NPASS Compound

Structure

CID106461 OpenBabel06191715452D 23 25 0 0 0 0 0 0 0 0999 V2000 -1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 3.0000 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 0.0000 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 2.0000 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 1.5000 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 -0.8660 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 -0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 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 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 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 20 1 0 0 0 0 2 21 1 0 0 0 0 3 22 1 0 0 0 0 4 5 2 0 0 0 0 4 6 1 0 0 0 0 5 7 1 0 0 0 0 6 8 2 0 0 0 0 7 11 2 0 0 0 0 8 11 1 0 0 0 0 9 12 1 0 0 0 0 9 13 2 0 0 0 0 10 14 2 0 0 0 0 10 15 1 0 0 0 0 11 13 1 0 0 0 0 12 16 1 0 0 0 0 12 19 2 0 0 0 0 13 23 1 0 0 0 0 14 16 1 0 0 0 0 14 23 1 0 0 0 0 15 17 2 0 0 0 0 15 20 1 0 0 0 0 16 18 2 0 0 0 0 17 18 1 0 0 0 0 17 21 1 0 0 0 0 18 22 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	312.1
Volume:	317.074
LogP:	3.375
LogD:	2.984
LogS:	-4.398
# Rotatable Bonds:	4
TPSA:	57.9
# H-Bond Aceptor:	5
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.738
Synthetic Accessibility Score:	2.102
Fsp3:	0.167
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.61
MDCK Permeability:	2.6234733013552614e-05
Pgp-inhibitor:	0.999
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.013

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.121
Plasma Protein Binding (PPB):	84.86988830566406%
Volume Distribution (VD):	0.769
Pgp-substrate:	11.258313179016113%

ADMET: Metabolism

CYP1A2-inhibitor:	0.835
CYP1A2-substrate:	0.97
CYP2C19-inhibitor:	0.923
CYP2C19-substrate:	0.637
CYP2C9-inhibitor:	0.818
CYP2C9-substrate:	0.908
CYP2D6-inhibitor:	0.055
CYP2D6-substrate:	0.89
CYP3A4-inhibitor:	0.652
CYP3A4-substrate:	0.563

ADMET: Excretion

Clearance (CL):	3.746
Half-life (T1/2):	0.325

ADMET: Toxicity

hERG Blockers:	0.23
Human Hepatotoxicity (H-HT):	0.099
Drug-inuced Liver Injury (DILI):	0.734
AMES Toxicity:	0.577
Rat Oral Acute Toxicity:	0.134
Maximum Recommended Daily Dose:	0.119
Skin Sensitization:	0.574
Carcinogencity:	0.188
Eye Corrosion:	0.004
Eye Irritation:	0.426
Respiratory Toxicity:	0.186

Download Data

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

Natural Product: NPC106461

Natural Product ID:	NPC106461
*Common Name:**	Baicalein Trimethyl Ether
IUPAC Name:	5,6,7-trimethoxy-2-phenylchromen-4-one
Synonyms:	Baicalein Trimethyl Ether
Standard InCHIKey:	HJNJAUYFFFOFBW-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C18H16O5/c1-20-15-10-14-16(18(22-3)17(15)21-2)12(19)9-13(23-14)11-7-5-4-6-8-11/h4-10H,1-3H3
SMILES:	COc1cc2oc(cc(=O)c2c(c1OC)OC)c1ccccc1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL182992
PubChem CID:	442583
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
NPO11059	Callicarpa japonica	Species	Lamiaceae	Eukaryota	n.a.	leaf	n.a.	PMID[12165300]
NPO11059	Callicarpa japonica	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9222055]
NPO11059	Callicarpa japonica	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11729	Eugenia exsucca	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9337	Eriocrania cicatricella	Species	Eriocraniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9985	Cercosporidium henningsii	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO11059	Callicarpa japonica	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8015	Plectranthus cyaneus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10118	Rhizoglyphus robini	Species	Acaridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3329	Paralemnalia thyrsoides	Species	Nephtheidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18877	Asplenium ruprechtii	Species	Aspleniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7832	Chirita micromusa	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO2830	Bassia longifolia	Species	Abylidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13986	Anemone coronaria	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2410	Microglossa angolensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16476	Astroloma humifusum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18745	Mycaranthes floribunda	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9212	Litsea consimilis	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5307	Wedelia hookeriana	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3836	Popowia cauliflora	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4103	Chondromyces pediculatus	Species	Polyangiaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
EC50	1
GI50	2
IC50	6
MIC	5
Others	9

Activity Type	# Activity
Cell Line	11
Individual Protein	3
NON-MOLECULAR	1
Organism	6
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1178	Cell Line	KB 3-1	Homo sapiens	EC50	=	5500.0	nM	PMID[519032]
NPT1178	Cell Line	KB 3-1	Homo sapiens	Amax	=	2.7	pmoles	PMID[519032]
NPT91	Cell Line	KB	Homo sapiens	IC50	=	85900.0	nM	PMID[519032]
NPT1178	Cell Line	KB 3-1	Homo sapiens	IC50	=	57900.0	nM	PMID[519032]
NPT1310	Individual Protein	Xanthine dehydrogenase	Bos taurus	Inhibition	=	22.0	%	PMID[519033]
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	>	100000.0	nM	PMID[519035]
NPT113	Cell Line	RAW264.7	Mus musculus	Inhibition	=	12.1	%	PMID[519035]
NPT113	Cell Line	RAW264.7	Mus musculus	Inhibition	=	42.19	%	PMID[519035]
NPT1380	Individual Protein	Avian myoblastosis virus polyprotein II	Avian myeloblastosis virus	Inhibition	=	29.8	%	PMID[519036]
NPT83	Cell Line	MCF7	Homo sapiens	GI50	=	91400.0	nM	PMID[519037]
NPT65	Cell Line	HepG2	Homo sapiens	GI50	=	53990.0	nM	PMID[519037]
NPT83	Cell Line	MCF7	Homo sapiens	GI	>	50.0	%	PMID[519037]
NPT65	Cell Line	HepG2	Homo sapiens	GI	>	50.0	%	PMID[519037]
NPT2266	Individual Protein	Fructose-1,6-bisphosphatase	Homo sapiens	Inhibition	<	20.0	%	PMID[519038]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	n.a.	50.0	ug.mL-1	PMID[519031]
NPT1271	Organism	Bacillus sp.	Bacillus sp.	MIC	n.a.	25.0	ug.mL-1	PMID[519031]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	n.a.	25.0	ug.mL-1	PMID[519031]
NPT720	Organism	Enterobacter aerogenes	Enterobacter aerogenes	MIC	n.a.	50.0	ug.mL-1	PMID[519031]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	MIC	n.a.	25.0	ug.mL-1	PMID[519031]
NPT35	Others	n.a.		CLogD	=	2.9	n.a.	PMID[519032]
NPT2	Others	Unspecified		IC50	>	50.0	ug.mL-1	PMID[519034]
NPT20	Organism	Candida albicans	Candida albicans	IC50	>	50.0	ug.mL-1	PMID[519034]
NPT85	Organism	Filobasidiella neoformans	Cryptococcus neoformans	IC50	>	50.0	ug.mL-1	PMID[519034]

☑ 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 NPC106461 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	568
0.1-0.2	2173
0.2-0.3	5482
0.3-0.4	12026
0.4-0.5	4848
0.5-0.6	4185
0.6-0.7	5534
0.7-0.8	4647
0.8-0.85	1920
0.85-0.9	873
0.9-0.95	381
0.95-1	60

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC215932
1.0	High Similarity	NPC110639
1.0	High Similarity	NPC14958
1.0	High Similarity	NPC40818
0.9929	High Similarity	NPC85233
0.9929	High Similarity	NPC205522
0.9857	High Similarity	NPC283002
0.9857	High Similarity	NPC302408
0.9856	High Similarity	NPC23955
0.9789	High Similarity	NPC69752
0.9786	High Similarity	NPC136278
0.9786	High Similarity	NPC165512
0.9784	High Similarity	NPC70853
0.9784	High Similarity	NPC9966
0.972	High Similarity	NPC201547
0.972	High Similarity	NPC259058
0.9718	High Similarity	NPC10304
0.9718	High Similarity	NPC63256
0.9714	High Similarity	NPC113089
0.9712	High Similarity	NPC124467
0.9712	High Similarity	NPC214919
0.9712	High Similarity	NPC29536
0.9653	High Similarity	NPC226973
0.9653	High Similarity	NPC208043
0.965	High Similarity	NPC238366
0.965	High Similarity	NPC181250
0.9586	High Similarity	NPC134677
0.9583	High Similarity	NPC306821
0.9577	High Similarity	NPC120924
0.9577	High Similarity	NPC310259
0.9577	High Similarity	NPC195919
0.9577	High Similarity	NPC216314
0.9577	High Similarity	NPC231013
0.9521	High Similarity	NPC472408
0.9521	High Similarity	NPC186507
0.9521	High Similarity	NPC183878
0.9521	High Similarity	NPC145379
0.9521	High Similarity	NPC69394
0.9521	High Similarity	NPC22519
0.9521	High Similarity	NPC160951
0.9521	High Similarity	NPC86485
0.9521	High Similarity	NPC274327
0.9521	High Similarity	NPC47781
0.9521	High Similarity	NPC231018
0.9521	High Similarity	NPC255350
0.9521	High Similarity	NPC176775
0.9517	High Similarity	NPC308451
0.9514	High Similarity	NPC328119
0.951	High Similarity	NPC299923
0.9507	High Similarity	NPC471590
0.95	High Similarity	NPC58229
0.9456	High Similarity	NPC128863
0.9456	High Similarity	NPC163780
0.9456	High Similarity	NPC167815
0.9456	High Similarity	NPC50715
0.9456	High Similarity	NPC241774
0.9456	High Similarity	NPC227325
0.9456	High Similarity	NPC196439
0.9456	High Similarity	NPC256612
0.9456	High Similarity	NPC201136
0.9456	High Similarity	NPC122623
0.9456	High Similarity	NPC32557
0.9456	High Similarity	NPC213622
0.9456	High Similarity	NPC146165
0.9456	High Similarity	NPC34725
0.9456	High Similarity	NPC4455
0.9456	High Similarity	NPC2476
0.9456	High Similarity	NPC92659
0.9456	High Similarity	NPC276059
0.9456	High Similarity	NPC138360
0.9456	High Similarity	NPC280339
0.9456	High Similarity	NPC20830
0.9456	High Similarity	NPC183597
0.9456	High Similarity	NPC189960
0.9452	High Similarity	NPC120163
0.9452	High Similarity	NPC292460
0.9452	High Similarity	NPC83508
0.9452	High Similarity	NPC198826
0.9452	High Similarity	NPC275836
0.9452	High Similarity	NPC301323
0.9452	High Similarity	NPC212678
0.9452	High Similarity	NPC293183
0.9452	High Similarity	NPC162313
0.9452	High Similarity	NPC100887
0.9452	High Similarity	NPC131624
0.9452	High Similarity	NPC25270
0.9452	High Similarity	NPC222830
0.9452	High Similarity	NPC156222
0.9452	High Similarity	NPC239128
0.9452	High Similarity	NPC256283
0.9452	High Similarity	NPC71334
0.9452	High Similarity	NPC301123
0.9452	High Similarity	NPC57030
0.9452	High Similarity	NPC166201
0.9452	High Similarity	NPC241498
0.9452	High Similarity	NPC188203
0.9452	High Similarity	NPC187498
0.9452	High Similarity	NPC275722
0.9444	High Similarity	NPC195202
0.9444	High Similarity	NPC261548
0.9437	High Similarity	NPC182842
0.9437	High Similarity	NPC293201
0.9392	High Similarity	NPC178854
0.9392	High Similarity	NPC49824
0.9392	High Similarity	NPC257277
0.9388	High Similarity	NPC75279
0.9388	High Similarity	NPC280937
0.9388	High Similarity	NPC472915
0.9388	High Similarity	NPC476289
0.9388	High Similarity	NPC128961
0.9388	High Similarity	NPC250822
0.9388	High Similarity	NPC276409
0.9384	High Similarity	NPC117579
0.9375	High Similarity	NPC33265
0.9375	High Similarity	NPC62536
0.9375	High Similarity	NPC12200
0.9329	High Similarity	NPC189179
0.9329	High Similarity	NPC203891
0.9329	High Similarity	NPC224137
0.9329	High Similarity	NPC227192
0.9329	High Similarity	NPC110070
0.9329	High Similarity	NPC470402
0.9329	High Similarity	NPC101830
0.9329	High Similarity	NPC93376
0.9329	High Similarity	NPC19097
0.9329	High Similarity	NPC476981
0.9329	High Similarity	NPC75215
0.9324	High Similarity	NPC37392
0.9324	High Similarity	NPC201451
0.9324	High Similarity	NPC44079
0.9324	High Similarity	NPC26227
0.9324	High Similarity	NPC472909
0.9324	High Similarity	NPC208197
0.932	High Similarity	NPC39732
0.932	High Similarity	NPC60972
0.932	High Similarity	NPC142540
0.9315	High Similarity	NPC166753
0.9315	High Similarity	NPC184136
0.9315	High Similarity	NPC50728
0.931	High Similarity	NPC476342
0.9296	High Similarity	NPC185607
0.9286	High Similarity	NPC44573
0.9267	High Similarity	NPC22472
0.9267	High Similarity	NPC104459
0.9267	High Similarity	NPC238405
0.9267	High Similarity	NPC130894
0.9267	High Similarity	NPC18772
0.9267	High Similarity	NPC7846
0.9267	High Similarity	NPC300943
0.9267	High Similarity	NPC191459
0.9267	High Similarity	NPC288669
0.9267	High Similarity	NPC152166
0.9267	High Similarity	NPC18607
0.9267	High Similarity	NPC105242
0.9267	High Similarity	NPC115798
0.9267	High Similarity	NPC25495
0.9267	High Similarity	NPC9609
0.9267	High Similarity	NPC261004
0.9267	High Similarity	NPC19687
0.9267	High Similarity	NPC143828
0.9267	High Similarity	NPC4481
0.9267	High Similarity	NPC176300
0.9267	High Similarity	NPC253634
0.9267	High Similarity	NPC257914
0.9267	High Similarity	NPC204854
0.9262	High Similarity	NPC266960
0.9262	High Similarity	NPC247017
0.9262	High Similarity	NPC98661
0.9262	High Similarity	NPC180340
0.9262	High Similarity	NPC245546
0.9262	High Similarity	NPC472916
0.9262	High Similarity	NPC292107
0.9262	High Similarity	NPC303255
0.9262	High Similarity	NPC474520
0.9262	High Similarity	NPC43243
0.9257	High Similarity	NPC246204
0.9252	High Similarity	NPC262623
0.9252	High Similarity	NPC474170
0.9252	High Similarity	NPC474388
0.9252	High Similarity	NPC472535
0.9252	High Similarity	NPC474663
0.9252	High Similarity	NPC149614
0.9252	High Similarity	NPC198615
0.9252	High Similarity	NPC236769
0.9247	High Similarity	NPC296197
0.9247	High Similarity	NPC223579
0.9247	High Similarity	NPC287101
0.9247	High Similarity	NPC48479
0.9247	High Similarity	NPC183950
0.9247	High Similarity	NPC177298
0.9247	High Similarity	NPC259713
0.9247	High Similarity	NPC17286
0.9247	High Similarity	NPC137062
0.9247	High Similarity	NPC159103
0.9247	High Similarity	NPC216318
0.9247	High Similarity	NPC52005
0.9241	High Similarity	NPC119660
0.9241	High Similarity	NPC117463
0.9241	High Similarity	NPC93034
0.9241	High Similarity	NPC470511

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 NPC106461 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	484
0.1-0.2	1039
0.2-0.3	1795
0.3-0.4	2736
0.4-0.5	1694
0.5-0.6	907
0.6-0.7	343
0.7-0.8	107
0.8-0.85	33
0.85-0.9	7
0.9-0.95	4
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9521	High Similarity	NPD2801	Approved
0.9079	High Similarity	NPD5494	Approved
0.9067	High Similarity	NPD3817	Phase 2
0.8933	High Similarity	NPD1934	Approved
0.8904	High Similarity	NPD1511	Approved
0.8811	High Similarity	NPD2796	Approved
0.8784	High Similarity	NPD1512	Approved
0.8758	High Similarity	NPD3882	Suspended
0.875	High Similarity	NPD2393	Clinical (unspecified phase)
0.8654	High Similarity	NPD1247	Approved
0.8591	High Similarity	NPD4378	Clinical (unspecified phase)
0.85	High Similarity	NPD3818	Discontinued
0.8491	Intermediate Similarity	NPD6166	Phase 2
0.8491	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8491	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8466	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8447	Intermediate Similarity	NPD7054	Approved
0.8428	Intermediate Similarity	NPD3926	Phase 2
0.84	Intermediate Similarity	NPD6799	Approved
0.8395	Intermediate Similarity	NPD7472	Approved
0.8333	Intermediate Similarity	NPD5402	Approved
0.8291	Intermediate Similarity	NPD919	Approved
0.8282	Intermediate Similarity	NPD7074	Phase 3
0.825	Intermediate Similarity	NPD6232	Discontinued
0.8243	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8243	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8242	Intermediate Similarity	NPD7808	Phase 3
0.8235	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.8232	Intermediate Similarity	NPD6797	Phase 2
0.8231	Intermediate Similarity	NPD1510	Phase 2
0.821	Intermediate Similarity	NPD7473	Discontinued
0.8194	Intermediate Similarity	NPD4380	Phase 2
0.8188	Intermediate Similarity	NPD1549	Phase 2
0.8182	Intermediate Similarity	NPD7251	Discontinued
0.8165	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8153	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8153	Intermediate Similarity	NPD7819	Suspended
0.8113	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.811	Intermediate Similarity	NPD5844	Phase 1
0.8105	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8089	Intermediate Similarity	NPD6801	Discontinued
0.8082	Intermediate Similarity	NPD1240	Approved
0.8077	Intermediate Similarity	NPD6599	Discontinued
0.8027	Intermediate Similarity	NPD1933	Approved
0.8	Intermediate Similarity	NPD7075	Discontinued
0.8	Intermediate Similarity	NPD920	Approved
0.7987	Intermediate Similarity	NPD3748	Approved
0.7973	Intermediate Similarity	NPD1607	Approved
0.7947	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7911	Intermediate Similarity	NPD7411	Suspended
0.7905	Intermediate Similarity	NPD447	Suspended
0.7895	Intermediate Similarity	NPD1243	Approved
0.7885	Intermediate Similarity	NPD5403	Approved
0.7875	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7871	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7871	Intermediate Similarity	NPD5401	Approved
0.7838	Intermediate Similarity	NPD943	Approved
0.7823	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7815	Intermediate Similarity	NPD2935	Discontinued
0.7812	Intermediate Similarity	NPD1465	Phase 2
0.7784	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7744	Intermediate Similarity	NPD6959	Discontinued
0.7742	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD3750	Approved
0.7692	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7687	Intermediate Similarity	NPD6832	Phase 2
0.7667	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7662	Intermediate Similarity	NPD2800	Approved
0.7651	Intermediate Similarity	NPD5242	Approved
0.7589	Intermediate Similarity	NPD5536	Phase 2
0.7584	Intermediate Similarity	NPD2313	Discontinued
0.7582	Intermediate Similarity	NPD1551	Phase 2
0.758	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7578	Intermediate Similarity	NPD6385	Approved
0.7578	Intermediate Similarity	NPD6386	Approved
0.7569	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7568	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7561	Intermediate Similarity	NPD3749	Approved
0.755	Intermediate Similarity	NPD230	Phase 1
0.7548	Intermediate Similarity	NPD2654	Approved
0.7548	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7546	Intermediate Similarity	NPD5353	Approved
0.7544	Intermediate Similarity	NPD6559	Discontinued
0.7532	Intermediate Similarity	NPD2534	Approved
0.7532	Intermediate Similarity	NPD2533	Approved
0.7532	Intermediate Similarity	NPD2532	Approved
0.753	Intermediate Similarity	NPD7199	Phase 2
0.7516	Intermediate Similarity	NPD2799	Discontinued
0.75	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD2403	Approved
0.75	Intermediate Similarity	NPD7768	Phase 2
0.75	Intermediate Similarity	NPD3018	Phase 2
0.7485	Intermediate Similarity	NPD3787	Discontinued
0.7483	Intermediate Similarity	NPD1613	Approved
0.7483	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7453	Intermediate Similarity	NPD3226	Approved
0.744	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7432	Intermediate Similarity	NPD2798	Approved
0.7423	Intermediate Similarity	NPD6844	Discontinued
0.7419	Intermediate Similarity	NPD2344	Approved
0.7419	Intermediate Similarity	NPD2346	Discontinued
0.7412	Intermediate Similarity	NPD3751	Discontinued
0.7403	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.74	Intermediate Similarity	NPD3027	Phase 3
0.7397	Intermediate Similarity	NPD2981	Phase 2
0.7391	Intermediate Similarity	NPD1653	Approved
0.7389	Intermediate Similarity	NPD4628	Phase 3
0.7375	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD3266	Approved
0.7365	Intermediate Similarity	NPD3267	Approved
0.7363	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7355	Intermediate Similarity	NPD6099	Approved
0.7355	Intermediate Similarity	NPD6100	Approved
0.7347	Intermediate Similarity	NPD2982	Phase 2
0.7347	Intermediate Similarity	NPD2983	Phase 2
0.7345	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD37	Approved
0.731	Intermediate Similarity	NPD17	Approved
0.7299	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7294	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7289	Intermediate Similarity	NPD4965	Approved
0.7289	Intermediate Similarity	NPD4967	Phase 2
0.7289	Intermediate Similarity	NPD4966	Approved
0.7283	Intermediate Similarity	NPD5953	Discontinued
0.7279	Intermediate Similarity	NPD3972	Approved
0.7273	Intermediate Similarity	NPD6651	Approved
0.7267	Intermediate Similarity	NPD7286	Phase 2
0.7267	Intermediate Similarity	NPD9494	Approved
0.7255	Intermediate Similarity	NPD4307	Phase 2
0.7248	Intermediate Similarity	NPD1203	Approved
0.7237	Intermediate Similarity	NPD1296	Phase 2
0.7237	Intermediate Similarity	NPD3268	Approved
0.7233	Intermediate Similarity	NPD2309	Approved
0.7233	Intermediate Similarity	NPD6190	Approved
0.723	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD6234	Discontinued
0.72	Intermediate Similarity	NPD1019	Discontinued
0.7197	Intermediate Similarity	NPD1471	Phase 3
0.719	Intermediate Similarity	NPD6233	Phase 2
0.7186	Intermediate Similarity	NPD5019	Clinical (unspecified phase)
0.7183	Intermediate Similarity	NPD5283	Phase 1
0.7183	Intermediate Similarity	NPD1241	Discontinued
0.7179	Intermediate Similarity	NPD7033	Discontinued
0.7172	Intermediate Similarity	NPD1548	Phase 1
0.7167	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7162	Intermediate Similarity	NPD1608	Approved
0.7162	Intermediate Similarity	NPD9717	Approved
0.7143	Intermediate Similarity	NPD7390	Discontinued
0.7143	Intermediate Similarity	NPD4357	Discontinued
0.7133	Intermediate Similarity	NPD2797	Approved
0.7105	Intermediate Similarity	NPD4908	Phase 1
0.7099	Intermediate Similarity	NPD3688	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD3146	Approved
0.7095	Intermediate Similarity	NPD422	Phase 1
0.7079	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7076	Intermediate Similarity	NPD7229	Phase 3
0.707	Intermediate Similarity	NPD4308	Phase 3
0.7067	Intermediate Similarity	NPD3225	Approved
0.7063	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD7685	Pre-registration
0.7039	Intermediate Similarity	NPD8434	Phase 2
0.7025	Intermediate Similarity	NPD3539	Phase 1
0.7024	Intermediate Similarity	NPD4288	Approved
0.7024	Intermediate Similarity	NPD5977	Approved
0.7024	Intermediate Similarity	NPD5978	Approved
0.7019	Intermediate Similarity	NPD3887	Approved
0.7013	Intermediate Similarity	NPD411	Approved
0.7013	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD6798	Discontinued
0.7007	Intermediate Similarity	NPD9268	Approved
0.7006	Intermediate Similarity	NPD6280	Approved
0.7006	Intermediate Similarity	NPD6279	Approved
0.7006	Intermediate Similarity	NPD7549	Discontinued
0.7005	Intermediate Similarity	NPD5006	Approved
0.7005	Intermediate Similarity	NPD5005	Approved
0.7	Intermediate Similarity	NPD1652	Phase 2
0.6995	Remote Similarity	NPD4363	Phase 3
0.6995	Remote Similarity	NPD4360	Phase 2
0.6994	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD1008	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD3540	Phase 1
0.6981	Remote Similarity	NPD2353	Approved
0.698	Remote Similarity	NPD1610	Phase 2
0.6977	Remote Similarity	NPD5711	Approved
0.6977	Remote Similarity	NPD5710	Approved
0.6954	Remote Similarity	NPD1876	Approved
0.6946	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD5890	Approved
0.6946	Remote Similarity	NPD5889	Approved
0.6941	Remote Similarity	NPD6971	Discontinued
0.6933	Remote Similarity	NPD9269	Phase 2
0.6928	Remote Similarity	NPD2861	Phase 2
0.6923	Remote Similarity	NPD3142	Approved
0.6923	Remote Similarity	NPD3140	Approved
0.6919	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD5307	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