NPASS Compound

Natural Product: NPC133984

Natural Product ID	NPC133984
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Litseaefoloside C
IUPAC Name	[4-[(2S,3R,4S,5S,6R)-6-[[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxymethyl]-3,4,5-trihydroxyoxan-2-yl]oxy-3-hydroxyphenyl]methyl 4-hydroxy-3-methoxybenzoate
Synonyms	litseaefoloside C
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL506203
PubChem CID	11527348
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000238] Tannins [CHEMONTID:0001710] Hydrolyzable tannins

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 74 77 0 0 0 0 0 0 0 0999 V2000 -6.1611 -4.4164 -1.8517 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.4462 -4.0719 -1.3971 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.7860 -2.7441 -1.2530 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8781 -1.7542 -1.5535 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.1712 -0.4159 -1.4249 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.4299 -0.0927 -0.9764 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.3497 -1.0743 -0.6717 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.0463 -2.4322 -0.8041 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.9942 -3.3940 -0.4893 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.1974 0.6546 -1.7482 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0810 0.2444 -2.1659 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.5011 1.9654 -1.5999 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.6125 2.9942 -1.8913 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3749 2.8981 -1.0682 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1961 2.3610 -1.5260 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0580 2.2602 -0.7104 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0535 2.6916 0.5915 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2603 3.2391 1.0504 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3759 3.3386 0.2528 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2927 3.6865 2.3629 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9907 2.6312 1.4579 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2827 2.1302 1.1796 C 0 0 1 0 0 0 0 0 0 0 0 0 1.3768 3.1322 1.4459 C 0 0 1 0 0 0 0 0 0 0 0 0 2.2658 2.7564 2.6115 C 0 0 2 0 0 0 0 0 0 0 0 0 2.8308 1.3735 2.3716 C 0 0 1 0 0 0 0 0 0 0 0 0 1.8372 0.4921 1.6427 C 0 0 1 0 0 0 0 0 0 0 0 0 2.0282 -0.9730 1.9259 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3736 -1.3105 1.6921 O 0 0 0 0 0 0 0 0 0 0 0 0 3.9958 -1.2070 0.4913 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3936 -0.7978 -0.5173 O 0 0 0 0 0 0 0 0 0 0 0 0 5.4176 -1.5800 0.3455 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0390 -1.4900 -0.7971 C 0 0 0 0 0 0 0 0 0 0 0 0 7.4237 -1.8529 -0.9398 C 0 0 0 0 0 0 0 0 0 0 0 0 8.0185 -1.7393 -2.1871 C 0 0 0 0 0 0 0 0 0 0 0 0 9.3601 -2.0731 -2.3986 C 0 0 0 0 0 0 0 0 0 0 0 0 10.0916 -2.5228 -1.3330 C 0 0 0 0 0 0 0 0 0 0 0 0 9.5404 -2.6484 -0.0885 C 0 0 0 0 0 0 0 0 0 0 0 0 8.1933 -2.3039 0.0832 C 0 0 0 0 0 0 0 0 0 0 0 0 10.3216 -3.1081 0.9600 O 0 0 0 0 0 0 0 0 0 0 0 0 11.4294 -2.8655 -1.4973 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5274 0.9226 1.8532 O 0 0 0 0 0 0 0 0 0 0 0 0 4.0252 1.3876 1.6771 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5457 2.7937 3.7901 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1493 3.2532 0.2939 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.3702 -3.9077 -1.2608 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0835 -5.5330 -1.7446 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9714 -4.1897 -2.9093 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8688 -1.9885 -1.9142 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.6916 0.9658 -0.8634 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.3320 -0.8286 -0.3202 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.6795 -3.2248 0.2629 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1361 3.9644 -1.6389 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3190 3.0319 -2.9658 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1421 2.0210 -2.5493 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1592 1.8275 -1.1289 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3137 3.7655 0.6088 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8031 3.3006 3.1348 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3356 1.8571 0.1117 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9055 4.1067 1.6160 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1270 3.4557 2.6001 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9734 0.9147 3.3740 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0167 0.6529 0.5612 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3589 -1.5055 1.1854 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7267 -1.2258 2.9633 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9381 -1.9333 1.2162 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4493 -1.1225 -1.6440 H 0 0 0 0 0 0 0 0 0 0 0 0 7.4731 -1.3900 -3.0489 H 0 0 0 0 0 0 0 0 0 0 0 0 9.7850 -1.9709 -3.3800 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8298 -2.4271 1.0887 H 0 0 0 0 0 0 0 0 0 0 0 0 10.8504 -3.9671 0.8631 H 0 0 0 0 0 0 0 0 0 0 0 0 11.9962 -3.1846 -0.7423 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5180 2.2455 1.7756 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5986 1.9462 4.3056 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7775 4.0053 0.3255 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 2 0 6 7 1 0 7 8 2 0 8 9 1 0 5 10 1 0 10 11 2 0 10 12 1 0 12 13 1 0 13 14 1 0 14 15 2 0 15 16 1 0 16 17 2 0 17 18 1 0 18 19 2 0 18 20 1 0 17 21 1 0 21 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 26 27 1 0 27 28 1 0 28 29 1 0 29 30 2 0 29 31 1 0 31 32 2 0 32 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 26 41 1 0 25 42 1 0 24 43 1 0 23 44 1 0 8 3 1 0 19 14 1 0 41 22 1 0 38 33 1 0 1 45 1 0 1 46 1 0 1 47 1 0 4 48 1 0 6 49 1 0 7 50 1 0 9 51 1 0 13 52 1 0 13 53 1 0 15 54 1 0 16 55 1 0 19 56 1 0 20 57 1 0 22 58 1 6 23 59 1 1 24 60 1 1 25 61 1 1 26 62 1 6 27 63 1 0 27 64 1 0 31 65 1 0 32 66 1 0 34 67 1 0 35 68 1 0 38 69 1 0 39 70 1 0 40 71 1 0 42 72 1 0 43 73 1 0 44 74 1 0 M END

Standard InCHIKey	IMVLKRZWKQBCNJ-ZAHDVKFQSA-N
Standard InCHI	InChI=1S/C30H30O14/c1-40-23-12-17(5-7-19(23)32)29(39)42-13-16-3-8-22(21(34)11-16)43-30-28(38)27(37)26(36)24(44-30)14-41-25(35)9-4-15-2-6-18(31)20(33)10-15/h2-12,24,26-28,30-34,36-38H,13-14H2,1H3/b9-4+/t24-,26-,27+,28-,30-/m1/s1
SMILES	COc1cc(ccc1O)C(=O)OCc1ccc(c(c1)O)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](COC(=O)/C=C/c2ccc(c(c2)O)O)O1)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	614.16	Volume:	584.636 ? Van der Waals volume.
Dense:	1.051	LogP:	1.965 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.023 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.345 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	12.0	Rigid Bonds:	27.0
TPSA:	221.9 ? Topological Polar Surface Area.	H-Bond Acceptor:	14.0
H-Bond Donor:	7.0	Rings:	4.0
Heavy Atoms:	14.0

MedChem Properties

QED Drug-Likeness Score:	0.097	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.046	Fsp³:	0.267
MCE-18:	91.368 ? 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:	0.757	Fluc inhibitor:	0.989 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.326 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.86 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.117	Promiscuous compounds:	0.551

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.224	MDCK Permeability:	-5.43
Pgp-inhibitor:	0.002	Pgp-substrate:	0.0
PAMPA:	0.851 ? 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):	0.17
20% Bioavailability (F20%):	0.996	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.001	MRP1:	0.045
Plasma Protein Binding (PPB):	89.788%	Volume Distribution (VD):	-0.345
Fu:	7.94% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.001
BSEP inhibitor:	0.216

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:	0.33
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.351 ? 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):

4.252

Half-life (T1/2):

3.41

ADMET: Toxicity

hERG Blockers:	0.085	hERG Blockers (10um):	0.613
Human Hepatotoxicity (H-HT):	0.07	Drug-induced Liver Injury (DILI):	0.834
AMES Toxicity:	0.783	Rat Oral Acute Toxicity:	0.006
Maximum Recommended Daily Dose:	0.16	Skin Sensitization:	0.999
Carcinogencity:	0.238	Eye Corrosion:	0.0
Eye Irritation:	0.172	Respiratory Toxicity:	0.003
Drug-induced Neurotoxicity:	0.002	Ototoxicity:	0.898
Hematotoxicity:	0.005	Drug-induced Nephrotoxicity:	0.159
Genotoxicity:	0.244	RPMI-8226 Immunitoxicity:	0.094
A549 Cytotoxicity:	0.697	Hek293 Cytotoxicity:	0.616
BCF:	0.552 ? 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:	3.68 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.696 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.42 ? 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
NPO10814	Ilex latifolia	Species	Aquifoliaceae	Eukaryota	n.a.	stem	n.a.	PMID[16252920]
NPO33279	ilex litseaefolia	Species	Aquifoliaceae	Eukaryota	stems	n.a.	n.a.	PMID[16252920]
NPO10814	Ilex latifolia	Species	Aquifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10814	Ilex latifolia	Species	Aquifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO10814	Ilex latifolia	Species	Aquifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10814	Ilex latifolia	Species	Aquifoliaceae	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	1
Others	1

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT60	Individual protein	Lysosomal alpha-glucosidase	Homo sapiens	IC50	=	34.0	ug.mL-1	PMID[16252920]

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified	n.a.	IC50	=	0.31	ug.mL-1	PMID[16252920]

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 NPC133984 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	15286
0.1-0.2	29747
0.2-0.3	3865
0.3-0.4	753
0.4-0.5	165
0.5-0.6	30
0.6-0.7	9
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
0.7975	Intermediate Similarity	NPC194095
0.6905	Remote Similarity	NPC291296
0.6585	Remote Similarity	NPC191046
0.6444	Remote Similarity	NPC476865
0.6404	Remote Similarity	NPC476868
0.6364	Remote Similarity	NPC157816
0.6364	Remote Similarity	NPC476864
0.6129	Remote Similarity	NPC488081
0.6118	Remote Similarity	NPC157898
0.6044	Remote Similarity	NPC488082
0.5938	Remote Similarity	NPC476871
0.5934	Remote Similarity	NPC476866
0.5889	Remote Similarity	NPC471405
0.5761	Remote Similarity	NPC476869
0.5714	Remote Similarity	NPC476867
0.5684	Remote Similarity	NPC479767
0.5638	Remote Similarity	NPC476870
0.5604	Remote Similarity	NPC10205
0.5567	Remote Similarity	NPC11411
0.5484	Remote Similarity	NPC204937
0.5455	Remote Similarity	NPC291153
0.5283	Remote Similarity	NPC599948
0.5273	Remote Similarity	NPC484988
0.5253	Remote Similarity	NPC300262
0.5222	Remote Similarity	NPC311803
0.5204	Remote Similarity	NPC83743
0.5189	Remote Similarity	NPC603856
0.5182	Remote Similarity	NPC139571
0.5172	Remote Similarity	NPC470572
0.5169	Remote Similarity	NPC186406
0.5149	Remote Similarity	NPC125823
0.5149	Remote Similarity	NPC7145
0.5149	Remote Similarity	NPC143480
0.5104	Remote Similarity	NPC226005
0.5093	Remote Similarity	NPC470416
0.5056	Remote Similarity	NPC229784
0.5055	Remote Similarity	NPC327032
0.5047	Remote Similarity	NPC214621
0.5047	Remote Similarity	NPC34267
0.5046	Remote Similarity	NPC480796

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC133984 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4502
0.1-0.2	4553
0.2-0.3	90
0.3-0.4	4
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