NPASS Compound

Structure

NPC243877 OpenBabel07101718222D 39 43 0 0 1 0 0 0 0 0999 V2000 -6.0622 5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 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 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 4.0000 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 3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 3.0000 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 -2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 3.0000 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 -0.8660 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -0.5000 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 0.8660 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7321 3.0000 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 1.7321 0.0000 0.0000 C 0 0 2 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 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 5.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 4.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 3.0000 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 1.7321 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 33 1 0 0 0 0 2 34 1 0 0 0 0 3 35 1 0 0 0 0 4 36 1 0 0 0 0 5 6 2 0 0 0 0 5 13 1 0 0 0 0 6 18 1 0 0 0 0 7 13 2 0 0 0 0 7 17 1 0 0 0 0 8 14 2 0 0 0 0 8 19 1 0 0 0 0 9 14 1 0 0 0 0 9 20 2 0 0 0 0 10 15 2 0 0 0 0 10 21 1 0 0 0 0 11 29 1 0 0 0 0 12 16 2 0 0 0 0 12 37 1 0 0 0 0 13 16 1 0 0 0 0 15 23 1 0 0 0 0 15 26 1 0 0 0 0 16 23 1 0 0 0 0 17 18 2 0 0 0 0 17 30 1 0 0 0 0 18 33 1 0 0 0 0 19 24 2 0 0 0 0 19 34 1 0 0 0 0 20 24 1 0 0 0 0 20 35 1 0 0 0 0 21 27 2 0 0 0 0 21 36 1 0 0 0 0 22 11 1 1 0 0 0 22 25 1 0 0 0 0 22 38 1 0 0 0 0 23 31 2 0 0 0 0 24 32 1 0 0 0 0 25 14 1 6 0 0 0 25 39 1 0 0 0 0 26 28 2 0 0 0 0 26 37 1 0 0 0 0 27 28 1 0 0 0 0 27 39 1 0 0 0 0 28 38 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	538.15
Volume:	517.753
LogP:	2.878
LogD:	2.347
LogS:	-4.606
# Rotatable Bonds:	7
TPSA:	146.28
# H-Bond Aceptor:	11
# H-Bond Donor:	3
# Rings:	5
# Heavy Atoms:	11

MedChem Properties

QED Drug-Likeness Score:	0.316
Synthetic Accessibility Score:	3.719
Fsp3:	0.25
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.322
MDCK Permeability:	2.6203584639006294e-05
Pgp-inhibitor:	0.998
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.04
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.003

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.016
Plasma Protein Binding (PPB):	76.44600677490234%
Volume Distribution (VD):	0.524
Pgp-substrate:	40.358646392822266%

ADMET: Metabolism

CYP1A2-inhibitor:	0.056
CYP1A2-substrate:	0.942
CYP2C19-inhibitor:	0.128
CYP2C19-substrate:	0.137
CYP2C9-inhibitor:	0.886
CYP2C9-substrate:	0.717
CYP2D6-inhibitor:	0.043
CYP2D6-substrate:	0.582
CYP3A4-inhibitor:	0.35
CYP3A4-substrate:	0.853

ADMET: Excretion

Clearance (CL):	2.745
Half-life (T1/2):	0.745

ADMET: Toxicity

hERG Blockers:	0.247
Human Hepatotoxicity (H-HT):	0.169
Drug-inuced Liver Injury (DILI):	0.858
AMES Toxicity:	0.063
Rat Oral Acute Toxicity:	0.646
Maximum Recommended Daily Dose:	0.39
Skin Sensitization:	0.775
Carcinogencity:	0.05
Eye Corrosion:	0.003
Eye Irritation:	0.107
Respiratory Toxicity:	0.07

Download Data

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

Natural Product: NPC243877

Natural Product ID:	NPC243877
*Common Name:**	5-Methoxyxanthocercin A
IUPAC Name:	(2R,3R)-3-(4-hydroxy-3,5-dimethoxyphenyl)-8-(3-hydroxy-4-methoxyphenyl)-2-(hydroxymethyl)-5-methoxy-2,3-dihydropyrano[3,2-h][1,4]benzodioxin-7-one
Synonyms:
Standard InCHIKey:	PDFRGLKIUUWXHS-RCZVLFRGSA-N
Standard InCHI:	InChI=1S/C28H26O11/c1-33-18-6-5-13(7-17(18)30)16-12-37-26-15(23(16)31)10-21(36-4)27-28(26)38-22(11-29)25(39-27)14-8-19(34-2)24(32)20(9-14)35-3/h5-10,12,22,25,29-30,32H,11H2,1-4H3/t22-,25-/m1/s1
SMILES:	COc1cc2c(c3c1O[C@H](c1cc(OC)c(c(c1)OC)O)[C@H](O3)CO)occ(c2=O)c1ccc(c(c1)O)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL466784
PubChem CID:	10886024
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:0003651] 3'-hydroxy,4'-methoxyisoflavonoids

*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
NPO5140	Dipteryx odorata	Species	Fabaceae	Eukaryota	seeds	n.a.	n.a.	PMID[12762787]
NPO5140	Dipteryx odorata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12762809]
NPO5140	Dipteryx odorata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5140	Dipteryx odorata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5140	Dipteryx odorata	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	1

Activity Type	# Activity
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT440	Individual Protein	Quinone oxidoreductase	Mus musculus	CD	>	10.0	ug ml-1	PMID[539044]

☑ 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 NPC243877 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	470
0.1-0.2	1893
0.2-0.3	4636
0.3-0.4	10704
0.4-0.5	7231
0.5-0.6	3932
0.6-0.7	5350
0.7-0.8	4971
0.8-0.85	1704
0.85-0.9	1316
0.9-0.95	479
0.95-1	11

Similarity Score	Similarity Level	Natural Product ID
0.9873	High Similarity	NPC14662
0.9748	High Similarity	NPC295082
0.9682	High Similarity	NPC66618
0.9682	High Similarity	NPC113163
0.9682	High Similarity	NPC84324
0.9682	High Similarity	NPC165970
0.9682	High Similarity	NPC305987
0.9682	High Similarity	NPC288131
0.9618	High Similarity	NPC101731
0.9557	High Similarity	NPC158188
0.9554	High Similarity	NPC284127
0.9554	High Similarity	NPC172202
0.9554	High Similarity	NPC476410
0.9503	High Similarity	NPC260266
0.95	High Similarity	NPC72787
0.95	High Similarity	NPC125039
0.95	High Similarity	NPC7688
0.95	High Similarity	NPC36
0.95	High Similarity	NPC7154
0.95	High Similarity	NPC36916
0.95	High Similarity	NPC58223
0.9497	High Similarity	NPC219927
0.9497	High Similarity	NPC476247
0.949	High Similarity	NPC99597
0.949	High Similarity	NPC210084
0.949	High Similarity	NPC475267
0.949	High Similarity	NPC156057
0.949	High Similarity	NPC474208
0.949	High Similarity	NPC470402
0.949	High Similarity	NPC474836
0.949	High Similarity	NPC162869
0.949	High Similarity	NPC183851
0.949	High Similarity	NPC63454
0.949	High Similarity	NPC48208
0.9448	High Similarity	NPC48773
0.9448	High Similarity	NPC271848
0.9448	High Similarity	NPC81332
0.9448	High Similarity	NPC262580
0.9448	High Similarity	NPC205076
0.9448	High Similarity	NPC289396
0.9448	High Similarity	NPC307518
0.9448	High Similarity	NPC212038
0.9444	High Similarity	NPC475212
0.9437	High Similarity	NPC272064
0.9434	High Similarity	NPC308992
0.9434	High Similarity	NPC26326
0.9434	High Similarity	NPC142252
0.9427	High Similarity	NPC255106
0.9427	High Similarity	NPC235165
0.9427	High Similarity	NPC472916
0.9398	High Similarity	NPC324742
0.9394	High Similarity	NPC472991
0.9394	High Similarity	NPC472992
0.9387	High Similarity	NPC105511
0.9387	High Similarity	NPC224462
0.9379	High Similarity	NPC142614
0.9379	High Similarity	NPC50960
0.9379	High Similarity	NPC477840
0.9375	High Similarity	NPC472448
0.9375	High Similarity	NPC220912
0.9375	High Similarity	NPC83922
0.9375	High Similarity	NPC477841
0.9371	High Similarity	NPC263449
0.9367	High Similarity	NPC245758
0.9367	High Similarity	NPC96167
0.9367	High Similarity	NPC472914
0.9367	High Similarity	NPC472911
0.9367	High Similarity	NPC472913
0.9367	High Similarity	NPC472910
0.9367	High Similarity	NPC222814
0.9363	High Similarity	NPC201136
0.9363	High Similarity	NPC196439
0.9363	High Similarity	NPC4455
0.9363	High Similarity	NPC138360
0.9363	High Similarity	NPC280339
0.9363	High Similarity	NPC213622
0.9363	High Similarity	NPC208197
0.9363	High Similarity	NPC128863
0.9363	High Similarity	NPC146165
0.9363	High Similarity	NPC92659
0.9363	High Similarity	NPC20830
0.9363	High Similarity	NPC183597
0.9363	High Similarity	NPC37392
0.9363	High Similarity	NPC2928
0.9363	High Similarity	NPC227325
0.9363	High Similarity	NPC167815
0.9363	High Similarity	NPC163780
0.9363	High Similarity	NPC256612
0.9363	High Similarity	NPC50715
0.9363	High Similarity	NPC2476
0.9337	High Similarity	NPC476620
0.9337	High Similarity	NPC472387
0.9337	High Similarity	NPC476621
0.9337	High Similarity	NPC476619
0.9337	High Similarity	NPC476622
0.9337	High Similarity	NPC476618
0.9337	High Similarity	NPC476623
0.9325	High Similarity	NPC226294
0.9325	High Similarity	NPC45638
0.9325	High Similarity	NPC469931
0.9325	High Similarity	NPC93337
0.9325	High Similarity	NPC186807
0.9325	High Similarity	NPC475942
0.9325	High Similarity	NPC58053
0.9325	High Similarity	NPC105025
0.9325	High Similarity	NPC201292
0.9313	High Similarity	NPC474038
0.9313	High Similarity	NPC228383
0.9313	High Similarity	NPC34089
0.9313	High Similarity	NPC266314
0.9313	High Similarity	NPC167678
0.9313	High Similarity	NPC196179
0.9313	High Similarity	NPC29876
0.9308	High Similarity	NPC190487
0.9308	High Similarity	NPC95936
0.9308	High Similarity	NPC154304
0.9308	High Similarity	NPC250214
0.9308	High Similarity	NPC53545
0.9308	High Similarity	NPC117418
0.9299	High Similarity	NPC69394
0.9299	High Similarity	NPC22519
0.9299	High Similarity	NPC472915
0.9299	High Similarity	NPC255350
0.9299	High Similarity	NPC145379
0.9299	High Similarity	NPC280937
0.9299	High Similarity	NPC231018
0.9299	High Similarity	NPC276409
0.9299	High Similarity	NPC18727
0.9299	High Similarity	NPC274327
0.9299	High Similarity	NPC183878
0.9299	High Similarity	NPC292214
0.9299	High Similarity	NPC271779
0.9299	High Similarity	NPC250557
0.9299	High Similarity	NPC176775
0.9299	High Similarity	NPC88645
0.9299	High Similarity	NPC250822
0.9299	High Similarity	NPC167091
0.9299	High Similarity	NPC124714
0.9299	High Similarity	NPC75279
0.9299	High Similarity	NPC160951
0.9299	High Similarity	NPC206238
0.9299	High Similarity	NPC47781
0.9286	High Similarity	NPC36138
0.9281	High Similarity	NPC185275
0.9273	High Similarity	NPC204693
0.9273	High Similarity	NPC51774
0.9273	High Similarity	NPC472993
0.9273	High Similarity	NPC239549
0.9273	High Similarity	NPC236191
0.9268	High Similarity	NPC34287
0.9268	High Similarity	NPC44558
0.9268	High Similarity	NPC103307
0.9268	High Similarity	NPC21190
0.9268	High Similarity	NPC471416
0.9268	High Similarity	NPC183357
0.9268	High Similarity	NPC231194
0.9268	High Similarity	NPC22195
0.9268	High Similarity	NPC51326
0.9268	High Similarity	NPC476365
0.9268	High Similarity	NPC474434
0.9264	High Similarity	NPC135345
0.9264	High Similarity	NPC146792
0.9264	High Similarity	NPC45618
0.9264	High Similarity	NPC229729
0.9264	High Similarity	NPC58716
0.9259	High Similarity	NPC224280
0.9259	High Similarity	NPC470457
0.9259	High Similarity	NPC234052
0.9259	High Similarity	NPC471788
0.9255	High Similarity	NPC474034
0.9255	High Similarity	NPC261470
0.9255	High Similarity	NPC474033
0.9255	High Similarity	NPC81679
0.925	High Similarity	NPC118256
0.925	High Similarity	NPC188967
0.925	High Similarity	NPC119209
0.925	High Similarity	NPC204290
0.925	High Similarity	NPC476980
0.925	High Similarity	NPC475784
0.925	High Similarity	NPC53889
0.925	High Similarity	NPC192686
0.9245	High Similarity	NPC299520
0.9245	High Similarity	NPC189179
0.9245	High Similarity	NPC474055
0.9245	High Similarity	NPC224137
0.9245	High Similarity	NPC78103
0.9245	High Similarity	NPC93376
0.9245	High Similarity	NPC78225
0.9245	High Similarity	NPC185526
0.9245	High Similarity	NPC472598
0.9245	High Similarity	NPC75215
0.9245	High Similarity	NPC227192
0.9245	High Similarity	NPC262286
0.9245	High Similarity	NPC223787
0.9245	High Similarity	NPC36852
0.9245	High Similarity	NPC52530
0.9245	High Similarity	NPC291508
0.9245	High Similarity	NPC469584
0.9245	High Similarity	NPC181960
0.9245	High Similarity	NPC129684

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 NPC243877 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	427
0.1-0.2	989
0.2-0.3	1949
0.3-0.4	2672
0.4-0.5	1748
0.5-0.6	892
0.6-0.7	315
0.7-0.8	112
0.8-0.85	22
0.85-0.9	19
0.9-0.95	5
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.95	High Similarity	NPD6167	Clinical (unspecified phase)
0.95	High Similarity	NPD6168	Clinical (unspecified phase)
0.95	High Similarity	NPD6166	Phase 2
0.9299	High Similarity	NPD2801	Approved
0.9236	High Similarity	NPD1934	Approved
0.9091	High Similarity	NPD7054	Approved
0.9062	High Similarity	NPD4868	Clinical (unspecified phase)
0.9057	High Similarity	NPD2393	Clinical (unspecified phase)
0.9036	High Similarity	NPD7472	Approved
0.9036	High Similarity	NPD7074	Phase 3
0.903	High Similarity	NPD3818	Discontinued
0.8988	High Similarity	NPD4338	Clinical (unspecified phase)
0.8869	High Similarity	NPD6797	Phase 2
0.8868	High Similarity	NPD4380	Phase 2
0.8827	High Similarity	NPD3882	Suspended
0.8817	High Similarity	NPD7251	Discontinued
0.878	High Similarity	NPD5494	Approved
0.8773	High Similarity	NPD4381	Clinical (unspecified phase)
0.8765	High Similarity	NPD7808	Phase 3
0.8757	High Similarity	NPD7993	Clinical (unspecified phase)
0.8726	High Similarity	NPD1511	Approved
0.865	High Similarity	NPD3817	Phase 2
0.8639	High Similarity	NPD5844	Phase 1
0.8616	High Similarity	NPD1512	Approved
0.8537	High Similarity	NPD5402	Approved
0.8438	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8434	Intermediate Similarity	NPD7075	Discontinued
0.8424	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8421	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8408	Intermediate Similarity	NPD1549	Phase 2
0.8393	Intermediate Similarity	NPD6959	Discontinued
0.8354	Intermediate Similarity	NPD7411	Suspended
0.8344	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8344	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8343	Intermediate Similarity	NPD6232	Discontinued
0.8323	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8304	Intermediate Similarity	NPD7473	Discontinued
0.8303	Intermediate Similarity	NPD6801	Discontinued
0.828	Intermediate Similarity	NPD2796	Approved
0.8253	Intermediate Similarity	NPD1465	Phase 2
0.8253	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8217	Intermediate Similarity	NPD1510	Phase 2
0.8171	Intermediate Similarity	NPD6559	Discontinued
0.8156	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.8144	Intermediate Similarity	NPD7819	Suspended
0.814	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.811	Intermediate Similarity	NPD5403	Approved
0.807	Intermediate Similarity	NPD1247	Approved
0.8037	Intermediate Similarity	NPD6799	Approved
0.7988	Intermediate Similarity	NPD5401	Approved
0.7977	Intermediate Similarity	NPD3926	Phase 2
0.7967	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7962	Intermediate Similarity	NPD1613	Approved
0.7962	Intermediate Similarity	NPD943	Approved
0.7962	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7962	Intermediate Similarity	NPD1240	Approved
0.7952	Intermediate Similarity	NPD1653	Approved
0.7943	Intermediate Similarity	NPD3751	Discontinued
0.7895	Intermediate Similarity	NPD3749	Approved
0.7892	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7862	Intermediate Similarity	NPD1607	Approved
0.7857	Intermediate Similarity	NPD6599	Discontinued
0.7836	Intermediate Similarity	NPD7768	Phase 2
0.7816	Intermediate Similarity	NPD3787	Discontinued
0.7805	Intermediate Similarity	NPD6190	Approved
0.779	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD8312	Approved
0.7778	Intermediate Similarity	NPD8313	Approved
0.7771	Intermediate Similarity	NPD3027	Phase 3
0.7759	Intermediate Similarity	NPD7199	Phase 2
0.7746	Intermediate Similarity	NPD919	Approved
0.7744	Intermediate Similarity	NPD3750	Approved
0.774	Intermediate Similarity	NPD7228	Approved
0.7716	Intermediate Similarity	NPD2935	Discontinued
0.7707	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7688	Intermediate Similarity	NPD230	Phase 1
0.7683	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7672	Intermediate Similarity	NPD6778	Approved
0.7672	Intermediate Similarity	NPD6776	Approved
0.7672	Intermediate Similarity	NPD6777	Approved
0.7672	Intermediate Similarity	NPD6779	Approved
0.7672	Intermediate Similarity	NPD6780	Approved
0.7672	Intermediate Similarity	NPD6781	Approved
0.7672	Intermediate Similarity	NPD6782	Approved
0.7667	Intermediate Similarity	NPD7685	Pre-registration
0.7644	Intermediate Similarity	NPD6234	Discontinued
0.7643	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7636	Intermediate Similarity	NPD4628	Phase 3
0.7622	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7606	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7579	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7578	Intermediate Similarity	NPD447	Suspended
0.7571	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7558	Intermediate Similarity	NPD6844	Discontinued
0.7558	Intermediate Similarity	NPD37	Approved
0.7554	Intermediate Similarity	NPD8150	Discontinued
0.7552	Intermediate Similarity	NPD7435	Discontinued
0.7538	Intermediate Similarity	NPD8151	Discontinued
0.753	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7529	Intermediate Similarity	NPD4967	Phase 2
0.7529	Intermediate Similarity	NPD4966	Approved
0.7529	Intermediate Similarity	NPD4965	Approved
0.7513	Intermediate Similarity	NPD7870	Phase 2
0.7513	Intermediate Similarity	NPD7871	Phase 2
0.75	Intermediate Similarity	NPD1551	Phase 2
0.75	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7390	Discontinued
0.7485	Intermediate Similarity	NPD3226	Approved
0.7484	Intermediate Similarity	NPD4908	Phase 1
0.7471	Intermediate Similarity	NPD920	Approved
0.747	Intermediate Similarity	NPD2800	Approved
0.7462	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7462	Intermediate Similarity	NPD7783	Phase 2
0.7461	Intermediate Similarity	NPD7696	Phase 3
0.7461	Intermediate Similarity	NPD7697	Approved
0.7461	Intermediate Similarity	NPD7698	Approved
0.7456	Intermediate Similarity	NPD2533	Approved
0.7456	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7456	Intermediate Similarity	NPD2534	Approved
0.7456	Intermediate Similarity	NPD2532	Approved
0.7455	Intermediate Similarity	NPD2344	Approved
0.7439	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7439	Intermediate Similarity	NPD3748	Approved
0.7432	Intermediate Similarity	NPD7549	Discontinued
0.7421	Intermediate Similarity	NPD9494	Approved
0.7418	Intermediate Similarity	NPD5953	Discontinued
0.7409	Intermediate Similarity	NPD6823	Phase 2
0.7407	Intermediate Similarity	NPD6535	Approved
0.7407	Intermediate Similarity	NPD6534	Approved
0.7398	Intermediate Similarity	NPD7701	Phase 2
0.7391	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7366	Intermediate Similarity	NPD8434	Phase 2
0.7362	Intermediate Similarity	NPD1933	Approved
0.7353	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD7584	Approved
0.7337	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7323	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7323	Intermediate Similarity	NPD7874	Approved
0.7316	Intermediate Similarity	NPD4363	Phase 3
0.7316	Intermediate Similarity	NPD4360	Phase 2
0.7314	Intermediate Similarity	NPD8455	Phase 2
0.7308	Intermediate Similarity	NPD7286	Phase 2
0.7292	Intermediate Similarity	NPD7700	Phase 2
0.7292	Intermediate Similarity	NPD7699	Phase 2
0.7289	Intermediate Similarity	NPD6099	Approved
0.7289	Intermediate Similarity	NPD6100	Approved
0.7286	Intermediate Similarity	NPD7801	Approved
0.7284	Intermediate Similarity	NPD2313	Discontinued
0.7283	Intermediate Similarity	NPD7240	Approved
0.7283	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD2309	Approved
0.7278	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7262	Intermediate Similarity	NPD1243	Approved
0.7261	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD7266	Discontinued
0.7246	Intermediate Similarity	NPD2346	Discontinued
0.7239	Intermediate Similarity	NPD6233	Phase 2
0.7235	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7229	Intermediate Similarity	NPD2799	Discontinued
0.7229	Intermediate Similarity	NPD7033	Discontinued
0.7212	Intermediate Similarity	NPD6651	Approved
0.7182	Intermediate Similarity	NPD5242	Approved
0.7178	Intermediate Similarity	NPD6798	Discontinued
0.7175	Intermediate Similarity	NPD5353	Approved
0.7173	Intermediate Similarity	NPD6212	Phase 3
0.7173	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7173	Intermediate Similarity	NPD6213	Phase 3
0.7167	Intermediate Similarity	NPD8127	Discontinued
0.716	Intermediate Similarity	NPD6832	Phase 2
0.7118	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD2861	Phase 2
0.7097	Intermediate Similarity	NPD7039	Approved
0.7097	Intermediate Similarity	NPD7038	Approved
0.7086	Intermediate Similarity	NPD7458	Discontinued
0.7081	Intermediate Similarity	NPD1203	Approved
0.7059	Intermediate Similarity	NPD1652	Phase 2
0.7053	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7049	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD5124	Phase 1
0.7048	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD1610	Phase 2
0.7037	Intermediate Similarity	NPD2798	Approved
0.7033	Intermediate Similarity	NPD5711	Approved
0.7033	Intermediate Similarity	NPD7229	Phase 3
0.7033	Intermediate Similarity	NPD5710	Approved
0.702	Intermediate Similarity	NPD7680	Approved
0.7016	Intermediate Similarity	NPD4287	Approved
0.7006	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD6385	Approved
0.7006	Intermediate Similarity	NPD6386	Approved
0.7006	Intermediate Similarity	NPD1548	Phase 1
0.7	Intermediate Similarity	NPD2424	Discontinued
0.7	Intermediate Similarity	NPD9269	Phase 2
0.6994	Remote Similarity	NPD7213	Phase 3
0.6994	Remote Similarity	NPD7212	Phase 2
0.699	Remote Similarity	NPD7237	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