NPASS Compound

Natural Product: NPC273359

Natural Product ID	NPC273359
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	XCGSFFUVFURLIX-BRMNWJGKSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	115248
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0002679] Ergoline and derivatives [CHEMONTID:0002680] Lysergic acids and derivatives [CHEMONTID:0002030] Ergopeptines [CHEMONTID:0000371] Ergotamines, dihydroergotamines, and derivatives

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 78 85 0 0 0 0 0 0 0 0999 V2000 0.0794 -0.3023 -1.5027 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8938 -0.2332 -0.2283 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7609 0.9911 -0.3849 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4796 2.1750 -0.1228 O 0 0 0 0 0 0 0 0 0 0 0 0 2.9931 0.5231 -0.9012 N 0 0 0 0 0 0 0 0 0 0 0 0 4.0768 1.2056 -1.5730 C 0 0 1 0 0 0 0 0 0 0 0 0 4.7353 2.2699 -0.7367 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3162 1.7466 0.5466 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6202 1.3099 0.5619 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1359 0.8394 1.7526 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3867 0.7976 2.9079 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0829 1.2427 2.8612 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5556 1.7116 1.6918 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0128 0.2840 -2.2459 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1143 0.6710 -2.7024 O 0 0 0 0 0 0 0 0 0 0 0 0 4.7028 -1.0919 -2.4090 N 0 0 0 0 0 0 0 0 0 0 0 0 5.3627 -2.1397 -3.1511 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2988 -3.3112 -2.2005 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1432 -3.0112 -1.2835 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5510 -1.7085 -1.7864 C 0 0 1 0 0 0 0 0 0 0 0 0 3.0226 -0.8814 -0.6401 C 0 0 1 0 0 0 0 0 0 0 0 0 3.8723 -1.1682 0.4490 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7854 -1.2990 -0.2912 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2000 -0.2584 0.9776 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.9222 -0.0869 1.4452 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1789 0.2773 0.7646 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.2486 -0.7233 0.9944 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4602 -0.3581 0.6368 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6187 -1.2367 0.8040 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4750 -2.4831 1.3737 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6313 -3.2285 1.4997 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.8782 -2.7517 1.0756 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.0011 -1.4907 0.5031 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8573 -0.7824 0.3913 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.0642 0.4282 -0.1752 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9706 1.3727 -0.4026 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6282 0.9652 0.0502 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.0062 1.9451 0.9269 N 0 0 0 0 0 0 0 0 0 0 0 0 -3.8163 3.2156 0.2289 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7496 1.5406 1.4454 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.4180 0.4707 -0.4293 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.9722 -0.7158 -0.0050 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.0822 -0.2534 2.8589 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6610 -1.0959 -1.4784 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2638 0.6793 -1.8690 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8203 -0.6197 -2.3045 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6221 1.8051 -2.4437 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5674 2.7681 -1.2563 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0036 3.0726 -0.4928 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2533 1.3329 -0.3433 H 0 0 0 0 0 0 0 0 0 0 0 0 8.1612 0.4954 1.7707 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7567 0.4366 3.8554 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4864 1.2071 3.7939 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5300 2.0580 1.6788 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4116 -1.8923 -3.4148 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8073 -2.4156 -4.0746 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1367 -4.2761 -2.7233 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2529 -3.3483 -1.6475 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5320 -2.9039 -0.2672 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3620 -3.8065 -1.3513 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7930 -1.9691 -2.5367 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4554 -1.8194 1.0781 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9851 0.4643 -0.2908 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0202 -1.6647 1.4214 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5190 -2.8217 1.6861 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5279 -4.2063 1.9462 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.7695 -3.3456 1.1806 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2341 2.3258 0.1512 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9447 1.7310 -1.4805 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9523 0.9737 -0.8693 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3343 3.0190 -0.7329 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0792 3.7783 0.8603 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7530 3.7855 0.1775 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8652 1.2175 2.5202 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9535 2.2833 1.4342 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.0134 1.2551 -0.8770 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.9690 -1.0009 -0.0514 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3101 -0.6038 3.3749 H 0 0 0 0 0 0 0 0 0 0 0 0 2 1 1 6 2 3 1 0 3 4 2 0 3 5 1 0 5 6 1 0 6 7 1 0 7 8 1 0 8 9 2 0 9 10 1 0 10 11 2 0 11 12 1 0 12 13 2 0 6 14 1 0 14 15 2 0 14 16 1 0 16 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 20 21 1 0 21 22 1 1 21 23 1 0 2 24 1 0 24 25 2 3 25 26 1 0 26 27 1 0 27 28 2 0 28 29 1 0 29 30 2 0 30 31 1 0 31 32 2 0 32 33 1 0 33 34 2 0 34 35 1 0 35 36 1 0 36 37 1 0 37 38 1 0 38 39 1 0 38 40 1 0 35 41 2 0 41 42 1 0 25 43 1 0 23 2 1 0 40 26 1 0 21 5 1 0 37 28 1 0 13 8 1 0 20 16 1 0 34 29 1 0 42 33 1 0 1 44 1 0 1 45 1 0 1 46 1 0 6 47 1 6 7 48 1 0 7 49 1 0 9 50 1 0 10 51 1 0 11 52 1 0 12 53 1 0 13 54 1 0 17 55 1 0 17 56 1 0 18 57 1 0 18 58 1 0 19 59 1 0 19 60 1 0 20 61 1 6 22 62 1 0 26 63 1 6 27 64 1 0 30 65 1 0 31 66 1 0 32 67 1 0 36 68 1 0 36 69 1 0 37 70 1 6 39 71 1 0 39 72 1 0 39 73 1 0 40 74 1 0 40 75 1 0 41 76 1 0 42 77 1 0 43 78 1 0 M END

Standard InCHIKey	XCGSFFUVFURLIX-BRMNWJGKSA-N
Standard InCHI	InChI=1S/C33H35N5O5/c1-32(35-29(39)21-15-23-22-10-6-11-24-28(22)20(17-34-24)16-25(23)36(2)18-21)31(41)38-26(14-19-8-4-3-5-9-19)30(40)37-13-7-12-27(37)33(38,42)43-32/h3-6,8-11,15,17,21,25-27,34,42H,7,12-14,16,18H2,1-2H3,(H,35,39)/t21-,25+,26-,27-,32+,33-/m0/s1
SMILES	C[C@@]1(C(=O)N2[C@@H](Cc3ccccc3)C(=O)N3CCC[C@H]3[C@]2(O)O1)N=C([C@H]1C=C2c3cccc4c3c(C[C@H]2N(C)C1)c[nH]4)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	581.26	Volume:	580.806 ? Van der Waals volume.
Dense:	1.001	LogP:	2.153 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.283 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.523 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	4.0	Rigid Bonds:	42.0
TPSA:	121.7 ? Topological Polar Surface Area.	H-Bond Acceptor:	10.0
H-Bond Donor:	3.0	Rings:	8.0
Heavy Atoms:	10.0

MedChem Properties

QED Drug-Likeness Score:	0.322	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.975	Fsp³:	0.424
MCE-18:	159.532 ? 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:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.463	Fluc inhibitor:	0.033 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.889 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.985 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.001	Promiscuous compounds:	0.93

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.742	MDCK Permeability:	-5.144
Pgp-inhibitor:	0.988	Pgp-substrate:	1.0
PAMPA:	0.26 ? 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):	0.003
20% Bioavailability (F20%):	1.0	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.001	MRP1:	0.947
Plasma Protein Binding (PPB):	92.567%	Volume Distribution (VD):	0.369
Fu:	5.669% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.981
OATP1B3 inhibitor:	0.172	BCRP inhibitor:	0.45
BSEP inhibitor:	0.99

ADMET: Metabolism

CYP1A2-inhibitor:	1.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.999	CYP2C19-substrate:	0.073
CYP2C9-inhibitor:	0.925	CYP2C9-substrate:	0.01
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.978
CYP3A4-inhibitor:	1.0	CYP3A4-substrate:	0.008
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.0
HLM stability:	0.988 ? 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):

11.085

Half-life (T1/2):

2.103

ADMET: Toxicity

hERG Blockers:	0.058	hERG Blockers (10um):	0.101
Human Hepatotoxicity (H-HT):	0.999	Drug-induced Liver Injury (DILI):	0.961
AMES Toxicity:	0.808	Rat Oral Acute Toxicity:	0.886
Maximum Recommended Daily Dose:	0.956	Skin Sensitization:	0.999
Carcinogencity:	0.951	Eye Corrosion:	0.0
Eye Irritation:	0.062	Respiratory Toxicity:	0.742
Drug-induced Neurotoxicity:	0.786	Ototoxicity:	0.736
Hematotoxicity:	0.295	Drug-induced Nephrotoxicity:	0.82
Genotoxicity:	1.0	RPMI-8226 Immunitoxicity:	0.039
A549 Cytotoxicity:	0.026	Hek293 Cytotoxicity:	0.74
BCF:	1.136 ? 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:	3.902 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.354 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.858 ? 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
NPO24009	Claviceps purpurea	Species	Clavicipitaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17841110]
NPO24009	Claviceps purpurea	Species	Clavicipitaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20778930]
NPO24009	Claviceps purpurea	Species	Clavicipitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24009	Claviceps purpurea	Species	Clavicipitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24009	Claviceps purpurea	Species	Clavicipitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24009	Claviceps purpurea	Species	Clavicipitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO24009	Claviceps purpurea	Species	Clavicipitaceae	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

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 NPC273359 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	21156
0.1-0.2	27402
0.2-0.3	1259
0.3-0.4	31
0.4-0.5	4
0.5-0.6	3
0.6-0.7	1
0.7-0.8	3
0.8-0.85	0
0.85-0.9	1
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC191382
0.8969	High Similarity	NPC56109
0.7549	Intermediate Similarity	NPC155444
0.6036	Remote Similarity	NPC603739
0.5657	Remote Similarity	NPC68354
0.534	Remote Similarity	NPC611966
0.5146	Remote Similarity	NPC604662

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC273359 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	2935
0.1-0.2	5948
0.2-0.3	235
0.3-0.4	9
0.4-0.5	3
0.5-0.6	12
0.6-0.7	3
0.7-0.8	3
0.8-0.85	0
0.85-0.9	0
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
1.0	High Similarity	NPD7781	Phase 4
0.9293	High Similarity	NPD7780	Approved
0.7358	Intermediate Similarity	NPD7790	Approved
0.7358	Intermediate Similarity	NPD7791	Phase 4
0.7027	Intermediate Similarity	NPD7789	Approved
0.6577	Remote Similarity	NPD7952	Approved
0.6577	Remote Similarity	NPD7953	Pre-clinical
0.6053	Remote Similarity	NPD7717	Phase 4
0.5887	Remote Similarity	NPD7951	Phase 4
0.5798	Remote Similarity	NPD7716	Approved
0.57	Remote Similarity	NPD4079	Phase 4
0.5659	Remote Similarity	NPD7950	Approved
0.5657	Remote Similarity	NPD3506	Phase 4
0.5431	Remote Similarity	NPD7731	Pre-clinical
0.5377	Remote Similarity	NPD4076	Approved
0.5333	Remote Similarity	NPD3505	Approved
0.5294	Remote Similarity	NPD7824	Approved
0.525	Remote Similarity	NPD7271	Approved
0.5207	Remote Similarity	NPD7730	Approved
0.5051	Remote Similarity	NPD4075	Phase 2

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