NPASS Compound

Natural Product: NPC66344

Natural Product ID	NPC66344
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Sinocalycanchinensin B
IUPAC Name	n.a.
Synonyms	Sinocalycanchinensin B
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL1774186
PubChem CID	54584285
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001550] Sesquiterpenoids

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 80 83 0 0 0 0 0 0 0 0999 V2000 -5.4422 0.1002 -2.6369 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2768 0.2256 -2.0159 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1676 0.5535 -0.5698 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.6288 1.9694 -0.5123 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3639 1.8826 0.3294 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4993 0.8276 -0.3906 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0882 1.1621 0.0005 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0410 1.8512 1.3322 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5847 2.0903 -0.9843 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9764 2.0672 -0.3926 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1646 0.6497 0.1795 C 0 0 2 0 0 0 0 0 0 0 0 0 3.3560 0.1016 -0.6258 C 0 0 2 0 0 0 0 0 0 0 0 0 3.5893 -1.2965 -0.0784 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5950 0.8990 -0.3029 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8285 0.5151 -1.0732 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3122 -0.8474 -0.9458 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3786 -1.2762 -0.3467 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6657 -2.7670 -0.3600 C 0 0 0 0 0 0 0 0 0 0 0 0 8.2714 -0.3929 0.3510 C 0 0 0 0 0 0 0 0 0 0 0 0 9.3024 -0.9315 0.8975 O 0 0 0 0 0 0 0 0 0 0 0 0 8.1824 0.9572 0.5226 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8717 -0.0211 -0.0564 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8311 -0.7172 -1.3894 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3666 -0.9764 0.9633 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0964 -0.9624 1.2752 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9620 -0.4870 0.1274 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.7945 -1.4747 -0.5484 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4419 -0.4259 0.2794 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.0582 -0.9425 1.5516 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3125 -1.7084 1.4771 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5014 -1.1012 0.9194 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 -1.4936 -0.2070 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.2410 -0.0933 1.5287 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.4001 0.4389 0.8940 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4489 -0.1401 -3.6864 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4104 0.2340 -2.1709 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3867 0.0796 -2.6562 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2200 0.6045 -0.1927 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3234 2.6084 0.0673 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4221 2.4082 -1.4946 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7337 1.4905 1.3086 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8619 2.8448 0.3935 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5575 0.9670 -1.4812 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7962 1.3884 1.9971 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8763 1.9245 1.9246 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3702 2.9313 1.2422 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1551 3.1144 -0.9069 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5576 1.7317 -2.0152 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6437 2.2809 -1.2450 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1773 2.8334 0.3522 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5310 0.6722 1.2246 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2228 0.1627 -1.6995 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8217 -1.5830 0.7023 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5046 -2.0883 -0.8357 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5210 -1.3597 0.5545 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4744 2.0039 -0.5239 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7840 0.8894 0.8015 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6643 1.2174 -0.9223 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6073 0.7339 -2.2056 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7061 -1.6332 -1.4454 H 0 0 0 0 0 0 0 0 0 0 0 0 8.2398 -3.0351 0.5429 H 0 0 0 0 0 0 0 0 0 0 0 0 8.1688 -3.0604 -1.2955 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6948 -3.2988 -0.3276 H 0 0 0 0 0 0 0 0 0 0 0 0 8.4196 1.3608 1.4217 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2354 -0.8816 -1.7341 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3064 -0.1933 -2.2122 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1741 -1.7618 -1.2321 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5704 -2.0343 0.6090 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9437 -0.8291 1.9066 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3813 -0.3792 2.1713 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4344 -2.0086 1.5174 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8113 -1.5023 -1.6443 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7250 -2.5263 -0.1350 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3009 -1.6208 2.0580 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2406 -0.0739 2.2664 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5696 -2.0100 2.5351 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1444 -2.7046 0.9739 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.3355 0.1179 1.3827 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.3707 1.5460 0.9702 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.3794 0.2025 -0.1930 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 2 3 1 0 3 4 1 0 4 5 1 0 5 6 1 0 6 7 1 0 7 8 1 1 7 9 1 0 9 10 1 0 10 11 1 0 11 12 1 0 12 13 1 0 12 14 1 0 14 15 1 0 15 16 1 0 16 17 2 0 17 18 1 0 17 19 1 0 19 20 2 0 19 21 1 0 11 22 1 0 22 23 1 6 22 24 1 0 24 25 1 0 26 25 1 1 26 27 1 0 27 28 1 0 28 29 1 1 29 30 1 0 30 31 1 0 31 32 2 0 31 33 1 0 33 34 1 0 28 3 1 0 26 6 1 0 22 7 1 0 28 26 1 0 1 35 1 0 1 36 1 0 2 37 1 0 3 38 1 1 4 39 1 0 4 40 1 0 5 41 1 0 5 42 1 0 6 43 1 6 8 44 1 0 8 45 1 0 8 46 1 0 9 47 1 0 9 48 1 0 10 49 1 0 10 50 1 0 11 51 1 1 12 52 1 6 13 53 1 0 13 54 1 0 13 55 1 0 14 56 1 0 14 57 1 0 15 58 1 0 15 59 1 0 16 60 1 0 18 61 1 0 18 62 1 0 18 63 1 0 21 64 1 0 23 65 1 0 23 66 1 0 23 67 1 0 24 68 1 0 24 69 1 0 25 70 1 0 25 71 1 0 27 72 1 0 27 73 1 0 29 74 1 0 29 75 1 0 30 76 1 0 30 77 1 0 34 78 1 0 34 79 1 0 34 80 1 0 M END

Standard InCHIKey	JDMVZCVPHOWJJQ-RKLLWIJMSA-N
Standard InCHI	InChI=1S/C30H46O4/c1-7-22-11-12-24-28(5)15-13-23(20(2)9-8-10-21(3)26(32)33)27(28,4)17-18-30(24)19-29(22,30)16-14-25(31)34-6/h7,10,20,22-24H,1,8-9,11-19H2,2-6H3,(H,32,33)/b21-10-/t20-,22-,23-,24+,27-,28+,29-,30+/m1/s1
SMILES	C=C[C@@H]1CC[C@H]2[C@]3(C)CC[C@H]([C@H](C)CC/C=C(/C)C(=O)O)[C@@]3(C)CC[C@@]32C[C@]13CCC(=O)OC

Calculated Properties

Physi-Chem Properties

Molecular Weight:	470.34	Volume:	517.825 ? Van der Waals volume.
Dense:	0.908	LogP:	5.244 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.886 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.724 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	10.0	Rigid Bonds:	21.0
TPSA:	63.6 ? Topological Polar Surface Area.	H-Bond Acceptor:	4.0
H-Bond Donor:	1.0	Rings:	4.0
Heavy Atoms:	4.0

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:	5.316	Fsp³:	0.8
MCE-18:	109.074 ? 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:	Accepted
Golden Triangle Rule:	Rejected	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.756	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.006 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.002 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.647	Promiscuous compounds:	0.15

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.273	MDCK Permeability:	-4.957
Pgp-inhibitor:	0.233	Pgp-substrate:	0.006
PAMPA:	0.025 ? 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%):	0.985	30% Bioavailability (F30%):	0.957
50% Bioavailability (F50%):	0.92

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.018	MRP1:	0.998
Plasma Protein Binding (PPB):	95.941%	Volume Distribution (VD):	-0.468
Fu:	4.446% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.821
OATP1B3 inhibitor:	0.053	BCRP inhibitor:	0.129
BSEP inhibitor:	0.994

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.007
CYP2C19-inhibitor:	0.002	CYP2C19-substrate:	0.094
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.007
CYP3A4-inhibitor:	1.0	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.99
HLM stability:	0.003 ? 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):

2.687

Half-life (T1/2):

0.859

ADMET: Toxicity

hERG Blockers:	0.057	hERG Blockers (10um):	0.091
Human Hepatotoxicity (H-HT):	0.556	Drug-induced Liver Injury (DILI):	0.323
AMES Toxicity:	0.1	Rat Oral Acute Toxicity:	0.271
Maximum Recommended Daily Dose:	0.307	Skin Sensitization:	0.888
Carcinogencity:	0.436	Eye Corrosion:	0.274
Eye Irritation:	0.582	Respiratory Toxicity:	0.864
Drug-induced Neurotoxicity:	0.191	Ototoxicity:	0.707
Hematotoxicity:	0.726	Drug-induced Nephrotoxicity:	0.791
Genotoxicity:	0.322	RPMI-8226 Immunitoxicity:	0.036
A549 Cytotoxicity:	0.008	Hek293 Cytotoxicity:	0.042
BCF:	1.286 ? 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:	4.226 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.641 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.994 ? 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
NPO33379	sinocalycanthus chinensis	Species	n.a.	n.a.	leaves	n.a.	n.a.	PMID[21493075]
NPO33379	sinocalycanthus chinensis	Species	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]

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	6

Activity Type	# Activity
Cell line	4
Non-molecular	2

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
NPT91	Cell line	KB	Homo sapiens	IC50	=	20.9	ug.mL-1	PMID[10785421]
NPT83	Cell line	MCF7	Homo sapiens	IC50	=	35.7	ug.mL-1	PMID[24164206]
NPT111	Cell line	K562	Homo sapiens	IC50	=	17.6	ug.mL-1	PMID[19943620]
NPT111	Cell line	K562	Homo sapiens	IC50	=	16.5	ug.mL-1	PMID[18052327]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	IC50	=	22.2	ug.mL-1	PMID[21493075]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	IC50	=	18.9	ug.mL-1	PMID[21493075]

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 NPC66344 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	22034
0.1-0.2	24627
0.2-0.3	2809
0.3-0.4	248
0.4-0.5	105
0.5-0.6	20
0.6-0.7	10
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
0.7377	Intermediate Similarity	NPC236618
0.7067	Intermediate Similarity	NPC293052
0.6667	Remote Similarity	NPC110923
0.6667	Remote Similarity	NPC74296
0.6615	Remote Similarity	NPC181743
0.6615	Remote Similarity	NPC186975
0.6615	Remote Similarity	NPC178025
0.6571	Remote Similarity	NPC470113
0.6562	Remote Similarity	NPC16287
0.6418	Remote Similarity	NPC29152
0.6286	Remote Similarity	NPC81256
0.6029	Remote Similarity	NPC117122
0.5797	Remote Similarity	NPC283733
0.5735	Remote Similarity	NPC195366
0.5735	Remote Similarity	NPC114743
0.5634	Remote Similarity	NPC156546
0.5556	Remote Similarity	NPC476187
0.5507	Remote Similarity	NPC33473
0.5493	Remote Similarity	NPC23217
0.5286	Remote Similarity	NPC85379
0.5286	Remote Similarity	NPC144909
0.5286	Remote Similarity	NPC479654
0.5286	Remote Similarity	NPC476304
0.5286	Remote Similarity	NPC479656
0.527	Remote Similarity	NPC327788
0.5217	Remote Similarity	NPC158846
0.5217	Remote Similarity	NPC476186
0.5195	Remote Similarity	NPC486360
0.5135	Remote Similarity	NPC479657
0.5135	Remote Similarity	NPC307164
0.5068	Remote Similarity	NPC482630
0.5068	Remote Similarity	NPC479653

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC66344 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6241
0.1-0.2	2822
0.2-0.3	82
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