NPASS Compound

Structure

CID45873 OpenBabel06191715382D 21 23 0 0 0 0 0 0 0 0999 V2000 1.7321 1.0000 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 2.5981 1.5000 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 -1.7321 -2.0000 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 1.7321 0.0000 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 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -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 -2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 3 1 0 0 0 0 1 7 2 0 0 0 0 2 4 2 0 0 0 0 2 7 1 0 0 0 0 3 8 2 0 0 0 0 4 8 1 0 0 0 0 5 9 2 0 0 0 0 5 11 1 0 0 0 0 6 10 1 0 0 0 0 6 12 2 0 0 0 0 7 12 1 0 0 0 0 8 16 1 0 0 0 0 9 10 1 0 0 0 0 9 15 1 0 0 0 0 10 17 2 0 0 0 0 11 13 2 0 0 0 0 11 18 1 0 0 0 0 12 21 1 0 0 0 0 13 14 1 0 0 0 0 13 19 1 0 0 0 0 14 15 2 0 0 0 0 14 20 1 0 0 0 0 15 21 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	286.05
Volume:	273.977
LogP:	2.643
LogD:	1.541
LogS:	-3.759
# Rotatable Bonds:	1
TPSA:	111.13
# H-Bond Aceptor:	6
# H-Bond Donor:	4
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.511
Synthetic Accessibility Score:	2.451
Fsp3:	0.0
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.083
MDCK Permeability:	1.0130223927262705e-05
Pgp-inhibitor:	0.003
Pgp-substrate:	0.084
Human Intestinal Absorption (HIA):	0.041
20% Bioavailability (F20%):	0.989
30% Bioavailability (F30%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.005
Plasma Protein Binding (PPB):	97.5865249633789%
Volume Distribution (VD):	0.498
Pgp-substrate:	7.037069797515869%

ADMET: Metabolism

CYP1A2-inhibitor:	0.961
CYP1A2-substrate:	0.104
CYP2C19-inhibitor:	0.062
CYP2C19-substrate:	0.051
CYP2C9-inhibitor:	0.525
CYP2C9-substrate:	0.537
CYP2D6-inhibitor:	0.439
CYP2D6-substrate:	0.237
CYP3A4-inhibitor:	0.196
CYP3A4-substrate:	0.094

ADMET: Excretion

Clearance (CL):	7.105
Half-life (T1/2):	0.911

ADMET: Toxicity

hERG Blockers:	0.037
Human Hepatotoxicity (H-HT):	0.137
Drug-inuced Liver Injury (DILI):	0.977
AMES Toxicity:	0.581
Rat Oral Acute Toxicity:	0.193
Maximum Recommended Daily Dose:	0.451
Skin Sensitization:	0.941
Carcinogencity:	0.325
Eye Corrosion:	0.003
Eye Irritation:	0.889
Respiratory Toxicity:	0.124

Download Data

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

Natural Product: NPC45873

Natural Product ID:	NPC45873
*Common Name:**	6,7,8-Trihydroxy-2-(4-Hydroxyphenyl)Chromen-4-One
IUPAC Name:	6,7,8-trihydroxy-2-(4-hydroxyphenyl)chromen-4-one
Synonyms:	NSC-76988
Standard InCHIKey:	BYXJBJUCNOOYRF-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C15H10O6/c16-8-3-1-7(2-4-8)12-6-10(17)9-5-11(18)13(19)14(20)15(9)21-12/h1-6,16,18-20H
SMILES:	Oc1ccc(cc1)c1cc(=O)c2c(o1)c(O)c(c(c2)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL519331
PubChem CID:	16657778
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001615] Flavones

*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
NPO23190	Aspergillus parasiticus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11678666]
NPO23190	Aspergillus parasiticus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12027772]
NPO23098	Aglaia silvestris	Species	Meliaceae	Eukaryota	n.a.	fruit	n.a.	PMID[15132542]
NPO23098	Aglaia silvestris	Species	Meliaceae	Eukaryota	n.a.	twig	n.a.	PMID[15132542]
NPO23190	Aspergillus parasiticus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15184162]
NPO23527	Croton laevigatus	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20307086]
NPO23190	Aspergillus parasiticus	Species	Aspergillaceae	Eukaryota	n.a.	latex	n.a.	PMID[21854017]
NPO22238	Inula falconeri	Species	Asteraceae	Eukaryota	aerial parts	Tibet, China	n.a.	PMID[21924800]
NPO22803	Neolitsea parvigemma	Species	Lauraceae	Eukaryota	n.a.	leaf	n.a.	PMID[21941915]
NPO23190	Aspergillus parasiticus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22103394]
NPO23190	Aspergillus parasiticus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24738739]
NPO10680	Cistanche deserticola	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25900014]
NPO4608	Aesculus californica	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO10680	Cistanche deserticola	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21872	Hemerocallis longituba	Species	Asphodelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21872	Hemerocallis longituba	Species	Asphodelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4608	Aesculus californica	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10680	Cistanche deserticola	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10680	Cistanche deserticola	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO4608	Aesculus californica	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO10680	Cistanche deserticola	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO20354	Genista cadasonensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10680	Cistanche deserticola	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22803	Neolitsea parvigemma	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22695	Hemsleya chinensis	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21872	Hemerocallis longituba	Species	Asphodelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23527	Croton laevigatus	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22238	Inula falconeri	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20609	Mikania banisteriae	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23190	Aspergillus parasiticus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23278	Colubrina granulosa	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23098	Aglaia silvestris	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21501	Mycale tenuispiculata	Species	Mycalidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17815	Verbesina occidentalis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24362	Polygonum plebejum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23915	Asplenium fontanum	Species	Aspleniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18855	Isolona ghesquierei	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23496	Agathosma spinosa	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4608	Aesculus californica	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

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

NP Quantity Composition/Concentration

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

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

Biological Activity

Activity Type	# Activity
ED50	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	ED50	=	22.0	ug ml-1	PMID[546022]

☑ 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 NPC45873 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	588
0.1-0.2	2324
0.2-0.3	6102
0.3-0.4	11571
0.4-0.5	4598
0.5-0.6	4286
0.6-0.7	5206
0.7-0.8	4747
0.8-0.85	1653
0.85-0.9	918
0.9-0.95	455
0.95-1	249

Similarity Score	Similarity Level	Natural Product ID
0.993	High Similarity	NPC17286
0.993	High Similarity	NPC216318
0.993	High Similarity	NPC296197
0.993	High Similarity	NPC259713
0.986	High Similarity	NPC118726
0.986	High Similarity	NPC12367
0.9793	High Similarity	NPC225731
0.9793	High Similarity	NPC251110
0.979	High Similarity	NPC275772
0.979	High Similarity	NPC239312
0.979	High Similarity	NPC168803
0.979	High Similarity	NPC130230
0.9728	High Similarity	NPC20830
0.9728	High Similarity	NPC256612
0.9726	High Similarity	NPC83508
0.9726	High Similarity	NPC198826
0.9726	High Similarity	NPC239128
0.9726	High Similarity	NPC187498
0.9726	High Similarity	NPC222830
0.9726	High Similarity	NPC57030
0.9726	High Similarity	NPC71334
0.9726	High Similarity	NPC131624
0.9726	High Similarity	NPC301323
0.9726	High Similarity	NPC188203
0.9726	High Similarity	NPC293183
0.9726	High Similarity	NPC27208
0.9726	High Similarity	NPC156222
0.9726	High Similarity	NPC100887
0.9726	High Similarity	NPC256283
0.9726	High Similarity	NPC120163
0.9726	High Similarity	NPC212678
0.9726	High Similarity	NPC275836
0.9726	High Similarity	NPC275722
0.9726	High Similarity	NPC25270
0.9726	High Similarity	NPC241498
0.9726	High Similarity	NPC162313
0.9724	High Similarity	NPC248102
0.9724	High Similarity	NPC61620
0.966	High Similarity	NPC183878
0.966	High Similarity	NPC47781
0.966	High Similarity	NPC22519
0.966	High Similarity	NPC88645
0.966	High Similarity	NPC160951
0.966	High Similarity	NPC255350
0.966	High Similarity	NPC292214
0.966	High Similarity	NPC206238
0.966	High Similarity	NPC231018
0.966	High Similarity	NPC167091
0.966	High Similarity	NPC274327
0.966	High Similarity	NPC145379
0.966	High Similarity	NPC69394
0.966	High Similarity	NPC271779
0.966	High Similarity	NPC176775
0.9655	High Similarity	NPC195351
0.965	High Similarity	NPC70136
0.9595	High Similarity	NPC50715
0.9595	High Similarity	NPC163780
0.9595	High Similarity	NPC196439
0.9595	High Similarity	NPC201136
0.9595	High Similarity	NPC128863
0.9595	High Similarity	NPC2928
0.9595	High Similarity	NPC208197
0.9595	High Similarity	NPC183597
0.9595	High Similarity	NPC213622
0.9595	High Similarity	NPC146165
0.9595	High Similarity	NPC167815
0.9595	High Similarity	NPC92659
0.9595	High Similarity	NPC4455
0.9595	High Similarity	NPC201451
0.9595	High Similarity	NPC26227
0.9595	High Similarity	NPC2476
0.9595	High Similarity	NPC44079
0.9595	High Similarity	NPC138360
0.9595	High Similarity	NPC280339
0.9595	High Similarity	NPC227325
0.9592	High Similarity	NPC39732
0.9592	High Similarity	NPC199100
0.9592	High Similarity	NPC120537
0.9592	High Similarity	NPC39007
0.9592	High Similarity	NPC142540
0.9592	High Similarity	NPC180234
0.9592	High Similarity	NPC60972
0.9592	High Similarity	NPC161277
0.9592	High Similarity	NPC101996
0.9589	High Similarity	NPC306821
0.9589	High Similarity	NPC77858
0.9589	High Similarity	NPC184136
0.9586	High Similarity	NPC196277
0.9586	High Similarity	NPC43669
0.9586	High Similarity	NPC194856
0.9586	High Similarity	NPC276930
0.9586	High Similarity	NPC272721
0.958	High Similarity	NPC279121
0.953	High Similarity	NPC266960
0.953	High Similarity	NPC245546
0.953	High Similarity	NPC43243
0.953	High Similarity	NPC247017
0.953	High Similarity	NPC98661
0.953	High Similarity	NPC472916
0.953	High Similarity	NPC49824
0.9527	High Similarity	NPC75279
0.9527	High Similarity	NPC250822
0.9527	High Similarity	NPC276409
0.9524	High Similarity	NPC171010
0.9524	High Similarity	NPC149614
0.9524	High Similarity	NPC226973
0.9524	High Similarity	NPC208043
0.9524	High Similarity	NPC308451
0.9521	High Similarity	NPC223579
0.9521	High Similarity	NPC52005
0.9521	High Similarity	NPC183950
0.9521	High Similarity	NPC287101
0.9521	High Similarity	NPC137062
0.9517	High Similarity	NPC61871
0.9517	High Similarity	NPC55557
0.9517	High Similarity	NPC51443
0.9517	High Similarity	NPC77378
0.9517	High Similarity	NPC207729
0.9517	High Similarity	NPC74881
0.9517	High Similarity	NPC30647
0.951	High Similarity	NPC175013
0.947	High Similarity	NPC476980
0.9467	High Similarity	NPC224137
0.9467	High Similarity	NPC101830
0.9467	High Similarity	NPC93376
0.9467	High Similarity	NPC189179
0.9467	High Similarity	NPC75215
0.9467	High Similarity	NPC99597
0.9467	High Similarity	NPC470402
0.9467	High Similarity	NPC305663
0.9467	High Similarity	NPC110070
0.9467	High Similarity	NPC210084
0.9467	High Similarity	NPC163524
0.9467	High Similarity	NPC287979
0.9467	High Similarity	NPC227192
0.9467	High Similarity	NPC203891
0.9467	High Similarity	NPC176665
0.9459	High Similarity	NPC209487
0.9459	High Similarity	NPC131266
0.9459	High Similarity	NPC301123
0.9459	High Similarity	NPC269451
0.9459	High Similarity	NPC216769
0.9459	High Similarity	NPC35763
0.9459	High Similarity	NPC55205
0.9459	High Similarity	NPC245382
0.9459	High Similarity	NPC181209
0.9459	High Similarity	NPC100263
0.9459	High Similarity	NPC100971
0.9459	High Similarity	NPC291802
0.9459	High Similarity	NPC121522
0.9456	High Similarity	NPC179183
0.9456	High Similarity	NPC29231
0.9456	High Similarity	NPC62042
0.9452	High Similarity	NPC120464
0.9452	High Similarity	NPC218490
0.9452	High Similarity	NPC287395
0.9452	High Similarity	NPC183655
0.9448	High Similarity	NPC20791
0.9448	High Similarity	NPC179271
0.9408	High Similarity	NPC29876
0.9408	High Similarity	NPC259456
0.9408	High Similarity	NPC258331
0.9408	High Similarity	NPC167678
0.9404	High Similarity	NPC193842
0.9404	High Similarity	NPC25495
0.9404	High Similarity	NPC253634
0.9404	High Similarity	NPC18607
0.9404	High Similarity	NPC9609
0.9404	High Similarity	NPC176300
0.9404	High Similarity	NPC4481
0.9404	High Similarity	NPC191459
0.9404	High Similarity	NPC152166
0.9404	High Similarity	NPC143828
0.9404	High Similarity	NPC288669
0.9404	High Similarity	NPC261004
0.9404	High Similarity	NPC19687
0.9404	High Similarity	NPC204854
0.9404	High Similarity	NPC115798
0.9404	High Similarity	NPC18772
0.9404	High Similarity	NPC130894
0.9404	High Similarity	NPC7846
0.9404	High Similarity	NPC300943
0.9404	High Similarity	NPC105242
0.9404	High Similarity	NPC22472
0.94	High Similarity	NPC235165
0.94	High Similarity	NPC68093
0.94	High Similarity	NPC292107
0.94	High Similarity	NPC474520
0.94	High Similarity	NPC191146
0.94	High Similarity	NPC138243
0.94	High Similarity	NPC265511
0.94	High Similarity	NPC255106
0.9396	High Similarity	NPC472915
0.9396	High Similarity	NPC280937
0.9396	High Similarity	NPC86485
0.9396	High Similarity	NPC124714
0.9392	High Similarity	NPC19980
0.9392	High Similarity	NPC125062
0.9392	High Similarity	NPC31363
0.9392	High Similarity	NPC252933

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 NPC45873 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	507
0.1-0.2	1069
0.2-0.3	2006
0.3-0.4	2680
0.4-0.5	1551
0.5-0.6	920
0.6-0.7	280
0.7-0.8	91
0.8-0.85	27
0.85-0.9	12
0.9-0.95	2
0.95-1	5

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.966	High Similarity	NPD2801	Approved
0.958	High Similarity	NPD1511	Approved
0.9448	High Similarity	NPD1512	Approved
0.92	High Similarity	NPD1934	Approved
0.902	High Similarity	NPD3882	Suspended
0.8889	High Similarity	NPD2393	Clinical (unspecified phase)
0.8868	High Similarity	NPD3818	Discontinued
0.8712	High Similarity	NPD4338	Clinical (unspecified phase)
0.871	High Similarity	NPD3817	Phase 2
0.863	High Similarity	NPD1510	Phase 2
0.8625	High Similarity	NPD6167	Clinical (unspecified phase)
0.8625	High Similarity	NPD6166	Phase 2
0.8625	High Similarity	NPD6168	Clinical (unspecified phase)
0.8611	High Similarity	NPD943	Approved
0.8581	High Similarity	NPD1549	Phase 2
0.858	High Similarity	NPD7054	Approved
0.8535	High Similarity	NPD4868	Clinical (unspecified phase)
0.8528	High Similarity	NPD7472	Approved
0.8526	High Similarity	NPD1465	Phase 2
0.8514	High Similarity	NPD1550	Clinical (unspecified phase)
0.8514	High Similarity	NPD1552	Clinical (unspecified phase)
0.8491	Intermediate Similarity	NPD5494	Approved
0.8487	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8452	Intermediate Similarity	NPD4380	Phase 2
0.8415	Intermediate Similarity	NPD7074	Phase 3
0.8365	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8364	Intermediate Similarity	NPD6797	Phase 2
0.8356	Intermediate Similarity	NPD1240	Approved
0.8354	Intermediate Similarity	NPD5402	Approved
0.8323	Intermediate Similarity	NPD1247	Approved
0.8313	Intermediate Similarity	NPD7251	Discontinued
0.8263	Intermediate Similarity	NPD7808	Phase 3
0.8247	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8243	Intermediate Similarity	NPD1607	Approved
0.8207	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.82	Intermediate Similarity	NPD2796	Approved
0.8182	Intermediate Similarity	NPD6799	Approved
0.8176	Intermediate Similarity	NPD447	Suspended
0.816	Intermediate Similarity	NPD6232	Discontinued
0.8138	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.8137	Intermediate Similarity	NPD7075	Discontinued
0.8133	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.8121	Intermediate Similarity	NPD7473	Discontinued
0.8105	Intermediate Similarity	NPD3750	Approved
0.8092	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8063	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8054	Intermediate Similarity	NPD230	Phase 1
0.8036	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8024	Intermediate Similarity	NPD5844	Phase 1
0.8	Intermediate Similarity	NPD6801	Discontinued
0.7987	Intermediate Similarity	NPD1613	Approved
0.7987	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7975	Intermediate Similarity	NPD919	Approved
0.7961	Intermediate Similarity	NPD1551	Phase 2
0.795	Intermediate Similarity	NPD7819	Suspended
0.7914	Intermediate Similarity	NPD3749	Approved
0.7911	Intermediate Similarity	NPD5403	Approved
0.7898	Intermediate Similarity	NPD5401	Approved
0.7892	Intermediate Similarity	NPD3926	Phase 2
0.7875	Intermediate Similarity	NPD6599	Discontinued
0.7862	Intermediate Similarity	NPD1653	Approved
0.7843	Intermediate Similarity	NPD2935	Discontinued
0.7826	Intermediate Similarity	NPD7411	Suspended
0.7811	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7806	Intermediate Similarity	NPD2800	Approved
0.7791	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD3748	Approved
0.777	Intermediate Similarity	NPD9494	Approved
0.7755	Intermediate Similarity	NPD1203	Approved
0.7733	Intermediate Similarity	NPD2313	Discontinued
0.7692	Intermediate Similarity	NPD1243	Approved
0.7688	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7688	Intermediate Similarity	NPD920	Approved
0.7677	Intermediate Similarity	NPD2344	Approved
0.7674	Intermediate Similarity	NPD6559	Discontinued
0.7673	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7671	Intermediate Similarity	NPD9269	Phase 2
0.7665	Intermediate Similarity	NPD6959	Discontinued
0.7662	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD3751	Discontinued
0.7643	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7595	Intermediate Similarity	NPD6190	Approved
0.7593	Intermediate Similarity	NPD3226	Approved
0.7582	Intermediate Similarity	NPD1933	Approved
0.7571	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.755	Intermediate Similarity	NPD3027	Phase 3
0.7547	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.753	Intermediate Similarity	NPD7768	Phase 2
0.7529	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD2309	Approved
0.7468	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7453	Intermediate Similarity	NPD2533	Approved
0.7453	Intermediate Similarity	NPD2534	Approved
0.7453	Intermediate Similarity	NPD2532	Approved
0.7452	Intermediate Similarity	NPD2346	Discontinued
0.7448	Intermediate Similarity	NPD1548	Phase 1
0.7436	Intermediate Similarity	NPD2799	Discontinued
0.7432	Intermediate Similarity	NPD9717	Approved
0.7421	Intermediate Similarity	NPD4628	Phase 3
0.7412	Intermediate Similarity	NPD3787	Discontinued
0.7397	Intermediate Similarity	NPD9268	Approved
0.7391	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD6099	Approved
0.7389	Intermediate Similarity	NPD6100	Approved
0.7365	Intermediate Similarity	NPD422	Phase 1
0.7365	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD7199	Phase 2
0.7337	Intermediate Similarity	NPD6234	Discontinued
0.7314	Intermediate Similarity	NPD5953	Discontinued
0.7303	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7299	Intermediate Similarity	NPD7286	Phase 2
0.7293	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7285	Intermediate Similarity	NPD1470	Approved
0.7273	Intermediate Similarity	NPD411	Approved
0.7273	Intermediate Similarity	NPD7685	Pre-registration
0.7267	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD1610	Phase 2
0.7246	Intermediate Similarity	NPD6844	Discontinued
0.7244	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7237	Intermediate Similarity	NPD2798	Approved
0.7232	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD3225	Approved
0.7215	Intermediate Similarity	NPD4308	Phase 3
0.7205	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD1608	Approved
0.72	Intermediate Similarity	NPD1481	Phase 2
0.7197	Intermediate Similarity	NPD6651	Approved
0.7178	Intermediate Similarity	NPD7390	Discontinued
0.7168	Intermediate Similarity	NPD5242	Approved
0.7161	Intermediate Similarity	NPD3268	Approved
0.716	Intermediate Similarity	NPD4288	Approved
0.7143	Intermediate Similarity	NPD37	Approved
0.7143	Intermediate Similarity	NPD6832	Phase 2
0.7133	Intermediate Similarity	NPD1535	Discovery
0.7133	Intermediate Similarity	NPD1201	Approved
0.7118	Intermediate Similarity	NPD4967	Phase 2
0.7118	Intermediate Similarity	NPD4965	Approved
0.7118	Intermediate Similarity	NPD4966	Approved
0.7095	Intermediate Similarity	NPD8312	Approved
0.7095	Intermediate Similarity	NPD8313	Approved
0.7083	Intermediate Similarity	NPD6386	Approved
0.7083	Intermediate Similarity	NPD6385	Approved
0.7073	Intermediate Similarity	NPD4357	Discontinued
0.7072	Intermediate Similarity	NPD8434	Phase 2
0.7059	Intermediate Similarity	NPD2797	Approved
0.7059	Intermediate Similarity	NPD5353	Approved
0.7051	Intermediate Similarity	NPD1296	Phase 2
0.7051	Intermediate Similarity	NPD3764	Approved
0.7045	Intermediate Similarity	NPD7228	Approved
0.7043	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD4908	Phase 1
0.7027	Intermediate Similarity	NPD5536	Phase 2
0.7021	Intermediate Similarity	NPD6782	Approved
0.7021	Intermediate Similarity	NPD6779	Approved
0.7021	Intermediate Similarity	NPD6781	Approved
0.7021	Intermediate Similarity	NPD6780	Approved
0.7021	Intermediate Similarity	NPD6778	Approved
0.7021	Intermediate Similarity	NPD6776	Approved
0.7021	Intermediate Similarity	NPD6777	Approved
0.7019	Intermediate Similarity	NPD1471	Phase 3
0.7006	Intermediate Similarity	NPD6233	Phase 2
0.7	Intermediate Similarity	NPD17	Approved
0.7	Intermediate Similarity	NPD7033	Discontinued
0.6995	Remote Similarity	NPD4287	Approved
0.698	Remote Similarity	NPD9545	Approved
0.6968	Remote Similarity	NPD2861	Phase 2
0.6968	Remote Similarity	NPD3018	Phase 2
0.6966	Remote Similarity	NPD228	Approved
0.6962	Remote Similarity	NPD1558	Phase 1
0.6962	Remote Similarity	NPD4307	Phase 2
0.6959	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD2296	Approved
0.6959	Remote Similarity	NPD9493	Approved
0.6951	Remote Similarity	NPD2354	Approved
0.6948	Remote Similarity	NPD3267	Approved
0.6948	Remote Similarity	NPD3266	Approved
0.6944	Remote Similarity	NPD7549	Discontinued
0.6943	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6935	Remote Similarity	NPD4363	Phase 3
0.6935	Remote Similarity	NPD2899	Discontinued
0.6935	Remote Similarity	NPD4360	Phase 2
0.6933	Remote Similarity	NPD1652	Phase 2
0.6933	Remote Similarity	NPD2654	Approved
0.6932	Remote Similarity	NPD2403	Approved
0.6928	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD5710	Approved
0.6914	Remote Similarity	NPD5711	Approved
0.6911	Remote Similarity	NPD7435	Discontinued
0.6903	Remote Similarity	NPD1019	Discontinued
0.6891	Remote Similarity	NPD7584	Approved
0.6886	Remote Similarity	NPD1940	Clinical (unspecified phase)
0.6885	Remote Similarity	NPD8150	Discontinued
0.6879	Remote Similarity	NPD4625	Phase 3
0.6871	Remote Similarity	NPD1241	Discontinued
0.6852	Remote Similarity	NPD5408	Approved
0.6852	Remote Similarity	NPD5405	Approved

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