NPASS Compound

Structure

CID201451 OpenBabel06191715592D 24 26 0 0 0 0 0 0 0 0999 V2000 -4.3301 2.5000 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 -2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 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 -2.5981 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 -1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 1.0000 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 0.0000 -2.0000 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 -0.8660 -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 -0.5000 0.0000 C 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 3.4641 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -3.0000 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 -4.3301 1.5000 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 22 1 0 0 0 0 2 23 1 0 0 0 0 3 5 1 0 0 0 0 3 8 2 0 0 0 0 4 6 2 0 0 0 0 4 8 1 0 0 0 0 5 9 2 0 0 0 0 6 9 1 0 0 0 0 7 10 2 0 0 0 0 7 11 1 0 0 0 0 8 15 1 0 0 0 0 9 22 1 0 0 0 0 10 12 1 0 0 0 0 10 18 1 0 0 0 0 11 16 2 0 0 0 0 11 19 1 0 0 0 0 12 13 1 0 0 0 0 12 17 2 0 0 0 0 13 14 1 0 0 0 0 13 20 2 0 0 0 0 14 15 2 0 0 0 0 14 21 1 0 0 0 0 15 24 1 0 0 0 0 16 17 1 0 0 0 0 16 23 1 0 0 0 0 17 24 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	330.07
Volume:	317.359
LogP:	3.099
LogD:	2.504
LogS:	-3.869
# Rotatable Bonds:	3
TPSA:	109.36
# H-Bond Aceptor:	7
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.677
Synthetic Accessibility Score:	2.441
Fsp3:	0.118
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	2
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.996
MDCK Permeability:	1.4005247066961601e-05
Pgp-inhibitor:	0.996
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.023
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.025

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.005
Plasma Protein Binding (PPB):	93.30615997314453%
Volume Distribution (VD):	0.714
Pgp-substrate:	10.814485549926758%

ADMET: Metabolism

CYP1A2-inhibitor:	0.942
CYP1A2-substrate:	0.887
CYP2C19-inhibitor:	0.334
CYP2C19-substrate:	0.06
CYP2C9-inhibitor:	0.769
CYP2C9-substrate:	0.85
CYP2D6-inhibitor:	0.435
CYP2D6-substrate:	0.324
CYP3A4-inhibitor:	0.365
CYP3A4-substrate:	0.144

ADMET: Excretion

Clearance (CL):	4.513
Half-life (T1/2):	0.798

ADMET: Toxicity

hERG Blockers:	0.019
Human Hepatotoxicity (H-HT):	0.12
Drug-inuced Liver Injury (DILI):	0.986
AMES Toxicity:	0.704
Rat Oral Acute Toxicity:	0.152
Maximum Recommended Daily Dose:	0.047
Skin Sensitization:	0.626
Carcinogencity:	0.126
Eye Corrosion:	0.004
Eye Irritation:	0.828
Respiratory Toxicity:	0.171

Download Data

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

Natural Product: NPC201451

Natural Product ID:	NPC201451
*Common Name:**	Prudomestin
IUPAC Name:	3,5,7-trihydroxy-8-methoxy-2-(4-methoxyphenyl)chromen-4-one
Synonyms:	Prudomestin
Standard InCHIKey:	HLSIOUXODPWHFI-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C17H14O7/c1-22-9-5-3-8(4-6-9)15-14(21)13(20)12-10(18)7-11(19)16(23-2)17(12)24-15/h3-7,18-19,21H,1-2H3
SMILES:	COc1ccc(cc1)c1c(c(=O)c2c(cc(c(c2o1)OC)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL478812
PubChem CID:	10404353
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001615] Flavones [CHEMONTID:0001136] Flavonols

*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
NPO21390	Zanthoxylum integrifoliolum	Species	Rutaceae	Eukaryota	fruit	Lanyu Island, Taitung County, Taiwan	n.a.	PMID[10395498]
NPO25128	Panax vietnamensis	Species	Araliaceae	Eukaryota	n.a.	Vietnamese	n.a.	PMID[11325227]
NPO18950	Cephalotaxus fortunei	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12542368]
NPO22637	Kunzea ambigua	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15043420]
NPO10407	Petromyzon marinus	Species	Petromyzontidae	Eukaryota	n.a.	n.a.	n.a.	PMID[15193266]
NPO21390	Zanthoxylum integrifoliolum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17822293]
NPO18950	Cephalotaxus fortunei	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28139925]
NPO18950	Cephalotaxus fortunei	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31184894]
NPO14951	Zanthoxylum acanthopodium	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18950	Cephalotaxus fortunei	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7142	Corydalis suaveolens	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24672	Helleborus purpurascens	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21390	Zanthoxylum integrifoliolum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14951	Zanthoxylum acanthopodium	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24672	Helleborus purpurascens	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18950	Cephalotaxus fortunei	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7142	Corydalis suaveolens	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18950	Cephalotaxus fortunei	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO25410	Manilkara bidentata	Species	Sapotaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24866	Smilax aspera	Species	Smilacaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24549	Scutellaria cordifrons	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16988	Pseudodistoma novaezelandiae	Species	Pseudodistomidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24735	Cupania latifolia	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21390	Zanthoxylum integrifoliolum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16885	Phonus arborescens	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28771	Clematis delavayi	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25468	Tabernaemontana amygdalifolia	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24821	Nidorella resedifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24672	Helleborus purpurascens	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19721	Impatiens roylei	Species	Balsaminaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18950	Cephalotaxus fortunei	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7142	Corydalis suaveolens	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23489	Stachys anisochila	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25128	Panax vietnamensis	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5676	Annulohypoxylon multiforme	Species	Xylariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22637	Kunzea ambigua	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24591	Trichosanthes dioica	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8943	Juniperus californica	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17249	Lespedeza capitata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25321	Acantholimon glumaceum	Species	Plumbaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25557	Alternaria porri	Species	Pleosporaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14951	Zanthoxylum acanthopodium	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10407	Petromyzon marinus	Species	Petromyzontidae	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	12

Activity Type	# Activity
NON-MOLECULAR	6
Tissue	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT177	Tissue	Aorta	Rattus norvegicus	Activity	=	36.7	%	PMID[558393]
NPT177	Tissue	Aorta	Rattus norvegicus	Activity	=	20.0	%	PMID[558393]
NPT177	Tissue	Aorta	Rattus norvegicus	Activity	=	46.7	%	PMID[558393]
NPT177	Tissue	Aorta	Rattus norvegicus	Activity	=	83.4	%	PMID[558393]
NPT177	Tissue	Aorta	Rattus norvegicus	Activity	=	100.6	%	PMID[558393]
NPT177	Tissue	Aorta	Rattus norvegicus	Activity	=	97.8	%	PMID[558393]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	87.5	%	PMID[558393]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	0.0	%	PMID[558393]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	58.1	%	PMID[558393]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	73.3	%	PMID[558393]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	64.5	%	PMID[558393]

☑ 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 NPC201451 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	480
0.1-0.2	2045
0.2-0.3	5283
0.3-0.4	11455
0.4-0.5	5595
0.5-0.6	4083
0.6-0.7	5142
0.7-0.8	4776
0.8-0.85	1856
0.85-0.9	1104
0.9-0.95	612
0.95-1	266

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC26227
1.0	High Similarity	NPC44079
0.9932	High Similarity	NPC49824
0.9932	High Similarity	NPC245546
0.9932	High Similarity	NPC98661
0.9932	High Similarity	NPC266960
0.9932	High Similarity	NPC247017
0.9932	High Similarity	NPC43243
0.9866	High Similarity	NPC110070
0.9866	High Similarity	NPC75215
0.9866	High Similarity	NPC163524
0.9866	High Similarity	NPC287979
0.9866	High Similarity	NPC189179
0.9866	High Similarity	NPC203891
0.9866	High Similarity	NPC224137
0.9866	High Similarity	NPC101830
0.9866	High Similarity	NPC305663
0.9866	High Similarity	NPC227192
0.9866	High Similarity	NPC176665
0.9866	High Similarity	NPC93376
0.9864	High Similarity	NPC301123
0.9864	High Similarity	NPC25270
0.9864	High Similarity	NPC275836
0.9864	High Similarity	NPC198826
0.9864	High Similarity	NPC100887
0.9864	High Similarity	NPC293183
0.9864	High Similarity	NPC212678
0.9864	High Similarity	NPC187498
0.9864	High Similarity	NPC57030
0.9864	High Similarity	NPC120163
0.9864	High Similarity	NPC131624
0.9864	High Similarity	NPC156222
0.9864	High Similarity	NPC222830
0.9864	High Similarity	NPC241498
0.9864	High Similarity	NPC162313
0.9864	High Similarity	NPC83508
0.9864	High Similarity	NPC71334
0.9864	High Similarity	NPC188203
0.9864	High Similarity	NPC301323
0.9864	High Similarity	NPC239128
0.9864	High Similarity	NPC256283
0.9864	High Similarity	NPC275722
0.98	High Similarity	NPC261004
0.98	High Similarity	NPC22472
0.98	High Similarity	NPC152166
0.98	High Similarity	NPC176300
0.98	High Similarity	NPC105242
0.98	High Similarity	NPC4481
0.98	High Similarity	NPC288669
0.98	High Similarity	NPC7846
0.98	High Similarity	NPC18607
0.98	High Similarity	NPC25495
0.98	High Similarity	NPC9609
0.98	High Similarity	NPC115798
0.98	High Similarity	NPC18772
0.98	High Similarity	NPC143828
0.98	High Similarity	NPC191459
0.98	High Similarity	NPC19687
0.98	High Similarity	NPC204854
0.98	High Similarity	NPC130894
0.98	High Similarity	NPC253634
0.98	High Similarity	NPC300943
0.9799	High Similarity	NPC474520
0.9799	High Similarity	NPC292107
0.9797	High Similarity	NPC231018
0.9797	High Similarity	NPC86485
0.9797	High Similarity	NPC47781
0.9797	High Similarity	NPC255350
0.9797	High Similarity	NPC22519
0.9797	High Similarity	NPC160951
0.9797	High Similarity	NPC69394
0.9797	High Similarity	NPC274327
0.9797	High Similarity	NPC183878
0.9797	High Similarity	NPC145379
0.9797	High Similarity	NPC176775
0.9796	High Similarity	NPC225731
0.9796	High Similarity	NPC54394
0.9796	High Similarity	NPC200740
0.9796	High Similarity	NPC125062
0.9796	High Similarity	NPC252933
0.9733	High Similarity	NPC472438
0.9733	High Similarity	NPC78302
0.9733	High Similarity	NPC235215
0.9733	High Similarity	NPC7973
0.9733	High Similarity	NPC29841
0.9732	High Similarity	NPC167815
0.9732	High Similarity	NPC201136
0.9732	High Similarity	NPC50715
0.9732	High Similarity	NPC2476
0.9732	High Similarity	NPC92659
0.9732	High Similarity	NPC163780
0.9732	High Similarity	NPC138360
0.9732	High Similarity	NPC280339
0.9732	High Similarity	NPC189960
0.9732	High Similarity	NPC256612
0.9732	High Similarity	NPC128863
0.9732	High Similarity	NPC227325
0.9732	High Similarity	NPC213622
0.9732	High Similarity	NPC146165
0.9732	High Similarity	NPC32557
0.9732	High Similarity	NPC20830
0.9732	High Similarity	NPC183597
0.9732	High Similarity	NPC4455
0.9732	High Similarity	NPC214138
0.9732	High Similarity	NPC196439
0.973	High Similarity	NPC82325
0.973	High Similarity	NPC142540
0.973	High Similarity	NPC55205
0.973	High Similarity	NPC279989
0.973	High Similarity	NPC27208
0.9728	High Similarity	NPC306821
0.9728	High Similarity	NPC184136
0.9669	High Similarity	NPC193842
0.9667	High Similarity	NPC55619
0.9667	High Similarity	NPC178854
0.9667	High Similarity	NPC265511
0.9667	High Similarity	NPC200388
0.9667	High Similarity	NPC268161
0.9667	High Similarity	NPC100916
0.9664	High Similarity	NPC179126
0.9664	High Similarity	NPC270620
0.9664	High Similarity	NPC236223
0.9664	High Similarity	NPC78326
0.9664	High Similarity	NPC75279
0.9664	High Similarity	NPC250822
0.9664	High Similarity	NPC276409
0.9662	High Similarity	NPC226973
0.9662	High Similarity	NPC28274
0.9662	High Similarity	NPC133953
0.9662	High Similarity	NPC208043
0.9662	High Similarity	NPC50403
0.966	High Similarity	NPC259713
0.966	High Similarity	NPC270465
0.966	High Similarity	NPC216318
0.966	High Similarity	NPC159103
0.966	High Similarity	NPC183950
0.966	High Similarity	NPC287101
0.966	High Similarity	NPC296197
0.966	High Similarity	NPC52005
0.966	High Similarity	NPC137062
0.966	High Similarity	NPC87125
0.966	High Similarity	NPC17286
0.966	High Similarity	NPC223579
0.966	High Similarity	NPC195351
0.9605	High Similarity	NPC246478
0.9605	High Similarity	NPC263449
0.9603	High Similarity	NPC470402
0.96	High Similarity	NPC208197
0.96	High Similarity	NPC2928
0.9597	High Similarity	NPC199100
0.9597	High Similarity	NPC39732
0.9597	High Similarity	NPC120537
0.9597	High Similarity	NPC123886
0.9597	High Similarity	NPC180234
0.9597	High Similarity	NPC60972
0.9597	High Similarity	NPC134677
0.9595	High Similarity	NPC50728
0.9595	High Similarity	NPC188871
0.9595	High Similarity	NPC166753
0.9595	High Similarity	NPC77858
0.9595	High Similarity	NPC286342
0.9595	High Similarity	NPC149127
0.9595	High Similarity	NPC45873
0.9592	High Similarity	NPC120464
0.9542	High Similarity	NPC308992
0.9539	High Similarity	NPC195832
0.9539	High Similarity	NPC152904
0.9536	High Similarity	NPC472916
0.9536	High Similarity	NPC255106
0.9536	High Similarity	NPC235165
0.9533	High Similarity	NPC246204
0.9533	High Similarity	NPC206238
0.9533	High Similarity	NPC292214
0.9533	High Similarity	NPC88645
0.9533	High Similarity	NPC58382
0.9533	High Similarity	NPC167091
0.9533	High Similarity	NPC162351
0.9533	High Similarity	NPC271779
0.953	High Similarity	NPC260895
0.953	High Similarity	NPC308451
0.953	High Similarity	NPC236769
0.953	High Similarity	NPC117579
0.9527	High Similarity	NPC48479
0.9527	High Similarity	NPC177298
0.9527	High Similarity	NPC328119
0.9524	High Similarity	NPC30647
0.9524	High Similarity	NPC61871
0.9524	High Similarity	NPC55557
0.9524	High Similarity	NPC12200
0.9524	High Similarity	NPC275772
0.9524	High Similarity	NPC108406
0.9524	High Similarity	NPC239312
0.9524	High Similarity	NPC130230
0.9477	High Similarity	NPC476980
0.9474	High Similarity	NPC472910
0.9474	High Similarity	NPC474836
0.9474	High Similarity	NPC78225
0.9474	High Similarity	NPC472913
0.9474	High Similarity	NPC222814
0.9474	High Similarity	NPC48208

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 NPC201451 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	450
0.1-0.2	1006
0.2-0.3	1906
0.3-0.4	2679
0.4-0.5	1673
0.5-0.6	954
0.6-0.7	332
0.7-0.8	96
0.8-0.85	34
0.85-0.9	11
0.9-0.95	6
0.95-1	3

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9797	High Similarity	NPD2801	Approved
0.9456	High Similarity	NPD1512	Approved
0.9338	High Similarity	NPD1934	Approved
0.932	High Similarity	NPD1511	Approved
0.9281	High Similarity	NPD3882	Suspended
0.9091	High Similarity	NPD3817	Phase 2
0.9026	High Similarity	NPD2393	Clinical (unspecified phase)
0.8994	High Similarity	NPD6168	Clinical (unspecified phase)
0.8994	High Similarity	NPD6167	Clinical (unspecified phase)
0.8994	High Similarity	NPD6166	Phase 2
0.8957	High Similarity	NPD4338	Clinical (unspecified phase)
0.8874	High Similarity	NPD4378	Clinical (unspecified phase)
0.8765	High Similarity	NPD3818	Discontinued
0.872	High Similarity	NPD6797	Phase 2
0.8712	High Similarity	NPD7054	Approved
0.8667	High Similarity	NPD7251	Discontinued
0.8659	High Similarity	NPD7472	Approved
0.8614	High Similarity	NPD7808	Phase 3
0.8545	High Similarity	NPD7074	Phase 3
0.8509	High Similarity	NPD5494	Approved
0.8491	Intermediate Similarity	NPD5402	Approved
0.8457	Intermediate Similarity	NPD1247	Approved
0.8442	Intermediate Similarity	NPD6799	Approved
0.8438	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8411	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8411	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.84	Intermediate Similarity	NPD1510	Phase 2
0.8385	Intermediate Similarity	NPD7075	Discontinued
0.8355	Intermediate Similarity	NPD1549	Phase 2
0.8354	Intermediate Similarity	NPD4380	Phase 2
0.8313	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8293	Intermediate Similarity	NPD6232	Discontinued
0.8272	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8255	Intermediate Similarity	NPD943	Approved
0.8255	Intermediate Similarity	NPD1240	Approved
0.8253	Intermediate Similarity	NPD7473	Discontinued
0.825	Intermediate Similarity	NPD6801	Discontinued
0.8224	Intermediate Similarity	NPD2796	Approved
0.8199	Intermediate Similarity	NPD1465	Phase 2
0.8166	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8155	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8153	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8146	Intermediate Similarity	NPD1607	Approved
0.8133	Intermediate Similarity	NPD3926	Phase 2
0.8125	Intermediate Similarity	NPD6599	Discontinued
0.8117	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.811	Intermediate Similarity	NPD919	Approved
0.805	Intermediate Similarity	NPD5403	Approved
0.8047	Intermediate Similarity	NPD5844	Phase 1
0.8039	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.8038	Intermediate Similarity	NPD5401	Approved
0.7987	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7975	Intermediate Similarity	NPD7819	Suspended
0.7961	Intermediate Similarity	NPD230	Phase 1
0.7961	Intermediate Similarity	NPD447	Suspended
0.7927	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7919	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7898	Intermediate Similarity	NPD3750	Approved
0.7895	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7895	Intermediate Similarity	NPD1613	Approved
0.7871	Intermediate Similarity	NPD2935	Discontinued
0.7853	Intermediate Similarity	NPD7411	Suspended
0.7834	Intermediate Similarity	NPD2800	Approved
0.7798	Intermediate Similarity	NPD6959	Discontinued
0.7778	Intermediate Similarity	NPD3751	Discontinued
0.7756	Intermediate Similarity	NPD1551	Phase 2
0.7736	Intermediate Similarity	NPD6190	Approved
0.7725	Intermediate Similarity	NPD3749	Approved
0.7716	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7701	Intermediate Similarity	NPD6559	Discontinued
0.7697	Intermediate Similarity	NPD3027	Phase 3
0.7682	Intermediate Similarity	NPD9494	Approved
0.7673	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7669	Intermediate Similarity	NPD1653	Approved
0.7647	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD3787	Discontinued
0.7613	Intermediate Similarity	NPD1933	Approved
0.7607	Intermediate Similarity	NPD920	Approved
0.7602	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7598	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7595	Intermediate Similarity	NPD2344	Approved
0.7593	Intermediate Similarity	NPD2534	Approved
0.7593	Intermediate Similarity	NPD2532	Approved
0.7593	Intermediate Similarity	NPD2533	Approved
0.758	Intermediate Similarity	NPD3748	Approved
0.756	Intermediate Similarity	NPD7768	Phase 2
0.7558	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7533	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD2313	Discontinued
0.7531	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7528	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD3226	Approved
0.7514	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1243	Approved
0.7485	Intermediate Similarity	NPD7199	Phase 2
0.7485	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7471	Intermediate Similarity	NPD6234	Discontinued
0.7468	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7453	Intermediate Similarity	NPD4628	Phase 3
0.7434	Intermediate Similarity	NPD1203	Approved
0.7421	Intermediate Similarity	NPD6100	Approved
0.7421	Intermediate Similarity	NPD6099	Approved
0.7419	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD2309	Approved
0.7375	Intermediate Similarity	NPD2346	Discontinued
0.7372	Intermediate Similarity	NPD6233	Phase 2
0.7365	Intermediate Similarity	NPD1548	Phase 1
0.7362	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.736	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD2799	Discontinued
0.7351	Intermediate Similarity	NPD9269	Phase 2
0.7345	Intermediate Similarity	NPD5953	Discontinued
0.7342	Intermediate Similarity	NPD6651	Approved
0.733	Intermediate Similarity	NPD7286	Phase 2
0.7303	Intermediate Similarity	NPD7685	Pre-registration
0.7293	Intermediate Similarity	NPD8434	Phase 2
0.7285	Intermediate Similarity	NPD422	Phase 1
0.7278	Intermediate Similarity	NPD6844	Discontinued
0.7278	Intermediate Similarity	NPD37	Approved
0.7278	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7258	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7257	Intermediate Similarity	NPD2403	Approved
0.7251	Intermediate Similarity	NPD4966	Approved
0.7251	Intermediate Similarity	NPD4967	Phase 2
0.7251	Intermediate Similarity	NPD4965	Approved
0.7237	Intermediate Similarity	NPD9717	Approved
0.7234	Intermediate Similarity	NPD6776	Approved
0.7234	Intermediate Similarity	NPD6781	Approved
0.7234	Intermediate Similarity	NPD6782	Approved
0.7234	Intermediate Similarity	NPD6780	Approved
0.7234	Intermediate Similarity	NPD6777	Approved
0.7234	Intermediate Similarity	NPD6778	Approved
0.7234	Intermediate Similarity	NPD6779	Approved
0.7212	Intermediate Similarity	NPD7390	Discontinued
0.72	Intermediate Similarity	NPD5242	Approved
0.7197	Intermediate Similarity	NPD6798	Discontinued
0.7197	Intermediate Similarity	NPD3268	Approved
0.7179	Intermediate Similarity	NPD4908	Phase 1
0.7179	Intermediate Similarity	NPD6832	Phase 2
0.7175	Intermediate Similarity	NPD7228	Approved
0.7171	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD1610	Phase 2
0.7161	Intermediate Similarity	NPD2798	Approved
0.7143	Intermediate Similarity	NPD7033	Discontinued
0.7143	Intermediate Similarity	NPD4308	Phase 3
0.7143	Intermediate Similarity	NPD3225	Approved
0.7134	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD1608	Approved
0.712	Intermediate Similarity	NPD7435	Discontinued
0.7118	Intermediate Similarity	NPD6385	Approved
0.7118	Intermediate Similarity	NPD6386	Approved
0.7115	Intermediate Similarity	NPD3018	Phase 2
0.7108	Intermediate Similarity	NPD4357	Discontinued
0.7104	Intermediate Similarity	NPD8150	Discontinued
0.7097	Intermediate Similarity	NPD2797	Approved
0.7093	Intermediate Similarity	NPD5353	Approved
0.7091	Intermediate Similarity	NPD2354	Approved
0.7089	Intermediate Similarity	NPD411	Approved
0.7089	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD9268	Approved
0.7073	Intermediate Similarity	NPD2654	Approved
0.7067	Intermediate Similarity	NPD5536	Phase 2
0.7066	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD6355	Discontinued
0.7062	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD4360	Phase 2
0.7059	Intermediate Similarity	NPD4363	Phase 3
0.7055	Intermediate Similarity	NPD1471	Phase 3
0.7045	Intermediate Similarity	NPD5711	Approved
0.7045	Intermediate Similarity	NPD5710	Approved
0.7033	Intermediate Similarity	NPD8312	Approved
0.7033	Intermediate Similarity	NPD8313	Approved
0.7031	Intermediate Similarity	NPD7696	Phase 3
0.7031	Intermediate Similarity	NPD7698	Approved
0.7031	Intermediate Similarity	NPD7697	Approved
0.7024	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD1481	Phase 2
0.7007	Intermediate Similarity	NPD228	Approved
0.7006	Intermediate Similarity	NPD2861	Phase 2
0.7	Intermediate Similarity	NPD4060	Phase 1
0.6995	Remote Similarity	NPD7870	Phase 2
0.6995	Remote Similarity	NPD7871	Phase 2
0.6994	Remote Similarity	NPD4288	Approved
0.6987	Remote Similarity	NPD1470	Approved
0.6987	Remote Similarity	NPD3266	Approved
0.6987	Remote Similarity	NPD3267	Approved
0.6983	Remote Similarity	NPD2163	Approved
0.6978	Remote Similarity	NPD7549	Discontinued
0.6974	Remote Similarity	NPD7701	Phase 2
0.697	Remote Similarity	NPD1652	Phase 2
0.6968	Remote Similarity	NPD2983	Phase 2
0.6968	Remote Similarity	NPD6534	Approved
0.6968	Remote Similarity	NPD6535	Approved
0.6968	Remote Similarity	NPD2982	Phase 2
0.6965	Remote Similarity	NPD2899	Discontinued
0.6964	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6949	Remote Similarity	NPD7229	Phase 3
0.6948	Remote Similarity	NPD1201	Approved
0.6948	Remote Similarity	NPD1535	Discovery

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