NPASS Compound

Natural Product: NPC209766

Natural Product ID	NPC209766
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	GRYWSROVPQJCDJ-DODNOZFWSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	101688472
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001111] Flavonoid glycosides [CHEMONTID:0001583] Flavonoid O-glycosides [CHEMONTID:0003533] Flavonoid-7-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 58 61 0 0 0 0 0 0 0 0999 V2000 5.3048 1.7627 -3.2643 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4931 1.2383 -2.7048 O 0 0 0 0 0 0 0 0 0 0 0 0 6.3902 0.4623 -1.5640 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1533 0.1966 -0.9751 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0568 -0.5819 0.1695 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2190 -1.0850 0.7068 C 0 0 0 0 0 0 0 0 0 0 0 0 7.4684 -0.8249 0.1235 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5439 -0.0515 -1.0102 C 0 0 0 0 0 0 0 0 0 0 0 0 8.7516 0.2358 -1.6252 O 0 0 0 0 0 0 0 0 0 0 0 0 3.7505 -0.8431 0.7601 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5754 -1.5844 1.9049 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3151 -1.8141 2.4411 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1097 -2.4843 3.4831 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2376 -1.2717 1.7844 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0612 -1.4508 2.2438 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1070 -0.8882 1.5466 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9500 -0.1434 0.4004 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3800 0.0180 -0.0371 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4493 -0.5367 0.6435 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6799 -0.3488 0.1752 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.9298 0.4498 -0.3480 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2991 0.3870 -0.0967 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.8395 1.6525 0.5188 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.3483 1.7154 0.4699 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.6705 1.6415 -1.0269 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.2149 0.2670 -1.4410 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.5691 0.0216 -2.9079 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3212 -1.3385 -3.1608 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.9278 -0.0239 -1.2308 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.0297 1.7663 -1.2735 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.8225 2.8488 1.0647 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4940 1.7438 1.8763 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2078 -2.1842 3.3813 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4318 -2.4915 3.9859 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5400 2.4274 -4.1283 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7129 2.3508 -2.5411 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6310 0.9745 -3.6795 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2469 0.6046 -1.4215 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1858 -1.6879 1.5871 H 0 0 0 0 0 0 0 0 0 0 0 0 8.3764 -1.2372 0.5685 H 0 0 0 0 0 0 0 0 0 0 0 0 9.5284 0.4891 -1.0137 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4111 -2.0095 2.4219 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1148 -1.0152 1.8965 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5649 0.5890 -0.9247 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4709 -0.3824 0.6789 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4464 2.5242 -0.0191 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7565 0.7733 0.8926 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0578 2.3951 -1.5319 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8552 -0.4574 -0.8732 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6804 0.1365 -3.0268 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0060 0.6519 -3.5959 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7436 -1.7222 -2.4540 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5158 1.6824 -0.4116 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2757 2.6694 1.9386 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5178 1.6204 1.9170 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6420 -1.8726 4.8846 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4703 -3.5702 4.3184 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2983 -2.3945 3.3056 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 4 5 1 0 5 6 2 0 6 7 1 0 7 8 2 0 8 9 1 0 5 10 1 0 10 11 2 0 11 12 1 0 12 13 2 0 12 14 1 0 14 15 2 0 15 16 1 0 16 17 2 0 17 18 1 0 18 19 2 0 19 20 1 0 17 21 1 0 21 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 26 27 1 0 27 28 1 0 26 29 1 0 25 30 1 0 24 31 1 0 23 32 1 0 15 33 1 0 33 34 1 0 8 3 1 0 20 10 1 0 29 22 1 0 19 14 1 0 1 35 1 0 1 36 1 0 1 37 1 0 4 38 1 0 6 39 1 0 7 40 1 0 9 41 1 0 11 42 1 0 16 43 1 0 18 44 1 0 22 45 1 1 23 46 1 6 24 47 1 1 25 48 1 6 26 49 1 1 27 50 1 0 27 51 1 0 28 52 1 0 30 53 1 0 31 54 1 0 32 55 1 0 34 56 1 0 34 57 1 0 34 58 1 0 M END

Standard InCHIKey	GRYWSROVPQJCDJ-DODNOZFWSA-N
Standard InCHI	InChI=1S/C23H24O11/c1-30-15-5-10(3-4-12(15)25)14-8-13(26)19-16(31-2)6-11(7-17(19)33-14)32-23-22(29)21(28)20(27)18(9-24)34-23/h3-8,18,20-25,27-29H,9H2,1-2H3/t18-,20-,21+,22-,23-/m1/s1
SMILES	COc1cc(ccc1O)c1cc(=O)c2c(cc(cc2o1)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O)OC

Calculated Properties

Physi-Chem Properties

Molecular Weight:	476.13	Volume:	447.739 ? Van der Waals volume.
Dense:	1.063	LogP:	1.069 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.512 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.479 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	6.0	Rigid Bonds:	24.0
TPSA:	168.28 ? Topological Polar Surface Area.	H-Bond Acceptor:	11.0
H-Bond Donor:	5.0	Rings:	4.0
Heavy Atoms:	11.0

MedChem Properties

QED Drug-Likeness Score:	0.333	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	3.841	Fsp³:	0.348
MCE-18:	86.387 ? 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:	Rejected	BMS Rule:	0
Chelating Alert:	1	PAINS Alert:	0
Colloidal aggregators:	0.619	Fluc inhibitor:	0.282 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.971 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.874 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.09	Promiscuous compounds:	0.423

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.986	MDCK Permeability:	-5.187
Pgp-inhibitor:	0.004	Pgp-substrate:	0.241
PAMPA:	0.818 ? 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):	0.53
20% Bioavailability (F20%):	0.171	30% Bioavailability (F30%):	0.901
50% Bioavailability (F50%):	0.986

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.522
Plasma Protein Binding (PPB):	81.913%	Volume Distribution (VD):	-0.091
Fu:	17.226% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.979
BSEP inhibitor:	0.262

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.001
CYP2C19-inhibitor:	0.001	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.004	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.088	CYP2D6-substrate:	0.025
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.008
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.396
HLM stability:	0.004 ? 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):

3.153

Half-life (T1/2):

3.691

ADMET: Toxicity

hERG Blockers:	0.028	hERG Blockers (10um):	0.113
Human Hepatotoxicity (H-HT):	0.613	Drug-induced Liver Injury (DILI):	0.957
AMES Toxicity:	0.902	Rat Oral Acute Toxicity:	0.037
Maximum Recommended Daily Dose:	0.068	Skin Sensitization:	0.986
Carcinogencity:	0.468	Eye Corrosion:	0.0
Eye Irritation:	0.376	Respiratory Toxicity:	0.036
Drug-induced Neurotoxicity:	0.01	Ototoxicity:	0.811
Hematotoxicity:	0.32	Drug-induced Nephrotoxicity:	0.573
Genotoxicity:	0.853	RPMI-8226 Immunitoxicity:	0.118
A549 Cytotoxicity:	0.231	Hek293 Cytotoxicity:	0.394
BCF:	0.408 ? 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:	3.011 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.295 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.599 ? 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
NPO18758	Carapa grandiflora	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17607	Jatropha grossidentata	Species	Euphorbiaceae	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 NPC209766 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	24482
0.1-0.2	21353
0.2-0.3	2726
0.3-0.4	934
0.4-0.5	259
0.5-0.6	69
0.6-0.7	24
0.7-0.8	0
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8378	Intermediate Similarity	NPC610763
0.7722	Intermediate Similarity	NPC311830
0.7375	Intermediate Similarity	NPC284960
0.7342	Intermediate Similarity	NPC182045
0.7284	Intermediate Similarity	NPC602805
0.7179	Intermediate Similarity	NPC110349
0.716	Intermediate Similarity	NPC601144
0.6588	Remote Similarity	NPC479407
0.6548	Remote Similarity	NPC601710
0.6506	Remote Similarity	NPC222936
0.6353	Remote Similarity	NPC606560
0.6341	Remote Similarity	NPC83283
0.6265	Remote Similarity	NPC168822
0.6265	Remote Similarity	NPC189142
0.6265	Remote Similarity	NPC77660
0.6222	Remote Similarity	NPC473512
0.6207	Remote Similarity	NPC601586
0.619	Remote Similarity	NPC45638
0.6163	Remote Similarity	NPC22832
0.6163	Remote Similarity	NPC243930
0.6145	Remote Similarity	NPC39360
0.6145	Remote Similarity	NPC29763
0.6145	Remote Similarity	NPC210003
0.6118	Remote Similarity	NPC201292
0.6092	Remote Similarity	NPC607707
0.6071	Remote Similarity	NPC93337
0.6071	Remote Similarity	NPC95090
0.6071	Remote Similarity	NPC27408
0.6023	Remote Similarity	NPC488072
0.6	Remote Similarity	NPC58716
0.6	Remote Similarity	NPC105025
0.5977	Remote Similarity	NPC101026
0.5977	Remote Similarity	NPC488077
0.5952	Remote Similarity	NPC58053
0.5909	Remote Similarity	NPC206123
0.5882	Remote Similarity	NPC146792
0.587	Remote Similarity	NPC129827
0.5862	Remote Similarity	NPC609451
0.5843	Remote Similarity	NPC203050
0.5843	Remote Similarity	NPC469931
0.5843	Remote Similarity	NPC225434
0.5833	Remote Similarity	NPC195257
0.5814	Remote Similarity	NPC186807
0.5795	Remote Similarity	NPC605067
0.5747	Remote Similarity	NPC100720
0.5745	Remote Similarity	NPC475366
0.5745	Remote Similarity	NPC475497
0.5652	Remote Similarity	NPC473657
0.5632	Remote Similarity	NPC84362
0.5584	Remote Similarity	NPC606105
0.5581	Remote Similarity	NPC261866
0.5581	Remote Similarity	NPC45618
0.5556	Remote Similarity	NPC88023
0.5556	Remote Similarity	NPC479406
0.5556	Remote Similarity	NPC309025
0.5506	Remote Similarity	NPC479402
0.5465	Remote Similarity	NPC183357
0.5444	Remote Similarity	NPC197285
0.5435	Remote Similarity	NPC4390
0.5417	Remote Similarity	NPC284277
0.5402	Remote Similarity	NPC143851
0.5393	Remote Similarity	NPC599850
0.5341	Remote Similarity	NPC277205
0.5341	Remote Similarity	NPC37919
0.5341	Remote Similarity	NPC136042
0.5341	Remote Similarity	NPC259152
0.5333	Remote Similarity	NPC191306
0.5319	Remote Similarity	NPC295613
0.5275	Remote Similarity	NPC486578
0.5263	Remote Similarity	NPC15358
0.5256	Remote Similarity	NPC179126
0.5227	Remote Similarity	NPC19709
0.5222	Remote Similarity	NPC42773
0.5222	Remote Similarity	NPC45522
0.5222	Remote Similarity	NPC117260
0.5217	Remote Similarity	NPC111249
0.5208	Remote Similarity	NPC607513
0.519	Remote Similarity	NPC137062
0.5169	Remote Similarity	NPC297987
0.5169	Remote Similarity	NPC323593
0.5169	Remote Similarity	NPC203500
0.5169	Remote Similarity	NPC609879
0.5165	Remote Similarity	NPC488071
0.5161	Remote Similarity	NPC48773
0.5128	Remote Similarity	NPC20830
0.5125	Remote Similarity	NPC473045
0.5114	Remote Similarity	NPC331652
0.5111	Remote Similarity	NPC22195
0.5111	Remote Similarity	NPC245014
0.5111	Remote Similarity	NPC24043
0.5111	Remote Similarity	NPC21190
0.5111	Remote Similarity	NPC488080
0.5111	Remote Similarity	NPC169977
0.5111	Remote Similarity	NPC603655
0.5055	Remote Similarity	NPC475942
0.5055	Remote Similarity	NPC27942
0.5054	Remote Similarity	NPC150442
0.5054	Remote Similarity	NPC605784
0.5053	Remote Similarity	NPC8856
0.5052	Remote Similarity	NPC3583

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC209766 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5687
0.1-0.2	3386
0.2-0.3	60
0.3-0.4	12
0.4-0.5	4
0.5-0.6	1
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
0.56	Remote Similarity	NPD7472	Pre-clinical

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