NPASS Compound

Structure

CID276409 OpenBabel06191716082D 27 29 0 0 0 0 0 0 0 0999 V2000 6.9282 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 4.5000 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 -1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 2.5000 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 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 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 1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 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 0.0000 1.0000 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 6.0622 2.5000 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 2.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 4.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 23 1 0 0 0 0 2 24 1 0 0 0 0 3 25 1 0 0 0 0 4 26 1 0 0 0 0 5 9 2 0 0 0 0 5 13 1 0 0 0 0 6 9 1 0 0 0 0 6 14 2 0 0 0 0 7 10 1 0 0 0 0 7 11 2 0 0 0 0 8 12 2 0 0 0 0 8 15 1 0 0 0 0 9 11 1 0 0 0 0 10 16 1 0 0 0 0 10 20 2 0 0 0 0 11 27 1 0 0 0 0 12 16 1 0 0 0 0 12 27 1 0 0 0 0 13 17 2 0 0 0 0 13 23 1 0 0 0 0 14 17 1 0 0 0 0 14 24 1 0 0 0 0 15 19 2 0 0 0 0 15 25 1 0 0 0 0 16 18 2 0 0 0 0 17 21 1 0 0 0 0 18 19 1 0 0 0 0 18 22 1 0 0 0 0 19 26 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	374.1
Volume:	360.741
LogP:	2.917
LogD:	2.4
LogS:	-4.412
# Rotatable Bonds:	5
TPSA:	107.59
# H-Bond Aceptor:	8
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.702
Synthetic Accessibility Score:	2.459
Fsp3:	0.211
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.887
MDCK Permeability:	2.7587446311372332e-05
Pgp-inhibitor:	0.989
Pgp-substrate:	0.006
Human Intestinal Absorption (HIA):	0.031
20% Bioavailability (F20%):	0.006
30% Bioavailability (F30%):	0.018

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.007
Plasma Protein Binding (PPB):	77.15535736083984%
Volume Distribution (VD):	0.809
Pgp-substrate:	28.670225143432617%

ADMET: Metabolism

CYP1A2-inhibitor:	0.438
CYP1A2-substrate:	0.983
CYP2C19-inhibitor:	0.146
CYP2C19-substrate:	0.623
CYP2C9-inhibitor:	0.625
CYP2C9-substrate:	0.791
CYP2D6-inhibitor:	0.044
CYP2D6-substrate:	0.887
CYP3A4-inhibitor:	0.409
CYP3A4-substrate:	0.366

ADMET: Excretion

Clearance (CL):	4.238
Half-life (T1/2):	0.804

ADMET: Toxicity

hERG Blockers:	0.235
Human Hepatotoxicity (H-HT):	0.092
Drug-inuced Liver Injury (DILI):	0.696
AMES Toxicity:	0.177
Rat Oral Acute Toxicity:	0.093
Maximum Recommended Daily Dose:	0.133
Skin Sensitization:	0.839
Carcinogencity:	0.022
Eye Corrosion:	0.003
Eye Irritation:	0.389
Respiratory Toxicity:	0.349

Download Data

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

Natural Product: NPC276409

Natural Product ID:	NPC276409
*Common Name:**	5-Hydroxy-2-(4-Hydroxy-3,5-Dimethoxyphenyl)-6,7-Dimethoxychromen-4-One
IUPAC Name:	5-hydroxy-2-(4-hydroxy-3,5-dimethoxyphenyl)-6,7-dimethoxychromen-4-one
Synonyms:
Standard InCHIKey:	XEHLDSAKZSXOFK-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C19H18O8/c1-23-13-5-9(6-14(24-2)17(13)21)11-7-10(20)16-12(27-11)8-15(25-3)19(26-4)18(16)22/h5-8,21-22H,1-4H3
SMILES:	COc1cc2oc(cc(=O)c2c(c1OC)O)c1cc(OC)c(c(c1)OC)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1524286
PubChem CID:	16681753
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
NPO14201	Riccia fluitans	Species	Ricciaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6388	Mulguraea tridens	Species	Verbenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14027	Dacryodes normandii	Species	Burseraceae	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	2
Potency	27

Activity Type	# Activity
Cell Line	1
Individual Protein	20
Organism	2
Others	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT47	Individual Protein	ATP-dependent DNA helicase Q1	Homo sapiens	Potency	=	35481.3	nM	PMID[528101]
NPT48	Individual Protein	Lysine-specific demethylase 4D-like	Homo sapiens	Potency	=	39810.7	nM	PMID[528101]
NPT51	Individual Protein	Microtubule-associated protein tau	Homo sapiens	Potency	=	39810.7	nM	PMID[528101]
NPT59	Individual Protein	DNA polymerase beta	Homo sapiens	Potency	=	28183.8	nM	PMID[528101]
NPT64	Individual Protein	ATPase family AAA domain-containing protein 5	Homo sapiens	Potency	n.a.	11577.4	nM	PMID[528101]
NPT65	Cell Line	HepG2	Homo sapiens	Potency	n.a.	12589.3	nM	PMID[528101]
NPT199	Individual Protein	DNA polymerase kappa	Homo sapiens	Potency	n.a.	79432.8	nM	PMID[528101]
NPT100	Individual Protein	Glutaminase kidney isoform, mitochondrial	Homo sapiens	Potency	n.a.	12589.3	nM	PMID[528101]
NPT478	Individual Protein	Ataxin-2	Homo sapiens	Potency	n.a.	39810.7	nM	PMID[528101]
NPT50	Individual Protein	Tyrosyl-DNA phosphodiesterase 1	Homo sapiens	Potency	n.a.	16360.1	nM	PMID[528101]
NPT4015	Individual Protein	Matrix metalloproteinase 14	Homo sapiens	IC50	>	80000.0	nM	PMID[528101]
NPT535	Individual Protein	Parathyroid hormone receptor	Homo sapiens	Potency	n.a.	70794.6	nM	PMID[528101]
NPT105	Individual Protein	Muscleblind-like protein 1	Homo sapiens	Potency	n.a.	17782.8	nM	PMID[528101]
NPT49	Individual Protein	DNA-(apurinic or apyrimidinic site) lyase	Homo sapiens	Potency	n.a.	25118.9	nM	PMID[528101]
NPT312	Organism	Saccharomyces cerevisiae	Saccharomyces cerevisiae	Potency	=	10000.0	nM	PMID[528101]
NPT2	Others	Unspecified		Potency	=	29092.9	nM	PMID[528101]
NPT8	Individual Protein	DNA polymerase iota	Homo sapiens	Potency	n.a.	79432.8	nM	PMID[528101]
NPT9	Individual Protein	DNA polymerase eta	Homo sapiens	Potency	n.a.	22387.2	nM	PMID[528101]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Potency	n.a.	11689.1	nM	PMID[528101]
NPT2	Others	Unspecified		Potency	n.a.	25118.9	nM	PMID[528101]
NPT821	Individual Protein	Werner syndrome ATP-dependent helicase	Homo sapiens	Potency	n.a.	63095.7	nM	PMID[528101]
NPT755	Individual Protein	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	Homo sapiens	Potency	n.a.	44668.4	nM	PMID[528101]
NPT2	Others	Unspecified		Potency	n.a.	29092.9	nM	PMID[528101]
NPT2	Others	Unspecified		IC50	>	80000.0	nM	PMID[528101]
NPT861	Individual Protein	Isocitrate dehydrogenase [NADP] cytoplasmic	Homo sapiens	Potency	n.a.	18356.4	nM	PMID[528101]
NPT2	Others	Unspecified		Potency	n.a.	10000.0	nM	PMID[528101]
NPT9	Individual Protein	DNA polymerase eta	Homo sapiens	Potency	n.a.	67455.5	nM	PMID[528101]
NPT2	Others	Unspecified		Potency	n.a.	22387.2	nM	PMID[528101]

☑ 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 NPC276409 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	428
0.1-0.2	1900
0.2-0.3	4952
0.3-0.4	11335
0.4-0.5	6151
0.5-0.6	3737
0.6-0.7	5012
0.7-0.8	4793
0.8-0.85	2219
0.85-0.9	1221
0.9-0.95	675
0.95-1	274

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC75279
1.0	High Similarity	NPC250822
0.9932	High Similarity	NPC138360
0.9932	High Similarity	NPC183597
0.9932	High Similarity	NPC280339
0.9932	High Similarity	NPC146165
0.9932	High Similarity	NPC92659
0.9932	High Similarity	NPC201136
0.9932	High Similarity	NPC128863
0.9932	High Similarity	NPC208197
0.9932	High Similarity	NPC50715
0.9932	High Similarity	NPC227325
0.9932	High Similarity	NPC2476
0.9932	High Similarity	NPC196439
0.9932	High Similarity	NPC167815
0.9932	High Similarity	NPC4455
0.9932	High Similarity	NPC163780
0.9865	High Similarity	NPC474520
0.9864	High Similarity	NPC145379
0.9864	High Similarity	NPC69394
0.9864	High Similarity	NPC231018
0.9864	High Similarity	NPC183878
0.9864	High Similarity	NPC255350
0.9864	High Similarity	NPC274327
0.9864	High Similarity	NPC47781
0.9864	High Similarity	NPC22519
0.9864	High Similarity	NPC176775
0.9864	High Similarity	NPC160951
0.9799	High Similarity	NPC472438
0.9799	High Similarity	NPC78302
0.9799	High Similarity	NPC235215
0.9799	High Similarity	NPC7973
0.9799	High Similarity	NPC75215
0.9799	High Similarity	NPC93376
0.9799	High Similarity	NPC227192
0.9799	High Similarity	NPC189179
0.9799	High Similarity	NPC224137
0.9799	High Similarity	NPC29841
0.9797	High Similarity	NPC213622
0.9797	High Similarity	NPC20830
0.9797	High Similarity	NPC256612
0.9796	High Similarity	NPC212678
0.9796	High Similarity	NPC131624
0.9796	High Similarity	NPC275836
0.9796	High Similarity	NPC275722
0.9796	High Similarity	NPC241498
0.9796	High Similarity	NPC162313
0.9796	High Similarity	NPC120163
0.9796	High Similarity	NPC25270
0.9796	High Similarity	NPC142540
0.9796	High Similarity	NPC198826
0.9796	High Similarity	NPC57030
0.9796	High Similarity	NPC256283
0.9796	High Similarity	NPC222830
0.9796	High Similarity	NPC239128
0.9796	High Similarity	NPC187498
0.9796	High Similarity	NPC71334
0.9796	High Similarity	NPC156222
0.9796	High Similarity	NPC293183
0.9796	High Similarity	NPC83508
0.9796	High Similarity	NPC188203
0.9796	High Similarity	NPC301323
0.9796	High Similarity	NPC100887
0.9733	High Similarity	NPC19687
0.9733	High Similarity	NPC25495
0.9733	High Similarity	NPC18607
0.9733	High Similarity	NPC261004
0.9733	High Similarity	NPC300943
0.9733	High Similarity	NPC18772
0.9733	High Similarity	NPC105242
0.9733	High Similarity	NPC152166
0.9733	High Similarity	NPC130894
0.9733	High Similarity	NPC204854
0.9733	High Similarity	NPC115798
0.9733	High Similarity	NPC143828
0.9733	High Similarity	NPC9609
0.9733	High Similarity	NPC191459
0.9733	High Similarity	NPC22472
0.9733	High Similarity	NPC176300
0.9733	High Similarity	NPC253634
0.9733	High Similarity	NPC288669
0.9733	High Similarity	NPC4481
0.9733	High Similarity	NPC7846
0.9732	High Similarity	NPC49824
0.9732	High Similarity	NPC268161
0.9732	High Similarity	NPC98661
0.9732	High Similarity	NPC100916
0.9732	High Similarity	NPC55619
0.9732	High Similarity	NPC247017
0.9732	High Similarity	NPC200388
0.9728	High Similarity	NPC208043
0.9728	High Similarity	NPC226973
0.9726	High Similarity	NPC177298
0.9726	High Similarity	NPC328119
0.9726	High Similarity	NPC48479
0.9667	High Similarity	NPC470402
0.9667	High Similarity	NPC163524
0.9667	High Similarity	NPC203891
0.9667	High Similarity	NPC110070
0.9667	High Similarity	NPC101830
0.9667	High Similarity	NPC287979
0.9667	High Similarity	NPC176665
0.9667	High Similarity	NPC305663
0.9664	High Similarity	NPC26227
0.9664	High Similarity	NPC201451
0.9664	High Similarity	NPC44079
0.9662	High Similarity	NPC39732
0.9662	High Similarity	NPC60972
0.966	High Similarity	NPC306821
0.966	High Similarity	NPC184136
0.9658	High Similarity	NPC120464
0.9603	High Similarity	NPC193842
0.96	High Similarity	NPC266960
0.96	High Similarity	NPC292107
0.96	High Similarity	NPC245546
0.96	High Similarity	NPC43243
0.96	High Similarity	NPC178854
0.96	High Similarity	NPC472916
0.9597	High Similarity	NPC250557
0.9597	High Similarity	NPC86485
0.9597	High Similarity	NPC246204
0.9597	High Similarity	NPC58382
0.9597	High Similarity	NPC280937
0.9597	High Similarity	NPC162351
0.9595	High Similarity	NPC28274
0.9595	High Similarity	NPC308451
0.9595	High Similarity	NPC133953
0.9595	High Similarity	NPC50403
0.9592	High Similarity	NPC296197
0.9592	High Similarity	NPC137062
0.9592	High Similarity	NPC17286
0.9592	High Similarity	NPC183950
0.9592	High Similarity	NPC287101
0.9592	High Similarity	NPC223579
0.9592	High Similarity	NPC259713
0.9592	High Similarity	NPC216318
0.9592	High Similarity	NPC52005
0.9589	High Similarity	NPC55557
0.9589	High Similarity	NPC33265
0.9589	High Similarity	NPC30647
0.9589	High Similarity	NPC61871
0.9589	High Similarity	NPC62536
0.9539	High Similarity	NPC476980
0.9539	High Similarity	NPC246478
0.9536	High Similarity	NPC222814
0.9536	High Similarity	NPC78225
0.9536	High Similarity	NPC96167
0.9536	High Similarity	NPC36852
0.9536	High Similarity	NPC241904
0.9536	High Similarity	NPC475267
0.9536	High Similarity	NPC162869
0.9536	High Similarity	NPC469584
0.9536	High Similarity	NPC245758
0.9536	High Similarity	NPC262286
0.9536	High Similarity	NPC48208
0.9536	High Similarity	NPC472913
0.9536	High Similarity	NPC474836
0.9536	High Similarity	NPC472914
0.9536	High Similarity	NPC474208
0.9536	High Similarity	NPC300727
0.9536	High Similarity	NPC156057
0.9536	High Similarity	NPC472910
0.9536	High Similarity	NPC472911
0.9533	High Similarity	NPC32557
0.9533	High Similarity	NPC2928
0.9533	High Similarity	NPC214138
0.9533	High Similarity	NPC189960
0.953	High Similarity	NPC123886
0.953	High Similarity	NPC301123
0.953	High Similarity	NPC289968
0.953	High Similarity	NPC101996
0.953	High Similarity	NPC199100
0.953	High Similarity	NPC120537
0.953	High Similarity	NPC180234
0.953	High Similarity	NPC134677
0.953	High Similarity	NPC27208
0.953	High Similarity	NPC471982
0.9527	High Similarity	NPC45873
0.9527	High Similarity	NPC219330
0.9524	High Similarity	NPC195202
0.9521	High Similarity	NPC302408
0.9521	High Similarity	NPC283002
0.9481	High Similarity	NPC470459
0.9481	High Similarity	NPC272064
0.9477	High Similarity	NPC258331
0.9477	High Similarity	NPC266314
0.9474	High Similarity	NPC476242
0.947	High Similarity	NPC138243
0.947	High Similarity	NPC235165
0.947	High Similarity	NPC274730
0.947	High Similarity	NPC68093
0.947	High Similarity	NPC255106
0.947	High Similarity	NPC265511
0.947	High Similarity	NPC191146
0.9467	High Similarity	NPC179126
0.9467	High Similarity	NPC88645
0.9467	High Similarity	NPC270620
0.9467	High Similarity	NPC292214
0.9467	High Similarity	NPC236223
0.9467	High Similarity	NPC124714

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 NPC276409 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	404
0.1-0.2	990
0.2-0.3	1869
0.3-0.4	2677
0.4-0.5	1729
0.5-0.6	961
0.6-0.7	354
0.7-0.8	112
0.8-0.85	30
0.85-0.9	16
0.9-0.95	7
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9864	High Similarity	NPD2801	Approved
0.9272	High Similarity	NPD1934	Approved
0.9252	High Similarity	NPD1511	Approved
0.9128	High Similarity	NPD1512	Approved
0.9091	High Similarity	NPD3882	Suspended
0.9085	High Similarity	NPD2393	Clinical (unspecified phase)
0.9026	High Similarity	NPD3817	Phase 2
0.8938	High Similarity	NPD3818	Discontinued
0.8931	High Similarity	NPD6166	Phase 2
0.8931	High Similarity	NPD6167	Clinical (unspecified phase)
0.8931	High Similarity	NPD6168	Clinical (unspecified phase)
0.8896	High Similarity	NPD4338	Clinical (unspecified phase)
0.8882	High Similarity	NPD7054	Approved
0.8827	High Similarity	NPD7472	Approved
0.8726	High Similarity	NPD4868	Clinical (unspecified phase)
0.8712	High Similarity	NPD7074	Phase 3
0.8684	High Similarity	NPD4378	Clinical (unspecified phase)
0.8659	High Similarity	NPD6797	Phase 2
0.8606	High Similarity	NPD7251	Discontinued
0.8562	High Similarity	NPD5494	Approved
0.8554	High Similarity	NPD7808	Phase 3
0.8526	High Similarity	NPD4380	Phase 2
0.8457	Intermediate Similarity	NPD6232	Discontinued
0.8438	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8428	Intermediate Similarity	NPD5402	Approved
0.8415	Intermediate Similarity	NPD7473	Discontinued
0.8365	Intermediate Similarity	NPD1465	Phase 2
0.8344	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8344	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD1510	Phase 2
0.8323	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8323	Intermediate Similarity	NPD7075	Discontinued
0.8289	Intermediate Similarity	NPD1549	Phase 2
0.8278	Intermediate Similarity	NPD2796	Approved
0.8258	Intermediate Similarity	NPD6799	Approved
0.8214	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8188	Intermediate Similarity	NPD943	Approved
0.8188	Intermediate Similarity	NPD1240	Approved
0.8187	Intermediate Similarity	NPD6801	Discontinued
0.8171	Intermediate Similarity	NPD1247	Approved
0.817	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8137	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8137	Intermediate Similarity	NPD7819	Suspended
0.8095	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8095	Intermediate Similarity	NPD5844	Phase 1
0.8086	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8079	Intermediate Similarity	NPD1607	Approved
0.8072	Intermediate Similarity	NPD3926	Phase 2
0.8061	Intermediate Similarity	NPD6959	Discontinued
0.8013	Intermediate Similarity	NPD230	Phase 1
0.8012	Intermediate Similarity	NPD7411	Suspended
0.7987	Intermediate Similarity	NPD5403	Approved
0.7973	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.795	Intermediate Similarity	NPD6599	Discontinued
0.7922	Intermediate Similarity	NPD2935	Discontinued
0.7919	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7895	Intermediate Similarity	NPD447	Suspended
0.7885	Intermediate Similarity	NPD2800	Approved
0.7875	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7862	Intermediate Similarity	NPD5401	Approved
0.7849	Intermediate Similarity	NPD6559	Discontinued
0.7834	Intermediate Similarity	NPD3750	Approved
0.7831	Intermediate Similarity	NPD919	Approved
0.7829	Intermediate Similarity	NPD1613	Approved
0.7829	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7826	Intermediate Similarity	NPD1653	Approved
0.775	Intermediate Similarity	NPD2534	Approved
0.775	Intermediate Similarity	NPD2532	Approved
0.775	Intermediate Similarity	NPD2533	Approved
0.7748	Intermediate Similarity	NPD3027	Phase 3
0.7742	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.774	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7725	Intermediate Similarity	NPD6234	Discontinued
0.7706	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD1551	Phase 2
0.7673	Intermediate Similarity	NPD6190	Approved
0.7665	Intermediate Similarity	NPD3749	Approved
0.7633	Intermediate Similarity	NPD7199	Phase 2
0.7616	Intermediate Similarity	NPD9494	Approved
0.7613	Intermediate Similarity	NPD6651	Approved
0.761	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7605	Intermediate Similarity	NPD7768	Phase 2
0.7584	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.758	Intermediate Similarity	NPD6099	Approved
0.758	Intermediate Similarity	NPD6100	Approved
0.7578	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7561	Intermediate Similarity	NPD3226	Approved
0.7554	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7548	Intermediate Similarity	NPD1933	Approved
0.7547	Intermediate Similarity	NPD1243	Approved
0.7547	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7546	Intermediate Similarity	NPD920	Approved
0.7544	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD2344	Approved
0.753	Intermediate Similarity	NPD37	Approved
0.7516	Intermediate Similarity	NPD3748	Approved
0.7516	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD3751	Discontinued
0.75	Intermediate Similarity	NPD4966	Approved
0.75	Intermediate Similarity	NPD4965	Approved
0.75	Intermediate Similarity	NPD4967	Phase 2
0.75	Intermediate Similarity	NPD4628	Phase 3
0.7486	Intermediate Similarity	NPD5953	Discontinued
0.7485	Intermediate Similarity	NPD3787	Discontinued
0.7472	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7469	Intermediate Similarity	NPD7390	Discontinued
0.7468	Intermediate Similarity	NPD2313	Discontinued
0.7459	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7443	Intermediate Similarity	NPD7685	Pre-registration
0.7423	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7414	Intermediate Similarity	NPD7228	Approved
0.7405	Intermediate Similarity	NPD2799	Discontinued
0.7401	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.74	Intermediate Similarity	NPD9269	Phase 2
0.7371	Intermediate Similarity	NPD7286	Phase 2
0.7368	Intermediate Similarity	NPD1203	Approved
0.7346	Intermediate Similarity	NPD2309	Approved
0.7338	Intermediate Similarity	NPD6832	Phase 2
0.7321	Intermediate Similarity	NPD6844	Discontinued
0.7317	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD2346	Discontinued
0.7301	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD1548	Phase 1
0.7284	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD3018	Phase 2
0.7244	Intermediate Similarity	NPD3268	Approved
0.7241	Intermediate Similarity	NPD5242	Approved
0.7238	Intermediate Similarity	NPD8434	Phase 2
0.7235	Intermediate Similarity	NPD5353	Approved
0.7226	Intermediate Similarity	NPD4908	Phase 1
0.7222	Intermediate Similarity	NPD2654	Approved
0.7219	Intermediate Similarity	NPD422	Phase 1
0.7215	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD2798	Approved
0.7204	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD2403	Approved
0.7197	Intermediate Similarity	NPD6233	Phase 2
0.7188	Intermediate Similarity	NPD7033	Discontinued
0.7184	Intermediate Similarity	NPD5711	Approved
0.7184	Intermediate Similarity	NPD5710	Approved
0.7181	Intermediate Similarity	NPD6777	Approved
0.7181	Intermediate Similarity	NPD6778	Approved
0.7181	Intermediate Similarity	NPD6782	Approved
0.7181	Intermediate Similarity	NPD6776	Approved
0.7181	Intermediate Similarity	NPD6780	Approved
0.7181	Intermediate Similarity	NPD6781	Approved
0.7181	Intermediate Similarity	NPD6779	Approved
0.7171	Intermediate Similarity	NPD9717	Approved
0.7167	Intermediate Similarity	NPD8313	Approved
0.7167	Intermediate Similarity	NPD8312	Approved
0.716	Intermediate Similarity	NPD6386	Approved
0.716	Intermediate Similarity	NPD6385	Approved
0.7152	Intermediate Similarity	NPD4357	Discontinued
0.7143	Intermediate Similarity	NPD2797	Approved
0.7134	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD9268	Approved
0.7124	Intermediate Similarity	NPD2983	Phase 2
0.7124	Intermediate Similarity	NPD2982	Phase 2
0.7114	Intermediate Similarity	NPD5536	Phase 2
0.7105	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD1610	Phase 2
0.7097	Intermediate Similarity	NPD4360	Phase 2
0.7097	Intermediate Similarity	NPD4363	Phase 3
0.7081	Intermediate Similarity	NPD4308	Phase 3
0.7078	Intermediate Similarity	NPD3225	Approved
0.7068	Intermediate Similarity	NPD7435	Discontinued
0.7062	Intermediate Similarity	NPD8151	Discontinued
0.7059	Intermediate Similarity	NPD2981	Phase 2
0.7059	Intermediate Similarity	NPD1608	Approved
0.7051	Intermediate Similarity	NPD2861	Phase 2
0.7049	Intermediate Similarity	NPD8150	Discontinued
0.7047	Intermediate Similarity	NPD7584	Approved
0.7025	Intermediate Similarity	NPD411	Approved
0.7025	Intermediate Similarity	NPD6798	Discontinued
0.7017	Intermediate Similarity	NPD7549	Discontinued
0.7013	Intermediate Similarity	NPD4749	Approved
0.7012	Intermediate Similarity	NPD1652	Phase 2
0.7006	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD2899	Discontinued
0.6994	Remote Similarity	NPD7266	Discontinued
0.699	Remote Similarity	NPD7783	Phase 2
0.699	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD7229	Phase 3
0.6979	Remote Similarity	NPD7697	Approved
0.6979	Remote Similarity	NPD7696	Phase 3
0.6979	Remote Similarity	NPD7698	Approved
0.6968	Remote Similarity	NPD4362	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD4361	Phase 2
0.6964	Remote Similarity	NPD1940	Clinical (unspecified phase)
0.6962	Remote Similarity	NPD4625	Phase 3
0.6961	Remote Similarity	NPD7240	Approved
0.6959	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6948	Remote Similarity	NPD1481	Phase 2
0.6943	Remote Similarity	NPD7870	Phase 2
0.6943	Remote Similarity	NPD7871	Phase 2
0.6939	Remote Similarity	NPD228	Approved
0.6936	Remote Similarity	NPD4288	Approved
0.6927	Remote Similarity	NPD6823	Phase 2

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