NPASS Compound

Structure

CID188871 OpenBabel06191715572D 24 26 0 0 0 0 0 0 0 0999 V2000 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 -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 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 -4.3301 0.5000 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 3.4641 -0.0000 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 22 1 0 0 0 0 2 23 1 0 0 0 0 3 4 2 0 0 0 0 3 8 1 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 9 2 0 0 0 0 6 12 1 0 0 0 0 7 9 1 0 0 0 0 7 13 2 0 0 0 0 8 16 1 0 0 0 0 9 22 1 0 0 0 0 10 11 2 0 0 0 0 10 18 1 0 0 0 0 11 19 1 0 0 0 0 12 14 2 0 0 0 0 12 20 1 0 0 0 0 13 14 1 0 0 0 0 13 24 1 0 0 0 0 14 15 1 0 0 0 0 15 17 1 0 0 0 0 15 21 2 0 0 0 0 16 17 2 0 0 0 0 16 24 1 0 0 0 0 17 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	330.07
Volume:	317.359
LogP:	3.028
LogD:	2.701
LogS:	-3.716
# Rotatable Bonds:	3
TPSA:	109.36
# H-Bond Aceptor:	7
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.633
Synthetic Accessibility Score:	2.414
Fsp3:	0.118
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.942
MDCK Permeability:	1.2438104931788985e-05
Pgp-inhibitor:	0.667
Pgp-substrate:	0.004
Human Intestinal Absorption (HIA):	0.022
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.194

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.007
Plasma Protein Binding (PPB):	93.62540435791016%
Volume Distribution (VD):	0.689
Pgp-substrate:	10.267556190490723%

ADMET: Metabolism

CYP1A2-inhibitor:	0.957
CYP1A2-substrate:	0.918
CYP2C19-inhibitor:	0.234
CYP2C19-substrate:	0.06
CYP2C9-inhibitor:	0.663
CYP2C9-substrate:	0.889
CYP2D6-inhibitor:	0.533
CYP2D6-substrate:	0.742
CYP3A4-inhibitor:	0.381
CYP3A4-substrate:	0.135

ADMET: Excretion

Clearance (CL):	7.292
Half-life (T1/2):	0.888

ADMET: Toxicity

hERG Blockers:	0.027
Human Hepatotoxicity (H-HT):	0.064
Drug-inuced Liver Injury (DILI):	0.973
AMES Toxicity:	0.675
Rat Oral Acute Toxicity:	0.113
Maximum Recommended Daily Dose:	0.592
Skin Sensitization:	0.746
Carcinogencity:	0.05
Eye Corrosion:	0.004
Eye Irritation:	0.925
Respiratory Toxicity:	0.175

Download Data

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

Natural Product: NPC188871

Natural Product ID:	NPC188871
*Common Name:**	3,7-O-Dimethylquercetin
IUPAC Name:	2-(3,4-dihydroxyphenyl)-5-hydroxy-3,7-dimethoxychromen-4-one
Synonyms:
Standard InCHIKey:	LUJAXSNNYBCFEE-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C17H14O7/c1-22-9-6-12(20)14-13(7-9)24-16(17(23-2)15(14)21)8-3-4-10(18)11(19)5-8/h3-7,18-20H,1-2H3
SMILES:	COc1cc(O)c2c(c1)oc(c(c2=O)OC)c1ccc(c(c1)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL164861
PubChem CID:	5280417
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0002585] O-methylated flavonoids [CHEMONTID:0002592] 7-O-methylated flavonoids

*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
NPO21559	Blumea balsamifera	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15787457]
NPO12604	Phakellia dendyi	Species	Bubaridae	Eukaryota	n.a.	Byron Strait, Papua New Guinea	2003	PMID[18327911]
NPO29935	Caesalpinia sappan	Species	Fabaceae	Eukaryota	n.a.	heartwood	n.a.	PMID[19420770]
NPO21559	Blumea balsamifera	Species	Asteraceae	Eukaryota	n.a.	leaf	n.a.	PMID[21319848]
NPO29935	Caesalpinia sappan	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21800859]
NPO29935	Caesalpinia sappan	Species	Fabaceae	Eukaryota	n.a.	heartwood	n.a.	PMID[21800859]
NPO29935	Caesalpinia sappan	Species	Fabaceae	Eukaryota	heartwood	n.a.	n.a.	PMID[23127886]
NPO29935	Caesalpinia sappan	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23234407]
NPO17376	Bacillus amyloliquefaciens	Species	Bacillaceae	Bacteria	n.a.	n.a.	n.a.	PMID[23265519]
NPO17376	Bacillus amyloliquefaciens	Species	Bacillaceae	Bacteria	n.a.	n.a.	n.a.	PMID[24698790]
NPO29935	Caesalpinia sappan	Species	Fabaceae	Eukaryota	seeds	Nanning, Guangxi Province, China	2013-APR	PMID[26398312]
NPO17376	Bacillus amyloliquefaciens	Species	Bacillaceae	Bacteria	n.a.	n.a.	n.a.	PMID[27934031]
NPO28927	Gutierrezia microcephala	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[3655803]
NPO21559	Blumea balsamifera	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29935	Caesalpinia sappan	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21559	Blumea balsamifera	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28927	Gutierrezia microcephala	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29935	Caesalpinia sappan	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO21559	Blumea balsamifera	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO28927	Gutierrezia microcephala	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[Title]
NPO1540	Scopolia tangutica	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28927	Gutierrezia microcephala	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17376	Bacillus amyloliquefaciens	Species	Bacillaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO19778	Streptomyces flaveus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO6819	Cardopatium corymbosum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7081	Sidastrum tehuacanum	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21559	Blumea balsamifera	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3220	Aberia caffra	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO3034	Lonchocarpus yucatanensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12604	Phakellia dendyi	Species	Bubaridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16803	Libanothamnus occultus	Species	Asteraceae	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
ED50	1
IC50	21
Others	21

Activity Type	# Activity
Cell Line	12
CELL-LINE	6
Individual Protein	7
NON-MOLECULAR	9
Organism	4
Others	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT189	Cell Line	Vero	Chlorocebus aethiops	CyD50	=	10.0	ug ml-1	PMID[540486]
NPT168	Cell Line	P388	Mus musculus	ED50	=	3.2	ug ml-1	PMID[540487]
NPT1720	Individual Protein	Plasminogen	Homo sapiens	IC50	=	1500.0	nM	PMID[540488]
NPT71	Cell Line	HEK293	Homo sapiens	Inhibition	=	43.41	%	PMID[540489]
NPT1606	Individual Protein	NADPH oxidase 4	Homo sapiens	IC50	=	1020.0	nM	PMID[540489]
NPT1606	Individual Protein	NADPH oxidase 4	Homo sapiens	Inhibition	=	88.0	%	PMID[540489]
NPT1628	Individual Protein	Thrombin	Oryctolagus cuniculus	TT	=	22.5	s	PMID[540490]
NPT1628	Individual Protein	Thrombin	Oryctolagus cuniculus	PT	=	7.3	s	PMID[540490]
NPT1628	Individual Protein	Thrombin	Oryctolagus cuniculus	APTT	=	54.7	s	PMID[540490]
NPT1628	Individual Protein	Thrombin	Oryctolagus cuniculus	Activity	=	7.3	g/L	PMID[540490]
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	5800.0	nM	PMID[540491]
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	3500.0	nM	PMID[540491]
NPT1668	Cell Line	NCI-H157	Homo sapiens	IC50	=	12970.0	nM	PMID[540493]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	5400.0	nM	PMID[540493]
NPT1669	Cell Line	NCI-H1792	Homo sapiens	IC50	=	19670.0	nM	PMID[540493]
NPT455	Cell Line	NCI-H522	Homo sapiens	IC50	>	50000.0	nM	PMID[540493]
NPT379	Cell Line	HOP-62	Homo sapiens	IC50	=	13180.0	nM	PMID[540493]
NPT387	Cell Line	M14	Homo sapiens	IC50	=	21660.0	nM	PMID[540493]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	11120.0	nM	PMID[540493]
NPT1048	Organism	Poliovirus	Human enterovirus C	Max non-toxic dose	=	10.0	ug ml-1	PMID[540486]
NPT1048	Organism	Poliovirus	Human enterovirus C	Reduction factor	=	1000000.0	n.a.	PMID[540486]
NPT1048	Organism	Poliovirus	Human enterovirus C	Minimal dose	=	0.5	ug ml-1	PMID[540486]
NPT1048	Organism	Poliovirus	Human enterovirus C	ED99	=	0.3	ug ml-1	PMID[540486]
NPT27	Others	Unspecified		Therapeutic index 99	=	33.3	n.a.	PMID[540486]
NPT35	Others	n.a.		IC50	=	102950.0	nM	PMID[540491]
NPT27	Others	Unspecified		Activity	=	80.4	%	PMID[540492]
NPT27	Others	Unspecified		Activity	=	54.1	%	PMID[540492]
NPT22995	CELL-LINE	B16-F0	Mus musculus	Activity	=	187.6	%	PMID[540492]
NPT22995	CELL-LINE	B16-F0	Mus musculus	Activity	=	304.3	%	PMID[540492]
NPT27	Others	Unspecified		Activity	=	60.4	%	PMID[540492]
NPT22995	CELL-LINE	B16-F0	Mus musculus	Activity	=	134.0	%	PMID[540492]
NPT22995	CELL-LINE	B16-F0	Mus musculus	Activity	=	265.5	%	PMID[540492]
NPT22995	CELL-LINE	B16-F0	Mus musculus	Activity	=	222.8	%	PMID[540492]
NPT22995	CELL-LINE	B16-F0	Mus musculus	Activity	=	171.2	%	PMID[540492]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	7020.0	nM	PMID[540493]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	460.0	nM	PMID[540493]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	50000.0	nM	PMID[540493]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	15570.0	nM	PMID[540493]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	23960.0	nM	PMID[540493]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	39570.0	nM	PMID[540493]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	21320.0	nM	PMID[540493]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	24100.0	nM	PMID[540493]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	5280.0	nM	PMID[540493]

☑ 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 NPC188871 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	465
0.1-0.2	1989
0.2-0.3	5126
0.3-0.4	11261
0.4-0.5	5956
0.5-0.6	3911
0.6-0.7	5104
0.7-0.8	4720
0.8-0.85	2012
0.85-0.9	1274
0.9-0.95	597
0.95-1	282

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC149127
1.0	High Similarity	NPC286342
0.9931	High Similarity	NPC260895
0.993	High Similarity	NPC87125
0.993	High Similarity	NPC270465
0.9862	High Similarity	NPC82325
0.9862	High Similarity	NPC279989
0.9795	High Similarity	NPC179126
0.9795	High Similarity	NPC78326
0.9795	High Similarity	NPC270620
0.9795	High Similarity	NPC236223
0.9793	High Similarity	NPC252933
0.9793	High Similarity	NPC54394
0.9793	High Similarity	NPC200740
0.9793	High Similarity	NPC125062
0.979	High Similarity	NPC108406
0.9728	High Similarity	NPC80534
0.9728	High Similarity	NPC133392
0.9728	High Similarity	NPC214138
0.9728	High Similarity	NPC56786
0.9726	High Similarity	NPC55205
0.9726	High Similarity	NPC123886
0.972	High Similarity	NPC179271
0.972	High Similarity	NPC20791
0.9662	High Similarity	NPC265511
0.9662	High Similarity	NPC245546
0.9662	High Similarity	NPC43243
0.9662	High Similarity	NPC266960
0.966	High Similarity	NPC162351
0.966	High Similarity	NPC58382
0.9658	High Similarity	NPC50403
0.9658	High Similarity	NPC28274
0.9658	High Similarity	NPC133953
0.9658	High Similarity	NPC236769
0.9655	High Similarity	NPC159103
0.9655	High Similarity	NPC287101
0.9655	High Similarity	NPC223579
0.9655	High Similarity	NPC183950
0.9655	High Similarity	NPC137062
0.9655	High Similarity	NPC52005
0.9653	High Similarity	NPC74881
0.9653	High Similarity	NPC51443
0.9597	High Similarity	NPC101830
0.9597	High Similarity	NPC163524
0.9597	High Similarity	NPC203891
0.9597	High Similarity	NPC176665
0.9597	High Similarity	NPC287979
0.9597	High Similarity	NPC305663
0.9597	High Similarity	NPC110070
0.9595	High Similarity	NPC44079
0.9595	High Similarity	NPC201451
0.9595	High Similarity	NPC26227
0.9592	High Similarity	NPC63187
0.9592	High Similarity	NPC37684
0.9592	High Similarity	NPC157784
0.9589	High Similarity	NPC50728
0.9589	High Similarity	NPC166753
0.9589	High Similarity	NPC184136
0.9586	High Similarity	NPC119059
0.9586	High Similarity	NPC120464
0.9583	High Similarity	NPC169749
0.958	High Similarity	NPC279121
0.9533	High Similarity	NPC115798
0.9533	High Similarity	NPC18607
0.9533	High Similarity	NPC152166
0.9533	High Similarity	NPC261004
0.9533	High Similarity	NPC19687
0.9533	High Similarity	NPC18772
0.9533	High Similarity	NPC7846
0.9533	High Similarity	NPC143828
0.9533	High Similarity	NPC253634
0.9533	High Similarity	NPC191459
0.9533	High Similarity	NPC288669
0.9533	High Similarity	NPC4481
0.9533	High Similarity	NPC25495
0.9533	High Similarity	NPC176300
0.9533	High Similarity	NPC130894
0.9533	High Similarity	NPC105242
0.9533	High Similarity	NPC300943
0.9533	High Similarity	NPC22472
0.9533	High Similarity	NPC9609
0.9533	High Similarity	NPC204854
0.953	High Similarity	NPC55619
0.953	High Similarity	NPC200388
0.953	High Similarity	NPC100916
0.953	High Similarity	NPC247017
0.953	High Similarity	NPC471500
0.953	High Similarity	NPC153512
0.953	High Similarity	NPC49824
0.953	High Similarity	NPC98661
0.953	High Similarity	NPC292107
0.9524	High Similarity	NPC304295
0.9524	High Similarity	NPC59162
0.9524	High Similarity	NPC76376
0.9524	High Similarity	NPC205046
0.9521	High Similarity	NPC48479
0.9521	High Similarity	NPC177298
0.9521	High Similarity	NPC195351
0.9517	High Similarity	NPC12200
0.9514	High Similarity	NPC70136
0.951	High Similarity	NPC175013
0.9467	High Similarity	NPC224137
0.9467	High Similarity	NPC78302
0.9467	High Similarity	NPC93376
0.9467	High Similarity	NPC189179
0.9467	High Similarity	NPC75215
0.9467	High Similarity	NPC174908
0.9467	High Similarity	NPC471479
0.9467	High Similarity	NPC472438
0.9467	High Similarity	NPC235215
0.9467	High Similarity	NPC29841
0.9467	High Similarity	NPC7973
0.9467	High Similarity	NPC471515
0.9467	High Similarity	NPC227192
0.9463	High Similarity	NPC32557
0.9463	High Similarity	NPC189960
0.9459	High Similarity	NPC241498
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	NPC156222
0.9459	High Similarity	NPC57030
0.9459	High Similarity	NPC25270
0.9459	High Similarity	NPC222830
0.9459	High Similarity	NPC239128
0.9459	High Similarity	NPC256283
0.9459	High Similarity	NPC187498
0.9459	High Similarity	NPC71334
0.9459	High Similarity	NPC301123
0.9459	High Similarity	NPC304954
0.9459	High Similarity	NPC188203
0.9459	High Similarity	NPC60972
0.9459	High Similarity	NPC100887
0.9459	High Similarity	NPC39732
0.9459	High Similarity	NPC275722
0.9456	High Similarity	NPC219330
0.9456	High Similarity	NPC77858
0.9456	High Similarity	NPC88804
0.9456	High Similarity	NPC3825
0.9452	High Similarity	NPC19545
0.9452	High Similarity	NPC195202
0.9452	High Similarity	NPC261548
0.9404	High Similarity	NPC193842
0.94	High Similarity	NPC3980
0.94	High Similarity	NPC320825
0.94	High Similarity	NPC474520
0.94	High Similarity	NPC268161
0.94	High Similarity	NPC326037
0.94	High Similarity	NPC178854
0.94	High Similarity	NPC13858
0.9396	High Similarity	NPC141212
0.9396	High Similarity	NPC274327
0.9396	High Similarity	NPC183878
0.9396	High Similarity	NPC231018
0.9396	High Similarity	NPC86485
0.9396	High Similarity	NPC176775
0.9396	High Similarity	NPC47781
0.9396	High Similarity	NPC255350
0.9396	High Similarity	NPC246204
0.9396	High Similarity	NPC69394
0.9396	High Similarity	NPC22519
0.9396	High Similarity	NPC145379
0.9396	High Similarity	NPC160951
0.9392	High Similarity	NPC225731
0.9384	High Similarity	NPC239312
0.9384	High Similarity	NPC33265
0.9384	High Similarity	NPC130230
0.9384	High Similarity	NPC95864
0.9384	High Similarity	NPC140840
0.9384	High Similarity	NPC275772
0.9384	High Similarity	NPC62536
0.9384	High Similarity	NPC86847
0.9371	High Similarity	NPC103342
0.9371	High Similarity	NPC103904
0.9371	High Similarity	NPC59951
0.9371	High Similarity	NPC230285
0.9371	High Similarity	NPC184536
0.9371	High Similarity	NPC146679
0.9342	High Similarity	NPC471744
0.9342	High Similarity	NPC246478
0.9338	High Similarity	NPC273843
0.9338	High Similarity	NPC52530
0.9338	High Similarity	NPC237418
0.9338	High Similarity	NPC67876
0.9333	High Similarity	NPC92659
0.9333	High Similarity	NPC227325
0.9333	High Similarity	NPC167815
0.9333	High Similarity	NPC20830
0.9333	High Similarity	NPC163780
0.9333	High Similarity	NPC256612
0.9333	High Similarity	NPC128863
0.9333	High Similarity	NPC50715
0.9333	High Similarity	NPC196439
0.9333	High Similarity	NPC2476

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 NPC188871 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	443
0.1-0.2	986
0.2-0.3	1860
0.3-0.4	2647
0.4-0.5	1729
0.5-0.6	961
0.6-0.7	359
0.7-0.8	106
0.8-0.85	35
0.85-0.9	12
0.9-0.95	8
0.95-1	4

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
0.9329	High Similarity	NPD1934	Approved
0.9272	High Similarity	NPD3882	Suspended
0.9267	High Similarity	NPD2393	Clinical (unspecified phase)
0.9205	High Similarity	NPD3817	Phase 2
0.9116	High Similarity	NPD4378	Clinical (unspecified phase)
0.8981	High Similarity	NPD6166	Phase 2
0.8981	High Similarity	NPD6168	Clinical (unspecified phase)
0.8981	High Similarity	NPD6167	Clinical (unspecified phase)
0.8938	High Similarity	NPD6797	Phase 2
0.8882	High Similarity	NPD7251	Discontinued
0.8712	High Similarity	NPD7808	Phase 3
0.8712	High Similarity	NPD4338	Clinical (unspecified phase)
0.8696	High Similarity	NPD7054	Approved
0.8667	High Similarity	NPD6799	Approved
0.8642	High Similarity	NPD7472	Approved
0.8639	High Similarity	NPD1550	Clinical (unspecified phase)
0.8639	High Similarity	NPD1552	Clinical (unspecified phase)
0.8634	High Similarity	NPD3818	Discontinued
0.863	High Similarity	NPD1510	Phase 2
0.8599	High Similarity	NPD7075	Discontinued
0.8581	High Similarity	NPD1549	Phase 2
0.8528	High Similarity	NPD7074	Phase 3
0.8526	High Similarity	NPD7096	Clinical (unspecified phase)
0.8483	Intermediate Similarity	NPD1240	Approved
0.8462	Intermediate Similarity	NPD6801	Discontinued
0.8452	Intermediate Similarity	NPD4380	Phase 2
0.8446	Intermediate Similarity	NPD2796	Approved
0.8418	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8367	Intermediate Similarity	NPD1607	Approved
0.8366	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8365	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8356	Intermediate Similarity	NPD943	Approved
0.8354	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8354	Intermediate Similarity	NPD5402	Approved
0.8333	Intermediate Similarity	NPD6599	Discontinued
0.8333	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8258	Intermediate Similarity	NPD5403	Approved
0.8247	Intermediate Similarity	NPD5401	Approved
0.821	Intermediate Similarity	NPD1247	Approved
0.8199	Intermediate Similarity	NPD919	Approved
0.8176	Intermediate Similarity	NPD7819	Suspended
0.816	Intermediate Similarity	NPD6232	Discontinued
0.8148	Intermediate Similarity	NPD5494	Approved
0.8144	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8133	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.8125	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8121	Intermediate Similarity	NPD7473	Discontinued
0.8105	Intermediate Similarity	NPD3750	Approved
0.8082	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.8063	Intermediate Similarity	NPD1465	Phase 2
0.8054	Intermediate Similarity	NPD230	Phase 1
0.805	Intermediate Similarity	NPD7411	Suspended
0.8014	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD3926	Phase 2
0.7988	Intermediate Similarity	NPD6959	Discontinued
0.7987	Intermediate Similarity	NPD1613	Approved
0.7987	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7961	Intermediate Similarity	NPD1551	Phase 2
0.7922	Intermediate Similarity	NPD2800	Approved
0.7852	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7843	Intermediate Similarity	NPD2935	Discontinued
0.7815	Intermediate Similarity	NPD447	Suspended
0.7811	Intermediate Similarity	NPD5844	Phase 1
0.7805	Intermediate Similarity	NPD3749	Approved
0.7778	Intermediate Similarity	NPD3748	Approved
0.7778	Intermediate Similarity	NPD6559	Discontinued
0.7756	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7751	Intermediate Similarity	NPD3751	Discontinued
0.7744	Intermediate Similarity	NPD7768	Phase 2
0.7738	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7707	Intermediate Similarity	NPD6190	Approved
0.7692	Intermediate Similarity	NPD1243	Approved
0.7692	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7688	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7688	Intermediate Similarity	NPD920	Approved
0.7679	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7677	Intermediate Similarity	NPD2344	Approved
0.7673	Intermediate Similarity	NPD2533	Approved
0.7673	Intermediate Similarity	NPD2534	Approved
0.7673	Intermediate Similarity	NPD2532	Approved
0.7667	Intermediate Similarity	NPD3027	Phase 3
0.7635	Intermediate Similarity	NPD1203	Approved
0.7619	Intermediate Similarity	NPD3787	Discontinued
0.7616	Intermediate Similarity	NPD2313	Discontinued
0.7613	Intermediate Similarity	NPD6100	Approved
0.7613	Intermediate Similarity	NPD6099	Approved
0.7593	Intermediate Similarity	NPD3226	Approved
0.7582	Intermediate Similarity	NPD1933	Approved
0.7569	Intermediate Similarity	NPD1548	Phase 1
0.7562	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7548	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7547	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7533	Intermediate Similarity	NPD9494	Approved
0.7532	Intermediate Similarity	NPD6651	Approved
0.7532	Intermediate Similarity	NPD4628	Phase 3
0.7529	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD2309	Approved
0.7483	Intermediate Similarity	NPD422	Phase 1
0.7468	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7456	Intermediate Similarity	NPD7199	Phase 2
0.7452	Intermediate Similarity	NPD2346	Discontinued
0.7436	Intermediate Similarity	NPD2799	Discontinued
0.7432	Intermediate Similarity	NPD9717	Approved
0.7432	Intermediate Similarity	NPD9269	Phase 2
0.7423	Intermediate Similarity	NPD1653	Approved
0.7418	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7414	Intermediate Similarity	NPD5953	Discontinued
0.7399	Intermediate Similarity	NPD7286	Phase 2
0.7391	Intermediate Similarity	NPD7390	Discontinued
0.7389	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD6798	Discontinued
0.7386	Intermediate Similarity	NPD3268	Approved
0.7368	Intermediate Similarity	NPD4908	Phase 1
0.7368	Intermediate Similarity	NPD6832	Phase 2
0.7365	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD1610	Phase 2
0.7351	Intermediate Similarity	NPD2798	Approved
0.7338	Intermediate Similarity	NPD6233	Phase 2
0.7337	Intermediate Similarity	NPD6234	Discontinued
0.7333	Intermediate Similarity	NPD3225	Approved
0.7326	Intermediate Similarity	NPD2403	Approved
0.7325	Intermediate Similarity	NPD4308	Phase 3
0.7325	Intermediate Similarity	NPD7033	Discontinued
0.7315	Intermediate Similarity	NPD1608	Approved
0.7312	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7285	Intermediate Similarity	NPD2797	Approved
0.7278	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD411	Approved
0.7267	Intermediate Similarity	NPD2354	Approved
0.725	Intermediate Similarity	NPD2654	Approved
0.7244	Intermediate Similarity	NPD6355	Discontinued
0.7233	Intermediate Similarity	NPD1471	Phase 3
0.7225	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7213	Intermediate Similarity	NPD4360	Phase 2
0.7213	Intermediate Similarity	NPD4363	Phase 3
0.7179	Intermediate Similarity	NPD4060	Phase 1
0.7175	Intermediate Similarity	NPD7685	Pre-registration
0.7171	Intermediate Similarity	NPD3266	Approved
0.7171	Intermediate Similarity	NPD3267	Approved
0.7167	Intermediate Similarity	NPD8434	Phase 2
0.7162	Intermediate Similarity	NPD9268	Approved
0.716	Intermediate Similarity	NPD4288	Approved
0.7143	Intermediate Similarity	NPD6844	Discontinued
0.7143	Intermediate Similarity	NPD37	Approved
0.7134	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD1201	Approved
0.7118	Intermediate Similarity	NPD4967	Phase 2
0.7118	Intermediate Similarity	NPD4966	Approved
0.7118	Intermediate Similarity	NPD4965	Approved
0.7114	Intermediate Similarity	NPD17	Approved
0.711	Intermediate Similarity	NPD5710	Approved
0.711	Intermediate Similarity	NPD5711	Approved
0.7097	Intermediate Similarity	NPD4625	Phase 3
0.7097	Intermediate Similarity	NPD7095	Approved
0.7095	Intermediate Similarity	NPD9545	Approved
0.7081	Intermediate Similarity	NPD4361	Phase 2
0.7081	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD3018	Phase 2
0.7075	Intermediate Similarity	NPD9493	Approved
0.707	Intermediate Similarity	NPD4307	Phase 2
0.7069	Intermediate Similarity	NPD5242	Approved
0.7059	Intermediate Similarity	NPD1470	Approved
0.7051	Intermediate Similarity	NPD1296	Phase 2
0.7045	Intermediate Similarity	NPD7228	Approved
0.7045	Intermediate Similarity	NPD2163	Approved
0.7039	Intermediate Similarity	NPD4749	Approved
0.7037	Intermediate Similarity	NPD1652	Phase 2
0.7027	Intermediate Similarity	NPD5536	Phase 2
0.7025	Intermediate Similarity	NPD4340	Discontinued
0.7021	Intermediate Similarity	NPD6782	Approved
0.7021	Intermediate Similarity	NPD6781	Approved
0.7021	Intermediate Similarity	NPD6780	Approved
0.7021	Intermediate Similarity	NPD6779	Approved
0.7021	Intermediate Similarity	NPD6778	Approved
0.7021	Intermediate Similarity	NPD6777	Approved
0.7021	Intermediate Similarity	NPD6776	Approved
0.7019	Intermediate Similarity	NPD2353	Approved
0.7019	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD1019	Discontinued
0.7011	Intermediate Similarity	NPD7229	Phase 3
0.7006	Intermediate Similarity	NPD4062	Phase 3
0.7	Intermediate Similarity	NPD7435	Discontinued
0.7	Intermediate Similarity	NPD8312	Approved
0.7	Intermediate Similarity	NPD8313	Approved
0.6988	Remote Similarity	NPD5049	Phase 3
0.6986	Remote Similarity	NPD1241	Discontinued
0.6982	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6982	Remote Similarity	NPD6385	Approved
0.6982	Remote Similarity	NPD6386	Approved
0.6979	Remote Similarity	NPD7584	Approved
0.6978	Remote Similarity	NPD8150	Discontinued

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