NPASS Compound

Natural Product: NPC188222

Natural Product ID	NPC188222
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Gemmacolide G
IUPAC Name	n.a.
Synonyms	Gemmacolide G
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL1812327
PubChem CID	53468495
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 82 85 0 0 0 0 0 0 0 0999 V2000 -4.6329 3.0368 0.5436 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6833 2.2143 0.8099 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3190 2.5620 0.3233 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3323 1.7826 0.6250 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1199 1.8272 0.2863 C 0 0 1 0 0 0 0 0 0 0 0 0 0.3898 0.5030 -0.5008 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.2707 0.8342 -1.8351 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1501 -0.6660 0.2424 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.4203 -1.2919 -0.1917 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5886 -1.2874 0.8195 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.3829 -2.6021 0.6056 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.9157 -3.1412 1.8944 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5216 -2.2088 -0.2405 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0816 -2.9678 -1.0519 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.7946 -0.8888 0.0656 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5832 -0.2515 0.5469 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.8968 0.8653 1.4550 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.2854 0.8838 3.0712 Cl 0 0 0 0 0 0 0 0 0 0 0 0 -2.0815 -1.4117 2.0802 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.9032 -0.9628 -1.4732 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.0725 -1.8055 -2.5332 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7744 -3.0144 -2.3873 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5942 -1.3384 -3.8418 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8559 -1.7495 0.6109 C 0 0 2 0 0 0 0 0 0 0 0 0 0.3986 -3.1230 0.8518 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8732 -2.2292 1.9540 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2177 -1.6287 0.0517 C 0 0 1 0 0 0 0 0 0 0 0 0 2.7110 -0.1964 0.1410 C 0 0 1 0 0 0 0 0 0 0 0 0 1.8290 0.5055 -0.8487 C 0 0 2 0 0 0 0 0 0 0 0 0 2.3422 1.7359 -1.2136 O 0 0 0 0 0 0 0 0 0 0 0 0 2.8399 2.0110 -2.4752 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8079 1.0600 -3.3208 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3990 3.2978 -2.9207 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7049 0.3275 1.4202 O 0 0 0 0 0 0 0 0 0 0 0 0 3.8420 0.7807 2.0272 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9471 0.7380 1.4395 O 0 0 0 0 0 0 0 0 0 0 0 0 3.7244 1.3308 3.4192 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1417 -2.4075 0.7592 O 0 0 0 0 0 0 0 0 0 0 0 0 3.9846 -3.3390 0.1802 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9207 -3.4985 -1.0489 O 0 0 0 0 0 0 0 0 0 0 0 0 4.9196 -4.0955 1.0678 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4636 2.9652 -0.4199 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3745 3.8622 0.1290 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8456 3.5791 1.2592 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7976 5.1228 -0.5708 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6409 2.8287 0.8756 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4717 3.9451 -0.0070 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2222 3.4460 -0.2564 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6436 0.9897 1.3397 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6461 1.6806 1.2510 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3011 1.7735 -2.1613 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0026 0.1323 -2.6428 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2868 1.1820 -1.7844 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3652 -0.2671 1.2862 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2176 -2.4054 -0.3217 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7277 -3.3633 0.1475 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1939 -2.3772 2.6353 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2800 -3.9613 2.3280 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8843 -3.6677 1.6420 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2445 0.2569 -0.4333 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0368 0.8329 1.5788 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1633 -2.2685 2.5207 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0089 -1.8012 -4.6808 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6669 -1.6243 -3.9791 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4919 -0.2427 -3.9664 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5727 -3.4680 1.1888 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1236 -3.9589 0.6831 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2982 -1.9043 -1.0348 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7409 -0.1766 -0.2610 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9166 -0.1494 -1.7855 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6278 3.9542 -3.3320 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9496 3.8304 -2.1164 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1674 3.1299 -3.7270 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5864 1.0273 4.0488 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8239 0.8995 3.9083 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5770 2.4293 3.4048 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9011 -4.2539 0.5735 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4180 -5.0291 1.3496 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1219 -3.5165 1.9843 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9106 5.2589 -0.4925 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3775 5.9717 0.0364 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4633 5.1464 -1.6056 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 6 7 1 6 6 8 1 0 8 9 1 0 9 10 1 0 10 11 1 0 11 12 1 0 11 13 1 0 13 14 2 0 13 15 1 0 15 16 1 0 16 17 1 0 17 18 1 0 10 19 1 1 9 20 1 0 20 21 1 0 21 22 2 0 21 23 1 0 8 24 1 0 24 25 1 0 25 26 1 0 24 27 1 0 27 28 1 0 28 29 1 0 29 30 1 0 30 31 1 0 31 32 2 0 31 33 1 0 28 34 1 0 34 35 1 0 35 36 2 0 35 37 1 0 27 38 1 0 38 39 1 0 39 40 2 0 39 41 1 0 5 42 1 0 42 43 1 0 43 44 2 0 43 45 1 0 17 2 1 0 24 26 1 1 29 6 1 0 16 10 1 0 1 46 1 0 1 47 1 0 3 48 1 0 4 49 1 0 5 50 1 1 7 51 1 0 7 52 1 0 7 53 1 0 8 54 1 1 9 55 1 6 11 56 1 6 12 57 1 0 12 58 1 0 12 59 1 0 16 60 1 6 17 61 1 1 19 62 1 0 23 63 1 0 23 64 1 0 23 65 1 0 25 66 1 0 25 67 1 0 27 68 1 6 28 69 1 6 29 70 1 6 33 71 1 0 33 72 1 0 33 73 1 0 37 74 1 0 37 75 1 0 37 76 1 0 41 77 1 0 41 78 1 0 41 79 1 0 45 80 1 0 45 81 1 0 45 82 1 0 M END

Standard InCHIKey	CMKNGEIJCJJGAQ-DFOHHMFPSA-N
Standard InCHI	InChI=1S/C30H37ClO14/c1-12-9-10-19(40-14(3)32)28(8)22(26(44-18(7)36)30(38)13(2)27(37)45-23(30)20(12)31)29(11-39-29)25(43-17(6)35)21(41-15(4)33)24(28)42-16(5)34/h9-10,13,19-26,38H,1,11H2,2-8H3/b10-9+/t13-,19-,20-,21+,22+,23-,24-,25+,26-,28+,29-,30-/m0/s1
SMILES	C=C1/C=C/[C@@H]([C@]2(C)[C@@H]([C@@H]([C@@]3([C@@H](C)C(=O)O[C@H]3[C@H]1Cl)O)OC(=O)C)[C@@]1(CO1)[C@@H]([C@@H]([C@@H]2OC(=O)C)OC(=O)C)OC(=O)C)OC(=O)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	656.19	Volume:	610.393 ? Van der Waals volume.
Dense:	1.075	LogP:	1.352 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.852 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.428 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	10.0	Rigid Bonds:	29.0
TPSA:	190.56 ? Topological Polar Surface Area.	H-Bond Acceptor:	14.0
H-Bond Donor:	1.0	Rings:	4.0
Heavy Atoms:	15.0

MedChem Properties

QED Drug-Likeness Score:	0.191	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	6.472	Fsp³:	0.667
MCE-18:	130.24 ? 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:	1
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.474	Fluc inhibitor:	0.003 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.007 ? 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:	0.44	Promiscuous compounds:	0.568

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.197	MDCK Permeability:	-4.769
Pgp-inhibitor:	0.444	Pgp-substrate:	0.509
PAMPA:	0.976 ? 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%):	0.017	30% Bioavailability (F30%):	0.802
50% Bioavailability (F50%):	0.913

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.999
Plasma Protein Binding (PPB):	54.284%	Volume Distribution (VD):	-0.398
Fu:	40.219% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.998	BCRP inhibitor:	0.004
BSEP inhibitor:	0.99

ADMET: Metabolism

CYP1A2-inhibitor:	0.016	CYP1A2-substrate:	0.003
CYP2C19-inhibitor:	0.014	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.053
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.002	CYP3A4-substrate:	0.021
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.994 ? 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):

3.183

Half-life (T1/2):

1.22

ADMET: Toxicity

hERG Blockers:	0.001	hERG Blockers (10um):	0.005
Human Hepatotoxicity (H-HT):	0.879	Drug-induced Liver Injury (DILI):	0.995
AMES Toxicity:	0.992	Rat Oral Acute Toxicity:	0.337
Maximum Recommended Daily Dose:	0.509	Skin Sensitization:	1.0
Carcinogencity:	0.679	Eye Corrosion:	0.02
Eye Irritation:	0.379	Respiratory Toxicity:	0.666
Drug-induced Neurotoxicity:	0.342	Ototoxicity:	0.314
Hematotoxicity:	0.829	Drug-induced Nephrotoxicity:	0.994
Genotoxicity:	0.998	RPMI-8226 Immunitoxicity:	0.573
A549 Cytotoxicity:	0.941	Hek293 Cytotoxicity:	0.341
BCF:	0.574 ? 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:	3.493 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.151 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.81 ? 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
NPO15994	Dichotella gemmacea	Species	Ellisellidae	Eukaryota	n.a.	South China Sea	n.a.	PMID[21721519]
NPO15994	Dichotella gemmacea	Species	Ellisellidae	Eukaryota	n.a.	n.a.	n.a.	PMID[21721519]
NPO15994	Dichotella gemmacea	Species	Ellisellidae	Eukaryota	n.a.	South China Sea	n.a.	PMID[22647719]
NPO15994	Dichotella gemmacea	Species	Ellisellidae	Eukaryota	n.a.	n.a.	n.a.	PMID[23477504]
NPO15994	Dichotella gemmacea	Species	Ellisellidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15994	Dichotella gemmacea	Species	Ellisellidae	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
Cell line	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
NPT81	Cell line	A549	Homo sapiens	IC50	=	8400.0	nM	PMID[21721519]
NPT2351	Cell line	MG-63	Homo sapiens	IC50	=	38400.0	nM	PMID[21721519]

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 NPC188222 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	21559
0.1-0.2	27530
0.2-0.3	708
0.3-0.4	24
0.4-0.5	14
0.5-0.6	8
0.6-0.7	12
0.7-0.8	0
0.8-0.85	0
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8955	High Similarity	NPC303006
0.7286	Intermediate Similarity	NPC483349
0.6944	Remote Similarity	NPC310035
0.6944	Remote Similarity	NPC600649
0.6944	Remote Similarity	NPC601003
0.6712	Remote Similarity	NPC140409
0.6667	Remote Similarity	NPC282003
0.6575	Remote Similarity	NPC602049
0.6267	Remote Similarity	NPC606141
0.6216	Remote Similarity	NPC608960
0.6164	Remote Similarity	NPC483348
0.6154	Remote Similarity	NPC470466
0.6154	Remote Similarity	NPC170294
0.6026	Remote Similarity	NPC601379
0.5949	Remote Similarity	NPC600027
0.5833	Remote Similarity	NPC470185
0.5811	Remote Similarity	NPC609324
0.5732	Remote Similarity	NPC483347
0.5309	Remote Similarity	NPC606973
0.5128	Remote Similarity	NPC89018
0.5125	Remote Similarity	NPC605719
0.5119	Remote Similarity	NPC483351

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC188222 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6944
0.1-0.2	2194
0.2-0.3	12
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