NPASS Compound

Structure

CID274121 OpenBabel06191716082D 21 23 0 0 0 0 0 0 0 0999 V2000 3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 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 3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 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 0.0000 -2.0000 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 -0.8660 -0.5000 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 4.3301 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -3.0000 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 -0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 0 0 0 1 7 1 0 0 0 0 2 9 1 0 0 0 0 3 7 2 0 0 0 0 3 10 1 0 0 0 0 4 8 2 0 0 0 0 4 11 1 0 0 0 0 5 8 1 0 0 0 0 5 14 2 0 0 0 0 6 12 1 0 0 0 0 6 13 2 0 0 0 0 7 16 1 0 0 0 0 8 17 1 0 0 0 0 9 10 2 0 0 0 0 9 13 1 0 0 0 0 10 18 1 0 0 0 0 11 15 2 0 0 0 0 11 19 1 0 0 0 0 12 15 1 0 0 0 0 12 20 2 0 0 0 0 13 21 1 0 0 0 0 14 15 1 0 0 0 0 14 21 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	286.05
Volume:	273.977
LogP:	2.885
LogD:	2.478
LogS:	-3.583
# Rotatable Bonds:	1
TPSA:	111.13
# H-Bond Aceptor:	6
# H-Bond Donor:	4
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.546
Synthetic Accessibility Score:	2.513
Fsp3:	0.0
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:	-5.008
MDCK Permeability:	9.970278370019514e-06
Pgp-inhibitor:	0.006
Pgp-substrate:	0.218
Human Intestinal Absorption (HIA):	0.025
20% Bioavailability (F20%):	0.999
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.009
Plasma Protein Binding (PPB):	95.9843521118164%
Volume Distribution (VD):	0.533
Pgp-substrate:	5.171061038970947%

ADMET: Metabolism

CYP1A2-inhibitor:	0.984
CYP1A2-substrate:	0.158
CYP2C19-inhibitor:	0.234
CYP2C19-substrate:	0.046
CYP2C9-inhibitor:	0.631
CYP2C9-substrate:	0.913
CYP2D6-inhibitor:	0.697
CYP2D6-substrate:	0.604
CYP3A4-inhibitor:	0.797
CYP3A4-substrate:	0.086

ADMET: Excretion

Clearance (CL):	7.637
Half-life (T1/2):	0.901

ADMET: Toxicity

hERG Blockers:	0.115
Human Hepatotoxicity (H-HT):	0.074
Drug-inuced Liver Injury (DILI):	0.917
AMES Toxicity:	0.466
Rat Oral Acute Toxicity:	0.037
Maximum Recommended Daily Dose:	0.709
Skin Sensitization:	0.925
Carcinogencity:	0.044
Eye Corrosion:	0.009
Eye Irritation:	0.936
Respiratory Toxicity:	0.151

Download Data

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

Natural Product: NPC274121

Natural Product ID:	NPC274121
*Common Name:**	Norartocarpetin
IUPAC Name:	2-(2,4-dihydroxyphenyl)-5,7-dihydroxychromen-4-one
Synonyms:	Norartocarpetin
Standard InCHIKey:	ZSYPIPFQOQGYHH-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C15H10O6/c16-7-1-2-9(10(18)3-7)13-6-12(20)15-11(19)4-8(17)5-14(15)21-13/h1-6,16-19H
SMILES:	Oc1ccc(c(c1)O)c1cc(=O)c2c(o1)cc(cc2O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL463145
PubChem CID:	5481970
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001615] Flavones

*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
NPO17767	Artocarpus heterophyllus	Species	Moraceae	Eukaryota	n.a.	root	n.a.	DOI[10.1016/0031-9422(95)00135-T]
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10654410]
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	n.a.	root	n.a.	PMID[10843587]
NPO11740	Sagenomella striatispora	Species	Trichocomaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10869218]
NPO10498	Artocarpus dadah	Species	Moraceae	Eukaryota	bark and twigs	Tewah, Central Kalimantan, Indonesia (N 38 57.003; W 094 44.767)	1999-Oct	PMID[11858749]
NPO11740	Sagenomella striatispora	Species	Trichocomaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15217294]
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	Roots	n.a.	n.a.	PMID[15568770]
NPO30804	Cudrania tricuspidata	Species	Moraceae	Eukaryota	n.a.	root	n.a.	PMID[15787460]
NPO30804	Cudrania tricuspidata	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15787460]
NPO30804	Cudrania tricuspidata	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16203143]
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	n.a.	root	n.a.	PMID[16392664]
NPO30804	Cudrania tricuspidata	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16919944]
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	n.a.	root	n.a.	PMID[16933887]
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	roots	Hualien Hsien, Taiwan	2003-JUL	PMID[16933887]
NPO16194	Morus bombycis	Species	Moraceae	Eukaryota	n.a.	root	n.a.	PMID[17396934]
NPO30804	Cudrania tricuspidata	Species	Moraceae	Eukaryota	root bark	n.a.	n.a.	PMID[17608532]
NPO30804	Cudrania tricuspidata	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17950599]
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	n.a.	root	n.a.	PMID[17951038]
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18175961]
NPO30804	Cudrania tricuspidata	Species	Moraceae	Eukaryota	fruits	n.a.	n.a.	PMID[19113968]
NPO30804	Cudrania tricuspidata	Species	Moraceae	Eukaryota	Roots	n.a.	n.a.	PMID[19191562]
NPO30804	Cudrania tricuspidata	Species	Moraceae	Eukaryota	n.a.	root	n.a.	PMID[19280148]
NPO30804	Cudrania tricuspidata	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19285413]
NPO30804	Cudrania tricuspidata	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19660948]
NPO32569	artocarpus rigida	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20384315]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20815207]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	leaf	n.a.	PMID[21319773]
NPO30804	Cudrania tricuspidata	Species	Moraceae	Eukaryota	n.a.	root	n.a.	PMID[21319773]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	bark	n.a.	PMID[21319773]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	root	n.a.	PMID[21319773]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	leaf	n.a.	PMID[22207282]
NPO17767	Artocarpus heterophyllus	Species	Moraceae	Eukaryota	Wood	n.a.	n.a.	PMID[23113717]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	root	n.a.	PMID[23806866]
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24295087]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	Konya, Turkey	2007-APR	PMID[24901948]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	root bark	University of Veterinary and Pharmaceutical Sciences Brno (UVPS Brno), Brno, Czech Republic	2011-APR	PMID[24901948]
NPO30804	Cudrania tricuspidata	Species	Moraceae	Eukaryota	Roots	n.a.	n.a.	PMID[25322455]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	leaves	Chungbuk, Korea	n.a.	PMID[25935644]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	root	n.a.	PMID[25981820]
NPO30804	Cudrania tricuspidata	Species	Moraceae	Eukaryota	root barks	purchased from the local herbal market, Chungbuk, Korea	2012-JUL	PMID[26227773]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	latex	n.a.	PMID[27294120]
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27575476]
NPO32569	artocarpus rigida	Species	Moraceae	Eukaryota	Stems	n.a.	n.a.	PMID[29227656]
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	Roots	n.a.	n.a.	PMID[30298740]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	Root barks	n.a.	n.a.	PMID[3097265]
NPO17767	Artocarpus heterophyllus	Species	Moraceae	Eukaryota	n.a.	formosan	n.a.	PMID[8864236]
NPO16194	Morus bombycis	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9544568]
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	Roots	n.a.	n.a.	PMID[9868163]
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	n.a.	root	n.a.	Database[Article]
NPO17767	Artocarpus heterophyllus	Species	Moraceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO17767	Artocarpus heterophyllus	Species	Moraceae	Eukaryota	Latex Exudate	n.a.	n.a.	Database[FooDB]
NPO17767	Artocarpus heterophyllus	Species	Moraceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO17767	Artocarpus heterophyllus	Species	Moraceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO10498	Artocarpus dadah	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17767	Artocarpus heterophyllus	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO16194	Morus bombycis	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO30804	Cudrania tricuspidata	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8352	Canthium berberidifolium	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10498	Artocarpus dadah	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16194	Morus bombycis	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17767	Artocarpus heterophyllus	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO16194	Morus bombycis	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO30804	Cudrania tricuspidata	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO16194	Morus bombycis	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO17767	Artocarpus heterophyllus	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10498	Artocarpus dadah	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8352	Canthium berberidifolium	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16194	Morus bombycis	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11740	Sagenomella striatispora	Species	Trichocomaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28265	Morus alba	Species	Moraceae	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
IC50	14
Ki	2
Others	8

Activity Type	# Activity
Cell Line	1
Individual Protein	13
Others	7
SINGLE PROTEIN	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT30	Individual Protein	Cyclooxygenase-1	Homo sapiens	IC50	=	14000.0	nM	PMID[489942]
NPT31	Individual Protein	Cyclooxygenase-2	Homo sapiens	IC50	>	100000.0	nM	PMID[489942]
NPT43	Individual Protein	Tyrosinase	Agaricus bisporus	IC50	>	200000.0	nM	PMID[489945]
NPT1120	Individual Protein	Pancreatic triacylglycerol lipase	Sus scrofa	Inhibition	=	45.3	%	PMID[489946]
NPT1120	Individual Protein	Pancreatic triacylglycerol lipase	Sus scrofa	IC50	>	70000.0	nM	PMID[489946]
NPT3997	Individual Protein	Hematopoietic cell protein-tyrosine phosphatase 70Z-PEP	Homo sapiens	IC50	=	30290.0	nM	PMID[489948]
NPT178	Individual Protein	Protein-tyrosine phosphatase 1B	Homo sapiens	IC50	=	5180.0	nM	PMID[489948]
NPT3985	Individual Protein	Probable low molecular weight protein-tyrosine-phosphatase	Mycobacterium tuberculosis	IC50	=	11970.0	nM	PMID[489948]
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	6.1	ug.mL-1	PMID[489949]
NPT3102	Individual Protein	Beta-glucuronidase	Rattus norvegicus	Inhibition	=	67.7	%	PMID[489950]
NPT2	Others	Unspecified		Inhibition	=	85.2	%	PMID[489942]
NPT2	Others	Unspecified		IC50	=	1130.0	nM	PMID[489943]
NPT2	Others	Unspecified		Ki	=	1960.0	nM	PMID[489943]
NPT740	Individual Protein	Beta-secretase 1	Homo sapiens	Ki	=	82600.0	nM	PMID[489944]
NPT740	Individual Protein	Beta-secretase 1	Homo sapiens	IC50	=	60600.0	nM	PMID[489944]
NPT741	Individual Protein	Tyrosinase	Homo sapiens	IC50	=	23.0	nM	PMID[489947]
NPT741	Individual Protein	Tyrosinase	Homo sapiens	Ratio IC50	=	1900.0	n.a.	PMID[489947]
NPT22768	SINGLE PROTEIN	Phosphotyrosine protein phosphatase	Mycobacterium tuberculosis	IC50	=	1202.26	nM	PMID[489948]
NPT2	Others	Unspecified		Ratio IC50	=	17.5	n.a.	PMID[489948]
NPT24759	SINGLE PROTEIN	Protein-tyrosine phosphatase G1	Homo sapiens	IC50	=	20940.0	nM	PMID[489948]
NPT2	Others	Unspecified		Ratio IC50	=	25.2	n.a.	PMID[489948]
NPT2	Others	Unspecified		Ratio IC50	=	4.3	n.a.	PMID[489948]
NPT2	Others	Unspecified		Ratio IC50	=	10.0	n.a.	PMID[489948]
NPT22768	SINGLE PROTEIN	Phosphotyrosine protein phosphatase	Mycobacterium tuberculosis	IC50	=	1200.0	nM	PMID[489948]

☑ 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 NPC274121 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	507
0.1-0.2	2151
0.2-0.3	5519
0.3-0.4	12213
0.4-0.5	4665
0.5-0.6	4711
0.6-0.7	5641
0.7-0.8	4006
0.8-0.85	1712
0.85-0.9	1215
0.9-0.95	309
0.95-1	48

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC50898
1.0	High Similarity	NPC213216
1.0	High Similarity	NPC78540
0.9922	High Similarity	NPC172262
0.9844	High Similarity	NPC57601
0.9843	High Similarity	NPC113006
0.9769	High Similarity	NPC281917
0.9769	High Similarity	NPC231772
0.9769	High Similarity	NPC13408
0.9769	High Similarity	NPC116775
0.9769	High Similarity	NPC127447
0.9769	High Similarity	NPC187432
0.9769	High Similarity	NPC194281
0.9769	High Similarity	NPC29353
0.9769	High Similarity	NPC47815
0.9769	High Similarity	NPC124784
0.9769	High Similarity	NPC473887
0.9769	High Similarity	NPC256042
0.9769	High Similarity	NPC216361
0.9769	High Similarity	NPC234133
0.9695	High Similarity	NPC299379
0.9695	High Similarity	NPC266597
0.9695	High Similarity	NPC250266
0.9692	High Similarity	NPC239495
0.9692	High Similarity	NPC9985
0.9621	High Similarity	NPC201395
0.9615	High Similarity	NPC248872
0.9609	High Similarity	NPC5515
0.9609	High Similarity	NPC270369
0.9609	High Similarity	NPC137264
0.9606	High Similarity	NPC197425
0.9549	High Similarity	NPC216978
0.9549	High Similarity	NPC18260
0.9549	High Similarity	NPC152042
0.9549	High Similarity	NPC55018
0.9549	High Similarity	NPC301217
0.9549	High Similarity	NPC303633
0.9549	High Similarity	NPC143799
0.9549	High Similarity	NPC220062
0.9549	High Similarity	NPC241838
0.9549	High Similarity	NPC78913
0.9549	High Similarity	NPC96565
0.9545	High Similarity	NPC295261
0.9545	High Similarity	NPC287246
0.9545	High Similarity	NPC107586
0.9545	High Similarity	NPC290291
0.9545	High Similarity	NPC32441
0.9545	High Similarity	NPC275055
0.9545	High Similarity	NPC228661
0.9545	High Similarity	NPC79943
0.9545	High Similarity	NPC12296
0.9545	High Similarity	NPC296490
0.9545	High Similarity	NPC13768
0.9545	High Similarity	NPC243083
0.9535	High Similarity	NPC31872
0.9535	High Similarity	NPC473584
0.9535	High Similarity	NPC475589
0.9531	High Similarity	NPC39753
0.9531	High Similarity	NPC115998
0.9478	High Similarity	NPC59951
0.9478	High Similarity	NPC103342
0.9478	High Similarity	NPC103904
0.9478	High Similarity	NPC184536
0.9478	High Similarity	NPC146679
0.9478	High Similarity	NPC159275
0.9478	High Similarity	NPC281207
0.9478	High Similarity	NPC269652
0.9478	High Similarity	NPC261227
0.9478	High Similarity	NPC241100
0.9478	High Similarity	NPC270883
0.9478	High Similarity	NPC230285
0.9478	High Similarity	NPC172986
0.9474	High Similarity	NPC472460
0.9474	High Similarity	NPC99333
0.9474	High Similarity	NPC118813
0.9474	High Similarity	NPC147686
0.9474	High Similarity	NPC280284
0.9474	High Similarity	NPC188947
0.9474	High Similarity	NPC329225
0.9462	High Similarity	NPC25937
0.9462	High Similarity	NPC10971
0.9462	High Similarity	NPC128216
0.9407	High Similarity	NPC147688
0.9407	High Similarity	NPC136840
0.9407	High Similarity	NPC282300
0.9407	High Similarity	NPC262094
0.9407	High Similarity	NPC90582
0.9407	High Similarity	NPC156590
0.9407	High Similarity	NPC64908
0.9407	High Similarity	NPC14871
0.9407	High Similarity	NPC110969
0.9407	High Similarity	NPC118840
0.9407	High Similarity	NPC205006
0.9403	High Similarity	NPC222342
0.9403	High Similarity	NPC150648
0.9403	High Similarity	NPC53181
0.9403	High Similarity	NPC225153
0.9403	High Similarity	NPC20709
0.9403	High Similarity	NPC316480
0.9403	High Similarity	NPC217186
0.9403	High Similarity	NPC261234
0.9403	High Similarity	NPC265871
0.9403	High Similarity	NPC274784
0.9403	High Similarity	NPC310135
0.9403	High Similarity	NPC329203
0.9398	High Similarity	NPC254841
0.9398	High Similarity	NPC476480
0.9398	High Similarity	NPC160972
0.9398	High Similarity	NPC84585
0.9398	High Similarity	NPC188879
0.9394	High Similarity	NPC39426
0.9394	High Similarity	NPC234560
0.9389	High Similarity	NPC93756
0.9389	High Similarity	NPC108113
0.9389	High Similarity	NPC223457
0.9385	High Similarity	NPC278556
0.9338	High Similarity	NPC299080
0.9338	High Similarity	NPC214236
0.9338	High Similarity	NPC11561
0.9338	High Similarity	NPC473042
0.9338	High Similarity	NPC78803
0.9338	High Similarity	NPC59739
0.9338	High Similarity	NPC200694
0.9338	High Similarity	NPC62840
0.9338	High Similarity	NPC293852
0.9338	High Similarity	NPC226636
0.9338	High Similarity	NPC217083
0.9333	High Similarity	NPC6407
0.9333	High Similarity	NPC129853
0.9333	High Similarity	NPC475680
0.9333	High Similarity	NPC110228
0.9333	High Similarity	NPC150522
0.9333	High Similarity	NPC69769
0.9333	High Similarity	NPC235239
0.9333	High Similarity	NPC76445
0.9333	High Similarity	NPC284550
0.9333	High Similarity	NPC305355
0.9333	High Similarity	NPC188243
0.9328	High Similarity	NPC124269
0.9328	High Similarity	NPC276905
0.9323	High Similarity	NPC240593
0.9323	High Similarity	NPC87545
0.9323	High Similarity	NPC235428
0.9318	High Similarity	NPC125920
0.9313	High Similarity	NPC129132
0.9313	High Similarity	NPC87231
0.9313	High Similarity	NPC101294
0.9313	High Similarity	NPC205468
0.9313	High Similarity	NPC212631
0.9313	High Similarity	NPC473655
0.9313	High Similarity	NPC257756
0.9297	High Similarity	NPC22783
0.927	High Similarity	NPC470216
0.927	High Similarity	NPC293053
0.927	High Similarity	NPC9117
0.927	High Similarity	NPC219915
0.927	High Similarity	NPC24821
0.927	High Similarity	NPC279121
0.927	High Similarity	NPC190637
0.927	High Similarity	NPC11700
0.927	High Similarity	NPC38219
0.927	High Similarity	NPC212932
0.9265	High Similarity	NPC312391
0.9265	High Similarity	NPC3188
0.9265	High Similarity	NPC324386
0.9265	High Similarity	NPC4743
0.9265	High Similarity	NPC213322
0.9265	High Similarity	NPC103362
0.9259	High Similarity	NPC140890
0.9254	High Similarity	NPC303644
0.9254	High Similarity	NPC162680
0.9254	High Similarity	NPC181124
0.9254	High Similarity	NPC116632
0.9254	High Similarity	NPC209560
0.9254	High Similarity	NPC212767
0.9254	High Similarity	NPC294409
0.9254	High Similarity	NPC7013
0.9248	High Similarity	NPC151113
0.9248	High Similarity	NPC60667
0.9242	High Similarity	NPC294593
0.9242	High Similarity	NPC159623
0.9242	High Similarity	NPC337373
0.9242	High Similarity	NPC312318
0.9242	High Similarity	NPC472365
0.9242	High Similarity	NPC204960
0.9242	High Similarity	NPC242294
0.9242	High Similarity	NPC82225
0.9242	High Similarity	NPC175098
0.9242	High Similarity	NPC56031
0.9242	High Similarity	NPC144051
0.9242	High Similarity	NPC20560
0.9242	High Similarity	NPC28753
0.9242	High Similarity	NPC18877
0.9242	High Similarity	NPC263670
0.9242	High Similarity	NPC192304
0.9242	High Similarity	NPC188646
0.9242	High Similarity	NPC139813
0.9237	High Similarity	NPC308037
0.9237	High Similarity	NPC64359
0.9237	High Similarity	NPC284424

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 NPC274121 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	476
0.1-0.2	995
0.2-0.3	1599
0.3-0.4	2727
0.4-0.5	1827
0.5-0.6	1061
0.6-0.7	289
0.7-0.8	111
0.8-0.85	41
0.85-0.9	17
0.9-0.95	6
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9545	High Similarity	NPD1552	Clinical (unspecified phase)
0.9545	High Similarity	NPD1550	Clinical (unspecified phase)
0.9474	High Similarity	NPD1549	Phase 2
0.9394	High Similarity	NPD1510	Phase 2
0.927	High Similarity	NPD1511	Approved
0.9237	High Similarity	NPD1240	Approved
0.9203	High Similarity	NPD4378	Clinical (unspecified phase)
0.9137	High Similarity	NPD1512	Approved
0.9098	High Similarity	NPD1607	Approved
0.9065	High Similarity	NPD7410	Clinical (unspecified phase)
0.8897	High Similarity	NPD2796	Approved
0.8777	High Similarity	NPD3750	Approved
0.8699	High Similarity	NPD2801	Approved
0.8633	High Similarity	NPD970	Clinical (unspecified phase)
0.863	High Similarity	NPD1934	Approved
0.8623	High Similarity	NPD1551	Phase 2
0.8621	High Similarity	NPD4380	Phase 2
0.8592	High Similarity	NPD6799	Approved
0.8571	High Similarity	NPD2393	Clinical (unspecified phase)
0.8562	High Similarity	NPD7411	Suspended
0.8561	High Similarity	NPD1203	Approved
0.8523	High Similarity	NPD4381	Clinical (unspecified phase)
0.8514	High Similarity	NPD8443	Clinical (unspecified phase)
0.8417	Intermediate Similarity	NPD3748	Approved
0.84	Intermediate Similarity	NPD3749	Approved
0.84	Intermediate Similarity	NPD7075	Discontinued
0.8382	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8378	Intermediate Similarity	NPD6801	Discontinued
0.8372	Intermediate Similarity	NPD1548	Phase 1
0.8333	Intermediate Similarity	NPD3882	Suspended
0.8322	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8322	Intermediate Similarity	NPD7819	Suspended
0.831	Intermediate Similarity	NPD1243	Approved
0.831	Intermediate Similarity	NPD2800	Approved
0.8288	Intermediate Similarity	NPD5403	Approved
0.8276	Intermediate Similarity	NPD5401	Approved
0.8267	Intermediate Similarity	NPD3817	Phase 2
0.8258	Intermediate Similarity	NPD422	Phase 1
0.8243	Intermediate Similarity	NPD6599	Discontinued
0.8195	Intermediate Similarity	NPD9717	Approved
0.8182	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8169	Intermediate Similarity	NPD2344	Approved
0.8138	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.8129	Intermediate Similarity	NPD943	Approved
0.8125	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.812	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.8116	Intermediate Similarity	NPD2313	Discontinued
0.8092	Intermediate Similarity	NPD7768	Phase 2
0.8089	Intermediate Similarity	NPD3818	Discontinued
0.8077	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8077	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8077	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8077	Intermediate Similarity	NPD6166	Phase 2
0.8074	Intermediate Similarity	NPD3225	Approved
0.8041	Intermediate Similarity	NPD920	Approved
0.8038	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8038	Intermediate Similarity	NPD7054	Approved
0.8027	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.8014	Intermediate Similarity	NPD6651	Approved
0.8	Intermediate Similarity	NPD6959	Discontinued
0.7987	Intermediate Similarity	NPD7472	Approved
0.7986	Intermediate Similarity	NPD3268	Approved
0.7985	Intermediate Similarity	NPD1610	Phase 2
0.7945	Intermediate Similarity	NPD2309	Approved
0.7937	Intermediate Similarity	NPD6797	Phase 2
0.7908	Intermediate Similarity	NPD5402	Approved
0.7902	Intermediate Similarity	NPD2799	Discontinued
0.7902	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7888	Intermediate Similarity	NPD7251	Discontinued
0.7883	Intermediate Similarity	NPD2797	Approved
0.7875	Intermediate Similarity	NPD7074	Phase 3
0.7857	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD1296	Phase 2
0.7847	Intermediate Similarity	NPD2935	Discontinued
0.7847	Intermediate Similarity	NPD6100	Approved
0.7847	Intermediate Similarity	NPD6099	Approved
0.7842	Intermediate Similarity	NPD6832	Phase 2
0.784	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.784	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.784	Intermediate Similarity	NPD7808	Phase 3
0.7826	Intermediate Similarity	NPD2798	Approved
0.7778	Intermediate Similarity	NPD4308	Phase 3
0.7778	Intermediate Similarity	NPD7033	Discontinued
0.7754	Intermediate Similarity	NPD3267	Approved
0.7754	Intermediate Similarity	NPD3266	Approved
0.7727	Intermediate Similarity	NPD1465	Phase 2
0.7722	Intermediate Similarity	NPD6232	Discontinued
0.7716	Intermediate Similarity	NPD5953	Discontinued
0.7714	Intermediate Similarity	NPD4908	Phase 1
0.7714	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7707	Intermediate Similarity	NPD5494	Approved
0.7702	Intermediate Similarity	NPD7286	Phase 2
0.7697	Intermediate Similarity	NPD3226	Approved
0.7688	Intermediate Similarity	NPD7473	Discontinued
0.7687	Intermediate Similarity	NPD2654	Approved
0.7687	Intermediate Similarity	NPD9545	Approved
0.7677	Intermediate Similarity	NPD4288	Approved
0.7669	Intermediate Similarity	NPD9493	Approved
0.7667	Intermediate Similarity	NPD2533	Approved
0.7667	Intermediate Similarity	NPD2534	Approved
0.7667	Intermediate Similarity	NPD2532	Approved
0.7664	Intermediate Similarity	NPD1608	Approved
0.7664	Intermediate Similarity	NPD1481	Phase 2
0.7643	Intermediate Similarity	NPD919	Approved
0.7643	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7635	Intermediate Similarity	NPD4628	Phase 3
0.7606	Intermediate Similarity	NPD411	Approved
0.7606	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7591	Intermediate Similarity	NPD1201	Approved
0.7591	Intermediate Similarity	NPD1535	Discovery
0.7576	Intermediate Similarity	NPD1241	Discontinued
0.7569	Intermediate Similarity	NPD447	Suspended
0.7569	Intermediate Similarity	NPD1933	Approved
0.7561	Intermediate Similarity	NPD6559	Discontinued
0.7551	Intermediate Similarity	NPD2346	Discontinued
0.7547	Intermediate Similarity	NPD1247	Approved
0.7534	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7517	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1470	Approved
0.75	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD4307	Phase 2
0.75	Intermediate Similarity	NPD1613	Approved
0.7483	Intermediate Similarity	NPD3764	Approved
0.7483	Intermediate Similarity	NPD7390	Discontinued
0.7465	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7453	Intermediate Similarity	NPD3926	Phase 2
0.7448	Intermediate Similarity	NPD230	Phase 1
0.7448	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7447	Intermediate Similarity	NPD1019	Discontinued
0.7445	Intermediate Similarity	NPD17	Approved
0.741	Intermediate Similarity	NPD3972	Approved
0.7394	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7384	Intermediate Similarity	NPD4363	Phase 3
0.7384	Intermediate Similarity	NPD4360	Phase 2
0.7378	Intermediate Similarity	NPD5844	Phase 1
0.7376	Intermediate Similarity	NPD1164	Approved
0.7353	Intermediate Similarity	NPD4287	Approved
0.7342	Intermediate Similarity	NPD2296	Approved
0.7341	Intermediate Similarity	NPD4361	Phase 2
0.7341	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD1729	Discontinued
0.7329	Intermediate Similarity	NPD5124	Phase 1
0.7329	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7328	Intermediate Similarity	NPD74	Approved
0.7328	Intermediate Similarity	NPD9266	Approved
0.732	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD1471	Phase 3
0.7299	Intermediate Similarity	NPD1894	Discontinued
0.7299	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD4625	Phase 3
0.7261	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7252	Intermediate Similarity	NPD9263	Approved
0.7252	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7252	Intermediate Similarity	NPD9264	Approved
0.7252	Intermediate Similarity	NPD9267	Approved
0.7241	Intermediate Similarity	NPD6798	Discontinued
0.7237	Intermediate Similarity	NPD2354	Approved
0.7234	Intermediate Similarity	NPD4749	Approved
0.7219	Intermediate Similarity	NPD1652	Phase 2
0.7212	Intermediate Similarity	NPD3751	Discontinued
0.7195	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6104	Discontinued
0.7133	Intermediate Similarity	NPD5408	Approved
0.7133	Intermediate Similarity	NPD5406	Approved
0.7133	Intermediate Similarity	NPD5404	Approved
0.7133	Intermediate Similarity	NPD5405	Approved
0.7108	Intermediate Similarity	NPD5940	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD6844	Discontinued
0.7089	Intermediate Similarity	NPD6585	Discontinued
0.7086	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD2353	Approved
0.7078	Intermediate Similarity	NPD7440	Discontinued
0.7075	Intermediate Similarity	NPD6233	Phase 2
0.7073	Intermediate Similarity	NPD3787	Discontinued
0.7073	Intermediate Similarity	NPD5711	Approved
0.7073	Intermediate Similarity	NPD5710	Approved
0.7063	Intermediate Similarity	NPD1876	Approved
0.7045	Intermediate Similarity	NPD968	Approved
0.7044	Intermediate Similarity	NPD5890	Approved
0.7044	Intermediate Similarity	NPD5889	Approved
0.7042	Intermediate Similarity	NPD9269	Phase 2
0.7037	Intermediate Similarity	NPD6971	Discontinued
0.7034	Intermediate Similarity	NPD2861	Phase 2
0.7034	Intermediate Similarity	NPD9494	Approved
0.7032	Intermediate Similarity	NPD7212	Phase 2
0.7032	Intermediate Similarity	NPD7213	Phase 3
0.7027	Intermediate Similarity	NPD3140	Approved
0.7027	Intermediate Similarity	NPD3142	Approved
0.7025	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD7458	Discontinued
0.7012	Intermediate Similarity	NPD7199	Phase 2
0.7007	Intermediate Similarity	NPD9281	Approved
0.7	Intermediate Similarity	NPD940	Approved
0.7	Intermediate Similarity	NPD846	Approved
0.7	Intermediate Similarity	NPD9268	Approved
0.6988	Remote Similarity	NPD2403	Approved
0.6987	Remote Similarity	NPD4662	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