NPASS Compound

Natural Product: NPC74766

Natural Product ID	NPC74766
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	BXFCPUCGPCDZKT-BEQMOXJMSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	101671063
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000123] Benzopyrans [CHEMONTID:0003410] 1-benzopyrans [CHEMONTID:0002817] Dibenzopyrans [CHEMONTID:0000200] Xanthenes [CHEMONTID:0000204] Xanthones [CHEMONTID:0003519] 8-prenylated xanthones

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 70 72 0 0 0 0 0 0 0 0999 V2000 6.1635 -1.8168 2.5874 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7677 -0.6198 1.7952 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4085 -0.6295 0.5322 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3519 -1.8594 -0.2755 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9995 -2.1752 -0.8497 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4357 -1.1684 -1.7496 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2497 -0.6111 -1.4270 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5723 0.4215 -2.2537 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2085 1.5504 -1.3573 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0731 1.4722 -0.5771 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1983 2.5456 0.2966 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6571 3.6302 0.3538 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7770 3.6668 -0.4434 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0803 2.6476 -1.3071 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1827 2.6332 -2.1260 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0602 3.1981 -3.4258 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6283 4.7859 -0.3639 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2729 2.5179 1.0605 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.0915 1.5188 1.0236 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2140 1.5047 1.8318 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1079 0.4279 1.8010 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9185 -0.6547 0.9774 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8515 -1.8202 0.9218 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0815 -1.5035 0.1619 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.3006 -1.6316 0.6635 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.4794 -2.1158 2.0536 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.5104 -1.2878 -0.1739 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.2949 -2.4367 -0.2882 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7808 -0.6322 0.1634 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9127 0.4301 0.2044 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7916 0.4122 -0.6212 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6016 -0.5645 -1.3813 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5722 -1.7115 -0.6729 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.2033 0.4742 2.6275 O 0 0 0 0 0 0 0 0 0 0 0 0 4.0580 -0.7091 -3.0064 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7763 0.7310 2.4918 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7606 -2.5056 1.9710 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3397 -2.2719 3.1521 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8857 -1.4390 3.3668 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1413 0.2952 0.0480 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1467 -1.8038 -1.0485 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6326 -2.7127 0.3703 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3205 -2.3155 0.0128 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0573 -3.2042 -1.3163 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7814 -0.9264 -0.5005 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7535 -0.0339 -2.8066 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3299 0.8208 -3.0262 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4406 4.4523 1.0316 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6331 4.1713 -3.4526 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4518 2.5715 -4.2261 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9877 3.4400 -3.6548 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4526 5.4816 0.3405 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3935 2.3479 2.4965 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3244 -2.6487 0.4037 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0850 -2.1410 1.9707 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9922 -1.1480 -0.8574 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1585 -1.4178 2.8244 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8703 -3.0584 2.1852 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.5364 -2.4652 2.2111 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.1392 -0.9564 -1.1535 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.0805 -0.4916 0.3201 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.7121 -2.4229 -1.1906 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9589 -1.7796 -1.6037 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2062 0.0637 3.5354 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9762 -1.2850 -3.2651 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4014 0.3318 -2.8695 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3487 -0.6991 -3.8702 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5254 0.5965 3.5664 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0318 1.3577 2.0054 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7920 1.1761 2.4456 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 2 3 3 4 1 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 2 0 12 13 1 0 13 14 2 0 14 15 1 0 15 16 1 0 13 17 1 0 11 18 1 0 18 19 1 0 19 20 2 0 20 21 1 0 21 22 2 0 22 23 1 0 23 24 1 0 24 25 2 0 25 26 1 0 25 27 1 0 27 28 1 0 22 29 1 0 29 30 2 0 30 31 1 0 31 32 2 0 29 33 1 0 21 34 1 0 6 35 1 0 2 36 1 0 14 9 1 0 30 19 1 0 31 10 1 0 1 37 1 0 1 38 1 0 1 39 1 0 3 40 1 0 4 41 1 0 4 42 1 0 5 43 1 0 5 44 1 0 7 45 1 0 8 46 1 0 8 47 1 0 12 48 1 0 16 49 1 0 16 50 1 0 16 51 1 0 17 52 1 0 20 53 1 0 23 54 1 0 23 55 1 0 24 56 1 0 26 57 1 0 26 58 1 0 26 59 1 0 27 60 1 0 27 61 1 0 28 62 1 0 33 63 1 0 34 64 1 0 35 65 1 0 35 66 1 0 35 67 1 0 36 68 1 0 36 69 1 0 36 70 1 0 M END

Standard InCHIKey	BXFCPUCGPCDZKT-BEQMOXJMSA-N
Standard InCHI	InChI=1S/C29H34O7/c1-16(2)7-6-8-17(3)9-12-20-25-23(14-22(32)29(20)35-5)36-24-13-21(31)19(11-10-18(4)15-30)27(33)26(24)28(25)34/h7,9-10,13-14,30-33H,6,8,11-12,15H2,1-5H3/b17-9+,18-10+
SMILES	CC(=CCC/C(=C/Cc1c2c(cc(c1OC)O)oc1cc(c(C/C=C(C)/CO)c(c1c2=O)O)O)/C)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	494.23	Volume:	519.638 ? Van der Waals volume.
Dense:	0.951	LogP:	5.979 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	4.072 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.997 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	9.0	Rigid Bonds:	20.0
TPSA:	120.36 ? Topological Polar Surface Area.	H-Bond Acceptor:	7.0
H-Bond Donor:	4.0	Rings:	3.0
Heavy Atoms:	7.0

MedChem Properties

QED Drug-Likeness Score:	0.22	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	3.436	Fsp³:	0.345
MCE-18:	23.0 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Rejected	GSK Rule:	Accepted
Golden Triangle Rule:	Rejected	BMS Rule:	0
Chelating Alert:	1	PAINS Alert:	0
Colloidal aggregators:	0.982	Fluc inhibitor:	0.39 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.964 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.797 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.232	Promiscuous compounds:	0.135

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.126	MDCK Permeability:	-4.738
Pgp-inhibitor:	1.0	Pgp-substrate:	0.032
PAMPA:	0.001 ? 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):	0.044
20% Bioavailability (F20%):	0.928	30% Bioavailability (F30%):	0.997
50% Bioavailability (F50%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.718
Plasma Protein Binding (PPB):	97.429%	Volume Distribution (VD):	0.094
Fu:	2.372% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.998	BCRP inhibitor:	0.988
BSEP inhibitor:	0.993

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.997
CYP2C19-inhibitor:	0.849	CYP2C19-substrate:	0.983
CYP2C9-inhibitor:	0.685	CYP2C9-substrate:	0.32
CYP2D6-inhibitor:	0.969	CYP2D6-substrate:	0.173
CYP3A4-inhibitor:	0.517	CYP3A4-substrate:	0.998
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.995 ? 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):

2.414

Half-life (T1/2):

1.385

ADMET: Toxicity

hERG Blockers:	0.043	hERG Blockers (10um):	0.608
Human Hepatotoxicity (H-HT):	0.813	Drug-induced Liver Injury (DILI):	0.947
AMES Toxicity:	0.125	Rat Oral Acute Toxicity:	0.723
Maximum Recommended Daily Dose:	0.705	Skin Sensitization:	0.986
Carcinogencity:	0.307	Eye Corrosion:	0.0
Eye Irritation:	0.577	Respiratory Toxicity:	0.994
Drug-induced Neurotoxicity:	0.094	Ototoxicity:	0.375
Hematotoxicity:	0.187	Drug-induced Nephrotoxicity:	0.238
Genotoxicity:	0.988	RPMI-8226 Immunitoxicity:	0.147
A549 Cytotoxicity:	0.458	Hek293 Cytotoxicity:	0.727
BCF:	2.223 ? 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:	5.27 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.793 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	6.322 ? 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
NPO25472	Garcinia cowa	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1071/CH03175]
NPO25472	Garcinia cowa	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19299148]
NPO25472	Garcinia cowa	Species	Clusiaceae	Eukaryota	twigs	n.a.	n.a.	PMID[20058933]
NPO25472	Garcinia cowa	Species	Clusiaceae	Eukaryota	young fruits	Khokkhon, Tha Bo District, Nong Khai Province, Thailand	2011-Aug	PMID[25651042]
NPO25472	Garcinia cowa	Species	Clusiaceae	Eukaryota	flowers	Pakook, Muang District, Chiang Rai Province, Thailand	2013-Feb	PMID[25651042]
NPO25472	Garcinia cowa	Species	Clusiaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[31860303]
NPO25472	Garcinia cowa	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25472	Garcinia cowa	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25472	Garcinia cowa	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25472	Garcinia cowa	Species	Clusiaceae	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	3

Activity Type	# Activity
Individual protein	1
Cell line	1
Protein family	1

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT156	Individual protein	Sphingomyelin phosphodiesterase	Homo sapiens	IC50	=	10900.0	nM	PMID[33395289]

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell line	RAW264.7	Mus musculus	IC50	=	13400.0	nM	PMID[31860303]
NPT20648	Protein family	Alpha glucosidase	Homo sapiens	IC50	=	28700.0	nM	PMID[31860303]

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 NPC74766 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	16480
0.1-0.2	29722
0.2-0.3	3257
0.3-0.4	310
0.4-0.5	45
0.5-0.6	26
0.6-0.7	8
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC7483
0.9	High Similarity	NPC40491
0.9	High Similarity	NPC278052
0.7571	Intermediate Similarity	NPC228785
0.7013	Intermediate Similarity	NPC300727
0.7	Intermediate Similarity	NPC479155
0.6883	Remote Similarity	NPC310349
0.6883	Remote Similarity	NPC61010
0.6795	Remote Similarity	NPC262286
0.6753	Remote Similarity	NPC236796
0.6471	Remote Similarity	NPC39091
0.6463	Remote Similarity	NPC206153
0.6463	Remote Similarity	NPC271629
0.6329	Remote Similarity	NPC25152
0.5974	Remote Similarity	NPC602307
0.5909	Remote Similarity	NPC479158
0.5854	Remote Similarity	NPC320359
0.5833	Remote Similarity	NPC476242
0.5769	Remote Similarity	NPC14353
0.575	Remote Similarity	NPC236132
0.575	Remote Similarity	NPC68093
0.5641	Remote Similarity	NPC241904
0.5542	Remote Similarity	NPC227337
0.5476	Remote Similarity	NPC189473
0.5455	Remote Similarity	NPC142339
0.5443	Remote Similarity	NPC488548
0.5432	Remote Similarity	NPC217677
0.5412	Remote Similarity	NPC236521
0.5402	Remote Similarity	NPC133392
0.5393	Remote Similarity	NPC488441
0.5385	Remote Similarity	NPC479159
0.5349	Remote Similarity	NPC117854
0.5349	Remote Similarity	NPC170245
0.5269	Remote Similarity	NPC150977
0.5244	Remote Similarity	NPC479160
0.5233	Remote Similarity	NPC275780
0.5119	Remote Similarity	NPC220313
0.5116	Remote Similarity	NPC248638
0.5114	Remote Similarity	NPC479164
0.5057	Remote Similarity	NPC152659

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC74766 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3674
0.1-0.2	5432
0.2-0.3	43
0.3-0.4	1
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