NPASS Compound

Natural Product: NPC226275

Natural Product ID	NPC226275
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	1-(3-Acetyl-2,4,6-Trihydroxyphenyl)Ethanone
IUPAC Name	1-(3-acetyl-2,4,6-trihydroxyphenyl)ethanone
Synonyms	2,4-Diacetyl Phloroglucinol
Synthetic Gene Cluster	n.a.
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

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 25 25 0 0 0 0 0 0 0 0999 V2000 2.7306 1.8812 0.2943 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6286 0.4099 0.1255 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6799 -0.2747 0.1779 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3648 -0.2369 -0.0939 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2856 -1.6049 -0.2489 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0773 -2.2345 -0.4599 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0930 -1.4988 -0.5210 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0523 -0.1282 -0.3703 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3003 0.6172 -0.4397 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6559 1.0275 -1.5811 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.1469 0.9056 0.7449 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1694 0.4732 -0.1607 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1844 1.8482 -0.0126 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3217 -2.1331 -0.7349 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4607 -2.3776 -0.1912 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3709 2.4212 -0.6082 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1992 2.2152 1.2241 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7858 2.1931 0.4335 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0677 -3.3103 -0.5755 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5005 1.2420 1.5672 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7477 0.0085 0.9867 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8406 1.7421 0.4896 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1604 2.3401 0.8041 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8482 -2.4539 0.0676 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6627 -3.0722 -0.9174 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 2 0 2 4 1 0 4 5 2 0 5 6 1 0 6 7 2 0 7 8 1 0 8 9 1 0 9 10 2 0 9 11 1 0 8 12 2 0 12 13 1 0 7 14 1 0 5 15 1 0 12 4 1 0 1 16 1 0 1 17 1 0 1 18 1 0 6 19 1 0 11 20 1 0 11 21 1 0 11 22 1 0 13 23 1 0 14 24 1 0 15 25 1 0 M END

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

Calculated Properties

Physi-Chem Properties

MedChem Properties

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

ADMET: Distribution

ADMET: Metabolism

ADMET: Excretion

ADMET: Toxicity

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]
NPO8513	Pseudomonas fluorescens	Species	Pseudomonadaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12957	Piper auritum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO31175	Pseudomonas protegens	Species	Pseudomonadaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8513	Pseudomonas fluorescens	Species	Pseudomonadaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO12957	Piper auritum	Species	Piperaceae	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
Potency	27
EC50	4
IC50	5
Inhibition	3
Viability	1
IC90	1
GI	5

Activity Type	# Activity
Individual protein	21
Cell line	9
Organism	8
Nucleic acid	2
Others	6

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1254	Individual protein	Streptokinase A	Streptococcus pyogenes serotype M1	EC50	=	2635.0	nM	PubChem BioAssay data set
NPT152	Individual protein	Nuclear factor erythroid 2-related factor 2	Homo sapiens	Potency	n.a.	25929.0	nM	PubChem BioAssay data set
NPT154	Individual protein	Mothers against decapentaplegic homolog 3	Homo sapiens	Potency	n.a.	22387.2	nM	PubChem BioAssay data set
NPT210	Individual protein	Thyroid stimulating hormone receptor	Homo sapiens	Potency	n.a.	30131.3	nM	PubChem BioAssay data set
NPT1797	Individual protein	Alpha trans-inducing protein (VP16)	Herpes simplex virus (type 1 / strain 17)	IC50	n.a.	4561.0	nM	PubChem BioAssay data set
NPT1798	Individual protein	Photoreceptor-specific nuclear receptor	Homo sapiens	IC50	n.a.	3238.0	nM	PubChem BioAssay data set
NPT10	Individual protein	Geminin	Homo sapiens	Potency	n.a.	1458.1	nM	PubChem BioAssay data set
NPT101	Individual protein	Glucagon-like peptide 1 receptor	Homo sapiens	Potency	n.a.	7943.3	nM	PubChem BioAssay data set
NPT160	Individual protein	TAR DNA-binding protein 43	Homo sapiens	Potency	n.a.	35481.3	nM	PubChem BioAssay data set
NPT11	Individual protein	Guanine nucleotide-binding protein G(s), subunit alpha	Homo sapiens	Potency	n.a.	35481.3	nM	PubChem BioAssay data set
NPT531	Individual protein	Nuclear receptor ROR-gamma	Mus musculus	Potency	=	10000.0	nM	PubChem BioAssay data set
NPT531	Individual protein	Nuclear receptor ROR-gamma	Mus musculus	Potency	=	2818.4	nM	PubChem BioAssay data set
NPT54	Individual protein	Nonstructural protein 1	Influenza A virus	Potency	=	10000.0	nM	PubChem BioAssay data set
NPT589	Individual protein	Serum albumin	Bos taurus	Inhibition	=	83.0	%	PMID[28704049]
NPT589	Individual protein	Serum albumin	Bos taurus	EC50	=	6300000.0	nM	PMID[28704049]
NPT478	Individual protein	Ataxin-2	Homo sapiens	Potency	n.a.	7079.5	nM	PubChem BioAssay data set
NPT755	Individual protein	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	Homo sapiens	Potency	n.a.	25118.9	nM	PubChem BioAssay data set
NPT861	Individual protein	Isocitrate dehydrogenase [NADP] cytoplasmic	Homo sapiens	Potency	n.a.	12995.3	nM	PubChem BioAssay data set
NPT920	Individual protein	Alpha-synuclein	Homo sapiens	Potency	n.a.	15848.9	nM	PubChem BioAssay data set
NPT535	Individual protein	Parathyroid hormone receptor	Homo sapiens	Potency	n.a.	50118.7	nM	PubChem BioAssay data set
NPT536	Nucleic acid	microRNA 21	Homo sapiens	Potency	=	26121.6	nM	PubChem BioAssay data set
NPT64	Individual protein	ATPase family AAA domain-containing protein 5	Homo sapiens	Potency	n.a.	12990.0	nM	PubChem BioAssay data set

In vitro activity

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[15913998]
NPT189	Cell line	Vero	Chlorocebus aethiops	IC50	=	12.0	ug.mL-1	PMID[17070063]
NPT857	Cell line	LLC-PK1	Sus scrofa	IC50	=	11.0	ug.mL-1	PMID[17070063]
NPT65	Cell line	HepG2	Homo sapiens	Potency	n.a.	3981.1	nM	PubChem BioAssay data set
NPT369	Cell line	ACHN	Homo sapiens	GI	=	44.0	%	PMID[22342146]
NPT461	Cell line	PANC-1	Homo sapiens	GI	=	0.0	%	PMID[22342146]
NPT1307	Cell line	Calu-1	Homo sapiens	GI	=	0.0	%	PMID[22342146]
NPT397	Cell line	NCI-H460	Homo sapiens	GI	=	25.0	%	PMID[22342146]
NPT393	Cell line	HCT-116	Homo sapiens	GI	=	0.0	%	PMID[22342146]
NPT174	Organism	Streptococcus	Streptococcus	EC50	=	3976.0	nM	PubChem BioAssay data set
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Potency	n.a.	10417.9	nM	PubChem BioAssay data set
NPT633	Organism	Leishmania donovani	Leishmania donovani	IC50	=	27.0	ug.mL-1	PMID[17070063]
NPT633	Organism	Leishmania donovani	Leishmania donovani	IC90	>	40.0	ug.mL-1	PMID[17070063]
NPT1252	Organism	Streptococcus sp. 'group A'	Streptococcus sp. 'group A'	EC50	=	3897.0	nM	PubChem BioAssay data set
NPT312	Organism	Saccharomyces cerevisiae	Saccharomyces cerevisiae	Potency	=	11220.2	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	=	16360.1	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	n.a.	35481.3	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	n.a.	10000.0	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	n.a.	3548.1	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	n.a.	18356.4	nM	PubChem BioAssay data set

In vivo activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT938	Organism	Cavia porcellus	Cavia porcellus	Inhibition	=	44.3	%	PMID[1560434]
NPT938	Organism	Cavia porcellus	Cavia porcellus	Inhibition	=	39.1	%	PMID[1560434]

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 NPC226275 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	23835
0.1-0.2	21844
0.2-0.3	3947
0.3-0.4	206
0.4-0.5	20
0.5-0.6	3
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	NPC209486
0.6129	Remote Similarity	NPC215392
0.56	Remote Similarity	NPC118288
0.5357	Remote Similarity	NPC294037
0.5185	Remote Similarity	NPC232708

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>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4029
0.1-0.2	4923
0.2-0.3	193
0.3-0.4	5
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