NPASS Compound

Structure

CID25581 OpenBabel06191715352D 26 27 0 0 1 0 0 0 0 0999 V2000 6.0622 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 3.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 3.4641 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6603 5.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 8.6603 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 4 2 0 0 0 0 1 10 1 0 0 0 0 2 5 2 0 0 0 0 2 11 1 0 0 0 0 3 6 2 0 0 0 0 3 10 1 0 0 0 0 4 12 1 0 0 0 0 5 13 1 0 0 0 0 6 17 1 0 0 0 0 7 10 2 0 0 0 0 7 14 1 0 0 0 0 8 11 2 0 0 0 0 8 15 1 0 0 0 0 9 11 1 0 0 0 0 9 16 1 0 0 0 0 12 14 2 0 0 0 0 12 19 1 0 0 0 0 13 15 2 0 0 0 0 13 20 1 0 0 0 0 14 21 1 0 0 0 0 15 22 1 0 0 0 0 16 18 1 0 0 0 0 16 26 1 0 0 0 0 17 23 2 0 0 0 0 17 26 1 0 0 0 0 18 24 2 0 0 0 0 18 25 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	360.08
Volume:	349.365
LogP:	1.775
LogD:	1.65
LogS:	-2.432
# Rotatable Bonds:	7
TPSA:	144.52
# H-Bond Aceptor:	8
# H-Bond Donor:	5
# Rings:	2
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.298
Synthetic Accessibility Score:	2.903
Fsp3:	0.111
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.005
MDCK Permeability:	6.939773811609484e-06
Pgp-inhibitor:	0.0
Pgp-substrate:	0.004
Human Intestinal Absorption (HIA):	0.231
20% Bioavailability (F20%):	0.505
30% Bioavailability (F30%):	0.994

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.049
Plasma Protein Binding (PPB):	97.72160339355469%
Volume Distribution (VD):	0.369
Pgp-substrate:	2.0430641174316406%

ADMET: Metabolism

CYP1A2-inhibitor:	0.138
CYP1A2-substrate:	0.043
CYP2C19-inhibitor:	0.117
CYP2C19-substrate:	0.041
CYP2C9-inhibitor:	0.554
CYP2C9-substrate:	0.798
CYP2D6-inhibitor:	0.06
CYP2D6-substrate:	0.204
CYP3A4-inhibitor:	0.092
CYP3A4-substrate:	0.041

ADMET: Excretion

Clearance (CL):	15.347
Half-life (T1/2):	0.959

ADMET: Toxicity

hERG Blockers:	0.015
Human Hepatotoxicity (H-HT):	0.446
Drug-inuced Liver Injury (DILI):	0.367
AMES Toxicity:	0.035
Rat Oral Acute Toxicity:	0.451
Maximum Recommended Daily Dose:	0.035
Skin Sensitization:	0.951
Carcinogencity:	0.275
Eye Corrosion:	0.005
Eye Irritation:	0.852
Respiratory Toxicity:	0.052

Download Data

Data Type	Select
General Info & Identifiers & Properties
Structure MOL file
Source Organisms
Biological Activities
Similar NPs/Drugs

Natural Product: NPC25581

Natural Product ID:	NPC25581
*Common Name:**	3-(3,4-Dihydroxyphenyl)-2-[(E)-3-(3,4-Dihydroxyphenyl)Prop-2-Enoyl]Oxypropanoic Acid
IUPAC Name:	3-(3,4-dihydroxyphenyl)-2-[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxypropanoic acid
Synonyms:
Standard InCHIKey:	DOUMFZQKYFQNTF-ZZXKWVIFSA-N
Standard InCHI:	InChI=1S/C18H16O8/c19-12-4-1-10(7-14(12)21)3-6-17(23)26-16(18(24)25)9-11-2-5-13(20)15(22)8-11/h1-8,16,19-22H,9H2,(H,24,25)/b6-3+
SMILES:	c1cc(c(cc1/C=C/C(=O)OC(Cc1ccc(c(c1)O)O)C(=O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL66966
PubChem CID:	5315615
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000476] Cinnamic acids and derivatives [CHEMONTID:0001391] Hydroxycinnamic acids and derivatives [CHEMONTID:0000059] Coumaric acids and derivatives

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO28295	Foeniculum vulgare	Species	Apiaceae	Eukaryota	n.a.	leaf	n.a.	DOI[10.1016/S0031-9422(00)94055-X]
NPO28295	Foeniculum vulgare	Species	Apiaceae	Eukaryota	n.a.	flower	n.a.	DOI[10.3390/70200245]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	root	n.a.	PMID[11374966]
NPO28679	Prunus mume	Species	Rosaceae	Eukaryota	flowers	n.a.	n.a.	PMID[12193020]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16038550]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17583950]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18855446]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20455578]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21775156]
NPO8650	Perilla frutescens	Species	Lamiaceae	Eukaryota	leaves	n.a.	n.a.	PMID[22272932]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23286284]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24108414]
NPO28679	Prunus mume	Species	Rosaceae	Eukaryota	fruits	n.a.	n.a.	PMID[24485782]
NPO28295	Foeniculum vulgare	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24617303]
NPO8650	Perilla frutescens	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25320841]
NPO28626	Isodon rubescens	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25590529]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27569393]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[29185738]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[30351923]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	root	n.a.	PMID[3655791]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	roots	n.a.	n.a.	PMID[9834151]
NPO28679	Prunus mume	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28295	Foeniculum vulgare	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO31056	Mentha haplocalyx	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21824	Lycopus lucidus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8650	Perilla frutescens	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28626	Isodon rubescens	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28295	Foeniculum vulgare	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28679	Prunus mume	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21824	Lycopus lucidus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8650	Perilla frutescens	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO28679	Prunus mume	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO31056	Mentha haplocalyx	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO21824	Lycopus lucidus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO8650	Perilla frutescens	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO28295	Foeniculum vulgare	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO21824	Lycopus lucidus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO28679	Prunus mume	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO28626	Isodon rubescens	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO8650	Perilla frutescens	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO28295	Foeniculum vulgare	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO28679	Prunus mume	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21824	Lycopus lucidus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28295	Foeniculum vulgare	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28626	Isodon rubescens	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8650	Perilla frutescens	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	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	NP ID	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	3
IC50	6
Potency	50

Activity Type	# Activity
Individual Protein	47
Organism	3
Others	7
Protein-Protein Interaction	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT47	Individual Protein	ATP-dependent DNA helicase Q1	Homo sapiens	Potency	=	12589.3	nM	PMID[479198]
NPT149	Individual Protein	Endoplasmic reticulum-associated amyloid beta-peptide-binding protein	Homo sapiens	Potency	=	15848.9	nM	PMID[479198]
NPT48	Individual Protein	Lysine-specific demethylase 4D-like	Homo sapiens	Potency	=	3981.1	nM	PMID[479198]
NPT48	Individual Protein	Lysine-specific demethylase 4D-like	Homo sapiens	Potency	=	25118.9	nM	PMID[479199]
NPT50	Individual Protein	Tyrosyl-DNA phosphodiesterase 1	Homo sapiens	Potency	=	8912.5	nM	PMID[479199]
NPT50	Individual Protein	Tyrosyl-DNA phosphodiesterase 1	Homo sapiens	Potency	=	891.3	nM	PMID[479198]
NPT51	Individual Protein	Microtubule-associated protein tau	Homo sapiens	Potency	=	14125.4	nM	PMID[479198]
NPT51	Individual Protein	Microtubule-associated protein tau	Homo sapiens	Potency	=	12589.3	nM	PMID[479198]
NPT3	Individual Protein	Thioredoxin glutathione reductase	Schistosoma mansoni	Potency	=	35481.3	nM	PMID[479200]
NPT53	Individual Protein	4'-phosphopantetheinyl transferase ffp	Bacillus subtilis	Potency	=	79432.8	nM	PMID[479200]
NPT53	Individual Protein	4'-phosphopantetheinyl transferase ffp	Bacillus subtilis	Potency	=	56234.1	nM	PMID[479198]
NPT55	Individual Protein	Putative fructose-1,6-bisphosphate aldolase	Giardia intestinalis	Potency	=	4466.8	nM	PMID[479200]
NPT55	Individual Protein	Putative fructose-1,6-bisphosphate aldolase	Giardia intestinalis	Potency	=	19905.4	nM	PMID[479198]
NPT56	Individual Protein	Beta-lactamase AmpC	Escherichia coli K-12	Potency	=	100000.0	nM	PMID[479200]
NPT151	Individual Protein	15-hydroxyprostaglandin dehydrogenase [NAD+]	Homo sapiens	Potency	=	22387.2	nM	PMID[479198]
NPT583	Individual Protein	Inositol monophosphatase 1	Rattus norvegicus	Potency	=	19952.6	nM	PMID[479198]
NPT60	Individual Protein	Lysosomal alpha-glucosidase	Homo sapiens	Potency	=	1995.3	nM	PMID[479200]
NPT59	Individual Protein	DNA polymerase beta	Homo sapiens	Potency	=	1995.3	nM	PMID[479200]
NPT532	Individual Protein	Lysine-specific demethylase 4A	Homo sapiens	Potency	n.a.	12589.3	nM	PMID[479200]
NPT62	Individual Protein	6-phospho-1-fructokinase	Trypanosoma brucei	Potency	n.a.	2393.4	nM	PMID[479200]
NPT443	Individual Protein	Histone acetyltransferase GCN5	Homo sapiens	Potency	n.a.	39810.7	nM	PMID[479198]
NPT443	Individual Protein	Histone acetyltransferase GCN5	Homo sapiens	Potency	n.a.	707.9	nM	PMID[479199]
NPT62	Individual Protein	6-phospho-1-fructokinase	Trypanosoma brucei	Potency	n.a.	2685.5	nM	PMID[479200]
NPT5	Individual Protein	Histone-lysine N-methyltransferase, H3 lysine-9 specific 3	Homo sapiens	Potency	n.a.	3548.1	nM	PMID[479200]
NPT63	Individual Protein	Bromodomain adjacent to zinc finger domain protein 2B	Homo sapiens	Potency	n.a.	39810.7	nM	PMID[479200]
NPT62	Individual Protein	6-phospho-1-fructokinase	Trypanosoma brucei	Potency	n.a.	3380.8	nM	PMID[479200]
NPT135	Individual Protein	Chromobox protein homolog 1	Homo sapiens	Potency	n.a.	50118.7	nM	PMID[479200]
NPT199	Individual Protein	DNA polymerase kappa	Homo sapiens	Potency	n.a.	1995.3	nM	PMID[479200]
NPT199	Individual Protein	DNA polymerase kappa	Homo sapiens	Potency	n.a.	2238.7	nM	PMID[479199]
NPT199	Individual Protein	DNA polymerase kappa	Homo sapiens	Potency	n.a.	251.2	nM	PMID[479198]
NPT534	Individual Protein	Phosphoglycerate kinase, glycosomal	Trypanosoma brucei brucei	Potency	n.a.	8912.5	nM	PMID[479200]
NPT1852	Individual Protein	Rac GTPase-activating protein 1	Homo sapiens	IC50	n.a.	35000.0	nM	PMID[479200]
NPT100	Individual Protein	Glutaminase kidney isoform, mitochondrial	Homo sapiens	Potency	n.a.	35481.3	nM	PMID[479200]
NPT1853	Individual Protein	Putative uncharacterized protein	Trypanosoma brucei brucei (strain 927/4 GUTat10.1)	Potency	n.a.	31622.8	nM	PMID[479200]
NPT1854	Individual Protein	Phosphoglycerate kinase	Trypanosoma brucei brucei (strain 927/4 GUTat10.1)	Potency	n.a.	12981.9	nM	PMID[479200]
NPT105	Individual Protein	Muscleblind-like protein 1	Homo sapiens	Potency	n.a.	28183.8	nM	PMID[479200]
NPT49	Individual Protein	DNA-(apurinic or apyrimidinic site) lyase	Homo sapiens	Potency	n.a.	10000.0	nM	PMID[479199]
NPT49	Individual Protein	DNA-(apurinic or apyrimidinic site) lyase	Homo sapiens	Potency	n.a.	1258.9	nM	PMID[479198]
NPT1098	Individual Protein	Eyes absent homolog 2	Homo sapiens	Potency	n.a.	4776.3	nM	PMID[479200]
NPT791	Individual Protein	Cruzipain	Trypanosoma cruzi	Potency	=	31622.8	nM	PMID[479198]
NPT795	Individual Protein	Zinc finger protein mex-5	Caenorhabditis elegans	EC50	=	8751.0	nM	PMID[479200]
NPT2	Others	Unspecified		EC50	>	110000.0	nM	PMID[479200]
NPT797	Individual Protein	Cytoplasmic zinc-finger protein	Caenorhabditis elegans	EC50	=	13604.0	nM	PMID[479200]
NPT533	Protein-Protein Interaction	Runt-related transcription factor 1/Core-binding factor subunit beta	Homo sapiens	Potency	n.a.	8912.5	nM	PMID[479198]
NPT21702	PROTEIN-PROTEIN INTERACTION	Importin subunit beta-1/Snurportin-1	Homo sapiens	Potency	n.a.	125892.5	nM	PMID[479200]
NPT8	Individual Protein	DNA polymerase iota	Homo sapiens	Potency	n.a.	2511.9	nM	PMID[479200]
NPT803	Individual Protein	Flap endonuclease 1	Homo sapiens	Potency	n.a.	50118.7	nM	PMID[479200]
NPT9	Individual Protein	DNA polymerase eta	Homo sapiens	Potency	n.a.	1584.9	nM	PMID[479200]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Potency	n.a.	369.6	nM	PMID[479200]
NPT2	Others	Unspecified		Potency	n.a.	10000.0	nM	PMID[479200]
NPT2	Others	Unspecified		IC50	n.a.	44080.0	nM	PMID[479200]
NPT9	Individual Protein	DNA polymerase eta	Homo sapiens	Potency	n.a.	11995.5	nM	PMID[479200]
NPT2	Others	Unspecified		IC50	=	6845.0	nM	PMID[479200]
NPT2	Others	Unspecified		Potency	n.a.	7079.5	nM	PMID[479199]
NPT2	Others	Unspecified		IC50	=	274.2	nM	PMID[479200]
NPT8	Individual Protein	DNA polymerase iota	Homo sapiens	Potency	n.a.	2993.5	nM	PMID[479200]
NPT2	Others	Unspecified		Potency	n.a.	8912.5	nM	PMID[479198]
NPT20555	ORGANISM	SARS-CoV-2	Severe acute respiratory syndrome coronavirus 2	IC50	>	20000.0	nM	PMID[479201]
NPT20555	ORGANISM	SARS-CoV-2	Severe acute respiratory syndrome coronavirus 2	IC50	>	19952.62	nM	PMID[479201]

☑ Note for Activity Records:
☉ The quantitative biological activities were primarily integrated from ChEMBL (Version-30) database and were also directly collected from PubMed literature. PubMed PMID was provided as the reference link for each activity record.

Chemically structural similarity: I. Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes 4,3285 NPs with experimentally-derived bioactivity available in NPASS)

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules. Tc lies between [0, 1] where '1' indicates the highest similarity. What is Tanimoto coefficient

● The left chart: Distribution of similarity level between NPC25581 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	314
0.1-0.2	1314
0.2-0.3	3471
0.3-0.4	7998
0.4-0.5	10503
0.5-0.6	4553
0.6-0.7	9767
0.7-0.8	4356
0.8-0.85	299
0.85-0.9	102
0.9-0.95	13
0.95-1	7

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC18074
1.0	High Similarity	NPC5419
1.0	High Similarity	NPC61
0.9921	High Similarity	NPC168799
0.9921	High Similarity	NPC155209
0.992	High Similarity	NPC198388
0.947	High Similarity	NPC288452
0.947	High Similarity	NPC289690
0.9398	High Similarity	NPC38473
0.9323	High Similarity	NPC156709
0.9323	High Similarity	NPC179505
0.9237	High Similarity	NPC106406
0.9191	High Similarity	NPC160378
0.9173	High Similarity	NPC279676
0.9173	High Similarity	NPC67349
0.9154	High Similarity	NPC318799
0.912	High Similarity	NPC472271
0.912	High Similarity	NPC147654
0.9118	High Similarity	NPC37331
0.9118	High Similarity	NPC284948
0.9118	High Similarity	NPC220664
0.9118	High Similarity	NPC319628
0.9118	High Similarity	NPC303090
0.9111	High Similarity	NPC477279
0.9104	High Similarity	NPC302857
0.9104	High Similarity	NPC219428
0.9104	High Similarity	NPC152942
0.9104	High Similarity	NPC37250
0.9104	High Similarity	NPC278068
0.9104	High Similarity	NPC142703
0.9044	High Similarity	NPC13818
0.9044	High Similarity	NPC477277
0.9044	High Similarity	NPC477278
0.9044	High Similarity	NPC35702
0.9044	High Similarity	NPC206095
0.9044	High Similarity	NPC471027
0.9044	High Similarity	NPC477335
0.9044	High Similarity	NPC297517
0.9044	High Similarity	NPC224389
0.9037	High Similarity	NPC476819
0.9037	High Similarity	NPC303683
0.9037	High Similarity	NPC26241
0.9037	High Similarity	NPC205751
0.9037	High Similarity	NPC474875
0.9037	High Similarity	NPC295492
0.9037	High Similarity	NPC476820
0.9037	High Similarity	NPC274891
0.8993	High Similarity	NPC229264
0.8978	High Similarity	NPC277315
0.8978	High Similarity	NPC43158
0.8978	High Similarity	NPC258469
0.8978	High Similarity	NPC472016
0.8978	High Similarity	NPC192831
0.8931	High Similarity	NPC32626
0.8931	High Similarity	NPC217052
0.8931	High Similarity	NPC237506
0.8931	High Similarity	NPC329344
0.8929	High Similarity	NPC471076
0.8929	High Similarity	NPC192568
0.8906	High Similarity	NPC85565
0.8906	High Similarity	NPC288945
0.8889	High Similarity	NPC470849
0.8889	High Similarity	NPC470848
0.888	High Similarity	NPC263386
0.888	High Similarity	NPC141791
0.8872	High Similarity	NPC471749
0.8857	High Similarity	NPC221383
0.8857	High Similarity	NPC299090
0.8857	High Similarity	NPC143892
0.8857	High Similarity	NPC283081
0.8849	High Similarity	NPC477333
0.8824	High Similarity	NPC283560
0.8824	High Similarity	NPC284409
0.8824	High Similarity	NPC24295
0.8806	High Similarity	NPC68517
0.8803	High Similarity	NPC221091
0.8803	High Similarity	NPC259576
0.8741	High Similarity	NPC300329
0.8741	High Similarity	NPC182217
0.8741	High Similarity	NPC70680
0.8741	High Similarity	NPC233350
0.8723	High Similarity	NPC322660
0.8722	High Similarity	NPC108553
0.8714	High Similarity	NPC258671
0.8714	High Similarity	NPC53884
0.8696	High Similarity	NPC9218
0.8681	High Similarity	NPC246566
0.8681	High Similarity	NPC95498
0.8671	High Similarity	NPC32197
0.8667	High Similarity	NPC34293
0.8667	High Similarity	NPC886
0.8667	High Similarity	NPC248150
0.8667	High Similarity	NPC474895
0.8667	High Similarity	NPC135127
0.8667	High Similarity	NPC287597
0.8662	High Similarity	NPC98009
0.8652	High Similarity	NPC98356
0.8651	High Similarity	NPC63126
0.8651	High Similarity	NPC309434
0.8651	High Similarity	NPC275519
0.8643	High Similarity	NPC304956
0.8643	High Similarity	NPC474692
0.8621	High Similarity	NPC475145
0.8621	High Similarity	NPC44730
0.8621	High Similarity	NPC475162
0.8621	High Similarity	NPC475216
0.8621	High Similarity	NPC475595
0.8621	High Similarity	NPC266084
0.8621	High Similarity	NPC473544
0.8621	High Similarity	NPC83663
0.8611	High Similarity	NPC477334
0.8603	High Similarity	NPC123988
0.8601	High Similarity	NPC42464
0.8593	High Similarity	NPC475468
0.8571	High Similarity	NPC241354
0.8571	High Similarity	NPC285550
0.8571	High Similarity	NPC94810
0.855	High Similarity	NPC132921
0.8542	High Similarity	NPC306343
0.854	High Similarity	NPC90431
0.8538	High Similarity	NPC212541
0.8538	High Similarity	NPC14141
0.8531	High Similarity	NPC43123
0.8531	High Similarity	NPC472969
0.8527	High Similarity	NPC322332
0.8519	High Similarity	NPC327204
0.8519	High Similarity	NPC323379
0.8511	High Similarity	NPC22176
0.8511	High Similarity	NPC470130
0.8511	High Similarity	NPC190587
0.8511	High Similarity	NPC121573
0.8511	High Similarity	NPC226738
0.8511	High Similarity	NPC50221
0.8511	High Similarity	NPC114242
0.8511	High Similarity	NPC183824
0.8507	High Similarity	NPC285361
0.8504	High Similarity	NPC203124
0.85	High Similarity	NPC253722
0.85	High Similarity	NPC253481
0.85	High Similarity	NPC31751
0.8496	Intermediate Similarity	NPC110313
0.8496	Intermediate Similarity	NPC167463
0.8492	Intermediate Similarity	NPC277394
0.8492	Intermediate Similarity	NPC299252
0.8492	Intermediate Similarity	NPC61062
0.8492	Intermediate Similarity	NPC281277
0.8489	Intermediate Similarity	NPC322021
0.8485	Intermediate Similarity	NPC213552
0.8485	Intermediate Similarity	NPC475695
0.8485	Intermediate Similarity	NPC120225
0.8485	Intermediate Similarity	NPC168653
0.8485	Intermediate Similarity	NPC251407
0.8485	Intermediate Similarity	NPC118584
0.8478	Intermediate Similarity	NPC78363
0.8478	Intermediate Similarity	NPC84789
0.8478	Intermediate Similarity	NPC310252
0.8478	Intermediate Similarity	NPC100558
0.8478	Intermediate Similarity	NPC308976
0.8478	Intermediate Similarity	NPC260425
0.8478	Intermediate Similarity	NPC302583
0.8462	Intermediate Similarity	NPC86900
0.8456	Intermediate Similarity	NPC477281
0.8456	Intermediate Similarity	NPC477280
0.8456	Intermediate Similarity	NPC19719
0.8451	Intermediate Similarity	NPC228940
0.8446	Intermediate Similarity	NPC473275
0.8446	Intermediate Similarity	NPC470896
0.8438	Intermediate Similarity	NPC70084
0.8435	Intermediate Similarity	NPC477299
0.8433	Intermediate Similarity	NPC229784
0.8433	Intermediate Similarity	NPC83062
0.8433	Intermediate Similarity	NPC477294
0.8433	Intermediate Similarity	NPC64111
0.8433	Intermediate Similarity	NPC226855
0.8433	Intermediate Similarity	NPC477293
0.8425	Intermediate Similarity	NPC200988
0.8425	Intermediate Similarity	NPC163883
0.8425	Intermediate Similarity	NPC610
0.8425	Intermediate Similarity	NPC145023
0.8425	Intermediate Similarity	NPC175799
0.8425	Intermediate Similarity	NPC93498
0.8421	Intermediate Similarity	NPC276466
0.8421	Intermediate Similarity	NPC5018
0.8421	Intermediate Similarity	NPC123228
0.8421	Intermediate Similarity	NPC151167
0.8421	Intermediate Similarity	NPC123722
0.8421	Intermediate Similarity	NPC476873
0.8417	Intermediate Similarity	NPC205195
0.8417	Intermediate Similarity	NPC321638
0.8417	Intermediate Similarity	NPC321184
0.8417	Intermediate Similarity	NPC171134
0.8417	Intermediate Similarity	NPC472350
0.8417	Intermediate Similarity	NPC89105
0.8417	Intermediate Similarity	NPC328273
0.8417	Intermediate Similarity	NPC81515
0.8417	Intermediate Similarity	NPC476383
0.8417	Intermediate Similarity	NPC64141
0.8417	Intermediate Similarity	NPC197316
0.8417	Intermediate Similarity	NPC68092
0.8413	Intermediate Similarity	NPC233669

Chemically structural similarity: II. Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC25581 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	266
0.1-0.2	811
0.2-0.3	1609
0.3-0.4	2674
0.4-0.5	1978
0.5-0.6	1159
0.6-0.7	553
0.7-0.8	98
0.8-0.85	1
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9118	High Similarity	NPD6190	Approved
0.8417	Intermediate Similarity	NPD7266	Discontinued
0.8058	Intermediate Similarity	NPD230	Phase 1
0.7986	Intermediate Similarity	NPD8166	Discontinued
0.7985	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7961	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7919	Intermediate Similarity	NPD3455	Phase 2
0.7862	Intermediate Similarity	NPD4628	Phase 3
0.7843	Intermediate Similarity	NPD3882	Suspended
0.7842	Intermediate Similarity	NPD6798	Discontinued
0.7823	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7803	Intermediate Similarity	NPD9545	Approved
0.7801	Intermediate Similarity	NPD6355	Discontinued
0.7786	Intermediate Similarity	NPD6233	Phase 2
0.7786	Intermediate Similarity	NPD4062	Phase 3
0.7778	Intermediate Similarity	NPD3817	Phase 2
0.7714	Intermediate Similarity	NPD3764	Approved
0.7677	Intermediate Similarity	NPD7075	Discontinued
0.7643	Intermediate Similarity	NPD3027	Phase 3
0.7607	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7606	Intermediate Similarity	NPD4060	Phase 1
0.7593	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7584	Intermediate Similarity	NPD6799	Approved
0.7552	Intermediate Similarity	NPD4340	Discontinued
0.755	Intermediate Similarity	NPD5403	Approved
0.7548	Intermediate Similarity	NPD5402	Approved
0.7532	Intermediate Similarity	NPD1934	Approved
0.7519	Intermediate Similarity	NPD3022	Approved
0.7519	Intermediate Similarity	NPD3021	Approved
0.7518	Intermediate Similarity	NPD7095	Approved
0.7518	Intermediate Similarity	NPD9269	Phase 2
0.7516	Intermediate Similarity	NPD6234	Discontinued
0.75	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD9494	Approved
0.75	Intermediate Similarity	NPD6166	Phase 2
0.75	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD6797	Phase 2
0.7484	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD943	Approved
0.7483	Intermediate Similarity	NPD826	Approved
0.7483	Intermediate Similarity	NPD1512	Approved
0.7483	Intermediate Similarity	NPD825	Approved
0.747	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7463	Intermediate Similarity	NPD5536	Phase 2
0.7439	Intermediate Similarity	NPD7251	Discontinued
0.7419	Intermediate Similarity	NPD6801	Discontinued
0.7417	Intermediate Similarity	NPD5401	Approved
0.7407	Intermediate Similarity	NPD3818	Discontinued
0.7386	Intermediate Similarity	NPD1653	Approved
0.7383	Intermediate Similarity	NPD4110	Phase 3
0.7383	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7372	Intermediate Similarity	NPD2801	Approved
0.7368	Intermediate Similarity	NPD2629	Approved
0.7365	Intermediate Similarity	NPD4534	Discontinued
0.7365	Intermediate Similarity	NPD5958	Discontinued
0.7361	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7361	Intermediate Similarity	NPD1613	Approved
0.7351	Intermediate Similarity	NPD1511	Approved
0.7347	Intermediate Similarity	NPD2935	Discontinued
0.7343	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD7685	Pre-registration
0.7329	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD555	Phase 2
0.7308	Intermediate Similarity	NPD37	Approved
0.729	Intermediate Similarity	NPD4380	Phase 2
0.729	Intermediate Similarity	NPD6599	Discontinued
0.7289	Intermediate Similarity	NPD7808	Phase 3
0.7279	Intermediate Similarity	NPD1894	Discontinued
0.7278	Intermediate Similarity	NPD4967	Phase 2
0.7278	Intermediate Similarity	NPD4965	Approved
0.7278	Intermediate Similarity	NPD4966	Approved
0.7273	Intermediate Similarity	NPD228	Approved
0.7266	Intermediate Similarity	NPD1608	Approved
0.7261	Intermediate Similarity	NPD1465	Phase 2
0.7256	Intermediate Similarity	NPD7054	Approved
0.7244	Intermediate Similarity	NPD6385	Approved
0.7244	Intermediate Similarity	NPD6386	Approved
0.7231	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.723	Intermediate Similarity	NPD9570	Approved
0.723	Intermediate Similarity	NPD1501	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD9268	Approved
0.7212	Intermediate Similarity	NPD7074	Phase 3
0.7212	Intermediate Similarity	NPD7472	Approved
0.7205	Intermediate Similarity	NPD8127	Discontinued
0.7203	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7195	Intermediate Similarity	NPD7228	Approved
0.7194	Intermediate Similarity	NPD1535	Discovery
0.719	Intermediate Similarity	NPD3146	Approved
0.719	Intermediate Similarity	NPD3688	Clinical (unspecified phase)
0.7183	Intermediate Similarity	NPD258	Approved
0.7183	Intermediate Similarity	NPD257	Approved
0.7172	Intermediate Similarity	NPD259	Phase 1
0.7172	Intermediate Similarity	NPD6663	Approved
0.7162	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD6232	Discontinued
0.7152	Intermediate Similarity	NPD3750	Approved
0.7152	Intermediate Similarity	NPD5844	Phase 1
0.7143	Intermediate Similarity	NPD1481	Phase 2
0.7135	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD5736	Approved
0.7133	Intermediate Similarity	NPD9569	Approved
0.7125	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7121	Intermediate Similarity	NPD2067	Discontinued
0.7114	Intermediate Similarity	NPD1551	Phase 2
0.7114	Intermediate Similarity	NPD2438	Suspended
0.7111	Intermediate Similarity	NPD690	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD3887	Approved
0.7105	Intermediate Similarity	NPD2354	Approved
0.7099	Intermediate Similarity	NPD7199	Phase 2
0.7099	Intermediate Similarity	NPD1358	Approved
0.7078	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD447	Suspended
0.7067	Intermediate Similarity	NPD5763	Approved
0.7067	Intermediate Similarity	NPD5762	Approved
0.7067	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD4198	Discontinued
0.705	Intermediate Similarity	NPD17	Approved
0.7047	Intermediate Similarity	NPD1510	Phase 2
0.7044	Intermediate Similarity	NPD7819	Suspended
0.7042	Intermediate Similarity	NPD1283	Approved
0.7037	Intermediate Similarity	NPD5283	Phase 1
0.703	Intermediate Similarity	NPD7473	Discontinued
0.7024	Intermediate Similarity	NPD7038	Approved
0.7024	Intermediate Similarity	NPD7039	Approved
0.702	Intermediate Similarity	NPD1549	Phase 2
0.702	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7008	Intermediate Similarity	NPD9495	Approved
0.7007	Intermediate Similarity	NPD9493	Approved
0.7	Intermediate Similarity	NPD5408	Approved
0.7	Intermediate Similarity	NPD5405	Approved
0.7	Intermediate Similarity	NPD5404	Approved
0.7	Intermediate Similarity	NPD3847	Discontinued
0.7	Intermediate Similarity	NPD5406	Approved
0.6993	Remote Similarity	NPD1203	Approved
0.6993	Remote Similarity	NPD2797	Approved
0.6988	Remote Similarity	NPD3751	Discontinued
0.6975	Remote Similarity	NPD919	Approved
0.6968	Remote Similarity	NPD3536	Discontinued
0.6968	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD6832	Phase 2
0.6954	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD8455	Phase 2
0.6933	Remote Similarity	NPD2799	Discontinued
0.6933	Remote Similarity	NPD7033	Discontinued
0.6929	Remote Similarity	NPD1778	Approved
0.6928	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD3225	Approved
0.6923	Remote Similarity	NPD5049	Phase 3
0.6923	Remote Similarity	NPD6273	Approved
0.6923	Remote Similarity	NPD6559	Discontinued
0.6919	Remote Similarity	NPD8150	Discontinued
0.6918	Remote Similarity	NPD9537	Phase 1
0.6918	Remote Similarity	NPD7411	Suspended
0.6918	Remote Similarity	NPD9536	Phase 1
0.6913	Remote Similarity	NPD6653	Approved
0.6912	Remote Similarity	NPD1241	Discontinued
0.6905	Remote Similarity	NPD2934	Approved
0.6905	Remote Similarity	NPD2933	Approved
0.6903	Remote Similarity	NPD4357	Discontinued
0.6897	Remote Similarity	NPD2861	Phase 2
0.6894	Remote Similarity	NPD3134	Approved
0.6892	Remote Similarity	NPD3062	Approved
0.6892	Remote Similarity	NPD3059	Approved
0.6892	Remote Similarity	NPD1558	Phase 1
0.6892	Remote Similarity	NPD2979	Phase 3
0.6892	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6892	Remote Similarity	NPD3061	Approved
0.6892	Remote Similarity	NPD1240	Approved
0.6879	Remote Similarity	NPD3496	Discontinued
0.6875	Remote Similarity	NPD1164	Approved
0.6875	Remote Similarity	NPD1470	Approved
0.6871	Remote Similarity	NPD3268	Approved
0.687	Remote Similarity	NPD1237	Approved
0.6867	Remote Similarity	NPD4978	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD5585	Approved
0.6857	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6855	Remote Similarity	NPD4972	Discontinued
0.6853	Remote Similarity	NPD2983	Phase 2
0.6853	Remote Similarity	NPD2982	Phase 2
0.6852	Remote Similarity	NPD7768	Phase 2
0.685	Remote Similarity	NPD2859	Approved
0.685	Remote Similarity	NPD2860	Approved
0.6849	Remote Similarity	NPD2614	Approved
0.6848	Remote Similarity	NPD3787	Discontinued
0.6846	Remote Similarity	NPD274	Approved
0.6846	Remote Similarity	NPD1933	Approved
0.6846	Remote Similarity	NPD275	Approved
0.6842	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD2353	Approved
0.6839	Remote Similarity	NPD7440	Discontinued
0.6835	Remote Similarity	NPD3687	Approved
0.6835	Remote Similarity	NPD3686	Approved
0.6831	Remote Similarity	NPD1281	Approved

Bioactivity similarity: Similar Natural Products in NPASS

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