NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	210.05
Volume:	203.729
LogP:	2.014
LogD:	0.936
LogS:	-2.663
# Rotatable Bonds:	2
TPSA:	94.83
# H-Bond Aceptor:	5
# H-Bond Donor:	3
# Rings:	1
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.637
Synthetic Accessibility Score:	2.458
Fsp3:	0.2
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.966
MDCK Permeability:	9.51685979089234e-06
Pgp-inhibitor:	0.009
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.031
20% Bioavailability (F20%):	0.409
30% Bioavailability (F30%):	0.496

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.015
Plasma Protein Binding (PPB):	93.70198059082031%
Volume Distribution (VD):	0.872
Pgp-substrate:	6.391941547393799%

ADMET: Metabolism

CYP1A2-inhibitor:	0.921
CYP1A2-substrate:	0.31
CYP2C19-inhibitor:	0.122
CYP2C19-substrate:	0.057
CYP2C9-inhibitor:	0.466
CYP2C9-substrate:	0.605
CYP2D6-inhibitor:	0.514
CYP2D6-substrate:	0.204
CYP3A4-inhibitor:	0.594
CYP3A4-substrate:	0.156

ADMET: Excretion

Clearance (CL):	4.43
Half-life (T1/2):	0.767

ADMET: Toxicity

hERG Blockers:	0.027
Human Hepatotoxicity (H-HT):	0.065
Drug-inuced Liver Injury (DILI):	0.926
AMES Toxicity:	0.457
Rat Oral Acute Toxicity:	0.038
Maximum Recommended Daily Dose:	0.061
Skin Sensitization:	0.753
Carcinogencity:	0.059
Eye Corrosion:	0.038
Eye Irritation:	0.929
Respiratory Toxicity:	0.763

Download Data

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

Natural Product: NPC226275

Natural Product ID:	NPC226275
*Common Name:**	1-(3-Acetyl-2,4,6-Trihydroxyphenyl)Ethanone
IUPAC Name:	1-(3-acetyl-2,4,6-trihydroxyphenyl)ethanone
Synonyms:	2,4-Diacetyl Phloroglucinol
Standard InCHIKey:	PIFFQYJYNWXNGE-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C10H10O5/c1-4(11)8-6(13)3-7(14)9(5(2)12)10(8)15/h3,13-15H,1-2H3
SMILES:	CC(=O)c1c(cc(c(C(=O)C)c1O)O)O
Synthetic Gene Cluster:	BGC0000280;BGC0000281;
ChEMBL Identifier:	CHEMBL276139
PubChem CID:	16547
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0001831] Carbonyl compounds [CHEMONTID:0000118] Ketones [CHEMONTID:0003670] Aryl ketones [CHEMONTID:0004296] Phenylketones [CHEMONTID:0004298] Alkyl-phenylketones

*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
NPO8513	Pseudomonas fluorescens	Species	Pseudomonadaceae	Bacteria	n.a.	n.a.	n.a.	PMID[15826166]
NPO8513	Pseudomonas fluorescens	Species	Pseudomonadaceae	Bacteria	n.a.	n.a.	n.a.	PMID[17924666]
NPO29941	Lysobacter gummosus	Species	Xanthomonadaceae	Bacteria	n.a.	n.a.	n.a.	PMID[18058176]
NPO8513	Pseudomonas fluorescens	Species	Pseudomonadaceae	Bacteria	n.a.	n.a.	n.a.	PMID[20979386]
NPO8513	Pseudomonas fluorescens	Species	Pseudomonadaceae	Bacteria	n.a.	n.a.	n.a.	PMID[23688329]
NPO8513	Pseudomonas fluorescens	Species	Pseudomonadaceae	Bacteria	n.a.	n.a.	n.a.	PMID[23897464]
NPO31175	Pseudomonas protegens	Species	Pseudomonadaceae	Bacteria	n.a.	n.a.	n.a.	PMID[24742073]
NPO12957	Piper auritum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28704049]
NPO8513	Pseudomonas fluorescens	Species	Pseudomonadaceae	Bacteria	n.a.	n.a.	n.a.	PMID[7798954]
NPO8513	Pseudomonas fluorescens	Species	Pseudomonadaceae	Bacteria	n.a.	n.a.	n.a.	PMID[8626242]
NPO12957	Piper auritum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8513	Pseudomonas fluorescens	Species	Pseudomonadaceae	Bacteria	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	4
IC50	5
Others	10
Potency	29

Activity Type	# Activity
Cell Line	9
Individual Protein	23
Organism	8
Others	6
Uncleic Acid	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT80	Cell Line	Raji	Homo sapiens	Viability	=	60.0	%	PMID[572558]
NPT189	Cell Line	Vero	Chlorocebus aethiops	IC50	=	12.0	ug.mL-1	PMID[572559]
NPT857	Cell Line	LLC-PK1	Sus scrofa	IC50	=	11.0	ug.mL-1	PMID[572559]
NPT531	Individual Protein	Nuclear receptor ROR-gamma	Mus musculus	Potency	=	10000.0	nM	PMID[572560]
NPT54	Individual Protein	Nonstructural protein 1	Influenza A virus	Potency	=	10000.0	nM	PMID[572560]
NPT531	Individual Protein	Nuclear receptor ROR-gamma	Mus musculus	Potency	=	2818.4	nM	PMID[572560]
NPT1254	Individual Protein	Streptokinase A	Streptococcus pyogenes serotype M1	EC50	=	2635.0	nM	PMID[572560]
NPT152	Individual Protein	Nuclear factor erythroid 2-related factor 2	Homo sapiens	Potency	n.a.	25929.0	nM	PMID[572560]
NPT64	Individual Protein	ATPase family AAA domain-containing protein 5	Homo sapiens	Potency	n.a.	12990.0	nM	PMID[572560]
NPT65	Cell Line	HepG2	Homo sapiens	Potency	n.a.	3981.1	nM	PMID[572560]
NPT154	Individual Protein	Mothers against decapentaplegic homolog 3	Homo sapiens	Potency	n.a.	22387.2	nM	PMID[572560]
NPT369	Cell Line	ACHN	Homo sapiens	GI	=	44.0	%	PMID[572561]
NPT461	Cell Line	PANC-1	Homo sapiens	GI	=	0.0	%	PMID[572561]
NPT1307	Cell Line	Calu-1	Homo sapiens	GI	=	0.0	%	PMID[572561]
NPT397	Cell Line	NCI-H460	Homo sapiens	GI	=	25.0	%	PMID[572561]
NPT393	Cell Line	HCT-116	Homo sapiens	GI	=	0.0	%	PMID[572561]
NPT210	Individual Protein	Thyroid stimulating hormone receptor	Homo sapiens	Potency	n.a.	30131.3	nM	PMID[572560]
NPT1797	Individual Protein	Alpha trans-inducing protein (VP16)	Herpes simplex virus (type 1 / strain 17)	IC50	n.a.	4561.0	nM	PMID[572560]
NPT1798	Individual Protein	Photoreceptor-specific nuclear receptor	Homo sapiens	IC50	n.a.	3238.0	nM	PMID[572560]
NPT10	Individual Protein	Geminin	Homo sapiens	Potency	n.a.	1458.1	nM	PMID[572560]
NPT478	Individual Protein	Ataxin-2	Homo sapiens	Potency	n.a.	7079.5	nM	PMID[572560]
NPT101	Individual Protein	Glucagon-like peptide 1 receptor	Homo sapiens	Potency	n.a.	7943.3	nM	PMID[572560]
NPT50	Individual Protein	Tyrosyl-DNA phosphodiesterase 1	Homo sapiens	Potency	n.a.	25929.0	nM	PMID[572560]
NPT50	Individual Protein	Tyrosyl-DNA phosphodiesterase 1	Homo sapiens	Potency	n.a.	20596.2	nM	PMID[572560]
NPT160	Individual Protein	TAR DNA-binding protein 43	Homo sapiens	Potency	n.a.	35481.3	nM	PMID[572560]
NPT535	Individual Protein	Parathyroid hormone receptor	Homo sapiens	Potency	n.a.	50118.7	nM	PMID[572560]
NPT11	Individual Protein	Guanine nucleotide-binding protein G(s), subunit alpha	Homo sapiens	Potency	n.a.	35481.3	nM	PMID[572560]
NPT589	Individual Protein	Serum albumin	Bos taurus	Inhibition	=	83.0	%	PMID[572562]
NPT589	Individual Protein	Serum albumin	Bos taurus	EC50	=	6300000.0	nM	PMID[572562]
NPT938	Organism	Cavia porcellus	Cavia porcellus	Inhibition	=	44.3	%	PMID[572557]
NPT938	Organism	Cavia porcellus	Cavia porcellus	Inhibition	=	39.1	%	PMID[572557]
NPT633	Organism	Leishmania donovani	Leishmania donovani	IC50	=	27.0	ug.mL-1	PMID[572559]
NPT633	Organism	Leishmania donovani	Leishmania donovani	IC90	>	40.0	ug.mL-1	PMID[572559]
NPT174	Organism	Streptococcus	Streptococcus	EC50	=	3976.0	nM	PMID[572560]
NPT1252	Organism	Streptococcus sp. 'group A'	Streptococcus sp. 'group A'	EC50	=	3897.0	nM	PMID[572560]
NPT312	Organism	Saccharomyces cerevisiae	Saccharomyces cerevisiae	Potency	=	11220.2	nM	PMID[572560]
NPT536	Uncleic Acid	microRNA 21	Homo sapiens	Potency	=	26121.6	nM	PMID[572560]
NPT2	Others	Unspecified		Potency	=	16360.1	nM	PMID[572560]
NPT2	Others	Unspecified		Potency	n.a.	35481.3	nM	PMID[572560]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Potency	n.a.	10417.9	nM	PMID[572560]
NPT2	Others	Unspecified		Potency	n.a.	10000.0	nM	PMID[572560]
NPT2	Others	Unspecified		Potency	n.a.	3548.1	nM	PMID[572560]
NPT755	Individual Protein	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	Homo sapiens	Potency	n.a.	25118.9	nM	PMID[572560]
NPT2	Others	Unspecified		Potency	n.a.	18356.4	nM	PMID[572560]
NPT861	Individual Protein	Isocitrate dehydrogenase [NADP] cytoplasmic	Homo sapiens	Potency	n.a.	12995.3	nM	PMID[572560]
NPT920	Individual Protein	Alpha-synuclein	Homo sapiens	Potency	n.a.	15848.9	nM	PMID[572560]

☑ 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 NPC226275 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	326
0.1-0.2	1686
0.2-0.3	5027
0.3-0.4	12863
0.4-0.5	6075
0.5-0.6	6103
0.6-0.7	6023
0.7-0.8	3779
0.8-0.85	612
0.85-0.9	139
0.9-0.95	58
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
0.9655	High Similarity	NPC215392
0.9573	High Similarity	NPC91105
0.9492	High Similarity	NPC65761
0.9492	High Similarity	NPC472029
0.9483	High Similarity	NPC294037
0.9478	High Similarity	NPC209486
0.9478	High Similarity	NPC40649
0.9407	High Similarity	NPC309765
0.9402	High Similarity	NPC146642
0.9402	High Similarity	NPC149246
0.9333	High Similarity	NPC475733
0.9322	High Similarity	NPC303737
0.9256	High Similarity	NPC267846
0.9231	High Similarity	NPC161617
0.918	High Similarity	NPC23126
0.918	High Similarity	NPC98254
0.918	High Similarity	NPC169250
0.918	High Similarity	NPC100067
0.918	High Similarity	NPC30501
0.918	High Similarity	NPC103356
0.918	High Similarity	NPC72158
0.918	High Similarity	NPC116513
0.918	High Similarity	NPC105157
0.918	High Similarity	NPC162612
0.918	High Similarity	NPC190043
0.918	High Similarity	NPC266689
0.916	High Similarity	NPC242895
0.9106	High Similarity	NPC221777
0.9106	High Similarity	NPC473017
0.9106	High Similarity	NPC21305
0.9098	High Similarity	NPC62952
0.9083	High Similarity	NPC133909
0.9083	High Similarity	NPC218333
0.9083	High Similarity	NPC232708
0.9083	High Similarity	NPC32032
0.9048	High Similarity	NPC48036
0.904	High Similarity	NPC275504
0.9032	High Similarity	NPC474998
0.9032	High Similarity	NPC230818
0.9008	High Similarity	NPC306288
0.9	High Similarity	NPC143427
0.9	High Similarity	NPC73532
0.9	High Similarity	NPC224273
0.9	High Similarity	NPC156139
0.9	High Similarity	NPC19174
0.9	High Similarity	NPC115159
0.9	High Similarity	NPC267552
0.9	High Similarity	NPC45438
0.8976	High Similarity	NPC474519
0.8966	High Similarity	NPC118288
0.8966	High Similarity	NPC276111
0.896	High Similarity	NPC84772
0.8952	High Similarity	NPC41263
0.8917	High Similarity	NPC229649
0.8917	High Similarity	NPC297186
0.8898	High Similarity	NPC121259
0.8889	High Similarity	NPC324482
0.8889	High Similarity	NPC475042
0.888	High Similarity	NPC476119
0.8862	High Similarity	NPC10926
0.8862	High Similarity	NPC477454
0.8843	High Similarity	NPC196976
0.8833	High Similarity	NPC159525
0.8819	High Similarity	NPC27490
0.879	High Similarity	NPC473751
0.879	High Similarity	NPC328983
0.879	High Similarity	NPC8745
0.879	High Similarity	NPC473691
0.878	High Similarity	NPC13238
0.877	High Similarity	NPC66252
0.8769	High Similarity	NPC222633
0.875	High Similarity	NPC139074
0.875	High Similarity	NPC267205
0.875	High Similarity	NPC40524
0.875	High Similarity	NPC213485
0.875	High Similarity	NPC158222
0.8739	High Similarity	NPC230349
0.873	High Similarity	NPC69235
0.873	High Similarity	NPC212379
0.872	High Similarity	NPC305518
0.872	High Similarity	NPC128428
0.872	High Similarity	NPC329205
0.872	High Similarity	NPC316625
0.871	High Similarity	NPC262671
0.871	High Similarity	NPC201728
0.8682	High Similarity	NPC166480
0.8682	High Similarity	NPC93756
0.8682	High Similarity	NPC282780
0.8682	High Similarity	NPC108113
0.8672	High Similarity	NPC175738
0.8667	High Similarity	NPC241089
0.8661	High Similarity	NPC62219
0.8651	High Similarity	NPC470981
0.8636	High Similarity	NPC162939
0.8615	High Similarity	NPC278375
0.8615	High Similarity	NPC283590
0.8615	High Similarity	NPC61153
0.8615	High Similarity	NPC125920
0.8615	High Similarity	NPC470210
0.8615	High Similarity	NPC164136
0.8615	High Similarity	NPC130899
0.8615	High Similarity	NPC70859
0.8605	High Similarity	NPC285054
0.8605	High Similarity	NPC37299
0.8605	High Similarity	NPC180261
0.8605	High Similarity	NPC103105
0.8595	High Similarity	NPC188814
0.8595	High Similarity	NPC195262
0.8583	High Similarity	NPC102829
0.8583	High Similarity	NPC120488
0.8583	High Similarity	NPC92624
0.856	High Similarity	NPC290466
0.8559	High Similarity	NPC242136
0.855	High Similarity	NPC13575
0.855	High Similarity	NPC191976
0.855	High Similarity	NPC65005
0.855	High Similarity	NPC194764
0.855	High Similarity	NPC84699
0.855	High Similarity	NPC60667
0.855	High Similarity	NPC264112
0.855	High Similarity	NPC131039
0.855	High Similarity	NPC254847
0.8538	High Similarity	NPC475088
0.8516	High Similarity	NPC259942
0.8516	High Similarity	NPC247477
0.8516	High Similarity	NPC17840
0.8516	High Similarity	NPC21378
0.8516	High Similarity	NPC470987
0.8516	High Similarity	NPC233056
0.8512	High Similarity	NPC283844
0.8507	High Similarity	NPC16455
0.8507	High Similarity	NPC307990
0.8504	High Similarity	NPC186098
0.8504	High Similarity	NPC80694
0.8492	Intermediate Similarity	NPC95309
0.8485	Intermediate Similarity	NPC98115
0.8485	Intermediate Similarity	NPC65837
0.8485	Intermediate Similarity	NPC471905
0.8485	Intermediate Similarity	NPC156910
0.8485	Intermediate Similarity	NPC477242
0.8485	Intermediate Similarity	NPC186838
0.8485	Intermediate Similarity	NPC178467
0.8485	Intermediate Similarity	NPC150399
0.8485	Intermediate Similarity	NPC477243
0.8485	Intermediate Similarity	NPC274109
0.8485	Intermediate Similarity	NPC149372
0.8485	Intermediate Similarity	NPC477244
0.8485	Intermediate Similarity	NPC474771
0.8485	Intermediate Similarity	NPC53206
0.8485	Intermediate Similarity	NPC174999
0.8485	Intermediate Similarity	NPC53414
0.8485	Intermediate Similarity	NPC474849
0.8485	Intermediate Similarity	NPC249606
0.8485	Intermediate Similarity	NPC41461
0.8485	Intermediate Similarity	NPC1486
0.8485	Intermediate Similarity	NPC25287
0.8485	Intermediate Similarity	NPC12165
0.8485	Intermediate Similarity	NPC66349
0.8485	Intermediate Similarity	NPC168105
0.8473	Intermediate Similarity	NPC103842
0.8473	Intermediate Similarity	NPC290803
0.8455	Intermediate Similarity	NPC248363
0.845	Intermediate Similarity	NPC198249
0.845	Intermediate Similarity	NPC250057
0.845	Intermediate Similarity	NPC270369
0.845	Intermediate Similarity	NPC5515
0.8444	Intermediate Similarity	NPC193555
0.8438	Intermediate Similarity	NPC109123
0.8421	Intermediate Similarity	NPC317119
0.8421	Intermediate Similarity	NPC153979
0.8421	Intermediate Similarity	NPC475974
0.8421	Intermediate Similarity	NPC472419
0.8409	Intermediate Similarity	NPC158481
0.8409	Intermediate Similarity	NPC151113
0.8409	Intermediate Similarity	NPC156092
0.8409	Intermediate Similarity	NPC50455
0.8409	Intermediate Similarity	NPC118919
0.8403	Intermediate Similarity	NPC223004
0.8397	Intermediate Similarity	NPC18877
0.8397	Intermediate Similarity	NPC82225
0.8397	Intermediate Similarity	NPC28753
0.8397	Intermediate Similarity	NPC159623
0.8397	Intermediate Similarity	NPC204960
0.8397	Intermediate Similarity	NPC294593
0.8397	Intermediate Similarity	NPC20560
0.8397	Intermediate Similarity	NPC144051
0.8397	Intermediate Similarity	NPC44437
0.8385	Intermediate Similarity	NPC31872
0.8385	Intermediate Similarity	NPC262359
0.8385	Intermediate Similarity	NPC475589
0.8385	Intermediate Similarity	NPC473584
0.8385	Intermediate Similarity	NPC135801
0.8385	Intermediate Similarity	NPC185624
0.8385	Intermediate Similarity	NPC313618
0.8372	Intermediate Similarity	NPC26697
0.8372	Intermediate Similarity	NPC147757
0.837	Intermediate Similarity	NPC28337
0.837	Intermediate Similarity	NPC290550
0.8361	Intermediate Similarity	NPC273282
0.8361	Intermediate Similarity	NPC474890

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 NPC226275 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	311
0.1-0.2	1031
0.2-0.3	1768
0.3-0.4	3025
0.4-0.5	1817
0.5-0.6	885
0.6-0.7	224
0.7-0.8	82
0.8-0.85	6
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.855	High Similarity	NPD1509	Clinical (unspecified phase)
0.8385	Intermediate Similarity	NPD1240	Approved
0.8385	Intermediate Similarity	NPD943	Approved
0.8258	Intermediate Similarity	NPD1607	Approved
0.8134	Intermediate Similarity	NPD1510	Phase 2
0.8058	Intermediate Similarity	NPD7390	Discontinued
0.8015	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8015	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7985	Intermediate Similarity	NPD6651	Approved
0.7956	Intermediate Similarity	NPD1549	Phase 2
0.7899	Intermediate Similarity	NPD2800	Approved
0.7872	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7846	Intermediate Similarity	NPD1164	Approved
0.7833	Intermediate Similarity	NPD74	Approved
0.7833	Intermediate Similarity	NPD9266	Approved
0.7826	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7812	Intermediate Similarity	NPD1201	Approved
0.7793	Intermediate Similarity	NPD7411	Suspended
0.7778	Intermediate Similarity	NPD940	Approved
0.7778	Intermediate Similarity	NPD846	Approved
0.776	Intermediate Similarity	NPD9493	Approved
0.7755	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.775	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.775	Intermediate Similarity	NPD9264	Approved
0.775	Intermediate Similarity	NPD9263	Approved
0.775	Intermediate Similarity	NPD9267	Approved
0.771	Intermediate Similarity	NPD1470	Approved
0.7615	Intermediate Similarity	NPD9269	Phase 2
0.7603	Intermediate Similarity	NPD4380	Phase 2
0.7578	Intermediate Similarity	NPD9268	Approved
0.7568	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7552	Intermediate Similarity	NPD1511	Approved
0.7518	Intermediate Similarity	NPD1243	Approved
0.75	Intermediate Similarity	NPD2532	Approved
0.75	Intermediate Similarity	NPD2534	Approved
0.75	Intermediate Similarity	NPD2533	Approved
0.75	Intermediate Similarity	NPD9545	Approved
0.748	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.746	Intermediate Similarity	NPD9281	Approved
0.7448	Intermediate Similarity	NPD1512	Approved
0.7429	Intermediate Similarity	NPD5406	Approved
0.7429	Intermediate Similarity	NPD5408	Approved
0.7429	Intermediate Similarity	NPD5404	Approved
0.7429	Intermediate Similarity	NPD2935	Discontinued
0.7429	Intermediate Similarity	NPD2796	Approved
0.7429	Intermediate Similarity	NPD5405	Approved
0.7417	Intermediate Similarity	NPD7075	Discontinued
0.7417	Intermediate Similarity	NPD9261	Approved
0.7394	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD230	Phase 1
0.7383	Intermediate Similarity	NPD6801	Discontinued
0.7383	Intermediate Similarity	NPD1934	Approved
0.7355	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7348	Intermediate Similarity	NPD9717	Approved
0.7343	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD7819	Suspended
0.731	Intermediate Similarity	NPD6799	Approved
0.7279	Intermediate Similarity	NPD920	Approved
0.7273	Intermediate Similarity	NPD6959	Discontinued
0.7273	Intermediate Similarity	NPD2654	Approved
0.7222	Intermediate Similarity	NPD3750	Approved
0.7219	Intermediate Similarity	NPD2801	Approved
0.7185	Intermediate Similarity	NPD1203	Approved
0.7183	Intermediate Similarity	NPD1551	Phase 2
0.7133	Intermediate Similarity	NPD6599	Discontinued
0.7133	Intermediate Similarity	NPD2344	Approved
0.7124	Intermediate Similarity	NPD3882	Suspended
0.7124	Intermediate Similarity	NPD7768	Phase 2
0.7123	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD6232	Discontinued
0.7113	Intermediate Similarity	NPD2799	Discontinued
0.7089	Intermediate Similarity	NPD7473	Discontinued
0.7078	Intermediate Similarity	NPD3749	Approved
0.7078	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD4750	Phase 3
0.7059	Intermediate Similarity	NPD1809	Phase 2
0.705	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7015	Intermediate Similarity	NPD422	Phase 1
0.7	Intermediate Similarity	NPD7286	Phase 2
0.7	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.6967	Remote Similarity	NPD1242	Phase 1
0.6954	Remote Similarity	NPD3226	Approved
0.6943	Remote Similarity	NPD1247	Approved
0.6939	Remote Similarity	NPD2309	Approved
0.6929	Remote Similarity	NPD2313	Discontinued
0.6929	Remote Similarity	NPD3268	Approved
0.6918	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD6166	Phase 2
0.6918	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD5953	Discontinued
0.6913	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6891	Remote Similarity	NPD845	Approved
0.6884	Remote Similarity	NPD2798	Approved
0.6879	Remote Similarity	NPD520	Approved
0.6875	Remote Similarity	NPD3748	Approved
0.6852	Remote Similarity	NPD1729	Discontinued
0.6839	Remote Similarity	NPD3817	Phase 2
0.6829	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6828	Remote Similarity	NPD6100	Approved
0.6828	Remote Similarity	NPD6099	Approved
0.6815	Remote Similarity	NPD919	Approved
0.6809	Remote Similarity	NPD411	Approved
0.6809	Remote Similarity	NPD3764	Approved
0.6792	Remote Similarity	NPD5710	Approved
0.6792	Remote Similarity	NPD5711	Approved
0.679	Remote Similarity	NPD6020	Phase 2
0.6783	Remote Similarity	NPD447	Suspended
0.6779	Remote Similarity	NPD3300	Phase 2
0.6777	Remote Similarity	NPD2860	Approved
0.6777	Remote Similarity	NPD2859	Approved
0.6772	Remote Similarity	NPD5494	Approved
0.6765	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6759	Remote Similarity	NPD3299	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6748	Remote Similarity	NPD7074	Phase 3
0.6742	Remote Similarity	NPD256	Approved
0.6742	Remote Similarity	NPD255	Approved
0.6741	Remote Similarity	NPD2932	Approved
0.6741	Remote Similarity	NPD3019	Approved
0.6728	Remote Similarity	NPD3818	Discontinued
0.6719	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6716	Remote Similarity	NPD1759	Phase 1
0.6715	Remote Similarity	NPD3972	Approved
0.6711	Remote Similarity	NPD5403	Approved
0.6694	Remote Similarity	NPD2934	Approved
0.6694	Remote Similarity	NPD1432	Clinical (unspecified phase)
0.6694	Remote Similarity	NPD2933	Approved
0.6691	Remote Similarity	NPD3266	Approved
0.6691	Remote Similarity	NPD3267	Approved
0.669	Remote Similarity	NPD1296	Phase 2
0.6689	Remote Similarity	NPD5401	Approved
0.6688	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD7054	Approved
0.6667	Remote Similarity	NPD6832	Phase 2
0.6667	Remote Similarity	NPD1237	Approved
0.6667	Remote Similarity	NPD2346	Discontinued
0.6667	Remote Similarity	NPD1471	Phase 3
0.6667	Remote Similarity	NPD6559	Discontinued
0.6667	Remote Similarity	NPD1465	Phase 2
0.6646	Remote Similarity	NPD7472	Approved
0.6643	Remote Similarity	NPD1019	Discontinued
0.6642	Remote Similarity	NPD1758	Phase 1
0.6639	Remote Similarity	NPD844	Approved
0.6638	Remote Similarity	NPD111	Approved
0.6613	Remote Similarity	NPD3020	Approved
0.6606	Remote Similarity	NPD6797	Phase 2
0.6605	Remote Similarity	NPD2403	Approved
0.6596	Remote Similarity	NPD9494	Approved
0.6593	Remote Similarity	NPD1548	Phase 1
0.6591	Remote Similarity	NPD1241	Discontinued
0.6585	Remote Similarity	NPD288	Approved
0.6573	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD2797	Approved
0.6566	Remote Similarity	NPD7251	Discontinued
0.6565	Remote Similarity	NPD6124	Clinical (unspecified phase)
0.656	Remote Similarity	NPD289	Clinical (unspecified phase)
0.6547	Remote Similarity	NPD1755	Approved
0.6533	Remote Similarity	NPD3400	Discontinued
0.6533	Remote Similarity	NPD4628	Phase 3
0.6531	Remote Similarity	NPD4308	Phase 3
0.6527	Remote Similarity	NPD7808	Phase 3
0.6522	Remote Similarity	NPD1610	Phase 2
0.6519	Remote Similarity	NPD8438	Clinical (unspecified phase)
0.6516	Remote Similarity	NPD7458	Discontinued
0.65	Remote Similarity	NPD3225	Approved
0.65	Remote Similarity	NPD9258	Approved
0.65	Remote Similarity	NPD9256	Approved
0.6494	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6485	Remote Similarity	NPD5844	Phase 1
0.6475	Remote Similarity	NPD1608	Approved
0.6467	Remote Similarity	NPD6104	Discontinued
0.6466	Remote Similarity	NPD7159	Clinical (unspecified phase)
0.6457	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.6457	Remote Similarity	NPD1929	Approved
0.6457	Remote Similarity	NPD1930	Approved
0.6444	Remote Similarity	NPD9568	Approved
0.6442	Remote Similarity	NPD3926	Phase 2
0.6441	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6438	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6438	Remote Similarity	NPD5124	Phase 1
0.6437	Remote Similarity	NPD4363	Phase 3
0.6437	Remote Similarity	NPD4360	Phase 2
0.6435	Remote Similarity	NPD9093	Approved
0.6434	Remote Similarity	NPD4908	Phase 1
0.6429	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6424	Remote Similarity	NPD1196	Approved
0.6424	Remote Similarity	NPD7003	Approved
0.6419	Remote Similarity	NPD7033	Discontinued
0.6415	Remote Similarity	NPD2296	Approved
0.6415	Remote Similarity	NPD5402	Approved
0.6405	Remote Similarity	NPD1543	Discontinued
0.64	Remote Similarity	NPD4362	Clinical (unspecified phase)
0.64	Remote Similarity	NPD4361	Phase 2
0.6383	Remote Similarity	NPD1283	Approved
0.6383	Remote Similarity	NPD1876	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