NPASS Compound

Natural Product: NPC487915

Natural Product ID	NPC487915
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	SGBKFQBILVXVCY-BCUNMAEHSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	23427264
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002341] Phenol ethers

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 84 0 0 0 0 0 0 0 0999 V2000 -13.7883 1.7964 -1.3274 C 0 0 0 0 0 0 0 0 0 0 0 0 -13.5026 0.5961 -0.6601 O 0 0 0 0 0 0 0 0 0 0 0 0 -12.2051 0.2988 -0.2614 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.7168 0.8839 0.7986 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.3788 0.6512 1.3060 C 0 0 1 0 0 0 0 0 0 0 0 0 -9.5627 -0.3045 0.5554 C 0 0 1 0 0 0 0 0 0 0 0 0 -10.1775 -0.9060 -0.6040 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.3899 -0.6532 -1.0099 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.1222 -1.4993 -2.5587 Br 0 0 0 0 0 0 0 0 0 0 0 0 -8.2390 0.3563 0.0809 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.3556 -0.8368 0.0133 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.8200 -1.7444 0.7903 N 0 0 0 0 0 0 0 0 0 0 0 0 -8.9692 -1.3015 1.4147 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.1569 -0.8870 -0.8348 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8086 0.0804 -1.5548 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.3949 -2.0848 -0.8116 N 0 0 0 0 0 0 0 0 0 0 0 0 -4.2054 -2.2231 -1.5906 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1318 -1.2903 -1.1426 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2165 -1.1690 -1.9599 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.1873 -0.6124 0.1408 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2940 0.3992 0.4372 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9434 0.3177 0.4117 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1799 0.8133 -0.6164 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2168 0.6863 -0.5944 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8546 0.0704 0.4495 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0815 -0.4179 1.4724 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2877 -0.3147 1.4875 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3377 -0.9940 2.9349 Br 0 0 0 0 0 0 0 0 0 0 0 0 3.3421 -0.0229 0.4113 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8618 1.2623 0.9555 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2808 1.3590 1.1348 N 0 0 0 0 0 0 0 0 0 0 0 0 6.2509 1.2711 0.1122 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8664 1.0964 -1.0688 O 0 0 0 0 0 0 0 0 0 0 0 0 7.7019 1.3824 0.4182 C 0 0 0 0 0 0 0 0 0 0 0 0 8.2056 1.5578 1.5851 N 0 0 0 0 0 0 0 0 0 0 0 0 9.5941 1.6181 1.5248 O 0 0 0 0 0 0 0 0 0 0 0 0 9.9699 0.8588 0.3600 C 0 0 2 0 0 0 0 0 0 0 0 0 9.7854 -0.5550 0.5798 C 0 0 0 0 0 0 0 0 0 0 0 0 10.6912 -1.4630 0.3524 C 0 0 0 0 0 0 0 0 0 0 0 0 12.0008 -1.0387 -0.1638 C 0 0 0 0 0 0 0 0 0 0 0 0 12.2465 0.2377 -0.3889 C 0 0 0 0 0 0 0 0 0 0 0 0 11.2783 1.2932 -0.1535 C 0 0 1 0 0 0 0 0 0 0 0 0 11.1418 2.1504 -1.2590 O 0 0 0 0 0 0 0 0 0 0 0 0 13.9753 0.6969 -1.0610 Br 0 0 0 0 0 0 0 0 0 0 0 0 12.9702 -1.9971 -0.4096 O 0 0 0 0 0 0 0 0 0 0 0 0 12.9396 -2.8342 -1.5523 C 0 0 0 0 0 0 0 0 0 0 0 0 10.3604 -3.3321 0.6733 Br 0 0 0 0 0 0 0 0 0 0 0 0 8.8148 1.3251 -0.5529 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8010 -0.3896 -0.8316 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0137 1.7954 -2.0345 Br 0 0 0 0 0 0 0 0 0 0 0 0 -9.6768 1.8738 1.4909 O 0 0 0 0 0 0 0 0 0 0 0 0 -12.8202 2.1398 1.7649 Br 0 0 0 0 0 0 0 0 0 0 0 0 -14.8896 1.8130 -1.5336 H 0 0 0 0 0 0 0 0 0 0 0 0 -13.2019 1.8525 -2.2678 H 0 0 0 0 0 0 0 0 0 0 0 0 -13.5784 2.7007 -0.7458 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.5171 0.2128 2.3580 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.6258 -1.6458 -1.2354 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.9014 1.1067 0.8169 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.4359 0.7716 -0.9315 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6992 -2.8933 -0.2142 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4522 -1.9771 -2.6486 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8440 -3.2739 -1.5937 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2291 -0.3651 0.4975 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9237 -1.4397 0.9263 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7338 1.1033 -1.4476 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5542 -0.9185 2.3306 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6217 -0.8524 1.1296 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4815 2.1510 0.3949 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3832 1.3762 1.9769 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6853 1.5105 2.1100 H 0 0 0 0 0 0 0 0 0 0 0 0 8.8243 -0.9492 0.9685 H 0 0 0 0 0 0 0 0 0 0 0 0 11.7312 1.9644 0.6429 H 0 0 0 0 0 0 0 0 0 0 0 0 10.9258 3.0449 -0.9120 H 0 0 0 0 0 0 0 0 0 0 0 0 13.8031 -3.5138 -1.5937 H 0 0 0 0 0 0 0 0 0 0 0 0 12.9693 -2.2066 -2.4631 H 0 0 0 0 0 0 0 0 0 0 0 0 11.9631 -3.3950 -1.5960 H 0 0 0 0 0 0 0 0 0 0 0 0 9.0254 2.3404 -0.9496 H 0 0 0 0 0 0 0 0 0 0 0 0 8.6374 0.5823 -1.3539 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6630 -1.3704 -0.9278 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.0533 2.2737 2.3037 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 1 0 6 7 1 0 7 8 2 0 8 9 1 0 6 10 1 0 10 11 1 0 11 12 2 0 12 13 1 0 11 14 1 0 14 15 2 0 14 16 1 0 16 17 1 0 17 18 1 0 18 19 2 0 18 20 1 0 20 21 1 0 21 22 1 0 22 23 2 0 23 24 1 0 24 25 2 0 25 26 1 0 26 27 2 0 27 28 1 0 25 29 1 0 29 30 1 0 30 31 1 0 31 32 1 0 32 33 2 0 32 34 1 0 34 35 2 0 35 36 1 0 37 36 1 1 37 38 1 0 38 39 2 0 39 40 1 0 40 41 2 0 41 42 1 0 42 43 1 0 41 44 1 0 40 45 1 0 45 46 1 0 39 47 1 0 37 48 1 0 29 49 1 0 23 50 1 0 5 51 1 0 4 52 1 0 8 3 1 0 27 22 1 0 48 34 1 0 6 13 1 1 42 37 1 0 1 53 1 0 1 54 1 0 1 55 1 0 5 56 1 1 7 57 1 0 10 58 1 0 10 59 1 0 16 60 1 0 17 61 1 0 17 62 1 0 20 63 1 0 20 64 1 0 24 65 1 0 26 66 1 0 29 67 1 0 30 68 1 0 30 69 1 0 31 70 1 0 38 71 1 0 42 72 1 1 43 73 1 0 46 74 1 0 46 75 1 0 46 76 1 0 48 77 1 0 48 78 1 0 49 79 1 0 51 80 1 0 M END

Standard InCHIKey	SGBKFQBILVXVCY-BCUNMAEHSA-N
Standard InCHI	InChI=1S/C31H28Br6N4O11/c1-48-24-16(34)5-30(26(44)21(24)36)7-18(40-51-30)28(46)38-9-13(42)11-50-23-14(32)3-12(4-15(23)33)20(43)10-39-29(47)19-8-31(52-41-19)6-17(35)25(49-2)22(37)27(31)45/h3-6,20,26-27,43-45H,7-11H2,1-2H3,(H,38,46)(H,39,47)/t20?,26-,27+,30+,31-/m0/s1
SMILES	COC1=C([C@@H]([C@@]2(C=C1Br)CC(=NO2)C(=O)NCC(=O)COc1c(cc(cc1Br)C(CNC(=O)C1=NO[C@@]2(C=C(C(=C([C@H]2O)Br)OC)Br)C1)O)Br)O)Br

Calculated Properties

Physi-Chem Properties

Molecular Weight:	1105.69	Volume:	726.693 ? Van der Waals volume.
Dense:	1.522	LogP:	2.887 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.661 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.712 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	14.0	Rigid Bonds:	31.0
TPSA:	206.83 ? Topological Polar Surface Area.	H-Bond Acceptor:	15.0
H-Bond Donor:	5.0	Rings:	5.0
Heavy Atoms:	21.0

MedChem Properties

QED Drug-Likeness Score:	0.2	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	6.113	Fsp³:	0.387
MCE-18:	166.884 ? 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:	0	PAINS Alert:	0
Colloidal aggregators:	0.865	Fluc inhibitor:	0.191 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.275 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.506 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.413	Promiscuous compounds:	0.004

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.954	MDCK Permeability:	-4.759
Pgp-inhibitor:	0.014	Pgp-substrate:	0.0
PAMPA:	0.027 ? 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):	0.0
20% Bioavailability (F20%):	0.002	30% Bioavailability (F30%):	0.031
50% Bioavailability (F50%):	0.984

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.173	MRP1:	1.0
Plasma Protein Binding (PPB):	97.244%	Volume Distribution (VD):	0.02
Fu:	1.616% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.11
BSEP inhibitor:	1.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.991
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	1.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.808
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.079
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.023 ? 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):

0.448

Half-life (T1/2):

4.535

ADMET: Toxicity

hERG Blockers:	0.016	hERG Blockers (10um):	0.253
Human Hepatotoxicity (H-HT):	0.061	Drug-induced Liver Injury (DILI):	1.0
AMES Toxicity:	0.997	Rat Oral Acute Toxicity:	0.996
Maximum Recommended Daily Dose:	1.0	Skin Sensitization:	1.0
Carcinogencity:	0.999	Eye Corrosion:	0.0
Eye Irritation:	0.018	Respiratory Toxicity:	0.981
Drug-induced Neurotoxicity:	0.975	Ototoxicity:	0.638
Hematotoxicity:	0.0	Drug-induced Nephrotoxicity:	0.745
Genotoxicity:	1.0	RPMI-8226 Immunitoxicity:	0.066
A549 Cytotoxicity:	0.007	Hek293 Cytotoxicity:	0.934
BCF:	1.224 ? 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:	4.336 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.125 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.649 ? 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
NPO3261	Aplysina archeri	Species	Aplysinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[1324982]
NPO3261	Aplysina archeri	Species	Aplysinidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3261	Aplysina archeri	Species	Aplysinidae	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
ED50	1
Ratio	1
ID50	1

Activity Type	# Activity
Organism	1
Others	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
NPT15412	Organism	Feline leukemia virus	Feline leukemia virus	ED50	=	42.0	uM	PMID[1324982]
NPT2	Others	Unspecified	n.a.	Ratio	>	11.0	n.a.	PMID[1324982]
NPT27	Others	Unspecified	n.a.	ID50	>	449.0	uM	PMID[1324982]

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 NPC487915 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	17539
0.1-0.2	32143
0.2-0.3	107
0.3-0.4	21
0.4-0.5	8
0.5-0.6	22
0.6-0.7	9
0.7-0.8	0
0.8-0.85	5
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8101	Intermediate Similarity	NPC483876
0.8101	Intermediate Similarity	NPC487914
0.8101	Intermediate Similarity	NPC489611
0.8101	Intermediate Similarity	NPC600925
0.8101	Intermediate Similarity	NPC604329
0.7529	Intermediate Similarity	NPC489612
0.6742	Remote Similarity	NPC480151
0.6591	Remote Similarity	NPC77435
0.6591	Remote Similarity	NPC259071
0.6552	Remote Similarity	NPC202866
0.6304	Remote Similarity	NPC606574
0.6264	Remote Similarity	NPC603425
0.617	Remote Similarity	NPC607100
0.6067	Remote Similarity	NPC607066
0.6064	Remote Similarity	NPC611077
0.596	Remote Similarity	NPC227953
0.5938	Remote Similarity	NPC609979
0.5882	Remote Similarity	NPC487872
0.5882	Remote Similarity	NPC608122
0.5862	Remote Similarity	NPC487873
0.5823	Remote Similarity	NPC487917
0.58	Remote Similarity	NPC603698
0.5789	Remote Similarity	NPC1702
0.5641	Remote Similarity	NPC158672
0.5464	Remote Similarity	NPC174607
0.5464	Remote Similarity	NPC147847
0.5429	Remote Similarity	NPC606635
0.5287	Remote Similarity	NPC313173
0.5281	Remote Similarity	NPC66855
0.5281	Remote Similarity	NPC181086
0.5227	Remote Similarity	NPC81079
0.5227	Remote Similarity	NPC304257
0.5172	Remote Similarity	NPC145149
0.5116	Remote Similarity	NPC473262
0.5116	Remote Similarity	NPC202166
0.5068	Remote Similarity	NPC30521
0.5056	Remote Similarity	NPC260270

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC487915 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3364
0.1-0.2	5772
0.2-0.3	14
0.3-0.4	0
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