NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	221.11
Volume:	225.817
LogP:	0.995
LogD:	1.301
LogS:	-1.351
# Rotatable Bonds:	2
TPSA:	38.77
# H-Bond Aceptor:	4
# H-Bond Donor:	0
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.756
Synthetic Accessibility Score:	1.981
Fsp3:	0.417
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:	-4.557
MDCK Permeability:	1.3985056284582242e-05
Pgp-inhibitor:	0.002
Pgp-substrate:	0.086
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.076
30% Bioavailability (F30%):	0.617

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.991
Plasma Protein Binding (PPB):	53.75562286376953%
Volume Distribution (VD):	1.306
Pgp-substrate:	37.05617141723633%

ADMET: Metabolism

CYP1A2-inhibitor:	0.47
CYP1A2-substrate:	0.923
CYP2C19-inhibitor:	0.096
CYP2C19-substrate:	0.892
CYP2C9-inhibitor:	0.017
CYP2C9-substrate:	0.775
CYP2D6-inhibitor:	0.019
CYP2D6-substrate:	0.895
CYP3A4-inhibitor:	0.022
CYP3A4-substrate:	0.392

ADMET: Excretion

Clearance (CL):	5.79
Half-life (T1/2):	0.836

ADMET: Toxicity

hERG Blockers:	0.037
Human Hepatotoxicity (H-HT):	0.33
Drug-inuced Liver Injury (DILI):	0.452
AMES Toxicity:	0.016
Rat Oral Acute Toxicity:	0.04
Maximum Recommended Daily Dose:	0.132
Skin Sensitization:	0.109
Carcinogencity:	0.041
Eye Corrosion:	0.008
Eye Irritation:	0.33
Respiratory Toxicity:	0.027

Download Data

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

Natural Product: NPC119669

Natural Product ID:	NPC119669
*Common Name:**	6,7-Dimethoxy-2-Methyl-3,4-Dihydroisoquinolin-1-One
IUPAC Name:	6,7-dimethoxy-2-methyl-3,4-dihydroisoquinolin-1-one
Synonyms:	N-Methylcorydaldine
Standard InCHIKey:	BDIZBBGNYDRCCA-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C12H15NO3/c1-13-5-4-8-6-10(15-2)11(16-3)7-9(8)12(13)14/h6-7H,4-5H2,1-3H3
SMILES:	COc1cc2c(cc1OC)CCN(C2=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL504722
PubChem CID:	303906
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0002566] Isoquinolines and derivatives [CHEMONTID:0002054] Isoquinolones and derivatives

*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
NPO20526	Menispermum dauricum	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11473438]
NPO29391	Papaver bracteatum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17226487]
NPO1338	Arcangelisia gusanlung	Species	Menispermaceae	Eukaryota	n.a.	stem	n.a.	PMID[21500777]
NPO20526	Menispermum dauricum	Species	Menispermaceae	Eukaryota	n.a.	rhizome	n.a.	PMID[8281582]
NPO22553	Thalictrum fendleri	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29391	Papaver bracteatum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO20526	Menispermum dauricum	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18997	Hernandia sonora	Species	Hernandiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22553	Thalictrum fendleri	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20526	Menispermum dauricum	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14115	Papaver urbanianum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26469	Thalictrum delavayi	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18997	Hernandia sonora	Species	Hernandiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29391	Papaver bracteatum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20526	Menispermum dauricum	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO29391	Papaver bracteatum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO22553	Thalictrum fendleri	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18997	Hernandia sonora	Species	Hernandiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20526	Menispermum dauricum	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1338	Arcangelisia gusanlung	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29391	Papaver bracteatum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26469	Thalictrum delavayi	Species	Ranunculaceae	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	2
Potency	7

Activity Type	# Activity
Individual Protein	5
Organism	1
Others	2
Protein-Protein Interaction	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT150	Individual Protein	Anthrax lethal factor	Bacillus anthracis	Potency	=	12589.3	nM	PMID[459992]
NPT43	Individual Protein	Tyrosinase	Agaricus bisporus	IC50	>	1000000.0	nM	PMID[459993]
NPT135	Individual Protein	Chromobox protein homolog 1	Homo sapiens	Potency	n.a.	89125.1	nM	PMID[459994]
NPT10	Individual Protein	Geminin	Homo sapiens	Potency	n.a.	29.1	nM	PMID[459994]
NPT101	Individual Protein	Glucagon-like peptide 1 receptor	Homo sapiens	Potency	n.a.	31622.8	nM	PMID[459994]
NPT2	Others	Unspecified		IC50	>	4.0	ug.mL-1	PMID[459990]
NPT197	Protein-Protein Interaction	Menin/Histone-lysine N-methyltransferase MLL	Homo sapiens	Potency	=	39810.7	nM	PMID[459991]
NPT2	Others	Unspecified		Potency	=	35481.3	nM	PMID[459991]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Potency	n.a.	11689.1	nM	PMID[459994]

☑ 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 NPC119669 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	304
0.1-0.2	2315
0.2-0.3	7491
0.3-0.4	9821
0.4-0.5	5026
0.5-0.6	13177
0.6-0.7	4085
0.7-0.8	450
0.8-0.85	18
0.85-0.9	7
0.9-0.95	0
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.953	High Similarity	NPC135006
0.8718	High Similarity	NPC153631
0.8571	High Similarity	NPC470708
0.8528	High Similarity	NPC222524
0.8462	Intermediate Similarity	NPC160193
0.8447	Intermediate Similarity	NPC86469
0.8344	Intermediate Similarity	NPC67978
0.8344	Intermediate Similarity	NPC303581
0.8312	Intermediate Similarity	NPC470088
0.8242	Intermediate Similarity	NPC308267
0.8199	Intermediate Similarity	NPC476569
0.8198	Intermediate Similarity	NPC254957
0.8176	Intermediate Similarity	NPC169387
0.8176	Intermediate Similarity	NPC477259
0.817	Intermediate Similarity	NPC469978
0.8166	Intermediate Similarity	NPC116007
0.8163	Intermediate Similarity	NPC266425
0.8163	Intermediate Similarity	NPC160692
0.8129	Intermediate Similarity	NPC208890
0.8121	Intermediate Similarity	NPC301050
0.8121	Intermediate Similarity	NPC7018
0.8121	Intermediate Similarity	NPC131204
0.8114	Intermediate Similarity	NPC71124
0.8098	Intermediate Similarity	NPC206941
0.8059	Intermediate Similarity	NPC83511
0.8036	Intermediate Similarity	NPC121400
0.8	Intermediate Similarity	NPC57512
0.7988	Intermediate Similarity	NPC27887
0.7986	Intermediate Similarity	NPC30216
0.7975	Intermediate Similarity	NPC476579
0.7974	Intermediate Similarity	NPC908
0.7974	Intermediate Similarity	NPC138438
0.7966	Intermediate Similarity	NPC5374
0.7961	Intermediate Similarity	NPC314682
0.7947	Intermediate Similarity	NPC253429
0.7925	Intermediate Similarity	NPC476580
0.7908	Intermediate Similarity	NPC328750
0.7908	Intermediate Similarity	NPC188163
0.7908	Intermediate Similarity	NPC213206
0.7908	Intermediate Similarity	NPC474915
0.7898	Intermediate Similarity	NPC477258
0.7895	Intermediate Similarity	NPC231572
0.7889	Intermediate Similarity	NPC207971
0.787	Intermediate Similarity	NPC35680
0.7853	Intermediate Similarity	NPC24228
0.7845	Intermediate Similarity	NPC268077
0.7829	Intermediate Similarity	NPC252107
0.7829	Intermediate Similarity	NPC225745
0.7823	Intermediate Similarity	NPC172403
0.7818	Intermediate Similarity	NPC231198
0.7811	Intermediate Similarity	NPC20395
0.7806	Intermediate Similarity	NPC136860
0.7806	Intermediate Similarity	NPC128019
0.7806	Intermediate Similarity	NPC476567
0.7799	Intermediate Similarity	NPC223125
0.7798	Intermediate Similarity	NPC227683
0.7763	Intermediate Similarity	NPC99078
0.7748	Intermediate Similarity	NPC167096
0.7736	Intermediate Similarity	NPC469540
0.7736	Intermediate Similarity	NPC469539
0.7725	Intermediate Similarity	NPC284842
0.7712	Intermediate Similarity	NPC220923
0.7712	Intermediate Similarity	NPC470707
0.7711	Intermediate Similarity	NPC306669
0.7708	Intermediate Similarity	NPC225245
0.7707	Intermediate Similarity	NPC185838
0.7707	Intermediate Similarity	NPC130926
0.7702	Intermediate Similarity	NPC58661
0.7702	Intermediate Similarity	NPC223124
0.7697	Intermediate Similarity	NPC205178
0.7697	Intermediate Similarity	NPC277042
0.7697	Intermediate Similarity	NPC136330
0.7697	Intermediate Similarity	NPC180647
0.7697	Intermediate Similarity	NPC196609
0.7697	Intermediate Similarity	NPC255817
0.7697	Intermediate Similarity	NPC73883
0.7697	Intermediate Similarity	NPC251454
0.7697	Intermediate Similarity	NPC230698
0.7683	Intermediate Similarity	NPC118804
0.7683	Intermediate Similarity	NPC106786
0.7663	Intermediate Similarity	NPC308943
0.7643	Intermediate Similarity	NPC125852
0.7643	Intermediate Similarity	NPC294249
0.7627	Intermediate Similarity	NPC226708
0.761	Intermediate Similarity	NPC179825
0.761	Intermediate Similarity	NPC476144
0.761	Intermediate Similarity	NPC51957
0.761	Intermediate Similarity	NPC106295
0.761	Intermediate Similarity	NPC191376
0.761	Intermediate Similarity	NPC210437
0.761	Intermediate Similarity	NPC321505
0.761	Intermediate Similarity	NPC476151
0.761	Intermediate Similarity	NPC16107
0.7586	Intermediate Similarity	NPC102760
0.7572	Intermediate Similarity	NPC99723
0.7569	Intermediate Similarity	NPC207239
0.7562	Intermediate Similarity	NPC476571
0.7562	Intermediate Similarity	NPC147390
0.7562	Intermediate Similarity	NPC59907
0.7562	Intermediate Similarity	NPC7467
0.7562	Intermediate Similarity	NPC37144
0.7562	Intermediate Similarity	NPC24233
0.7562	Intermediate Similarity	NPC428
0.7562	Intermediate Similarity	NPC246587
0.7562	Intermediate Similarity	NPC135538
0.7562	Intermediate Similarity	NPC475959
0.7557	Intermediate Similarity	NPC162694
0.7551	Intermediate Similarity	NPC474691
0.7545	Intermediate Similarity	NPC59567
0.7531	Intermediate Similarity	NPC85747
0.7531	Intermediate Similarity	NPC8337
0.753	Intermediate Similarity	NPC26353
0.7528	Intermediate Similarity	NPC63152
0.7516	Intermediate Similarity	NPC103379
0.7516	Intermediate Similarity	NPC477565
0.75	Intermediate Similarity	NPC169742
0.7484	Intermediate Similarity	NPC194359
0.7484	Intermediate Similarity	NPC28641
0.7473	Intermediate Similarity	NPC267414
0.7471	Intermediate Similarity	NPC241055
0.7469	Intermediate Similarity	NPC88249
0.7469	Intermediate Similarity	NPC97221
0.7469	Intermediate Similarity	NPC274026
0.7469	Intermediate Similarity	NPC151895
0.7469	Intermediate Similarity	NPC192768
0.7469	Intermediate Similarity	NPC220858
0.7466	Intermediate Similarity	NPC295317
0.7458	Intermediate Similarity	NPC471650
0.7444	Intermediate Similarity	NPC469815
0.7444	Intermediate Similarity	NPC469816
0.7442	Intermediate Similarity	NPC4669
0.7438	Intermediate Similarity	NPC290404
0.7435	Intermediate Similarity	NPC38964
0.7434	Intermediate Similarity	NPC476570
0.7432	Intermediate Similarity	NPC217277
0.7423	Intermediate Similarity	NPC476568
0.7423	Intermediate Similarity	NPC81733
0.7423	Intermediate Similarity	NPC326316
0.7419	Intermediate Similarity	NPC137172
0.7419	Intermediate Similarity	NPC416184
0.7419	Intermediate Similarity	NPC95485
0.7419	Intermediate Similarity	NPC89504
0.7419	Intermediate Similarity	NPC88065
0.7419	Intermediate Similarity	NPC145446
0.7418	Intermediate Similarity	NPC14622
0.7418	Intermediate Similarity	NPC124302
0.7418	Intermediate Similarity	NPC73020
0.7418	Intermediate Similarity	NPC70290
0.7418	Intermediate Similarity	NPC215098
0.7418	Intermediate Similarity	NPC46744
0.7416	Intermediate Similarity	NPC141440
0.7407	Intermediate Similarity	NPC60538
0.7407	Intermediate Similarity	NPC207824
0.7407	Intermediate Similarity	NPC92541
0.7407	Intermediate Similarity	NPC219162
0.7403	Intermediate Similarity	NPC33256
0.7396	Intermediate Similarity	NPC35345
0.7396	Intermediate Similarity	NPC2770
0.7396	Intermediate Similarity	NPC39103
0.7389	Intermediate Similarity	NPC94499
0.7386	Intermediate Similarity	NPC217574
0.7382	Intermediate Similarity	NPC55470
0.7378	Intermediate Similarity	NPC133011
0.7378	Intermediate Similarity	NPC82285
0.7378	Intermediate Similarity	NPC233029
0.7378	Intermediate Similarity	NPC210148
0.7378	Intermediate Similarity	NPC148898
0.7372	Intermediate Similarity	NPC95366
0.7372	Intermediate Similarity	NPC248505
0.7368	Intermediate Similarity	NPC470324
0.7362	Intermediate Similarity	NPC478189
0.7358	Intermediate Similarity	NPC82056
0.7355	Intermediate Similarity	NPC96406
0.7351	Intermediate Similarity	NPC32163
0.7351	Intermediate Similarity	NPC16651
0.7351	Intermediate Similarity	NPC286683
0.7346	Intermediate Similarity	NPC130941
0.7346	Intermediate Similarity	NPC153644
0.734	Intermediate Similarity	NPC207873
0.734	Intermediate Similarity	NPC100573
0.7337	Intermediate Similarity	NPC226652
0.7337	Intermediate Similarity	NPC120671
0.7337	Intermediate Similarity	NPC72788
0.7337	Intermediate Similarity	NPC314100
0.733	Intermediate Similarity	NPC298339
0.7321	Intermediate Similarity	NPC475780
0.7318	Intermediate Similarity	NPC166979
0.7317	Intermediate Similarity	NPC76213
0.7317	Intermediate Similarity	NPC277669
0.7308	Intermediate Similarity	NPC469808
0.7308	Intermediate Similarity	NPC125924
0.7303	Intermediate Similarity	NPC214629
0.7294	Intermediate Similarity	NPC168409
0.729	Intermediate Similarity	NPC45783
0.729	Intermediate Similarity	NPC328419
0.729	Intermediate Similarity	NPC94280
0.729	Intermediate Similarity	NPC193673
0.729	Intermediate Similarity	NPC159150
0.729	Intermediate Similarity	NPC103947
0.7289	Intermediate Similarity	NPC204828

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 NPC119669 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	196
0.1-0.2	855
0.2-0.3	1057
0.3-0.4	1923
0.4-0.5	2616
0.5-0.6	1930
0.6-0.7	482
0.7-0.8	77
0.8-0.85	11
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9	High Similarity	NPD1337	Clinical (unspecified phase)
0.8808	High Similarity	NPD824	Approved
0.8645	High Similarity	NPD5978	Approved
0.8645	High Similarity	NPD5977	Approved
0.8333	Intermediate Similarity	NPD7110	Phase 1
0.8333	Intermediate Similarity	NPD7109	Clinical (unspecified phase)
0.8323	Intermediate Similarity	NPD6618	Phase 2
0.8312	Intermediate Similarity	NPD3639	Approved
0.8312	Intermediate Similarity	NPD3641	Approved
0.8312	Intermediate Similarity	NPD6662	Clinical (unspecified phase)
0.8312	Intermediate Similarity	NPD3640	Phase 3
0.8243	Intermediate Similarity	NPD743	Approved
0.8153	Intermediate Similarity	NPD6876	Approved
0.8153	Intermediate Similarity	NPD6875	Approved
0.7965	Intermediate Similarity	NPD7291	Discontinued
0.7964	Intermediate Similarity	NPD5313	Approved
0.7964	Intermediate Similarity	NPD5312	Approved
0.7963	Intermediate Similarity	NPD1309	Phase 2
0.7963	Intermediate Similarity	NPD1307	Phase 2
0.7908	Intermediate Similarity	NPD4664	Clinical (unspecified phase)
0.7875	Intermediate Similarity	NPD6385	Approved
0.7875	Intermediate Similarity	NPD6386	Approved
0.7848	Intermediate Similarity	NPD1670	Discontinued
0.7771	Intermediate Similarity	NPD4166	Phase 2
0.7771	Intermediate Similarity	NPD5525	Clinical (unspecified phase)
0.7765	Intermediate Similarity	NPD6297	Approved
0.7709	Intermediate Similarity	NPD5071	Phase 2
0.7697	Intermediate Similarity	NPD2492	Phase 1
0.7682	Intermediate Similarity	NPD3140	Approved
0.7682	Intermediate Similarity	NPD3142	Approved
0.7654	Intermediate Similarity	NPD5564	Approved
0.7619	Intermediate Similarity	NPD5242	Approved
0.7614	Intermediate Similarity	NPD6377	Clinical (unspecified phase)
0.761	Intermediate Similarity	NPD4584	Approved
0.7586	Intermediate Similarity	NPD6851	Approved
0.7586	Intermediate Similarity	NPD6853	Approved
0.7546	Intermediate Similarity	NPD6873	Phase 2
0.7542	Intermediate Similarity	NPD4413	Clinical (unspecified phase)
0.7527	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD4084	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7667	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD160	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD2669	Clinical (unspecified phase)
0.7434	Intermediate Similarity	NPD5718	Phase 2
0.7423	Intermediate Similarity	NPD4017	Approved
0.7418	Intermediate Similarity	NPD4420	Approved
0.741	Intermediate Similarity	NPD5353	Approved
0.7407	Intermediate Similarity	NPD6031	Approved
0.7407	Intermediate Similarity	NPD6030	Approved
0.7396	Intermediate Similarity	NPD6107	Approved
0.7389	Intermediate Similarity	NPD6181	Discontinued
0.7384	Intermediate Similarity	NPD2822	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD2898	Approved
0.7353	Intermediate Similarity	NPD5183	Approved
0.7353	Intermediate Similarity	NPD5186	Approved
0.7333	Intermediate Similarity	NPD4772	Phase 2
0.7333	Intermediate Similarity	NPD4773	Phase 2
0.733	Intermediate Similarity	NPD6146	Clinical (unspecified phase)
0.733	Intermediate Similarity	NPD3534	Clinical (unspecified phase)
0.7326	Intermediate Similarity	NPD7607	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7299	Intermediate Similarity	NPD5441	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD518	Clinical (unspecified phase)
0.7289	Intermediate Similarity	NPD7298	Approved
0.7284	Intermediate Similarity	NPD3688	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD3146	Approved
0.7273	Intermediate Similarity	NPD2592	Discontinued
0.7273	Intermediate Similarity	NPD7132	Clinical (unspecified phase)
0.7258	Intermediate Similarity	NPD5006	Approved
0.7258	Intermediate Similarity	NPD5005	Approved
0.7243	Intermediate Similarity	NPD5457	Discontinued
0.7243	Intermediate Similarity	NPD7255	Clinical (unspecified phase)
0.7233	Intermediate Similarity	NPD3655	Clinical (unspecified phase)
0.7232	Intermediate Similarity	NPD7281	Phase 3
0.7232	Intermediate Similarity	NPD7280	Phase 3
0.7222	Intermediate Similarity	NPD5297	Approved
0.7222	Intermediate Similarity	NPD5896	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD2325	Approved
0.7188	Intermediate Similarity	NPD7225	Discontinued
0.7178	Intermediate Similarity	NPD1424	Approved
0.7173	Intermediate Similarity	NPD4997	Clinical (unspecified phase)
0.7168	Intermediate Similarity	NPD6894	Phase 1
0.716	Intermediate Similarity	NPD6884	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD2968	Approved
0.7135	Intermediate Similarity	NPD2971	Approved
0.7124	Intermediate Similarity	NPD9494	Approved
0.712	Intermediate Similarity	NPD6834	Approved
0.7101	Intermediate Similarity	NPD5967	Approved
0.7101	Intermediate Similarity	NPD5616	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD6895	Approved
0.7089	Intermediate Similarity	NPD6896	Approved
0.7088	Intermediate Similarity	NPD3808	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD1421	Approved
0.7086	Intermediate Similarity	NPD1420	Approved
0.7077	Intermediate Similarity	NPD8149	Discontinued
0.7069	Intermediate Similarity	NPD3451	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD4107	Approved
0.7045	Intermediate Similarity	NPD3050	Clinical (unspecified phase)
0.7035	Intermediate Similarity	NPD7201	Clinical (unspecified phase)
0.7029	Intermediate Similarity	NPD6720	Clinical (unspecified phase)
0.702	Intermediate Similarity	NPD7858	Clinical (unspecified phase)
0.7017	Intermediate Similarity	NPD3863	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD2560	Approved
0.7	Intermediate Similarity	NPD2563	Approved
0.6994	Remote Similarity	NPD7802	Discontinued
0.6994	Remote Similarity	NPD5241	Discontinued
0.6989	Remote Similarity	NPD7177	Discontinued
0.6989	Remote Similarity	NPD5603	Clinical (unspecified phase)
0.6984	Remote Similarity	NPD956	Clinical (unspecified phase)
0.6984	Remote Similarity	NPD3057	Approved
0.6983	Remote Similarity	NPD7190	Clinical (unspecified phase)
0.6982	Remote Similarity	NPD7248	Discontinued
0.6982	Remote Similarity	NPD7577	Discontinued
0.6978	Remote Similarity	NPD6040	Clinical (unspecified phase)
0.6978	Remote Similarity	NPD6608	Clinical (unspecified phase)
0.6973	Remote Similarity	NPD3473	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD4010	Discontinued
0.6954	Remote Similarity	NPD6071	Discontinued
0.6944	Remote Similarity	NPD5917	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD2674	Phase 3
0.6931	Remote Similarity	NPD4482	Phase 3
0.6919	Remote Similarity	NPD7831	Phase 2
0.6919	Remote Similarity	NPD8005	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD7832	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD7833	Phase 2
0.6918	Remote Similarity	NPD2653	Approved
0.6909	Remote Similarity	NPD3124	Discontinued
0.6906	Remote Similarity	NPD6021	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD7261	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD2651	Approved
0.6905	Remote Similarity	NPD2649	Approved
0.6904	Remote Similarity	NPD5025	Approved
0.6902	Remote Similarity	NPD2488	Approved
0.6902	Remote Similarity	NPD2490	Approved
0.6902	Remote Similarity	NPD7668	Phase 2
0.6895	Remote Similarity	NPD2491	Approved
0.6895	Remote Similarity	NPD3533	Approved
0.6895	Remote Similarity	NPD2972	Approved
0.6895	Remote Similarity	NPD3448	Approved
0.689	Remote Similarity	NPD5084	Clinical (unspecified phase)
0.6886	Remote Similarity	NPD5586	Clinical (unspecified phase)
0.6885	Remote Similarity	NPD7693	Approved
0.6871	Remote Similarity	NPD2654	Approved
0.686	Remote Similarity	NPD6788	Approved
0.6854	Remote Similarity	NPD6020	Phase 2
0.6851	Remote Similarity	NPD4078	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD2120	Phase 2
0.6848	Remote Similarity	NPD6783	Clinical (unspecified phase)
0.6845	Remote Similarity	NPD4210	Discontinued
0.6842	Remote Similarity	NPD6818	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD2904	Discontinued
0.6836	Remote Similarity	NPD3446	Phase 1
0.6835	Remote Similarity	NPD554	Clinical (unspecified phase)
0.6833	Remote Similarity	NPD5192	Clinical (unspecified phase)
0.6833	Remote Similarity	NPD7038	Approved
0.6833	Remote Similarity	NPD7039	Approved
0.6826	Remote Similarity	NPD3647	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD6533	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD6688	Approved
0.6818	Remote Similarity	NPD6687	Approved
0.6812	Remote Similarity	NPD7942	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD2975	Approved
0.6809	Remote Similarity	NPD2973	Approved
0.6809	Remote Similarity	NPD2974	Approved
0.6798	Remote Similarity	NPD8252	Approved
0.6798	Remote Similarity	NPD8099	Discontinued
0.6798	Remote Similarity	NPD8251	Approved
0.6791	Remote Similarity	NPD7669	Phase 3
0.6788	Remote Similarity	NPD5307	Clinical (unspecified phase)
0.6784	Remote Similarity	NPD6844	Discontinued
0.6782	Remote Similarity	NPD8245	Clinical (unspecified phase)
0.6782	Remote Similarity	NPD6997	Phase 2
0.6772	Remote Similarity	NPD3145	Approved
0.6772	Remote Similarity	NPD3144	Approved
0.6768	Remote Similarity	NPD7559	Phase 2
0.6766	Remote Similarity	NPD1754	Clinical (unspecified phase)
0.676	Remote Similarity	NPD8156	Discontinued
0.6757	Remote Similarity	NPD5910	Clinical (unspecified phase)
0.6753	Remote Similarity	NPD1755	Approved
0.6748	Remote Similarity	NPD3656	Approved
0.6747	Remote Similarity	NPD7124	Phase 2
0.6744	Remote Similarity	NPD4585	Approved
0.6743	Remote Similarity	NPD5677	Discontinued
0.6742	Remote Similarity	NPD3366	Approved
0.6737	Remote Similarity	NPD7811	Phase 3
0.6737	Remote Similarity	NPD7810	Phase 3
0.6733	Remote Similarity	NPD5536	Phase 2
0.673	Remote Similarity	NPD2245	Discovery
0.6723	Remote Similarity	NPD8051	Clinical (unspecified phase)
0.6722	Remote Similarity	NPD3885	Approved
0.6718	Remote Similarity	NPD5950	Discontinued
0.6714	Remote Similarity	NPD7048	Phase 3
0.671	Remote Similarity	NPD1876	Approved
0.6705	Remote Similarity	NPD2821	Approved
0.6704	Remote Similarity	NPD5940	Clinical (unspecified phase)
0.6702	Remote Similarity	NPD4580	Approved
0.6688	Remote Similarity	NPD3972	Approved
0.6687	Remote Similarity	NPD3109	Approved

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data