NPASS Compound

Structure

CID51957 OpenBabel06191715392D 27 29 0 0 1 0 0 0 0 0999 V2000 0.5000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.1603 -5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.4282 -7.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2321 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3660 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5622 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6962 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9641 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.4282 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6962 -5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0981 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5622 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6962 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0981 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8301 -3.5000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 1.3660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.4282 -5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5622 -5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8301 -2.5000 0.0000 N 0 0 3 0 0 0 0 0 0 0 0 0 0.5000 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 8.2942 -5.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.5622 -6.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2321 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.6167 -3.4776 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0 1 23 1 0 0 0 0 2 24 1 0 0 0 0 3 25 1 0 0 0 0 4 26 1 0 0 0 0 5 6 2 0 0 0 0 5 13 1 0 0 0 0 6 18 1 0 0 0 0 7 8 1 0 0 0 0 7 14 1 0 0 0 0 8 22 1 0 0 0 0 9 13 1 0 0 0 0 9 17 1 0 0 0 0 10 14 2 0 0 0 0 10 19 1 0 0 0 0 11 15 2 0 0 0 0 11 20 1 0 0 0 0 12 16 1 0 0 0 0 12 22 1 0 0 0 0 13 16 2 0 0 0 0 14 15 1 0 0 0 0 15 17 1 0 0 0 0 16 21 1 0 0 0 0 17 22 1 0 0 0 0 18 21 2 0 0 0 0 18 23 1 0 0 0 0 19 20 2 0 0 0 0 19 24 1 0 0 0 0 20 25 1 0 0 0 0 21 26 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	376.15
Volume:	362.68
LogP:	1.099
LogD:	0.262
LogS:	-4.141
# Rotatable Bonds:	0
TPSA:	110.13
# H-Bond Aceptor:	7
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.357
Synthetic Accessibility Score:	6.613
Fsp3:	0.75
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.383
MDCK Permeability:	2.5641034881118685e-05
Pgp-inhibitor:	0.009
Pgp-substrate:	0.725
Human Intestinal Absorption (HIA):	0.055
20% Bioavailability (F20%):	0.018
30% Bioavailability (F30%):	0.849

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.912
Plasma Protein Binding (PPB):	52.48490524291992%
Volume Distribution (VD):	1.03
Pgp-substrate:	65.7293472290039%

ADMET: Metabolism

CYP1A2-inhibitor:	0.013
CYP1A2-substrate:	0.87
CYP2C19-inhibitor:	0.02
CYP2C19-substrate:	0.278
CYP2C9-inhibitor:	0.007
CYP2C9-substrate:	0.03
CYP2D6-inhibitor:	0.005
CYP2D6-substrate:	0.127
CYP3A4-inhibitor:	0.102
CYP3A4-substrate:	0.21

ADMET: Excretion

Clearance (CL):	2.479
Half-life (T1/2):	0.203

ADMET: Toxicity

hERG Blockers:	0.033
Human Hepatotoxicity (H-HT):	0.478
Drug-inuced Liver Injury (DILI):	0.656
AMES Toxicity:	0.102
Rat Oral Acute Toxicity:	0.929
Maximum Recommended Daily Dose:	0.949
Skin Sensitization:	0.363
Carcinogencity:	0.593
Eye Corrosion:	0.073
Eye Irritation:	0.048
Respiratory Toxicity:	0.983

Download Data

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

Natural Product: NPC51957

Natural Product ID:	NPC51957
*Common Name:**	Hydron;2,3,9,10-Tetramethoxy-6,8,13,13A-Tetrahydro-5H-Isoquinolino[2,1-B]Isoquinoline;Chloride
IUPAC Name:	hydron;2,3,9,10-tetramethoxy-6,8,13,13a-tetrahydro-5H-isoquinolino[2,1-b]isoquinoline;chloride
Synonyms:
Standard InCHIKey:	MGSZZQQRTPWMEI-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C21H25NO4.ClH/c1-23-18-6-5-13-9-17-15-11-20(25-3)19(24-2)10-14(15)7-8-22(17)12-16(13)21(18)26-4;/h5-6,10-11,17H,7-9,12H2,1-4H3;1H
SMILES:	COc1cc2CCN3C(c2cc1OC)Cc1c(C3)c(OC)c(cc1)OC.Cl
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1412574
PubChem CID:	645223 17265 6602555
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0001909] Protoberberine alkaloids 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
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	root	n.a.	PMID[16441081]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16675659]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22074222]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	root	n.a.	PMID[22074222]
NPO827	Corydalis yanhusuo	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22737858]
NPO827	Corydalis yanhusuo	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23194502]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	root	n.a.	PMID[23867078]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	rhizome	n.a.	PMID[23867078]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24479468]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	roots	n.a.	n.a.	PMID[24957203]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25445757]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25744461]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26841168]
NPO14045	Corydalis decumbens	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31599578]
NPO827	Corydalis yanhusuo	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32058719]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32196343]
NPO827	Corydalis yanhusuo	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14045	Corydalis decumbens	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22242.1	Phellodendron chinense var. glabriusculum	Varieties	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28372	Corydalis pallida	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1045	Corydalis racemosa	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14368	Stephania sinica	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24476	Phellodendron amurense	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28698	Corydalis remota	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22242	Phellodendron chinense	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1045	Corydalis racemosa	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO827	Corydalis yanhusuo	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14045	Corydalis decumbens	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22242	Phellodendron chinense	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24476	Phellodendron amurense	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14368	Stephania sinica	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28698	Corydalis remota	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22242.1	Phellodendron chinense var. glabriusculum	Varieties	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28372	Corydalis pallida	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28372	Corydalis pallida	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO827	Corydalis yanhusuo	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO24476	Phellodendron amurense	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO28698	Corydalis remota	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO22242	Phellodendron chinense	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO14045	Corydalis decumbens	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO827	Corydalis yanhusuo	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO26538	Phellodendron chinese	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO24476	Phellodendron amurense	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO14045	Corydalis decumbens	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO22242	Phellodendron chinense	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28372	Corydalis pallida	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14045	Corydalis decumbens	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24476	Phellodendron amurense	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28698	Corydalis remota	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22242	Phellodendron chinense	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1045	Corydalis racemosa	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO827	Corydalis yanhusuo	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14368	Stephania sinica	Species	Menispermaceae	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
Potency	14

Activity Type	# Activity
Cell Line	1
Individual Protein	9
Organism	2
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT483	Individual Protein	Prelamin-A/C	Homo sapiens	Potency	=	14125.4	nM	PMID[463762]
NPT210	Individual Protein	Thyroid stimulating hormone receptor	Homo sapiens	Potency	=	39810.7	nM	PMID[463762]
NPT150	Individual Protein	Anthrax lethal factor	Bacillus anthracis	Potency	=	3981.1	nM	PMID[463762]
NPT152	Individual Protein	Nuclear factor erythroid 2-related factor 2	Homo sapiens	Potency	n.a.	11582.1	nM	PMID[463762]
NPT64	Individual Protein	ATPase family AAA domain-containing protein 5	Homo sapiens	Potency	n.a.	18356.4	nM	PMID[463762]
NPT65	Cell Line	HepG2	Homo sapiens	Potency	n.a.	5623.4	nM	PMID[463762]
NPT50	Individual Protein	Tyrosyl-DNA phosphodiesterase 1	Homo sapiens	Potency	n.a.	7307.8	nM	PMID[463762]
NPT50	Individual Protein	Tyrosyl-DNA phosphodiesterase 1	Homo sapiens	Potency	n.a.	25929.0	nM	PMID[463762]
NPT105	Individual Protein	Muscleblind-like protein 1	Homo sapiens	Potency	n.a.	8912.5	nM	PMID[463762]
NPT2	Others	Unspecified		Potency	=	29092.9	nM	PMID[463762]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Potency	n.a.	18526.0	nM	PMID[463762]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Potency	n.a.	1311.5	nM	PMID[463762]
NPT2	Others	Unspecified		Potency	n.a.	31622.8	nM	PMID[463762]

☑ 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 NPC51957 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	333
0.1-0.2	1739
0.2-0.3	10097
0.3-0.4	7725
0.4-0.5	6792
0.5-0.6	11846
0.6-0.7	3257
0.7-0.8	483
0.8-0.85	249
0.85-0.9	121
0.9-0.95	46
0.95-1	9

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC106295
1.0	High Similarity	NPC210437
1.0	High Similarity	NPC476144
1.0	High Similarity	NPC16107
0.9928	High Similarity	NPC7467
0.971	High Similarity	NPC128019
0.971	High Similarity	NPC136860
0.971	High Similarity	NPC476567
0.9565	High Similarity	NPC188163
0.9565	High Similarity	NPC474915
0.9565	High Similarity	NPC213206
0.9565	High Similarity	NPC328750
0.9517	High Similarity	NPC41178
0.9517	High Similarity	NPC193949
0.9517	High Similarity	NPC184026
0.9517	High Similarity	NPC276588
0.9517	High Similarity	NPC2413
0.9517	High Similarity	NPC5238
0.9517	High Similarity	NPC39701
0.9517	High Similarity	NPC216459
0.9517	High Similarity	NPC138487
0.9517	High Similarity	NPC295691
0.9517	High Similarity	NPC189266
0.9517	High Similarity	NPC110416
0.9517	High Similarity	NPC249797
0.9517	High Similarity	NPC54379
0.9517	High Similarity	NPC204828
0.9517	High Similarity	NPC278799
0.9517	High Similarity	NPC207757
0.9517	High Similarity	NPC172765
0.9517	High Similarity	NPC469817
0.9517	High Similarity	NPC127674
0.9493	High Similarity	NPC314682
0.9452	High Similarity	NPC146288
0.932	High Similarity	NPC234392
0.932	High Similarity	NPC31311
0.9301	High Similarity	NPC476151
0.9241	High Similarity	NPC192768
0.9241	High Similarity	NPC97221
0.9241	High Similarity	NPC151895
0.9241	High Similarity	NPC220858
0.9241	High Similarity	NPC88249
0.9178	High Similarity	NPC326316
0.9178	High Similarity	NPC81733
0.9172	High Similarity	NPC103379
0.9172	High Similarity	NPC477565
0.9161	High Similarity	NPC185838
0.9116	High Similarity	NPC210148
0.9116	High Similarity	NPC233029
0.9103	High Similarity	NPC475959
0.9103	High Similarity	NPC147390
0.9103	High Similarity	NPC246587
0.9103	High Similarity	NPC135538
0.9103	High Similarity	NPC428
0.9103	High Similarity	NPC24233
0.9103	High Similarity	NPC476571
0.9079	High Similarity	NPC238530
0.9079	High Similarity	NPC276944
0.9079	High Similarity	NPC232514
0.906	High Similarity	NPC25084
0.906	High Similarity	NPC247639
0.9041	High Similarity	NPC92541
0.9034	High Similarity	NPC191376
0.9034	High Similarity	NPC321505
0.9034	High Similarity	NPC179825
0.902	High Similarity	NPC264850
0.902	High Similarity	NPC13916
0.9	High Similarity	NPC476572
0.8993	High Similarity	NPC325871
0.8993	High Similarity	NPC80129
0.8993	High Similarity	NPC99659
0.8993	High Similarity	NPC187022
0.8954	High Similarity	NPC24465
0.8919	High Similarity	NPC476579
0.8919	High Similarity	NPC476568
0.8904	High Similarity	NPC144863
0.8897	High Similarity	NPC130926
0.8867	High Similarity	NPC93593
0.8841	High Similarity	NPC160193
0.8816	High Similarity	NPC111485
0.8816	High Similarity	NPC216816
0.8808	High Similarity	NPC203784
0.8808	High Similarity	NPC170503
0.8808	High Similarity	NPC126519
0.88	High Similarity	NPC2295
0.88	High Similarity	NPC477564
0.879	High Similarity	NPC317145
0.879	High Similarity	NPC10908
0.879	High Similarity	NPC76682
0.879	High Similarity	NPC198498
0.879	High Similarity	NPC276890
0.879	High Similarity	NPC115284
0.879	High Similarity	NPC63646
0.879	High Similarity	NPC317439
0.879	High Similarity	NPC227060
0.8784	High Similarity	NPC219162
0.8784	High Similarity	NPC207824
0.8784	High Similarity	NPC60538
0.8766	High Similarity	NPC475393
0.8758	High Similarity	NPC266753
0.8758	High Similarity	NPC160298
0.8758	High Similarity	NPC306902
0.8758	High Similarity	NPC27410
0.8758	High Similarity	NPC166014
0.8758	High Similarity	NPC232924
0.8758	High Similarity	NPC477559
0.8742	High Similarity	NPC244112
0.8734	High Similarity	NPC251580
0.8734	High Similarity	NPC2314
0.8734	High Similarity	NPC12424
0.8734	High Similarity	NPC129518
0.8734	High Similarity	NPC41376
0.8716	High Similarity	NPC130941
0.8696	High Similarity	NPC172403
0.8693	High Similarity	NPC477080
0.8671	High Similarity	NPC253429
0.8667	High Similarity	NPC76213
0.8667	High Similarity	NPC277669
0.8654	High Similarity	NPC24264
0.8654	High Similarity	NPC250846
0.8654	High Similarity	NPC256012
0.8654	High Similarity	NPC42549
0.8654	High Similarity	NPC268503
0.8654	High Similarity	NPC240841
0.8654	High Similarity	NPC476432
0.8654	High Similarity	NPC317272
0.8649	High Similarity	NPC253883
0.8649	High Similarity	NPC90844
0.8649	High Similarity	NPC95075
0.8645	High Similarity	NPC324144
0.8625	High Similarity	NPC241704
0.8625	High Similarity	NPC293093
0.8625	High Similarity	NPC222524
0.8609	High Similarity	NPC470924
0.8609	High Similarity	NPC37272
0.86	High Similarity	NPC274026
0.8599	High Similarity	NPC205421
0.8599	High Similarity	NPC474931
0.8599	High Similarity	NPC306555
0.8599	High Similarity	NPC158376
0.8599	High Similarity	NPC81218
0.8599	High Similarity	NPC145832
0.8599	High Similarity	NPC247389
0.8599	High Similarity	NPC12053
0.8599	High Similarity	NPC117188
0.859	High Similarity	NPC212794
0.859	High Similarity	NPC96603
0.859	High Similarity	NPC225774
0.859	High Similarity	NPC196447
0.859	High Similarity	NPC136508
0.859	High Similarity	NPC121275
0.859	High Similarity	NPC477563
0.859	High Similarity	NPC13504
0.859	High Similarity	NPC302527
0.859	High Similarity	NPC16805
0.859	High Similarity	NPC284183
0.859	High Similarity	NPC306843
0.859	High Similarity	NPC167546
0.859	High Similarity	NPC253043
0.859	High Similarity	NPC78222
0.859	High Similarity	NPC4138
0.8581	High Similarity	NPC60186
0.8544	High Similarity	NPC83198
0.8544	High Similarity	NPC204908
0.8535	High Similarity	NPC219341
0.8531	High Similarity	NPC11147
0.8519	High Similarity	NPC243454
0.8519	High Similarity	NPC32154
0.8519	High Similarity	NPC475479
0.8497	Intermediate Similarity	NPC78733
0.8493	Intermediate Similarity	NPC470925
0.8487	Intermediate Similarity	NPC82285
0.8487	Intermediate Similarity	NPC148898
0.8487	Intermediate Similarity	NPC133011
0.8481	Intermediate Similarity	NPC298979
0.8481	Intermediate Similarity	NPC210918
0.8466	Intermediate Similarity	NPC239584
0.8452	Intermediate Similarity	NPC118804
0.8452	Intermediate Similarity	NPC106786
0.8442	Intermediate Similarity	NPC323443
0.8442	Intermediate Similarity	NPC147091
0.8442	Intermediate Similarity	NPC180756
0.8428	Intermediate Similarity	NPC241055
0.8428	Intermediate Similarity	NPC66573
0.8418	Intermediate Similarity	NPC304659
0.8418	Intermediate Similarity	NPC86144
0.8418	Intermediate Similarity	NPC476573
0.8418	Intermediate Similarity	NPC81247
0.8418	Intermediate Similarity	NPC35627
0.8415	Intermediate Similarity	NPC8836
0.8415	Intermediate Similarity	NPC15414
0.8415	Intermediate Similarity	NPC42663
0.8415	Intermediate Similarity	NPC328155
0.8415	Intermediate Similarity	NPC271013
0.8415	Intermediate Similarity	NPC251735
0.8415	Intermediate Similarity	NPC299990
0.8415	Intermediate Similarity	NPC182052
0.8415	Intermediate Similarity	NPC279228
0.8415	Intermediate Similarity	NPC54654
0.8415	Intermediate Similarity	NPC222661

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 NPC51957 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	202
0.1-0.2	770
0.2-0.3	1050
0.3-0.4	1713
0.4-0.5	2697
0.5-0.6	1805
0.6-0.7	684
0.7-0.8	195
0.8-0.85	26
0.85-0.9	6
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
1.0	High Similarity	NPD4584	Approved
0.9565	High Similarity	NPD4664	Clinical (unspecified phase)
0.8993	High Similarity	NPD7298	Approved
0.8792	High Similarity	NPD4017	Approved
0.879	High Similarity	NPD8099	Discontinued
0.879	High Similarity	NPD8251	Approved
0.879	High Similarity	NPD8252	Approved
0.8784	High Similarity	NPD3640	Phase 3
0.8784	High Similarity	NPD3639	Approved
0.8784	High Similarity	NPD3641	Approved
0.8734	High Similarity	NPD8156	Discontinued
0.8675	High Similarity	NPD4773	Phase 2
0.8675	High Similarity	NPD4772	Phase 2
0.8671	High Similarity	NPD6029	Clinical (unspecified phase)
0.8671	High Similarity	NPD6028	Clinical (unspecified phase)
0.8533	High Similarity	NPD6030	Approved
0.8533	High Similarity	NPD6031	Approved
0.8452	Intermediate Similarity	NPD6788	Approved
0.8415	Intermediate Similarity	NPD8054	Approved
0.8415	Intermediate Similarity	NPD8053	Approved
0.8408	Intermediate Similarity	NPD7201	Clinical (unspecified phase)
0.838	Intermediate Similarity	NPD5718	Phase 2
0.8354	Intermediate Similarity	NPD6107	Approved
0.8333	Intermediate Similarity	NPD3124	Discontinued
0.831	Intermediate Similarity	NPD2669	Clinical (unspecified phase)
0.82	Intermediate Similarity	NPD5241	Discontinued
0.8187	Intermediate Similarity	NPD4010	Discontinued
0.8125	Intermediate Similarity	NPD7802	Discontinued
0.8112	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.8095	Intermediate Similarity	NPD6895	Approved
0.8095	Intermediate Similarity	NPD6896	Approved
0.8089	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.8086	Intermediate Similarity	NPD2898	Approved
0.8079	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.8075	Intermediate Similarity	NPD4166	Phase 2
0.8069	Intermediate Similarity	NPD4474	Approved
0.8069	Intermediate Similarity	NPD4475	Approved
0.8049	Intermediate Similarity	NPD5312	Approved
0.8049	Intermediate Similarity	NPD5313	Approved
0.8039	Intermediate Similarity	NPD1754	Clinical (unspecified phase)
0.7975	Intermediate Similarity	NPD4481	Phase 3
0.7974	Intermediate Similarity	NPD2420	Approved
0.7974	Intermediate Similarity	NPD2421	Approved
0.7974	Intermediate Similarity	NPD7598	Phase 2
0.7963	Intermediate Similarity	NPD3051	Approved
0.7937	Intermediate Similarity	NPD7831	Phase 2
0.7937	Intermediate Similarity	NPD7833	Phase 2
0.7937	Intermediate Similarity	NPD7832	Clinical (unspecified phase)
0.7927	Intermediate Similarity	NPD5602	Clinical (unspecified phase)
0.7922	Intermediate Similarity	NPD1424	Approved
0.7914	Intermediate Similarity	NPD2969	Approved
0.7914	Intermediate Similarity	NPD2970	Approved
0.7908	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.7895	Intermediate Similarity	NPD6748	Discontinued
0.7891	Intermediate Similarity	NPD3110	Approved
0.7891	Intermediate Similarity	NPD3109	Approved
0.7881	Intermediate Similarity	NPD7045	Clinical (unspecified phase)
0.7866	Intermediate Similarity	NPD27	Approved
0.7866	Intermediate Similarity	NPD2489	Approved
0.7853	Intermediate Similarity	NPD6071	Discontinued
0.7844	Intermediate Similarity	NPD6297	Approved
0.7843	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7841	Intermediate Similarity	NPD8095	Phase 1
0.7834	Intermediate Similarity	NPD7261	Clinical (unspecified phase)
0.7829	Intermediate Similarity	NPD5177	Phase 3
0.7812	Intermediate Similarity	NPD5978	Approved
0.7812	Intermediate Similarity	NPD2560	Approved
0.7812	Intermediate Similarity	NPD2563	Approved
0.7812	Intermediate Similarity	NPD5977	Approved
0.7778	Intermediate Similarity	NPD3977	Clinical (unspecified phase)
0.7756	Intermediate Similarity	NPD3647	Clinical (unspecified phase)
0.7748	Intermediate Similarity	NPD1632	Clinical (unspecified phase)
0.7736	Intermediate Similarity	NPD7110	Phase 1
0.7736	Intermediate Similarity	NPD7109	Clinical (unspecified phase)
0.7716	Intermediate Similarity	NPD4055	Discovery
0.7677	Intermediate Similarity	NPD7124	Phase 2
0.7677	Intermediate Similarity	NPD3845	Phase 1
0.767	Intermediate Similarity	NPD7667	Clinical (unspecified phase)
0.7662	Intermediate Similarity	NPD6658	Clinical (unspecified phase)
0.7661	Intermediate Similarity	NPD6853	Approved
0.7661	Intermediate Similarity	NPD6851	Approved
0.7661	Intermediate Similarity	NPD6618	Phase 2
0.7597	Intermediate Similarity	NPD4162	Approved
0.7595	Intermediate Similarity	NPD6662	Clinical (unspecified phase)
0.759	Intermediate Similarity	NPD6688	Approved
0.759	Intermediate Similarity	NPD6687	Approved
0.7586	Intermediate Similarity	NPD7258	Clinical (unspecified phase)
0.7564	Intermediate Similarity	NPD2422	Clinical (unspecified phase)
0.7546	Intermediate Similarity	NPD4581	Clinical (unspecified phase)
0.7544	Intermediate Similarity	NPD8453	Clinical (unspecified phase)
0.7534	Intermediate Similarity	NPD4098	Discontinued
0.7529	Intermediate Similarity	NPD7906	Approved
0.7529	Intermediate Similarity	NPD7291	Discontinued
0.75	Intermediate Similarity	NPD2971	Approved
0.75	Intermediate Similarity	NPD7313	Approved
0.75	Intermediate Similarity	NPD7311	Approved
0.75	Intermediate Similarity	NPD3534	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7312	Approved
0.75	Intermediate Similarity	NPD5917	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD2968	Approved
0.75	Intermediate Similarity	NPD7310	Approved
0.7486	Intermediate Similarity	NPD4420	Approved
0.7484	Intermediate Similarity	NPD4237	Approved
0.7484	Intermediate Similarity	NPD3060	Approved
0.7484	Intermediate Similarity	NPD4236	Phase 3
0.7483	Intermediate Similarity	NPD7905	Discontinued
0.7483	Intermediate Similarity	NPD2668	Approved
0.7483	Intermediate Similarity	NPD2667	Approved
0.7482	Intermediate Similarity	NPD5283	Phase 1
0.7467	Intermediate Similarity	NPD2674	Phase 3
0.7467	Intermediate Similarity	NPD554	Clinical (unspecified phase)
0.7457	Intermediate Similarity	NPD7309	Approved
0.7453	Intermediate Similarity	NPD6876	Approved
0.7453	Intermediate Similarity	NPD6875	Approved
0.7451	Intermediate Similarity	NPD1753	Discontinued
0.7448	Intermediate Similarity	NPD2230	Approved
0.7448	Intermediate Similarity	NPD2232	Approved
0.7448	Intermediate Similarity	NPD2233	Approved
0.7436	Intermediate Similarity	NPD5754	Discontinued
0.7421	Intermediate Similarity	NPD6090	Discontinued
0.7418	Intermediate Similarity	NPD5006	Approved
0.7418	Intermediate Similarity	NPD5005	Approved
0.741	Intermediate Similarity	NPD5677	Discontinued
0.74	Intermediate Similarity	NPD6812	Clinical (unspecified phase)
0.7399	Intermediate Similarity	NPD7281	Phase 3
0.7399	Intermediate Similarity	NPD7280	Phase 3
0.7399	Intermediate Similarity	NPD4578	Approved
0.7399	Intermediate Similarity	NPD4577	Approved
0.7391	Intermediate Similarity	NPD4005	Discontinued
0.7389	Intermediate Similarity	NPD5160	Discontinued
0.7389	Intermediate Similarity	NPD3692	Discontinued
0.7375	Intermediate Similarity	NPD5976	Discontinued
0.7371	Intermediate Similarity	NPD4663	Approved
0.7368	Intermediate Similarity	NPD3920	Phase 2
0.7362	Intermediate Similarity	NPD5720	Discontinued
0.7362	Intermediate Similarity	NPD7945	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD4498	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD5708	Clinical (unspecified phase)
0.7351	Intermediate Similarity	NPD3530	Approved
0.7351	Intermediate Similarity	NPD3532	Approved
0.7351	Intermediate Similarity	NPD3531	Approved
0.7346	Intermediate Similarity	NPD1337	Clinical (unspecified phase)
0.7341	Intermediate Similarity	NPD7132	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD4579	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD4585	Approved
0.7314	Intermediate Similarity	NPD5087	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD3923	Approved
0.7303	Intermediate Similarity	NPD3921	Approved
0.7303	Intermediate Similarity	NPD3922	Approved
0.7303	Intermediate Similarity	NPD3924	Approved
0.7303	Intermediate Similarity	NPD2238	Phase 2
0.7292	Intermediate Similarity	NPD3445	Approved
0.7292	Intermediate Similarity	NPD3444	Approved
0.7292	Intermediate Similarity	NPD3443	Approved
0.7285	Intermediate Similarity	NPD5111	Phase 2
0.7285	Intermediate Similarity	NPD5110	Phase 2
0.7285	Intermediate Similarity	NPD3144	Approved
0.7285	Intermediate Similarity	NPD3145	Approved
0.7285	Intermediate Similarity	NPD5109	Approved
0.7279	Intermediate Similarity	NPD1420	Approved
0.7279	Intermediate Similarity	NPD1421	Approved
0.7279	Intermediate Similarity	NPD1669	Approved
0.7273	Intermediate Similarity	NPD2200	Suspended
0.7267	Intermediate Similarity	NPD4727	Phase 1
0.7267	Intermediate Similarity	NPD1914	Approved
0.7267	Intermediate Similarity	NPD2122	Discontinued
0.725	Intermediate Similarity	NPD4123	Phase 3
0.7249	Intermediate Similarity	NPD3815	Phase 1
0.7249	Intermediate Similarity	NPD3816	Phase 1
0.7247	Intermediate Similarity	NPD5525	Clinical (unspecified phase)
0.7247	Intermediate Similarity	NPD2490	Approved
0.7247	Intermediate Similarity	NPD2488	Approved
0.7246	Intermediate Similarity	NPD7400	Phase 3
0.7244	Intermediate Similarity	NPD3656	Approved
0.7238	Intermediate Similarity	NPD7034	Discontinued
0.723	Intermediate Similarity	NPD2922	Phase 1
0.7226	Intermediate Similarity	NPD2156	Approved
0.7226	Intermediate Similarity	NPD2155	Approved
0.7226	Intermediate Similarity	NPD2154	Approved
0.7225	Intermediate Similarity	NPD6996	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD2486	Discontinued
0.7222	Intermediate Similarity	NPD4210	Discontinued
0.7215	Intermediate Similarity	NPD6331	Phase 2
0.7212	Intermediate Similarity	NPD5773	Approved
0.7212	Intermediate Similarity	NPD2978	Approved
0.7212	Intermediate Similarity	NPD5772	Approved
0.7212	Intermediate Similarity	NPD2977	Approved
0.7208	Intermediate Similarity	NPD2492	Phase 1
0.7208	Intermediate Similarity	NPD2989	Phase 2
0.7208	Intermediate Similarity	NPD2986	Phase 2
0.7208	Intermediate Similarity	NPD2653	Approved
0.7197	Intermediate Similarity	NPD1372	Clinical (unspecified phase)
0.7195	Intermediate Similarity	NPD6386	Approved
0.7195	Intermediate Similarity	NPD6385	Approved
0.7193	Intermediate Similarity	NPD5938	Phase 3
0.7192	Intermediate Similarity	NPD3294	Phase 2
0.7178	Intermediate Similarity	NPD6357	Discontinued
0.7172	Intermediate Similarity	NPD2594	Approved
0.7172	Intermediate Similarity	NPD2595	Approved
0.7161	Intermediate Similarity	NPD6111	Discontinued

Bioactivity similarity: Similar Natural Products in NPASS

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

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

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data