NPASS Compound

Structure

CID284353 OpenBabel06191716092D 26 29 0 0 0 0 0 0 0 0999 V2000 8.7453 1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 -1.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 4.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0132 2.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1472 3.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1472 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5878 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0132 1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2812 2.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2812 1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 -0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4152 3.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 2.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4152 4.3090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.8793 1.3090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 -1.1910 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 3.3090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.6180 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 4.4152 1.3090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 21 1 0 0 0 0 2 22 1 0 0 0 0 3 23 1 0 0 0 0 4 5 2 0 0 0 0 4 11 1 0 0 0 0 5 12 1 0 0 0 0 6 10 2 0 0 0 0 6 14 1 0 0 0 0 7 10 1 0 0 0 0 7 15 2 0 0 0 0 8 11 2 0 0 0 0 8 13 1 0 0 0 0 9 24 1 0 0 0 0 9 25 1 0 0 0 0 10 17 1 0 0 0 0 11 21 1 0 0 0 0 12 13 2 0 0 0 0 12 16 1 0 0 0 0 13 26 1 0 0 0 0 14 18 2 0 0 0 0 14 22 1 0 0 0 0 15 18 1 0 0 0 0 15 24 1 0 0 0 0 16 19 1 0 0 0 0 16 20 2 0 0 0 0 17 19 2 0 0 0 0 17 26 1 0 0 0 0 18 25 1 0 0 0 0 19 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	356.09
Volume:	343.394
LogP:	3.521
LogD:	3.244
LogS:	-5.225
# Rotatable Bonds:	4
TPSA:	76.36
# H-Bond Aceptor:	7
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.71
Synthetic Accessibility Score:	2.382
Fsp3:	0.211
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.672
MDCK Permeability:	5.5540444009238854e-05
Pgp-inhibitor:	1.0
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.008

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.077
Plasma Protein Binding (PPB):	82.15962982177734%
Volume Distribution (VD):	0.923
Pgp-substrate:	13.061368942260742%

ADMET: Metabolism

CYP1A2-inhibitor:	0.919
CYP1A2-substrate:	0.946
CYP2C19-inhibitor:	0.956
CYP2C19-substrate:	0.534
CYP2C9-inhibitor:	0.815
CYP2C9-substrate:	0.933
CYP2D6-inhibitor:	0.817
CYP2D6-substrate:	0.932
CYP3A4-inhibitor:	0.959
CYP3A4-substrate:	0.307

ADMET: Excretion

Clearance (CL):	7.089
Half-life (T1/2):	0.313

ADMET: Toxicity

hERG Blockers:	0.038
Human Hepatotoxicity (H-HT):	0.211
Drug-inuced Liver Injury (DILI):	0.952
AMES Toxicity:	0.488
Rat Oral Acute Toxicity:	0.032
Maximum Recommended Daily Dose:	0.389
Skin Sensitization:	0.161
Carcinogencity:	0.841
Eye Corrosion:	0.003
Eye Irritation:	0.106
Respiratory Toxicity:	0.311

Download Data

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

Natural Product: NPC284353

Natural Product ID:	NPC284353
*Common Name:**	Kanugin
IUPAC Name:	3,7-dimethoxy-2-(7-methoxy-1,3-benzodioxol-5-yl)chromen-4-one
Synonyms:
Standard InCHIKey:	HZHNYQLMLQAKSH-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C19H16O7/c1-21-11-4-5-12-13(8-11)26-17(19(23-3)16(12)20)10-6-14(22-2)18-15(7-10)24-9-25-18/h4-8H,9H2,1-3H3
SMILES:	COc1ccc2c(c1)oc(c1cc(c3c(c1)OCO3)OC)c(c2=O)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3581067
PubChem CID:	12305452
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
NPO28245	Strychnos nux-vomica	Species	Loganiaceae	Eukaryota	n.a.	seed	n.a.	DOI[10.1016/j.tet.2012.03.006]
NPO28245	Strychnos nux-vomica	Species	Loganiaceae	Eukaryota	n.a.	seed	n.a.	PMID[10.1016/j.tet.2012.03.006]
NPO30165	Pongamia pinnata	Species	Fabaceae	Eukaryota	stem bark	Indonesia	1999-SEP	PMID[14510596]
NPO30165	Pongamia pinnata	Species	Fabaceae	Eukaryota	n.a.	stem	n.a.	PMID[14510596]
NPO28245	Strychnos nux-vomica	Species	Loganiaceae	Eukaryota	n.a.	seed	n.a.	PMID[16317898]
NPO28245	Strychnos nux-vomica	Species	Loganiaceae	Eukaryota	n.a.	seed	n.a.	PMID[17449162]
NPO28245	Strychnos nux-vomica	Species	Loganiaceae	Eukaryota	n.a.	seed	n.a.	PMID[19235686]
NPO28245	Strychnos nux-vomica	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19666019]
NPO28245	Strychnos nux-vomica	Species	Loganiaceae	Eukaryota	n.a.	seed	n.a.	PMID[22707864]
NPO28245	Strychnos nux-vomica	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23088673]
NPO28245	Strychnos nux-vomica	Species	Loganiaceae	Eukaryota	n.a.	seed	n.a.	PMID[2393954]
NPO30165	Pongamia pinnata	Species	Fabaceae	Eukaryota	dry stem	n.a.	n.a.	PMID[25466192]
NPO28245	Strychnos nux-vomica	Species	Loganiaceae	Eukaryota	n.a.	seed	n.a.	PMID[25594733]
NPO30165	Pongamia pinnata	Species	Fabaceae	Eukaryota	Roots	n.a.	n.a.	PMID[29482940]
NPO28245	Strychnos nux-vomica	Species	Loganiaceae	Eukaryota	n.a.	seed	n.a.	PMID[7912074]
NPO17794	Streptomyces violaceusniger	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[8557611]
NPO28245	Strychnos nux-vomica	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO30165	Pongamia pinnata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28245	Strychnos nux-vomica	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28245	Strychnos nux-vomica	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO28007	Cakile maritima	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6223	Ceiba insignis	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28142	Anthoceros agrestis	Species	Anthocerotaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28157	Vriesea regina	Species	Bromeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28299	Leucaena diversifolia	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28245	Strychnos nux-vomica	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27863	Diospyros nigra	Species	Ebenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17794	Streptomyces violaceusniger	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO28332	Lecidea tumida	Species	Lecideaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27972	Clitocybe phosphorea	Species	Tricholomataceae	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	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT34	Cell Line	BV-2	Mus musculus	IC50	>	100000.0	nM	PMID[456053]

☑ 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 NPC284353 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	503
0.1-0.2	2046
0.2-0.3	5100
0.3-0.4	11057
0.4-0.5	6472
0.5-0.6	3988
0.6-0.7	5893
0.7-0.8	4736
0.8-0.85	1887
0.85-0.9	878
0.9-0.95	123
0.95-1	14

Similarity Score	Similarity Level	Natural Product ID
0.9932	High Similarity	NPC279930
0.9669	High Similarity	NPC257914
0.9669	High Similarity	NPC104459
0.9669	High Similarity	NPC238405
0.9608	High Similarity	NPC302741
0.9605	High Similarity	NPC269906
0.9597	High Similarity	NPC68882
0.9524	High Similarity	NPC117463
0.9524	High Similarity	NPC299923
0.9477	High Similarity	NPC131557
0.9467	High Similarity	NPC292460
0.9456	High Similarity	NPC310259
0.9388	High Similarity	NPC296575
0.9346	High Similarity	NPC310206
0.932	High Similarity	NPC113089
0.929	High Similarity	NPC34376
0.9286	High Similarity	NPC113055
0.9281	High Similarity	NPC155063
0.9276	High Similarity	NPC478213
0.9276	High Similarity	NPC244371
0.9272	High Similarity	NPC474170
0.9272	High Similarity	NPC474388
0.9272	High Similarity	NPC472535
0.9267	High Similarity	NPC69752
0.9257	High Similarity	NPC136278
0.9252	High Similarity	NPC70853
0.9252	High Similarity	NPC9966
0.9241	High Similarity	NPC76482
0.9221	High Similarity	NPC258644
0.9211	High Similarity	NPC148497
0.9211	High Similarity	NPC153008
0.9205	High Similarity	NPC201547
0.9205	High Similarity	NPC259058
0.9205	High Similarity	NPC177839
0.92	High Similarity	NPC261548
0.9184	High Similarity	NPC29536
0.9167	High Similarity	NPC94155
0.915	High Similarity	NPC57211
0.9145	High Similarity	NPC279061
0.9145	High Similarity	NPC236769
0.9139	High Similarity	NPC181250
0.9133	High Similarity	NPC205522
0.9128	High Similarity	NPC471590
0.9128	High Similarity	NPC224687
0.9114	High Similarity	NPC187923
0.9108	High Similarity	NPC18284
0.9108	High Similarity	NPC273021
0.9091	High Similarity	NPC122623
0.9091	High Similarity	NPC276059
0.9091	High Similarity	NPC34725
0.9091	High Similarity	NPC478238
0.9091	High Similarity	NPC241774
0.9085	High Similarity	NPC52623
0.9079	High Similarity	NPC50728
0.9079	High Similarity	NPC166753
0.9067	High Similarity	NPC40818
0.9067	High Similarity	NPC106461
0.9067	High Similarity	NPC215932
0.9067	High Similarity	NPC14958
0.9067	High Similarity	NPC110639
0.906	High Similarity	NPC293201
0.9057	High Similarity	NPC254306
0.9057	High Similarity	NPC67037
0.9057	High Similarity	NPC475214
0.9057	High Similarity	NPC113093
0.9057	High Similarity	NPC255615
0.9032	High Similarity	NPC265511
0.9032	High Similarity	NPC257277
0.9026	High Similarity	NPC236223
0.9026	High Similarity	NPC78326
0.9026	High Similarity	NPC179126
0.9026	High Similarity	NPC270620
0.902	High Similarity	NPC76376
0.9013	High Similarity	NPC159103
0.9012	High Similarity	NPC62640
0.9007	High Similarity	NPC85233
0.9006	High Similarity	NPC72249
0.9006	High Similarity	NPC206123
0.9	High Similarity	NPC149244
0.9	High Similarity	NPC48640
0.8994	High Similarity	NPC34531
0.8987	High Similarity	NPC125991
0.8987	High Similarity	NPC478199
0.8968	High Similarity	NPC189960
0.8968	High Similarity	NPC471746
0.8968	High Similarity	NPC32557
0.8961	High Similarity	NPC35544
0.8961	High Similarity	NPC304954
0.8961	High Similarity	NPC134677
0.8961	High Similarity	NPC82325
0.8961	High Similarity	NPC104728
0.8961	High Similarity	NPC279989
0.8961	High Similarity	NPC55205
0.8954	High Similarity	NPC234152
0.8954	High Similarity	NPC219330
0.8951	High Similarity	NPC245452
0.8947	High Similarity	NPC63256
0.8947	High Similarity	NPC10304
0.8947	High Similarity	NPC195202
0.8944	High Similarity	NPC225434
0.8944	High Similarity	NPC203050
0.8944	High Similarity	NPC476180
0.8944	High Similarity	NPC476771
0.8944	High Similarity	NPC223747
0.8944	High Similarity	NPC219904
0.8944	High Similarity	NPC120099
0.894	High Similarity	NPC283002
0.894	High Similarity	NPC302408
0.8933	High Similarity	NPC23955
0.8926	High Similarity	NPC185607
0.8924	High Similarity	NPC182045
0.8917	High Similarity	NPC62518
0.8917	High Similarity	NPC195832
0.8917	High Similarity	NPC215375
0.8912	High Similarity	NPC44573
0.891	High Similarity	NPC178854
0.8903	High Similarity	NPC162351
0.8903	High Similarity	NPC246204
0.8903	High Similarity	NPC473664
0.8903	High Similarity	NPC186507
0.8903	High Similarity	NPC86485
0.8903	High Similarity	NPC58382
0.8896	High Similarity	NPC200740
0.8896	High Similarity	NPC252933
0.8896	High Similarity	NPC260895
0.8896	High Similarity	NPC125062
0.8896	High Similarity	NPC308451
0.8896	High Similarity	NPC54394
0.8889	High Similarity	NPC475434
0.8882	High Similarity	NPC265530
0.8882	High Similarity	NPC226304
0.8882	High Similarity	NPC325555
0.8882	High Similarity	NPC223424
0.8882	High Similarity	NPC52550
0.8882	High Similarity	NPC84362
0.8882	High Similarity	NPC173637
0.8882	High Similarity	NPC62536
0.8882	High Similarity	NPC317489
0.8882	High Similarity	NPC470511
0.8882	High Similarity	NPC12200
0.8882	High Similarity	NPC33265
0.8882	High Similarity	NPC127546
0.8874	High Similarity	NPC165512
0.8868	High Similarity	NPC414831
0.8861	High Similarity	NPC110349
0.8854	High Similarity	NPC203891
0.8854	High Similarity	NPC167595
0.8854	High Similarity	NPC101830
0.8854	High Similarity	NPC19097
0.8854	High Similarity	NPC110070
0.8844	High Similarity	NPC61546
0.8844	High Similarity	NPC72452
0.8839	High Similarity	NPC301123
0.8839	High Similarity	NPC39732
0.8839	High Similarity	NPC40033
0.8839	High Similarity	NPC123886
0.8839	High Similarity	NPC60972
0.8834	High Similarity	NPC153755
0.8834	High Similarity	NPC476772
0.8834	High Similarity	NPC235575
0.8831	High Similarity	NPC286342
0.8831	High Similarity	NPC189270
0.8831	High Similarity	NPC149127
0.8831	High Similarity	NPC188871
0.8831	High Similarity	NPC5840
0.8827	High Similarity	NPC41853
0.8824	High Similarity	NPC476342
0.882	High Similarity	NPC308404
0.882	High Similarity	NPC253662
0.882	High Similarity	NPC21100
0.882	High Similarity	NPC135599
0.882	High Similarity	NPC197285
0.882	High Similarity	NPC73855
0.882	High Similarity	NPC281131
0.882	High Similarity	NPC277174
0.882	High Similarity	NPC88789
0.882	High Similarity	NPC56077
0.882	High Similarity	NPC274618
0.882	High Similarity	NPC118284
0.882	High Similarity	NPC145038
0.882	High Similarity	NPC113968
0.882	High Similarity	NPC328940
0.882	High Similarity	NPC276222
0.882	High Similarity	NPC179950
0.8816	High Similarity	NPC216314
0.8816	High Similarity	NPC195919
0.8816	High Similarity	NPC231013
0.8816	High Similarity	NPC120924
0.8812	High Similarity	NPC243930
0.8812	High Similarity	NPC309025
0.8812	High Similarity	NPC88023
0.8805	High Similarity	NPC216092
0.8805	High Similarity	NPC295009
0.8805	High Similarity	NPC260640
0.8805	High Similarity	NPC162668
0.88	High Similarity	NPC28326
0.88	High Similarity	NPC214919
0.88	High Similarity	NPC124467
0.8797	High Similarity	NPC288669
0.8797	High Similarity	NPC193842

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 NPC284353 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	436
0.1-0.2	974
0.2-0.3	1862
0.3-0.4	2764
0.4-0.5	1751
0.5-0.6	887
0.6-0.7	330
0.7-0.8	105
0.8-0.85	25
0.85-0.9	15
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9091	High Similarity	NPD3817	Phase 2
0.891	High Similarity	NPD3882	Suspended
0.8882	High Similarity	NPD3818	Discontinued
0.8758	High Similarity	NPD6980	Clinical (unspecified phase)
0.8727	High Similarity	NPD7808	Phase 3
0.872	High Similarity	NPD6797	Phase 2
0.8679	High Similarity	NPD919	Approved
0.8667	High Similarity	NPD7251	Discontinued
0.8662	High Similarity	NPD2801	Approved
0.8625	High Similarity	NPD5494	Approved
0.8614	High Similarity	NPD4338	Clinical (unspecified phase)
0.8598	High Similarity	NPD7054	Approved
0.8571	High Similarity	NPD1247	Approved
0.8571	High Similarity	NPD1512	Approved
0.8562	High Similarity	NPD6799	Approved
0.8545	High Similarity	NPD7472	Approved
0.8481	Intermediate Similarity	NPD1934	Approved
0.8467	Intermediate Similarity	NPD2796	Approved
0.8466	Intermediate Similarity	NPD3926	Phase 2
0.8442	Intermediate Similarity	NPD1511	Approved
0.8434	Intermediate Similarity	NPD7074	Phase 3
0.8387	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8385	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8313	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8313	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8303	Intermediate Similarity	NPD6166	Phase 2
0.8303	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8303	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8263	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.825	Intermediate Similarity	NPD6801	Discontinued
0.8239	Intermediate Similarity	NPD6599	Discontinued
0.82	Intermediate Similarity	NPD1933	Approved
0.816	Intermediate Similarity	NPD7075	Discontinued
0.8148	Intermediate Similarity	NPD5402	Approved
0.8133	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.805	Intermediate Similarity	NPD5403	Approved
0.8038	Intermediate Similarity	NPD5401	Approved
0.8012	Intermediate Similarity	NPD6559	Discontinued
0.7975	Intermediate Similarity	NPD7819	Suspended
0.7975	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7949	Intermediate Similarity	NPD1243	Approved
0.7937	Intermediate Similarity	NPD920	Approved
0.7922	Intermediate Similarity	NPD1510	Phase 2
0.7904	Intermediate Similarity	NPD7199	Phase 2
0.7901	Intermediate Similarity	NPD4380	Phase 2
0.7885	Intermediate Similarity	NPD1549	Phase 2
0.7879	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD6232	Discontinued
0.7824	Intermediate Similarity	NPD7473	Discontinued
0.7821	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7821	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7812	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7812	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7806	Intermediate Similarity	NPD3748	Approved
0.7799	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD1240	Approved
0.7744	Intermediate Similarity	NPD7411	Suspended
0.7733	Intermediate Similarity	NPD5844	Phase 1
0.7677	Intermediate Similarity	NPD1607	Approved
0.7674	Intermediate Similarity	NPD3751	Discontinued
0.7658	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD3787	Discontinued
0.7644	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7613	Intermediate Similarity	NPD447	Suspended
0.759	Intermediate Similarity	NPD37	Approved
0.7562	Intermediate Similarity	NPD3750	Approved
0.7562	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.756	Intermediate Similarity	NPD4965	Approved
0.756	Intermediate Similarity	NPD4966	Approved
0.756	Intermediate Similarity	NPD4967	Phase 2
0.7558	Intermediate Similarity	NPD2403	Approved
0.7545	Intermediate Similarity	NPD1465	Phase 2
0.7532	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD6832	Phase 2
0.7515	Intermediate Similarity	NPD3749	Approved
0.75	Intermediate Similarity	NPD2798	Approved
0.75	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7471	Intermediate Similarity	NPD6234	Discontinued
0.7457	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7455	Intermediate Similarity	NPD1653	Approved
0.7436	Intermediate Similarity	NPD943	Approved
0.743	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7421	Intermediate Similarity	NPD1551	Phase 2
0.7421	Intermediate Similarity	NPD2935	Discontinued
0.7418	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7399	Intermediate Similarity	NPD5242	Approved
0.7391	Intermediate Similarity	NPD2654	Approved
0.7391	Intermediate Similarity	NPD2800	Approved
0.7391	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7384	Intermediate Similarity	NPD6959	Discontinued
0.7378	Intermediate Similarity	NPD2534	Approved
0.7378	Intermediate Similarity	NPD2532	Approved
0.7378	Intermediate Similarity	NPD2533	Approved
0.7375	Intermediate Similarity	NPD1471	Phase 3
0.7356	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD7768	Phase 2
0.7321	Intermediate Similarity	NPD6386	Approved
0.7321	Intermediate Similarity	NPD6385	Approved
0.7308	Intermediate Similarity	NPD2313	Discontinued
0.7303	Intermediate Similarity	NPD7685	Pre-registration
0.7297	Intermediate Similarity	NPD5536	Phase 2
0.7294	Intermediate Similarity	NPD5353	Approved
0.7285	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7285	Intermediate Similarity	NPD3705	Approved
0.7278	Intermediate Similarity	NPD230	Phase 1
0.7267	Intermediate Similarity	NPD2344	Approved
0.725	Intermediate Similarity	NPD2799	Discontinued
0.725	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7249	Intermediate Similarity	NPD5005	Approved
0.7249	Intermediate Similarity	NPD5006	Approved
0.7239	Intermediate Similarity	NPD4628	Phase 3
0.7213	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD3226	Approved
0.7195	Intermediate Similarity	NPD6190	Approved
0.7195	Intermediate Similarity	NPD3887	Approved
0.7179	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7175	Intermediate Similarity	NPD7228	Approved
0.7175	Intermediate Similarity	NPD2163	Approved
0.7169	Intermediate Similarity	NPD3146	Approved
0.7169	Intermediate Similarity	NPD3688	Clinical (unspecified phase)
0.7167	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD2346	Discontinued
0.716	Intermediate Similarity	NPD2353	Approved
0.716	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD5019	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD5457	Discontinued
0.7128	Intermediate Similarity	NPD4420	Approved
0.7115	Intermediate Similarity	NPD3018	Phase 2
0.7115	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD4307	Phase 2
0.7107	Intermediate Similarity	NPD1613	Approved
0.7104	Intermediate Similarity	NPD8434	Phase 2
0.7101	Intermediate Similarity	NPD7458	Discontinued
0.7097	Intermediate Similarity	NPD3266	Approved
0.7097	Intermediate Similarity	NPD3267	Approved
0.7097	Intermediate Similarity	NPD1203	Approved
0.7091	Intermediate Similarity	NPD2309	Approved
0.7089	Intermediate Similarity	NPD6798	Discontinued
0.7074	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD6355	Discontinued
0.7056	Intermediate Similarity	NPD5953	Discontinued
0.7053	Intermediate Similarity	NPD6778	Approved
0.7053	Intermediate Similarity	NPD6781	Approved
0.7053	Intermediate Similarity	NPD6780	Approved
0.7053	Intermediate Similarity	NPD6776	Approved
0.7053	Intermediate Similarity	NPD6782	Approved
0.7053	Intermediate Similarity	NPD6779	Approved
0.7053	Intermediate Similarity	NPD6777	Approved
0.7053	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD1019	Discontinued
0.7044	Intermediate Similarity	NPD6233	Phase 2
0.7039	Intermediate Similarity	NPD7286	Phase 2
0.7039	Intermediate Similarity	NPD17	Approved
0.7037	Intermediate Similarity	NPD7033	Discontinued
0.7033	Intermediate Similarity	NPD8312	Approved
0.7033	Intermediate Similarity	NPD8313	Approved
0.7031	Intermediate Similarity	NPD7435	Discontinued
0.7025	Intermediate Similarity	NPD3027	Phase 3
0.7017	Intermediate Similarity	NPD7240	Approved
0.7013	Intermediate Similarity	NPD3972	Approved
0.7013	Intermediate Similarity	NPD9717	Approved
0.7013	Intermediate Similarity	NPD2981	Phase 2
0.701	Intermediate Similarity	NPD7584	Approved
0.6994	Remote Similarity	NPD6100	Approved
0.6994	Remote Similarity	NPD6099	Approved
0.6988	Remote Similarity	NPD2354	Approved
0.6981	Remote Similarity	NPD1296	Phase 2
0.6981	Remote Similarity	NPD3268	Approved
0.6971	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD2983	Phase 2
0.6968	Remote Similarity	NPD2982	Phase 2
0.6959	Remote Similarity	NPD7028	Phase 2
0.6949	Remote Similarity	NPD7229	Phase 3
0.6943	Remote Similarity	NPD7697	Approved
0.6943	Remote Similarity	NPD7698	Approved
0.6943	Remote Similarity	NPD7696	Phase 3
0.6933	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD4308	Phase 3
0.6928	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD1940	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD6971	Discontinued
0.6914	Remote Similarity	NPD6651	Approved
0.6913	Remote Similarity	NPD1241	Discontinued
0.6907	Remote Similarity	NPD7870	Phase 2
0.6907	Remote Similarity	NPD7871	Phase 2
0.6905	Remote Similarity	NPD4357	Discontinued
0.6903	Remote Similarity	NPD1608	Approved
0.6899	Remote Similarity	NPD9494	Approved
0.6897	Remote Similarity	NPD4288	Approved
0.6889	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD2797	Approved
0.6879	Remote Similarity	NPD1049	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD6844	Discontinued
0.6879	Remote Similarity	NPD6280	Approved
0.6879	Remote Similarity	NPD6279	Approved
0.6875	Remote Similarity	NPD411	Approved
0.6864	Remote Similarity	NPD7004	Clinical (unspecified phase)

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