NPASS Compound

Natural Product: NPC82182

Natural Product ID	NPC82182
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	IVYAOUHUAWZJDB-UZOBGTHZSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	44255238
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0002049] Terpene glycosides [CHEMONTID:0004081] Iridoid O-glycosides

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 68 71 0 0 0 0 0 0 0 0999 V2000 8.6185 -1.5164 -2.9429 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3980 -1.3356 -2.2435 O 0 0 0 0 0 0 0 0 0 0 0 0 6.3337 -0.6874 -2.8618 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5232 -0.2848 -4.0480 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0511 -0.4792 -2.1707 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0890 0.1452 -2.8106 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8901 0.3562 -2.2057 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6213 0.0099 -0.8349 C 0 0 2 0 0 0 0 0 0 0 0 0 3.4533 -1.1274 -0.3852 C 0 0 2 0 0 0 0 0 0 0 0 0 3.5967 -1.1421 1.0907 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7366 -0.5494 1.4503 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4951 -0.0675 0.2552 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9081 -0.9759 -0.8101 C 0 0 2 0 0 0 0 0 0 0 0 0 2.6284 -1.7557 2.0402 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1020 -1.6122 3.3636 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2480 -0.2022 -0.8047 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5868 0.8470 -0.1882 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.4011 1.5190 -1.1183 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.0989 2.5938 -0.3693 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.7868 2.7206 1.0775 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.4431 1.4545 1.7722 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.4688 1.0717 2.8039 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7055 0.6580 2.2505 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.7006 0.2809 3.1220 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5523 0.2906 4.3662 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0038 -0.1569 2.5752 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2266 -0.1851 1.2783 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4889 -0.6080 0.6986 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.5734 -1.0338 1.4134 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.7620 -1.4257 0.8183 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.9059 -1.4032 -0.5483 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.8120 -0.9722 -1.2978 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6324 -0.5839 -0.6926 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.0512 -1.7759 -1.2260 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1229 0.4153 0.9033 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2010 3.7037 1.3231 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4964 2.5486 -0.5943 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2158 1.9871 -2.2755 O 0 0 0 0 0 0 0 0 0 0 0 0 8.4613 -1.4872 -4.0408 H 0 0 0 0 0 0 0 0 0 0 0 0 9.3467 -0.7124 -2.6395 H 0 0 0 0 0 0 0 0 0 0 0 0 9.1203 -2.4672 -2.6855 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2523 0.4918 -3.8234 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8197 0.9545 -0.2889 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0536 -2.1111 -0.6941 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0538 -0.4425 2.4776 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3066 0.9980 0.0419 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5874 -0.2106 0.3754 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3868 -1.9592 -0.7157 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6347 -1.2891 2.0085 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4885 -2.8491 1.8146 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6138 -2.4249 3.6325 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3239 1.6093 0.1480 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1667 0.7258 -1.3604 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7997 3.5775 -0.8455 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7127 3.1387 1.5754 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5022 1.6292 2.3649 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6128 1.9527 3.4855 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0696 0.2707 3.4876 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7897 -0.4599 3.2541 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3892 0.1352 0.6395 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5178 -1.0741 2.4868 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.6128 -1.7618 1.4266 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.9152 -0.9498 -2.3744 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7899 -0.2507 -1.2658 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.9802 -2.1733 -2.1441 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5253 3.5039 2.2435 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7643 1.6376 -0.3132 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1795 1.2764 -2.9671 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 3 5 1 0 5 6 2 0 6 7 1 0 7 8 1 0 8 9 1 0 9 10 1 0 10 11 2 0 11 12 1 0 12 13 1 0 10 14 1 0 14 15 1 0 8 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 0 22 23 1 0 23 24 1 0 24 25 2 0 24 26 1 0 26 27 2 0 27 28 1 0 28 29 2 0 29 30 1 0 30 31 2 0 31 32 1 0 32 33 2 0 31 34 1 0 21 35 1 0 20 36 1 0 19 37 1 0 18 38 1 0 13 5 1 0 35 17 1 0 13 9 1 0 33 28 1 0 1 39 1 0 1 40 1 0 1 41 1 0 6 42 1 0 8 43 1 1 9 44 1 6 11 45 1 0 12 46 1 0 12 47 1 0 13 48 1 6 14 49 1 0 14 50 1 0 15 51 1 0 17 52 1 1 18 53 1 6 19 54 1 6 20 55 1 1 21 56 1 1 22 57 1 0 22 58 1 0 26 59 1 0 27 60 1 0 29 61 1 0 30 62 1 0 32 63 1 0 33 64 1 0 34 65 1 0 36 66 1 0 37 67 1 0 38 68 1 0 M END

Standard InCHIKey	IVYAOUHUAWZJDB-UZOBGTHZSA-N
Standard InCHI	InChI=1S/C26H30O12/c1-34-24(33)17-11-36-25(20-14(10-27)5-8-16(17)20)38-26-23(32)22(31)21(30)18(37-26)12-35-19(29)9-4-13-2-6-15(28)7-3-13/h2-7,9,11,16,18,20-23,25-28,30-32H,8,10,12H2,1H3/b9-4+/t16-,18-,20-,21-,22+,23-,25+,26+/m1/s1
SMILES	COC(=O)C1=CO[C@H]([C@@H]2C(=CC[C@H]12)CO)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](COC(=O)/C=C/c2ccc(cc2)O)O1)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	534.17	Volume:	508.417 ? Van der Waals volume.
Dense:	1.051	LogP:	1.386 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.741 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.984 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	10.0	Rigid Bonds:	25.0
TPSA:	181.44 ? Topological Polar Surface Area.	H-Bond Acceptor:	12.0
H-Bond Donor:	5.0	Rings:	4.0
Heavy Atoms:	12.0

MedChem Properties

QED Drug-Likeness Score:	0.168	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.68	Fsp³:	0.462
MCE-18:	90.316 ? 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:	0.821	Fluc inhibitor:	0.639 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.154 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.549 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.134	Promiscuous compounds:	0.264

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.805	MDCK Permeability:	-5.237
Pgp-inhibitor:	0.003	Pgp-substrate:	0.029
PAMPA:	0.984 ? 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):	0.367
20% Bioavailability (F20%):	0.946	30% Bioavailability (F30%):	0.999
50% Bioavailability (F50%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.002	MRP1:	0.067
Plasma Protein Binding (PPB):	79.713%	Volume Distribution (VD):	-0.4
Fu:	20.354% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.997
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.001
BSEP inhibitor:	0.439

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.003
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.002
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.036
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.01
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.999
HLM stability:	0.13 ? 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):

2.835

Half-life (T1/2):

2.716

ADMET: Toxicity

hERG Blockers:	0.056	hERG Blockers (10um):	0.241
Human Hepatotoxicity (H-HT):	0.533	Drug-induced Liver Injury (DILI):	0.943
AMES Toxicity:	0.944	Rat Oral Acute Toxicity:	0.031
Maximum Recommended Daily Dose:	0.139	Skin Sensitization:	0.999
Carcinogencity:	0.299	Eye Corrosion:	0.0
Eye Irritation:	0.032	Respiratory Toxicity:	0.005
Drug-induced Neurotoxicity:	0.044	Ototoxicity:	0.951
Hematotoxicity:	0.307	Drug-induced Nephrotoxicity:	0.808
Genotoxicity:	0.613	RPMI-8226 Immunitoxicity:	0.119
A549 Cytotoxicity:	0.287	Hek293 Cytotoxicity:	0.599
BCF:	0.607 ? 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:	3.362 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.129 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.449 ? 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
NPO9518	Gardenia jasminoides	Species	Rubiaceae	Eukaryota	Fruits	n.a.	n.a.	PMID[16309325]
NPO9518	Gardenia jasminoides	Species	Rubiaceae	Eukaryota	n.a.	Seoul, Korea	2000-Jun	PMID[16643034]
NPO9518	Gardenia jasminoides	Species	Rubiaceae	Eukaryota	fruit	n.a.	n.a.	PMID[18505286]
NPO9518	Gardenia jasminoides	Species	Rubiaceae	Eukaryota	fruit	n.a.	n.a.	PMID[19650637]
NPO9518	Gardenia jasminoides	Species	Rubiaceae	Eukaryota	fruits	n.a.	n.a.	PMID[23305920]
NPO9518	Gardenia jasminoides	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32141747]
NPO9518	Gardenia jasminoides	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9518	Gardenia jasminoides	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9518	Gardenia jasminoides	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9518	Gardenia jasminoides	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO9518	Gardenia jasminoides	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO9518	Gardenia jasminoides	Species	Rubiaceae	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 NPC82182 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	11010
0.1-0.2	34509
0.2-0.3	3618
0.3-0.4	543
0.4-0.5	134
0.5-0.6	30
0.6-0.7	9
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
0.878	High Similarity	NPC69367
0.8118	Intermediate Similarity	NPC611523
0.6585	Remote Similarity	NPC267869
0.6463	Remote Similarity	NPC197541
0.6463	Remote Similarity	NPC118761
0.6444	Remote Similarity	NPC202391
0.6444	Remote Similarity	NPC296659
0.6386	Remote Similarity	NPC284929
0.6235	Remote Similarity	NPC86095
0.6154	Remote Similarity	NPC31745
0.6154	Remote Similarity	NPC220936
0.5949	Remote Similarity	NPC255677
0.5949	Remote Similarity	NPC22149
0.5949	Remote Similarity	NPC306344
0.5714	Remote Similarity	NPC479473
0.5714	Remote Similarity	NPC275721
0.5714	Remote Similarity	NPC479468
0.5714	Remote Similarity	NPC479474
0.5532	Remote Similarity	NPC96599
0.5529	Remote Similarity	NPC288416
0.5412	Remote Similarity	NPC470572
0.5408	Remote Similarity	NPC240592
0.5408	Remote Similarity	NPC117346
0.5354	Remote Similarity	NPC203664
0.5341	Remote Similarity	NPC234304
0.5333	Remote Similarity	NPC252114
0.53	Remote Similarity	NPC63304
0.5287	Remote Similarity	NPC229784
0.5281	Remote Similarity	NPC34293
0.52	Remote Similarity	NPC474268
0.52	Remote Similarity	NPC119773
0.5161	Remote Similarity	NPC281798
0.5152	Remote Similarity	NPC300262
0.5104	Remote Similarity	NPC254819
0.5057	Remote Similarity	NPC222062
0.5052	Remote Similarity	NPC237872
0.5052	Remote Similarity	NPC475213
0.5052	Remote Similarity	NPC152796
0.5052	Remote Similarity	NPC302286
0.5052	Remote Similarity	NPC116104
0.5052	Remote Similarity	NPC175333

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC82182 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4887
0.1-0.2	4214
0.2-0.3	47
0.3-0.4	1
0.4-0.5	1
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