NPASS Compound

Natural Product: NPC249875

Natural Product ID	NPC249875
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	NESVMZOPWPCFAU-YTVPIDCWSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	10030389
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

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 77 83 0 0 0 0 0 0 0 0999 V2000 -4.8243 3.4279 -0.4861 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9947 2.5501 -0.3865 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4808 2.6482 1.0806 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9659 1.1423 -0.8146 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0619 0.1719 -0.2131 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.3655 -1.2379 -0.7694 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0781 -1.4168 -1.7381 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.7305 -2.2570 -0.0330 N 0 0 0 0 0 0 0 0 0 0 0 0 -4.8619 -3.6842 0.0418 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3880 -4.0925 0.1261 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8620 -3.1035 1.1399 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6428 -1.8327 0.9069 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.8126 -0.8736 0.1496 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.6550 0.2481 -0.4269 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.6385 1.0145 -1.0333 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7139 1.6391 -2.1010 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4718 0.8759 -0.0705 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.2943 2.2323 0.5650 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3209 0.4027 -0.7664 N 0 0 0 0 0 0 0 0 0 0 0 0 0.7914 0.1945 -0.1996 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9922 -0.3007 -0.9339 C 0 0 1 0 0 0 0 0 0 0 0 0 3.0616 0.7193 -0.7800 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3240 0.3481 -0.6443 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3645 1.3594 -0.4968 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1375 2.7252 -0.6976 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2103 3.5755 -0.5249 C 0 0 0 0 0 0 0 0 0 0 0 0 7.4838 3.1183 -0.1645 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6933 1.7678 0.0299 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6234 0.9364 -0.1439 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9591 -0.3677 0.0726 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9825 -1.4550 -0.0539 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6734 -1.0943 -0.6361 C 0 0 1 0 0 0 0 0 0 0 0 0 3.6232 -1.7507 0.1752 N 0 0 0 0 0 0 0 0 0 0 0 0 4.0280 -3.1083 0.3740 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3721 -1.6692 -0.5042 C 0 0 0 0 0 0 0 0 0 0 0 0 8.3184 -0.3103 0.3971 C 0 0 0 0 0 0 0 0 0 0 0 0 8.7304 0.9665 0.3651 N 0 0 0 0 0 0 0 0 0 0 0 0 0.9405 0.4268 1.1721 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.9181 -0.0977 0.8382 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2454 -1.5317 -0.9416 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1802 4.4658 -0.1715 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0074 3.1031 0.1514 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4860 3.4695 -1.5371 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8127 3.0456 -1.0288 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6085 2.4755 1.7435 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2329 1.8867 1.2828 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8066 3.6859 1.2144 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0349 0.7501 -0.6292 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9477 1.1150 -1.9544 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3428 0.0684 0.8773 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3581 -4.1312 -0.8171 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3076 -4.0165 1.0232 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2790 -5.1379 0.4452 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9463 -3.9116 -0.8806 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0447 -3.5230 2.1574 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7769 -2.9717 0.9430 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0670 -1.4779 1.8450 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0404 2.2858 1.4114 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6296 3.0036 -0.1560 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2638 2.4160 0.9309 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7306 -0.3486 -2.0285 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8244 1.7659 -0.7699 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1647 3.0616 -0.9769 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0514 4.6279 -0.6755 H 0 0 0 0 0 0 0 0 0 0 0 0 8.3176 3.7900 -0.0314 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4685 -2.2351 -0.7181 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9063 -1.9814 0.9304 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5619 -1.5384 -1.6469 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3427 -3.2596 1.4272 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7953 -3.4003 -0.3584 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1413 -3.7618 0.1646 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3968 -2.3959 -1.3487 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5894 -2.0699 0.1961 H 0 0 0 0 0 0 0 0 0 0 0 0 8.9334 -1.1494 0.6334 H 0 0 0 0 0 0 0 0 0 0 0 0 9.6765 1.3437 0.5561 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1669 0.2329 1.8170 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8772 -1.5894 -1.6975 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 2 4 1 0 4 5 1 0 5 6 1 0 6 7 2 0 6 8 1 0 8 9 1 0 9 10 1 0 10 11 1 0 11 12 1 0 12 13 1 0 13 14 1 0 14 15 1 0 15 16 2 0 15 17 1 0 17 18 1 1 17 19 1 0 19 20 2 3 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 28 29 2 0 29 30 1 0 30 31 1 0 31 32 1 0 32 33 1 0 33 34 1 0 33 35 1 0 30 36 2 0 36 37 1 0 20 38 1 0 17 39 1 0 13 40 1 6 14 5 1 0 35 21 1 0 12 8 1 0 39 13 1 0 32 23 1 0 29 24 1 0 37 28 1 0 1 41 1 0 1 42 1 0 1 43 1 0 2 44 1 0 3 45 1 0 3 46 1 0 3 47 1 0 4 48 1 0 4 49 1 0 5 50 1 1 9 51 1 0 9 52 1 0 10 53 1 0 10 54 1 0 11 55 1 0 11 56 1 0 12 57 1 1 18 58 1 0 18 59 1 0 18 60 1 0 21 61 1 6 22 62 1 0 25 63 1 0 26 64 1 0 27 65 1 0 31 66 1 0 31 67 1 0 32 68 1 6 34 69 1 0 34 70 1 0 34 71 1 0 35 72 1 0 35 73 1 0 36 74 1 0 37 75 1 0 38 76 1 0 40 77 1 0 M END

Standard InCHIKey	NESVMZOPWPCFAU-YTVPIDCWSA-N
Standard InCHI	InChI=1S/C30H37N5O5/c1-16(2)11-23-27(37)34-10-6-9-24(34)30(39)35(23)28(38)29(3,40-30)32-26(36)18-12-20-19-7-5-8-21-25(19)17(14-31-21)13-22(20)33(4)15-18/h5,7-8,12,14,16,18,22-24,31,39H,6,9-11,13,15H2,1-4H3,(H,32,36)/t18-,22+,23-,24-,29+,30-/m0/s1
SMILES	CC(C)C[C@H]1C(=O)N2CCC[C@H]2[C@]2(N1C(=O)[C@](C)(N=C([C@H]1C=C3c4cccc5c4c(C[C@H]3N(C)C1)c[nH]5)O)O2)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	547.28	Volume:	545.384 ? Van der Waals volume.
Dense:	1.003	LogP:	2.459 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.506 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.812 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	4.0	Rigid Bonds:	36.0
TPSA:	121.7 ? Topological Polar Surface Area.	H-Bond Acceptor:	10.0
H-Bond Donor:	3.0	Rings:	7.0
Heavy Atoms:	10.0

MedChem Properties

QED Drug-Likeness Score:	0.4	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.121	Fsp³:	0.567
MCE-18:	149.128 ? 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:	0.557	Fluc inhibitor:	0.006 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.94 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.976 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.001	Promiscuous compounds:	0.926

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.38	MDCK Permeability:	-4.981
Pgp-inhibitor:	0.03	Pgp-substrate:	0.978
PAMPA:	0.986 ? 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):	0.263
20% Bioavailability (F20%):	0.996	30% Bioavailability (F30%):	0.997
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.009	MRP1:	0.922
Plasma Protein Binding (PPB):	56.909%	Volume Distribution (VD):	0.409
Fu:	38.693% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.997
OATP1B3 inhibitor:	0.981	BCRP inhibitor:	0.663
BSEP inhibitor:	0.804

ADMET: Metabolism

CYP1A2-inhibitor:	1.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	1.0	CYP2C19-substrate:	0.001
CYP2C9-inhibitor:	0.997	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.988
CYP3A4-inhibitor:	1.0	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.0
HLM stability:	0.996 ? 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):

5.695

Half-life (T1/2):

1.872

ADMET: Toxicity

hERG Blockers:	0.056	hERG Blockers (10um):	0.047
Human Hepatotoxicity (H-HT):	0.998	Drug-induced Liver Injury (DILI):	0.976
AMES Toxicity:	0.939	Rat Oral Acute Toxicity:	0.759
Maximum Recommended Daily Dose:	0.823	Skin Sensitization:	1.0
Carcinogencity:	0.962	Eye Corrosion:	0.0
Eye Irritation:	0.056	Respiratory Toxicity:	0.369
Drug-induced Neurotoxicity:	0.174	Ototoxicity:	0.763
Hematotoxicity:	0.412	Drug-induced Nephrotoxicity:	0.567
Genotoxicity:	1.0	RPMI-8226 Immunitoxicity:	0.078
A549 Cytotoxicity:	0.016	Hek293 Cytotoxicity:	0.392
BCF:	0.97 ? 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:	3.75 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.425 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.751 ? 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 NPC249875 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	20059
0.1-0.2	28782
0.2-0.3	995
0.3-0.4	11
0.4-0.5	4
0.5-0.6	2
0.6-0.7	2
0.7-0.8	2
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
0.8913	High Similarity	NPC155444
0.8454	Intermediate Similarity	NPC191382
0.7549	Intermediate Similarity	NPC56109
0.6321	Remote Similarity	NPC603739
0.6129	Remote Similarity	NPC68354
0.5612	Remote Similarity	NPC611966
0.5408	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 NPC249875 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	2934
0.1-0.2	6028
0.2-0.3	155
0.3-0.4	9
0.4-0.5	4
0.5-0.6	10
0.6-0.7	7
0.7-0.8	2
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8454	Intermediate Similarity	NPD7781	Phase 4
0.7885	Intermediate Similarity	NPD7780	Approved
0.7115	Intermediate Similarity	NPD7717	Phase 4
0.6789	Remote Similarity	NPD7716	Approved
0.6415	Remote Similarity	NPD7731	Pre-clinical
0.6129	Remote Similarity	NPD3506	Phase 4
0.6126	Remote Similarity	NPD7730	Approved
0.6126	Remote Similarity	NPD7790	Approved
0.6126	Remote Similarity	NPD7791	Phase 4
0.6	Remote Similarity	NPD4079	Phase 4
0.5862	Remote Similarity	NPD7789	Approved
0.5758	Remote Similarity	NPD3505	Approved
0.5644	Remote Similarity	NPD4076	Approved
0.5526	Remote Similarity	NPD7824	Approved
0.5484	Remote Similarity	NPD7951	Phase 4
0.5478	Remote Similarity	NPD7271	Approved
0.5431	Remote Similarity	NPD7952	Approved
0.5431	Remote Similarity	NPD7953	Pre-clinical
0.5319	Remote Similarity	NPD4075	Phase 2
0.5271	Remote Similarity	NPD7950	Approved

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