NPASS Compound

Structure

NPC20541 OpenBabel07101719242D 21 23 0 0 0 0 0 0 0 0999 V2000 -1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 5.0000 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 0.0000 3.0000 0.0000 C 0 0 0 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 -1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 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 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 -1.7321 -0.0000 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 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -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 1.7321 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 4.5000 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 6 1 0 0 0 0 2 20 1 0 0 0 0 3 6 2 0 0 0 0 3 10 1 0 0 0 0 4 7 2 0 0 0 0 4 8 1 0 0 0 0 5 7 1 0 0 0 0 5 9 2 0 0 0 0 6 11 1 0 0 0 0 7 20 1 0 0 0 0 8 11 1 0 0 0 0 8 12 2 0 0 0 0 9 12 1 0 0 0 0 9 16 1 0 0 0 0 10 13 2 0 0 0 0 10 17 1 0 0 0 0 11 14 2 0 0 0 0 12 15 1 0 0 0 0 13 14 1 0 0 0 0 13 18 1 0 0 0 0 14 21 1 0 0 0 0 15 19 2 0 0 0 0 15 21 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	288.06
Volume:	276.613
LogP:	2.907
LogD:	2.45
LogS:	-3.517
# Rotatable Bonds:	1
TPSA:	100.13
# H-Bond Aceptor:	6
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.361
Synthetic Accessibility Score:	2.628
Fsp3:	0.133
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.082
MDCK Permeability:	7.448345513694221e-06
Pgp-inhibitor:	0.003
Pgp-substrate:	0.189
Human Intestinal Absorption (HIA):	0.075
20% Bioavailability (F20%):	0.013
30% Bioavailability (F30%):	0.904

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.008
Plasma Protein Binding (PPB):	93.47100067138672%
Volume Distribution (VD):	0.686
Pgp-substrate:	12.826706886291504%

ADMET: Metabolism

CYP1A2-inhibitor:	0.966
CYP1A2-substrate:	0.924
CYP2C19-inhibitor:	0.073
CYP2C19-substrate:	0.067
CYP2C9-inhibitor:	0.579
CYP2C9-substrate:	0.863
CYP2D6-inhibitor:	0.332
CYP2D6-substrate:	0.361
CYP3A4-inhibitor:	0.145
CYP3A4-substrate:	0.082

ADMET: Excretion

Clearance (CL):	7.642
Half-life (T1/2):	0.803

ADMET: Toxicity

hERG Blockers:	0.015
Human Hepatotoxicity (H-HT):	0.576
Drug-inuced Liver Injury (DILI):	0.982
AMES Toxicity:	0.43
Rat Oral Acute Toxicity:	0.134
Maximum Recommended Daily Dose:	0.886
Skin Sensitization:	0.885
Carcinogencity:	0.042
Eye Corrosion:	0.111
Eye Irritation:	0.933
Respiratory Toxicity:	0.245

Download Data

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

Natural Product: NPC20541

Natural Product ID:	NPC20541
*Common Name:**	3-Hydroxyalternariol 5-O-Methyl Ether
IUPAC Name:	3,4,7-trihydroxy-9-methoxy-1-methylbenzo[c]chromen-6-one
Synonyms:
Standard InCHIKey:	BVYAURIYXKOUPX-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C15H12O6/c1-6-3-10(17)13(18)14-11(6)8-4-7(20-2)5-9(16)12(8)15(19)21-14/h3-5,16-18H,1-2H3
SMILES:	COc1cc(O)c2c(c1)c1c(C)cc(c(c1oc2=O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL520144
PubChem CID:	24899916
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000145] Coumarins and derivatives [CHEMONTID:0002908] Hydroxycoumarins [CHEMONTID:0002644] 7,8-dihydroxycoumarins

*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
NPO32908	Alternaria sp.	Species	Pleosporaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18494522]
NPO32908	Alternaria sp.	Species	Pleosporaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22276679]
NPO32908	Alternaria sp.	Species	Pleosporaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25265160]
NPO32908	Alternaria sp.	Species	Pleosporaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26841051]
NPO32908	Alternaria sp.	Species	Pleosporaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[30794407]

☑ 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
EC50	1
IC50	26
Others	1

Activity Type	# Activity
Cell Line	1
Individual Protein	23
Organism	2
Others	1
Protein Complex	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1864	Cell Line	L5178Y	Mus musculus	Activity	=	47.1	%	PMID[512697]
NPT1660	Individual Protein	NUAK family SNF1-like kinase 1	Homo sapiens	IC50	=	0.35	ug.mL-1	PMID[512697]
NPT1432	Individual Protein	Serine/threonine-protein kinase Aurora-A	Homo sapiens	IC50	=	1.5	ug.mL-1	PMID[512697]
NPT1433	Individual Protein	Serine/threonine-protein kinase Aurora-B	Homo sapiens	IC50	=	1.1	ug.mL-1	PMID[512697]
NPT1434	Individual Protein	Serine/threonine-protein kinase B-raf	Homo sapiens	IC50	=	1.5	ug.mL-1	PMID[512697]
NPT1371	Individual Protein	Cyclin-dependent kinase 2	Homo sapiens	IC50	=	2.4	ug.mL-1	PMID[512697]
NPT2571	Individual Protein	Mitogen-activated protein kinase kinase kinase 8	Homo sapiens	IC50	=	2.3	ug.mL-1	PMID[512697]
NPT285	Individual Protein	Epidermal growth factor receptor erbB1	Homo sapiens	IC50	=	1.1	ug.mL-1	PMID[512697]
NPT2572	Individual Protein	Ephrin type-B receptor 4	Homo sapiens	IC50	=	2.1	ug.mL-1	PMID[512697]
NPT286	Individual Protein	Receptor protein-tyrosine kinase erbB-2	Homo sapiens	IC50	=	2.7	ug.mL-1	PMID[512697]
NPT1436	Individual Protein	Focal adhesion kinase 1	Homo sapiens	IC50	=	4.9	ug.mL-1	PMID[512697]
NPT1438	Individual Protein	Insulin-like growth factor I receptor	Homo sapiens	IC50	=	0.91	ug.mL-1	PMID[512697]
NPT36	Individual Protein	Tyrosine-protein kinase SRC	Homo sapiens	IC50	=	1.4	ug.mL-1	PMID[512697]
NPT1478	Individual Protein	Vascular endothelial growth factor receptor 2	Homo sapiens	IC50	=	0.64	ug.mL-1	PMID[512697]
NPT1650	Individual Protein	Tyrosine-protein kinase receptor FLT3	Homo sapiens	IC50	=	0.53	ug.mL-1	PMID[512697]
NPT2574	Individual Protein	Insulin receptor	Homo sapiens	IC50	=	1.3	ug.mL-1	PMID[512697]
NPT2575	Individual Protein	Platelet-derived growth factor receptor beta	Homo sapiens	IC50	=	1.8	ug.mL-1	PMID[512697]
NPT1598	Individual Protein	Casein kinase II alpha	Homo sapiens	IC50	>	10.0	ug.mL-1	PMID[512697]
NPT1702	Individual Protein	Serine/threonine-protein kinase PLK4	Homo sapiens	IC50	=	0.83	ug.mL-1	PMID[512697]
NPT2576	Individual Protein	Tyrosine-protein kinase TIE-2	Homo sapiens	IC50	=	1.4	ug.mL-1	PMID[512697]
NPT2573	Individual Protein	Vascular endothelial growth factor receptor 3	Homo sapiens	IC50	=	0.39	ug.mL-1	PMID[512697]
NPT1337	Individual Protein	Hepatocyte growth factor receptor	Homo sapiens	IC50	=	1.7	ug.mL-1	PMID[512697]
NPT1560	Protein Complex	Cyclin-dependent kinase 4/cyclin D1	Homo sapiens	IC50	=	1.7	ug.mL-1	PMID[512697]
NPT728	Individual Protein	Serine/threonine-protein kinase AKT	Homo sapiens	IC50	=	5.3	ug.mL-1	PMID[512697]
NPT831	Individual Protein	Serine/threonine-protein kinase PLK1	Homo sapiens	IC50	=	5.7	ug.mL-1	PMID[512697]
NPT35	Others	n.a.		EC50	=	68300.0	nM	PMID[512698]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	IC50	=	29000.0	nM	PMID[512698]
NPT26776	ORGANISM	Pseudomonas syringae pv. lachrymans	Pseudomonas syringae pv. lachrymans	IC50	=	7000.0	nM	PMID[512698]

☑ 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 NPC20541 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	419
0.1-0.2	2007
0.2-0.3	4758
0.3-0.4	10854
0.4-0.5	6772
0.5-0.6	3918
0.6-0.7	5222
0.7-0.8	5319
0.8-0.85	2149
0.85-0.9	1150
0.9-0.95	126
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9463	High Similarity	NPC151473
0.9456	High Similarity	NPC138978
0.9456	High Similarity	NPC267509
0.9408	High Similarity	NPC227062
0.9408	High Similarity	NPC54928
0.9388	High Similarity	NPC32470
0.9346	High Similarity	NPC247713
0.9286	High Similarity	NPC267627
0.9286	High Similarity	NPC37502
0.9286	High Similarity	NPC238381
0.9286	High Similarity	NPC40702
0.9272	High Similarity	NPC204350
0.9226	High Similarity	NPC200594
0.9221	High Similarity	NPC472963
0.9221	High Similarity	NPC241904
0.9221	High Similarity	NPC300727
0.9221	High Similarity	NPC111969
0.9211	High Similarity	NPC295646
0.9211	High Similarity	NPC260979
0.9205	High Similarity	NPC29231
0.9172	High Similarity	NPC474350
0.9161	High Similarity	NPC476242
0.9156	High Similarity	NPC274730
0.9156	High Similarity	NPC472907
0.915	High Similarity	NPC472905
0.915	High Similarity	NPC178134
0.915	High Similarity	NPC281477
0.915	High Similarity	NPC469550
0.9145	High Similarity	NPC227166
0.9145	High Similarity	NPC202157
0.9128	High Similarity	NPC134621
0.9116	High Similarity	NPC220106
0.9103	High Similarity	NPC228785
0.9103	High Similarity	NPC36217
0.9103	High Similarity	NPC56085
0.9103	High Similarity	NPC474960
0.9103	High Similarity	NPC14353
0.9097	High Similarity	NPC108456
0.9097	High Similarity	NPC136674
0.9091	High Similarity	NPC16082
0.9091	High Similarity	NPC38898
0.9091	High Similarity	NPC82592
0.9091	High Similarity	NPC67396
0.9091	High Similarity	NPC471800
0.9091	High Similarity	NPC199926
0.9085	High Similarity	NPC302950
0.9085	High Similarity	NPC180234
0.9085	High Similarity	NPC120537
0.9085	High Similarity	NPC236637
0.9085	High Similarity	NPC289968
0.9085	High Similarity	NPC219582
0.9085	High Similarity	NPC472912
0.9085	High Similarity	NPC101996
0.9085	High Similarity	NPC199100
0.9079	High Similarity	NPC194379
0.9073	High Similarity	NPC43669
0.9073	High Similarity	NPC196277
0.9073	High Similarity	NPC272721
0.9073	High Similarity	NPC120464
0.9067	High Similarity	NPC237208
0.9062	High Similarity	NPC165979
0.9062	High Similarity	NPC163130
0.906	High Similarity	NPC95123
0.906	High Similarity	NPC66404
0.9057	High Similarity	NPC472452
0.9054	High Similarity	NPC105648
0.9045	High Similarity	NPC278052
0.9045	High Similarity	NPC61010
0.9045	High Similarity	NPC40491
0.9038	High Similarity	NPC168616
0.9038	High Similarity	NPC83763
0.9038	High Similarity	NPC235448
0.9038	High Similarity	NPC100123
0.9032	High Similarity	NPC24640
0.9032	High Similarity	NPC150227
0.9026	High Similarity	NPC88645
0.9026	High Similarity	NPC18727
0.9026	High Similarity	NPC271779
0.9026	High Similarity	NPC292214
0.9026	High Similarity	NPC206238
0.9026	High Similarity	NPC167091
0.9026	High Similarity	NPC89474
0.902	High Similarity	NPC31363
0.902	High Similarity	NPC171010
0.9013	High Similarity	NPC183950
0.9013	High Similarity	NPC223579
0.9013	High Similarity	NPC137062
0.9013	High Similarity	NPC177298
0.9013	High Similarity	NPC287101
0.9013	High Similarity	NPC48479
0.9013	High Similarity	NPC52005
0.9007	High Similarity	NPC77378
0.9007	High Similarity	NPC476463
0.9006	High Similarity	NPC124470
0.9006	High Similarity	NPC109827
0.9	High Similarity	NPC29577
0.8994	High Similarity	NPC8070
0.8993	High Similarity	NPC310340
0.8987	High Similarity	NPC144843
0.8987	High Similarity	NPC201800
0.8987	High Similarity	NPC471745
0.8987	High Similarity	NPC294965
0.8987	High Similarity	NPC472964
0.8986	High Similarity	NPC275734
0.8981	High Similarity	NPC200746
0.8981	High Similarity	NPC139036
0.8981	High Similarity	NPC471973
0.8981	High Similarity	NPC320359
0.8981	High Similarity	NPC472902
0.8981	High Similarity	NPC471744
0.8974	High Similarity	NPC217677
0.8974	High Similarity	NPC469584
0.8974	High Similarity	NPC129684
0.8974	High Similarity	NPC84935
0.8974	High Similarity	NPC190020
0.8974	High Similarity	NPC299520
0.8974	High Similarity	NPC165977
0.8974	High Similarity	NPC77679
0.8968	High Similarity	NPC470327
0.8968	High Similarity	NPC45849
0.8968	High Similarity	NPC200761
0.8968	High Similarity	NPC477503
0.8968	High Similarity	NPC57674
0.8968	High Similarity	NPC168247
0.8968	High Similarity	NPC230149
0.8968	High Similarity	NPC152951
0.8968	High Similarity	NPC117992
0.8961	High Similarity	NPC199773
0.8961	High Similarity	NPC257648
0.8961	High Similarity	NPC39007
0.8961	High Similarity	NPC477231
0.8961	High Similarity	NPC161277
0.8961	High Similarity	NPC471982
0.8954	High Similarity	NPC62042
0.8954	High Similarity	NPC470107
0.8954	High Similarity	NPC179183
0.8954	High Similarity	NPC338131
0.8954	High Similarity	NPC96501
0.8954	High Similarity	NPC61620
0.8951	High Similarity	NPC158226
0.8947	High Similarity	NPC321011
0.8947	High Similarity	NPC188679
0.8947	High Similarity	NPC294852
0.8947	High Similarity	NPC3036
0.894	High Similarity	NPC209278
0.8938	High Similarity	NPC29160
0.8933	High Similarity	NPC257025
0.8931	High Similarity	NPC248638
0.8931	High Similarity	NPC234004
0.8931	High Similarity	NPC270837
0.8931	High Similarity	NPC236521
0.8931	High Similarity	NPC236132
0.8931	High Similarity	NPC186686
0.8931	High Similarity	NPC475985
0.8931	High Similarity	NPC152659
0.8931	High Similarity	NPC7483
0.8931	High Similarity	NPC300984
0.8931	High Similarity	NPC220313
0.8931	High Similarity	NPC156082
0.8924	High Similarity	NPC303565
0.8924	High Similarity	NPC112418
0.8917	High Similarity	NPC210459
0.8917	High Similarity	NPC315157
0.8917	High Similarity	NPC45846
0.8917	High Similarity	NPC329091
0.8917	High Similarity	NPC55738
0.8917	High Similarity	NPC85121
0.891	High Similarity	NPC142339
0.891	High Similarity	NPC472626
0.891	High Similarity	NPC235165
0.891	High Similarity	NPC35038
0.891	High Similarity	NPC470328
0.891	High Similarity	NPC278778
0.891	High Similarity	NPC209614
0.891	High Similarity	NPC255106
0.891	High Similarity	NPC195796
0.891	High Similarity	NPC320825
0.891	High Similarity	NPC250922
0.891	High Similarity	NPC326037
0.891	High Similarity	NPC291878
0.891	High Similarity	NPC13858
0.8903	High Similarity	NPC273462
0.8903	High Similarity	NPC33051
0.8903	High Similarity	NPC70433
0.8903	High Similarity	NPC227337
0.8903	High Similarity	NPC475895
0.8903	High Similarity	NPC49402
0.8896	High Similarity	NPC200740
0.8896	High Similarity	NPC28274
0.8896	High Similarity	NPC117579
0.8896	High Similarity	NPC125062
0.8896	High Similarity	NPC133953
0.8896	High Similarity	NPC50403
0.8896	High Similarity	NPC251110
0.8896	High Similarity	NPC149614
0.8896	High Similarity	NPC252933
0.8896	High Similarity	NPC54394
0.8889	High Similarity	NPC183959
0.8889	High Similarity	NPC233267
0.8889	High Similarity	NPC105512

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 NPC20541 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	398
0.1-0.2	1034
0.2-0.3	1937
0.3-0.4	2573
0.4-0.5	1762
0.5-0.6	934
0.6-0.7	355
0.7-0.8	106
0.8-0.85	34
0.85-0.9	15
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.915	High Similarity	NPD1465	Phase 2
0.9085	High Similarity	NPD1934	Approved
0.8808	High Similarity	NPD1511	Approved
0.8782	High Similarity	NPD2801	Approved
0.8782	High Similarity	NPD2393	Clinical (unspecified phase)
0.875	High Similarity	NPD6232	Discontinued
0.8725	High Similarity	NPD970	Clinical (unspecified phase)
0.8693	High Similarity	NPD1512	Approved
0.8671	High Similarity	NPD4868	Clinical (unspecified phase)
0.8608	High Similarity	NPD3817	Phase 2
0.8598	High Similarity	NPD5844	Phase 1
0.8589	High Similarity	NPD7473	Discontinued
0.8553	High Similarity	NPD3882	Suspended
0.8544	High Similarity	NPD7819	Suspended
0.8528	High Similarity	NPD6168	Clinical (unspecified phase)
0.8528	High Similarity	NPD6166	Phase 2
0.8528	High Similarity	NPD6167	Clinical (unspecified phase)
0.8434	Intermediate Similarity	NPD7074	Phase 3
0.8411	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8411	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8385	Intermediate Similarity	NPD3749	Approved
0.8385	Intermediate Similarity	NPD7075	Discontinued
0.8373	Intermediate Similarity	NPD7054	Approved
0.8355	Intermediate Similarity	NPD1549	Phase 2
0.8323	Intermediate Similarity	NPD7472	Approved
0.8313	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8313	Intermediate Similarity	NPD3818	Discontinued
0.8284	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8247	Intermediate Similarity	NPD3750	Approved
0.8221	Intermediate Similarity	NPD919	Approved
0.8205	Intermediate Similarity	NPD6799	Approved
0.8166	Intermediate Similarity	NPD6797	Phase 2
0.8158	Intermediate Similarity	NPD1510	Phase 2
0.8153	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8133	Intermediate Similarity	NPD1240	Approved
0.8125	Intermediate Similarity	NPD6599	Discontinued
0.8121	Intermediate Similarity	NPD6959	Discontinued
0.8118	Intermediate Similarity	NPD7251	Discontinued
0.8079	Intermediate Similarity	NPD447	Suspended
0.8079	Intermediate Similarity	NPD230	Phase 1
0.8075	Intermediate Similarity	NPD7411	Suspended
0.807	Intermediate Similarity	NPD7808	Phase 3
0.8061	Intermediate Similarity	NPD5494	Approved
0.8059	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8049	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8041	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.8038	Intermediate Similarity	NPD2534	Approved
0.8038	Intermediate Similarity	NPD2533	Approved
0.8038	Intermediate Similarity	NPD2532	Approved
0.8026	Intermediate Similarity	NPD1607	Approved
0.8025	Intermediate Similarity	NPD6801	Discontinued
0.8013	Intermediate Similarity	NPD943	Approved
0.8012	Intermediate Similarity	NPD4380	Phase 2
0.8012	Intermediate Similarity	NPD7199	Phase 2
0.7988	Intermediate Similarity	NPD7768	Phase 2
0.7987	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7987	Intermediate Similarity	NPD1551	Phase 2
0.7976	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7949	Intermediate Similarity	NPD1243	Approved
0.7927	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7922	Intermediate Similarity	NPD3748	Approved
0.7917	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7895	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7895	Intermediate Similarity	NPD1613	Approved
0.7892	Intermediate Similarity	NPD6234	Discontinued
0.7871	Intermediate Similarity	NPD2796	Approved
0.7843	Intermediate Similarity	NPD1933	Approved
0.784	Intermediate Similarity	NPD3226	Approved
0.7826	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7812	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7811	Intermediate Similarity	NPD3926	Phase 2
0.7803	Intermediate Similarity	NPD6559	Discontinued
0.7797	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7785	Intermediate Similarity	NPD4628	Phase 3
0.7785	Intermediate Similarity	NPD1203	Approved
0.7763	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7756	Intermediate Similarity	NPD2935	Discontinued
0.775	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7733	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7716	Intermediate Similarity	NPD5403	Approved
0.7716	Intermediate Similarity	NPD920	Approved
0.7711	Intermediate Similarity	NPD5402	Approved
0.7707	Intermediate Similarity	NPD2346	Discontinued
0.7702	Intermediate Similarity	NPD5401	Approved
0.7697	Intermediate Similarity	NPD37	Approved
0.7692	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD1247	Approved
0.7692	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7688	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7674	Intermediate Similarity	NPD7228	Approved
0.7673	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7669	Intermediate Similarity	NPD1653	Approved
0.7665	Intermediate Similarity	NPD4965	Approved
0.7665	Intermediate Similarity	NPD4967	Phase 2
0.7665	Intermediate Similarity	NPD4966	Approved
0.7643	Intermediate Similarity	NPD6100	Approved
0.7643	Intermediate Similarity	NPD6099	Approved
0.761	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.761	Intermediate Similarity	NPD2800	Approved
0.7593	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7584	Intermediate Similarity	NPD1608	Approved
0.7584	Intermediate Similarity	NPD9717	Approved
0.7572	Intermediate Similarity	NPD3751	Discontinued
0.7544	Intermediate Similarity	NPD5710	Approved
0.7544	Intermediate Similarity	NPD5711	Approved
0.7517	Intermediate Similarity	NPD422	Phase 1
0.7514	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD2344	Approved
0.7468	Intermediate Similarity	NPD2799	Discontinued
0.7468	Intermediate Similarity	NPD3027	Phase 3
0.7467	Intermediate Similarity	NPD9269	Phase 2
0.7453	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7451	Intermediate Similarity	NPD9494	Approved
0.7442	Intermediate Similarity	NPD3787	Discontinued
0.7434	Intermediate Similarity	NPD2797	Approved
0.743	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7423	Intermediate Similarity	NPD7390	Discontinued
0.7419	Intermediate Similarity	NPD3268	Approved
0.7419	Intermediate Similarity	NPD411	Approved
0.7418	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7403	Intermediate Similarity	NPD6832	Phase 2
0.7403	Intermediate Similarity	NPD4287	Approved
0.74	Intermediate Similarity	NPD1610	Phase 2
0.7396	Intermediate Similarity	NPD4288	Approved
0.7389	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7383	Intermediate Similarity	NPD17	Approved
0.7358	Intermediate Similarity	NPD4308	Phase 3
0.7355	Intermediate Similarity	NPD4625	Phase 3
0.7345	Intermediate Similarity	NPD5953	Discontinued
0.7341	Intermediate Similarity	NPD7229	Phase 3
0.7333	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7325	Intermediate Similarity	NPD4060	Phase 1
0.7318	Intermediate Similarity	NPD8312	Approved
0.7318	Intermediate Similarity	NPD8313	Approved
0.7312	Intermediate Similarity	NPD5404	Approved
0.7312	Intermediate Similarity	NPD5408	Approved
0.7312	Intermediate Similarity	NPD5406	Approved
0.7312	Intermediate Similarity	NPD5405	Approved
0.7308	Intermediate Similarity	NPD3764	Approved
0.7308	Intermediate Similarity	NPD2313	Discontinued
0.7303	Intermediate Similarity	NPD7685	Pre-registration
0.7301	Intermediate Similarity	NPD2309	Approved
0.7301	Intermediate Similarity	NPD6190	Approved
0.7299	Intermediate Similarity	NPD5242	Approved
0.7292	Intermediate Similarity	NPD8151	Discontinued
0.729	Intermediate Similarity	NPD4908	Phase 1
0.7273	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD1283	Approved
0.7255	Intermediate Similarity	NPD3225	Approved
0.725	Intermediate Similarity	NPD7033	Discontinued
0.7233	Intermediate Similarity	NPD6651	Approved
0.7232	Intermediate Similarity	NPD7286	Phase 2
0.7216	Intermediate Similarity	NPD7783	Phase 2
0.7216	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD3267	Approved
0.7208	Intermediate Similarity	NPD3266	Approved
0.7207	Intermediate Similarity	NPD7240	Approved
0.72	Intermediate Similarity	NPD9268	Approved
0.7197	Intermediate Similarity	NPD6798	Discontinued
0.7197	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD1296	Phase 2
0.7193	Intermediate Similarity	NPD5353	Approved
0.719	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7182	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7178	Intermediate Similarity	NPD1652	Phase 2
0.7171	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD1201	Approved
0.717	Intermediate Similarity	NPD6355	Discontinued
0.7167	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD7003	Approved
0.7133	Intermediate Similarity	NPD9545	Approved
0.7133	Intermediate Similarity	NPD1548	Phase 1
0.7126	Intermediate Similarity	NPD6273	Approved
0.7114	Intermediate Similarity	NPD9493	Approved
0.7107	Intermediate Similarity	NPD4307	Phase 2
0.7104	Intermediate Similarity	NPD8434	Phase 2
0.7104	Intermediate Similarity	NPD8150	Discontinued
0.7097	Intermediate Similarity	NPD1164	Approved
0.7097	Intermediate Similarity	NPD1470	Approved
0.7086	Intermediate Similarity	NPD8127	Discontinued
0.7079	Intermediate Similarity	NPD7177	Discontinued
0.7078	Intermediate Similarity	NPD4749	Approved
0.7074	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7072	Intermediate Similarity	NPD7549	Discontinued
0.7063	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD5124	Phase 1
0.7059	Intermediate Similarity	NPD1281	Approved
0.7051	Intermediate Similarity	NPD1019	Discontinued
0.7051	Intermediate Similarity	NPD2798	Approved
0.7035	Intermediate Similarity	NPD8455	Phase 2
0.7031	Intermediate Similarity	NPD7435	Discontinued
0.703	Intermediate Similarity	NPD4110	Phase 3
0.703	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD7095	Approved
0.7018	Intermediate Similarity	NPD6385	Approved
0.7018	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD6386	Approved
0.7	Intermediate Similarity	NPD7458	Discontinued

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