NPASS Compound

Natural Product: NPC128216

Natural Product ID	NPC128216
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	3,5-Dihydroxy-2-Phenylchromen-4-One
IUPAC Name	3,5-dihydroxy-2-phenylchromen-4-one
Synonyms	3,5,-Dihydroxyflavone
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL239276
PubChem CID	5393151
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001615] Flavones [CHEMONTID:0001136] Flavonols

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 29 31 0 0 0 0 0 0 0 0999 V2000 -4.0752 -1.9621 0.1422 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5147 -0.6752 0.0847 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3525 0.4233 0.0649 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7497 1.6603 0.0082 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3763 1.7803 -0.0264 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5495 0.6836 -0.0064 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1402 -0.5700 0.0506 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3026 -1.6594 0.0701 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8208 -2.8028 0.1216 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0863 -1.4666 0.0326 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6028 -0.2008 -0.0232 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2690 0.7851 -0.0383 O 0 0 0 0 0 0 0 0 0 0 0 0 2.0161 0.1200 -0.0657 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0189 -0.8092 -0.0555 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3348 -0.3569 -0.1005 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6521 0.9769 -0.1542 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6552 1.9331 -0.1655 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3680 1.4633 -0.1206 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8879 -2.6050 0.0546 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3366 -2.3848 1.0274 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4096 0.3192 0.0920 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3895 2.5312 -0.0081 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9682 2.7831 -0.0706 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8277 -1.8830 -0.0137 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1199 -1.1138 -0.0914 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6966 1.3057 -0.1889 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8473 2.9775 -0.2063 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5808 2.2186 -0.1295 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5600 -3.4715 -0.3374 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 5 6 1 0 6 7 2 0 7 8 1 0 8 9 2 0 8 10 1 0 10 11 2 0 11 12 1 0 11 13 1 0 13 14 2 0 14 15 1 0 15 16 2 0 16 17 1 0 17 18 2 0 10 19 1 0 7 2 1 0 18 13 1 0 12 6 1 0 1 20 1 0 3 21 1 0 4 22 1 0 5 23 1 0 14 24 1 0 15 25 1 0 16 26 1 0 17 27 1 0 18 28 1 0 19 29 1 0 M END

Standard InCHIKey	QHYWQIVTVQAKQF-UHFFFAOYSA-N
Standard InCHI	InChI=1S/C15H10O4/c16-10-7-4-8-11-12(10)13(17)14(18)15(19-11)9-5-2-1-3-6-9/h1-8,16,18H
SMILES	Oc1cccc2c1c(=O)c(c(o2)c1ccccc1)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	254.06	Volume:	256.396 ? Van der Waals volume.
Dense:	0.991	LogP:	2.707 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.499 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.473 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	1.0	Rigid Bonds:	18.0
TPSA:	70.67 ? Topological Polar Surface Area.	H-Bond Acceptor:	4.0
H-Bond Donor:	2.0	Rings:	3.0
Heavy Atoms:	4.0

MedChem Properties

QED Drug-Likeness Score:	0.7	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	2.069	Fsp³:	0.0
MCE-18:	16.0 ? 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:	Rejected	BMS Rule:	0
Chelating Alert:	1	PAINS Alert:	0
Colloidal aggregators:	0.545	Fluc inhibitor:	0.739 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.592 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.389 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.884	Promiscuous compounds:	0.77

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.862	MDCK Permeability:	-4.729
Pgp-inhibitor:	0.97	Pgp-substrate:	0.046
PAMPA:	0.405 ? 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):	0.008
20% Bioavailability (F20%):	0.014	30% Bioavailability (F30%):	0.518
50% Bioavailability (F50%):	0.866

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.077	MRP1:	0.92
Plasma Protein Binding (PPB):	98.949%	Volume Distribution (VD):	-0.741
Fu:	0.44% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.922
OATP1B3 inhibitor:	0.995	BCRP inhibitor:	0.911
BSEP inhibitor:	0.981

ADMET: Metabolism

CYP1A2-inhibitor:	0.286	CYP1A2-substrate:	0.879
CYP2C19-inhibitor:	0.001	CYP2C19-substrate:	0.988
CYP2C9-inhibitor:	0.997	CYP2C9-substrate:	0.017
CYP2D6-inhibitor:	0.911	CYP2D6-substrate:	0.001
CYP3A4-inhibitor:	0.016	CYP3A4-substrate:	0.593
CYP2B6-substrate:	0.001	CYP2C8-inhibitor:	0.849
HLM stability:	0.843 ? 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):

5.414

Half-life (T1/2):

0.931

ADMET: Toxicity

hERG Blockers:	0.064	hERG Blockers (10um):	0.45
Human Hepatotoxicity (H-HT):	0.441	Drug-induced Liver Injury (DILI):	0.852
AMES Toxicity:	0.548	Rat Oral Acute Toxicity:	0.49
Maximum Recommended Daily Dose:	0.54	Skin Sensitization:	0.558
Carcinogencity:	0.661	Eye Corrosion:	0.501
Eye Irritation:	0.99	Respiratory Toxicity:	0.707
Drug-induced Neurotoxicity:	0.082	Ototoxicity:	0.101
Hematotoxicity:	0.164	Drug-induced Nephrotoxicity:	0.092
Genotoxicity:	0.781	RPMI-8226 Immunitoxicity:	0.051
A549 Cytotoxicity:	0.198	Hek293 Cytotoxicity:	0.289
BCF:	1.115 ? 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:	4.184 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.987 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.68 ? 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
NPO22583	Daedaleopsis confragosa	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11014261]
NPO18557	Epicoccum nigrum	Species	Didymellaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17711348]
NPO18557	Epicoccum nigrum	Species	Didymellaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19919067]
NPO18557	Epicoccum nigrum	Species	Didymellaceae	Eukaryota	n.a.	The fungus is isolated from the leaves of L. rhodostegia, collected in June 2007 at Nanning, Guangxi Province, China	2007-JUN	PMID[20550196]
NPO15440	Chamaemelum nobile	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23501116]
NPO18557	Epicoccum nigrum	Species	Didymellaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24328302]
NPO15440	Chamaemelum nobile	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24471493]
NPO15440	Chamaemelum nobile	Species	Asteraceae	Eukaryota	Flowers	n.a.	n.a.	PMID[28116906]
NPO23957	Helleborus caucasicus	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24284	Hypoestes serpens	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17647	Schkuhria multiflora	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15440	Chamaemelum nobile	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18557	Epicoccum nigrum	Species	Didymellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24329	Primula farinosa	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24045	Lespedeza homoloba	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24216	Lolium perenne	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO23916	Anthocleista grandiflora	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15440	Chamaemelum nobile	Species	Asteraceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO15440	Chamaemelum nobile	Species	Asteraceae	Eukaryota	Flower	n.a.	n.a.	Database[FooDB]
NPO24045	Lespedeza homoloba	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24284	Hypoestes serpens	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15440	Chamaemelum nobile	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24045	Lespedeza homoloba	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18557	Epicoccum nigrum	Species	Didymellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[Title]
NPO24284	Hypoestes serpens	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24173	Plutella xylostella	Species	Plutellidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15440	Chamaemelum nobile	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16234	Orgyia australis postica	Species	Lymantriidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17647	Schkuhria multiflora	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23957	Helleborus caucasicus	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23916	Anthocleista grandiflora	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24216	Lolium perenne	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20617	Tilletia laevis	Species	Tilletiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24329	Primula farinosa	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22583	Daedaleopsis confragosa	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24045	Lespedeza homoloba	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18557	Epicoccum nigrum	Species	Didymellaceae	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	3
Potency	17
Ratio IC50	1
Activity	1
Inhibition	1

Activity Type	# Activity
Individual protein	18
Organism	1
Protein-protein interaction	1
Others	2
Non-molecular	1

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1119	Individual protein	Arachidonate 12-lipoxygenase	Homo sapiens	IC50	>	100000.0	nM	PMID[17869117]
NPT1139	Individual protein	Arachidonate 15-lipoxygenase, type II	Homo sapiens	IC50	>	100000.0	nM	PMID[17869117]
NPT149	Individual protein	Endoplasmic reticulum-associated amyloid beta-peptide-binding protein	Homo sapiens	Potency	=	25118.9	nM	PubChem BioAssay data set
NPT282	Individual protein	MAP kinase ERK2	Homo sapiens	Potency	=	39810.7	nM	PubChem BioAssay data set
NPT151	Individual protein	15-hydroxyprostaglandin dehydrogenase [NAD+]	Homo sapiens	Potency	=	5623.4	nM	PubChem BioAssay data set
NPT109	Individual protein	Cytochrome P450 3A4	Homo sapiens	Potency	=	12589.3	nM	PubChem BioAssay data set
NPT483	Individual protein	Prelamin-A/C	Homo sapiens	Potency	=	35481.3	nM	PubChem BioAssay data set
NPT531	Individual protein	Nuclear receptor ROR-gamma	Mus musculus	Potency	=	7943.3	nM	PubChem BioAssay data set
NPT531	Individual protein	Nuclear receptor ROR-gamma	Mus musculus	Potency	=	3981.1	nM	PubChem BioAssay data set
NPT48	Individual protein	Lysine-specific demethylase 4D-like	Homo sapiens	Potency	=	39810.7	nM	PubChem BioAssay data set
NPT792	Individual protein	Arachidonate 15-lipoxygenase	Homo sapiens	IC50	=	3300.0	nM	PMID[17869117]
NPT51	Individual protein	Microtubule-associated protein tau	Homo sapiens	Potency	=	5623.4	nM	PubChem BioAssay data set
NPT792	Individual protein	Arachidonate 15-lipoxygenase	Homo sapiens	Potency	=	1995.3	nM	PubChem BioAssay data set
NPT442	Individual protein	Ferritin light chain	Equus caballus	Potency	=	14125.4	nM	PubChem BioAssay data set
NPT197	Protein-protein interaction	Menin/Histone-lysine N-methyltransferase MLL	Homo sapiens	Potency	=	39810.7	nM	PubChem BioAssay data set
NPT45	Individual protein	Ubiquitin carboxyl-terminal hydrolase 2	Homo sapiens	Potency	=	12589.3	nM	PubChem BioAssay data set
NPT539	Individual protein	Cellular tumor antigen p53	Homo sapiens	Potency	=	31622.8	nM	PubChem BioAssay data set
NPT539	Individual protein	Cellular tumor antigen p53	Homo sapiens	Potency	=	3162.3	nM	PubChem BioAssay data set

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	Activity	=	58.3	%	PMID[20692831]
NPT191	Organism	Hepatitis C virus	Hepatitis C virus	Inhibition	=	83.66	%	PMID[22445328]
NPT2	Others	Unspecified	n.a.	Ratio IC50	<	0.03	n.a.	PMID[17869117]
NPT2	Others	Unspecified	n.a.	Potency	=	316.2	nM	PubChem BioAssay data set

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 NPC128216 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	35118
0.1-0.2	12522
0.2-0.3	1846
0.3-0.4	278
0.4-0.5	67
0.5-0.6	16
0.6-0.7	5
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
0.7021	Intermediate Similarity	NPC187432
0.6809	Remote Similarity	NPC93730
0.6458	Remote Similarity	NPC197425
0.6346	Remote Similarity	NPC152042
0.6	Remote Similarity	NPC116775
0.6	Remote Similarity	NPC299379
0.5849	Remote Similarity	NPC26227
0.5577	Remote Similarity	NPC20791
0.5472	Remote Similarity	NPC179271
0.5472	Remote Similarity	NPC603959
0.537	Remote Similarity	NPC256042
0.5357	Remote Similarity	NPC301123
0.5357	Remote Similarity	NPC143799
0.5283	Remote Similarity	NPC195351
0.5283	Remote Similarity	NPC169749
0.5263	Remote Similarity	NPC603348
0.5254	Remote Similarity	NPC114377
0.5094	Remote Similarity	NPC77858
0.5088	Remote Similarity	NPC87125
0.5088	Remote Similarity	NPC241838
0.5088	Remote Similarity	NPC605146
0.5088	Remote Similarity	NPC608038

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC128216 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6368
0.1-0.2	2698
0.2-0.3	77
0.3-0.4	6
0.4-0.5	0
0.5-0.6	1
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
0.5577	Remote Similarity	NPD1512	Phase 3

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