NPASS Compound

Structure

CID57211 OpenBabel06191715392D 28 31 0 0 0 0 0 0 0 0999 V2000 -5.2812 3.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.7453 0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.7453 1.1910 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 -5.2812 1.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1472 -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 -4.4152 -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 -5.2812 0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4152 -0.3090 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 -6.1472 1.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.0132 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 -2.6831 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5491 0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.0132 1.1910 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 -1.8171 0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5491 1.1910 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.1472 2.6910 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.8793 -0.3090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.8793 1.6910 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 -3.5491 -1.8090 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 1 22 1 0 0 0 0 2 23 1 0 0 0 0 3 24 1 0 0 0 0 4 25 1 0 0 0 0 5 10 2 0 0 0 0 5 13 1 0 0 0 0 6 10 1 0 0 0 0 6 14 2 0 0 0 0 7 12 2 0 0 0 0 7 15 1 0 0 0 0 8 11 2 0 0 0 0 8 26 1 0 0 0 0 9 27 1 0 0 0 0 9 28 1 0 0 0 0 10 11 1 0 0 0 0 11 17 1 0 0 0 0 12 16 1 0 0 0 0 12 26 1 0 0 0 0 13 18 2 0 0 0 0 13 22 1 0 0 0 0 14 18 1 0 0 0 0 14 23 1 0 0 0 0 15 19 2 0 0 0 0 15 27 1 0 0 0 0 16 17 1 0 0 0 0 16 20 2 0 0 0 0 17 21 2 0 0 0 0 18 24 1 0 0 0 0 19 20 1 0 0 0 0 19 28 1 0 0 0 0 20 25 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	386.1
Volume:	369.48
LogP:	2.74
LogD:	2.818
LogS:	-4.166
# Rotatable Bonds:	5
TPSA:	85.59
# H-Bond Aceptor:	8
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.661
Synthetic Accessibility Score:	2.611
Fsp3:	0.25
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:	-4.618
MDCK Permeability:	4.598611849360168e-05
Pgp-inhibitor:	0.984
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.001
30% Bioavailability (F30%):	0.013

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.061
Plasma Protein Binding (PPB):	77.28238677978516%
Volume Distribution (VD):	0.756
Pgp-substrate:	18.49744415283203%

ADMET: Metabolism

CYP1A2-inhibitor:	0.38
CYP1A2-substrate:	0.968
CYP2C19-inhibitor:	0.923
CYP2C19-substrate:	0.56
CYP2C9-inhibitor:	0.816
CYP2C9-substrate:	0.921
CYP2D6-inhibitor:	0.377
CYP2D6-substrate:	0.916
CYP3A4-inhibitor:	0.899
CYP3A4-substrate:	0.425

ADMET: Excretion

Clearance (CL):	5.377
Half-life (T1/2):	0.335

ADMET: Toxicity

hERG Blockers:	0.212
Human Hepatotoxicity (H-HT):	0.097
Drug-inuced Liver Injury (DILI):	0.304
AMES Toxicity:	0.074
Rat Oral Acute Toxicity:	0.089
Maximum Recommended Daily Dose:	0.142
Skin Sensitization:	0.655
Carcinogencity:	0.335
Eye Corrosion:	0.004
Eye Irritation:	0.145
Respiratory Toxicity:	0.251

Download Data

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

Natural Product: NPC57211

Natural Product ID:	NPC57211
*Common Name:**	Irisflorentin
IUPAC Name:	9-methoxy-7-(3,4,5-trimethoxyphenyl)-[1,3]dioxolo[4,5-g]chromen-8-one
Synonyms:	Irisflorentin
Standard InCHIKey:	RISXUTCDCPHJFQ-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C20H18O8/c1-22-13-5-10(6-14(23-2)18(13)24-3)11-8-26-12-7-15-19(28-9-27-15)20(25-4)16(12)17(11)21/h5-8H,9H2,1-4H3
SMILES:	COc1cc(cc(c1OC)OC)c1coc2cc3c(c(c2c1=O)OC)OCO3
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL487216
PubChem CID:	170569
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002506] Isoflavonoids [CHEMONTID:0002586] O-methylated isoflavonoids [CHEMONTID:0002606] 4'-O-methylated isoflavonoids [CHEMONTID:0002687] 4'-O-methylisoflavones

*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
NPO1859	Lantana camara	Species	Verbenaceae	Eukaryota	aerial parts	n.a.	n.a.	PMID[10869197]
NPO3165	Cochlospermum tinctorium	Species	Bixaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12350157]
NPO30734	Belamcanda chinensis	Species	Iridaceae	Eukaryota	rhizomes	Thai	n.a.	PMID[15787436]
NPO1859	Lantana camara	Species	Verbenaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1812212]
NPO7528	Belamcanda chinensis	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21465599]
NPO7528	Belamcanda chinensis	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25036154]
NPO3165	Cochlospermum tinctorium	Species	Bixaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[2553872]
NPO7528	Belamcanda chinensis	Species	Iridaceae	Eukaryota	Rhizomes	n.a.	n.a.	PMID[31246464]
NPO1859	Lantana camara	Species	Verbenaceae	Eukaryota	leaves	n.a.	n.a.	PMID[9834145]
NPO30734	Belamcanda chinensis	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9917289]
NPO1859	Lantana camara	Species	Verbenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO30734	Belamcanda chinensis	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13012	Iris dichotoma	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2781	Iris kumaonensis	Species	Tarachodidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7528	Belamcanda chinensis	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1859	Lantana camara	Species	Verbenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13012	Iris dichotoma	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1859	Lantana camara	Species	Verbenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO30734	Belamcanda chinensis	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO13012	Iris dichotoma	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO7528	Belamcanda chinensis	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO7528	Belamcanda chinensis	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3733	Senecio triangularis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2781	Iris kumaonensis	Species	Tarachodidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2566	0cardiopsaceae	Species	0cardiopsaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO942	Perophora namei	Species	Perophoridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5561	Thenea muricata	Species	Theneidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3165	Cochlospermum tinctorium	Species	Bixaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6516	Aspidosperma megalocarpon	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1859	Lantana camara	Species	Verbenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13012	Iris dichotoma	Species	Iridaceae	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
Others	2

Activity Type	# Activity
Cell Line	1
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1310	Individual Protein	Xanthine dehydrogenase	Bos taurus	Inhibition	=	0.0	%	PMID[463295]
NPT83	Cell Line	MCF7	Homo sapiens	Activity	=	50.3	uM	PMID[463296]

☑ 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 NPC57211 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	498
0.1-0.2	2019
0.2-0.3	4947
0.3-0.4	11035
0.4-0.5	6835
0.5-0.6	3930
0.6-0.7	5738
0.7-0.8	5115
0.8-0.85	1811
0.85-0.9	672
0.9-0.95	83
0.95-1	14

Similarity Score	Similarity Level	Natural Product ID
0.9932	High Similarity	NPC52623
0.9864	High Similarity	NPC478213
0.9863	High Similarity	NPC279061
0.9797	High Similarity	NPC478238
0.9796	High Similarity	NPC153008
0.9796	High Similarity	NPC148497
0.9536	High Similarity	NPC167595
0.9474	High Similarity	NPC215375
0.9474	High Similarity	NPC62518
0.9408	High Similarity	NPC258644
0.94	High Similarity	NPC68882
0.94	High Similarity	NPC292460
0.9388	High Similarity	NPC195919
0.9388	High Similarity	NPC120924
0.9388	High Similarity	NPC216314
0.9384	High Similarity	NPC182842
0.9351	High Similarity	NPC260640
0.9351	High Similarity	NPC295009
0.9346	High Similarity	NPC257914
0.9346	High Similarity	NPC238405
0.9346	High Similarity	NPC104459
0.9338	High Similarity	NPC244371
0.932	High Similarity	NPC296575
0.932	High Similarity	NPC224687
0.929	High Similarity	NPC273021
0.929	High Similarity	NPC18284
0.9286	High Similarity	NPC225624
0.9286	High Similarity	NPC285973
0.9167	High Similarity	NPC478199
0.9161	High Similarity	NPC131557
0.9156	High Similarity	NPC310206
0.915	High Similarity	NPC284353
0.9145	High Similarity	NPC35544
0.9145	High Similarity	NPC104728
0.9139	High Similarity	NPC239363
0.9128	High Similarity	NPC302408
0.9128	High Similarity	NPC283002
0.9116	High Similarity	NPC185607
0.9114	High Similarity	NPC113093
0.9103	High Similarity	NPC34376
0.9097	High Similarity	NPC113055
0.9091	High Similarity	NPC155063
0.9085	High Similarity	NPC279930
0.9085	High Similarity	NPC250557
0.9085	High Similarity	NPC186507
0.9079	High Similarity	NPC262623
0.9067	High Similarity	NPC85233
0.9067	High Similarity	NPC205522
0.906	High Similarity	NPC165512
0.9057	High Similarity	NPC135345
0.9054	High Similarity	NPC476054
0.9048	High Similarity	NPC58229
0.9045	High Similarity	NPC469575
0.9032	High Similarity	NPC19097
0.9013	High Similarity	NPC234152
0.9013	High Similarity	NPC156953
0.9007	High Similarity	NPC10304
0.9007	High Similarity	NPC63256
0.9	High Similarity	NPC40818
0.9	High Similarity	NPC215932
0.9	High Similarity	NPC110639
0.9	High Similarity	NPC14958
0.9	High Similarity	NPC106461
0.8968	High Similarity	NPC301897
0.8961	High Similarity	NPC280937
0.8961	High Similarity	NPC124714
0.8954	High Similarity	NPC220577
0.8954	High Similarity	NPC474663
0.8954	High Similarity	NPC45291
0.8954	High Similarity	NPC19980
0.8947	High Similarity	NPC181250
0.8947	High Similarity	NPC238366
0.8944	High Similarity	NPC105511
0.8944	High Similarity	NPC224462
0.8938	High Similarity	NPC76482
0.8933	High Similarity	NPC136278
0.8933	High Similarity	NPC471590
0.8924	High Similarity	NPC302741
0.891	High Similarity	NPC474990
0.891	High Similarity	NPC78103
0.8903	High Similarity	NPC130589
0.8903	High Similarity	NPC134287
0.8896	High Similarity	NPC269451
0.8896	High Similarity	NPC209487
0.8896	High Similarity	NPC216769
0.8896	High Similarity	NPC100263
0.8896	High Similarity	NPC131266
0.8896	High Similarity	NPC121522
0.8896	High Similarity	NPC35763
0.8896	High Similarity	NPC181209
0.8896	High Similarity	NPC100971
0.8896	High Similarity	NPC291802
0.8896	High Similarity	NPC245382
0.8889	High Similarity	NPC475155
0.8889	High Similarity	NPC223375
0.8889	High Similarity	NPC307518
0.8889	High Similarity	NPC205076
0.8889	High Similarity	NPC475825
0.8889	High Similarity	NPC48773
0.8889	High Similarity	NPC259058
0.8889	High Similarity	NPC201547
0.8889	High Similarity	NPC29056
0.8882	High Similarity	NPC476058
0.8874	High Similarity	NPC231013
0.8868	High Similarity	NPC470178
0.8867	High Similarity	NPC23955
0.8867	High Similarity	NPC113089
0.8861	High Similarity	NPC94155
0.8861	High Similarity	NPC162668
0.8859	High Similarity	NPC29536
0.8854	High Similarity	NPC325122
0.8844	High Similarity	NPC44573
0.8841	High Similarity	NPC257714
0.8839	High Similarity	NPC472408
0.8839	High Similarity	NPC128961
0.8834	High Similarity	NPC72455
0.8831	High Similarity	NPC198615
0.8831	High Similarity	NPC104353
0.8831	High Similarity	NPC288316
0.8827	High Similarity	NPC44558
0.8827	High Similarity	NPC212748
0.8824	High Similarity	NPC69752
0.8816	High Similarity	NPC474999
0.8816	High Similarity	NPC119660
0.8816	High Similarity	NPC93034
0.8812	High Similarity	NPC187923
0.8808	High Similarity	NPC213482
0.8805	High Similarity	NPC125991
0.8805	High Similarity	NPC81679
0.8805	High Similarity	NPC61141
0.88	High Similarity	NPC70853
0.88	High Similarity	NPC9966
0.8797	High Similarity	NPC110349
0.8797	High Similarity	NPC298093
0.8797	High Similarity	NPC269906
0.8782	High Similarity	NPC34725
0.8782	High Similarity	NPC18954
0.8782	High Similarity	NPC208197
0.8782	High Similarity	NPC276059
0.8782	High Similarity	NPC241774
0.8782	High Similarity	NPC39184
0.8782	High Similarity	NPC122623
0.878	High Similarity	NPC472607
0.8774	High Similarity	NPC166201
0.8774	High Similarity	NPC134677
0.8774	High Similarity	NPC38469
0.8773	High Similarity	NPC235575
0.8767	High Similarity	NPC143649
0.8766	High Similarity	NPC10467
0.8765	High Similarity	NPC472383
0.8765	High Similarity	NPC475942
0.8765	High Similarity	NPC105025
0.8765	High Similarity	NPC469931
0.8765	High Similarity	NPC472381
0.8765	High Similarity	NPC471287
0.8765	High Similarity	NPC201292
0.8765	High Similarity	NPC226294
0.8765	High Similarity	NPC58053
0.8765	High Similarity	NPC211309
0.8765	High Similarity	NPC45638
0.8765	High Similarity	NPC93337
0.8765	High Similarity	NPC41853
0.8765	High Similarity	NPC183036
0.8765	High Similarity	NPC186807
0.875	High Similarity	NPC153620
0.875	High Similarity	NPC88345
0.875	High Similarity	NPC12377
0.875	High Similarity	NPC94777
0.875	High Similarity	NPC65846
0.875	High Similarity	NPC24257
0.8742	High Similarity	NPC182045
0.8742	High Similarity	NPC209411
0.8742	High Similarity	NPC293201
0.8742	High Similarity	NPC239890
0.8733	High Similarity	NPC124467
0.8733	High Similarity	NPC214919
0.8727	High Similarity	NPC156635
0.8726	High Similarity	NPC257277
0.8726	High Similarity	NPC180340
0.8718	High Similarity	NPC250822
0.8718	High Similarity	NPC75279
0.8718	High Similarity	NPC472915
0.8718	High Similarity	NPC471981
0.8718	High Similarity	NPC276409
0.8712	High Similarity	NPC471416
0.8712	High Similarity	NPC22195
0.8712	High Similarity	NPC293004
0.8712	High Similarity	NPC52353
0.8712	High Similarity	NPC183357
0.8712	High Similarity	NPC34287
0.8712	High Similarity	NPC21190
0.8712	High Similarity	NPC474434
0.871	High Similarity	NPC208043
0.871	High Similarity	NPC226973
0.871	High Similarity	NPC308451
0.8704	High Similarity	NPC45618
0.8704	High Similarity	NPC58716
0.8704	High Similarity	NPC146792
0.8704	High Similarity	NPC167479
0.8704	High Similarity	NPC229729

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 NPC57211 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	431
0.1-0.2	1003
0.2-0.3	1963
0.3-0.4	2730
0.4-0.5	1753
0.5-0.6	831
0.6-0.7	293
0.7-0.8	112
0.8-0.85	28
0.85-0.9	6
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.894	High Similarity	NPD6980	Clinical (unspecified phase)
0.8938	High Similarity	NPD3818	Discontinued
0.8797	High Similarity	NPD5494	Approved
0.8599	High Similarity	NPD2801	Approved
0.8544	High Similarity	NPD3817	Phase 2
0.8443	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8424	Intermediate Similarity	NPD7054	Approved
0.8395	Intermediate Similarity	NPD1247	Approved
0.8375	Intermediate Similarity	NPD3882	Suspended
0.8373	Intermediate Similarity	NPD7472	Approved
0.8373	Intermediate Similarity	NPD7074	Phase 3
0.8323	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8302	Intermediate Similarity	NPD1934	Approved
0.8278	Intermediate Similarity	NPD2796	Approved
0.8225	Intermediate Similarity	NPD7808	Phase 3
0.8214	Intermediate Similarity	NPD6797	Phase 2
0.8182	Intermediate Similarity	NPD3926	Phase 2
0.8166	Intermediate Similarity	NPD7251	Discontinued
0.816	Intermediate Similarity	NPD919	Approved
0.8137	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8121	Intermediate Similarity	NPD6232	Discontinued
0.8092	Intermediate Similarity	NPD1510	Phase 2
0.8084	Intermediate Similarity	NPD7473	Discontinued
0.8075	Intermediate Similarity	NPD37	Approved
0.8063	Intermediate Similarity	NPD4380	Phase 2
0.8037	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8025	Intermediate Similarity	NPD1511	Approved
0.8024	Intermediate Similarity	NPD6166	Phase 2
0.8024	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8024	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7975	Intermediate Similarity	NPD5402	Approved
0.7953	Intermediate Similarity	NPD6559	Discontinued
0.7927	Intermediate Similarity	NPD4966	Approved
0.7927	Intermediate Similarity	NPD4967	Phase 2
0.7927	Intermediate Similarity	NPD4965	Approved
0.7925	Intermediate Similarity	NPD1512	Approved
0.7914	Intermediate Similarity	NPD7819	Suspended
0.7911	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7911	Intermediate Similarity	NPD6799	Approved
0.7882	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7875	Intermediate Similarity	NPD920	Approved
0.7862	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7853	Intermediate Similarity	NPD6801	Discontinued
0.7844	Intermediate Similarity	NPD7199	Phase 2
0.7831	Intermediate Similarity	NPD6234	Discontinued
0.7829	Intermediate Similarity	NPD1240	Approved
0.7805	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD5844	Phase 1
0.7778	Intermediate Similarity	NPD1933	Approved
0.7771	Intermediate Similarity	NPD1243	Approved
0.7771	Intermediate Similarity	NPD7075	Discontinued
0.7751	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.775	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.773	Intermediate Similarity	NPD6599	Discontinued
0.7727	Intermediate Similarity	NPD1607	Approved
0.7722	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7707	Intermediate Similarity	NPD1549	Phase 2
0.7692	Intermediate Similarity	NPD2935	Discontinued
0.7683	Intermediate Similarity	NPD7411	Suspended
0.7643	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7643	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.764	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.764	Intermediate Similarity	NPD2532	Approved
0.764	Intermediate Similarity	NPD2533	Approved
0.764	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.764	Intermediate Similarity	NPD2534	Approved
0.7625	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7597	Intermediate Similarity	NPD943	Approved
0.7595	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.759	Intermediate Similarity	NPD1465	Phase 2
0.7586	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7571	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7556	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.755	Intermediate Similarity	NPD2798	Approved
0.7546	Intermediate Similarity	NPD5403	Approved
0.7544	Intermediate Similarity	NPD5242	Approved
0.7531	Intermediate Similarity	NPD5401	Approved
0.7516	Intermediate Similarity	NPD3748	Approved
0.7514	Intermediate Similarity	NPD7228	Approved
0.75	Intermediate Similarity	NPD1653	Approved
0.7443	Intermediate Similarity	NPD7685	Pre-registration
0.744	Intermediate Similarity	NPD5353	Approved
0.744	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7438	Intermediate Similarity	NPD2654	Approved
0.7436	Intermediate Similarity	NPD230	Phase 1
0.7427	Intermediate Similarity	NPD6959	Discontinued
0.738	Intermediate Similarity	NPD5005	Approved
0.738	Intermediate Similarity	NPD5006	Approved
0.7365	Intermediate Similarity	NPD6385	Approved
0.7365	Intermediate Similarity	NPD6386	Approved
0.7353	Intermediate Similarity	NPD3749	Approved
0.7345	Intermediate Similarity	NPD7240	Approved
0.7338	Intermediate Similarity	NPD6832	Phase 2
0.7333	Intermediate Similarity	NPD3705	Approved
0.7329	Intermediate Similarity	NPD2800	Approved
0.7325	Intermediate Similarity	NPD447	Suspended
0.7314	Intermediate Similarity	NPD3751	Discontinued
0.7299	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD3750	Approved
0.7283	Intermediate Similarity	NPD3787	Discontinued
0.7273	Intermediate Similarity	NPD6778	Approved
0.7273	Intermediate Similarity	NPD6779	Approved
0.7273	Intermediate Similarity	NPD6780	Approved
0.7273	Intermediate Similarity	NPD6782	Approved
0.7273	Intermediate Similarity	NPD6781	Approved
0.7273	Intermediate Similarity	NPD6776	Approved
0.7273	Intermediate Similarity	NPD6777	Approved
0.7258	Intermediate Similarity	NPD4420	Approved
0.7246	Intermediate Similarity	NPD7458	Discontinued
0.7244	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.723	Intermediate Similarity	NPD5536	Phase 2
0.7222	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD2403	Approved
0.7193	Intermediate Similarity	NPD7768	Phase 2
0.7188	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD3027	Phase 3
0.717	Intermediate Similarity	NPD6651	Approved
0.7161	Intermediate Similarity	NPD3018	Phase 2
0.7158	Intermediate Similarity	NPD7697	Approved
0.7158	Intermediate Similarity	NPD7696	Phase 3
0.7158	Intermediate Similarity	NPD7435	Discontinued
0.7158	Intermediate Similarity	NPD7698	Approved
0.715	Intermediate Similarity	NPD8151	Discontinued
0.7143	Intermediate Similarity	NPD1551	Phase 2
0.7143	Intermediate Similarity	NPD3226	Approved
0.7134	Intermediate Similarity	NPD2313	Discontinued
0.7134	Intermediate Similarity	NPD6190	Approved
0.712	Intermediate Similarity	NPD7871	Phase 2
0.712	Intermediate Similarity	NPD7870	Phase 2
0.7105	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD2344	Approved
0.7095	Intermediate Similarity	NPD5953	Discontinued
0.709	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD5710	Approved
0.7086	Intermediate Similarity	NPD5711	Approved
0.7081	Intermediate Similarity	NPD2799	Discontinued
0.7081	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD4628	Phase 3
0.7072	Intermediate Similarity	NPD8312	Approved
0.7072	Intermediate Similarity	NPD8313	Approved
0.7059	Intermediate Similarity	NPD2981	Phase 2
0.7059	Intermediate Similarity	NPD3972	Approved
0.7051	Intermediate Similarity	NPD9494	Approved
0.7049	Intermediate Similarity	NPD8434	Phase 2
0.7048	Intermediate Similarity	NPD7390	Discontinued
0.7017	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7016	Intermediate Similarity	NPD6823	Phase 2
0.7013	Intermediate Similarity	NPD2983	Phase 2
0.7013	Intermediate Similarity	NPD2982	Phase 2
0.701	Intermediate Similarity	NPD7701	Phase 2
0.7006	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7005	Intermediate Similarity	NPD6535	Approved
0.7005	Intermediate Similarity	NPD6534	Approved
0.7	Intermediate Similarity	NPD7028	Phase 2
0.6994	Remote Similarity	NPD2346	Discontinued
0.6994	Remote Similarity	NPD5019	Clinical (unspecified phase)
0.6983	Remote Similarity	NPD7286	Phase 2
0.6959	Remote Similarity	NPD7584	Approved
0.6946	Remote Similarity	NPD4357	Discontinued
0.6943	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.694	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD7874	Approved
0.6937	Remote Similarity	NPD1613	Approved
0.6937	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6936	Remote Similarity	NPD5978	Approved
0.6936	Remote Similarity	NPD5977	Approved
0.6928	Remote Similarity	NPD2309	Approved
0.6919	Remote Similarity	NPD6844	Discontinued
0.6908	Remote Similarity	NPD9268	Approved
0.6904	Remote Similarity	NPD7801	Approved
0.6903	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6899	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6895	Remote Similarity	NPD7699	Phase 2
0.6895	Remote Similarity	NPD7700	Phase 2
0.6893	Remote Similarity	NPD7229	Phase 3
0.689	Remote Similarity	NPD7266	Discontinued
0.689	Remote Similarity	NPD1471	Phase 3
0.6871	Remote Similarity	NPD7033	Discontinued
0.6859	Remote Similarity	NPD1876	Approved
0.6846	Remote Similarity	NPD5283	Phase 1
0.6839	Remote Similarity	NPD9269	Phase 2
0.6833	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD4307	Phase 2
0.6829	Remote Similarity	NPD6100	Approved
0.6829	Remote Similarity	NPD6099	Approved
0.6821	Remote Similarity	NPD6279	Approved
0.6821	Remote Similarity	NPD6280	Approved
0.6818	Remote Similarity	NPD7783	Phase 2
0.6818	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6815	Remote Similarity	NPD3266	Approved
0.6815	Remote Similarity	NPD3267	Approved
0.6805	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6798	Remote Similarity	NPD6808	Phase 2
0.6782	Remote Similarity	NPD8455	Phase 2
0.6774	Remote Similarity	NPD8150	Discontinued
0.6772	Remote Similarity	NPD1019	Discontinued
0.6772	Remote Similarity	NPD6213	Phase 3

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