NPASS Compound

Natural Product: NPC474347

Natural Product ID	NPC474347
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Kadangustin F
IUPAC Name	n.a.
Synonyms	Kadangustin F
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL465516
PubChem CID	24862695
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000238] Tannins [CHEMONTID:0001710] Hydrolyzable tannins

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 80 0 0 0 0 0 0 0 0999 V2000 2.6472 2.7723 2.3696 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1115 2.9043 2.1446 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7603 2.0854 1.3448 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0888 1.0075 0.6362 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6797 0.2170 -0.1288 O 0 0 0 0 0 0 0 0 0 0 0 0 2.7522 0.7343 0.7208 O 0 0 0 0 0 0 0 0 0 0 0 0 2.0260 -0.2476 0.0966 C 0 0 1 0 0 0 0 0 0 0 0 0 1.4773 -1.3525 0.9601 C 0 0 1 0 0 0 0 0 0 0 0 0 0.7347 -0.8887 2.1544 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7959 -2.4134 0.1939 C 0 0 1 0 0 0 0 0 0 0 0 0 1.5798 -3.7251 0.1064 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6070 -2.7972 0.5642 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.0659 -3.7649 -0.3946 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5570 -5.0002 -0.0401 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6118 -5.3087 1.1818 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.0351 -6.0126 -1.0102 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5228 -1.6249 0.4770 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3799 -0.3554 -0.1514 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3540 0.2140 -1.0091 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0451 0.2913 -0.8812 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6996 0.9693 -1.8642 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0194 1.5477 -2.9288 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6843 2.2382 -3.9246 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0896 2.3459 -3.8372 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3763 1.4359 -3.0076 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0757 0.7585 -2.0387 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4372 0.5738 -2.0375 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0944 1.9982 -4.0539 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6013 3.3262 -3.9892 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3269 0.6291 -0.0761 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0702 1.8348 -0.7033 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4222 2.9169 -0.0572 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4626 0.3416 0.6404 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6511 -0.8934 1.2724 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6575 -1.8459 1.1667 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8185 -1.1215 1.9788 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.9730 -2.3820 2.6034 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4593 1.2993 0.7460 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.5315 2.2627 1.7625 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2209 2.2581 1.1525 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3205 3.6772 2.9576 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0963 2.8680 1.4004 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3962 1.8370 2.9108 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6959 3.6920 2.6413 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7899 -0.7844 -0.5525 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4132 -1.8650 1.3783 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3700 -0.8346 3.0794 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3313 0.1463 2.0938 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0429 -1.6272 2.4186 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7299 -2.0821 -0.8886 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6567 -3.5465 0.0568 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2226 -4.2774 -0.7959 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2632 -4.3329 0.9786 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7435 -3.2643 1.5363 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4364 -6.9347 -0.8409 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0870 -6.2816 -0.7552 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9410 -5.6606 -2.0549 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7552 1.0748 -1.8433 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6024 1.3778 -3.9660 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4917 3.0639 -4.6014 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4154 2.7514 -2.8498 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8792 -0.3032 -2.2931 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3593 3.8705 -4.9134 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7169 3.3189 -3.8628 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1823 3.8576 -3.1101 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3387 2.9743 -0.3147 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8551 3.8896 -0.3679 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5183 2.7857 1.0539 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7801 -2.8066 1.6488 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7628 -3.2163 1.8925 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2630 -2.5133 3.4641 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9837 -2.5404 3.0012 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3794 1.8499 2.7772 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8410 3.1084 1.5657 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5879 2.6548 1.7512 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8013 1.3692 1.4911 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5919 3.1261 1.7240 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4336 2.3499 0.0496 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 2 0 3 4 1 0 4 5 2 0 4 6 1 0 6 7 1 0 7 8 1 0 8 9 1 0 8 10 1 0 10 11 1 0 10 12 1 0 12 13 1 0 13 14 1 0 14 15 2 0 14 16 1 0 12 17 1 0 17 18 2 0 18 19 1 0 19 20 2 0 20 21 1 0 21 22 2 0 22 23 1 0 23 24 1 0 22 25 1 0 25 26 2 0 26 27 1 0 25 28 1 0 28 29 1 0 18 30 1 0 30 31 1 0 31 32 1 0 30 33 2 0 33 34 1 0 34 35 2 0 34 36 1 0 36 37 1 0 33 38 1 0 38 39 1 0 3 40 1 0 20 7 1 0 35 17 1 0 26 19 1 0 1 41 1 0 1 42 1 0 1 43 1 0 2 44 1 0 7 45 1 6 8 46 1 1 9 47 1 0 9 48 1 0 9 49 1 0 10 50 1 6 11 51 1 0 11 52 1 0 11 53 1 0 12 54 1 1 16 55 1 0 16 56 1 0 16 57 1 0 21 58 1 0 24 59 1 0 24 60 1 0 24 61 1 0 27 62 1 0 29 63 1 0 29 64 1 0 29 65 1 0 32 66 1 0 32 67 1 0 32 68 1 0 35 69 1 0 37 70 1 0 37 71 1 0 37 72 1 0 39 73 1 0 39 74 1 0 39 75 1 0 40 76 1 0 40 77 1 0 40 78 1 0 M END

Standard InCHIKey	MLZWZUMLLVUXMT-KDIWVURASA-N
Standard InCHI	InChI=1S/C30H38O10/c1-11-14(2)30(33)40-26-16(4)15(3)25(39-17(5)31)19-13-21(35-7)28(37-9)29(38-10)23(19)22-18(26)12-20(34-6)27(36-8)24(22)32/h11-13,15-16,25-26,32H,1-10H3/b14-11-/t15-,16+,25+,26+/m1/s1
SMILES	C/C=C(C(=O)O[C@H]1[C@@H](C)[C@@H](C)[C@H](OC(=O)C)c2c(c3c1cc(OC)c(c3O)OC)c(OC)c(c(c2)OC)OC)/C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	558.25	Volume:	565.941 ? Van der Waals volume.
Dense:	0.986	LogP:	3.145 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.094 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.481 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	10.0	Rigid Bonds:	21.0
TPSA:	118.98 ? Topological Polar Surface Area.	H-Bond Acceptor:	10.0
H-Bond Donor:	1.0	Rings:	3.0
Heavy Atoms:	10.0

MedChem Properties

QED Drug-Likeness Score:	0.327	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.252	Fsp³:	0.467
MCE-18:	82.727 ? 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:	1	PAINS Alert:	0
Colloidal aggregators:	0.239	Fluc inhibitor:	0.122 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.235 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.579 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.324	Promiscuous compounds:	0.213

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.081	MDCK Permeability:	-4.731
Pgp-inhibitor:	0.767	Pgp-substrate:	0.15
PAMPA:	0.084 ? 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):	0.062
20% Bioavailability (F20%):	0.761	30% Bioavailability (F30%):	0.533
50% Bioavailability (F50%):	0.992

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.087	MRP1:	0.999
Plasma Protein Binding (PPB):	98.081%	Volume Distribution (VD):	-0.27
Fu:	2.369% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.993
OATP1B3 inhibitor:	0.994	BCRP inhibitor:	0.381
BSEP inhibitor:	0.906

ADMET: Metabolism

CYP1A2-inhibitor:	0.897	CYP1A2-substrate:	0.955
CYP2C19-inhibitor:	0.948	CYP2C19-substrate:	0.842
CYP2C9-inhibitor:	0.156	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.144
CYP3A4-inhibitor:	0.998	CYP3A4-substrate:	0.033
CYP2B6-substrate:	0.003	CYP2C8-inhibitor:	0.998
HLM stability:	0.983 ? 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):

4.99

Half-life (T1/2):

1.075

ADMET: Toxicity

hERG Blockers:	0.097	hERG Blockers (10um):	0.399
Human Hepatotoxicity (H-HT):	0.72	Drug-induced Liver Injury (DILI):	0.971
AMES Toxicity:	0.905	Rat Oral Acute Toxicity:	0.688
Maximum Recommended Daily Dose:	0.933	Skin Sensitization:	0.971
Carcinogencity:	0.861	Eye Corrosion:	0.0
Eye Irritation:	0.122	Respiratory Toxicity:	0.717
Drug-induced Neurotoxicity:	0.835	Ototoxicity:	0.543
Hematotoxicity:	0.82	Drug-induced Nephrotoxicity:	0.914
Genotoxicity:	0.88	RPMI-8226 Immunitoxicity:	0.469
A549 Cytotoxicity:	0.791	Hek293 Cytotoxicity:	0.72
BCF:	1.032 ? 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:	3.598 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.06 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.492 ? 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
NPO18146	Kadsura angustifolia	Species	Schisandraceae	Eukaryota	stems	Honghe Prefecture of Yunnan Province, China	2005-Oct	PMID[18278869]
NPO18146	Kadsura angustifolia	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21232955]
NPO18146	Kadsura angustifolia	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18146	Kadsura angustifolia	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18146	Kadsura angustifolia	Species	Schisandraceae	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
EC50	1
Ratio	1
CC50	1

Activity Type	# Activity
Cell line	1
Organism	1
Others	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
NPT1452	Cell line	C8166	Homo sapiens	CC50	=	159520.0	nM	PubChem BioAssay data set
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	EC50	=	72620.0	nM	PMID[12088420]
NPT2	Others	Unspecified	n.a.	Ratio	=	2.2	n.a.	PMID[17257839]

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 NPC474347 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	12101
0.1-0.2	34408
0.2-0.3	3169
0.3-0.4	113
0.4-0.5	37
0.5-0.6	19
0.6-0.7	9
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC474393
0.697	Remote Similarity	NPC475141
0.6923	Remote Similarity	NPC473445
0.6667	Remote Similarity	NPC327352
0.6667	Remote Similarity	NPC474054
0.6667	Remote Similarity	NPC198129
0.6667	Remote Similarity	NPC252281
0.6522	Remote Similarity	NPC476065
0.6286	Remote Similarity	NPC475592
0.6197	Remote Similarity	NPC483406
0.5972	Remote Similarity	NPC483405
0.5938	Remote Similarity	NPC322426
0.5758	Remote Similarity	NPC316989
0.5526	Remote Similarity	NPC473736
0.55	Remote Similarity	NPC326144
0.5479	Remote Similarity	NPC475756
0.5352	Remote Similarity	NPC24562
0.5333	Remote Similarity	NPC291977
0.5325	Remote Similarity	NPC485504
0.5312	Remote Similarity	NPC318286
0.5211	Remote Similarity	NPC308739
0.5205	Remote Similarity	NPC477885
0.5156	Remote Similarity	NPC327651
0.5152	Remote Similarity	NPC321958
0.5132	Remote Similarity	NPC474606
0.5128	Remote Similarity	NPC238834
0.5079	Remote Similarity	NPC865
0.507	Remote Similarity	NPC312763
0.5068	Remote Similarity	NPC470916

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC474347 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4420
0.1-0.2	4656
0.2-0.3	74
0.3-0.4	0
0.4-0.5	0
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