NPASS Compound

Structure

CID270465 OpenBabel06191716072D 23 25 0 0 0 0 0 0 0 0999 V2000 -2.5981 -3.5000 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 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 -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 1.7321 -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 3.4641 1.0000 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 -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 -1.5000 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 -3.4641 0.0000 0.0000 O 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 4.3301 -0.5000 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 -1.7321 -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 22 1 0 0 0 0 2 3 2 0 0 0 0 2 7 1 0 0 0 0 3 9 1 0 0 0 0 4 7 2 0 0 0 0 4 10 1 0 0 0 0 5 8 2 0 0 0 0 5 11 1 0 0 0 0 6 8 1 0 0 0 0 6 12 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 18 1 0 0 0 0 10 19 1 0 0 0 0 11 13 2 0 0 0 0 11 22 1 0 0 0 0 12 13 1 0 0 0 0 12 23 1 0 0 0 0 13 14 1 0 0 0 0 14 15 1 0 0 0 0 14 20 2 0 0 0 0 15 16 2 0 0 0 0 15 21 1 0 0 0 0 16 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	316.06
Volume:	300.063
LogP:	2.496
LogD:	2.165
LogS:	-3.628
# Rotatable Bonds:	2
TPSA:	120.36
# H-Bond Aceptor:	7
# H-Bond Donor:	4
# Rings:	3
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.535
Synthetic Accessibility Score:	2.519
Fsp3:	0.062
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	2
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.04
MDCK Permeability:	9.899952601699624e-06
Pgp-inhibitor:	0.007
Pgp-substrate:	0.033
Human Intestinal Absorption (HIA):	0.021
20% Bioavailability (F20%):	0.035
30% Bioavailability (F30%):	0.975

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.006
Plasma Protein Binding (PPB):	95.03340911865234%
Volume Distribution (VD):	0.674
Pgp-substrate:	9.554102897644043%

ADMET: Metabolism

CYP1A2-inhibitor:	0.949
CYP1A2-substrate:	0.62
CYP2C19-inhibitor:	0.079
CYP2C19-substrate:	0.048
CYP2C9-inhibitor:	0.612
CYP2C9-substrate:	0.799
CYP2D6-inhibitor:	0.506
CYP2D6-substrate:	0.282
CYP3A4-inhibitor:	0.45
CYP3A4-substrate:	0.079

ADMET: Excretion

Clearance (CL):	8.436
Half-life (T1/2):	0.925

ADMET: Toxicity

hERG Blockers:	0.073
Human Hepatotoxicity (H-HT):	0.066
Drug-inuced Liver Injury (DILI):	0.978
AMES Toxicity:	0.63
Rat Oral Acute Toxicity:	0.085
Maximum Recommended Daily Dose:	0.504
Skin Sensitization:	0.854
Carcinogencity:	0.051
Eye Corrosion:	0.006
Eye Irritation:	0.927
Respiratory Toxicity:	0.103

Download Data

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

Natural Product: NPC270465

Natural Product ID:	NPC270465
*Common Name:**	2-(3,4-Dihydroxyphenyl)-3,7-Dihydroxy-5-Methoxychromen-4-One
IUPAC Name:	2-(3,4-dihydroxyphenyl)-3,7-dihydroxy-5-methoxychromen-4-one
Synonyms:	5-O-Methylquercetin
Standard InCHIKey:	RJBAXROZAXAEEM-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C16H12O7/c1-22-11-5-8(17)6-12-13(11)14(20)15(21)16(23-12)7-2-3-9(18)10(19)4-7/h2-6,17-19,21H,1H3
SMILES:	COc1cc(cc2c1c(=O)c(c(c1ccc(c(c1)O)O)o2)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL470848
PubChem CID:	5281604
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
NPO21072	Rhododendron dauricum	Species	Ericaceae	Eukaryota	n.a.	whole plant	n.a.	DOI[10.1007/BF02329610]
NPO21072	Rhododendron dauricum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15270561]
NPO17782	Inula britannica	Species	Asteraceae	Eukaryota	flowers	n.a.	n.a.	PMID[16643020]
NPO23911	Alpinia officinarum	Species	Zingiberaceae	Eukaryota	n.a.	root	n.a.	PMID[18484537]
NPO23911	Alpinia officinarum	Species	Zingiberaceae	Eukaryota	n.a.	rhizome	n.a.	PMID[18484537]
NPO23911	Alpinia officinarum	Species	Zingiberaceae	Eukaryota	rhizomes	n.a.	n.a.	PMID[19615910]
NPO17759	Rhododendron mucronulatum	Species	Ericaceae	Eukaryota	n.a.	stem	n.a.	PMID[21443171]
NPO9164	Catunaregam spinosa	Species	Rubiaceae	Eukaryota	stem bark	n.a.	n.a.	PMID[21861991]
NPO23911	Alpinia officinarum	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[29323912]
NPO23911	Alpinia officinarum	Species	Zingiberaceae	Eukaryota	n.a.	rhizome	n.a.	PMID[731398]
NPO23911	Alpinia officinarum	Species	Zingiberaceae	Eukaryota	n.a.	root	n.a.	PMID[731398]
NPO17782	Inula britannica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21072	Rhododendron dauricum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14274	Rhododendron mucronatum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11174	Hemsleya graciliflora	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23911	Alpinia officinarum	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17782.1	Inula britannica var. chinensis	Varieties	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17759	Rhododendron mucronulatum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO27772	Flos inulae	Species	Lycaenidae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO62	Tetracera asiatica	Species	Dilleniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO62	Tetracera asiatica	Species	Dilleniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23911	Alpinia officinarum	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17782	Inula britannica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27772	Flos inulae	Species	Lycaenidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14274	Rhododendron mucronatum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17782.1	Inula britannica var. chinensis	Varieties	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21072	Rhododendron dauricum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17759	Rhododendron mucronulatum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11174	Hemsleya graciliflora	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14274	Rhododendron mucronatum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO17782	Inula britannica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO31199	Jnula britannica	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO23911	Alpinia officinarum	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO21072	Rhododendron dauricum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO17759	Rhododendron mucronulatum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO21072	Rhododendron dauricum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO17782	Inula britannica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO23911	Alpinia officinarum	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO9164	Catunaregam spinosa	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17782	Inula britannica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO921	Helichrysum subulifolium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21072	Rhododendron dauricum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2762	Senna lindheimeriana	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6497	Patiria miniata	Species	Asterinidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23911	Alpinia officinarum	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14274	Rhododendron mucronatum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5544	Endiandra xanthocarpa	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17759	Rhododendron mucronulatum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4620	Marasmius prasiosmus	Species	Marasmiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO62	Tetracera asiatica	Species	Dilleniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16866	Rhododendron luteum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9	Camarops microspora	Species	Boliniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11174	Hemsleya graciliflora	Species	Cucurbitaceae	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	3
Others	8

Activity Type	# Activity
Cell Line	1
Individual Protein	7
Others	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT71	Cell Line	HEK293	Homo sapiens	Inhibition	=	3.17	%	PMID[547093]
NPT1606	Individual Protein	NADPH oxidase 4	Homo sapiens	IC50	=	740.0	nM	PMID[547093]
NPT1606	Individual Protein	NADPH oxidase 4	Homo sapiens	Inhibition	=	100.0	%	PMID[547093]
NPT1606	Individual Protein	NADPH oxidase 4	Homo sapiens	Inhibition	=	120.69	%	PMID[547093]
NPT1628	Individual Protein	Thrombin	Oryctolagus cuniculus	TT	=	19.4	s	PMID[547094]
NPT1628	Individual Protein	Thrombin	Oryctolagus cuniculus	PT	=	7.6	s	PMID[547094]
NPT1628	Individual Protein	Thrombin	Oryctolagus cuniculus	APTT	=	49.2	s	PMID[547094]
NPT1628	Individual Protein	Thrombin	Oryctolagus cuniculus	Activity	=	5.0	g/L	PMID[547094]
NPT2	Others	Unspecified		IC50	>	100000.0	nM	PMID[547092]
NPT2	Others	Unspecified		IC50	=	4000.0	nM	PMID[547092]
NPT35	Others	n.a.		Activity	<	70.0	%	PMID[547095]

☑ 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 NPC270465 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	515
0.1-0.2	2105
0.2-0.3	5258
0.3-0.4	11459
0.4-0.5	5508
0.5-0.6	3986
0.6-0.7	5117
0.7-0.8	4702
0.8-0.85	2012
0.85-0.9	1229
0.9-0.95	512
0.95-1	294

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC87125
0.993	High Similarity	NPC188871
0.993	High Similarity	NPC149127
0.993	High Similarity	NPC286342
0.9861	High Similarity	NPC200740
0.9861	High Similarity	NPC260895
0.9861	High Similarity	NPC54394
0.9861	High Similarity	NPC125062
0.9861	High Similarity	NPC252933
0.9859	High Similarity	NPC108406
0.9793	High Similarity	NPC82325
0.9793	High Similarity	NPC279989
0.9793	High Similarity	NPC55205
0.9789	High Similarity	NPC179271
0.9789	High Similarity	NPC20791
0.9726	High Similarity	NPC236223
0.9726	High Similarity	NPC179126
0.9726	High Similarity	NPC78326
0.9726	High Similarity	NPC270620
0.9724	High Similarity	NPC133953
0.9724	High Similarity	NPC50403
0.9724	High Similarity	NPC28274
0.9722	High Similarity	NPC223579
0.9722	High Similarity	NPC183950
0.9722	High Similarity	NPC159103
0.9722	High Similarity	NPC287101
0.9722	High Similarity	NPC52005
0.9722	High Similarity	NPC137062
0.972	High Similarity	NPC74881
0.972	High Similarity	NPC51443
0.966	High Similarity	NPC133392
0.966	High Similarity	NPC56786
0.966	High Similarity	NPC80534
0.966	High Similarity	NPC44079
0.966	High Similarity	NPC201451
0.966	High Similarity	NPC214138
0.966	High Similarity	NPC26227
0.9658	High Similarity	NPC63187
0.9658	High Similarity	NPC37684
0.9658	High Similarity	NPC157784
0.9658	High Similarity	NPC123886
0.9655	High Similarity	NPC50728
0.9655	High Similarity	NPC184136
0.9655	High Similarity	NPC166753
0.9653	High Similarity	NPC120464
0.9653	High Similarity	NPC119059
0.965	High Similarity	NPC169749
0.9648	High Similarity	NPC279121
0.9595	High Similarity	NPC43243
0.9595	High Similarity	NPC98661
0.9595	High Similarity	NPC265511
0.9595	High Similarity	NPC245546
0.9595	High Similarity	NPC49824
0.9595	High Similarity	NPC266960
0.9595	High Similarity	NPC247017
0.9592	High Similarity	NPC58382
0.9592	High Similarity	NPC162351
0.9589	High Similarity	NPC304295
0.9589	High Similarity	NPC205046
0.9589	High Similarity	NPC59162
0.9589	High Similarity	NPC236769
0.9586	High Similarity	NPC48479
0.9586	High Similarity	NPC195351
0.9586	High Similarity	NPC177298
0.9583	High Similarity	NPC12200
0.958	High Similarity	NPC70136
0.9577	High Similarity	NPC175013
0.953	High Similarity	NPC110070
0.953	High Similarity	NPC174908
0.953	High Similarity	NPC163524
0.953	High Similarity	NPC305663
0.953	High Similarity	NPC224137
0.953	High Similarity	NPC101830
0.953	High Similarity	NPC93376
0.953	High Similarity	NPC176665
0.953	High Similarity	NPC75215
0.953	High Similarity	NPC287979
0.953	High Similarity	NPC203891
0.953	High Similarity	NPC189179
0.953	High Similarity	NPC227192
0.9524	High Similarity	NPC71334
0.9524	High Similarity	NPC301123
0.9524	High Similarity	NPC120163
0.9524	High Similarity	NPC39732
0.9524	High Similarity	NPC188203
0.9524	High Similarity	NPC275836
0.9524	High Similarity	NPC275722
0.9524	High Similarity	NPC241498
0.9524	High Similarity	NPC60972
0.9524	High Similarity	NPC100887
0.9524	High Similarity	NPC222830
0.9524	High Similarity	NPC131624
0.9524	High Similarity	NPC239128
0.9524	High Similarity	NPC198826
0.9524	High Similarity	NPC293183
0.9524	High Similarity	NPC187498
0.9524	High Similarity	NPC83508
0.9524	High Similarity	NPC212678
0.9524	High Similarity	NPC57030
0.9524	High Similarity	NPC301323
0.9524	High Similarity	NPC256283
0.9524	High Similarity	NPC162313
0.9524	High Similarity	NPC25270
0.9524	High Similarity	NPC156222
0.9521	High Similarity	NPC88804
0.9521	High Similarity	NPC3825
0.9521	High Similarity	NPC77858
0.9521	High Similarity	NPC219330
0.9517	High Similarity	NPC261548
0.9517	High Similarity	NPC195202
0.9467	High Similarity	NPC7846
0.9467	High Similarity	NPC300943
0.9467	High Similarity	NPC18772
0.9467	High Similarity	NPC288669
0.9467	High Similarity	NPC4481
0.9467	High Similarity	NPC176300
0.9467	High Similarity	NPC253634
0.9467	High Similarity	NPC191459
0.9467	High Similarity	NPC25495
0.9467	High Similarity	NPC9609
0.9467	High Similarity	NPC261004
0.9467	High Similarity	NPC19687
0.9467	High Similarity	NPC143828
0.9467	High Similarity	NPC152166
0.9467	High Similarity	NPC204854
0.9467	High Similarity	NPC115798
0.9467	High Similarity	NPC18607
0.9467	High Similarity	NPC22472
0.9467	High Similarity	NPC105242
0.9467	High Similarity	NPC130894
0.9463	High Similarity	NPC200388
0.9463	High Similarity	NPC13858
0.9463	High Similarity	NPC292107
0.9463	High Similarity	NPC471500
0.9463	High Similarity	NPC474520
0.9463	High Similarity	NPC326037
0.9463	High Similarity	NPC55619
0.9463	High Similarity	NPC153512
0.9463	High Similarity	NPC3980
0.9463	High Similarity	NPC100916
0.9463	High Similarity	NPC320825
0.9459	High Similarity	NPC145379
0.9459	High Similarity	NPC22519
0.9459	High Similarity	NPC69394
0.9459	High Similarity	NPC255350
0.9459	High Similarity	NPC183878
0.9459	High Similarity	NPC86485
0.9459	High Similarity	NPC231018
0.9459	High Similarity	NPC47781
0.9459	High Similarity	NPC176775
0.9459	High Similarity	NPC274327
0.9459	High Similarity	NPC141212
0.9459	High Similarity	NPC160951
0.9456	High Similarity	NPC225731
0.9456	High Similarity	NPC76376
0.9448	High Similarity	NPC33265
0.9448	High Similarity	NPC130230
0.9448	High Similarity	NPC62536
0.9448	High Similarity	NPC275772
0.9448	High Similarity	NPC239312
0.9448	High Similarity	NPC95864
0.94	High Similarity	NPC78302
0.94	High Similarity	NPC472438
0.94	High Similarity	NPC7973
0.94	High Similarity	NPC52530
0.94	High Similarity	NPC29841
0.94	High Similarity	NPC471515
0.94	High Similarity	NPC273843
0.94	High Similarity	NPC235215
0.94	High Similarity	NPC237418
0.94	High Similarity	NPC67876
0.94	High Similarity	NPC471479
0.9396	High Similarity	NPC213622
0.9396	High Similarity	NPC32557
0.9396	High Similarity	NPC256612
0.9396	High Similarity	NPC167815
0.9396	High Similarity	NPC20830
0.9396	High Similarity	NPC227325
0.9396	High Similarity	NPC183597
0.9396	High Similarity	NPC163780
0.9396	High Similarity	NPC2476
0.9396	High Similarity	NPC196439
0.9396	High Similarity	NPC128863
0.9396	High Similarity	NPC4455
0.9396	High Similarity	NPC50715
0.9396	High Similarity	NPC138360
0.9396	High Similarity	NPC280339
0.9396	High Similarity	NPC201136
0.9396	High Similarity	NPC146165
0.9396	High Similarity	NPC92659
0.9396	High Similarity	NPC189960
0.9392	High Similarity	NPC471982
0.9392	High Similarity	NPC27208
0.9392	High Similarity	NPC219582
0.9392	High Similarity	NPC61506
0.9392	High Similarity	NPC304954
0.9392	High Similarity	NPC240476
0.9392	High Similarity	NPC36835
0.9392	High Similarity	NPC9743
0.9392	High Similarity	NPC142540

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 NPC270465 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	474
0.1-0.2	1009
0.2-0.3	1890
0.3-0.4	2655
0.4-0.5	1672
0.5-0.6	954
0.6-0.7	339
0.7-0.8	99
0.8-0.85	37
0.85-0.9	9
0.9-0.95	7
0.95-1	5

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9789	High Similarity	NPD1512	Approved
0.9648	High Similarity	NPD1511	Approved
0.9459	High Similarity	NPD2801	Approved
0.9392	High Similarity	NPD1934	Approved
0.9329	High Similarity	NPD2393	Clinical (unspecified phase)
0.9205	High Similarity	NPD3882	Suspended
0.9178	High Similarity	NPD4378	Clinical (unspecified phase)
0.9139	High Similarity	NPD3817	Phase 2
0.9038	High Similarity	NPD6167	Clinical (unspecified phase)
0.9038	High Similarity	NPD6168	Clinical (unspecified phase)
0.9038	High Similarity	NPD6166	Phase 2
0.8875	High Similarity	NPD6797	Phase 2
0.882	High Similarity	NPD7251	Discontinued
0.875	High Similarity	NPD7054	Approved
0.8699	High Similarity	NPD1552	Clinical (unspecified phase)
0.8699	High Similarity	NPD1550	Clinical (unspecified phase)
0.8696	High Similarity	NPD7472	Approved
0.869	High Similarity	NPD1510	Phase 2
0.8688	High Similarity	NPD3818	Discontinued
0.865	High Similarity	NPD4338	Clinical (unspecified phase)
0.865	High Similarity	NPD7808	Phase 3
0.8639	High Similarity	NPD1549	Phase 2
0.86	High Similarity	NPD6799	Approved
0.858	High Similarity	NPD7074	Phase 3
0.8542	High Similarity	NPD1240	Approved
0.8535	High Similarity	NPD7075	Discontinued
0.8506	High Similarity	NPD4380	Phase 2
0.8503	High Similarity	NPD2796	Approved
0.8471	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8462	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8425	Intermediate Similarity	NPD1607	Approved
0.8421	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8418	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8414	Intermediate Similarity	NPD943	Approved
0.8397	Intermediate Similarity	NPD6801	Discontinued
0.8389	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8293	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8291	Intermediate Similarity	NPD5402	Approved
0.8269	Intermediate Similarity	NPD6599	Discontinued
0.8228	Intermediate Similarity	NPD7819	Suspended
0.821	Intermediate Similarity	NPD6232	Discontinued
0.8199	Intermediate Similarity	NPD5494	Approved
0.8194	Intermediate Similarity	NPD5403	Approved
0.8193	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8188	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.8182	Intermediate Similarity	NPD5401	Approved
0.8176	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8171	Intermediate Similarity	NPD7473	Discontinued
0.8158	Intermediate Similarity	NPD3750	Approved
0.8148	Intermediate Similarity	NPD1247	Approved
0.8138	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.8137	Intermediate Similarity	NPD919	Approved
0.8113	Intermediate Similarity	NPD1465	Phase 2
0.8108	Intermediate Similarity	NPD230	Phase 1
0.8101	Intermediate Similarity	NPD7411	Suspended
0.8069	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.8049	Intermediate Similarity	NPD3926	Phase 2
0.8041	Intermediate Similarity	NPD1613	Approved
0.8041	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8037	Intermediate Similarity	NPD6959	Discontinued
0.8013	Intermediate Similarity	NPD1551	Phase 2
0.7974	Intermediate Similarity	NPD2800	Approved
0.7905	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7895	Intermediate Similarity	NPD2935	Discontinued
0.7867	Intermediate Similarity	NPD447	Suspended
0.7857	Intermediate Similarity	NPD5844	Phase 1
0.7853	Intermediate Similarity	NPD3749	Approved
0.7829	Intermediate Similarity	NPD3748	Approved
0.7824	Intermediate Similarity	NPD6559	Discontinued
0.7806	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7791	Intermediate Similarity	NPD7768	Phase 2
0.7784	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7742	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7742	Intermediate Similarity	NPD1243	Approved
0.7736	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7736	Intermediate Similarity	NPD920	Approved
0.7727	Intermediate Similarity	NPD2344	Approved
0.7722	Intermediate Similarity	NPD2534	Approved
0.7722	Intermediate Similarity	NPD2532	Approved
0.7722	Intermediate Similarity	NPD2533	Approved
0.7718	Intermediate Similarity	NPD3027	Phase 3
0.7692	Intermediate Similarity	NPD3751	Discontinued
0.7687	Intermediate Similarity	NPD1203	Approved
0.7667	Intermediate Similarity	NPD2313	Discontinued
0.7662	Intermediate Similarity	NPD6100	Approved
0.7662	Intermediate Similarity	NPD6099	Approved
0.7643	Intermediate Similarity	NPD6190	Approved
0.764	Intermediate Similarity	NPD3226	Approved
0.7632	Intermediate Similarity	NPD1933	Approved
0.7622	Intermediate Similarity	NPD1548	Phase 1
0.7619	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.761	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7597	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7595	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7584	Intermediate Similarity	NPD9494	Approved
0.7582	Intermediate Similarity	NPD6651	Approved
0.758	Intermediate Similarity	NPD4628	Phase 3
0.7572	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.756	Intermediate Similarity	NPD3787	Discontinued
0.7551	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7547	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7534	Intermediate Similarity	NPD422	Phase 1
0.7532	Intermediate Similarity	NPD2309	Approved
0.7516	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7199	Phase 2
0.75	Intermediate Similarity	NPD2346	Discontinued
0.7484	Intermediate Similarity	NPD2799	Discontinued
0.7483	Intermediate Similarity	NPD9717	Approved
0.7483	Intermediate Similarity	NPD9269	Phase 2
0.7469	Intermediate Similarity	NPD1653	Approved
0.7457	Intermediate Similarity	NPD5953	Discontinued
0.7442	Intermediate Similarity	NPD7286	Phase 2
0.7438	Intermediate Similarity	NPD7390	Discontinued
0.7434	Intermediate Similarity	NPD3268	Approved
0.7417	Intermediate Similarity	NPD6832	Phase 2
0.7417	Intermediate Similarity	NPD4908	Phase 1
0.7415	Intermediate Similarity	NPD1610	Phase 2
0.7415	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.74	Intermediate Similarity	NPD2798	Approved
0.7383	Intermediate Similarity	NPD3225	Approved
0.7381	Intermediate Similarity	NPD6234	Discontinued
0.7372	Intermediate Similarity	NPD4308	Phase 3
0.7372	Intermediate Similarity	NPD7033	Discontinued
0.7365	Intermediate Similarity	NPD1608	Approved
0.7363	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7345	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7337	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD2797	Approved
0.732	Intermediate Similarity	NPD6798	Discontinued
0.732	Intermediate Similarity	NPD411	Approved
0.732	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7318	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7296	Intermediate Similarity	NPD2654	Approved
0.7273	Intermediate Similarity	NPD6233	Phase 2
0.7267	Intermediate Similarity	NPD2403	Approved
0.7253	Intermediate Similarity	NPD4360	Phase 2
0.7253	Intermediate Similarity	NPD4363	Phase 3
0.7219	Intermediate Similarity	NPD3267	Approved
0.7219	Intermediate Similarity	NPD3266	Approved
0.7216	Intermediate Similarity	NPD7685	Pre-registration
0.7211	Intermediate Similarity	NPD9268	Approved
0.7207	Intermediate Similarity	NPD8434	Phase 2
0.7205	Intermediate Similarity	NPD2354	Approved
0.7202	Intermediate Similarity	NPD4288	Approved
0.7186	Intermediate Similarity	NPD6844	Discontinued
0.7186	Intermediate Similarity	NPD37	Approved
0.7181	Intermediate Similarity	NPD1201	Approved
0.7179	Intermediate Similarity	NPD6355	Discontinued
0.7178	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7178	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD1471	Phase 3
0.7168	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7162	Intermediate Similarity	NPD17	Approved
0.716	Intermediate Similarity	NPD4966	Approved
0.716	Intermediate Similarity	NPD4965	Approved
0.716	Intermediate Similarity	NPD4967	Phase 2
0.7151	Intermediate Similarity	NPD5710	Approved
0.7151	Intermediate Similarity	NPD5711	Approved
0.7143	Intermediate Similarity	NPD4625	Phase 3
0.7143	Intermediate Similarity	NPD9545	Approved
0.7124	Intermediate Similarity	NPD3018	Phase 2
0.7123	Intermediate Similarity	NPD9493	Approved
0.712	Intermediate Similarity	NPD4361	Phase 2
0.712	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD4060	Phase 1
0.7115	Intermediate Similarity	NPD4307	Phase 2
0.711	Intermediate Similarity	NPD5242	Approved
0.7105	Intermediate Similarity	NPD1470	Approved
0.7097	Intermediate Similarity	NPD1296	Phase 2
0.7086	Intermediate Similarity	NPD4749	Approved
0.7086	Intermediate Similarity	NPD7228	Approved
0.7081	Intermediate Similarity	NPD1652	Phase 2
0.7075	Intermediate Similarity	NPD5536	Phase 2
0.7059	Intermediate Similarity	NPD6778	Approved
0.7059	Intermediate Similarity	NPD6779	Approved
0.7059	Intermediate Similarity	NPD6781	Approved
0.7059	Intermediate Similarity	NPD6780	Approved
0.7059	Intermediate Similarity	NPD6782	Approved
0.7059	Intermediate Similarity	NPD6776	Approved
0.7059	Intermediate Similarity	NPD1019	Discontinued
0.7059	Intermediate Similarity	NPD6777	Approved
0.7052	Intermediate Similarity	NPD7229	Phase 3
0.7039	Intermediate Similarity	NPD8312	Approved
0.7039	Intermediate Similarity	NPD8313	Approved
0.7034	Intermediate Similarity	NPD1241	Discontinued
0.7032	Intermediate Similarity	NPD7095	Approved
0.7024	Intermediate Similarity	NPD6386	Approved
0.7024	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD6385	Approved
0.702	Intermediate Similarity	NPD1481	Phase 2
0.702	Intermediate Similarity	NPD3972	Approved
0.7018	Intermediate Similarity	NPD6971	Discontinued
0.7017	Intermediate Similarity	NPD8150	Discontinued
0.7016	Intermediate Similarity	NPD7584	Approved
0.7014	Intermediate Similarity	NPD228	Approved
0.7013	Intermediate Similarity	NPD2861	Phase 2
0.7012	Intermediate Similarity	NPD4357	Discontinued
0.7	Intermediate Similarity	NPD2296	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