NPASS Compound

Natural Product: NPC143895

Natural Product ID	NPC143895
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Dihydroclusin Diacetate
IUPAC Name	[(2R,3R)-3-(acetyloxymethyl)-2-(1,3-benzodioxol-5-ylmethyl)-4-(3,4,5-trimethoxyphenyl)butyl] acetate
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL3582088
PubChem CID	21600064
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0001392] Lignans, neolignans and related compounds [CHEMONTID:0001969] Dibenzylbutane lignans

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 67 69 0 0 0 0 0 0 0 0999 V2000 -3.7966 -1.7687 -3.0171 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4828 -0.8817 -2.1738 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.9553 -0.5166 -0.9647 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7180 -1.0201 -0.5674 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2187 -0.6476 0.6350 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9365 -1.0795 1.1601 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1899 -0.0282 1.0193 C 0 0 2 0 0 0 0 0 0 0 0 0 0.4977 0.3235 -0.3800 C 0 0 1 0 0 0 0 0 0 0 0 0 1.4703 1.3986 -0.6648 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8469 1.3255 -0.1868 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8364 0.5877 -0.8010 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1633 0.5879 -0.3665 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5443 1.3425 0.7171 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5833 2.0920 1.3548 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2810 2.0834 0.9179 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2476 2.7434 2.3996 O 0 0 0 0 0 0 0 0 0 0 0 0 6.6440 2.7458 2.1674 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7609 1.5522 1.3818 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8110 -0.9101 -1.2459 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0871 -0.5875 -2.5677 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3034 0.0667 -3.4665 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8317 0.4536 -3.0972 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6967 0.3604 -4.8705 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3196 -0.5814 1.8613 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7038 -1.8294 1.3548 O 0 0 0 0 0 0 0 0 0 0 0 0 2.7035 -2.6163 1.8774 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3194 -2.1879 2.8824 O 0 0 0 0 0 0 0 0 0 0 0 0 2.9878 -3.9117 1.2243 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9578 0.2286 1.4390 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1791 0.7379 1.0677 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6649 0.3446 -0.1582 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8970 0.8425 -0.5625 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.0993 0.1475 -0.2456 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9221 1.6069 1.8536 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3505 1.9681 3.1123 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3175 -1.7360 -4.0055 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7959 -2.8052 -2.6118 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7625 -1.4409 -3.1726 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2118 -1.6980 -1.2328 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0356 -1.1889 2.2817 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5934 -2.0773 0.8191 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2231 0.8938 1.5112 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4986 0.6741 -0.8245 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4556 1.6260 -1.7939 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9682 2.3624 -0.2829 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5548 -0.0138 -1.6668 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9222 0.0024 -0.8621 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5177 2.6671 1.4095 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2241 2.6737 3.1016 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9411 3.6136 1.5398 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0489 -1.6553 -1.0472 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7784 -1.3723 -0.8554 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7900 0.1761 -5.0327 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1691 -0.3311 -5.5592 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4598 1.3904 -5.1728 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7927 -0.8574 2.8565 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1023 0.0766 2.1516 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6330 -4.5606 1.8567 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4594 -3.6900 0.2499 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0216 -4.4114 1.0186 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5805 0.5429 2.4081 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4330 0.3796 0.7871 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9016 -0.9434 -0.3025 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.8501 0.4783 -1.0111 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0805 2.6041 3.6409 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1156 1.0775 3.7294 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4270 2.5703 2.9829 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 1 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 2 0 13 14 1 0 14 15 2 0 14 16 1 0 16 17 1 0 17 18 1 0 8 19 1 0 19 20 1 0 20 21 1 0 21 22 2 0 21 23 1 0 7 24 1 0 24 25 1 0 25 26 1 0 26 27 2 0 26 28 1 0 5 29 2 0 29 30 1 0 30 31 2 0 31 32 1 0 32 33 1 0 30 34 1 0 34 35 1 0 31 3 1 0 15 10 1 0 18 13 1 0 1 36 1 0 1 37 1 0 1 38 1 0 4 39 1 0 6 40 1 0 6 41 1 0 7 42 1 1 8 43 1 6 9 44 1 0 9 45 1 0 11 46 1 0 12 47 1 0 15 48 1 0 17 49 1 0 17 50 1 0 19 51 1 0 19 52 1 0 23 53 1 0 23 54 1 0 23 55 1 0 24 56 1 0 24 57 1 0 28 58 1 0 28 59 1 0 28 60 1 0 29 61 1 0 33 62 1 0 33 63 1 0 33 64 1 0 35 65 1 0 35 66 1 0 35 67 1 0 M END

Standard InCHIKey	PGLVKIQODAEYPR-SFTDATJTSA-N
Standard InCHI	InChI=1S/C26H32O9/c1-16(27)32-13-20(8-18-6-7-22-23(10-18)35-15-34-22)21(14-33-17(2)28)9-19-11-24(29-3)26(31-5)25(12-19)30-4/h6-7,10-12,20-21H,8-9,13-15H2,1-5H3/t20-,21-/m0/s1
SMILES	COc1cc(C[C@H]([C@@H](Cc2ccc3c(c2)OCO3)COC(=O)C)COC(=O)C)cc(c1OC)OC

Calculated Properties

Physi-Chem Properties

Molecular Weight:	488.2	Volume:	490.603 ? Van der Waals volume.
Dense:	0.995	LogP:	2.686 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.878 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.756 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	14.0	Rigid Bonds:	18.0
TPSA:	98.75 ? Topological Polar Surface Area.	H-Bond Acceptor:	9.0
H-Bond Donor:	0.0	Rings:	3.0
Heavy Atoms:	9.0

MedChem Properties

QED Drug-Likeness Score:	0.415	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	3.374	Fsp³:	0.462
MCE-18:	61.053 ? 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:	0	PAINS Alert:	0
Colloidal aggregators:	0.225	Fluc inhibitor:	0.008 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.021 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.277 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.303	Promiscuous compounds:	0.128

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.806	MDCK Permeability:	-4.686
Pgp-inhibitor:	0.959	Pgp-substrate:	0.014
PAMPA:	0.02 ? 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):	0.0
20% Bioavailability (F20%):	0.037	30% Bioavailability (F30%):	0.021
50% Bioavailability (F50%):	0.76

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.187	MRP1:	0.969
Plasma Protein Binding (PPB):	95.689%	Volume Distribution (VD):	-0.243
Fu:	5.83% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.998
OATP1B3 inhibitor:	0.991	BCRP inhibitor:	0.212
BSEP inhibitor:	1.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.002	CYP1A2-substrate:	0.456
CYP2C19-inhibitor:	0.987	CYP2C19-substrate:	0.28
CYP2C9-inhibitor:	0.022	CYP2C9-substrate:	0.961
CYP2D6-inhibitor:	0.008	CYP2D6-substrate:	1.0
CYP3A4-inhibitor:	0.994	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.061	CYP2C8-inhibitor:	0.553
HLM stability:	0.442 ? 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):

2.754

Half-life (T1/2):

0.967

ADMET: Toxicity

hERG Blockers:	0.165	hERG Blockers (10um):	0.367
Human Hepatotoxicity (H-HT):	0.718	Drug-induced Liver Injury (DILI):	0.752
AMES Toxicity:	0.862	Rat Oral Acute Toxicity:	0.118
Maximum Recommended Daily Dose:	0.126	Skin Sensitization:	0.927
Carcinogencity:	0.634	Eye Corrosion:	0.001
Eye Irritation:	0.405	Respiratory Toxicity:	0.023
Drug-induced Neurotoxicity:	0.627	Ototoxicity:	0.681
Hematotoxicity:	0.5	Drug-induced Nephrotoxicity:	0.739
Genotoxicity:	0.901	RPMI-8226 Immunitoxicity:	0.077
A549 Cytotoxicity:	0.053	Hek293 Cytotoxicity:	0.16
BCF:	0.927 ? 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:	3.924 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.54 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.959 ? 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
NPO3925	Bursera microphylla	Species	Burseraceae	Eukaryota	Resin	Baha de Kino	2013-JAN	PMID[25966052]
NPO12785	Bursera fagaroides	Species	Burseraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3925	Bursera microphylla	Species	Burseraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3925	Bursera microphylla	Species	Burseraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12785	Bursera fagaroides	Species	Burseraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3925	Bursera microphylla	Species	Burseraceae	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

Activity Type	# Activity
IC50	2

Activity Type	# Activity
Cell line	1
Non-molecular	1

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
NPT113	Cell line	RAW264.7	Mus musculus	IC50	=	200.0	nM	PMID[25966052]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	IC50	=	2500.0	nM	PMID[25966052]

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 NPC143895 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	18904
0.1-0.2	27541
0.2-0.3	2692
0.3-0.4	514
0.4-0.5	141
0.5-0.6	35
0.6-0.7	17
0.7-0.8	0
0.8-0.85	4
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8605	High Similarity	NPC476748
0.8261	Intermediate Similarity	NPC192255
0.8222	Intermediate Similarity	NPC11453
0.8	Intermediate Similarity	NPC176586
0.8	Intermediate Similarity	NPC210354
0.75	Intermediate Similarity	NPC191158
0.75	Intermediate Similarity	NPC177644
0.6957	Remote Similarity	NPC600801
0.6923	Remote Similarity	NPC205915
0.6852	Remote Similarity	NPC185908
0.6852	Remote Similarity	NPC482891
0.6842	Remote Similarity	NPC56184
0.68	Remote Similarity	NPC110958
0.68	Remote Similarity	NPC19890
0.6552	Remote Similarity	NPC487679
0.6552	Remote Similarity	NPC487678
0.6538	Remote Similarity	NPC40237
0.6471	Remote Similarity	NPC474288
0.64	Remote Similarity	NPC196937
0.6379	Remote Similarity	NPC145569
0.6346	Remote Similarity	NPC92693
0.6346	Remote Similarity	NPC211386
0.6226	Remote Similarity	NPC158737
0.6042	Remote Similarity	NPC344161
0.5902	Remote Similarity	NPC282291
0.5902	Remote Similarity	NPC166137
0.587	Remote Similarity	NPC80241
0.587	Remote Similarity	NPC301641
0.587	Remote Similarity	NPC485483
0.58	Remote Similarity	NPC72796
0.5745	Remote Similarity	NPC81067
0.5745	Remote Similarity	NPC602945
0.5741	Remote Similarity	NPC171550
0.5741	Remote Similarity	NPC134764
0.5577	Remote Similarity	NPC223807
0.5556	Remote Similarity	NPC216223
0.5536	Remote Similarity	NPC165128
0.5517	Remote Similarity	NPC18576
0.55	Remote Similarity	NPC293757
0.55	Remote Similarity	NPC668
0.5424	Remote Similarity	NPC47181
0.5424	Remote Similarity	NPC230968
0.5424	Remote Similarity	NPC102260
0.5417	Remote Similarity	NPC477886
0.5357	Remote Similarity	NPC283949
0.5333	Remote Similarity	NPC3982
0.5273	Remote Similarity	NPC189474
0.5254	Remote Similarity	NPC226547
0.5238	Remote Similarity	NPC76687
0.52	Remote Similarity	NPC40352
0.52	Remote Similarity	NPC213711
0.5161	Remote Similarity	NPC474158
0.5156	Remote Similarity	NPC169973
0.5088	Remote Similarity	NPC274356
0.5088	Remote Similarity	NPC101748
0.5082	Remote Similarity	NPC106920
0.5082	Remote Similarity	NPC15811
0.5077	Remote Similarity	NPC136757
0.5077	Remote Similarity	NPC174512

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC143895 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3763
0.1-0.2	5034
0.2-0.3	330
0.3-0.4	20
0.4-0.5	3
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