NPASS Compound

Structure

CID77858 OpenBabel06191715412D 23 25 0 0 0 0 0 0 0 0999 V2000 -2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -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 0.0000 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 -3.4641 1.0000 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 -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 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -2.0000 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 -0.8660 -0.5000 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 -2.5981 2.5000 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 3.4641 -2.0000 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 -1.7321 -2.0000 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 5 1 0 0 0 0 2 6 1 0 0 0 0 3 5 2 0 0 0 0 3 7 1 0 0 0 0 4 8 2 0 0 0 0 4 9 1 0 0 0 0 5 15 1 0 0 0 0 6 7 2 0 0 0 0 6 16 1 0 0 0 0 7 17 1 0 0 0 0 8 11 1 0 0 0 0 8 18 1 0 0 0 0 9 10 2 0 0 0 0 9 23 1 0 0 0 0 10 12 1 0 0 0 0 10 13 1 0 0 0 0 11 12 2 0 0 0 0 11 19 1 0 0 0 0 12 20 1 0 0 0 0 13 14 1 0 0 0 0 13 21 2 0 0 0 0 14 15 2 0 0 0 0 14 22 1 0 0 0 0 15 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	318.04
Volume:	291.557
LogP:	1.588
LogD:	0.478
LogS:	-3.536
# Rotatable Bonds:	1
TPSA:	151.59
# H-Bond Aceptor:	8
# H-Bond Donor:	6
# Rings:	3
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.371
Synthetic Accessibility Score:	2.686
Fsp3:	0.0
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	2
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.519
MDCK Permeability:	6.3176589719660114e-06
Pgp-inhibitor:	0.009
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.036
20% Bioavailability (F20%):	0.874
30% Bioavailability (F30%):	0.997

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.003
Plasma Protein Binding (PPB):	95.28192138671875%
Volume Distribution (VD):	0.603
Pgp-substrate:	11.554295539855957%

ADMET: Metabolism

CYP1A2-inhibitor:	0.697
CYP1A2-substrate:	0.095
CYP2C19-inhibitor:	0.022
CYP2C19-substrate:	0.039
CYP2C9-inhibitor:	0.563
CYP2C9-substrate:	0.202
CYP2D6-inhibitor:	0.054
CYP2D6-substrate:	0.162
CYP3A4-inhibitor:	0.097
CYP3A4-substrate:	0.024

ADMET: Excretion

Clearance (CL):	7.705
Half-life (T1/2):	0.936

ADMET: Toxicity

hERG Blockers:	0.117
Human Hepatotoxicity (H-HT):	0.112
Drug-inuced Liver Injury (DILI):	0.986
AMES Toxicity:	0.656
Rat Oral Acute Toxicity:	0.023
Maximum Recommended Daily Dose:	0.11
Skin Sensitization:	0.945
Carcinogencity:	0.05
Eye Corrosion:	0.004
Eye Irritation:	0.934
Respiratory Toxicity:	0.045

Download Data

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

Natural Product: NPC77858

Natural Product ID:	NPC77858
*Common Name:**	Quercetagetin
IUPAC Name:	2-(3,4-dihydroxyphenyl)-3,5,6,7-tetrahydroxychromen-4-one
Synonyms:	Quercetagetin
Standard InCHIKey:	ZVOLCUVKHLEPEV-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C15H10O8/c16-6-2-1-5(3-7(6)17)15-14(22)13(21)10-9(23-15)4-8(18)11(19)12(10)20/h1-4,16-20,22H
SMILES:	Oc1ccc(cc1O)c1oc2cc(O)c(c(c2c(=O)c1O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL413552
PubChem CID:	5281680
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001615] Flavones [CHEMONTID:0001136] Flavonols

*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
NPO25443	Citrus reticulata	Species	Rutaceae	Eukaryota	n.a.	fruit	n.a.	PMID[10606547]
NPO26488	Tagetes patula	Species	Asteraceae	Eukaryota	n.a.	flower	n.a.	PMID[25539472]
NPO25443	Citrus reticulata	Species	Rutaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO25443	Citrus reticulata	Species	Rutaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO25443	Citrus reticulata	Species	Rutaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO25443	Citrus reticulata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2379	Senecio oryzetorum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO10082	Citrus unshiu	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29757	Acacia catechu	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26488	Tagetes patula	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25443	Citrus reticulata	Species	Rutaceae	Eukaryota	Fruits	n.a.		Database[Phenol-Explorer]
NPO25443	Citrus reticulata	Species	Rutaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO25443	Citrus reticulata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2379	Senecio oryzetorum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10082	Citrus unshiu	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26488	Tagetes patula	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21413	Armillaria tabescens	Species	Physalacriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25443	Citrus reticulata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO29757	Acacia catechu	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO26488	Tagetes patula	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO10082	Citrus unshiu	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO2379	Senecio oryzetorum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO25443	Citrus reticulata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO10082	Citrus unshiu	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO26488	Tagetes patula	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25443	Citrus reticulata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2379	Senecio oryzetorum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10082	Citrus unshiu	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21413	Armillaria tabescens	Species	Physalacriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9150	Polypodiodes formosana	Species	Polypodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9781	Hyphear tanakae	n.a.	n.a.	n.a.	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	2
ED50	1
IC50	18
Ki	1
Others	6

Activity Type	# Activity
Individual Protein	20
Organism	2
Others	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT12	Individual Protein	Human immunodeficiency virus type 1 integrase	Human immunodeficiency virus 1	IC50	=	1300.0	nM	PMID[509916]
NPT12	Individual Protein	Human immunodeficiency virus type 1 integrase	Human immunodeficiency virus 1	IC50	=	600.0	nM	PMID[509916]
NPT12	Individual Protein	Human immunodeficiency virus type 1 integrase	Human immunodeficiency virus 1	IC50	=	800.0	nM	PMID[509917]
NPT12	Individual Protein	Human immunodeficiency virus type 1 integrase	Human immunodeficiency virus 1	IC50	=	100.0	nM	PMID[509917]
NPT12	Individual Protein	Human immunodeficiency virus type 1 integrase	Human immunodeficiency virus 1	IC50	=	800.0	nM	PMID[509918]
NPT12	Individual Protein	Human immunodeficiency virus type 1 integrase	Human immunodeficiency virus 1	IC50	=	100.0	nM	PMID[509918]
NPT1265	Individual Protein	Serine/threonine-protein kinase PIM1	Homo sapiens	IC50	=	340.0	nM	PMID[509921]
NPT1265	Individual Protein	Serine/threonine-protein kinase PIM1	Homo sapiens	-Log IC50	=	0.47	uM	PMID[509921]
NPT1265	Individual Protein	Serine/threonine-protein kinase PIM1	Homo sapiens	IC50	=	340.0	nM	PMID[509922]
NPT1265	Individual Protein	Serine/threonine-protein kinase PIM1	Homo sapiens	IC50	=	340.0	nM	PMID[509923]
NPT1580	Individual Protein	Salivary alpha-amylase	Homo sapiens	IC50	=	10200.0	nM	PMID[509926]
NPT1580	Individual Protein	Salivary alpha-amylase	Homo sapiens	Inhibition	=	97.6	%	PMID[509926]
NPT1265	Individual Protein	Serine/threonine-protein kinase PIM1	Homo sapiens	IC50	=	340.0	nM	PMID[509927]
NPT12	Individual Protein	Human immunodeficiency virus type 1 integrase	Human immunodeficiency virus 1	IC50	=	800.0	nM	PMID[509928]
NPT1380	Individual Protein	Avian myoblastosis virus polyprotein II	Avian myeloblastosis virus	Inhibition	=	98.4	%	PMID[509933]
NPT3918	Individual Protein	Synapsin-1	Bos taurus	IC50	=	150.0	nM	PMID[509935]
NPT1265	Individual Protein	Serine/threonine-protein kinase PIM1	Homo sapiens	IC50	=	340.0	nM	PMID[509937]
NPT1265	Individual Protein	Serine/threonine-protein kinase PIM1	Homo sapiens	ED50	=	5.5	uM	PMID[509937]
NPT2266	Individual Protein	Fructose-1,6-bisphosphatase	Homo sapiens	Inhibition	=	37.0	%	PMID[509938]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	EC50	<	100000.0	nM	PMID[509920]
NPT2	Others	Unspecified		Activity	=	0.0	n.a.	PMID[509925]
NPT2	Others	Unspecified		IC50	=	1300.0	nM	PMID[509929]
NPT870	Individual Protein	Lymphocyte differentiation antigen CD38	Homo sapiens	IC50	=	48600.0	nM	PMID[509930]
NPT1	Others	Radical scavenging activity		EC50	=	10.5	ug	PMID[509931]
NPT2	Others	Unspecified		IC50	=	9700.0	nM	PMID[509932]
NPT2	Others	Unspecified		Ki	=	489.0	nM	PMID[509936]
NPT20632	ORGANISM	Chikungunya virus	Chikungunya virus	IC50	=	25300000.0	nM	PMID[509936]
NPT2	Others	Unspecified		Ratio IC50	=	16.3	n.a.	PMID[509936]

☑ 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 NPC77858 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	588
0.1-0.2	2324
0.2-0.3	6102
0.3-0.4	11571
0.4-0.5	4598
0.5-0.6	4286
0.6-0.7	5206
0.7-0.8	4747
0.8-0.85	1653
0.85-0.9	918
0.9-0.95	455
0.95-1	249

Similarity Score	Similarity Level	Natural Product ID
0.993	High Similarity	NPC195351
0.9862	High Similarity	NPC27208
0.9793	High Similarity	NPC225731
0.979	High Similarity	NPC275772
0.979	High Similarity	NPC130230
0.979	High Similarity	NPC239312
0.9728	High Similarity	NPC214138
0.9722	High Similarity	NPC12367
0.9722	High Similarity	NPC118726
0.972	High Similarity	NPC169749
0.972	High Similarity	NPC20791
0.972	High Similarity	NPC179271
0.9662	High Similarity	NPC247017
0.9662	High Similarity	NPC98661
0.9655	High Similarity	NPC17286
0.9655	High Similarity	NPC216318
0.9655	High Similarity	NPC259713
0.9655	High Similarity	NPC296197
0.9653	High Similarity	NPC74881
0.9653	High Similarity	NPC51443
0.9597	High Similarity	NPC163524
0.9597	High Similarity	NPC176665
0.9597	High Similarity	NPC227192
0.9597	High Similarity	NPC287979
0.9597	High Similarity	NPC189179
0.9597	High Similarity	NPC305663
0.9597	High Similarity	NPC75215
0.9597	High Similarity	NPC93376
0.9597	High Similarity	NPC224137
0.9595	High Similarity	NPC44079
0.9595	High Similarity	NPC201451
0.9595	High Similarity	NPC26227
0.9589	High Similarity	NPC45873
0.9589	High Similarity	NPC184136
0.9586	High Similarity	NPC276930
0.958	High Similarity	NPC279121
0.9533	High Similarity	NPC288669
0.9533	High Similarity	NPC115798
0.9533	High Similarity	NPC18607
0.9533	High Similarity	NPC19687
0.9533	High Similarity	NPC18772
0.9533	High Similarity	NPC7846
0.9533	High Similarity	NPC9609
0.9533	High Similarity	NPC143828
0.9533	High Similarity	NPC191459
0.9533	High Similarity	NPC4481
0.9533	High Similarity	NPC25495
0.9533	High Similarity	NPC261004
0.9533	High Similarity	NPC176300
0.9533	High Similarity	NPC253634
0.9533	High Similarity	NPC105242
0.9533	High Similarity	NPC300943
0.9533	High Similarity	NPC152166
0.9533	High Similarity	NPC22472
0.9533	High Similarity	NPC130894
0.9533	High Similarity	NPC204854
0.953	High Similarity	NPC266960
0.953	High Similarity	NPC245546
0.953	High Similarity	NPC43243
0.953	High Similarity	NPC49824
0.953	High Similarity	NPC474520
0.9521	High Similarity	NPC270465
0.9521	High Similarity	NPC87125
0.9514	High Similarity	NPC70136
0.951	High Similarity	NPC175013
0.9467	High Similarity	NPC78302
0.9467	High Similarity	NPC101830
0.9467	High Similarity	NPC472438
0.9467	High Similarity	NPC235215
0.9467	High Similarity	NPC29841
0.9467	High Similarity	NPC110070
0.9467	High Similarity	NPC7973
0.9467	High Similarity	NPC203891
0.9463	High Similarity	NPC92659
0.9463	High Similarity	NPC4455
0.9463	High Similarity	NPC2476
0.9463	High Similarity	NPC146165
0.9463	High Similarity	NPC138360
0.9463	High Similarity	NPC280339
0.9463	High Similarity	NPC183597
0.9463	High Similarity	NPC128863
0.9463	High Similarity	NPC227325
0.9463	High Similarity	NPC163780
0.9463	High Similarity	NPC50715
0.9463	High Similarity	NPC196439
0.9463	High Similarity	NPC167815
0.9463	High Similarity	NPC201136
0.9459	High Similarity	NPC120163
0.9459	High Similarity	NPC83508
0.9459	High Similarity	NPC198826
0.9459	High Similarity	NPC275836
0.9459	High Similarity	NPC301323
0.9459	High Similarity	NPC212678
0.9459	High Similarity	NPC293183
0.9459	High Similarity	NPC162313
0.9459	High Similarity	NPC131624
0.9459	High Similarity	NPC222830
0.9459	High Similarity	NPC156222
0.9459	High Similarity	NPC239128
0.9459	High Similarity	NPC256283
0.9459	High Similarity	NPC71334
0.9459	High Similarity	NPC301123
0.9459	High Similarity	NPC57030
0.9459	High Similarity	NPC241498
0.9459	High Similarity	NPC142540
0.9459	High Similarity	NPC188203
0.9459	High Similarity	NPC187498
0.9459	High Similarity	NPC100887
0.9459	High Similarity	NPC25270
0.9459	High Similarity	NPC275722
0.9456	High Similarity	NPC62042
0.9456	High Similarity	NPC61620
0.9456	High Similarity	NPC188871
0.9456	High Similarity	NPC149127
0.9456	High Similarity	NPC286342
0.9452	High Similarity	NPC194856
0.9404	High Similarity	NPC193842
0.94	High Similarity	NPC100916
0.94	High Similarity	NPC292107
0.94	High Similarity	NPC55619
0.94	High Similarity	NPC268161
0.94	High Similarity	NPC201837
0.94	High Similarity	NPC200388
0.94	High Similarity	NPC178854
0.9396	High Similarity	NPC274327
0.9396	High Similarity	NPC183878
0.9396	High Similarity	NPC231018
0.9396	High Similarity	NPC255350
0.9396	High Similarity	NPC86485
0.9396	High Similarity	NPC176775
0.9396	High Similarity	NPC276409
0.9396	High Similarity	NPC250822
0.9396	High Similarity	NPC47781
0.9396	High Similarity	NPC69394
0.9396	High Similarity	NPC75279
0.9396	High Similarity	NPC145379
0.9396	High Similarity	NPC22519
0.9396	High Similarity	NPC160951
0.9392	High Similarity	NPC133953
0.9392	High Similarity	NPC251110
0.9392	High Similarity	NPC252933
0.9392	High Similarity	NPC54394
0.9392	High Similarity	NPC28274
0.9392	High Similarity	NPC200740
0.9392	High Similarity	NPC125062
0.9392	High Similarity	NPC204515
0.9392	High Similarity	NPC260895
0.9392	High Similarity	NPC50403
0.9384	High Similarity	NPC108406
0.9384	High Similarity	NPC168803
0.9384	High Similarity	NPC207729
0.9333	High Similarity	NPC189960
0.9333	High Similarity	NPC32557
0.9333	High Similarity	NPC256612
0.9333	High Similarity	NPC20830
0.9333	High Similarity	NPC208197
0.9333	High Similarity	NPC213622
0.9329	High Similarity	NPC120537
0.9329	High Similarity	NPC82325
0.9329	High Similarity	NPC157784
0.9329	High Similarity	NPC199100
0.9329	High Similarity	NPC279989
0.9329	High Similarity	NPC123886
0.9329	High Similarity	NPC55205
0.9329	High Similarity	NPC37684
0.9329	High Similarity	NPC63187
0.9329	High Similarity	NPC180234
0.9329	High Similarity	NPC134677
0.9324	High Similarity	NPC306821
0.9324	High Similarity	NPC248102
0.932	High Similarity	NPC218490
0.932	High Similarity	NPC19545
0.932	High Similarity	NPC119059
0.9272	High Similarity	NPC265511
0.9267	High Similarity	NPC292214
0.9267	High Similarity	NPC179126
0.9267	High Similarity	NPC206238
0.9267	High Similarity	NPC271779
0.9267	High Similarity	NPC167091
0.9267	High Similarity	NPC246204
0.9267	High Similarity	NPC236223
0.9267	High Similarity	NPC78326
0.9267	High Similarity	NPC270620
0.9267	High Similarity	NPC88645
0.9267	High Similarity	NPC162351
0.9267	High Similarity	NPC58382
0.9262	High Similarity	NPC59162
0.9262	High Similarity	NPC304295
0.9262	High Similarity	NPC226973
0.9262	High Similarity	NPC205046
0.9262	High Similarity	NPC202157
0.9262	High Similarity	NPC208043
0.9257	High Similarity	NPC137062
0.9257	High Similarity	NPC223579
0.9257	High Similarity	NPC159103
0.9257	High Similarity	NPC52005
0.9257	High Similarity	NPC287101
0.9257	High Similarity	NPC183950
0.9252	High Similarity	NPC30647
0.9252	High Similarity	NPC140840

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 NPC77858 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	507
0.1-0.2	1069
0.2-0.3	2006
0.3-0.4	2680
0.4-0.5	1551
0.5-0.6	920
0.6-0.7	280
0.7-0.8	91
0.8-0.85	27
0.85-0.9	12
0.9-0.95	2
0.95-1	5

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.972	High Similarity	NPD1512	Approved
0.958	High Similarity	NPD1511	Approved
0.9396	High Similarity	NPD2801	Approved
0.8947	High Similarity	NPD1934	Approved
0.8896	High Similarity	NPD3882	Suspended
0.8889	High Similarity	NPD2393	Clinical (unspecified phase)
0.8831	High Similarity	NPD3817	Phase 2
0.8827	High Similarity	NPD4338	Clinical (unspecified phase)
0.8742	High Similarity	NPD6167	Clinical (unspecified phase)
0.8742	High Similarity	NPD6166	Phase 2
0.8742	High Similarity	NPD6168	Clinical (unspecified phase)
0.8733	High Similarity	NPD4378	Clinical (unspecified phase)
0.8634	High Similarity	NPD3818	Discontinued
0.8589	High Similarity	NPD6797	Phase 2
0.8537	High Similarity	NPD7251	Discontinued
0.8514	High Similarity	NPD1550	Clinical (unspecified phase)
0.8514	High Similarity	NPD1552	Clinical (unspecified phase)
0.8503	High Similarity	NPD1510	Phase 2
0.8483	Intermediate Similarity	NPD943	Approved
0.8471	Intermediate Similarity	NPD5402	Approved
0.8466	Intermediate Similarity	NPD7054	Approved
0.8456	Intermediate Similarity	NPD1549	Phase 2
0.8418	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8415	Intermediate Similarity	NPD7472	Approved
0.8373	Intermediate Similarity	NPD7808	Phase 3
0.8333	Intermediate Similarity	NPD4380	Phase 2
0.8303	Intermediate Similarity	NPD7074	Phase 3
0.8291	Intermediate Similarity	NPD1465	Phase 2
0.8255	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.825	Intermediate Similarity	NPD7075	Discontinued
0.825	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8247	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8231	Intermediate Similarity	NPD1240	Approved
0.821	Intermediate Similarity	NPD1247	Approved
0.8182	Intermediate Similarity	NPD6799	Approved
0.8148	Intermediate Similarity	NPD5494	Approved
0.8144	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8121	Intermediate Similarity	NPD1607	Approved
0.8113	Intermediate Similarity	NPD6801	Discontinued
0.8092	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8082	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.8079	Intermediate Similarity	NPD2796	Approved
0.8063	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8049	Intermediate Similarity	NPD6232	Discontinued
0.8025	Intermediate Similarity	NPD5403	Approved
0.8024	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8014	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.8013	Intermediate Similarity	NPD5401	Approved
0.8012	Intermediate Similarity	NPD7473	Discontinued
0.7987	Intermediate Similarity	NPD3750	Approved
0.795	Intermediate Similarity	NPD7819	Suspended
0.7933	Intermediate Similarity	NPD230	Phase 1
0.7901	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7892	Intermediate Similarity	NPD3926	Phase 2
0.7875	Intermediate Similarity	NPD6599	Discontinued
0.7867	Intermediate Similarity	NPD1613	Approved
0.7867	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7866	Intermediate Similarity	NPD919	Approved
0.7843	Intermediate Similarity	NPD1551	Phase 2
0.7826	Intermediate Similarity	NPD7411	Suspended
0.7815	Intermediate Similarity	NPD447	Suspended
0.7806	Intermediate Similarity	NPD2800	Approved
0.7805	Intermediate Similarity	NPD3749	Approved
0.7771	Intermediate Similarity	NPD6959	Discontinued
0.7727	Intermediate Similarity	NPD2935	Discontinued
0.7707	Intermediate Similarity	NPD6190	Approved
0.7706	Intermediate Similarity	NPD5844	Phase 1
0.7662	Intermediate Similarity	NPD3748	Approved
0.7647	Intermediate Similarity	NPD3751	Discontinued
0.764	Intermediate Similarity	NPD1653	Approved
0.7635	Intermediate Similarity	NPD1203	Approved
0.7616	Intermediate Similarity	NPD2313	Discontinued
0.7593	Intermediate Similarity	NPD3226	Approved
0.758	Intermediate Similarity	NPD1243	Approved
0.7578	Intermediate Similarity	NPD920	Approved
0.7572	Intermediate Similarity	NPD6559	Discontinued
0.7564	Intermediate Similarity	NPD2344	Approved
0.7562	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7551	Intermediate Similarity	NPD9269	Phase 2
0.7548	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7529	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD3787	Discontinued
0.75	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7469	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7453	Intermediate Similarity	NPD2533	Approved
0.7453	Intermediate Similarity	NPD2534	Approved
0.7453	Intermediate Similarity	NPD2532	Approved
0.7448	Intermediate Similarity	NPD1548	Phase 1
0.7438	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7425	Intermediate Similarity	NPD7768	Phase 2
0.7417	Intermediate Similarity	NPD9494	Approved
0.7389	Intermediate Similarity	NPD6099	Approved
0.7389	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD6100	Approved
0.7375	Intermediate Similarity	NPD2309	Approved
0.7374	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD422	Phase 1
0.7358	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7342	Intermediate Similarity	NPD2346	Discontinued
0.7325	Intermediate Similarity	NPD2799	Discontinued
0.732	Intermediate Similarity	NPD3027	Phase 3
0.7315	Intermediate Similarity	NPD9717	Approved
0.7314	Intermediate Similarity	NPD5953	Discontinued
0.7308	Intermediate Similarity	NPD6651	Approved
0.7303	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD7390	Discontinued
0.7279	Intermediate Similarity	NPD9268	Approved
0.7251	Intermediate Similarity	NPD7199	Phase 2
0.7248	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD1610	Phase 2
0.7244	Intermediate Similarity	NPD1933	Approved
0.7235	Intermediate Similarity	NPD6234	Discontinued
0.7232	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD3225	Approved
0.7205	Intermediate Similarity	NPD4628	Phase 3
0.7204	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD1608	Approved
0.72	Intermediate Similarity	NPD7286	Phase 2
0.72	Intermediate Similarity	NPD1481	Phase 2
0.7178	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD1470	Approved
0.7167	Intermediate Similarity	NPD8434	Phase 2
0.7161	Intermediate Similarity	NPD411	Approved
0.7161	Intermediate Similarity	NPD3268	Approved
0.7152	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6832	Phase 2
0.7143	Intermediate Similarity	NPD6844	Discontinued
0.7135	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD1535	Discovery
0.7133	Intermediate Similarity	NPD1201	Approved
0.7125	Intermediate Similarity	NPD1471	Phase 3
0.7124	Intermediate Similarity	NPD2798	Approved
0.7115	Intermediate Similarity	NPD6233	Phase 2
0.7112	Intermediate Similarity	NPD6776	Approved
0.7112	Intermediate Similarity	NPD6781	Approved
0.7112	Intermediate Similarity	NPD6778	Approved
0.7112	Intermediate Similarity	NPD6782	Approved
0.7112	Intermediate Similarity	NPD6780	Approved
0.7112	Intermediate Similarity	NPD6777	Approved
0.7112	Intermediate Similarity	NPD6779	Approved
0.7107	Intermediate Similarity	NPD4308	Phase 3
0.7099	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7079	Intermediate Similarity	NPD7685	Pre-registration
0.7059	Intermediate Similarity	NPD2797	Approved
0.7059	Intermediate Similarity	NPD4288	Approved
0.7051	Intermediate Similarity	NPD1296	Phase 2
0.7041	Intermediate Similarity	NPD37	Approved
0.7032	Intermediate Similarity	NPD4908	Phase 1
0.703	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7029	Intermediate Similarity	NPD2403	Approved
0.7018	Intermediate Similarity	NPD4965	Approved
0.7018	Intermediate Similarity	NPD4967	Phase 2
0.7018	Intermediate Similarity	NPD4966	Approved
0.7	Intermediate Similarity	NPD17	Approved
0.7	Intermediate Similarity	NPD7033	Discontinued
0.7	Intermediate Similarity	NPD7435	Discontinued
0.7	Intermediate Similarity	NPD8313	Approved
0.7	Intermediate Similarity	NPD8312	Approved
0.6978	Remote Similarity	NPD8150	Discontinued
0.6968	Remote Similarity	NPD2861	Phase 2
0.6951	Remote Similarity	NPD2354	Approved
0.6949	Remote Similarity	NPD7228	Approved
0.6948	Remote Similarity	NPD3267	Approved
0.6948	Remote Similarity	NPD3266	Approved
0.6943	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD3764	Approved
0.6943	Remote Similarity	NPD6798	Discontinued
0.6935	Remote Similarity	NPD4360	Phase 2
0.6935	Remote Similarity	NPD4363	Phase 3
0.6933	Remote Similarity	NPD2654	Approved
0.6932	Remote Similarity	NPD7784	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD5710	Approved
0.6914	Remote Similarity	NPD5711	Approved
0.6911	Remote Similarity	NPD7696	Phase 3
0.6911	Remote Similarity	NPD7698	Approved
0.6911	Remote Similarity	NPD7697	Approved
0.6909	Remote Similarity	NPD3300	Phase 2
0.6902	Remote Similarity	NPD4287	Approved
0.6879	Remote Similarity	NPD4625	Phase 3
0.6875	Remote Similarity	NPD5242	Approved
0.6875	Remote Similarity	NPD7871	Phase 2
0.6875	Remote Similarity	NPD7870	Phase 2
0.6867	Remote Similarity	NPD9545	Approved
0.686	Remote Similarity	NPD2296	Approved
0.6859	Remote Similarity	NPD3018	Phase 2
0.6856	Remote Similarity	NPD7701	Phase 2
0.6855	Remote Similarity	NPD4307	Phase 2
0.6846	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6846	Remote Similarity	NPD9493	Approved
0.6845	Remote Similarity	NPD6535	Approved
0.6845	Remote Similarity	NPD6534	Approved
0.6829	Remote Similarity	NPD1652	Phase 2
0.6818	Remote Similarity	NPD7229	Phase 3
0.6818	Remote Similarity	NPD4749	Approved
0.6813	Remote Similarity	NPD6355	Discontinued
0.6809	Remote Similarity	NPD4361	Phase 2

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