NPASS Compound

Natural Product: NPC235885

Natural Product ID	NPC235885
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	YLUDCJQWXLSNNQ-NWJVICLCSA-N
IUPAC Name	n.a.
Synonyms	19-O-Acetylchaetoglobosin D
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL255720
PubChem CID	44448146
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001819] Isoindoles and derivatives [CHEMONTID:0002496] Isoindolines [CHEMONTID:0001820] Isoindolones

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 -4.6856 3.9111 3.7174 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2705 3.7793 2.2868 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9884 4.8657 1.6790 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1846 2.5881 1.6293 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.7928 2.5287 0.2982 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5924 1.7573 0.0333 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2346 1.7077 -1.1655 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7278 0.9986 0.9310 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7945 0.2500 0.4493 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2116 -0.6276 1.0034 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3898 -0.6848 2.2119 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9917 -1.4713 -0.0005 C 0 0 1 0 0 0 0 0 0 0 0 0 1.5653 -0.5823 -0.9945 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8053 -0.3934 -0.7545 N 0 0 0 0 0 0 0 0 0 0 0 0 3.2376 -1.0983 0.3856 C 0 0 2 0 0 0 0 0 0 0 0 0 2.1195 -2.1203 0.6520 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5920 -3.4217 0.1325 C 0 0 2 0 0 0 0 0 0 0 0 0 3.5720 -3.3256 -1.0390 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4858 -4.2700 -0.3539 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3332 -5.5304 -0.0410 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5042 -3.5696 -1.2678 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0763 -2.4333 -0.5244 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.1630 -1.7887 -1.2440 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4378 -1.8860 -0.8111 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5797 -1.1834 -1.5607 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2598 -0.2814 -0.5565 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.0927 0.8124 -0.9704 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9144 2.0598 -0.6011 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9703 3.0500 -0.9958 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3854 -1.2959 0.0322 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4783 -4.4793 -1.6060 O 0 0 0 0 0 0 0 0 0 0 0 0 3.6415 -0.3139 1.5797 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7991 0.5760 1.2028 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1359 0.2717 1.4880 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9241 1.2465 1.0062 N 0 0 0 0 0 0 0 0 0 0 0 0 6.1406 2.1694 0.4203 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8133 1.7650 0.5355 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8051 2.5473 0.0160 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1206 3.7413 -0.6245 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4352 4.1610 -0.7502 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4190 3.3538 -0.2180 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9681 0.0532 -2.1163 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0546 2.9702 4.1295 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5402 4.6338 3.7136 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8890 4.3851 4.3265 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5927 3.5688 -0.0481 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9453 1.1354 1.9249 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6705 0.3537 -0.6541 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1730 -1.6631 0.0601 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0167 -2.1473 1.7551 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1220 -3.9369 0.9851 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5947 -3.4896 -0.6447 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4352 -2.4489 -1.6634 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4210 -4.2028 -1.7450 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4893 -6.0734 -0.4467 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0082 -6.0706 0.6074 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0938 -3.2550 -2.1587 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4643 -2.9036 0.4510 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9651 -1.2406 -2.1752 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7429 -2.4392 0.0558 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2111 -2.0133 -1.9282 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1845 -0.6551 -2.4363 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7160 -0.2122 0.3895 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9608 0.6282 -1.6529 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6970 3.6303 -1.8835 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9564 2.5330 -1.1409 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1053 3.7149 -0.1177 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8032 -2.1704 0.3581 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8241 -0.7846 0.8789 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0342 -1.5368 -0.8141 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2072 -4.0765 -2.1396 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9963 -0.9796 2.3718 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8439 0.3226 2.0139 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4920 -0.5922 2.0048 H 0 0 0 0 0 0 0 0 0 0 0 0 7.9628 1.2847 1.0728 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7951 2.2077 0.1310 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3175 4.3335 -1.0213 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6468 5.0864 -1.2497 H 0 0 0 0 0 0 0 0 0 0 0 0 7.4572 3.6960 -0.3234 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3175 0.9706 -2.3929 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 2 0 2 4 1 0 4 5 1 0 5 6 1 0 6 7 2 0 6 8 1 0 8 9 2 0 9 10 1 0 10 11 2 0 12 10 1 1 12 13 1 0 13 14 2 0 14 15 1 0 15 16 1 0 16 17 1 0 17 18 1 0 17 19 1 0 19 20 2 0 19 21 1 0 21 22 1 0 22 23 1 0 23 24 2 0 24 25 1 0 25 26 1 0 26 27 1 0 27 28 2 0 28 29 1 0 26 30 1 0 21 31 1 0 15 32 1 0 32 33 1 0 33 34 2 0 34 35 1 0 35 36 1 0 36 37 2 0 37 38 1 0 38 39 2 0 39 40 1 0 40 41 2 0 13 42 1 0 28 5 1 0 37 33 1 0 16 12 1 0 41 36 1 0 22 12 1 0 1 43 1 0 1 44 1 0 1 45 1 0 5 46 1 6 8 47 1 0 9 48 1 0 15 49 1 6 16 50 1 1 17 51 1 1 18 52 1 0 18 53 1 0 18 54 1 0 20 55 1 0 20 56 1 0 21 57 1 6 22 58 1 1 23 59 1 0 24 60 1 0 25 61 1 0 25 62 1 0 26 63 1 1 27 64 1 0 29 65 1 0 29 66 1 0 29 67 1 0 30 68 1 0 30 69 1 0 30 70 1 0 31 71 1 0 32 72 1 0 32 73 1 0 34 74 1 0 35 75 1 0 38 76 1 0 39 77 1 0 40 78 1 0 41 79 1 0 42 80 1 0 M END

Standard InCHIKey	YLUDCJQWXLSNNQ-NWJVICLCSA-N
Standard InCHI	InChI=1S/C34H38N2O6/c1-18-9-8-11-25-31(40)21(4)20(3)30-27(16-23-17-35-26-12-7-6-10-24(23)26)36-33(41)34(25,30)29(39)14-13-28(38)32(19(2)15-18)42-22(5)37/h6-8,10-15,17-18,20,25,27,30-32,35,40H,4,9,16H2,1-3,5H3,(H,36,41)/b11-8+,14-13+,19-15-/t18-,20+,25-,27-,30-,31+,32+,34+/m0/s1
SMILES	CC(=O)O[C@H]1C(=O)/C=C/C(=O)[C@@]23C(=N[C@H]([C@@H]2[C@H](C)C(=C)[C@H]([C@@H]3/C=C/C[C@@H](/C=C1/C)C)O)Cc1c[nH]c2c1cccc2)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	570.27	Volume:	596.935 ? Van der Waals volume.
Dense:	0.955	LogP:	2.974 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.963 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.138 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	4.0	Rigid Bonds:	36.0
TPSA:	129.05 ? Topological Polar Surface Area.	H-Bond Acceptor:	8.0
H-Bond Donor:	3.0	Rings:	5.0
Heavy Atoms:	8.0

MedChem Properties

QED Drug-Likeness Score:	0.352	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	6.197	Fsp³:	0.412
MCE-18:	148.75 ? 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:	Accepted	BMS Rule:	1
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.924	Fluc inhibitor:	0.36 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.158 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.397 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.01	Promiscuous compounds:	0.593

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.339	MDCK Permeability:	-4.901
Pgp-inhibitor:	0.139	Pgp-substrate:	0.988
PAMPA:	0.995 ? 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):	0.008
20% Bioavailability (F20%):	0.907	30% Bioavailability (F30%):	0.999
50% Bioavailability (F50%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.867
Plasma Protein Binding (PPB):	83.921%	Volume Distribution (VD):	-0.215
Fu:	12.913% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.992
OATP1B3 inhibitor:	0.937	BCRP inhibitor:	0.001
BSEP inhibitor:	0.998

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.008
CYP2C19-inhibitor:	0.001	CYP2C19-substrate:	0.072
CYP2C9-inhibitor:	0.002	CYP2C9-substrate:	0.383
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.439
CYP3A4-inhibitor:	0.003	CYP3A4-substrate:	0.772
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.962 ? 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):

7.043

Half-life (T1/2):

0.646

ADMET: Toxicity

hERG Blockers:	0.002	hERG Blockers (10um):	0.006
Human Hepatotoxicity (H-HT):	1.0	Drug-induced Liver Injury (DILI):	1.0
AMES Toxicity:	0.861	Rat Oral Acute Toxicity:	0.525
Maximum Recommended Daily Dose:	0.554	Skin Sensitization:	1.0
Carcinogencity:	0.923	Eye Corrosion:	0.0
Eye Irritation:	0.872	Respiratory Toxicity:	0.782
Drug-induced Neurotoxicity:	0.366	Ototoxicity:	0.637
Hematotoxicity:	0.76	Drug-induced Nephrotoxicity:	0.998
Genotoxicity:	1.0	RPMI-8226 Immunitoxicity:	0.135
A549 Cytotoxicity:	0.211	Hek293 Cytotoxicity:	0.349
BCF:	1.122 ? 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:	4.011 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.666 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.112 ? 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
NPO32963	Acremonium sp.	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	PMID[12444684]
NPO32963	Acremonium sp.	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	PMID[16441074]
NPO32963	Acremonium sp.	Species	n.a.	Eukaryota	n.a.	Australian	n.a.	PMID[18288804]
NPO32963	Acremonium sp.	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	PMID[19199645]
NPO32963	Acremonium sp.	Species	n.a.	Eukaryota	n.a.	Mangrove Rhizophora apiculata	n.a.	PMID[22524636]
NPO32963	Acremonium sp.	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	PMID[22524636]
NPO32963	Acremonium sp.	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	PMID[25689430]
NPO32963	Acremonium sp.	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	PMID[26928174]
NPO32963	Acremonium sp.	Species	n.a.	Eukaryota	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

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

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 NPC235885 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	11184
0.1-0.2	36609
0.2-0.3	1832
0.3-0.4	182
0.4-0.5	25
0.5-0.6	9
0.6-0.7	13
0.7-0.8	0
0.8-0.85	1
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8511	High Similarity	NPC2395
0.8191	Intermediate Similarity	NPC203614
0.7732	Intermediate Similarity	NPC204491
0.6931	Remote Similarity	NPC87856
0.6765	Remote Similarity	NPC141428
0.6667	Remote Similarity	NPC225821
0.6538	Remote Similarity	NPC151976
0.6538	Remote Similarity	NPC487663
0.6538	Remote Similarity	NPC147446
0.6408	Remote Similarity	NPC98715
0.6373	Remote Similarity	NPC267965
0.6286	Remote Similarity	NPC46225
0.6275	Remote Similarity	NPC195239
0.6238	Remote Similarity	NPC157828
0.619	Remote Similarity	NPC132211
0.6111	Remote Similarity	NPC57690
0.5943	Remote Similarity	NPC487662
0.5888	Remote Similarity	NPC487661
0.5849	Remote Similarity	NPC271862
0.5833	Remote Similarity	NPC487664
0.5446	Remote Similarity	NPC267926
0.5364	Remote Similarity	NPC266192
0.5357	Remote Similarity	NPC487657
0.5263	Remote Similarity	NPC487658
0.513	Remote Similarity	NPC487660

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC235885 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3125
0.1-0.2	5789
0.2-0.3	203
0.3-0.4	33
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