NPASS Compound

Structure

NPC186507 OpenBabel07101718182D 25 27 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 7.7942 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 2.5000 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 5.1962 1.0000 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 6.0622 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 3.4641 -0.0000 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 4.3301 1.5000 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 1.7321 1.0000 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 1.7321 -0.0000 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 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 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 2.5000 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 2.5981 -0.5000 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 1 11 1 0 0 0 0 2 22 1 0 0 0 0 3 23 1 0 0 0 0 4 6 1 0 0 0 0 4 12 2 0 0 0 0 5 7 2 0 0 0 0 5 12 1 0 0 0 0 6 13 2 0 0 0 0 7 13 1 0 0 0 0 8 14 2 0 0 0 0 8 17 1 0 0 0 0 9 16 2 0 0 0 0 9 18 1 0 0 0 0 10 15 2 0 0 0 0 10 24 1 0 0 0 0 11 20 2 0 0 0 0 11 25 1 0 0 0 0 12 15 1 0 0 0 0 13 22 1 0 0 0 0 14 16 1 0 0 0 0 14 19 1 0 0 0 0 15 19 1 0 0 0 0 16 24 1 0 0 0 0 17 18 2 0 0 0 0 17 23 1 0 0 0 0 18 25 1 0 0 0 0 19 21 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	340.09
Volume:	340.524
LogP:	3.07
LogD:	2.609
LogS:	-4.534
# Rotatable Bonds:	5
TPSA:	74.97
# H-Bond Aceptor:	6
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.535
Synthetic Accessibility Score:	2.119
Fsp3:	0.158
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:	-4.738
MDCK Permeability:	5.0904491217806935e-05
Pgp-inhibitor:	0.828
Pgp-substrate:	0.011
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.006
30% Bioavailability (F30%):	0.163

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.279
Plasma Protein Binding (PPB):	85.67455291748047%
Volume Distribution (VD):	0.733
Pgp-substrate:	10.219378471374512%

ADMET: Metabolism

CYP1A2-inhibitor:	0.725
CYP1A2-substrate:	0.908
CYP2C19-inhibitor:	0.857
CYP2C19-substrate:	0.085
CYP2C9-inhibitor:	0.824
CYP2C9-substrate:	0.917
CYP2D6-inhibitor:	0.234
CYP2D6-substrate:	0.899
CYP3A4-inhibitor:	0.633
CYP3A4-substrate:	0.38

ADMET: Excretion

Clearance (CL):	2.821
Half-life (T1/2):	0.419

ADMET: Toxicity

hERG Blockers:	0.022
Human Hepatotoxicity (H-HT):	0.043
Drug-inuced Liver Injury (DILI):	0.865
AMES Toxicity:	0.209
Rat Oral Acute Toxicity:	0.37
Maximum Recommended Daily Dose:	0.259
Skin Sensitization:	0.769
Carcinogencity:	0.267
Eye Corrosion:	0.004
Eye Irritation:	0.225
Respiratory Toxicity:	0.375

Download Data

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

Natural Product: NPC186507

Natural Product ID:	NPC186507
*Common Name:**	Sid85272548
IUPAC Name:	[6-methoxy-3-(4-methoxyphenyl)-4-oxochromen-7-yl] acetate
Synonyms:	7-O-Acetylafromosin
Standard InCHIKey:	OLSFYFUZJCERJF-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C19H16O6/c1-11(20)25-18-9-16-14(8-17(18)23-3)19(21)15(10-24-16)12-4-6-13(22-2)7-5-12/h4-10H,1-3H3
SMILES:	COc1cc2c(cc1OC(=O)C)occ(c2=O)c1ccc(cc1)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL446567
PubChem CID:	3083840
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002506] Isoflavonoids [CHEMONTID:0002586] O-methylated isoflavonoids [CHEMONTID:0002606] 4'-O-methylated isoflavonoids [CHEMONTID:0002687] 4'-O-methylisoflavones

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO20912	Wisteria brachybotrys	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[2853205]
NPO20912	Wisteria brachybotrys	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	10
Potency	14

Activity Type	# Activity
Cell Line	5
Individual Protein	12
Others	7

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT165	Cell Line	HeLa	Homo sapiens	Inhibition	=	33.9	%	PMID[525779]
NPT80	Cell Line	Raji	Homo sapiens	Activity	=	100.0	%	PMID[525779]
NPT80	Cell Line	Raji	Homo sapiens	Activity	>	80.0	%	PMID[525779]
NPT80	Cell Line	Raji	Homo sapiens	Activity	=	80.0	%	PMID[525779]
NPT539	Individual Protein	Cellular tumor antigen p53	Homo sapiens	Potency	n.a.	50118.7	nM	PMID[525780]
NPT64	Individual Protein	ATPase family AAA domain-containing protein 5	Homo sapiens	Potency	n.a.	18348.9	nM	PMID[525780]
NPT64	Individual Protein	ATPase family AAA domain-containing protein 5	Homo sapiens	Potency	n.a.	12990.0	nM	PMID[525780]
NPT135	Individual Protein	Chromobox protein homolog 1	Homo sapiens	Potency	n.a.	70794.6	nM	PMID[525780]
NPT10	Individual Protein	Geminin	Homo sapiens	Potency	n.a.	819.9	nM	PMID[525780]
NPT1474	Individual Protein	ATP-dependent Clp protease proteolytic subunit	Bacillus subtilis (strain 168)	Potency	n.a.	17782.8	nM	PMID[525780]
NPT156	Individual Protein	Sphingomyelin phosphodiesterase	Homo sapiens	Potency	n.a.	15848.9	nM	PMID[525780]
NPT157	Individual Protein	Breast cancer type 1 susceptibility protein	Homo sapiens	Potency	n.a.	10000.0	nM	PMID[525780]
NPT160	Individual Protein	TAR DNA-binding protein 43	Homo sapiens	Potency	n.a.	35481.3	nM	PMID[525780]
NPT161	Individual Protein	Rap guanine nucleotide exchange factor 4	Homo sapiens	Potency	n.a.	50118.7	nM	PMID[525780]
NPT535	Individual Protein	Parathyroid hormone receptor	Homo sapiens	Potency	n.a.	79432.8	nM	PMID[525780]
NPT2	Others	Unspecified		Activity	=	2.1	%	PMID[525779]
NPT2	Others	Unspecified		Activity	=	72.7	%	PMID[525779]
NPT2	Others	Unspecified		Activity	=	42.3	%	PMID[525779]
NPT2	Others	Unspecified		Activity	=	6.0	%	PMID[525779]
NPT2	Others	Unspecified		Activity	=	0.0	%	PMID[525779]
NPT2	Others	Unspecified		Potency	n.a.	11220.2	nM	PMID[525780]
NPT861	Individual Protein	Isocitrate dehydrogenase [NADP] cytoplasmic	Homo sapiens	Potency	n.a.	44668.4	nM	PMID[525780]
NPT2	Others	Unspecified		Potency	n.a.	1995.3	nM	PMID[525780]

☑ 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 NPC186507 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	475
0.1-0.2	1967
0.2-0.3	4858
0.3-0.4	10805
0.4-0.5	6945
0.5-0.6	3878
0.6-0.7	5691
0.7-0.8	5011
0.8-0.85	1996
0.85-0.9	918
0.9-0.95	148
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.9595	High Similarity	NPC474663
0.9595	High Similarity	NPC198615
0.9589	High Similarity	NPC205522
0.9533	High Similarity	NPC122623
0.9533	High Similarity	NPC276059
0.9533	High Similarity	NPC34725
0.9533	High Similarity	NPC241774
0.9527	High Similarity	NPC29056
0.9524	High Similarity	NPC63256
0.9524	High Similarity	NPC10304
0.9521	High Similarity	NPC216314
0.9521	High Similarity	NPC110639
0.9521	High Similarity	NPC14958
0.9521	High Similarity	NPC215932
0.9521	High Similarity	NPC120924
0.9521	High Similarity	NPC40818
0.9521	High Similarity	NPC106461
0.9521	High Similarity	NPC195919
0.947	High Similarity	NPC257277
0.9459	High Similarity	NPC238366
0.9459	High Similarity	NPC474648
0.9456	High Similarity	NPC85233
0.9452	High Similarity	NPC136278
0.9452	High Similarity	NPC471590
0.9392	High Similarity	NPC183236
0.9388	High Similarity	NPC302408
0.9388	High Similarity	NPC283002
0.9388	High Similarity	NPC231013
0.9384	High Similarity	NPC182842
0.9384	High Similarity	NPC113089
0.9384	High Similarity	NPC23955
0.9342	High Similarity	NPC474983
0.9338	High Similarity	NPC280937
0.9338	High Similarity	NPC128961
0.9338	High Similarity	NPC472408
0.9333	High Similarity	NPC474388
0.9333	High Similarity	NPC472535
0.9333	High Similarity	NPC474170
0.9329	High Similarity	NPC69752
0.932	High Similarity	NPC165512
0.9315	High Similarity	NPC9966
0.9315	High Similarity	NPC70853
0.9281	High Similarity	NPC19097
0.9276	High Similarity	NPC471746
0.9272	High Similarity	NPC166201
0.9267	High Similarity	NPC259058
0.9267	High Similarity	NPC177839
0.9267	High Similarity	NPC201547
0.9252	High Similarity	NPC293201
0.9247	High Similarity	NPC185607
0.9247	High Similarity	NPC29536
0.9247	High Similarity	NPC214919
0.9247	High Similarity	NPC124467
0.9216	High Similarity	NPC180340
0.9211	High Similarity	NPC472915
0.9211	High Similarity	NPC478213
0.9205	High Similarity	NPC208043
0.9205	High Similarity	NPC308451
0.9205	High Similarity	NPC226973
0.9205	High Similarity	NPC262623
0.92	High Similarity	NPC181250
0.9195	High Similarity	NPC470511
0.9195	High Similarity	NPC299923
0.9178	High Similarity	NPC58229
0.9172	High Similarity	NPC475369
0.9172	High Similarity	NPC280893
0.9167	High Similarity	NPC108767
0.9161	High Similarity	NPC477164
0.9156	High Similarity	NPC476981
0.9156	High Similarity	NPC108456
0.9156	High Similarity	NPC181960
0.9156	High Similarity	NPC258644
0.915	High Similarity	NPC37392
0.915	High Similarity	NPC256612
0.915	High Similarity	NPC213622
0.915	High Similarity	NPC472909
0.915	High Similarity	NPC20830
0.9145	High Similarity	NPC68882
0.9145	High Similarity	NPC40033
0.9145	High Similarity	NPC148497
0.9145	High Similarity	NPC292460
0.9145	High Similarity	NPC134677
0.9145	High Similarity	NPC153008
0.9139	High Similarity	NPC239363
0.9139	High Similarity	NPC5840
0.9139	High Similarity	NPC189270
0.9139	High Similarity	NPC156953
0.9139	High Similarity	NPC306821
0.9133	High Similarity	NPC476342
0.9128	High Similarity	NPC310259
0.9114	High Similarity	NPC193881
0.9114	High Similarity	NPC210460
0.9114	High Similarity	NPC155264
0.9114	High Similarity	NPC67450
0.911	High Similarity	NPC136095
0.9103	High Similarity	NPC165549
0.9091	High Similarity	NPC472916
0.9091	High Similarity	NPC303255
0.9085	High Similarity	NPC160951
0.9085	High Similarity	NPC274327
0.9085	High Similarity	NPC183878
0.9085	High Similarity	NPC86485
0.9085	High Similarity	NPC145379
0.9085	High Similarity	NPC255350
0.9085	High Similarity	NPC22519
0.9085	High Similarity	NPC69394
0.9085	High Similarity	NPC124714
0.9085	High Similarity	NPC47781
0.9085	High Similarity	NPC57211
0.9085	High Similarity	NPC244371
0.9085	High Similarity	NPC231018
0.9085	High Similarity	NPC176775
0.9079	High Similarity	NPC117579
0.9079	High Similarity	NPC149614
0.9079	High Similarity	NPC279061
0.9073	High Similarity	NPC328119
0.906	High Similarity	NPC213482
0.9054	High Similarity	NPC476054
0.9045	High Similarity	NPC18284
0.9045	High Similarity	NPC273021
0.9038	High Similarity	NPC476980
0.9038	High Similarity	NPC298093
0.9032	High Similarity	NPC162869
0.9032	High Similarity	NPC470402
0.9032	High Similarity	NPC48208
0.9032	High Similarity	NPC210084
0.9032	High Similarity	NPC156057
0.9032	High Similarity	NPC472911
0.9032	High Similarity	NPC245758
0.9032	High Similarity	NPC99597
0.9032	High Similarity	NPC472910
0.9032	High Similarity	NPC96167
0.9032	High Similarity	NPC222814
0.9032	High Similarity	NPC474836
0.9032	High Similarity	NPC475267
0.9032	High Similarity	NPC472913
0.9032	High Similarity	NPC472914
0.9032	High Similarity	NPC474208
0.9026	High Similarity	NPC138360
0.9026	High Similarity	NPC128863
0.9026	High Similarity	NPC280339
0.9026	High Similarity	NPC50715
0.9026	High Similarity	NPC196439
0.9026	High Similarity	NPC255807
0.9026	High Similarity	NPC31018
0.9026	High Similarity	NPC2928
0.9026	High Similarity	NPC183597
0.9026	High Similarity	NPC208197
0.9026	High Similarity	NPC163780
0.9026	High Similarity	NPC167815
0.9026	High Similarity	NPC478238
0.9026	High Similarity	NPC4455
0.9026	High Similarity	NPC227325
0.9026	High Similarity	NPC2476
0.9026	High Similarity	NPC189960
0.9026	High Similarity	NPC201136
0.9026	High Similarity	NPC146165
0.9026	High Similarity	NPC92659
0.9026	High Similarity	NPC32557
0.902	High Similarity	NPC222830
0.902	High Similarity	NPC301323
0.902	High Similarity	NPC156222
0.902	High Similarity	NPC100971
0.902	High Similarity	NPC121522
0.902	High Similarity	NPC162313
0.902	High Similarity	NPC25270
0.902	High Similarity	NPC293183
0.902	High Similarity	NPC256283
0.902	High Similarity	NPC291802
0.902	High Similarity	NPC131266
0.902	High Similarity	NPC209487
0.902	High Similarity	NPC275836
0.902	High Similarity	NPC60972
0.902	High Similarity	NPC269451
0.902	High Similarity	NPC198826
0.902	High Similarity	NPC241498
0.902	High Similarity	NPC181209
0.902	High Similarity	NPC39732
0.902	High Similarity	NPC35763
0.902	High Similarity	NPC100887
0.902	High Similarity	NPC52623
0.902	High Similarity	NPC301123
0.902	High Similarity	NPC239128
0.902	High Similarity	NPC71334
0.902	High Similarity	NPC120163
0.902	High Similarity	NPC187498
0.902	High Similarity	NPC275722
0.902	High Similarity	NPC83508
0.902	High Similarity	NPC212678
0.902	High Similarity	NPC245382
0.902	High Similarity	NPC216769
0.902	High Similarity	NPC100263
0.902	High Similarity	NPC188203
0.902	High Similarity	NPC57030
0.902	High Similarity	NPC131624
0.9013	High Similarity	NPC179183
0.9007	High Similarity	NPC195202
0.9007	High Similarity	NPC261548
0.9	High Similarity	NPC280493
0.8987	High Similarity	NPC65846

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 NPC186507 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	417
0.1-0.2	1007
0.2-0.3	1852
0.3-0.4	2639
0.4-0.5	1814
0.5-0.6	904
0.6-0.7	359
0.7-0.8	103
0.8-0.85	44
0.85-0.9	10
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.915	High Similarity	NPD3817	Phase 2
0.9085	High Similarity	NPD2801	Approved
0.9038	High Similarity	NPD5494	Approved
0.8776	High Similarity	NPD2796	Approved
0.8774	High Similarity	NPD1934	Approved
0.8734	High Similarity	NPD919	Approved
0.8625	High Similarity	NPD1247	Approved
0.8618	High Similarity	NPD6799	Approved
0.8608	High Similarity	NPD3882	Suspended
0.8599	High Similarity	NPD2393	Clinical (unspecified phase)
0.8589	High Similarity	NPD3818	Discontinued
0.8554	High Similarity	NPD4338	Clinical (unspecified phase)
0.8544	High Similarity	NPD5402	Approved
0.8537	High Similarity	NPD5844	Phase 1
0.8497	Intermediate Similarity	NPD1511	Approved
0.8491	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8481	Intermediate Similarity	NPD7819	Suspended
0.8481	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8452	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.8452	Intermediate Similarity	NPD920	Approved
0.8418	Intermediate Similarity	NPD6801	Discontinued
0.8408	Intermediate Similarity	NPD6599	Discontinued
0.8387	Intermediate Similarity	NPD1512	Approved
0.8354	Intermediate Similarity	NPD6166	Phase 2
0.8354	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8354	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8344	Intermediate Similarity	NPD6232	Discontinued
0.8323	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.8323	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8323	Intermediate Similarity	NPD7075	Discontinued
0.8313	Intermediate Similarity	NPD7054	Approved
0.8303	Intermediate Similarity	NPD7473	Discontinued
0.8293	Intermediate Similarity	NPD3926	Phase 2
0.8263	Intermediate Similarity	NPD7074	Phase 3
0.8263	Intermediate Similarity	NPD7472	Approved
0.8239	Intermediate Similarity	NPD7411	Suspended
0.8235	Intermediate Similarity	NPD1243	Approved
0.8212	Intermediate Similarity	NPD1510	Phase 2
0.8212	Intermediate Similarity	NPD3748	Approved
0.821	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8194	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.8176	Intermediate Similarity	NPD4380	Phase 2
0.817	Intermediate Similarity	NPD1549	Phase 2
0.8137	Intermediate Similarity	NPD1465	Phase 2
0.8133	Intermediate Similarity	NPD1933	Approved
0.8133	Intermediate Similarity	NPD447	Suspended
0.8118	Intermediate Similarity	NPD7808	Phase 3
0.8107	Intermediate Similarity	NPD6797	Phase 2
0.8105	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8105	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8101	Intermediate Similarity	NPD5403	Approved
0.8089	Intermediate Similarity	NPD5401	Approved
0.8059	Intermediate Similarity	NPD7251	Discontinued
0.8041	Intermediate Similarity	NPD6832	Phase 2
0.8039	Intermediate Similarity	NPD2935	Discontinued
0.8013	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7975	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7964	Intermediate Similarity	NPD5242	Approved
0.7949	Intermediate Similarity	NPD3750	Approved
0.7947	Intermediate Similarity	NPD1240	Approved
0.7935	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7933	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7885	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7879	Intermediate Similarity	NPD3749	Approved
0.7843	Intermediate Similarity	NPD1607	Approved
0.7818	Intermediate Similarity	NPD7768	Phase 2
0.7815	Intermediate Similarity	NPD2313	Discontinued
0.7811	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7806	Intermediate Similarity	NPD1551	Phase 2
0.7791	Intermediate Similarity	NPD6385	Approved
0.7791	Intermediate Similarity	NPD6386	Approved
0.7778	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD3226	Approved
0.7778	Intermediate Similarity	NPD230	Phase 1
0.7758	Intermediate Similarity	NPD5353	Approved
0.7758	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.775	Intermediate Similarity	NPD2534	Approved
0.775	Intermediate Similarity	NPD2532	Approved
0.775	Intermediate Similarity	NPD2533	Approved
0.7746	Intermediate Similarity	NPD6559	Discontinued
0.7742	Intermediate Similarity	NPD2799	Discontinued
0.774	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7738	Intermediate Similarity	NPD7199	Phase 2
0.7722	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7722	Intermediate Similarity	NPD4628	Phase 3
0.7716	Intermediate Similarity	NPD1653	Approved
0.7712	Intermediate Similarity	NPD943	Approved
0.7688	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7643	Intermediate Similarity	NPD2346	Discontinued
0.7633	Intermediate Similarity	NPD6959	Discontinued
0.76	Intermediate Similarity	NPD3267	Approved
0.76	Intermediate Similarity	NPD3266	Approved
0.7597	Intermediate Similarity	NPD4307	Phase 2
0.7586	Intermediate Similarity	NPD5953	Discontinued
0.7572	Intermediate Similarity	NPD7286	Phase 2
0.7568	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.755	Intermediate Similarity	NPD1019	Discontinued
0.753	Intermediate Similarity	NPD37	Approved
0.75	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD4967	Phase 2
0.75	Intermediate Similarity	NPD4966	Approved
0.75	Intermediate Similarity	NPD4965	Approved
0.7485	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD1203	Approved
0.7468	Intermediate Similarity	NPD1296	Phase 2
0.7468	Intermediate Similarity	NPD3268	Approved
0.7459	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7453	Intermediate Similarity	NPD6190	Approved
0.7438	Intermediate Similarity	NPD2800	Approved
0.7434	Intermediate Similarity	NPD2798	Approved
0.7432	Intermediate Similarity	NPD17	Approved
0.7414	Intermediate Similarity	NPD3751	Discontinued
0.7412	Intermediate Similarity	NPD6234	Discontinued
0.7405	Intermediate Similarity	NPD7033	Discontinued
0.7405	Intermediate Similarity	NPD4308	Phase 3
0.7401	Intermediate Similarity	NPD7549	Discontinued
0.74	Intermediate Similarity	NPD9717	Approved
0.7384	Intermediate Similarity	NPD3787	Discontinued
0.7374	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7372	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7372	Intermediate Similarity	NPD1613	Approved
0.7368	Intermediate Similarity	NPD2797	Approved
0.7366	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD5536	Phase 2
0.7346	Intermediate Similarity	NPD3887	Approved
0.7338	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD8434	Phase 2
0.7321	Intermediate Similarity	NPD6844	Discontinued
0.7312	Intermediate Similarity	NPD2344	Approved
0.7308	Intermediate Similarity	NPD6233	Phase 2
0.7299	Intermediate Similarity	NPD2403	Approved
0.729	Intermediate Similarity	NPD3027	Phase 3
0.7285	Intermediate Similarity	NPD1608	Approved
0.7284	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD7229	Phase 3
0.7273	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7262	Intermediate Similarity	NPD5889	Approved
0.7262	Intermediate Similarity	NPD5890	Approved
0.7247	Intermediate Similarity	NPD7685	Pre-registration
0.7244	Intermediate Similarity	NPD411	Approved
0.7244	Intermediate Similarity	NPD6798	Discontinued
0.7235	Intermediate Similarity	NPD4288	Approved
0.7225	Intermediate Similarity	NPD8127	Discontinued
0.7222	Intermediate Similarity	NPD1652	Phase 2
0.7222	Intermediate Similarity	NPD2654	Approved
0.7219	Intermediate Similarity	NPD422	Phase 1
0.7216	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD3688	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD3146	Approved
0.7207	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7205	Intermediate Similarity	NPD2353	Approved
0.7205	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.7204	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7196	Intermediate Similarity	NPD5006	Approved
0.7196	Intermediate Similarity	NPD5005	Approved
0.7193	Intermediate Similarity	NPD5019	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD3225	Approved
0.7188	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7184	Intermediate Similarity	NPD5711	Approved
0.7184	Intermediate Similarity	NPD5710	Approved
0.7184	Intermediate Similarity	NPD6808	Phase 2
0.7171	Intermediate Similarity	NPD3972	Approved
0.7167	Intermediate Similarity	NPD8312	Approved
0.7167	Intermediate Similarity	NPD8313	Approved
0.7161	Intermediate Similarity	NPD3018	Phase 2
0.7161	Intermediate Similarity	NPD9494	Approved
0.716	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD7039	Approved
0.7151	Intermediate Similarity	NPD7038	Approved
0.7143	Intermediate Similarity	NPD6100	Approved
0.7143	Intermediate Similarity	NPD7458	Discontinued
0.7143	Intermediate Similarity	NPD6099	Approved
0.7134	Intermediate Similarity	NPD2309	Approved
0.7133	Intermediate Similarity	NPD9268	Approved
0.7128	Intermediate Similarity	NPD8285	Discontinued
0.7119	Intermediate Similarity	NPD7228	Approved
0.7115	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD6355	Discontinued
0.7107	Intermediate Similarity	NPD5124	Phase 1
0.7107	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD6585	Discontinued
0.7099	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD1471	Phase 3
0.7075	Intermediate Similarity	NPD1241	Discontinued
0.7074	Intermediate Similarity	NPD4420	Approved
0.7073	Intermediate Similarity	NPD4110	Phase 3
0.7073	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7068	Intermediate Similarity	NPD7435	Discontinued
0.7066	Intermediate Similarity	NPD6273	Approved
0.7066	Intermediate Similarity	NPD7314	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD6651	Approved
0.7059	Intermediate Similarity	NPD2981	Phase 2
0.7059	Intermediate Similarity	NPD9269	Phase 2
0.7052	Intermediate Similarity	NPD6971	Discontinued
0.7049	Intermediate Similarity	NPD8150	Discontinued
0.7041	Intermediate Similarity	NPD5808	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