NPASS Compound

Structure

NPC476289 OpenBabel07101719152D 29 31 0 0 0 0 0 0 0 0999 V2000 9.1603 -7.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.4282 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5622 -5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.2942 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.4282 -6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0981 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5622 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.2942 -5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9641 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2321 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0981 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8301 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6962 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6962 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0981 -1.5000 0.0000 O 0 5 0 0 0 0 0 0 0 0 0 0 4.8301 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.5622 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.5622 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.5622 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 9.1603 -6.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3660 -4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3660 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.8301 -4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.5622 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.5622 -1.5000 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 1 24 1 0 0 0 0 2 25 1 0 0 0 0 3 26 1 0 0 0 0 4 6 1 0 0 0 0 4 9 2 0 0 0 0 5 7 2 0 0 0 0 5 9 1 0 0 0 0 6 10 2 0 0 0 0 7 10 1 0 0 0 0 8 11 2 0 0 0 0 8 12 1 0 0 0 0 9 16 1 0 0 0 0 10 24 1 0 0 0 0 11 13 1 0 0 0 0 11 27 1 0 0 0 0 12 17 2 0 0 0 0 12 25 1 0 0 0 0 13 14 2 0 0 0 0 13 15 1 0 0 0 0 14 17 1 0 0 0 0 14 19 1 0 0 0 0 15 18 1 0 0 0 0 15 20 2 0 0 0 0 16 18 2 0 0 0 0 16 27 1 0 0 0 0 17 26 1 0 0 0 0 18 28 1 0 0 0 0 21 29 1 0 0 0 0 22 29 2 0 0 0 0 23 29 2 0 0 0 0 28 29 1 0 0 0 0 M CHG 1 19 -1 M END $$$$

Physi-Chem Properties

Molecular Weight:	423.04
Volume:	378.216
LogP:	1.957
LogD:	0.85
LogS:	-3.649
# Rotatable Bonds:	6
TPSA:	144.56
# H-Bond Aceptor:	10
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	11

MedChem Properties

QED Drug-Likeness Score:	0.462
Synthetic Accessibility Score:	2.787
Fsp3:	0.167
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.625
MDCK Permeability:	1.4085035218158737e-05
Pgp-inhibitor:	1.0
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.052
20% Bioavailability (F20%):	0.001
30% Bioavailability (F30%):	0.002

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.001
Plasma Protein Binding (PPB):	97.73480987548828%
Volume Distribution (VD):	0.392
Pgp-substrate:	3.643449068069458%

ADMET: Metabolism

CYP1A2-inhibitor:	0.524
CYP1A2-substrate:	0.968
CYP2C19-inhibitor:	0.2
CYP2C19-substrate:	0.54
CYP2C9-inhibitor:	0.628
CYP2C9-substrate:	0.896
CYP2D6-inhibitor:	0.136
CYP2D6-substrate:	0.558
CYP3A4-inhibitor:	0.281
CYP3A4-substrate:	0.238

ADMET: Excretion

Clearance (CL):	1.286
Half-life (T1/2):	0.247

ADMET: Toxicity

hERG Blockers:	0.008
Human Hepatotoxicity (H-HT):	0.917
Drug-inuced Liver Injury (DILI):	0.982
AMES Toxicity:	0.269
Rat Oral Acute Toxicity:	0.682
Maximum Recommended Daily Dose:	0.654
Skin Sensitization:	0.478
Carcinogencity:	0.8
Eye Corrosion:	0.003
Eye Irritation:	0.242
Respiratory Toxicity:	0.406

Download Data

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

Natural Product: NPC476289

Natural Product ID:	NPC476289
*Common Name:**	Potassium Mikanin 3-Sulfate
IUPAC Name:	potassium;[5-hydroxy-6,7-dimethoxy-2-(4-methoxyphenyl)-4-oxochromen-3-yl] sulfate
Synonyms:	Potassium Mikanin 3-Sulfate
Standard InCHIKey:	AHPVNBWPHPZHCI-UHFFFAOYSA-M
Standard InCHI:	InChI=1S/C18H16O10S.K/c1-24-10-6-4-9(5-7-10)16-18(28-29(21,22)23)15(20)13-11(27-16)8-12(25-2)17(26-3)14(13)19;/h4-8,19H,1-3H3,(H,21,22,23);/q;+1/p-1
SMILES:	COc1ccc(cc1)c1oc2cc(OC)c(c(c2c(=O)c1OS(=O)(=O)O)[O-])OC.[K+]
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL562303
PubChem CID:	45267919
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
NPO24708	Mikania micrantha	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19267453]
NPO24708	Mikania micrantha	Species	Asteraceae	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	3
Others	5

Activity Type	# Activity
Cell Line	1
Organism	3
Others	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT616	Cell Line	MDCK	Canis lupus familiaris	TC50	=	236.8	uM	PMID[475859]
NPT70	Organism	Respiratory syncytial virus	Respiratory syncytial virus	IC50	=	79000.0	nM	PMID[475859]
NPT27	Others	Unspecified		TC50	=	471.9	uM	PMID[475859]
NPT27	Others	Unspecified		TI	=	6.0	n.a.	PMID[475859]
NPT336	Organism	Human parainfluenza virus 3	Human parainfluenza virus 3	IC50	=	19700.0	nM	PMID[475859]
NPT27	Others	Unspecified		TI	=	24.0	n.a.	PMID[475859]
NPT742	Organism	Influenza A virus	Influenza A virus	IC50	=	79000.0	nM	PMID[475859]
NPT27	Others	Unspecified		TI	=	3.0	n.a.	PMID[475859]

☑ 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 NPC476289 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	562
0.1-0.2	2271
0.2-0.3	6000
0.3-0.4	11934
0.4-0.5	4758
0.5-0.6	4597
0.6-0.7	5883
0.7-0.8	4515
0.8-0.85	1387
0.85-0.9	562
0.9-0.95	227
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.953	High Similarity	NPC134677
0.9527	High Similarity	NPC259058
0.9527	High Similarity	NPC201547
0.9459	High Similarity	NPC69752
0.9459	High Similarity	NPC181250
0.9456	High Similarity	NPC85233
0.9408	High Similarity	NPC174908
0.94	High Similarity	NPC301123
0.9388	High Similarity	NPC302408
0.9388	High Similarity	NPC283002
0.9388	High Similarity	NPC14958
0.9388	High Similarity	NPC106461
0.9388	High Similarity	NPC110639
0.9388	High Similarity	NPC215932
0.9388	High Similarity	NPC40818
0.9342	High Similarity	NPC98661
0.9342	High Similarity	NPC247017
0.9342	High Similarity	NPC178854
0.9338	High Similarity	NPC86485
0.9324	High Similarity	NPC205522
0.932	High Similarity	NPC165512
0.9281	High Similarity	NPC305663
0.9281	High Similarity	NPC176665
0.9281	High Similarity	NPC224137
0.9281	High Similarity	NPC93376
0.9281	High Similarity	NPC287979
0.9281	High Similarity	NPC75215
0.9281	High Similarity	NPC189179
0.9281	High Similarity	NPC163524
0.9281	High Similarity	NPC227192
0.9276	High Similarity	NPC241774
0.9276	High Similarity	NPC32557
0.9276	High Similarity	NPC34725
0.9276	High Similarity	NPC189960
0.9276	High Similarity	NPC26227
0.9276	High Similarity	NPC276059
0.9276	High Similarity	NPC122623
0.9276	High Similarity	NPC201451
0.9276	High Similarity	NPC44079
0.9267	High Similarity	NPC306821
0.9262	High Similarity	NPC261548
0.9257	High Similarity	NPC310259
0.9252	High Similarity	NPC23955
0.9221	High Similarity	NPC22472
0.9221	High Similarity	NPC19687
0.9221	High Similarity	NPC288669
0.9221	High Similarity	NPC204854
0.9221	High Similarity	NPC130894
0.9221	High Similarity	NPC115798
0.9221	High Similarity	NPC7846
0.9221	High Similarity	NPC18772
0.9221	High Similarity	NPC300943
0.9221	High Similarity	NPC152166
0.9221	High Similarity	NPC143828
0.9221	High Similarity	NPC191459
0.9221	High Similarity	NPC105242
0.9221	High Similarity	NPC9609
0.9221	High Similarity	NPC25495
0.9221	High Similarity	NPC261004
0.9221	High Similarity	NPC176300
0.9221	High Similarity	NPC253634
0.9221	High Similarity	NPC18607
0.9221	High Similarity	NPC4481
0.9216	High Similarity	NPC474520
0.9216	High Similarity	NPC257277
0.9216	High Similarity	NPC245546
0.9216	High Similarity	NPC43243
0.9216	High Similarity	NPC266960
0.9216	High Similarity	NPC49824
0.9211	High Similarity	NPC246204
0.9205	High Similarity	NPC208043
0.9205	High Similarity	NPC226973
0.92	High Similarity	NPC159103
0.9195	High Similarity	NPC299923
0.9189	High Similarity	NPC136278
0.9184	High Similarity	NPC9966
0.9184	High Similarity	NPC70853
0.9156	High Similarity	NPC7973
0.9156	High Similarity	NPC203891
0.9156	High Similarity	NPC101830
0.9156	High Similarity	NPC110070
0.9156	High Similarity	NPC29841
0.9156	High Similarity	NPC78302
0.9156	High Similarity	NPC472438
0.9156	High Similarity	NPC235215
0.915	High Similarity	NPC163780
0.915	High Similarity	NPC2476
0.915	High Similarity	NPC92659
0.915	High Similarity	NPC128863
0.915	High Similarity	NPC138360
0.915	High Similarity	NPC201136
0.915	High Similarity	NPC214138
0.915	High Similarity	NPC183597
0.915	High Similarity	NPC167815
0.915	High Similarity	NPC50715
0.915	High Similarity	NPC196439
0.915	High Similarity	NPC227325
0.915	High Similarity	NPC146165
0.915	High Similarity	NPC4455
0.915	High Similarity	NPC280339
0.9145	High Similarity	NPC198826
0.9145	High Similarity	NPC275722
0.9145	High Similarity	NPC120163
0.9145	High Similarity	NPC212678
0.9145	High Similarity	NPC222830
0.9145	High Similarity	NPC188203
0.9145	High Similarity	NPC131624
0.9145	High Similarity	NPC100887
0.9145	High Similarity	NPC256283
0.9145	High Similarity	NPC25270
0.9145	High Similarity	NPC57030
0.9145	High Similarity	NPC83508
0.9145	High Similarity	NPC27208
0.9145	High Similarity	NPC71334
0.9145	High Similarity	NPC239128
0.9145	High Similarity	NPC293183
0.9145	High Similarity	NPC187498
0.9145	High Similarity	NPC142540
0.9145	High Similarity	NPC162313
0.9145	High Similarity	NPC241498
0.9145	High Similarity	NPC156222
0.9145	High Similarity	NPC275836
0.9145	High Similarity	NPC301323
0.9139	High Similarity	NPC50728
0.9139	High Similarity	NPC219330
0.9139	High Similarity	NPC166753
0.9133	High Similarity	NPC10304
0.9133	High Similarity	NPC63256
0.9128	High Similarity	NPC231013
0.9122	High Similarity	NPC113089
0.9116	High Similarity	NPC214919
0.9116	High Similarity	NPC124467
0.9116	High Similarity	NPC29536
0.9097	High Similarity	NPC104459
0.9097	High Similarity	NPC193842
0.9097	High Similarity	NPC257914
0.9097	High Similarity	NPC238405
0.9091	High Similarity	NPC100916
0.9091	High Similarity	NPC55619
0.9091	High Similarity	NPC292107
0.9091	High Similarity	NPC303255
0.9091	High Similarity	NPC200388
0.9091	High Similarity	NPC268161
0.9085	High Similarity	NPC250822
0.9085	High Similarity	NPC75279
0.9085	High Similarity	NPC160951
0.9085	High Similarity	NPC274327
0.9085	High Similarity	NPC255350
0.9085	High Similarity	NPC183878
0.9085	High Similarity	NPC69394
0.9085	High Similarity	NPC231018
0.9085	High Similarity	NPC47781
0.9085	High Similarity	NPC276409
0.9085	High Similarity	NPC145379
0.9085	High Similarity	NPC22519
0.9085	High Similarity	NPC176775
0.9079	High Similarity	NPC472535
0.9079	High Similarity	NPC252933
0.9079	High Similarity	NPC474388
0.9079	High Similarity	NPC50403
0.9079	High Similarity	NPC76376
0.9079	High Similarity	NPC225731
0.9079	High Similarity	NPC133953
0.9079	High Similarity	NPC474170
0.9079	High Similarity	NPC117579
0.9079	High Similarity	NPC125062
0.9079	High Similarity	NPC200740
0.9079	High Similarity	NPC54394
0.9079	High Similarity	NPC236769
0.9079	High Similarity	NPC28274
0.9079	High Similarity	NPC308451
0.9073	High Similarity	NPC238366
0.9073	High Similarity	NPC328119
0.9067	High Similarity	NPC12200
0.9038	High Similarity	NPC131557
0.9026	High Similarity	NPC256612
0.9026	High Similarity	NPC20830
0.9026	High Similarity	NPC208197
0.9026	High Similarity	NPC213622
0.902	High Similarity	NPC55205
0.902	High Similarity	NPC292460
0.902	High Similarity	NPC279989
0.902	High Similarity	NPC123886
0.902	High Similarity	NPC82325
0.9013	High Similarity	NPC77858
0.9013	High Similarity	NPC177839
0.9013	High Similarity	NPC184136
0.9007	High Similarity	NPC195202
0.9	High Similarity	NPC120924
0.9	High Similarity	NPC195919
0.9	High Similarity	NPC216314
0.8974	High Similarity	NPC152904
0.8968	High Similarity	NPC265511
0.8961	High Similarity	NPC280937
0.8961	High Similarity	NPC179126
0.8961	High Similarity	NPC270620
0.8961	High Similarity	NPC472915
0.8961	High Similarity	NPC472408
0.8961	High Similarity	NPC162351
0.8961	High Similarity	NPC236223

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 NPC476289 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	477
0.1-0.2	1031
0.2-0.3	1964
0.3-0.4	2774
0.4-0.5	1648
0.5-0.6	866
0.6-0.7	271
0.7-0.8	94
0.8-0.85	16
0.85-0.9	8
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9085	High Similarity	NPD2801	Approved
0.9026	High Similarity	NPD3817	Phase 2
0.875	High Similarity	NPD1512	Approved
0.8654	High Similarity	NPD1934	Approved
0.8618	High Similarity	NPD1511	Approved
0.8608	High Similarity	NPD3882	Suspended
0.8562	High Similarity	NPD5494	Approved
0.8509	High Similarity	NPD1247	Approved
0.8466	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8466	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8466	Intermediate Similarity	NPD6166	Phase 2
0.8443	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8442	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8365	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8313	Intermediate Similarity	NPD5402	Approved
0.8293	Intermediate Similarity	NPD3926	Phase 2
0.8278	Intermediate Similarity	NPD2796	Approved
0.8258	Intermediate Similarity	NPD6799	Approved
0.8253	Intermediate Similarity	NPD3818	Discontinued
0.8225	Intermediate Similarity	NPD7808	Phase 3
0.8214	Intermediate Similarity	NPD6797	Phase 2
0.8204	Intermediate Similarity	NPD7054	Approved
0.8166	Intermediate Similarity	NPD7251	Discontinued
0.816	Intermediate Similarity	NPD919	Approved
0.8155	Intermediate Similarity	NPD7472	Approved
0.8075	Intermediate Similarity	NPD6801	Discontinued
0.8047	Intermediate Similarity	NPD7074	Phase 3
0.8025	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8012	Intermediate Similarity	NPD6232	Discontinued
0.7988	Intermediate Similarity	NPD7075	Discontinued
0.7987	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7987	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7976	Intermediate Similarity	NPD7473	Discontinued
0.7975	Intermediate Similarity	NPD5401	Approved
0.7974	Intermediate Similarity	NPD1510	Phase 2
0.795	Intermediate Similarity	NPD4380	Phase 2
0.795	Intermediate Similarity	NPD6599	Discontinued
0.7935	Intermediate Similarity	NPD1549	Phase 2
0.7927	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7914	Intermediate Similarity	NPD7819	Suspended
0.7879	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7875	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7875	Intermediate Similarity	NPD5403	Approved
0.7862	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7829	Intermediate Similarity	NPD1240	Approved
0.7778	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD5844	Phase 1
0.7727	Intermediate Similarity	NPD1607	Approved
0.7707	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD1465	Phase 2
0.7688	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7683	Intermediate Similarity	NPD7411	Suspended
0.7662	Intermediate Similarity	NPD1933	Approved
0.7662	Intermediate Similarity	NPD447	Suspended
0.7654	Intermediate Similarity	NPD920	Approved
0.7651	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7628	Intermediate Similarity	NPD3748	Approved
0.7597	Intermediate Similarity	NPD943	Approved
0.7547	Intermediate Similarity	NPD1243	Approved
0.7531	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7529	Intermediate Similarity	NPD6959	Discontinued
0.75	Intermediate Similarity	NPD3750	Approved
0.7468	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD2935	Discontinued
0.7442	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7438	Intermediate Similarity	NPD2800	Approved
0.7414	Intermediate Similarity	NPD3751	Discontinued
0.7407	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7384	Intermediate Similarity	NPD3787	Discontinued
0.7358	Intermediate Similarity	NPD1551	Phase 2
0.7355	Intermediate Similarity	NPD2313	Discontinued
0.7353	Intermediate Similarity	NPD3749	Approved
0.7349	Intermediate Similarity	NPD3226	Approved
0.7345	Intermediate Similarity	NPD6559	Discontinued
0.7338	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD6832	Phase 2
0.7326	Intermediate Similarity	NPD7199	Phase 2
0.7325	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7325	Intermediate Similarity	NPD230	Phase 1
0.7299	Intermediate Similarity	NPD2403	Approved
0.7299	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7288	Intermediate Similarity	NPD5953	Discontinued
0.7284	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD3018	Phase 2
0.7273	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7261	Intermediate Similarity	NPD1613	Approved
0.7261	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7256	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD1296	Phase 2
0.7241	Intermediate Similarity	NPD5242	Approved
0.7239	Intermediate Similarity	NPD6190	Approved
0.7222	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD2533	Approved
0.7212	Intermediate Similarity	NPD2532	Approved
0.7212	Intermediate Similarity	NPD2534	Approved
0.7205	Intermediate Similarity	NPD2344	Approved
0.7205	Intermediate Similarity	NPD2346	Discontinued
0.72	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD7768	Phase 2
0.7188	Intermediate Similarity	NPD2799	Discontinued
0.7186	Intermediate Similarity	NPD1653	Approved
0.7181	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7174	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD6386	Approved
0.716	Intermediate Similarity	NPD6385	Approved
0.7158	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD5353	Approved
0.7124	Intermediate Similarity	NPD2983	Phase 2
0.7124	Intermediate Similarity	NPD2982	Phase 2
0.7118	Intermediate Similarity	NPD6844	Discontinued
0.7118	Intermediate Similarity	NPD37	Approved
0.7117	Intermediate Similarity	NPD2654	Approved
0.7114	Intermediate Similarity	NPD5536	Phase 2
0.7099	Intermediate Similarity	NPD1471	Phase 3
0.7097	Intermediate Similarity	NPD2798	Approved
0.7093	Intermediate Similarity	NPD4966	Approved
0.7093	Intermediate Similarity	NPD4965	Approved
0.7093	Intermediate Similarity	NPD4967	Phase 2
0.7089	Intermediate Similarity	NPD6233	Phase 2
0.7088	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7079	Intermediate Similarity	NPD7286	Phase 2
0.7073	Intermediate Similarity	NPD4628	Phase 3
0.707	Intermediate Similarity	NPD3027	Phase 3
0.7066	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD6651	Approved
0.7059	Intermediate Similarity	NPD2981	Phase 2
0.7051	Intermediate Similarity	NPD9494	Approved
0.7049	Intermediate Similarity	NPD8434	Phase 2
0.7037	Intermediate Similarity	NPD6099	Approved
0.7037	Intermediate Similarity	NPD6100	Approved
0.7032	Intermediate Similarity	NPD3266	Approved
0.7032	Intermediate Similarity	NPD3267	Approved
0.7032	Intermediate Similarity	NPD1203	Approved
0.703	Intermediate Similarity	NPD2309	Approved
0.7021	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7017	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD6234	Discontinued
0.7006	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD3540	Phase 1
0.6989	Remote Similarity	NPD7229	Phase 3
0.6974	Remote Similarity	NPD17	Approved
0.6954	Remote Similarity	NPD1548	Phase 1
0.6948	Remote Similarity	NPD1608	Approved
0.6948	Remote Similarity	NPD9717	Approved
0.6946	Remote Similarity	NPD7390	Discontinued
0.6937	Remote Similarity	NPD4307	Phase 2
0.6933	Remote Similarity	NPD3539	Phase 1
0.6918	Remote Similarity	NPD6798	Discontinued
0.6918	Remote Similarity	NPD3268	Approved
0.6911	Remote Similarity	NPD6780	Approved
0.6911	Remote Similarity	NPD6782	Approved
0.6911	Remote Similarity	NPD6777	Approved
0.6911	Remote Similarity	NPD6781	Approved
0.6911	Remote Similarity	NPD6779	Approved
0.6911	Remote Similarity	NPD6778	Approved
0.6911	Remote Similarity	NPD6776	Approved
0.6905	Remote Similarity	NPD3688	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD3146	Approved
0.6903	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.689	Remote Similarity	NPD2353	Approved
0.689	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6883	Remote Similarity	NPD422	Phase 1
0.6879	Remote Similarity	NPD1019	Discontinued
0.6875	Remote Similarity	NPD4062	Phase 3
0.6871	Remote Similarity	NPD7033	Discontinued
0.6871	Remote Similarity	NPD4308	Phase 3
0.6868	Remote Similarity	NPD7685	Pre-registration
0.6859	Remote Similarity	NPD3225	Approved
0.6846	Remote Similarity	NPD1241	Discontinued
0.6845	Remote Similarity	NPD4357	Discontinued
0.6839	Remote Similarity	NPD3972	Approved
0.6839	Remote Similarity	NPD4288	Approved
0.6833	Remote Similarity	NPD2163	Approved
0.6826	Remote Similarity	NPD2354	Approved
0.6826	Remote Similarity	NPD3887	Approved
0.6815	Remote Similarity	NPD2797	Approved
0.6813	Remote Similarity	NPD411	Approved
0.6807	Remote Similarity	NPD1652	Phase 2
0.6804	Remote Similarity	NPD7697	Approved
0.6804	Remote Similarity	NPD7696	Phase 3
0.6804	Remote Similarity	NPD7698	Approved
0.6804	Remote Similarity	NPD7435	Discontinued
0.68	Remote Similarity	NPD5019	Clinical (unspecified phase)
0.6797	Remote Similarity	NPD9268	Approved
0.6792	Remote Similarity	NPD4908	Phase 1
0.679	Remote Similarity	NPD6355	Discontinued
0.6774	Remote Similarity	NPD8150	Discontinued
0.6774	Remote Similarity	NPD1610	Phase 2
0.6769	Remote Similarity	NPD7870	Phase 2
0.6769	Remote Similarity	NPD7871	Phase 2
0.6766	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6761	Remote Similarity	NPD6971	Discontinued
0.674	Remote Similarity	NPD7228	Approved
0.6739	Remote Similarity	NPD7549	Discontinued
0.6737	Remote Similarity	NPD4363	Phase 3
0.6737	Remote Similarity	NPD4360	Phase 2
0.6733	Remote Similarity	NPD5283	Phase 1

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