Product: NPC321638

Natural Product ID	NPC321638
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Beta-(3,4-Dihydroxyphenyl)Ethyl-6-O-E-Caffeoyl-O-[Beta-D-Apiofuranosyl-(1->2)]-Beta-D-Glucopyranoside
IUPAC Name	[(2R,3S,4S,5R,6R)-5-[(2S,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy-6-[2-(3,4-dihydroxyphenyl)ethoxy]-3,4-dihydroxyoxan-2-yl]methyl (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL1689258
PubChem CID	51042401
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000476] Cinnamic acids and derivatives [CHEMONTID:0001391] Hydroxycinnamic acids and derivatives [CHEMONTID:0000059] Coumaric acids and derivatives

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 77 80 0 0 0 0 0 0 0 0999 V2000 -1.0547 5.8466 1.4747 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.9261 6.5357 0.6368 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6206 5.5331 -0.2417 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.5181 6.1288 -1.1207 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6363 4.6378 -0.9665 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3991 3.5347 -1.2548 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.1925 3.2545 -0.1225 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.3406 4.5155 0.6228 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.6782 4.9406 0.7434 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6599 2.1908 0.5078 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3557 1.0252 0.5176 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5672 -0.1092 -0.1877 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.1893 -1.2918 0.0935 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.7982 -1.9716 -0.8950 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9964 -2.4549 -2.0461 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9203 -3.3954 -1.7173 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6462 -2.9585 -1.4922 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3678 -3.8695 -1.1683 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0676 -5.2004 -1.0807 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2098 -5.6655 -1.3038 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1998 -4.7372 -1.6242 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4775 -7.0223 -1.2064 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0881 -6.1067 -0.7560 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2808 -0.1612 0.2529 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9901 0.4213 1.4349 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.0562 0.4349 2.4664 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.4500 0.5319 1.9458 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.0236 -0.7382 2.0165 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8159 1.5528 3.2988 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1919 -0.3507 2.0440 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3120 -0.2905 1.1821 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4943 -0.9251 1.5331 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5564 -1.5481 2.6150 O 0 0 0 0 0 0 0 0 0 0 0 0 3.6708 -0.8754 0.6538 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7784 -1.4700 0.9806 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0033 -1.4798 0.1759 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1390 -2.1409 0.5986 C 0 0 0 0 0 0 0 0 0 0 0 0 8.2951 -2.1556 -0.1493 C 0 0 0 0 0 0 0 0 0 0 0 0 8.3581 -1.5037 -1.3583 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2461 -0.8406 -1.8005 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0841 -0.8318 -1.0382 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3092 -0.1795 -3.0257 O 0 0 0 0 0 0 0 0 0 0 0 0 9.5331 -1.5191 -2.1177 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3835 6.4795 1.8508 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7038 6.9828 1.3018 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4582 7.3530 0.0922 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0397 6.7935 -0.6037 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3458 5.1549 -1.9033 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8045 4.3715 -0.3141 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1952 2.9739 -0.5610 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9074 4.5598 1.6169 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0845 4.9584 -0.1645 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3224 1.0518 -0.0040 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5925 0.1854 -1.2465 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2317 -2.9034 -0.4102 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7134 -1.4800 -1.3100 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6615 -3.0000 -2.7834 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5508 -1.6395 -2.6577 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3354 -1.9272 -1.5520 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3726 -3.5035 -0.9928 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1886 -5.1577 -1.7895 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4092 -7.3970 -1.0828 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9293 -6.7368 0.0285 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5666 1.4464 1.2325 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9835 -0.4446 3.1717 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0362 1.2082 2.5902 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2674 -0.8708 2.9780 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.8150 3.2688 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0979 -1.4080 2.2399 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4387 0.0931 3.0308 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6109 -0.3374 -0.2749 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8071 -2.0098 1.9328 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0761 -2.6546 1.5604 H 0 0 0 0 0 0 0 0 0 0 0 0 9.1725 -2.6904 0.2210 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2493 -0.2892 -1.4505 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2150 0.8456 -2.9991 H 0 0 0 0 0 0 0 0 0 0 0 0 10.3817 -1.1139 -1.7181 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 3 4 1 6 3 5 1 0 5 6 1 0 6 7 1 0 7 8 1 0 8 9 1 0 7 10 1 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 2 0 17 18 1 0 18 19 2 0 19 20 1 0 20 21 2 0 20 22 1 0 19 23 1 0 12 24 1 0 24 25 1 0 25 26 1 0 26 27 1 0 27 28 1 0 26 29 1 0 25 30 1 0 30 31 1 0 31 32 1 0 32 33 2 0 32 34 1 0 34 35 2 0 35 36 1 0 36 37 2 0 37 38 1 0 38 39 2 0 39 40 1 0 40 41 2 0 40 42 1 0 39 43 1 0 8 3 1 0 27 11 1 0 41 36 1 0 21 16 1 0 1 44 1 0 2 45 1 0 2 46 1 0 4 47 1 0 5 48 1 0 5 49 1 0 7 50 1 6 8 51 1 1 9 52 1 0 11 53 1 6 12 54 1 6 14 55 1 0 14 56 1 0 15 57 1 0 15 58 1 0 17 59 1 0 18 60 1 0 21 61 1 0 22 62 1 0 23 63 1 0 25 64 1 6 26 65 1 1 27 66 1 1 28 67 1 0 29 68 1 0 30 69 1 0 30 70 1 0 34 71 1 0 35 72 1 0 37 73 1 0 38 74 1 0 41 75 1 0 42 76 1 0 43 77 1 0 M END

Standard InCHIKey	NSDMGXRVIBQWAN-FQMHKDNFSA-N
Standard InCHI	InChI=1S/C28H34O15/c29-12-28(38)13-41-27(25(28)37)43-24-23(36)22(35)20(11-40-21(34)6-3-14-1-4-16(30)18(32)9-14)42-26(24)39-8-7-15-2-5-17(31)19(33)10-15/h1-6,9-10,20,22-27,29-33,35-38H,7-8,11-13H2/b6-3+/t20-,22-,23+,24-,25+,26-,27+,28-/m1/s1
SMILES	OC[C@@]1(O)CO[C@H]([C@@H]1O)O[C@H]1[C@H](OCCc2ccc(c(c2)O)O)O[C@@H]([C@H]([C@@H]1O)O)COC(=O)/C=C/c1ccc(c(c1)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	610.19	Volume:	569.38 ? Van der Waals volume.
Dense:	1.072	LogP:	0.889 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.299 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.814 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	12.0	Rigid Bonds:	25.0
TPSA:	245.29 ? Topological Polar Surface Area.	H-Bond Acceptor:	15.0
H-Bond Donor:	9.0	Rings:	4.0
Heavy Atoms:	15.0

MedChem Properties

QED Drug-Likeness Score:	0.081	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.705	Fsp³:	0.464
MCE-18:	99.732 ? 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:	0.637	Fluc inhibitor:	0.639 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.104 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.624 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.197	Promiscuous compounds:	0.484

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.541	MDCK Permeability:	-5.269
Pgp-inhibitor:	0.0	Pgp-substrate:	0.025
PAMPA:	0.997 ? 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):	0.903
20% Bioavailability (F20%):	1.0	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.003	MRP1:	0.029
Plasma Protein Binding (PPB):	70.885%	Volume Distribution (VD):	-0.225
Fu:	25.006% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.098
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:	0.009
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.017 ? 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):

3.638

Half-life (T1/2):

2.761

ADMET: Toxicity

hERG Blockers:	0.052	hERG Blockers (10um):	0.602
Human Hepatotoxicity (H-HT):	0.513	Drug-induced Liver Injury (DILI):	0.759
AMES Toxicity:	0.913	Rat Oral Acute Toxicity:	0.033
Maximum Recommended Daily Dose:	0.196	Skin Sensitization:	1.0
Carcinogencity:	0.144	Eye Corrosion:	0.0
Eye Irritation:	0.455	Respiratory Toxicity:	0.006
Drug-induced Neurotoxicity:	0.001	Ototoxicity:	0.984
Hematotoxicity:	0.023	Drug-induced Nephrotoxicity:	0.299
Genotoxicity:	0.908	RPMI-8226 Immunitoxicity:	0.022
A549 Cytotoxicity:	0.977	Hek293 Cytotoxicity:	0.608
BCF:	0.728 ? 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:	3.356 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.955 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.473 ? 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
NPO19548	Lepisorus contortus	Species	Polypodiaceae	Eukaryota	whole plant	Gongshan County, Yunnan, China	n.a.	PMID[21261296]
NPO19548	Lepisorus contortus	Species	Polypodiaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[21261296]
NPO19548	Lepisorus contortus	Species	Polypodiaceae	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	1

Activity Type	# Activity
Individual protein	1

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT441	Individual protein	Cytochrome P450 19A1	Homo sapiens	IC50	=	32300.0	nM	PMID[21261296]

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 NPC321638 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	16947
0.1-0.2	30116
0.2-0.3	2269
0.3-0.4	399
0.4-0.5	90
0.5-0.6	25
0.6-0.7	6
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
0.7073	Intermediate Similarity	NPC171134
0.7	Intermediate Similarity	NPC141455
0.6538	Remote Similarity	NPC287597
0.6512	Remote Similarity	NPC321184
0.6471	Remote Similarity	NPC40305
0.6471	Remote Similarity	NPC328273
0.604	Remote Similarity	NPC188393
0.6022	Remote Similarity	NPC476397
0.5979	Remote Similarity	NPC196063
0.5979	Remote Similarity	NPC604195
0.5976	Remote Similarity	NPC34293
0.5926	Remote Similarity	NPC473924
0.5914	Remote Similarity	NPC105005
0.5895	Remote Similarity	NPC610636
0.5784	Remote Similarity	NPC229505
0.575	Remote Similarity	NPC90318
0.5732	Remote Similarity	NPC78363
0.573	Remote Similarity	NPC205195
0.5684	Remote Similarity	NPC296954
0.5591	Remote Similarity	NPC47471
0.557	Remote Similarity	NPC608074
0.5556	Remote Similarity	NPC64141
0.551	Remote Similarity	NPC300894
0.551	Remote Similarity	NPC23845
0.5435	Remote Similarity	NPC68092
0.5357	Remote Similarity	NPC886
0.5352	Remote Similarity	NPC147654
0.5301	Remote Similarity	NPC288416
0.5238	Remote Similarity	NPC229784
0.5192	Remote Similarity	NPC476398
0.5111	Remote Similarity	NPC473799
0.51	Remote Similarity	NPC96795
0.51	Remote Similarity	NPC264632

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC321638 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5323
0.1-0.2	3780
0.2-0.3	44
0.3-0.4	2
0.4-0.5	1
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