NPASS Compound

Natural Product: NPC472809

Natural Product ID	NPC472809
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	(12R,16Eta)-12,16-Dihydroxylabda-8(17),13-Dien-15-16-Olide
IUPAC Name	3-[(1R)-2-[(1S,4aS,8aS)-5,5,8a-trimethyl-2-methylidene-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]-1-hydroxyethyl]-2-hydroxy-2H-furan-5-one
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL3586262
PubChem CID	24741284
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones [CHEMONTID:0001538] Diterpene lactones

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 54 56 0 0 0 0 0 0 0 0999 V2000 6.9046 1.9481 -1.3361 O 0 0 0 0 0 0 0 0 0 0 0 0 5.9483 1.1604 -1.1269 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8665 1.2700 -0.1550 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0565 0.2450 -0.2406 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5788 -0.6299 -1.3135 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7376 -0.0104 -1.8131 O 0 0 0 0 0 0 0 0 0 0 0 0 4.8933 -1.8692 -0.7345 O 0 0 0 0 0 0 0 0 0 0 0 0 2.8429 -0.0321 0.5557 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6028 -0.1324 -0.3431 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4474 -0.4147 0.5879 C 0 0 1 0 0 0 0 0 0 0 0 0 0.3400 0.7049 1.5518 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6110 0.5955 2.8424 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1079 2.0320 0.9903 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1961 1.7673 -0.0522 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8096 0.4249 0.2777 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8514 -0.6767 -0.1502 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.6797 -0.7389 -1.6354 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4193 -1.9564 0.4221 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8360 -2.2104 0.1294 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6061 -1.1404 -0.5280 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2002 0.2584 -0.2052 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1275 0.8144 0.8899 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4728 1.1068 -1.4482 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9857 -1.2308 1.2922 O 0 0 0 0 0 0 0 0 0 0 0 0 4.8108 2.1330 0.5246 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8174 -0.8060 -2.1134 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2686 -2.5794 -1.0659 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7369 0.7643 1.3081 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5375 0.8146 -0.8708 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7616 -1.0234 -0.9643 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7716 -1.3110 1.1963 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9290 -0.3428 3.2466 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5144 1.4378 3.4840 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7581 2.5576 0.5257 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4851 2.6915 1.7997 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6702 1.7392 -1.0264 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9414 2.5678 0.0348 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8120 0.3665 1.4070 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5872 -1.8280 -1.9207 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2136 -0.2227 -2.0197 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5379 -0.3618 -2.2125 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2252 -1.9163 1.5195 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7424 -2.7796 0.0488 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3515 -2.5270 1.0843 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9022 -3.1350 -0.5178 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6877 -1.2572 -0.2152 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6545 -1.3315 -1.6418 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4197 0.0354 1.5965 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0032 1.3322 0.4146 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5751 1.6160 1.4335 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3077 1.8207 -1.2955 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5894 1.7360 -1.7113 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7841 0.4736 -2.3161 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6481 -1.9500 0.6982 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 1 0 5 7 1 0 4 8 1 0 8 9 1 0 9 10 1 0 10 11 1 0 11 12 2 0 11 13 1 0 13 14 1 0 14 15 1 0 15 16 1 0 16 17 1 6 16 18 1 0 18 19 1 0 19 20 1 0 20 21 1 0 21 22 1 0 21 23 1 0 8 24 1 0 6 2 1 0 16 10 1 0 21 15 1 0 3 25 1 0 5 26 1 0 7 27 1 0 8 28 1 1 9 29 1 0 9 30 1 0 10 31 1 1 12 32 1 0 12 33 1 0 13 34 1 0 13 35 1 0 14 36 1 0 14 37 1 0 15 38 1 1 17 39 1 0 17 40 1 0 17 41 1 0 18 42 1 0 18 43 1 0 19 44 1 0 19 45 1 0 20 46 1 0 20 47 1 0 22 48 1 0 22 49 1 0 22 50 1 0 23 51 1 0 23 52 1 0 23 53 1 0 24 54 1 0 M END

Standard InCHIKey	HYOANESYDNMXHG-UTVKXTEFSA-N
Standard InCHI	InChI=1S/C20H30O4/c1-12-6-7-16-19(2,3)8-5-9-20(16,4)14(12)11-15(21)13-10-17(22)24-18(13)23/h10,14-16,18,21,23H,1,5-9,11H2,2-4H3/t14-,15+,16-,18?,20+/m0/s1
SMILES	O=C1C=C(C(O1)O)[C@@H](C[C@H]1C(=C)CC[C@@H]2[C@]1(C)CCCC2(C)C)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	334.21	Volume:	356.058 ? Van der Waals volume.
Dense:	0.939	LogP:	3.17 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.407 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.496 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	3.0	Rigid Bonds:	18.0
TPSA:	66.76 ? Topological Polar Surface Area.	H-Bond Acceptor:	4.0
H-Bond Donor:	2.0	Rings:	3.0
Heavy Atoms:	4.0

MedChem Properties

QED Drug-Likeness Score:	0.614	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.596	Fsp³:	0.75
MCE-18:	56.571 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted	GSK Rule:	Rejected
Golden Triangle Rule:	Rejected	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.566	Fluc inhibitor:	0.004 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.013 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.001 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.29	Promiscuous compounds:	0.12

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.615	MDCK Permeability:	-4.739
Pgp-inhibitor:	0.164	Pgp-substrate:	0.067
PAMPA:	0.475 ? 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%):	0.092	30% Bioavailability (F30%):	0.573
50% Bioavailability (F50%):	0.988

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.013	MRP1:	0.105
Plasma Protein Binding (PPB):	98.341%	Volume Distribution (VD):	0.092
Fu:	1.764% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.997	BCRP inhibitor:	0.866
BSEP inhibitor:	0.961

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.058
CYP2C19-inhibitor:	0.017	CYP2C19-substrate:	0.019
CYP2C9-inhibitor:	0.206	CYP2C9-substrate:	0.023
CYP2D6-inhibitor:	0.885	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.002	CYP3A4-substrate:	0.005
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.051
HLM stability:	0.82 ? 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):

7.061

Half-life (T1/2):

1.501

ADMET: Toxicity

hERG Blockers:	0.05	hERG Blockers (10um):	0.51
Human Hepatotoxicity (H-HT):	0.632	Drug-induced Liver Injury (DILI):	0.591
AMES Toxicity:	0.534	Rat Oral Acute Toxicity:	0.687
Maximum Recommended Daily Dose:	0.922	Skin Sensitization:	0.959
Carcinogencity:	0.904	Eye Corrosion:	0.015
Eye Irritation:	0.648	Respiratory Toxicity:	0.762
Drug-induced Neurotoxicity:	0.502	Ototoxicity:	0.539
Hematotoxicity:	0.271	Drug-induced Nephrotoxicity:	0.898
Genotoxicity:	0.68	RPMI-8226 Immunitoxicity:	0.118
A549 Cytotoxicity:	0.136	Hek293 Cytotoxicity:	0.422
BCF:	1.878 ? 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:	4.594 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.435 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.814 ? 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
NPO32474	vitex vestita	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26034885]

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
MIC	43
GI	4

Activity Type	# Activity
Cell line	4
Organism	43

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
NPT171	Cell line	MRC5	Homo sapiens	GI	=	95.0	%	PubChem BioAssay data set
NPT171	Cell line	MRC5	Homo sapiens	GI	=	22.0	%	PMID[23691952]
NPT393	Cell line	HCT-116	Homo sapiens	GI	=	87.0	%	PMID[24370114]
NPT393	Cell line	HCT-116	Homo sapiens	GI	=	0.0	%	PMID[17190448]
NPT4845	Organism	Listeria innocua	Listeria innocua	MIC	=	48000.0	nM	PMID[22834923]
NPT4075	Organism	Enterococcus avium	Enterococcus avium	MIC	=	48000.0	nM	PMID[22197393]
NPT4844	Organism	Enterococcus gallinarum	Enterococcus gallinarum	MIC	=	96000.0	nM	DOI[10.6019/CHEMBL1201861]
NPT4844	Organism	Enterococcus gallinarum	Enterococcus gallinarum	MIC	=	24000.0	nM	PMID[19459645]
NPT4844	Organism	Enterococcus gallinarum	Enterococcus gallinarum	MIC	=	48000.0	nM	PMID[23252848]
NPT564	Organism	Listeria monocytogenes	Listeria monocytogenes	MIC	=	24000.0	nM	PMID[20112995]
NPT564	Organism	Listeria monocytogenes	Listeria monocytogenes	MIC	=	48000.0	nM	PMID[19296617]
NPT4839	Organism	Staphylococcus intermedius	Staphylococcus intermedius	MIC	=	12000.0	nM	PMID[15026054]
NPT4840	Organism	Staphylococcus lugdunensis	Staphylococcus lugdunensis	MIC	=	24000.0	nM	PMID[12639569]
NPT4428	Organism	Staphylococcus sciuri	Staphylococcus sciuri	MIC	=	48000.0	nM	PubChem BioAssay data set
NPT3145	Organism	Bacillus subtilis subsp. spizizenii ATCC 6633	Bacillus subtilis subsp. spizizenii ATCC 6633	MIC	=	6000.0	nM	PMID[12166949]
NPT3730	Organism	Enterococcus durans	Enterococcus durans	MIC	=	24000.0	nM	PMID[11421731]
NPT175	Organism	Enterococcus faecalis	Enterococcus faecalis	MIC	=	96000.0	nM	PMID[25871261]
NPT175	Organism	Enterococcus faecalis	Enterococcus faecalis	MIC	=	24000.0	nM	PMID[16989516]
NPT175	Organism	Enterococcus faecalis	Enterococcus faecalis	MIC	=	48000.0	nM	PMID[20039643]
NPT3721	Organism	Enterococcus hirae	Enterococcus hirae	MIC	=	96000.0	nM	PMID[12932125]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	24000.0	nM	Open TG-GATES in vivo data: Biochemistry
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	12000.0	nM	PMID[19258280]
NPT17	Organism	Staphylococcus epidermidis	Staphylococcus epidermidis	MIC	=	12000.0	nM	PMID[15267244]
NPT1863	Organism	Staphylococcus saprophyticus	Staphylococcus saprophyticus	MIC	=	24000.0	nM	PMID[18591275]
NPT314	Organism	Bacillus cereus	Bacillus cereus	MIC	=	6000.0	nM	PMID[24491225]
NPT314	Organism	Bacillus cereus	Bacillus cereus	MIC	=	12000.0	nM	PMID[23398362]
NPT4843	Organism	Corynebacterium striatum	Corynebacterium striatum	MIC	=	24000.0	nM	PMID[24697496]
NPT1531	Organism	Enterococcus faecium	Enterococcus faecium	MIC	=	96000.0	nM	PMID[9322367]
NPT1531	Organism	Enterococcus faecium	Enterococcus faecium	MIC	=	48000.0	nM	PMID[18183025]
NPT1477	Organism	Staphylococcus haemolyticus	Staphylococcus haemolyticus	MIC	=	6000.0	nM	PMID[20439614]

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 NPC472809 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	15069
0.1-0.2	28033
0.2-0.3	6066
0.3-0.4	548
0.4-0.5	108
0.5-0.6	18
0.6-0.7	9
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC472810
0.94	High Similarity	NPC489288
0.7091	Intermediate Similarity	NPC311070
0.7091	Intermediate Similarity	NPC475709
0.6909	Remote Similarity	NPC472812
0.6491	Remote Similarity	NPC177037
0.6491	Remote Similarity	NPC472814
0.625	Remote Similarity	NPC478392
0.625	Remote Similarity	NPC251528
0.6111	Remote Similarity	NPC484730
0.6111	Remote Similarity	NPC185587
0.6111	Remote Similarity	NPC484729
0.6	Remote Similarity	NPC35655
0.5932	Remote Similarity	NPC489285
0.5862	Remote Similarity	NPC217394
0.5763	Remote Similarity	NPC79027
0.5517	Remote Similarity	NPC99321
0.55	Remote Similarity	NPC472811
0.5439	Remote Similarity	NPC484731
0.5439	Remote Similarity	NPC189745
0.5439	Remote Similarity	NPC175334
0.5424	Remote Similarity	NPC12170
0.5397	Remote Similarity	NPC489287
0.5345	Remote Similarity	NPC478390
0.5333	Remote Similarity	NPC470255
0.5273	Remote Similarity	NPC226997
0.5179	Remote Similarity	NPC68703
0.5167	Remote Similarity	NPC144947
0.5147	Remote Similarity	NPC324078
0.5091	Remote Similarity	NPC41160
0.5091	Remote Similarity	NPC67840

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC472809 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6156
0.1-0.2	2837
0.2-0.3	145
0.3-0.4	9
0.4-0.5	3
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