NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	270.05
Volume:	265.186
LogP:	3.025
LogD:	2.535
LogS:	-3.705
# Rotatable Bonds:	1
TPSA:	90.9
# H-Bond Aceptor:	5
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.591
Synthetic Accessibility Score:	2.208
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:	-4.83
MDCK Permeability:	1.1910202374565415e-05
Pgp-inhibitor:	0.004
Pgp-substrate:	0.82
Human Intestinal Absorption (HIA):	0.018
20% Bioavailability (F20%):	0.995
30% Bioavailability (F30%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.012
Plasma Protein Binding (PPB):	97.08589935302734%
Volume Distribution (VD):	0.442
Pgp-substrate:	3.9019644260406494%

ADMET: Metabolism

CYP1A2-inhibitor:	0.969
CYP1A2-substrate:	0.135
CYP2C19-inhibitor:	0.321
CYP2C19-substrate:	0.052
CYP2C9-inhibitor:	0.414
CYP2C9-substrate:	0.854
CYP2D6-inhibitor:	0.606
CYP2D6-substrate:	0.812
CYP3A4-inhibitor:	0.749
CYP3A4-substrate:	0.168

ADMET: Excretion

Clearance (CL):	7.925
Half-life (T1/2):	0.851

ADMET: Toxicity

hERG Blockers:	0.04
Human Hepatotoxicity (H-HT):	0.086
Drug-inuced Liver Injury (DILI):	0.945
AMES Toxicity:	0.368
Rat Oral Acute Toxicity:	0.182
Maximum Recommended Daily Dose:	0.768
Skin Sensitization:	0.946
Carcinogencity:	0.355
Eye Corrosion:	0.005
Eye Irritation:	0.948
Respiratory Toxicity:	0.181

Download Data

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

Natural Product: NPC12367

Natural Product ID:	NPC12367
*Common Name:**	6,7-Dihydroxy-2-(4-Hydroxyphenyl)Chromen-4-One
IUPAC Name:	6,7-dihydroxy-2-(4-hydroxyphenyl)chromen-4-one
Synonyms:
Standard InCHIKey:	XADJWCRESPGUTB-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C15H10O5/c16-9-3-1-8(2-4-9)14-6-11(17)10-5-12(18)13(19)7-15(10)20-14/h1-7,16,18-19H
SMILES:	Oc1ccc(cc1)c1cc(=O)c2c(o1)cc(c(c2)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL475847
PubChem CID:	10355753
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]
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]
NPO4608	Aesculus californica	Species	Sapindaceae	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]
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]
NPO10680	Cistanche deserticola	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20354	Genista cadasonensis	Species	Fabaceae	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	3

Activity Type	# Activity
Individual Protein	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1196	Individual Protein	Low molecular weight phosphotyrosine protein phosphatase	Homo sapiens	Inhibition	=	25.0	%	PMID[448198]
NPT1196	Individual Protein	Low molecular weight phosphotyrosine protein phosphatase	Homo sapiens	Inhibition	=	10.0	%	PMID[448198]
NPT178	Individual Protein	Protein-tyrosine phosphatase 1B	Homo sapiens	Inhibition	=	10.0	%	PMID[448198]

☑ 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 NPC12367 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	566
0.1-0.2	2270
0.2-0.3	5840
0.3-0.4	11846
0.4-0.5	4567
0.5-0.6	4209
0.6-0.7	5137
0.7-0.8	4693
0.8-0.85	1929
0.85-0.9	1005
0.9-0.95	524
0.95-1	111

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC118726
0.9929	High Similarity	NPC239312
0.9929	High Similarity	NPC275772
0.9929	High Similarity	NPC130230
0.986	High Similarity	NPC45873
0.979	High Similarity	NPC216318
0.979	High Similarity	NPC17286
0.979	High Similarity	NPC195351
0.979	High Similarity	NPC259713
0.979	High Similarity	NPC296197
0.9787	High Similarity	NPC70136
0.9722	High Similarity	NPC77858
0.9722	High Similarity	NPC184136
0.972	High Similarity	NPC194856
0.972	High Similarity	NPC276930
0.9716	High Similarity	NPC279121
0.9655	High Similarity	NPC251110
0.9655	High Similarity	NPC225731
0.965	High Similarity	NPC168803
0.965	High Similarity	NPC207729
0.965	High Similarity	NPC74881
0.965	High Similarity	NPC51443
0.9645	High Similarity	NPC175013
0.9592	High Similarity	NPC20830
0.9592	High Similarity	NPC256612
0.9589	High Similarity	NPC162313
0.9589	High Similarity	NPC71334
0.9589	High Similarity	NPC156222
0.9589	High Similarity	NPC275836
0.9589	High Similarity	NPC120163
0.9589	High Similarity	NPC27208
0.9589	High Similarity	NPC83508
0.9589	High Similarity	NPC241498
0.9589	High Similarity	NPC198826
0.9589	High Similarity	NPC187498
0.9589	High Similarity	NPC57030
0.9589	High Similarity	NPC188203
0.9589	High Similarity	NPC301323
0.9589	High Similarity	NPC100887
0.9589	High Similarity	NPC212678
0.9589	High Similarity	NPC222830
0.9589	High Similarity	NPC131624
0.9589	High Similarity	NPC239128
0.9589	High Similarity	NPC256283
0.9589	High Similarity	NPC25270
0.9589	High Similarity	NPC293183
0.9589	High Similarity	NPC275722
0.9586	High Similarity	NPC61620
0.9586	High Similarity	NPC62042
0.9586	High Similarity	NPC248102
0.9583	High Similarity	NPC218490
0.958	High Similarity	NPC20791
0.958	High Similarity	NPC179271
0.9524	High Similarity	NPC69394
0.9524	High Similarity	NPC47781
0.9524	High Similarity	NPC183878
0.9524	High Similarity	NPC145379
0.9524	High Similarity	NPC22519
0.9524	High Similarity	NPC271779
0.9524	High Similarity	NPC160951
0.9524	High Similarity	NPC274327
0.9524	High Similarity	NPC167091
0.9524	High Similarity	NPC255350
0.9524	High Similarity	NPC206238
0.9524	High Similarity	NPC88645
0.9524	High Similarity	NPC292214
0.9524	High Similarity	NPC231018
0.9524	High Similarity	NPC176775
0.9521	High Similarity	NPC204515
0.9514	High Similarity	NPC108406
0.9459	High Similarity	NPC128863
0.9459	High Similarity	NPC44079
0.9459	High Similarity	NPC26227
0.9459	High Similarity	NPC163780
0.9459	High Similarity	NPC138360
0.9459	High Similarity	NPC167815
0.9459	High Similarity	NPC50715
0.9459	High Similarity	NPC227325
0.9459	High Similarity	NPC196439
0.9459	High Similarity	NPC2928
0.9459	High Similarity	NPC201136
0.9459	High Similarity	NPC4455
0.9459	High Similarity	NPC201451
0.9459	High Similarity	NPC208197
0.9459	High Similarity	NPC213622
0.9459	High Similarity	NPC146165
0.9459	High Similarity	NPC2476
0.9459	High Similarity	NPC92659
0.9459	High Similarity	NPC280339
0.9459	High Similarity	NPC183597
0.9459	High Similarity	NPC214138
0.9456	High Similarity	NPC180234
0.9456	High Similarity	NPC120537
0.9456	High Similarity	NPC101996
0.9456	High Similarity	NPC39732
0.9456	High Similarity	NPC39007
0.9456	High Similarity	NPC161277
0.9456	High Similarity	NPC142540
0.9456	High Similarity	NPC199100
0.9456	High Similarity	NPC60972
0.9452	High Similarity	NPC306821
0.9452	High Similarity	NPC10467
0.9448	High Similarity	NPC196277
0.9448	High Similarity	NPC43669
0.9448	High Similarity	NPC272721
0.9448	High Similarity	NPC119059
0.9444	High Similarity	NPC169749
0.9396	High Similarity	NPC98661
0.9396	High Similarity	NPC247017
0.9396	High Similarity	NPC245546
0.9396	High Similarity	NPC266960
0.9396	High Similarity	NPC43243
0.9396	High Similarity	NPC49824
0.9396	High Similarity	NPC472916
0.9392	High Similarity	NPC250822
0.9392	High Similarity	NPC276409
0.9392	High Similarity	NPC75279
0.9388	High Similarity	NPC202157
0.9388	High Similarity	NPC149614
0.9388	High Similarity	NPC226973
0.9388	High Similarity	NPC171010
0.9388	High Similarity	NPC260895
0.9388	High Similarity	NPC208043
0.9388	High Similarity	NPC308451
0.9384	High Similarity	NPC87125
0.9384	High Similarity	NPC287101
0.9384	High Similarity	NPC52005
0.9384	High Similarity	NPC1612
0.9384	High Similarity	NPC223579
0.9384	High Similarity	NPC270465
0.9384	High Similarity	NPC137062
0.9384	High Similarity	NPC183959
0.9384	High Similarity	NPC183950
0.9379	High Similarity	NPC61871
0.9379	High Similarity	NPC55557
0.9379	High Similarity	NPC30647
0.9379	High Similarity	NPC95864
0.9379	High Similarity	NPC77378
0.9371	High Similarity	NPC169479
0.9371	High Similarity	NPC159855
0.9338	High Similarity	NPC476980
0.9333	High Similarity	NPC189179
0.9333	High Similarity	NPC110070
0.9333	High Similarity	NPC287979
0.9333	High Similarity	NPC470402
0.9333	High Similarity	NPC163524
0.9333	High Similarity	NPC101830
0.9333	High Similarity	NPC75215
0.9333	High Similarity	NPC203891
0.9333	High Similarity	NPC176665
0.9333	High Similarity	NPC224137
0.9333	High Similarity	NPC99597
0.9333	High Similarity	NPC305663
0.9333	High Similarity	NPC227192
0.9333	High Similarity	NPC93376
0.9333	High Similarity	NPC210084
0.9329	High Similarity	NPC113906
0.9324	High Similarity	NPC100971
0.9324	High Similarity	NPC269451
0.9324	High Similarity	NPC100263
0.9324	High Similarity	NPC121522
0.9324	High Similarity	NPC216769
0.9324	High Similarity	NPC125300
0.9324	High Similarity	NPC249570
0.9324	High Similarity	NPC131266
0.9324	High Similarity	NPC209487
0.9324	High Similarity	NPC55205
0.9324	High Similarity	NPC35763
0.9324	High Similarity	NPC245382
0.9324	High Similarity	NPC301123
0.9324	High Similarity	NPC291802
0.9324	High Similarity	NPC181209
0.932	High Similarity	NPC29231
0.932	High Similarity	NPC286342
0.932	High Similarity	NPC149127
0.932	High Similarity	NPC188871
0.932	High Similarity	NPC88804
0.932	High Similarity	NPC179183
0.932	High Similarity	NPC3825
0.9315	High Similarity	NPC321011
0.9315	High Similarity	NPC294852
0.9315	High Similarity	NPC120464
0.9315	High Similarity	NPC19545
0.9315	High Similarity	NPC287395
0.9315	High Similarity	NPC183655
0.9315	High Similarity	NPC188679
0.9306	High Similarity	NPC242893
0.9306	High Similarity	NPC38065
0.9276	High Similarity	NPC258331
0.9276	High Similarity	NPC167678
0.9276	High Similarity	NPC29876
0.9276	High Similarity	NPC259456
0.9272	High Similarity	NPC25495
0.9272	High Similarity	NPC9609
0.9272	High Similarity	NPC19687
0.9272	High Similarity	NPC18607
0.9272	High Similarity	NPC143828
0.9272	High Similarity	NPC172770
0.9272	High Similarity	NPC4481
0.9272	High Similarity	NPC176300

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 NPC12367 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	498
0.1-0.2	1041
0.2-0.3	1900
0.3-0.4	2717
0.4-0.5	1632
0.5-0.6	917
0.6-0.7	297
0.7-0.8	96
0.8-0.85	35
0.85-0.9	12
0.9-0.95	1
0.95-1	4

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9716	High Similarity	NPD1511	Approved
0.958	High Similarity	NPD1512	Approved
0.9524	High Similarity	NPD2801	Approved
0.9067	High Similarity	NPD1934	Approved
0.9007	High Similarity	NPD2393	Clinical (unspecified phase)
0.8889	High Similarity	NPD3882	Suspended
0.875	High Similarity	NPD1510	Phase 2
0.8742	High Similarity	NPD3818	Discontinued
0.8732	High Similarity	NPD943	Approved
0.8699	High Similarity	NPD1549	Phase 2
0.863	High Similarity	NPD1550	Clinical (unspecified phase)
0.863	High Similarity	NPD1552	Clinical (unspecified phase)
0.86	High Similarity	NPD4378	Clinical (unspecified phase)
0.8589	High Similarity	NPD4338	Clinical (unspecified phase)
0.8581	High Similarity	NPD3817	Phase 2
0.8526	High Similarity	NPD4868	Clinical (unspecified phase)
0.85	High Similarity	NPD6166	Phase 2
0.85	High Similarity	NPD6168	Clinical (unspecified phase)
0.85	High Similarity	NPD6167	Clinical (unspecified phase)
0.8472	Intermediate Similarity	NPD1240	Approved
0.8457	Intermediate Similarity	NPD7054	Approved
0.8442	Intermediate Similarity	NPD4380	Phase 2
0.8405	Intermediate Similarity	NPD7472	Approved
0.8397	Intermediate Similarity	NPD1465	Phase 2
0.8365	Intermediate Similarity	NPD5494	Approved
0.8356	Intermediate Similarity	NPD1607	Approved
0.8355	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8354	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8354	Intermediate Similarity	NPD6797	Phase 2
0.8344	Intermediate Similarity	NPD5402	Approved
0.8311	Intermediate Similarity	NPD2796	Approved
0.8303	Intermediate Similarity	NPD7251	Discontinued
0.8293	Intermediate Similarity	NPD7074	Phase 3
0.8243	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.8212	Intermediate Similarity	NPD3750	Approved
0.82	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8199	Intermediate Similarity	NPD1247	Approved
0.8194	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.817	Intermediate Similarity	NPD6799	Approved
0.8163	Intermediate Similarity	NPD230	Phase 1
0.8144	Intermediate Similarity	NPD7808	Phase 3
0.8125	Intermediate Similarity	NPD7075	Discontinued
0.8125	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.8067	Intermediate Similarity	NPD1551	Phase 2
0.805	Intermediate Similarity	NPD7819	Suspended
0.805	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8041	Intermediate Similarity	NPD447	Suspended
0.8037	Intermediate Similarity	NPD6232	Discontinued
0.8024	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8012	Intermediate Similarity	NPD3749	Approved
0.8	Intermediate Similarity	NPD7473	Discontinued
0.7987	Intermediate Similarity	NPD6801	Discontinued
0.7973	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7973	Intermediate Similarity	NPD1613	Approved
0.7947	Intermediate Similarity	NPD2935	Discontinued
0.7925	Intermediate Similarity	NPD7411	Suspended
0.7908	Intermediate Similarity	NPD2800	Approved
0.7904	Intermediate Similarity	NPD5844	Phase 1
0.7898	Intermediate Similarity	NPD5403	Approved
0.7888	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7885	Intermediate Similarity	NPD5401	Approved
0.7881	Intermediate Similarity	NPD3748	Approved
0.7862	Intermediate Similarity	NPD6599	Discontinued
0.7862	Intermediate Similarity	NPD1203	Approved
0.7853	Intermediate Similarity	NPD919	Approved
0.7838	Intermediate Similarity	NPD2313	Discontinued
0.7798	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7792	Intermediate Similarity	NPD1243	Approved
0.7785	Intermediate Similarity	NPD920	Approved
0.7778	Intermediate Similarity	NPD9269	Phase 2
0.7778	Intermediate Similarity	NPD2344	Approved
0.7771	Intermediate Similarity	NPD3926	Phase 2
0.7771	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7763	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7758	Intermediate Similarity	NPD6959	Discontinued
0.7742	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7736	Intermediate Similarity	NPD1653	Approved
0.7688	Intermediate Similarity	NPD3226	Approved
0.7661	Intermediate Similarity	NPD6559	Discontinued
0.7643	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7635	Intermediate Similarity	NPD9494	Approved
0.7633	Intermediate Similarity	NPD3751	Discontinued
0.7622	Intermediate Similarity	NPD7768	Phase 2
0.7619	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.758	Intermediate Similarity	NPD2309	Approved
0.758	Intermediate Similarity	NPD6190	Approved
0.7564	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7562	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7552	Intermediate Similarity	NPD1548	Phase 1
0.7548	Intermediate Similarity	NPD2346	Discontinued
0.7547	Intermediate Similarity	NPD2534	Approved
0.7547	Intermediate Similarity	NPD2532	Approved
0.7547	Intermediate Similarity	NPD2533	Approved
0.7534	Intermediate Similarity	NPD9717	Approved
0.7532	Intermediate Similarity	NPD2799	Discontinued
0.75	Intermediate Similarity	NPD9268	Approved
0.7484	Intermediate Similarity	NPD6100	Approved
0.7484	Intermediate Similarity	NPD6099	Approved
0.7466	Intermediate Similarity	NPD422	Phase 1
0.7466	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7458	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7451	Intermediate Similarity	NPD1933	Approved
0.7417	Intermediate Similarity	NPD3027	Phase 3
0.7405	Intermediate Similarity	NPD4628	Phase 3
0.7399	Intermediate Similarity	NPD5953	Discontinued
0.7396	Intermediate Similarity	NPD3787	Discontinued
0.7384	Intermediate Similarity	NPD7286	Phase 2
0.7383	Intermediate Similarity	NPD1470	Approved
0.7368	Intermediate Similarity	NPD411	Approved
0.7365	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD1610	Phase 2
0.7338	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD6844	Discontinued
0.7333	Intermediate Similarity	NPD2798	Approved
0.7315	Intermediate Similarity	NPD3225	Approved
0.7314	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD4308	Phase 3
0.7297	Intermediate Similarity	NPD1481	Phase 2
0.7297	Intermediate Similarity	NPD1608	Approved
0.7296	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD6651	Approved
0.7283	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD7390	Discontinued
0.7267	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD3268	Approved
0.7246	Intermediate Similarity	NPD4288	Approved
0.7237	Intermediate Similarity	NPD6832	Phase 2
0.7235	Intermediate Similarity	NPD7199	Phase 2
0.723	Intermediate Similarity	NPD1201	Approved
0.723	Intermediate Similarity	NPD1535	Discovery
0.7219	Intermediate Similarity	NPD6234	Discontinued
0.7191	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7159	Intermediate Similarity	NPD7685	Pre-registration
0.7152	Intermediate Similarity	NPD2797	Approved
0.7151	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD1296	Phase 2
0.7143	Intermediate Similarity	NPD3764	Approved
0.7124	Intermediate Similarity	NPD4908	Phase 1
0.7107	Intermediate Similarity	NPD1471	Phase 3
0.7095	Intermediate Similarity	NPD17	Approved
0.7089	Intermediate Similarity	NPD7033	Discontinued
0.7079	Intermediate Similarity	NPD8312	Approved
0.7079	Intermediate Similarity	NPD8313	Approved
0.7075	Intermediate Similarity	NPD9545	Approved
0.7072	Intermediate Similarity	NPD4287	Approved
0.7059	Intermediate Similarity	NPD2861	Phase 2
0.7056	Intermediate Similarity	NPD8434	Phase 2
0.7055	Intermediate Similarity	NPD9493	Approved
0.7055	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7052	Intermediate Similarity	NPD5242	Approved
0.7051	Intermediate Similarity	NPD4307	Phase 2
0.7041	Intermediate Similarity	NPD2296	Approved
0.7039	Intermediate Similarity	NPD3266	Approved
0.7039	Intermediate Similarity	NPD3267	Approved
0.7032	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD37	Approved
0.7019	Intermediate Similarity	NPD2654	Approved
0.7012	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7012	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD4363	Phase 3
0.7011	Intermediate Similarity	NPD4360	Phase 2
0.7005	Intermediate Similarity	NPD6777	Approved
0.7005	Intermediate Similarity	NPD6779	Approved
0.7005	Intermediate Similarity	NPD6778	Approved
0.7005	Intermediate Similarity	NPD6776	Approved
0.7005	Intermediate Similarity	NPD6781	Approved
0.7005	Intermediate Similarity	NPD6782	Approved
0.7005	Intermediate Similarity	NPD6780	Approved
0.7	Intermediate Similarity	NPD4967	Phase 2
0.7	Intermediate Similarity	NPD4965	Approved
0.7	Intermediate Similarity	NPD4966	Approved
0.6994	Remote Similarity	NPD5710	Approved
0.6994	Remote Similarity	NPD5711	Approved
0.6993	Remote Similarity	NPD1019	Discontinued
0.6987	Remote Similarity	NPD6233	Phase 2
0.6968	Remote Similarity	NPD4625	Phase 3
0.6966	Remote Similarity	NPD1241	Discontinued
0.6964	Remote Similarity	NPD6386	Approved
0.6964	Remote Similarity	NPD6385	Approved
0.6951	Remote Similarity	NPD4357	Discontinued
0.6941	Remote Similarity	NPD5353	Approved
0.6937	Remote Similarity	NPD5408	Approved
0.6937	Remote Similarity	NPD5405	Approved
0.6937	Remote Similarity	NPD5404	Approved
0.6937	Remote Similarity	NPD5406	Approved
0.6933	Remote Similarity	NPD2354	Approved
0.6932	Remote Similarity	NPD7228	Approved
0.6928	Remote Similarity	NPD1164	Approved
0.6914	Remote Similarity	NPD2403	Approved
0.6914	Remote Similarity	NPD1652	Phase 2
0.6908	Remote Similarity	NPD4749	Approved
0.6897	Remote Similarity	NPD7229	Phase 3
0.6895	Remote Similarity	NPD7435	Discontinued
0.6892	Remote Similarity	NPD5536	Phase 2
0.6882	Remote Similarity	NPD4362	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD4361	Phase 2
0.6875	Remote Similarity	NPD7584	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