NPASS Compound

Structure

CID62952 OpenBabel06191715402D 23 24 0 0 0 0 0 0 0 0999 V2000 -3.4641 1.0000 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 6.0622 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -2.0000 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 4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -0.0000 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 3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 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 -0.0000 -2.0000 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 4.3301 -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 0.8660 -0.5000 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 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 O 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 0.0000 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 14 1 0 0 0 0 2 14 1 0 0 0 0 3 4 2 0 0 0 0 3 5 1 0 0 0 0 4 6 1 0 0 0 0 5 7 2 0 0 0 0 6 15 2 0 0 0 0 7 15 1 0 0 0 0 8 10 1 0 0 0 0 8 14 2 0 0 0 0 9 12 2 0 0 0 0 9 15 1 0 0 0 0 10 16 1 0 0 0 0 11 13 2 0 0 0 0 11 17 1 0 0 0 0 12 18 1 0 0 0 0 13 19 1 0 0 0 0 16 19 2 0 0 0 0 16 20 1 0 0 0 0 17 18 1 0 0 0 0 17 20 2 0 0 0 0 18 21 2 0 0 0 0 19 22 1 0 0 0 0 20 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	308.14
Volume:	340.006
LogP:	5.189
LogD:	3.554
LogS:	-4.646
# Rotatable Bonds:	5
TPSA:	57.53
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.485
Synthetic Accessibility Score:	2.346
Fsp3:	0.15
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:	-4.81
MDCK Permeability:	1.7793261577025987e-05
Pgp-inhibitor:	0.098
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.328
30% Bioavailability (F30%):	0.501

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.082
Plasma Protein Binding (PPB):	100.99490356445312%
Volume Distribution (VD):	0.707
Pgp-substrate:	0.7861223816871643%

ADMET: Metabolism

CYP1A2-inhibitor:	0.968
CYP1A2-substrate:	0.109
CYP2C19-inhibitor:	0.933
CYP2C19-substrate:	0.064
CYP2C9-inhibitor:	0.865
CYP2C9-substrate:	0.952
CYP2D6-inhibitor:	0.819
CYP2D6-substrate:	0.729
CYP3A4-inhibitor:	0.463
CYP3A4-substrate:	0.174

ADMET: Excretion

Clearance (CL):	11.544
Half-life (T1/2):	0.357

ADMET: Toxicity

hERG Blockers:	0.023
Human Hepatotoxicity (H-HT):	0.189
Drug-inuced Liver Injury (DILI):	0.266
AMES Toxicity:	0.317
Rat Oral Acute Toxicity:	0.117
Maximum Recommended Daily Dose:	0.063
Skin Sensitization:	0.92
Carcinogencity:	0.403
Eye Corrosion:	0.004
Eye Irritation:	0.925
Respiratory Toxicity:	0.331

Download Data

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

Natural Product: NPC62952

Natural Product ID:	NPC62952
*Common Name:**	Isocordoin
IUPAC Name:	(E)-1-[2,4-dihydroxy-3-(3-methylbut-2-enyl)phenyl]-3-phenylprop-2-en-1-one
Synonyms:	Isocordoin
Standard InCHIKey:	CHWWSUSAPRACBZ-FMIVXFBMSA-N
Standard InCHI:	InChI=1S/C20H20O3/c1-14(2)8-10-16-19(22)13-11-17(20(16)23)18(21)12-9-15-6-4-3-5-7-15/h3-9,11-13,22-23H,10H2,1-2H3/b12-9+
SMILES:	CC(=CCc1c(O)ccc(c1O)C(=O)/C=C/c1ccccc1)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL460618
PubChem CID:	6251270
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0003467] Linear 1,3-diarylpropanoids [CHEMONTID:0001630] Chalcones and dihydrochalcones [CHEMONTID:0003509] 3-prenylated chalcones

*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
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10654410]
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	n.a.	root	n.a.	PMID[10843587]
NPO23982	Ventilago leiocarpa	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11374975]
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	Roots	n.a.	n.a.	PMID[15568770]
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	n.a.	root	n.a.	PMID[16392664]
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	roots	Hualien Hsien, Taiwan	2003-JUL	PMID[16933887]
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	n.a.	root	n.a.	PMID[16933887]
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	n.a.	root	n.a.	PMID[17951038]
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18175961]
NPO27524	Eugenia hyemalis	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18763827]
NPO27524	Eugenia hyemalis	Species	Myrtaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[18763827]
NPO27799	Agelas dispar	Species	Agelasidae	Eukaryota	n.a.	n.a.	n.a.	PMID[18800848]
NPO13726	Agrobacterium tumefaciens	Species	Rhizobiaceae	Bacteria	n.a.	n.a.	n.a.	PMID[22466953]
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24295087]
NPO13726	Agrobacterium tumefaciens	Species	Rhizobiaceae	Bacteria	n.a.	n.a.	n.a.	PMID[24450804]
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27575476]
NPO27061	Drimys winteri	Species	Winteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[29634269]
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	Roots	n.a.	n.a.	PMID[30298740]
NPO27434	Rabdosia ternifolia	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9182128]
NPO27799	Agelas dispar	Species	Agelasidae	Eukaryota	n.a.	n.a.	n.a.	PMID[9461661]
NPO27799	Agelas dispar	Species	Agelasidae	Eukaryota	n.a.	n.a.	n.a.	PMID[9748394]
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	Roots	n.a.	n.a.	PMID[9868163]
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	n.a.	root	n.a.	Database[Article]
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23982	Ventilago leiocarpa	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23982	Ventilago leiocarpa	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27309	Rubus chroosepalus	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO27309	Rubus chroosepalus	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO27639	Tephrosia viridiflora	Species	Geometridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27393	Artemisia schischkinii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26909	Scalesia baurii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27710	Phora affinis	Species	Phoridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27434	Rabdosia ternifolia	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27654	Phyllospongia lamellosa	Species	Thorectidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23982	Ventilago leiocarpa	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13726	Agrobacterium tumefaciens	Species	Rhizobiaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO27061	Drimys winteri	Species	Winteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27309	Rubus chroosepalus	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27214	Coccinella transversoguttata	Species	Coccinellidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21356.1	Helichrysum arenarium subsp. aucheri	Subspecies	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9880	Ecklonia arborea	Species	Lessoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27524	Eugenia hyemalis	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27799	Agelas dispar	Species	Agelasidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27469	Hygrocybe punicea	Species	Hygrophoraceae	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	5
MIC	4
Others	4

Activity Type	# Activity
Cell Line	5
Organism	8

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT306	Cell Line	PC-3	Homo sapiens	IC50	>	25000.0	nM	PMID[498310]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	IC50	>	25000.0	nM	PMID[498310]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	25000.0	nM	PMID[498310]
NPT461	Cell Line	PANC-1	Homo sapiens	IC50	>	25000.0	nM	PMID[498310]
NPT1083	Cell Line	A-375	Homo sapiens	IC50	=	23200.0	nM	PMID[498310]
NPT314	Organism	Bacillus cereus	Bacillus cereus	MIC	=	2000.0	ug.mL-1	PMID[498309]
NPT314	Organism	Bacillus cereus	Bacillus cereus	MBC	=	2000.0	ug ml-1	PMID[498309]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	=	2000.0	ug.mL-1	PMID[498309]
NPT19	Organism	Escherichia coli	Escherichia coli	MBC	=	2000.0	ug ml-1	PMID[498309]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	MIC	=	2000.0	ug.mL-1	PMID[498309]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	MBC	=	1000.0	ug ml-1	PMID[498309]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	2000.0	ug.mL-1	PMID[498309]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MBC	=	2000.0	ug ml-1	PMID[498309]

☑ 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 NPC62952 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	320
0.1-0.2	1575
0.2-0.3	3982
0.3-0.4	11789
0.4-0.5	7242
0.5-0.6	5286
0.6-0.7	6524
0.7-0.8	4599
0.8-0.85	867
0.85-0.9	383
0.9-0.95	103
0.95-1	27

Similarity Score	Similarity Level	Natural Product ID
0.9917	High Similarity	NPC30501
0.9917	High Similarity	NPC266689
0.9917	High Similarity	NPC23126
0.9917	High Similarity	NPC72158
0.9917	High Similarity	NPC190043
0.9917	High Similarity	NPC103356
0.9917	High Similarity	NPC105157
0.9917	High Similarity	NPC98254
0.9917	High Similarity	NPC169250
0.9917	High Similarity	NPC162612
0.9917	High Similarity	NPC100067
0.9835	High Similarity	NPC21305
0.9835	High Similarity	NPC221777
0.9835	High Similarity	NPC473017
0.9833	High Similarity	NPC267846
0.9754	High Similarity	NPC474998
0.9752	High Similarity	NPC116513
0.9664	High Similarity	NPC309765
0.9597	High Similarity	NPC475042
0.958	High Similarity	NPC156139
0.958	High Similarity	NPC303737
0.95	High Similarity	NPC133909
0.95	High Similarity	NPC32032
0.95	High Similarity	NPC91105
0.9496	High Similarity	NPC297186
0.9444	High Similarity	NPC139074
0.9444	High Similarity	NPC40524
0.9444	High Similarity	NPC213485
0.9435	High Similarity	NPC476119
0.9421	High Similarity	NPC65761
0.9421	High Similarity	NPC472029
0.9417	High Similarity	NPC143427
0.9417	High Similarity	NPC45438
0.9417	High Similarity	NPC196976
0.9417	High Similarity	NPC115159
0.9417	High Similarity	NPC224273
0.9417	High Similarity	NPC242895
0.9417	High Similarity	NPC19174
0.9417	High Similarity	NPC73532
0.9417	High Similarity	NPC215392
0.9417	High Similarity	NPC267552
0.937	High Similarity	NPC282780
0.937	High Similarity	NPC166480
0.9333	High Similarity	NPC149246
0.9328	High Similarity	NPC161617
0.9328	High Similarity	NPC188814
0.9328	High Similarity	NPC195262
0.9297	High Similarity	NPC283590
0.9297	High Similarity	NPC61153
0.9297	High Similarity	NPC70859
0.9297	High Similarity	NPC470210
0.9297	High Similarity	NPC130899
0.9286	High Similarity	NPC275504
0.928	High Similarity	NPC92624
0.9268	High Similarity	NPC475733
0.925	High Similarity	NPC159525
0.9225	High Similarity	NPC131039
0.9225	High Similarity	NPC65005
0.9225	High Similarity	NPC194764
0.9225	High Similarity	NPC264112
0.9213	High Similarity	NPC175738
0.9206	High Similarity	NPC259942
0.9194	High Similarity	NPC8745
0.9187	High Similarity	NPC13238
0.9174	High Similarity	NPC229649
0.9167	High Similarity	NPC158222
0.916	High Similarity	NPC121259
0.9154	High Similarity	NPC168105
0.9154	High Similarity	NPC477243
0.9154	High Similarity	NPC150399
0.9154	High Similarity	NPC98115
0.9154	High Similarity	NPC1486
0.9154	High Similarity	NPC25287
0.9154	High Similarity	NPC477244
0.9154	High Similarity	NPC249606
0.9154	High Similarity	NPC477242
0.9154	High Similarity	NPC12165
0.9154	High Similarity	NPC274109
0.9154	High Similarity	NPC186838
0.9154	High Similarity	NPC41461
0.9154	High Similarity	NPC66349
0.9127	High Similarity	NPC109123
0.9113	High Similarity	NPC10926
0.9098	High Similarity	NPC226275
0.9091	High Similarity	NPC294037
0.9084	High Similarity	NPC472419
0.9084	High Similarity	NPC317119
0.9084	High Similarity	NPC153979
0.9083	High Similarity	NPC40649
0.9083	High Similarity	NPC209486
0.9077	High Similarity	NPC156092
0.9077	High Similarity	NPC13575
0.907	High Similarity	NPC475088
0.9024	High Similarity	NPC232708
0.9016	High Similarity	NPC146642
0.9015	High Similarity	NPC242994
0.9015	High Similarity	NPC112789
0.9015	High Similarity	NPC19622
0.9015	High Similarity	NPC21350
0.9015	High Similarity	NPC138099
0.9008	High Similarity	NPC474110
0.9008	High Similarity	NPC44960
0.9	High Similarity	NPC103842
0.9	High Similarity	NPC286336
0.8976	High Similarity	NPC120488
0.8976	High Similarity	NPC102829
0.896	High Similarity	NPC477454
0.8947	High Similarity	NPC181560
0.8947	High Similarity	NPC470211
0.8947	High Similarity	NPC472366
0.8947	High Similarity	NPC477956
0.8947	High Similarity	NPC275903
0.8947	High Similarity	NPC169452
0.8931	High Similarity	NPC191976
0.8931	High Similarity	NPC118919
0.8923	High Similarity	NPC192304
0.8923	High Similarity	NPC144051
0.8923	High Similarity	NPC139813
0.8923	High Similarity	NPC27643
0.8923	High Similarity	NPC82225
0.8923	High Similarity	NPC337373
0.8923	High Similarity	NPC20560
0.8923	High Similarity	NPC28753
0.8923	High Similarity	NPC159623
0.8923	High Similarity	NPC175098
0.8923	High Similarity	NPC188646
0.8923	High Similarity	NPC18877
0.8923	High Similarity	NPC56031
0.8923	High Similarity	NPC294593
0.8923	High Similarity	NPC204960
0.8923	High Similarity	NPC242294
0.8923	High Similarity	NPC312318
0.8923	High Similarity	NPC263670
0.8923	High Similarity	NPC472365
0.8915	High Similarity	NPC313618
0.8915	High Similarity	NPC308037
0.8915	High Similarity	NPC64359
0.8915	High Similarity	NPC262359
0.8908	High Similarity	NPC276111
0.8908	High Similarity	NPC118288
0.8889	High Similarity	NPC328983
0.8889	High Similarity	NPC473691
0.8881	High Similarity	NPC219917
0.8881	High Similarity	NPC144118
0.8881	High Similarity	NPC235239
0.8881	High Similarity	NPC259166
0.8881	High Similarity	NPC80962
0.8881	High Similarity	NPC213659
0.8881	High Similarity	NPC326109
0.8881	High Similarity	NPC172250
0.8881	High Similarity	NPC475680
0.8881	High Similarity	NPC204985
0.8881	High Similarity	NPC172986
0.8881	High Similarity	NPC270883
0.8881	High Similarity	NPC48624
0.8881	High Similarity	NPC305355
0.8881	High Similarity	NPC215311
0.8881	High Similarity	NPC11056
0.8881	High Similarity	NPC261227
0.8881	High Similarity	NPC69769
0.8872	High Similarity	NPC251681
0.8872	High Similarity	NPC471620
0.8872	High Similarity	NPC243528
0.8864	High Similarity	NPC213603
0.8864	High Similarity	NPC53414
0.8864	High Similarity	NPC290030
0.8864	High Similarity	NPC471905
0.8864	High Similarity	NPC53206
0.8862	High Similarity	NPC248363
0.8846	High Similarity	NPC87231
0.8846	High Similarity	NPC129132
0.8846	High Similarity	NPC205468
0.8846	High Similarity	NPC212631
0.8846	High Similarity	NPC267205
0.8846	High Similarity	NPC257756
0.8824	High Similarity	NPC242136
0.8819	High Similarity	NPC316625
0.8819	High Similarity	NPC329205
0.8815	High Similarity	NPC321980
0.8815	High Similarity	NPC156590
0.8815	High Similarity	NPC55832
0.8815	High Similarity	NPC470089
0.8815	High Similarity	NPC26051
0.8815	High Similarity	NPC469404
0.8815	High Similarity	NPC268204
0.8815	High Similarity	NPC470087
0.8815	High Similarity	NPC205006
0.8815	High Similarity	NPC110969
0.8815	High Similarity	NPC118840
0.8815	High Similarity	NPC52789
0.8815	High Similarity	NPC193555
0.8815	High Similarity	NPC147688
0.8815	High Similarity	NPC64908
0.8806	High Similarity	NPC283429
0.8806	High Similarity	NPC220062
0.8806	High Similarity	NPC301217
0.8806	High Similarity	NPC55018
0.8806	High Similarity	NPC96565
0.8806	High Similarity	NPC216978
0.8806	High Similarity	NPC295384

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 NPC62952 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	323
0.1-0.2	966
0.2-0.3	1333
0.3-0.4	2784
0.4-0.5	2106
0.5-0.6	1147
0.6-0.7	360
0.7-0.8	116
0.8-0.85	10
0.85-0.9	5
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8915	High Similarity	NPD1240	Approved
0.8788	High Similarity	NPD1509	Clinical (unspecified phase)
0.8779	High Similarity	NPD1607	Approved
0.8769	High Similarity	NPD943	Approved
0.8507	High Similarity	NPD1510	Phase 2
0.8489	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8489	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8417	Intermediate Similarity	NPD7390	Discontinued
0.8372	Intermediate Similarity	NPD1164	Approved
0.8321	Intermediate Similarity	NPD1549	Phase 2
0.8254	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.8248	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8248	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8203	Intermediate Similarity	NPD1201	Approved
0.8194	Intermediate Similarity	NPD4380	Phase 2
0.8175	Intermediate Similarity	NPD2796	Approved
0.8138	Intermediate Similarity	NPD7411	Suspended
0.8092	Intermediate Similarity	NPD1470	Approved
0.8043	Intermediate Similarity	NPD2935	Discontinued
0.8043	Intermediate Similarity	NPD5405	Approved
0.8043	Intermediate Similarity	NPD5404	Approved
0.8043	Intermediate Similarity	NPD5408	Approved
0.8043	Intermediate Similarity	NPD5406	Approved
0.8027	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7987	Intermediate Similarity	NPD7075	Discontinued
0.7973	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7971	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7956	Intermediate Similarity	NPD6651	Approved
0.7951	Intermediate Similarity	NPD74	Approved
0.7951	Intermediate Similarity	NPD9266	Approved
0.7905	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7905	Intermediate Similarity	NPD7819	Suspended
0.7902	Intermediate Similarity	NPD6799	Approved
0.7899	Intermediate Similarity	NPD940	Approved
0.7899	Intermediate Similarity	NPD846	Approved
0.7874	Intermediate Similarity	NPD9493	Approved
0.7869	Intermediate Similarity	NPD9263	Approved
0.7869	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7869	Intermediate Similarity	NPD9267	Approved
0.7869	Intermediate Similarity	NPD9264	Approved
0.7838	Intermediate Similarity	NPD6801	Discontinued
0.7778	Intermediate Similarity	NPD1511	Approved
0.7746	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7746	Intermediate Similarity	NPD2800	Approved
0.7746	Intermediate Similarity	NPD1243	Approved
0.7734	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.773	Intermediate Similarity	NPD2344	Approved
0.7718	Intermediate Similarity	NPD1934	Approved
0.7714	Intermediate Similarity	NPD2799	Discontinued
0.7703	Intermediate Similarity	NPD6599	Discontinued
0.7692	Intermediate Similarity	NPD3750	Approved
0.7682	Intermediate Similarity	NPD7768	Phase 2
0.7682	Intermediate Similarity	NPD3882	Suspended
0.7677	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7676	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7671	Intermediate Similarity	NPD1512	Approved
0.7667	Intermediate Similarity	NPD2801	Approved
0.7632	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.763	Intermediate Similarity	NPD2798	Approved
0.7615	Intermediate Similarity	NPD9545	Approved
0.7569	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7556	Intermediate Similarity	NPD1203	Approved
0.7548	Intermediate Similarity	NPD6232	Discontinued
0.7541	Intermediate Similarity	NPD9261	Approved
0.7536	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7535	Intermediate Similarity	NPD1551	Phase 2
0.7517	Intermediate Similarity	NPD2309	Approved
0.7516	Intermediate Similarity	NPD3749	Approved
0.7516	Intermediate Similarity	NPD7473	Discontinued
0.7484	Intermediate Similarity	NPD6959	Discontinued
0.7483	Intermediate Similarity	NPD2532	Approved
0.7483	Intermediate Similarity	NPD2533	Approved
0.7483	Intermediate Similarity	NPD2534	Approved
0.7479	Intermediate Similarity	NPD2859	Approved
0.7479	Intermediate Similarity	NPD2860	Approved
0.7466	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7463	Intermediate Similarity	NPD9269	Phase 2
0.7463	Intermediate Similarity	NPD3972	Approved
0.7442	Intermediate Similarity	NPD9281	Approved
0.7438	Intermediate Similarity	NPD5953	Discontinued
0.7424	Intermediate Similarity	NPD9268	Approved
0.7421	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7421	Intermediate Similarity	NPD7286	Phase 2
0.7421	Intermediate Similarity	NPD6020	Phase 2
0.741	Intermediate Similarity	NPD2313	Discontinued
0.7395	Intermediate Similarity	NPD2933	Approved
0.7395	Intermediate Similarity	NPD2934	Approved
0.7383	Intermediate Similarity	NPD920	Approved
0.7377	Intermediate Similarity	NPD1242	Phase 1
0.7365	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7343	Intermediate Similarity	NPD3748	Approved
0.7342	Intermediate Similarity	NPD6166	Phase 2
0.7342	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7342	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD9717	Approved
0.7323	Intermediate Similarity	NPD4750	Phase 3
0.7308	Intermediate Similarity	NPD5494	Approved
0.7295	Intermediate Similarity	NPD3020	Approved
0.7286	Intermediate Similarity	NPD3764	Approved
0.7273	Intermediate Similarity	NPD3817	Phase 2
0.7267	Intermediate Similarity	NPD5403	Approved
0.7266	Intermediate Similarity	NPD6832	Phase 2
0.726	Intermediate Similarity	NPD2654	Approved
0.7259	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7254	Intermediate Similarity	NPD230	Phase 1
0.725	Intermediate Similarity	NPD3818	Discontinued
0.7248	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD3019	Approved
0.7239	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD2932	Approved
0.72	Intermediate Similarity	NPD1237	Approved
0.7178	Intermediate Similarity	NPD6559	Discontinued
0.7174	Intermediate Similarity	NPD2797	Approved
0.7172	Intermediate Similarity	NPD6100	Approved
0.7172	Intermediate Similarity	NPD6099	Approved
0.7171	Intermediate Similarity	NPD3226	Approved
0.7163	Intermediate Similarity	NPD3268	Approved
0.716	Intermediate Similarity	NPD7074	Phase 3
0.7133	Intermediate Similarity	NPD5401	Approved
0.7132	Intermediate Similarity	NPD422	Phase 1
0.7123	Intermediate Similarity	NPD2346	Discontinued
0.712	Intermediate Similarity	NPD1931	Clinical (unspecified phase)
0.712	Intermediate Similarity	NPD1930	Approved
0.712	Intermediate Similarity	NPD1929	Approved
0.7115	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD3300	Phase 2
0.7109	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD7054	Approved
0.7095	Intermediate Similarity	NPD7003	Approved
0.7095	Intermediate Similarity	NPD4628	Phase 3
0.7059	Intermediate Similarity	NPD7458	Discontinued
0.7055	Intermediate Similarity	NPD1729	Discontinued
0.7055	Intermediate Similarity	NPD7472	Approved
0.7049	Intermediate Similarity	NPD1809	Phase 2
0.7045	Intermediate Similarity	NPD5951	Approved
0.7042	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD919	Approved
0.7025	Intermediate Similarity	NPD845	Approved
0.7012	Intermediate Similarity	NPD6797	Phase 2
0.6994	Remote Similarity	NPD5844	Phase 1
0.6993	Remote Similarity	NPD520	Approved
0.6986	Remote Similarity	NPD4308	Phase 3
0.698	Remote Similarity	NPD3400	Discontinued
0.698	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6978	Remote Similarity	NPD1876	Approved
0.697	Remote Similarity	NPD7251	Discontinued
0.6963	Remote Similarity	NPD1548	Phase 1
0.6957	Remote Similarity	NPD3926	Phase 2
0.6943	Remote Similarity	NPD5402	Approved
0.6943	Remote Similarity	NPD8438	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD2296	Approved
0.6937	Remote Similarity	NPD1247	Approved
0.6928	Remote Similarity	NPD7808	Phase 3
0.6901	Remote Similarity	NPD4908	Phase 1
0.6894	Remote Similarity	NPD5711	Approved
0.6894	Remote Similarity	NPD5710	Approved
0.6884	Remote Similarity	NPD1610	Phase 2
0.6871	Remote Similarity	NPD7033	Discontinued
0.6871	Remote Similarity	NPD3299	Clinical (unspecified phase)
0.6853	Remote Similarity	NPD4625	Phase 3
0.6842	Remote Similarity	NPD1241	Discontinued
0.6839	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD1608	Approved
0.6829	Remote Similarity	NPD1432	Clinical (unspecified phase)
0.6826	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD4360	Phase 2
0.6821	Remote Similarity	NPD4363	Phase 3
0.6809	Remote Similarity	NPD3266	Approved
0.6809	Remote Similarity	NPD3267	Approved
0.6806	Remote Similarity	NPD411	Approved
0.6794	Remote Similarity	NPD3021	Approved
0.6794	Remote Similarity	NPD3022	Approved
0.6788	Remote Similarity	NPD1651	Approved
0.6786	Remote Similarity	NPD1755	Approved
0.6782	Remote Similarity	NPD4362	Clinical (unspecified phase)
0.6782	Remote Similarity	NPD4361	Phase 2
0.6781	Remote Similarity	NPD447	Suspended
0.6781	Remote Similarity	NPD1933	Approved
0.6781	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6779	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6779	Remote Similarity	NPD1471	Phase 3
0.6774	Remote Similarity	NPD844	Approved
0.6772	Remote Similarity	NPD1465	Phase 2
0.6767	Remote Similarity	NPD7635	Approved
0.6761	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6755	Remote Similarity	NPD1196	Approved
0.6753	Remote Similarity	NPD5049	Phase 3
0.6752	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6746	Remote Similarity	NPD2066	Phase 3
0.6744	Remote Similarity	NPD5048	Discontinued
0.6741	Remote Similarity	NPD256	Approved
0.6741	Remote Similarity	NPD255	Approved
0.6739	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.6738	Remote Similarity	NPD1283	Approved
0.6738	Remote Similarity	NPD3225	Approved
0.6732	Remote Similarity	NPD1543	Discontinued
0.673	Remote Similarity	NPD4288	Approved
0.6723	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6715	Remote Similarity	NPD1759	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