NPASS Compound

Natural Product: NPC152618

Natural Product ID	NPC152618
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	VGXJTTXSNPYTSK-UHFFFAOYSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	5316141
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000296] Benzodioxoles

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 26 27 0 0 0 0 0 0 0 0999 V2000 -3.8122 -1.0772 -0.1915 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7755 -0.3613 0.1867 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8930 0.3337 -0.7791 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5023 -0.1130 -0.7060 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0744 -0.9672 -1.6474 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3884 -1.3761 -1.5579 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1688 -0.9279 -0.5005 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6230 -0.0804 0.4470 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3017 0.3026 0.3161 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2045 1.1543 1.2905 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0788 2.5442 1.0519 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6036 0.2145 1.3858 O 0 0 0 0 0 0 0 0 0 0 0 0 3.6949 -0.7014 1.2183 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4825 -1.1302 -0.1107 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.0772 -1.1968 -1.2419 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4326 -1.5699 0.5463 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5510 -0.2708 1.2407 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2640 0.0808 -1.8115 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0459 1.4116 -0.6607 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5482 -1.2996 -2.4542 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8491 -2.0370 -2.2786 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0892 2.9466 0.9151 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3972 3.0688 1.9120 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4919 2.7669 0.1107 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5379 -1.5257 1.9608 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6611 -0.1893 1.3582 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 2 3 1 0 3 4 1 0 4 5 2 0 5 6 1 0 6 7 2 0 7 8 1 0 8 9 2 0 9 10 1 0 10 11 1 0 8 12 1 0 12 13 1 0 13 14 1 0 9 4 1 0 14 7 1 0 1 15 1 0 1 16 1 0 2 17 1 0 3 18 1 0 3 19 1 0 5 20 1 0 6 21 1 0 11 22 1 0 11 23 1 0 11 24 1 0 13 25 1 0 13 26 1 0 M END

Standard InCHIKey	VGXJTTXSNPYTSK-UHFFFAOYSA-N
Standard InCHI	InChI=1S/C11H12O3/c1-3-4-8-5-6-9-11(10(8)12-2)14-7-13-9/h3,5-6H,1,4,7H2,2H3
SMILES	C=CCc1ccc2c(c1OC)OCO2

Calculated Properties

Physi-Chem Properties

Molecular Weight:	192.08	Volume:	197.524 ? Van der Waals volume.
Dense:	0.972	LogP:	2.719 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.513 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.793 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	3.0	Rigid Bonds:	11.0
TPSA:	27.69 ? Topological Polar Surface Area.	H-Bond Acceptor:	3.0
H-Bond Donor:	0.0	Rings:	2.0
Heavy Atoms:	3.0

MedChem Properties

QED Drug-Likeness Score:	0.687	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	2.434	Fsp³:	0.273
MCE-18:	21.429 ? 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:	Rejected
Golden Triangle Rule:	Accepted	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.059	Fluc inhibitor:	0.095 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.044 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.195 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.807	Promiscuous compounds:	0.058

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.619	MDCK Permeability:	-4.74
Pgp-inhibitor:	0.82	Pgp-substrate:	0.0
PAMPA:	0.006 ? 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):	0.001
20% Bioavailability (F20%):	0.413	30% Bioavailability (F30%):	0.049
50% Bioavailability (F50%):	0.544

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.897	MRP1:	0.336
Plasma Protein Binding (PPB):	94.462%	Volume Distribution (VD):	0.407
Fu:	6.366% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.998
OATP1B3 inhibitor:	0.988	BCRP inhibitor:	0.442
BSEP inhibitor:	0.998

ADMET: Metabolism

CYP1A2-inhibitor:	0.999	CYP1A2-substrate:	0.993
CYP2C19-inhibitor:	0.993	CYP2C19-substrate:	0.158
CYP2C9-inhibitor:	0.999	CYP2C9-substrate:	1.0
CYP2D6-inhibitor:	1.0	CYP2D6-substrate:	1.0
CYP3A4-inhibitor:	0.005	CYP3A4-substrate:	0.998
CYP2B6-substrate:	0.992	CYP2C8-inhibitor:	0.949
HLM stability:	0.426 ? 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):

5.472

Half-life (T1/2):

1.152

ADMET: Toxicity

hERG Blockers:	0.114	hERG Blockers (10um):	0.611
Human Hepatotoxicity (H-HT):	0.327	Drug-induced Liver Injury (DILI):	0.51
AMES Toxicity:	0.521	Rat Oral Acute Toxicity:	0.391
Maximum Recommended Daily Dose:	0.295	Skin Sensitization:	0.806
Carcinogencity:	0.832	Eye Corrosion:	0.95
Eye Irritation:	0.982	Respiratory Toxicity:	0.832
Drug-induced Neurotoxicity:	0.671	Ototoxicity:	0.152
Hematotoxicity:	0.233	Drug-induced Nephrotoxicity:	0.163
Genotoxicity:	0.177	RPMI-8226 Immunitoxicity:	0.06
A549 Cytotoxicity:	0.08	Hek293 Cytotoxicity:	0.227
BCF:	1.72 ? 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:	3.52 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.094 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.219 ? 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
NPO3939	Ardisia arborescens	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[15387676]
NPO2978	Croton tiglium	Species	Euphorbiaceae	Eukaryota	n.a.	seed	n.a.	PMID[21049973]
NPO16877	Aconitum episcopale	Species	Ranunculaceae	Eukaryota	n.a.	root	n.a.	PMID[21417277]
NPO14126	Garcinia oligantha	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22365754]
NPO6336	Asarum sieboldii	Species	Aristolochiaceae	Eukaryota	roots	n.a.	n.a.	PMID[22381047]
NPO2978	Croton tiglium	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23701597]
NPO2978	Croton tiglium	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25819096]
NPO14126	Garcinia oligantha	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27329938]
NPO14126	Garcinia oligantha	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[33296199]
NPO3741	Pagrus major	Species	Sparidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2978	Croton tiglium	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15902	Iris spuria	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14126	Garcinia oligantha	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16119	Eucalyptus hybrid	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15193	Cacia concinna	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16552	Aromia moschata	Species	Cerambycidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3939	Ardisia arborescens	Species	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16877	Aconitum episcopale	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7909	Parmelia vittata	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9962	Pocillopora damicornis	Species	Pocilloporidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13926	Protaetia cuprea	Species	Scarabaeidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4659	Asiasarum heterotropoides	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12468	Asarum heterotropoides	Species	Aristolochiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO29078	Asiasarum sieboldii	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12468.1	Asarum heterotropoides var. mandshuricum	Varieties	Aristolochiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO745	Rubus trifidus	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6336	Asarum sieboldii	Species	Aristolochiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6336	Asarum sieboldii	Species	Aristolochiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3939	Ardisia arborescens	Species	n.a.	n.a.	n.a.	n.a.	n.a.	Database[HerDing]
NPO12468.1	Asarum heterotropoides var. mandshuricum	Varieties	Aristolochiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2978	Croton tiglium	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3939	Ardisia arborescens	Species	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TCMID]
NPO12468.1	Asarum heterotropoides var. mandshuricum	Varieties	Aristolochiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6336	Asarum sieboldii	Species	Aristolochiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2978	Croton tiglium	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15902	Iris spuria	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12468.2	Asarum heterotropoides f. schm. var. mandshuricum (maxim.) kitag.	Varieties	Aristolochiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO12468	Asarum heterotropoides	Species	Aristolochiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO2978	Croton tiglium	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO6336	Asarum sieboldii	Species	Aristolochiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO29078	Asiasarum sieboldii	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TM-MC]
NPO2978	Croton tiglium	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO4659	Asiasarum heterotropoides	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TM-MC]
NPO12468	Asarum heterotropoides	Species	Aristolochiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO6336	Asarum sieboldii	Species	Aristolochiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO15193	Cacia concinna	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO15902	Iris spuria	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9962	Pocillopora damicornis	Species	Pocilloporidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13926	Protaetia cuprea	Species	Scarabaeidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3741	Pagrus major	Species	Sparidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14126	Garcinia oligantha	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16552	Aromia moschata	Species	Cerambycidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7909	Parmelia vittata	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29078	Asiasarum sieboldii	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO16877	Aconitum episcopale	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3939	Ardisia arborescens	Species	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO16119	Eucalyptus hybrid	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2978	Croton tiglium	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12468	Asarum heterotropoides	Species	Aristolochiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO745	Rubus trifidus	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4659	Asiasarum heterotropoides	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO6336	Asarum sieboldii	Species	Aristolochiaceae	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 NPC152618 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	24986
0.1-0.2	21590
0.2-0.3	2918
0.3-0.4	333
0.4-0.5	22
0.5-0.6	5
0.6-0.7	2
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	Natural Product ID
0.6667	Remote Similarity	NPC283170
0.641	Remote Similarity	NPC92869
0.5854	Remote Similarity	NPC191768
0.561	Remote Similarity	NPC276863
0.5366	Remote Similarity	NPC119949
0.525	Remote Similarity	NPC31279
0.5128	Remote Similarity	NPC308217

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC152618 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4261
0.1-0.2	4679
0.2-0.3	200
0.3-0.4	10
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