NPASS Compound

Structure

CID178202 OpenBabel06191715552D 23 25 0 0 0 0 0 0 0 0999 V2000 6.1472 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2812 2.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4152 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0878 1.6750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0878 -0.0570 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.6180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5878 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 -0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2812 1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5878 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0878 1.6750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0878 -0.0570 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5878 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5878 2.5411 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5878 -0.9230 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 -0.1910 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 11 1 0 0 0 0 2 11 1 0 0 0 0 3 4 1 0 0 0 0 3 11 2 0 0 0 0 4 12 1 0 0 0 0 5 12 2 0 0 0 0 5 13 1 0 0 0 0 6 14 2 0 0 0 0 6 15 1 0 0 0 0 7 14 1 0 0 0 0 7 16 2 0 0 0 0 8 13 1 0 0 0 0 8 18 2 0 0 0 0 9 15 2 0 0 0 0 9 16 1 0 0 0 0 10 17 2 0 0 0 0 10 19 1 0 0 0 0 12 17 1 0 0 0 0 13 19 2 0 0 0 0 14 18 1 0 0 0 0 15 20 1 0 0 0 0 16 21 1 0 0 0 0 17 22 1 0 0 0 0 18 23 1 0 0 0 0 19 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	310.12
Volume:	325.58
LogP:	5.083
LogD:	3.515
LogS:	-3.496
# Rotatable Bonds:	3
TPSA:	73.83
# H-Bond Aceptor:	4
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.612
Synthetic Accessibility Score:	2.704
Fsp3:	0.158
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.979
MDCK Permeability:	1.52438606164651e-05
Pgp-inhibitor:	0.049
Pgp-substrate:	0.796
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	0.999
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.027
Plasma Protein Binding (PPB):	98.38045501708984%
Volume Distribution (VD):	1.322
Pgp-substrate:	2.0171825885772705%

ADMET: Metabolism

CYP1A2-inhibitor:	0.984
CYP1A2-substrate:	0.229
CYP2C19-inhibitor:	0.932
CYP2C19-substrate:	0.055
CYP2C9-inhibitor:	0.699
CYP2C9-substrate:	0.931
CYP2D6-inhibitor:	0.959
CYP2D6-substrate:	0.872
CYP3A4-inhibitor:	0.894
CYP3A4-substrate:	0.113

ADMET: Excretion

Clearance (CL):	12.161
Half-life (T1/2):	0.764

ADMET: Toxicity

hERG Blockers:	0.1
Human Hepatotoxicity (H-HT):	0.258
Drug-inuced Liver Injury (DILI):	0.557
AMES Toxicity:	0.051
Rat Oral Acute Toxicity:	0.091
Maximum Recommended Daily Dose:	0.945
Skin Sensitization:	0.949
Carcinogencity:	0.045
Eye Corrosion:	0.004
Eye Irritation:	0.911
Respiratory Toxicity:	0.514

Download Data

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

Natural Product: NPC178202

Natural Product ID:	NPC178202
*Common Name:**	Moracin N
IUPAC Name:	5-[6-hydroxy-5-(3-methylbut-2-enyl)-1-benzofuran-2-yl]benzene-1,3-diol
Synonyms:	Moracin N
Standard InCHIKey:	WBSCSIABHGPAMC-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C19H18O4/c1-11(2)3-4-12-5-13-8-18(23-19(13)10-17(12)22)14-6-15(20)9-16(21)7-14/h3,5-10,20-22H,4H2,1-2H3
SMILES:	CC(=CCc1cc2cc(oc2cc1O)c1cc(O)cc(c1)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL465881
PubChem CID:	641376
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0003405] 2-arylbenzofuran 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
NPO5495	Broussonetia papyrifera	Species	Moraceae	Eukaryota	n.a.	root	n.a.	PMID[11395279]
NPO5495	Broussonetia papyrifera	Species	Moraceae	Eukaryota	whole plants	Shawnee National Forest, Harrisburg, IL, US	n.a.	PMID[11678652]
NPO5495	Broussonetia papyrifera	Species	Moraceae	Eukaryota	whole plants	n.a.	n.a.	PMID[11678652]
NPO5495	Broussonetia papyrifera	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12419367]
NPO5495	Broussonetia papyrifera	Species	Moraceae	Eukaryota	leaves	Kaohsiung, Taiwan	2006-SEP	PMID[18986201]
NPO5495	Broussonetia papyrifera	Species	Moraceae	Eukaryota	Fruits	n.a.	n.a.	PMID[19296617]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20815207]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	bark	n.a.	PMID[21319773]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	root	n.a.	PMID[21319773]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	leaf	n.a.	PMID[21319773]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	leaf	n.a.	PMID[22207282]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	root	n.a.	PMID[23806866]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	root bark	University of Veterinary and Pharmaceutical Sciences Brno (UVPS Brno), Brno, Czech Republic	2011-APR	PMID[24901948]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	Konya, Turkey	2007-APR	PMID[24901948]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	leaves	Chungbuk, Korea	n.a.	PMID[25935644]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	root	n.a.	PMID[25981820]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	latex	n.a.	PMID[27294120]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	Root barks	n.a.	n.a.	PMID[3097265]
NPO5495	Broussonetia papyrifera	Species	Moraceae	Eukaryota	n.a.	formosan	n.a.	PMID[8864236]
NPO5495	Broussonetia papyrifera	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9358644]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5495	Broussonetia papyrifera	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5495	Broussonetia papyrifera	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO5495	Broussonetia papyrifera	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO5495	Broussonetia papyrifera	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5495	Broussonetia papyrifera	Species	Moraceae	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	10
MIC	3
Others	2

Activity Type	# Activity
Cell Line	2
Individual Protein	5
NON-MOLECULAR	4
Organism	3
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT441	Individual Protein	Cytochrome P450 19A1	Homo sapiens	IC50	=	31100.0	nM	PMID[561856]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	10.0	ug.mL-1	PMID[561857]
NPT179	Cell Line	A2780	Homo sapiens	IC50	>	10.0	ug.mL-1	PMID[561857]
NPT441	Individual Protein	Cytochrome P450 19A1	Homo sapiens	IC50	=	31100.0	nM	PMID[561857]
NPT43	Individual Protein	Tyrosinase	Agaricus bisporus	IC50	=	924.0	nM	PMID[561857]
NPT1120	Individual Protein	Pancreatic triacylglycerol lipase	Sus scrofa	Inhibition	=	61.7	%	PMID[561858]
NPT1120	Individual Protein	Pancreatic triacylglycerol lipase	Sus scrofa	IC50	=	29700.0	nM	PMID[561858]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	100.0	ug.mL-1	PMID[561857]
NPT173	Organism	Klebsiella pneumoniae	Klebsiella pneumoniae	MIC	>	100.0	ug.mL-1	PMID[561857]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	MIC	>	100.0	ug.mL-1	PMID[561857]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	10.0	ug.mL-1	PMID[561857]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	76.0	%	PMID[561857]
NPT2	Others	Unspecified		IC50	=	2760.0	nM	PMID[561857]

☑ 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 NPC178202 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	416
0.1-0.2	1837
0.2-0.3	4381
0.3-0.4	11378
0.4-0.5	6689
0.5-0.6	3968
0.6-0.7	5457
0.7-0.8	4664
0.8-0.85	2251
0.85-0.9	1479
0.9-0.95	140
0.95-1	37

Similarity Score	Similarity Level	Natural Product ID
0.993	High Similarity	NPC78335
0.993	High Similarity	NPC230713
0.9861	High Similarity	NPC170169
0.9726	High Similarity	NPC472462
0.9726	High Similarity	NPC183874
0.9726	High Similarity	NPC235333
0.9722	High Similarity	NPC226644
0.9722	High Similarity	NPC37226
0.972	High Similarity	NPC17816
0.966	High Similarity	NPC148938
0.966	High Similarity	NPC198490
0.966	High Similarity	NPC213936
0.966	High Similarity	NPC297531
0.9655	High Similarity	NPC167576
0.965	High Similarity	NPC210826
0.9595	High Similarity	NPC180924
0.9589	High Similarity	NPC106372
0.9589	High Similarity	NPC23668
0.9589	High Similarity	NPC193976
0.9589	High Similarity	NPC58668
0.9583	High Similarity	NPC12148
0.9583	High Similarity	NPC130581
0.958	High Similarity	NPC155144
0.953	High Similarity	NPC164110
0.953	High Similarity	NPC212967
0.953	High Similarity	NPC246647
0.953	High Similarity	NPC96342
0.953	High Similarity	NPC268360
0.9524	High Similarity	NPC5871
0.9524	High Similarity	NPC142308
0.9524	High Similarity	NPC207624
0.9517	High Similarity	NPC135325
0.9514	High Similarity	NPC300267
0.9514	High Similarity	NPC51641
0.951	High Similarity	NPC225884
0.9459	High Similarity	NPC1477
0.9459	High Similarity	NPC72370
0.9459	High Similarity	NPC213608
0.9456	High Similarity	NPC115324
0.9452	High Similarity	NPC37208
0.9452	High Similarity	NPC221868
0.9452	High Similarity	NPC296030
0.9452	High Similarity	NPC39929
0.9444	High Similarity	NPC98926
0.9404	High Similarity	NPC304839
0.9404	High Similarity	NPC220582
0.9396	High Similarity	NPC99199
0.9392	High Similarity	NPC253872
0.9384	High Similarity	NPC272194
0.9375	High Similarity	NPC302181
0.9342	High Similarity	NPC45124
0.9342	High Similarity	NPC30655
0.9342	High Similarity	NPC74854
0.9333	High Similarity	NPC160015
0.9333	High Similarity	NPC247677
0.931	High Similarity	NPC230943
0.9306	High Similarity	NPC53192
0.9272	High Similarity	NPC65504
0.9272	High Similarity	NPC296957
0.9272	High Similarity	NPC260902
0.9262	High Similarity	NPC263676
0.9252	High Similarity	NPC186397
0.9252	High Similarity	NPC37135
0.9211	High Similarity	NPC476349
0.9211	High Similarity	NPC476350
0.9211	High Similarity	NPC244750
0.9211	High Similarity	NPC40583
0.9205	High Similarity	NPC137100
0.9205	High Similarity	NPC45131
0.92	High Similarity	NPC122365
0.9195	High Similarity	NPC116604
0.9189	High Similarity	NPC317492
0.9189	High Similarity	NPC223988
0.9189	High Similarity	NPC266499
0.9172	High Similarity	NPC96791
0.9172	High Similarity	NPC226942
0.9172	High Similarity	NPC470636
0.9167	High Similarity	NPC28337
0.9161	High Similarity	NPC37183
0.9156	High Similarity	NPC193998
0.915	High Similarity	NPC115432
0.915	High Similarity	NPC260296
0.9133	High Similarity	NPC125300
0.9133	High Similarity	NPC67654
0.9128	High Similarity	NPC13282
0.9122	High Similarity	NPC168085
0.9116	High Similarity	NPC24136
0.9116	High Similarity	NPC290133
0.9116	High Similarity	NPC187282
0.911	High Similarity	NPC262935
0.911	High Similarity	NPC251182
0.911	High Similarity	NPC172182
0.9103	High Similarity	NPC277480
0.9103	High Similarity	NPC53640
0.9097	High Similarity	NPC159508
0.9091	High Similarity	NPC304387
0.9085	High Similarity	NPC196879
0.9067	High Similarity	NPC156244
0.906	High Similarity	NPC65775
0.906	High Similarity	NPC10027
0.9048	High Similarity	NPC311741
0.9048	High Similarity	NPC234629
0.9045	High Similarity	NPC286230
0.9045	High Similarity	NPC50394
0.9045	High Similarity	NPC253730
0.9045	High Similarity	NPC247973
0.9041	High Similarity	NPC144499
0.9038	High Similarity	NPC169471
0.9034	High Similarity	NPC270883
0.9034	High Similarity	NPC261227
0.9034	High Similarity	NPC69769
0.9034	High Similarity	NPC172986
0.9032	High Similarity	NPC84515
0.9032	High Similarity	NPC272722
0.9032	High Similarity	NPC312056
0.9032	High Similarity	NPC219861
0.902	High Similarity	NPC196448
0.9007	High Similarity	NPC38361
0.9007	High Similarity	NPC130015
0.9	High Similarity	NPC227122
0.9	High Similarity	NPC101957
0.9	High Similarity	NPC120105
0.9	High Similarity	NPC472421
0.8993	High Similarity	NPC39195
0.8987	High Similarity	NPC211309
0.898	High Similarity	NPC17262
0.898	High Similarity	NPC212932
0.898	High Similarity	NPC190637
0.898	High Similarity	NPC293053
0.898	High Similarity	NPC166138
0.898	High Similarity	NPC24821
0.898	High Similarity	NPC106985
0.898	High Similarity	NPC18585
0.898	High Similarity	NPC9117
0.8974	High Similarity	NPC133065
0.8974	High Similarity	NPC472581
0.8974	High Similarity	NPC155640
0.8973	High Similarity	NPC156590
0.8973	High Similarity	NPC118840
0.8973	High Similarity	NPC110969
0.8973	High Similarity	NPC205006
0.8973	High Similarity	NPC64908
0.8973	High Similarity	NPC147688
0.8968	High Similarity	NPC188486
0.8966	High Similarity	NPC216978
0.8966	High Similarity	NPC55018
0.8966	High Similarity	NPC301217
0.8966	High Similarity	NPC303633
0.8966	High Similarity	NPC477956
0.8966	High Similarity	NPC96565
0.8966	High Similarity	NPC220062
0.8961	High Similarity	NPC472877
0.8961	High Similarity	NPC16935
0.8958	High Similarity	NPC62735
0.8958	High Similarity	NPC472419
0.8954	High Similarity	NPC472461
0.8951	High Similarity	NPC163029
0.8947	High Similarity	NPC189130
0.894	High Similarity	NPC258249
0.894	High Similarity	NPC474744
0.894	High Similarity	NPC472423
0.894	High Similarity	NPC474772
0.894	High Similarity	NPC318424
0.8933	High Similarity	NPC269420
0.8933	High Similarity	NPC158338
0.8933	High Similarity	NPC97028
0.8933	High Similarity	NPC100985
0.8933	High Similarity	NPC97029
0.8933	High Similarity	NPC65589
0.8933	High Similarity	NPC288036
0.8931	High Similarity	NPC218533
0.8931	High Similarity	NPC131866
0.8931	High Similarity	NPC78830
0.8926	High Similarity	NPC308200
0.8926	High Similarity	NPC198427
0.8919	High Similarity	NPC470890
0.8919	High Similarity	NPC326500
0.8919	High Similarity	NPC224714
0.8919	High Similarity	NPC216538
0.8919	High Similarity	NPC273538
0.8917	High Similarity	NPC329215
0.8917	High Similarity	NPC36320
0.8917	High Similarity	NPC38914
0.8917	High Similarity	NPC204088
0.8917	High Similarity	NPC259007
0.8917	High Similarity	NPC291110
0.8917	High Similarity	NPC39306
0.8912	High Similarity	NPC11561
0.8912	High Similarity	NPC159855
0.8912	High Similarity	NPC226636
0.8912	High Similarity	NPC473042
0.8912	High Similarity	NPC169479
0.8912	High Similarity	NPC200694
0.8912	High Similarity	NPC73028
0.8904	High Similarity	NPC235239
0.8904	High Similarity	NPC475680
0.8904	High Similarity	NPC241100
0.8904	High Similarity	NPC253822
0.8904	High Similarity	NPC159275
0.8904	High Similarity	NPC305355

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 NPC178202 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	388
0.1-0.2	1001
0.2-0.3	1574
0.3-0.4	2743
0.4-0.5	1830
0.5-0.6	1091
0.6-0.7	345
0.7-0.8	113
0.8-0.85	48
0.85-0.9	17
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8919	High Similarity	NPD4378	Clinical (unspecified phase)
0.8792	High Similarity	NPD7410	Clinical (unspecified phase)
0.8707	High Similarity	NPD1243	Approved
0.8707	High Similarity	NPD2800	Approved
0.8701	High Similarity	NPD2393	Clinical (unspecified phase)
0.8699	High Similarity	NPD2344	Approved
0.8654	High Similarity	NPD3749	Approved
0.859	High Similarity	NPD3882	Suspended
0.8553	High Similarity	NPD920	Approved
0.8542	High Similarity	NPD1240	Approved
0.8514	High Similarity	NPD1549	Phase 2
0.8491	Intermediate Similarity	NPD6959	Discontinued
0.8477	Intermediate Similarity	NPD1511	Approved
0.8476	Intermediate Similarity	NPD6559	Discontinued
0.8467	Intermediate Similarity	NPD2309	Approved
0.8462	Intermediate Similarity	NPD7819	Suspended
0.8462	Intermediate Similarity	NPD2801	Approved
0.8452	Intermediate Similarity	NPD7411	Suspended
0.8446	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8446	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8435	Intermediate Similarity	NPD1510	Phase 2
0.8425	Intermediate Similarity	NPD1607	Approved
0.8421	Intermediate Similarity	NPD2533	Approved
0.8421	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.8421	Intermediate Similarity	NPD2532	Approved
0.8421	Intermediate Similarity	NPD2534	Approved
0.8408	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8397	Intermediate Similarity	NPD1934	Approved
0.8387	Intermediate Similarity	NPD4380	Phase 2
0.8378	Intermediate Similarity	NPD2796	Approved
0.8366	Intermediate Similarity	NPD1512	Approved
0.8313	Intermediate Similarity	NPD5494	Approved
0.8302	Intermediate Similarity	NPD7075	Discontinued
0.8289	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.8272	Intermediate Similarity	NPD3926	Phase 2
0.8261	Intermediate Similarity	NPD1247	Approved
0.8255	Intermediate Similarity	NPD2935	Discontinued
0.8239	Intermediate Similarity	NPD7768	Phase 2
0.8232	Intermediate Similarity	NPD3818	Discontinued
0.8228	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8221	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.821	Intermediate Similarity	NPD6232	Discontinued
0.8171	Intermediate Similarity	NPD7473	Discontinued
0.8146	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8137	Intermediate Similarity	NPD919	Approved
0.8125	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8117	Intermediate Similarity	NPD6799	Approved
0.811	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.811	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.811	Intermediate Similarity	NPD6166	Phase 2
0.8092	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8075	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8067	Intermediate Similarity	NPD2799	Discontinued
0.8067	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.805	Intermediate Similarity	NPD6801	Discontinued
0.8039	Intermediate Similarity	NPD3750	Approved
0.8	Intermediate Similarity	NPD7390	Discontinued
0.7975	Intermediate Similarity	NPD3226	Approved
0.795	Intermediate Similarity	NPD3817	Phase 2
0.7933	Intermediate Similarity	NPD6651	Approved
0.7925	Intermediate Similarity	NPD6599	Discontinued
0.7919	Intermediate Similarity	NPD943	Approved
0.7905	Intermediate Similarity	NPD2313	Discontinued
0.7895	Intermediate Similarity	NPD1551	Phase 2
0.787	Intermediate Similarity	NPD5953	Discontinued
0.7857	Intermediate Similarity	NPD7286	Phase 2
0.7857	Intermediate Similarity	NPD5844	Phase 1
0.7857	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7843	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7843	Intermediate Similarity	NPD2346	Discontinued
0.784	Intermediate Similarity	NPD2296	Approved
0.7811	Intermediate Similarity	NPD7074	Phase 3
0.7785	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD6100	Approved
0.7778	Intermediate Similarity	NPD6099	Approved
0.7778	Intermediate Similarity	NPD1465	Phase 2
0.7778	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD5710	Approved
0.7771	Intermediate Similarity	NPD5711	Approved
0.7751	Intermediate Similarity	NPD7054	Approved
0.773	Intermediate Similarity	NPD5402	Approved
0.7727	Intermediate Similarity	NPD1471	Phase 3
0.7712	Intermediate Similarity	NPD3748	Approved
0.7706	Intermediate Similarity	NPD7472	Approved
0.7692	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7687	Intermediate Similarity	NPD1203	Approved
0.7665	Intermediate Similarity	NPD7229	Phase 3
0.7661	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7661	Intermediate Similarity	NPD6797	Phase 2
0.7625	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7616	Intermediate Similarity	NPD7251	Discontinued
0.7614	Intermediate Similarity	NPD4287	Approved
0.7588	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7572	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7572	Intermediate Similarity	NPD7808	Phase 3
0.755	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD447	Suspended
0.7516	Intermediate Similarity	NPD2654	Approved
0.7516	Intermediate Similarity	NPD5403	Approved
0.7516	Intermediate Similarity	NPD230	Phase 1
0.75	Intermediate Similarity	NPD1729	Discontinued
0.75	Intermediate Similarity	NPD6280	Approved
0.75	Intermediate Similarity	NPD6279	Approved
0.7483	Intermediate Similarity	NPD4625	Phase 3
0.7483	Intermediate Similarity	NPD9717	Approved
0.7468	Intermediate Similarity	NPD4628	Phase 3
0.7436	Intermediate Similarity	NPD5406	Approved
0.7436	Intermediate Similarity	NPD5405	Approved
0.7436	Intermediate Similarity	NPD5408	Approved
0.7436	Intermediate Similarity	NPD5404	Approved
0.7434	Intermediate Similarity	NPD3764	Approved
0.7417	Intermediate Similarity	NPD6832	Phase 2
0.7417	Intermediate Similarity	NPD4908	Phase 1
0.7403	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.74	Intermediate Similarity	NPD2798	Approved
0.7391	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD5401	Approved
0.7372	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD1608	Approved
0.7353	Intermediate Similarity	NPD6808	Phase 2
0.7351	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7349	Intermediate Similarity	NPD5760	Phase 2
0.7349	Intermediate Similarity	NPD5761	Phase 2
0.7333	Intermediate Similarity	NPD1470	Approved
0.7329	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD3268	Approved
0.732	Intermediate Similarity	NPD411	Approved
0.7317	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7314	Intermediate Similarity	NPD3658	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD4361	Phase 2
0.7308	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD8434	Phase 2
0.7297	Intermediate Similarity	NPD422	Phase 1
0.7297	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD2403	Approved
0.7261	Intermediate Similarity	NPD4308	Phase 3
0.7261	Intermediate Similarity	NPD7033	Discontinued
0.7253	Intermediate Similarity	NPD4363	Phase 3
0.7253	Intermediate Similarity	NPD4360	Phase 2
0.7243	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7238	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7232	Intermediate Similarity	NPD8313	Approved
0.7232	Intermediate Similarity	NPD8312	Approved
0.7229	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD1164	Approved
0.7219	Intermediate Similarity	NPD2797	Approved
0.72	Intermediate Similarity	NPD4749	Approved
0.7193	Intermediate Similarity	NPD7199	Phase 2
0.7186	Intermediate Similarity	NPD37	Approved
0.7184	Intermediate Similarity	NPD3751	Discontinued
0.7181	Intermediate Similarity	NPD1610	Phase 2
0.7181	Intermediate Similarity	NPD1201	Approved
0.7176	Intermediate Similarity	NPD6234	Discontinued
0.7174	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7162	Intermediate Similarity	NPD17	Approved
0.716	Intermediate Similarity	NPD4966	Approved
0.716	Intermediate Similarity	NPD4965	Approved
0.716	Intermediate Similarity	NPD4967	Phase 2
0.7143	Intermediate Similarity	NPD7003	Approved
0.7143	Intermediate Similarity	NPD1548	Phase 1
0.7133	Intermediate Similarity	NPD3972	Approved
0.712	Intermediate Similarity	NPD8151	Discontinued
0.7118	Intermediate Similarity	NPD6971	Discontinued
0.7115	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD1613	Approved
0.711	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD4288	Approved
0.7086	Intermediate Similarity	NPD7177	Discontinued
0.7083	Intermediate Similarity	NPD6844	Discontinued
0.7073	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7069	Intermediate Similarity	NPD4575	Clinical (unspecified phase)
0.7062	Intermediate Similarity	NPD1252	Clinical (unspecified phase)
0.7052	Intermediate Similarity	NPD3787	Discontinued
0.7049	Intermediate Similarity	NPD3269	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD3225	Approved
0.7032	Intermediate Similarity	NPD3027	Phase 3
0.7027	Intermediate Similarity	NPD9545	Approved
0.702	Intermediate Similarity	NPD9269	Phase 2
0.7019	Intermediate Similarity	NPD2424	Discontinued
0.7013	Intermediate Similarity	NPD2861	Phase 2
0.7007	Intermediate Similarity	NPD9493	Approved
0.7006	Intermediate Similarity	NPD7458	Discontinued
0.7006	Intermediate Similarity	NPD4307	Phase 2
0.6993	Remote Similarity	NPD3267	Approved
0.6993	Remote Similarity	NPD3266	Approved
0.6987	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6987	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6987	Remote Similarity	NPD1296	Phase 2
0.698	Remote Similarity	NPD9268	Approved
0.698	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.698	Remote Similarity	NPD1651	Approved
0.6968	Remote Similarity	NPD6777	Approved
0.6968	Remote Similarity	NPD6781	Approved
0.6968	Remote Similarity	NPD6776	Approved
0.6968	Remote Similarity	NPD6779	Approved
0.6968	Remote Similarity	NPD6780	Approved
0.6968	Remote Similarity	NPD6778	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