NPASS Compound

Natural Product: NPC472992

Natural Product ID	NPC472992
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	ACHIQCZROFTJIU-DBIPPQOESA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL3597470
PubChem CID	n.a.
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001111] Flavonoid glycosides [CHEMONTID:0001583] Flavonoid 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 69 73 0 0 0 0 0 0 0 0999 V2000 -4.2491 3.4687 -0.1249 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7585 4.7203 -0.2357 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8294 5.0177 -1.0357 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4130 4.0111 -1.7557 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8896 2.7274 -1.6415 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8143 2.4010 -0.8449 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2544 1.0681 -0.7125 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7382 0.0417 -1.3571 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1684 -1.3069 -1.2204 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6150 -2.2901 -1.8244 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0908 -1.4928 -0.3859 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4664 -2.7262 -0.1768 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5542 -3.2343 1.2237 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6611 -4.4533 1.3208 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2817 -5.0037 -0.0148 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7176 -4.1011 -0.8684 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0326 -2.7723 -0.6013 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2304 -2.3327 0.4449 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7346 -1.3766 0.4186 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0681 -1.6248 0.1484 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0243 -0.6534 0.1258 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6582 0.6564 0.3849 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3262 0.9632 0.6635 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3920 -0.0663 0.6736 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9216 0.2722 0.9535 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5547 1.6042 0.3693 O 0 0 0 0 0 0 0 0 0 0 0 0 4.8318 1.4207 0.1186 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2450 0.1404 -0.1443 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3421 -0.9130 -0.1433 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6812 -2.0916 -0.3782 O 0 0 0 0 0 0 0 0 0 0 0 0 5.7179 2.5825 0.1368 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0646 2.5220 -0.1077 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8485 3.6804 -0.0721 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3155 4.9204 0.2060 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9627 4.9788 0.4512 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1940 3.8345 0.4150 C 0 0 0 0 0 0 0 0 0 0 0 0 8.1180 6.0514 0.2343 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4318 -2.9311 -0.1098 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2183 -6.0818 0.2374 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1349 -6.6949 -0.9833 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3295 -5.4019 2.0622 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.0909 -2.3147 2.1734 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.3686 6.2934 -1.1648 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4083 3.2263 0.5009 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3269 5.5633 0.3208 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2590 4.1596 -2.4088 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3710 1.9286 -2.2276 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4121 0.9241 -0.0603 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5753 0.1595 -2.0114 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0237 -3.4740 -0.8148 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5981 -3.4638 1.5323 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7080 -4.2172 1.8634 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1484 -5.5563 -0.4563 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8669 -2.2287 -1.5540 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0684 1.9912 0.8617 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1927 0.3490 1.9220 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2770 -0.0387 -0.3514 H 0 0 0 0 0 0 0 0 0 0 0 0 7.5033 1.5639 -0.3272 H 0 0 0 0 0 0 0 0 0 0 0 0 8.9043 3.6051 -0.2679 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5253 5.9463 0.6719 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1132 3.9113 0.6155 H 0 0 0 0 0 0 0 0 0 0 0 0 9.0056 6.0029 -0.2494 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6913 -3.5921 0.6152 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7339 -5.6071 0.6060 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5286 -6.8054 0.9868 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0319 -7.0800 -0.9497 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1578 -5.3881 3.0146 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8485 -1.7782 2.5450 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3813 6.3855 -1.2356 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 2 3 1 0 3 4 2 0 4 5 1 0 5 6 2 0 6 7 1 0 7 8 2 3 8 9 1 0 9 10 2 0 9 11 1 0 11 12 1 0 12 13 1 0 13 14 1 0 14 15 1 0 15 16 1 0 16 17 1 0 17 18 1 0 18 19 1 0 19 20 2 0 20 21 1 0 21 22 2 0 22 23 1 0 23 24 2 0 24 25 1 0 22 26 1 0 26 27 1 0 27 28 2 0 28 29 1 0 29 30 2 0 27 31 1 0 31 32 2 0 32 33 1 0 33 34 2 0 34 35 1 0 35 36 2 0 34 37 1 0 20 38 1 0 15 39 1 0 39 40 1 0 14 41 1 0 13 42 1 0 3 43 1 0 6 1 1 0 17 12 1 0 24 19 1 0 29 21 1 0 36 31 1 0 1 44 1 0 2 45 1 0 4 46 1 0 5 47 1 0 7 48 1 0 8 49 1 0 12 50 1 0 13 51 1 0 14 52 1 0 15 53 1 0 17 54 1 0 23 55 1 0 25 56 1 0 28 57 1 0 32 58 1 0 33 59 1 0 35 60 1 0 36 61 1 0 37 62 1 0 38 63 1 0 39 64 1 0 39 65 1 0 40 66 1 0 41 67 1 0 42 68 1 0 43 69 1 0 M END

Standard InCHIKey	ACHIQCZROFTJIU-DBIPPQOESA-N
Standard InCHI	InChI=1S/C30H26O13/c31-13-22-25(37)27(39)29(42-23(36)10-3-14-1-6-16(32)7-2-14)30(41-22)43-28-19(35)12-21-24(26(28)38)18(34)11-20(40-21)15-4-8-17(33)9-5-15/h1-12,22,25,27,29-33,35,37-39H,13H2/b10-3+/t22-,25-,27+,29-,30+/m1/s1
SMILES	C1=CC(=CC=C1C=CC(=O)OC2C(C(C(OC2OC3=C(C4=C(C=C3O)OC(=CC4=O)C5=CC=C(C=C5)O)O)CO)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	594.14	Volume:	564.653 ? Van der Waals volume.
Dense:	1.052	LogP:	1.587 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.542 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.211 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	8.0	Rigid Bonds:	32.0
TPSA:	216.58 ? Topological Polar Surface Area.	H-Bond Acceptor:	13.0
H-Bond Donor:	7.0	Rings:	5.0
Heavy Atoms:	13.0

MedChem Properties

QED Drug-Likeness Score:	0.12	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.239	Fsp³:	0.2
MCE-18:	104.889 ? 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:	1	PAINS Alert:	0
Colloidal aggregators:	0.852	Fluc inhibitor:	0.434 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.978 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.993 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.481	Promiscuous compounds:	0.958

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.279	MDCK Permeability:	-5.109
Pgp-inhibitor:	0.0	Pgp-substrate:	0.206
PAMPA:	0.993 ? 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):	0.046
20% Bioavailability (F20%):	0.987	30% Bioavailability (F30%):	0.999
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.643
Plasma Protein Binding (PPB):	86.149%	Volume Distribution (VD):	-0.087
Fu:	12.209% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.325
OATP1B3 inhibitor:	0.986	BCRP inhibitor:	0.236
BSEP inhibitor:	0.373

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.203	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.466	CYP2D6-substrate:	0.144
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.001 ? 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):

2.854

Half-life (T1/2):

2.312

ADMET: Toxicity

hERG Blockers:	0.076	hERG Blockers (10um):	0.505
Human Hepatotoxicity (H-HT):	0.436	Drug-induced Liver Injury (DILI):	0.676
AMES Toxicity:	0.658	Rat Oral Acute Toxicity:	0.419
Maximum Recommended Daily Dose:	0.878	Skin Sensitization:	0.946
Carcinogencity:	0.301	Eye Corrosion:	0.0
Eye Irritation:	0.533	Respiratory Toxicity:	0.131
Drug-induced Neurotoxicity:	0.084	Ototoxicity:	0.644
Hematotoxicity:	0.011	Drug-induced Nephrotoxicity:	0.048
Genotoxicity:	0.963	RPMI-8226 Immunitoxicity:	0.055
A549 Cytotoxicity:	0.412	Hek293 Cytotoxicity:	0.966
BCF:	0.696 ? 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:	3.463 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.625 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.163 ? 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
NPO26700	Tinospora crispa	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20356064]
NPO26700	Tinospora crispa	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22283497]
NPO26700	Tinospora crispa	Species	Menispermaceae	Eukaryota	leaf	Putz City, Chiayi County, Taiwan	2009-Nov	PMID[25999202]
NPO26700	Tinospora crispa	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28742368]
NPO26700	Tinospora crispa	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[29397715]
NPO26700	Tinospora crispa	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26700	Tinospora crispa	Species	Menispermaceae	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	1

Activity Type	# Activity
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
NPT2	Others	Unspecified	n.a.	IC50	=	4300.0	nM	PMID[21920741]

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 NPC472992 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	10363
0.1-0.2	34145
0.2-0.3	4248
0.3-0.4	848
0.4-0.5	196
0.5-0.6	47
0.6-0.7	4
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.9157	High Similarity	NPC472991
0.7841	Intermediate Similarity	NPC477628
0.6429	Remote Similarity	NPC260504
0.6429	Remote Similarity	NPC89809
0.6058	Remote Similarity	NPC470712
0.6058	Remote Similarity	NPC164704
0.596	Remote Similarity	NPC210961
0.596	Remote Similarity	NPC139060
0.5943	Remote Similarity	NPC470718
0.5755	Remote Similarity	NPC470715
0.5752	Remote Similarity	NPC199172
0.5728	Remote Similarity	NPC218161
0.5638	Remote Similarity	NPC80188
0.5588	Remote Similarity	NPC221288
0.5588	Remote Similarity	NPC194836
0.5588	Remote Similarity	NPC91493
0.5588	Remote Similarity	NPC605081
0.5536	Remote Similarity	NPC470720
0.5474	Remote Similarity	NPC224530
0.5446	Remote Similarity	NPC470717
0.5431	Remote Similarity	NPC480470
0.5405	Remote Similarity	NPC76047
0.54	Remote Similarity	NPC65003
0.5385	Remote Similarity	NPC477629
0.5357	Remote Similarity	NPC470713
0.5347	Remote Similarity	NPC122809
0.5288	Remote Similarity	NPC205824
0.5288	Remote Similarity	NPC270675
0.5288	Remote Similarity	NPC195685
0.5213	Remote Similarity	NPC149011
0.5196	Remote Similarity	NPC470444
0.5192	Remote Similarity	NPC104883
0.5192	Remote Similarity	NPC488679
0.5189	Remote Similarity	NPC36138
0.5185	Remote Similarity	NPC241498
0.5175	Remote Similarity	NPC162394
0.5169	Remote Similarity	NPC35924
0.5164	Remote Similarity	NPC249560
0.5143	Remote Similarity	NPC101399
0.5143	Remote Similarity	NPC217822
0.5143	Remote Similarity	NPC11847
0.5143	Remote Similarity	NPC198938
0.514	Remote Similarity	NPC483767
0.514	Remote Similarity	NPC483769
0.514	Remote Similarity	NPC483768
0.514	Remote Similarity	NPC483766
0.5128	Remote Similarity	NPC480472
0.5104	Remote Similarity	NPC475942
0.5102	Remote Similarity	NPC479643
0.5096	Remote Similarity	NPC476619
0.5093	Remote Similarity	NPC483765
0.5091	Remote Similarity	NPC473278
0.5053	Remote Similarity	NPC93337

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC472992 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3481
0.1-0.2	5564
0.2-0.3	95
0.3-0.4	9
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