NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	205.07
Volume:	205.885
LogP:	1.589
LogD:	1.432
LogS:	-2.66
# Rotatable Bonds:	2
TPSA:	51.32
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.809
Synthetic Accessibility Score:	2.061
Fsp3:	0.182
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.874
MDCK Permeability:	1.5072836504259612e-05
Pgp-inhibitor:	0.002
Pgp-substrate:	0.105
Human Intestinal Absorption (HIA):	0.01
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.031

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.845
Plasma Protein Binding (PPB):	51.702552795410156%
Volume Distribution (VD):	0.748
Pgp-substrate:	29.829729080200195%

ADMET: Metabolism

CYP1A2-inhibitor:	0.965
CYP1A2-substrate:	0.97
CYP2C19-inhibitor:	0.386
CYP2C19-substrate:	0.716
CYP2C9-inhibitor:	0.128
CYP2C9-substrate:	0.807
CYP2D6-inhibitor:	0.08
CYP2D6-substrate:	0.778
CYP3A4-inhibitor:	0.248
CYP3A4-substrate:	0.413

ADMET: Excretion

Clearance (CL):	7.196
Half-life (T1/2):	0.78

ADMET: Toxicity

hERG Blockers:	0.034
Human Hepatotoxicity (H-HT):	0.298
Drug-inuced Liver Injury (DILI):	0.914
AMES Toxicity:	0.792
Rat Oral Acute Toxicity:	0.49
Maximum Recommended Daily Dose:	0.04
Skin Sensitization:	0.291
Carcinogencity:	0.587
Eye Corrosion:	0.033
Eye Irritation:	0.776
Respiratory Toxicity:	0.969

Download Data

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

Natural Product: NPC42591

Natural Product ID:	NPC42591
*Common Name:**	Edulitine
IUPAC Name:	4,8-dimethoxy-1H-quinolin-2-one
Synonyms:	Edulitine
Standard InCHIKey:	HPPSTURWGYFXQN-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C11H11NO3/c1-14-8-5-3-4-7-9(15-2)6-10(13)12-11(7)8/h3-6H,1-2H3,(H,12,13)
SMILES:	COc1cccc2c(cc(nc12)O)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL256497
PubChem CID:	826073
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001253] Quinolines and derivatives [CHEMONTID:0000056] Quinolones and derivatives [CHEMONTID:0001716] Hydroquinolones

*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
NPO24038	Casimiroa edulis	Species	Rutaceae	Eukaryota	n.a.	seed	n.a.	PMID[10075120]
NPO7344	Spiraea prunifolia	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11473429]
NPO23628	Imperata cylindrica	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16499335]
NPO24038	Casimiroa edulis	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17228877]
NPO18723	Zanthoxylum avicennae	Species	Rutaceae	Eukaryota	stem wood	Pakuashan, Changhua County, Taiwan	2006-Jun	PMID[18211005]
NPO23911	Alpinia officinarum	Species	Zingiberaceae	Eukaryota	n.a.	root	n.a.	PMID[18484537]
NPO23911	Alpinia officinarum	Species	Zingiberaceae	Eukaryota	n.a.	rhizome	n.a.	PMID[18484537]
NPO23911	Alpinia officinarum	Species	Zingiberaceae	Eukaryota	rhizomes	n.a.	n.a.	PMID[19615910]
NPO23911	Alpinia officinarum	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[29323912]
NPO23911	Alpinia officinarum	Species	Zingiberaceae	Eukaryota	n.a.	rhizome	n.a.	PMID[731398]
NPO23911	Alpinia officinarum	Species	Zingiberaceae	Eukaryota	n.a.	root	n.a.	PMID[731398]
NPO23628	Imperata cylindrica	Species	Poaceae	Eukaryota	n.a.	rhizome	n.a.	PMID[7714541]
NPO23628	Imperata cylindrica	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7760071]
NPO23628	Imperata cylindrica	Species	Poaceae	Eukaryota	n.a.	rhizome	n.a.	PMID[7798964]
NPO19895	Plectranthus hereroensis	Species	Lamiaceae	Eukaryota	Roots	n.a.	n.a.	PMID[7931371]
NPO23628	Imperata cylindrica	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7964801]
NPO23356	Ascodesmis sphaerospora	Species	Ascodesmidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9868168]
NPO23911	Alpinia officinarum	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24038	Casimiroa edulis	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23628	Imperata cylindrica	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18723	Zanthoxylum avicennae	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18723	Zanthoxylum avicennae	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23911	Alpinia officinarum	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24038	Casimiroa edulis	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23588	Ursinia anthemoides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23628	Imperata cylindrica	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23911	Alpinia officinarum	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO23628	Imperata cylindrica	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO18723	Zanthoxylum avicennae	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO23911	Alpinia officinarum	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO23628	Imperata cylindrica	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO7344	Spiraea prunifolia	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23588	Ursinia anthemoides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17492	Amomum reticulatum	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23356	Ascodesmis sphaerospora	Species	Ascodesmidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19895	Plectranthus hereroensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24396	Grosvenoria rimbachii	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO15572	Espeletiopsis purpurascens	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23398	Caralluma russeliana	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23911	Alpinia officinarum	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24280	Helianthus californicus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24038	Casimiroa edulis	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23822	Polypodium aureum	Species	Polypodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18723	Zanthoxylum avicennae	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23628	Imperata cylindrica	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23490	Dalbergia monetaria	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9814	Lactarius fuliginosus	Species	Russulaceae	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	3
Others	1

Activity Type	# Activity
Individual Protein	2
NON-MOLECULAR	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT204	Individual Protein	Acetylcholinesterase	Homo sapiens	IC50	>	100.0	ug.mL-1	PMID[483635]
NPT204	Individual Protein	Acetylcholinesterase	Homo sapiens	Inhibition	=	45.1	%	PMID[483635]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	50000.0	nM	PMID[483634]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	37950.0	nM	PMID[483634]

☑ 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 NPC42591 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	554
0.1-0.2	3855
0.2-0.3	13387
0.3-0.4	4226
0.4-0.5	14638
0.5-0.6	4523
0.6-0.7	1183
0.7-0.8	300
0.8-0.85	23
0.85-0.9	5
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9085	High Similarity	NPC118511
0.8966	High Similarity	NPC66083
0.8846	High Similarity	NPC66815
0.883	High Similarity	NPC283152
0.8772	High Similarity	NPC288943
0.8686	High Similarity	NPC62069
0.8434	Intermediate Similarity	NPC26872
0.8409	Intermediate Similarity	NPC478032
0.8404	Intermediate Similarity	NPC304183
0.8378	Intermediate Similarity	NPC128823
0.8284	Intermediate Similarity	NPC26850
0.8268	Intermediate Similarity	NPC320394
0.8207	Intermediate Similarity	NPC230403
0.8187	Intermediate Similarity	NPC242928
0.8156	Intermediate Similarity	NPC474798
0.8144	Intermediate Similarity	NPC203168
0.814	Intermediate Similarity	NPC177404
0.8135	Intermediate Similarity	NPC219664
0.8114	Intermediate Similarity	NPC473764
0.8114	Intermediate Similarity	NPC314940
0.811	Intermediate Similarity	NPC60553
0.8109	Intermediate Similarity	NPC200888
0.8108	Intermediate Similarity	NPC279401
0.8108	Intermediate Similarity	NPC79293
0.8077	Intermediate Similarity	NPC61350
0.8054	Intermediate Similarity	NPC114335
0.8054	Intermediate Similarity	NPC141915
0.8054	Intermediate Similarity	NPC280964
0.8	Intermediate Similarity	NPC469390
0.799	Intermediate Similarity	NPC148409
0.7978	Intermediate Similarity	NPC312872
0.7941	Intermediate Similarity	NPC153769
0.7933	Intermediate Similarity	NPC194724
0.7929	Intermediate Similarity	NPC8022
0.7929	Intermediate Similarity	NPC470799
0.7917	Intermediate Similarity	NPC475774
0.7892	Intermediate Similarity	NPC110741
0.7876	Intermediate Similarity	NPC137929
0.7876	Intermediate Similarity	NPC164374
0.7865	Intermediate Similarity	NPC252590
0.7853	Intermediate Similarity	NPC44161
0.785	Intermediate Similarity	NPC174576
0.7849	Intermediate Similarity	NPC144381
0.7833	Intermediate Similarity	NPC205372
0.7824	Intermediate Similarity	NPC245816
0.7824	Intermediate Similarity	NPC476138
0.7811	Intermediate Similarity	NPC473179
0.7796	Intermediate Similarity	NPC230805
0.7789	Intermediate Similarity	NPC224928
0.7784	Intermediate Similarity	NPC314573
0.7784	Intermediate Similarity	NPC204385
0.7753	Intermediate Similarity	NPC1527
0.7725	Intermediate Similarity	NPC475190
0.7716	Intermediate Similarity	NPC209769
0.7716	Intermediate Similarity	NPC185782
0.7706	Intermediate Similarity	NPC161292
0.7696	Intermediate Similarity	NPC243834
0.7696	Intermediate Similarity	NPC70956
0.7696	Intermediate Similarity	NPC267928
0.768	Intermediate Similarity	NPC199277
0.768	Intermediate Similarity	NPC135887
0.7673	Intermediate Similarity	NPC131885
0.7673	Intermediate Similarity	NPC184408
0.7673	Intermediate Similarity	NPC173080
0.7665	Intermediate Similarity	NPC280853
0.7663	Intermediate Similarity	NPC118776
0.7663	Intermediate Similarity	NPC206201
0.7641	Intermediate Similarity	NPC223427
0.7629	Intermediate Similarity	NPC470586
0.7622	Intermediate Similarity	NPC176127
0.7619	Intermediate Similarity	NPC285016
0.7619	Intermediate Similarity	NPC245657
0.7617	Intermediate Similarity	NPC280714
0.7611	Intermediate Similarity	NPC477888
0.7609	Intermediate Similarity	NPC222592
0.7609	Intermediate Similarity	NPC168486
0.7605	Intermediate Similarity	NPC471596
0.7602	Intermediate Similarity	NPC470930
0.76	Intermediate Similarity	NPC26679
0.7598	Intermediate Similarity	NPC132642
0.7594	Intermediate Similarity	NPC194040
0.7588	Intermediate Similarity	NPC471598
0.7581	Intermediate Similarity	NPC84478
0.7563	Intermediate Similarity	NPC472111
0.7554	Intermediate Similarity	NPC472168
0.7551	Intermediate Similarity	NPC317572
0.7548	Intermediate Similarity	NPC473185
0.7538	Intermediate Similarity	NPC469589
0.7536	Intermediate Similarity	NPC179287
0.7526	Intermediate Similarity	NPC18487
0.7526	Intermediate Similarity	NPC476167
0.7525	Intermediate Similarity	NPC474595
0.7525	Intermediate Similarity	NPC193777
0.7513	Intermediate Similarity	NPC329708
0.7513	Intermediate Similarity	NPC47059
0.7513	Intermediate Similarity	NPC165349
0.7513	Intermediate Similarity	NPC118832
0.7513	Intermediate Similarity	NPC264166
0.7513	Intermediate Similarity	NPC274291
0.75	Intermediate Similarity	NPC131017
0.75	Intermediate Similarity	NPC199667
0.7487	Intermediate Similarity	NPC19872
0.7487	Intermediate Similarity	NPC470931
0.7475	Intermediate Similarity	NPC39500
0.7475	Intermediate Similarity	NPC474594
0.7475	Intermediate Similarity	NPC162530
0.7475	Intermediate Similarity	NPC476287
0.7474	Intermediate Similarity	NPC192315
0.7473	Intermediate Similarity	NPC161887
0.7473	Intermediate Similarity	NPC219963
0.7473	Intermediate Similarity	NPC266551
0.7463	Intermediate Similarity	NPC187501
0.7462	Intermediate Similarity	NPC469440
0.7461	Intermediate Similarity	NPC251090
0.745	Intermediate Similarity	NPC473181
0.7438	Intermediate Similarity	NPC118228
0.7437	Intermediate Similarity	NPC321428
0.743	Intermediate Similarity	NPC79911
0.7427	Intermediate Similarity	NPC470403
0.7427	Intermediate Similarity	NPC470394
0.7427	Intermediate Similarity	NPC470404
0.7426	Intermediate Similarity	NPC94157
0.7426	Intermediate Similarity	NPC473180
0.7411	Intermediate Similarity	NPC475112
0.7411	Intermediate Similarity	NPC475085
0.7411	Intermediate Similarity	NPC291535
0.7398	Intermediate Similarity	NPC315957
0.7396	Intermediate Similarity	NPC471594
0.7389	Intermediate Similarity	NPC263439
0.7389	Intermediate Similarity	NPC471080
0.7389	Intermediate Similarity	NPC469592
0.7381	Intermediate Similarity	NPC140296
0.7379	Intermediate Similarity	NPC208084
0.7374	Intermediate Similarity	NPC120798
0.7371	Intermediate Similarity	NPC473182
0.7366	Intermediate Similarity	NPC88363
0.7366	Intermediate Similarity	NPC72980
0.7358	Intermediate Similarity	NPC307963
0.7358	Intermediate Similarity	NPC226202
0.7353	Intermediate Similarity	NPC16066
0.7351	Intermediate Similarity	NPC134586
0.7341	Intermediate Similarity	NPC470395
0.734	Intermediate Similarity	NPC202605
0.734	Intermediate Similarity	NPC112206
0.7337	Intermediate Similarity	NPC474409
0.7333	Intermediate Similarity	NPC202503
0.7327	Intermediate Similarity	NPC269367
0.7321	Intermediate Similarity	NPC314633
0.7317	Intermediate Similarity	NPC288349
0.7313	Intermediate Similarity	NPC287208
0.7313	Intermediate Similarity	NPC475910
0.7312	Intermediate Similarity	NPC211997
0.73	Intermediate Similarity	NPC476106
0.7297	Intermediate Similarity	NPC303225
0.7293	Intermediate Similarity	NPC473057
0.7286	Intermediate Similarity	NPC97746
0.7282	Intermediate Similarity	NPC473513
0.7269	Intermediate Similarity	NPC473183
0.7264	Intermediate Similarity	NPC193238
0.7264	Intermediate Similarity	NPC274640
0.7263	Intermediate Similarity	NPC20249
0.7263	Intermediate Similarity	NPC116573
0.726	Intermediate Similarity	NPC160100
0.7256	Intermediate Similarity	NPC473184
0.7255	Intermediate Similarity	NPC48353
0.7249	Intermediate Similarity	NPC212535
0.7246	Intermediate Similarity	NPC473822
0.7246	Intermediate Similarity	NPC469594
0.724	Intermediate Similarity	NPC296527
0.7238	Intermediate Similarity	NPC47298
0.7238	Intermediate Similarity	NPC315214
0.7233	Intermediate Similarity	NPC477110
0.7228	Intermediate Similarity	NPC477111
0.7222	Intermediate Similarity	NPC176538
0.7222	Intermediate Similarity	NPC329793
0.7222	Intermediate Similarity	NPC234197
0.7222	Intermediate Similarity	NPC329747
0.7216	Intermediate Similarity	NPC195268
0.7216	Intermediate Similarity	NPC133140
0.7214	Intermediate Similarity	NPC471736
0.7212	Intermediate Similarity	NPC17565
0.7212	Intermediate Similarity	NPC213530
0.7212	Intermediate Similarity	NPC292958
0.7212	Intermediate Similarity	NPC193267
0.7208	Intermediate Similarity	NPC72211
0.7206	Intermediate Similarity	NPC146418
0.7204	Intermediate Similarity	NPC473449
0.7202	Intermediate Similarity	NPC76748
0.72	Intermediate Similarity	NPC162484
0.7198	Intermediate Similarity	NPC314552
0.7198	Intermediate Similarity	NPC32028
0.7198	Intermediate Similarity	NPC159319
0.7196	Intermediate Similarity	NPC144114
0.719	Intermediate Similarity	NPC144452
0.7186	Intermediate Similarity	NPC232727
0.7183	Intermediate Similarity	NPC476997
0.7182	Intermediate Similarity	NPC285635
0.7179	Intermediate Similarity	NPC289786
0.7178	Intermediate Similarity	NPC283117
0.7177	Intermediate Similarity	NPC225279

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 NPC42591 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	334
0.1-0.2	727
0.2-0.3	879
0.3-0.4	1381
0.4-0.5	3043
0.5-0.6	2022
0.6-0.7	669
0.7-0.8	93
0.8-0.85	1
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.858	High Similarity	NPD5083	Clinical (unspecified phase)
0.8093	Intermediate Similarity	NPD4502	Phase 2
0.7956	Intermediate Similarity	NPD4204	Approved
0.7956	Intermediate Similarity	NPD4203	Approved
0.7927	Intermediate Similarity	NPD4305	Clinical (unspecified phase)
0.7889	Intermediate Similarity	NPD6159	Phase 2
0.7877	Intermediate Similarity	NPD9690	Approved
0.7874	Intermediate Similarity	NPD9705	Discontinued
0.7874	Intermediate Similarity	NPD112	Approved
0.7811	Intermediate Similarity	NPD3875	Discontinued
0.7801	Intermediate Similarity	NPD2177	Approved
0.7801	Intermediate Similarity	NPD2175	Phase 3
0.7801	Intermediate Similarity	NPD2176	Approved
0.7796	Intermediate Similarity	NPD9714	Clinical (unspecified phase)
0.7795	Intermediate Similarity	NPD7222	Phase 2
0.7778	Intermediate Similarity	NPD6590	Discontinued
0.7747	Intermediate Similarity	NPD1503	Clinical (unspecified phase)
0.7709	Intermediate Similarity	NPD4724	Clinical (unspecified phase)
0.7688	Intermediate Similarity	NPD5256	Discontinued
0.765	Intermediate Similarity	NPD3920	Phase 2
0.7644	Intermediate Similarity	NPD5512	Phase 3
0.7614	Intermediate Similarity	NPD7453	Approved
0.7614	Intermediate Similarity	NPD7452	Approved
0.7592	Intermediate Similarity	NPD6861	Clinical (unspecified phase)
0.7563	Intermediate Similarity	NPD5530	Phase 1
0.7525	Intermediate Similarity	NPD6290	Phase 2
0.7525	Intermediate Similarity	NPD5429	Discontinued
0.7513	Intermediate Similarity	NPD32	Approved
0.7513	Intermediate Similarity	NPD408	Approved
0.7513	Intermediate Similarity	NPD31	Approved
0.7513	Intermediate Similarity	NPD4122	Approved
0.7513	Intermediate Similarity	NPD6988	Phase 1
0.7513	Intermediate Similarity	NPD4034	Approved
0.7513	Intermediate Similarity	NPD4033	Approved
0.7513	Intermediate Similarity	NPD4039	Approved
0.7513	Intermediate Similarity	NPD4036	Approved
0.7513	Intermediate Similarity	NPD4035	Approved
0.7513	Intermediate Similarity	NPD4037	Approved
0.7513	Intermediate Similarity	NPD4038	Approved
0.75	Intermediate Similarity	NPD6491	Clinical (unspecified phase)
0.7461	Intermediate Similarity	NPD6550	Discontinued
0.7448	Intermediate Similarity	NPD9695	Approved
0.744	Intermediate Similarity	NPD1856	Discontinued
0.7438	Intermediate Similarity	NPD5417	Clinical (unspecified phase)
0.7402	Intermediate Similarity	NPD2433	Clinical (unspecified phase)
0.7398	Intermediate Similarity	NPD1739	Approved
0.7398	Intermediate Similarity	NPD1740	Approved
0.7396	Intermediate Similarity	NPD6569	Phase 2
0.7376	Intermediate Similarity	NPD5939	Approved
0.7376	Intermediate Similarity	NPD5936	Approved
0.7374	Intermediate Similarity	NPD6991	Approved
0.7371	Intermediate Similarity	NPD3478	Clinical (unspecified phase)
0.7371	Intermediate Similarity	NPD3477	Phase 2
0.7368	Intermediate Similarity	NPD2383	Phase 1
0.7363	Intermediate Similarity	NPD6872	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD1038	Approved
0.7347	Intermediate Similarity	NPD1768	Approved
0.7333	Intermediate Similarity	NPD1229	Phase 2
0.7306	Intermediate Similarity	NPD9689	Approved
0.73	Intermediate Similarity	NPD3842	Clinical (unspecified phase)
0.7296	Intermediate Similarity	NPD712	Clinical (unspecified phase)
0.7291	Intermediate Similarity	NPD5416	Discontinued
0.7263	Intermediate Similarity	NPD4669	Clinical (unspecified phase)
0.7263	Intermediate Similarity	NPD4671	Clinical (unspecified phase)
0.7263	Intermediate Similarity	NPD6344	Clinical (unspecified phase)
0.7263	Intermediate Similarity	NPD4670	Clinical (unspecified phase)
0.7259	Intermediate Similarity	NPD5999	Phase 2
0.7259	Intermediate Similarity	NPD4118	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD4795	Phase 2
0.7249	Intermediate Similarity	NPD5522	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD8109	Clinical (unspecified phase)
0.7243	Intermediate Similarity	NPD677	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD648	Clinical (unspecified phase)
0.7238	Intermediate Similarity	NPD1685	Approved
0.7238	Intermediate Similarity	NPD1684	Approved
0.7231	Intermediate Similarity	NPD3810	Clinical (unspecified phase)
0.7231	Intermediate Similarity	NPD4418	Discontinued
0.7228	Intermediate Similarity	NPD7672	Approved
0.7228	Intermediate Similarity	NPD7671	Approved
0.7228	Intermediate Similarity	NPD5658	Approved
0.7222	Intermediate Similarity	NPD6060	Clinical (unspecified phase)
0.7216	Intermediate Similarity	NPD3921	Approved
0.7216	Intermediate Similarity	NPD3924	Approved
0.7216	Intermediate Similarity	NPD3923	Approved
0.7216	Intermediate Similarity	NPD3922	Approved
0.7214	Intermediate Similarity	NPD3003	Approved
0.7198	Intermediate Similarity	NPD5164	Discontinued
0.7196	Intermediate Similarity	NPD7414	Clinical (unspecified phase)
0.7196	Intermediate Similarity	NPD3037	Phase 1
0.719	Intermediate Similarity	NPD2285	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD1620	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD1304	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD6361	Phase 2
0.7167	Intermediate Similarity	NPD9383	Approved
0.7167	Intermediate Similarity	NPD9382	Approved
0.7163	Intermediate Similarity	NPD7395	Discontinued
0.7163	Intermediate Similarity	NPD4429	Discontinued
0.7151	Intermediate Similarity	NPD6607	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD3324	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD3525	Discontinued
0.7121	Intermediate Similarity	NPD7889	Clinical (unspecified phase)
0.7116	Intermediate Similarity	NPD1505	Phase 2
0.7105	Intermediate Similarity	NPD3386	Phase 2
0.7104	Intermediate Similarity	NPD861	Approved
0.7104	Intermediate Similarity	NPD863	Approved
0.7104	Intermediate Similarity	NPD862	Approved
0.7101	Intermediate Similarity	NPD7538	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD2951	Discontinued
0.7094	Intermediate Similarity	NPD1392	Approved
0.7092	Intermediate Similarity	NPD4551	Phase 2
0.7087	Intermediate Similarity	NPD7069	Discontinued
0.7085	Intermediate Similarity	NPD9687	Approved
0.7085	Intermediate Similarity	NPD9688	Approved
0.7074	Intermediate Similarity	NPD4354	Approved
0.7071	Intermediate Similarity	NPD6769	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD6147	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD5612	Discontinued
0.7056	Intermediate Similarity	NPD6553	Clinical (unspecified phase)
0.7053	Intermediate Similarity	NPD5945	Phase 1
0.7053	Intermediate Similarity	NPD5944	Phase 1
0.7051	Intermediate Similarity	NPD6494	Phase 2
0.7048	Intermediate Similarity	NPD3514	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD4372	Phase 1
0.7039	Intermediate Similarity	NPD2882	Phase 1
0.7039	Intermediate Similarity	NPD6476	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD9706	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD6158	Phase 2
0.7035	Intermediate Similarity	NPD2727	Phase 2
0.7028	Intermediate Similarity	NPD1954	Phase 1
0.7028	Intermediate Similarity	NPD6160	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD5902	Approved
0.7019	Intermediate Similarity	NPD5903	Approved
0.701	Intermediate Similarity	NPD1034	Phase 3
0.701	Intermediate Similarity	NPD1033	Clinical (unspecified phase)
0.6991	Remote Similarity	NPD5022	Discontinued
0.6985	Remote Similarity	NPD1622	Discontinued
0.698	Remote Similarity	NPD5669	Clinical (unspecified phase)
0.6973	Remote Similarity	NPD926	Approved
0.6973	Remote Similarity	NPD925	Approved
0.697	Remote Similarity	NPD3395	Approved
0.697	Remote Similarity	NPD3396	Approved
0.6963	Remote Similarity	NPD3925	Approved
0.6959	Remote Similarity	NPD4375	Approved
0.6957	Remote Similarity	NPD4131	Phase 3
0.6957	Remote Similarity	NPD7703	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD6220	Phase 3
0.6954	Remote Similarity	NPD3963	Phase 1
0.6947	Remote Similarity	NPD5751	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD8244	Phase 2
0.6939	Remote Similarity	NPD2410	Phase 2
0.6938	Remote Similarity	NPD6140	Clinical (unspecified phase)
0.6931	Remote Similarity	NPD1923	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD3816	Phase 1
0.6923	Remote Similarity	NPD980	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD3815	Phase 1
0.6923	Remote Similarity	NPD4927	Discontinued
0.6919	Remote Similarity	NPD6985	Discontinued
0.6915	Remote Similarity	NPD4083	Discontinued
0.6907	Remote Similarity	NPD2762	Phase 2
0.6907	Remote Similarity	NPD4889	Approved
0.6905	Remote Similarity	NPD6643	Discontinued
0.6902	Remote Similarity	NPD9398	Clinical (unspecified phase)
0.69	Remote Similarity	NPD5003	Discontinued
0.69	Remote Similarity	NPD2952	Discontinued
0.69	Remote Similarity	NPD2476	Clinical (unspecified phase)
0.6895	Remote Similarity	NPD6741	Clinical (unspecified phase)
0.689	Remote Similarity	NPD2615	Phase 3
0.689	Remote Similarity	NPD2616	Phase 3
0.6887	Remote Similarity	NPD7194	Discontinued
0.6885	Remote Similarity	NPD2581	Approved
0.6885	Remote Similarity	NPD2582	Approved
0.6884	Remote Similarity	NPD6251	Discontinued
0.6884	Remote Similarity	NPD6246	Approved
0.6881	Remote Similarity	NPD4396	Clinical (unspecified phase)
0.6878	Remote Similarity	NPD6150	Discontinued
0.6872	Remote Similarity	NPD2917	Approved
0.6869	Remote Similarity	NPD6824	Clinical (unspecified phase)
0.6866	Remote Similarity	NPD7710	Clinical (unspecified phase)
0.6854	Remote Similarity	NPD5930	Phase 3
0.6854	Remote Similarity	NPD1305	Clinical (unspecified phase)
0.6853	Remote Similarity	NPD1213	Phase 3
0.6853	Remote Similarity	NPD2564	Approved
0.6853	Remote Similarity	NPD2565	Phase 2
0.6852	Remote Similarity	NPD7603	Discontinued
0.6845	Remote Similarity	NPD425	Approved
0.6845	Remote Similarity	NPD424	Approved
0.6832	Remote Similarity	NPD4548	Discontinued
0.6832	Remote Similarity	NPD5547	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD3946	Clinical (unspecified phase)
0.6827	Remote Similarity	NPD1166	Clinical (unspecified phase)
0.6827	Remote Similarity	NPD5420	Discontinued
0.682	Remote Similarity	NPD6326	Phase 2
0.682	Remote Similarity	NPD6327	Phase 1
0.6814	Remote Similarity	NPD2779	Approved
0.6812	Remote Similarity	NPD5863	Clinical (unspecified phase)
0.6808	Remote Similarity	NPD3258	Approved
0.6804	Remote Similarity	NPD1466	Phase 3
0.6804	Remote Similarity	NPD1467	Approved
0.6798	Remote Similarity	NPD6525	Clinical (unspecified phase)
0.6794	Remote Similarity	NPD5067	Phase 2

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