NPASS Compound

Natural Product: NPC26385

Natural Product ID	NPC26385
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	HZCOWROLPVDVCR-XMPPFBFMSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	11656956
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000253] Stilbenes [CHEMONTID:0000142] Stilbene 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 66 69 0 0 0 0 0 0 0 0999 V2000 6.6051 0.1991 -1.1479 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5102 0.1162 -0.4537 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1667 -0.0636 -0.9905 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8993 -0.1670 -2.3337 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6113 -0.3394 -2.8176 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5602 -0.4096 -1.9206 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7745 -0.3119 -0.5725 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0881 -0.1395 -0.1398 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7993 -0.3693 0.4021 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5592 -0.5379 0.1991 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.1211 -1.7280 0.9690 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7432 -1.3013 2.2683 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.9294 -0.3939 1.9177 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5841 0.3444 0.6322 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.2894 1.6827 0.5622 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6782 1.5661 0.5180 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.3745 0.8941 -0.4836 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7190 0.3697 -1.3891 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.8280 0.8570 -0.3930 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.5390 1.4494 0.6269 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.9260 1.3935 0.6838 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.6293 0.7297 -0.3014 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.9337 0.1303 -1.3309 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.5443 0.1983 -1.3685 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.6259 -0.5392 -2.3266 O 0 0 0 0 0 0 0 0 0 0 0 0 -11.0257 0.6901 -0.2178 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.6371 1.9924 1.7141 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2158 0.6028 0.6734 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.0401 -1.1842 1.6710 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8332 -0.4868 2.9396 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.0476 -2.4457 0.2229 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4056 -0.4363 -4.1697 O 0 0 0 0 0 0 0 0 0 0 0 0 7.9413 0.3788 -0.5951 C 0 0 0 0 0 0 0 0 0 0 0 0 9.0322 0.4475 -1.4426 C 0 0 0 0 0 0 0 0 0 0 0 0 10.3199 0.6168 -0.9757 C 0 0 0 0 0 0 0 0 0 0 0 0 10.5468 0.7227 0.3714 C 0 0 0 0 0 0 0 0 0 0 0 0 9.4904 0.6594 1.2450 C 0 0 0 0 0 0 0 0 0 0 0 0 8.2104 0.4890 0.7452 C 0 0 0 0 0 0 0 0 0 0 0 0 9.7349 0.7687 2.6136 O 0 0 0 0 0 0 0 0 0 0 0 0 11.8446 0.8928 0.8341 O 0 0 0 0 0 0 0 0 0 0 0 0 6.4876 0.1256 -2.2394 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6337 0.1910 0.6380 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6860 -0.1174 -3.0584 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5581 -0.5436 -2.2953 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2902 -0.0592 0.9151 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8266 -0.6415 -0.8651 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2952 -2.4281 1.2088 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0443 -2.1830 2.8343 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0592 0.2906 2.7680 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7834 -0.2793 -0.2420 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8678 2.2276 -0.3033 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0160 2.2376 1.4790 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9916 1.9648 1.3906 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9769 -0.2750 -2.1830 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.5190 -0.1311 -2.6031 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.5300 -0.1722 -0.1256 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.2259 1.8715 2.6501 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8451 -2.1502 1.7477 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1854 -0.1847 3.8174 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0793 -3.3707 0.5837 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8937 -1.0898 -4.7721 H 0 0 0 0 0 0 0 0 0 0 0 0 8.8770 0.3673 -2.4959 H 0 0 0 0 0 0 0 0 0 0 0 0 11.1423 0.6633 -1.6953 H 0 0 0 0 0 0 0 0 0 0 0 0 7.4213 0.4464 1.4736 H 0 0 0 0 0 0 0 0 0 0 0 0 9.5087 1.5988 3.1372 H 0 0 0 0 0 0 0 0 0 0 0 0 12.0302 0.6390 1.7957 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 2 3 1 0 3 4 2 0 4 5 1 0 5 6 2 0 6 7 1 0 7 8 2 0 7 9 1 0 9 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 1 0 17 18 2 0 17 19 1 0 19 20 2 0 20 21 1 0 21 22 2 0 22 23 1 0 23 24 2 0 23 25 1 0 22 26 1 0 21 27 1 0 14 28 1 0 13 29 1 0 12 30 1 0 11 31 1 0 5 32 1 0 1 33 1 0 33 34 2 0 34 35 1 0 35 36 2 0 36 37 1 0 37 38 2 0 37 39 1 0 36 40 1 0 8 3 1 0 28 10 1 0 38 33 1 0 24 19 1 0 1 41 1 0 2 42 1 0 4 43 1 0 6 44 1 0 8 45 1 0 10 46 1 6 11 47 1 1 12 48 1 1 13 49 1 1 14 50 1 6 15 51 1 0 15 52 1 0 20 53 1 0 24 54 1 0 25 55 1 0 26 56 1 0 27 57 1 0 29 58 1 0 30 59 1 0 31 60 1 0 32 61 1 0 34 62 1 0 35 63 1 0 38 64 1 0 39 65 1 0 40 66 1 0 M END

Standard InCHIKey	HZCOWROLPVDVCR-XMPPFBFMSA-N
Standard InCHI	InChI=1S/C27H26O13/c28-15-5-13(2-1-12-3-4-17(29)18(30)7-12)6-16(10-15)39-27-25(36)24(35)23(34)21(40-27)11-38-26(37)14-8-19(31)22(33)20(32)9-14/h1-10,21,23-25,27-36H,11H2/b2-1+/t21-,23-,24+,25-,27-/m1/s1
SMILES	C(=Cc1cc(cc(c1)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](COC(=O)c2cc(c(c(c2)O)O)O)O1)O)O)O)O)/c1ccc(c(c1)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	558.14	Volume:	526.594 ? Van der Waals volume.
Dense:	1.06	LogP:	1.402 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.528 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.098 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	8.0	Rigid Bonds:	26.0
TPSA:	226.83 ? Topological Polar Surface Area.	H-Bond Acceptor:	13.0
H-Bond Donor:	9.0	Rings:	4.0
Heavy Atoms:	13.0

MedChem Properties

QED Drug-Likeness Score:	0.113	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.146	Fsp³:	0.222
MCE-18:	92.485 ? 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:	1
Colloidal aggregators:	0.777	Fluc inhibitor:	0.967 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.23 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.973 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.415	Promiscuous compounds:	0.934

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.674	MDCK Permeability:	-5.01
Pgp-inhibitor:	0.0	Pgp-substrate:	0.0
PAMPA:	0.99 ? 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):	0.001
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:	0.991
Plasma Protein Binding (PPB):	82.906%	Volume Distribution (VD):	-0.082
Fu:	18.045% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.999
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.683
BSEP inhibitor:	0.003

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:	0.99
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.999
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.585 ? 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):

4.168

Half-life (T1/2):

3.982

ADMET: Toxicity

hERG Blockers:	0.106	hERG Blockers (10um):	0.884
Human Hepatotoxicity (H-HT):	0.246	Drug-induced Liver Injury (DILI):	0.894
AMES Toxicity:	0.796	Rat Oral Acute Toxicity:	0.034
Maximum Recommended Daily Dose:	0.648	Skin Sensitization:	1.0
Carcinogencity:	0.072	Eye Corrosion:	0.0
Eye Irritation:	0.856	Respiratory Toxicity:	0.013
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	0.976
Hematotoxicity:	0.001	Drug-induced Nephrotoxicity:	0.014
Genotoxicity:	0.966	RPMI-8226 Immunitoxicity:	0.011
A549 Cytotoxicity:	0.999	Hek293 Cytotoxicity:	0.578
BCF:	0.92 ? 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:	3.688 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.078 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.623 ? 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
NPO21036	Celaenodendron mexicanum	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[19299148]
NPO21542	Vernonia menthaefolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21164	Veratrum dahuricum	Species	Melanthiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17130	Hylotelephium telephium	Species	Crassulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19969	Dermocybe canaria	Species	Cortinariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21036	Celaenodendron mexicanum	Species	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18859	Carica pennata	Species	Caricaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20715	Astragalus cibarius	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21918	Aconitum heterophylloides	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20715	Astragalus cibarius	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO20715	Astragalus cibarius	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20715	Astragalus cibarius	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21918	Aconitum heterophylloides	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19969	Dermocybe canaria	Species	Cortinariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21036	Celaenodendron mexicanum	Species	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO21542	Vernonia menthaefolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18859	Carica pennata	Species	Caricaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21164	Veratrum dahuricum	Species	Melanthiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17130	Hylotelephium telephium	Species	Crassulaceae	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

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 NPC26385 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	17542
0.1-0.2	27956
0.2-0.3	3588
0.3-0.4	627
0.4-0.5	104
0.5-0.6	26
0.6-0.7	9
0.7-0.8	0
0.8-0.85	1
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8986	High Similarity	NPC289346
0.8243	Intermediate Similarity	NPC33298
0.6528	Remote Similarity	NPC242028
0.6528	Remote Similarity	NPC203230
0.6301	Remote Similarity	NPC484156
0.6184	Remote Similarity	NPC25389
0.6133	Remote Similarity	NPC166277
0.6076	Remote Similarity	NPC130496
0.6053	Remote Similarity	NPC472859
0.6	Remote Similarity	NPC40664
0.6	Remote Similarity	NPC197723
0.5974	Remote Similarity	NPC1913
0.5949	Remote Similarity	NPC160780
0.5909	Remote Similarity	NPC479369
0.56	Remote Similarity	NPC85799
0.56	Remote Similarity	NPC303422
0.56	Remote Similarity	NPC65833
0.5581	Remote Similarity	NPC479375
0.5385	Remote Similarity	NPC8497
0.5309	Remote Similarity	NPC215811
0.5301	Remote Similarity	NPC311803
0.5278	Remote Similarity	NPC92117
0.5256	Remote Similarity	NPC294166
0.5256	Remote Similarity	NPC115022
0.525	Remote Similarity	NPC98777
0.525	Remote Similarity	NPC212770
0.5227	Remote Similarity	NPC285108
0.5195	Remote Similarity	NPC218003
0.5122	Remote Similarity	NPC119125
0.5122	Remote Similarity	NPC4958
0.5119	Remote Similarity	NPC157898
0.51	Remote Similarity	NPC67629
0.51	Remote Similarity	NPC79736
0.5057	Remote Similarity	NPC472860
0.5057	Remote Similarity	NPC484816
0.5055	Remote Similarity	NPC105591
0.5054	Remote Similarity	NPC488081

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC26385 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4454
0.1-0.2	4631
0.2-0.3	60
0.3-0.4	5
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