NPASS Compound

Structure

CID26240 OpenBabel06191715352D 23 26 0 0 1 0 0 0 0 0999 V2000 -3.3808 -0.0516 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7796 0.3373 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5070 -1.4377 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5112 -2.3963 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0068 -2.8984 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6612 0.0100 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6528 -2.9219 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6884 -0.9809 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6683 -0.9535 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8212 -2.4212 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8390 -1.4507 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8402 -2.4115 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5021 -2.4520 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8285 0.4840 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5199 -1.4816 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8398 -1.4375 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0056 -0.9638 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6827 -2.8803 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -3.3277 -2.9491 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8230 1.4492 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3632 -1.0151 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8308 0.4800 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 4 1 0 0 0 0 3 9 1 0 0 0 0 4 19 1 0 0 0 0 5 10 1 0 0 0 0 6 9 2 0 0 0 0 6 14 1 0 0 0 0 7 10 2 0 0 0 0 7 13 1 0 0 0 0 8 11 2 0 0 0 0 8 15 1 0 0 0 0 9 16 1 0 0 0 0 10 11 1 0 0 0 0 11 17 1 0 0 0 0 12 5 1 1 0 0 0 12 16 1 0 0 0 0 12 19 1 0 0 0 0 13 15 2 0 0 0 0 13 20 1 0 0 0 0 14 18 2 0 0 0 0 14 21 1 0 0 0 0 15 22 1 0 0 0 0 16 17 2 0 0 0 0 17 18 1 0 0 0 0 18 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	313.13
Volume:	315.997
LogP:	0.725
LogD:	2.388
LogS:	-1.696
# Rotatable Bonds:	2
TPSA:	70.95
# H-Bond Aceptor:	5
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.795
Synthetic Accessibility Score:	3.254
Fsp3:	0.333
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.298
MDCK Permeability:	1.0692410796764307e-05
Pgp-inhibitor:	0.015
Pgp-substrate:	0.985
Human Intestinal Absorption (HIA):	0.014
20% Bioavailability (F20%):	0.422
30% Bioavailability (F30%):	0.019

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.542
Plasma Protein Binding (PPB):	71.52494812011719%
Volume Distribution (VD):	1.707
Pgp-substrate:	19.80805778503418%

ADMET: Metabolism

CYP1A2-inhibitor:	0.659
CYP1A2-substrate:	0.905
CYP2C19-inhibitor:	0.04
CYP2C19-substrate:	0.515
CYP2C9-inhibitor:	0.01
CYP2C9-substrate:	0.587
CYP2D6-inhibitor:	0.32
CYP2D6-substrate:	0.904
CYP3A4-inhibitor:	0.062
CYP3A4-substrate:	0.751

ADMET: Excretion

Clearance (CL):	8.613
Half-life (T1/2):	0.692

ADMET: Toxicity

hERG Blockers:	0.598
Human Hepatotoxicity (H-HT):	0.234
Drug-inuced Liver Injury (DILI):	0.41
AMES Toxicity:	0.559
Rat Oral Acute Toxicity:	0.677
Maximum Recommended Daily Dose:	0.98
Skin Sensitization:	0.814
Carcinogencity:	0.05
Eye Corrosion:	0.003
Eye Irritation:	0.011
Respiratory Toxicity:	0.938

Download Data

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

Natural Product: NPC26240

Natural Product ID:	NPC26240
*Common Name:**	Norboldine
IUPAC Name:	(6aS)-1,10-dimethoxy-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinoline-2,9-diol
Synonyms:	(+)-Norboldine; Laurolistine; Laurolitsine
Standard InCHIKey:	KYVJVURXKAZJRK-LBPRGKRZSA-N
Standard InCHI:	InChI=1S/C18H19NO4/c1-22-15-8-11-10(7-13(15)20)5-12-16-9(3-4-19-12)6-14(21)18(23-2)17(11)16/h6-8,12,19-21H,3-5H2,1-2H3/t12-/m0/s1
SMILES:	COc1cc2c(cc1O)C[C@H]1c3c2c(OC)c(O)cc3CCN1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL487388
PubChem CID:	22179
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0000381] Aporphines

*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
NPO5852	Litsea glutinosa	Species	Lauraceae	Eukaryota	n.a.	stem	n.a.	DOI[10.1016/S0031-9422(00)88469-1]
NPO5852	Litsea glutinosa	Species	Lauraceae	Eukaryota	n.a.	leaf	n.a.	DOI[10.1016/S0031-9422(00)88469-1]
NPO12553	Lindera chunii	Species	Lauraceae	Eukaryota	n.a.	root	n.a.	PMID[12237535]
NPO27883	Bursera simaruba	Species	Burseraceae	Eukaryota	Resin	n.a.	n.a.	PMID[1294696]
NPO11093	Pseudobersama mossambicensis	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1479381]
NPO28935	Ericameria laricifolia	Species	Asteraceae	Eukaryota	n.a.	Sonoran Desert	n.a.	PMID[15043404]
NPO4682	Lindera aggregata	Species	Lauraceae	Eukaryota	n.a.	leaf	n.a.	PMID[17999353]
NPO29110	Litsea cubeba	Species	Lauraceae	Eukaryota	n.a.	aerial part	n.a.	PMID[18991207]
NPO23557	Zanthoxylum ailanthoides	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19128011]
NPO27883	Bursera simaruba	Species	Burseraceae	Eukaryota	n.a.	bark	n.a.	PMID[19329133]
NPO4682	Lindera aggregata	Species	Lauraceae	Eukaryota	Roots; Tubers	n.a.	n.a.	PMID[19639966]
NPO29110	Litsea cubeba	Species	Lauraceae	Eukaryota	essential oil	Tibet	n.a.	PMID[20944522]
NPO6701	Cinnamomum camphora	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25612070]
NPO29110	Litsea cubeba	Species	Lauraceae	Eukaryota	Twigs	n.a.	n.a.	PMID[28541690]
NPO32838	artabottys maingayi	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[8676127]
NPO32610	nectandra salicifolia	Species	Lauraceae	Eukaryota	trunk bark	lower montane rainforest in Costa Rica	n.a.	PMID[8786363]
NPO27903	Delphinium denudatum	Species	Ranunculaceae	Eukaryota	n.a.	root	n.a.	PMID[9170290]
NPO6701	Cinnamomum camphora	Species	Lauraceae	Eukaryota	n.a.	stem	n.a.	Database[Article]
NPO31274	Lindera strychnifolia	Species	Tineidae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9970	Siparuna pauciflora	Species	Siparunaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23557	Zanthoxylum ailanthoides	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18237	Zanthoxylum elephantiasis	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5852	Litsea glutinosa	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21807	Lindera umbellata	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO6701	Cinnamomum camphora	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO27724	Polygala senega	Species	Polygalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29110	Litsea cubeba	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12553	Lindera chunii	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO27912	Cocculus laurifolius	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26851	Eupatorium rebaudianum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO27903	Delphinium denudatum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5852	Litsea glutinosa	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18237	Zanthoxylum elephantiasis	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23557	Zanthoxylum ailanthoides	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9970	Siparuna pauciflora	Species	Siparunaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6701	Cinnamomum camphora	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29110	Litsea cubeba	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4682	Lindera aggregata	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12553	Lindera chunii	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18780	Diplacus aurantiacus	Species	Phrymaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27912	Cocculus laurifolius	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21807	Lindera umbellata	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26851	Eupatorium rebaudianum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27724	Polygala senega	Species	Polygalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6696	Chukrasia tabularis	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27903	Delphinium denudatum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1079	Vachellia karroo	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6701	Cinnamomum camphora	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO27912	Cocculus laurifolius	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO27724	Polygala senega	Species	Polygalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO30415	Lindera aggregate	Species	Tineidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO21807	Lindera umbellata	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO31274	Lindera strychnifolia	Species	Tineidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO4682	Lindera aggregata	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO13346	Lindera strichnifolia	Species	Tineidae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO27724	Polygala senega	Species	Polygalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO29110	Litsea cubeba	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO29307	Loranthus longiflorus	Species	Loranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27883	Bursera simaruba	Species	Burseraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6696	Chukrasia tabularis	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12553	Lindera chunii	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27724	Polygala senega	Species	Polygalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29218	Ramalina farinacea	Species	Ramalinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28549	Mentha incana	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11093	Pseudobersama mossambicensis	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16079	Cephalaria leucantha	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27256	Solanum boerhaavii	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29110	Litsea cubeba	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4682	Lindera aggregata	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27912	Cocculus laurifolius	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5852	Litsea glutinosa	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18237	Zanthoxylum elephantiasis	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23557	Zanthoxylum ailanthoides	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27562	Coleus wulfenioides	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29411	Streptomyces nigrescens	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO9970	Siparuna pauciflora	Species	Siparunaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29144	Ormosia fordiana	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6701	Cinnamomum camphora	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28935	Ericameria laricifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26851	Eupatorium rebaudianum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27903	Delphinium denudatum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26549	Polanisia trachysperma	Species	Cleomaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21807	Lindera umbellata	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28959	Cissus quadrangularis	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1079	Vachellia karroo	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO862	Podocarpus elatus	Species	Podocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29377	Callistemon speciosus	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18780	Diplacus aurantiacus	Species	Phrymaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4228	Wickerhamomyces anomalus	Species	Phaffomycetaceae	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
ED50	1
IC50	6
Others	5

Activity Type	# Activity
Cell Line	2
Individual Protein	4
Organism	3
Others	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1857	Individual Protein	Dopamine D1 receptor	Rattus norvegicus	IC50	=	2500.0	nM	PMID[465178]
NPT1858	Individual Protein	Dopamine D2 receptor	Rattus norvegicus	IC50	=	6800.0	nM	PMID[465178]
NPT1073	Individual Protein	Dopamine transporter	Rattus norvegicus	IC50	=	16500.0	nM	PMID[465178]
NPT1073	Individual Protein	Dopamine transporter	Rattus norvegicus	IC50	=	16500.0	nM	PMID[465181]
NPT189	Cell Line	Vero	Chlorocebus aethiops	CC50	=	95000.0	nM	PMID[465182]
NPT189	Cell Line	Vero	Chlorocebus aethiops	MTC	=	62.0	uM	PMID[465182]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	1.24	ug.mL-1	PMID[465180]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	1.68	ug.mL-1	PMID[465180]
NPT2	Others	Unspecified		Ratio IC50	=	0.15	n.a.	PMID[465181]
NPT2	Others	Unspecified		Ratio IC50	=	0.41	n.a.	PMID[465181]
NPT1859	Organism	Human poliovirus 2	Human poliovirus 2	ED50	=	62.0	uM	PMID[465182]
NPT2	Others	Unspecified		Ratio	=	1.5	n.a.	PMID[465182]

☑ 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 NPC26240 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	324
0.1-0.2	1729
0.2-0.3	8268
0.3-0.4	9854
0.4-0.5	5946
0.5-0.6	11461
0.6-0.7	4065
0.7-0.8	650
0.8-0.85	228
0.85-0.9	110
0.9-0.95	44
0.95-1	18

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC477562
1.0	High Similarity	NPC69712
0.9873	High Similarity	NPC192135
0.9873	High Similarity	NPC66341
0.9873	High Similarity	NPC477020
0.9682	High Similarity	NPC35627
0.9682	High Similarity	NPC476573
0.9682	High Similarity	NPC81247
0.963	High Similarity	NPC474507
0.9618	High Similarity	NPC253043
0.9618	High Similarity	NPC136508
0.9618	High Similarity	NPC78222
0.9618	High Similarity	NPC212794
0.9618	High Similarity	NPC96603
0.9618	High Similarity	NPC196447
0.9618	High Similarity	NPC477563
0.9618	High Similarity	NPC13504
0.9618	High Similarity	NPC306843
0.9571	High Similarity	NPC312918
0.9571	High Similarity	NPC476574
0.9571	High Similarity	NPC477561
0.9571	High Similarity	NPC155442
0.9554	High Similarity	NPC324144
0.9506	High Similarity	NPC173416
0.9506	High Similarity	NPC148709
0.9506	High Similarity	NPC476577
0.9497	High Similarity	NPC145832
0.9497	High Similarity	NPC474931
0.9497	High Similarity	NPC12053
0.9497	High Similarity	NPC306555
0.9497	High Similarity	NPC158376
0.9497	High Similarity	NPC81218
0.9497	High Similarity	NPC117188
0.9497	High Similarity	NPC205421
0.9455	High Similarity	NPC135772
0.9321	High Similarity	NPC239775
0.9308	High Similarity	NPC1229
0.9304	High Similarity	NPC166014
0.9304	High Similarity	NPC27410
0.9286	High Similarity	NPC476576
0.9286	High Similarity	NPC186546
0.9255	High Similarity	NPC204947
0.9236	High Similarity	NPC203784
0.9236	High Similarity	NPC126519
0.9236	High Similarity	NPC170503
0.9207	High Similarity	NPC128560
0.9207	High Similarity	NPC199465
0.9207	High Similarity	NPC229166
0.9207	High Similarity	NPC477558
0.9172	High Similarity	NPC99659
0.9172	High Similarity	NPC325871
0.9141	High Similarity	NPC6152
0.9141	High Similarity	NPC168753
0.9141	High Similarity	NPC118274
0.9112	High Similarity	NPC57036
0.9096	High Similarity	NPC114364
0.9096	High Similarity	NPC320223
0.9057	High Similarity	NPC476572
0.9024	High Similarity	NPC152212
0.9006	High Similarity	NPC60186
0.8987	High Similarity	NPC477564
0.8987	High Similarity	NPC2295
0.8981	High Similarity	NPC76213
0.8981	High Similarity	NPC277669
0.8976	High Similarity	NPC329969
0.8935	High Similarity	NPC116284
0.8861	High Similarity	NPC326316
0.8861	High Similarity	NPC81733
0.8854	High Similarity	NPC60538
0.8854	High Similarity	NPC207824
0.8844	High Similarity	NPC475754
0.8841	High Similarity	NPC86144
0.8841	High Similarity	NPC304659
0.8824	High Similarity	NPC476575
0.8817	High Similarity	NPC258695
0.8817	High Similarity	NPC470879
0.8788	High Similarity	NPC298979
0.878	High Similarity	NPC167546
0.878	High Similarity	NPC16805
0.878	High Similarity	NPC302527
0.8765	High Similarity	NPC474506
0.8765	High Similarity	NPC32413
0.8757	High Similarity	NPC23219
0.8727	High Similarity	NPC223077
0.8727	High Similarity	NPC476432
0.8727	High Similarity	NPC193853
0.8727	High Similarity	NPC56887
0.8727	High Similarity	NPC24264
0.872	High Similarity	NPC189470
0.8706	High Similarity	NPC267408
0.8698	High Similarity	NPC112575
0.8696	High Similarity	NPC193949
0.8696	High Similarity	NPC207757
0.8696	High Similarity	NPC295691
0.8696	High Similarity	NPC278799
0.8696	High Similarity	NPC54379
0.8696	High Similarity	NPC5238
0.8696	High Similarity	NPC172765
0.8696	High Similarity	NPC204828
0.8696	High Similarity	NPC2413
0.8696	High Similarity	NPC110416
0.8696	High Similarity	NPC127674
0.8696	High Similarity	NPC39701
0.8696	High Similarity	NPC184026
0.8696	High Similarity	NPC469817
0.8696	High Similarity	NPC189266
0.8696	High Similarity	NPC276588
0.8696	High Similarity	NPC249797
0.8686	High Similarity	NPC117717
0.8683	High Similarity	NPC109925
0.8679	High Similarity	NPC151895
0.8679	High Similarity	NPC88249
0.8679	High Similarity	NPC192768
0.8679	High Similarity	NPC97221
0.8679	High Similarity	NPC220858
0.8678	High Similarity	NPC82763
0.8675	High Similarity	NPC247389
0.8675	High Similarity	NPC210918
0.8671	High Similarity	NPC135538
0.8671	High Similarity	NPC24233
0.8671	High Similarity	NPC147390
0.8671	High Similarity	NPC476571
0.8671	High Similarity	NPC246587
0.8671	High Similarity	NPC428
0.8667	High Similarity	NPC24465
0.8667	High Similarity	NPC4138
0.8667	High Similarity	NPC121275
0.8667	High Similarity	NPC209377
0.8667	High Similarity	NPC284183
0.8667	High Similarity	NPC225774
0.8654	High Similarity	NPC294249
0.8642	High Similarity	NPC186063
0.8616	High Similarity	NPC103379
0.8616	High Similarity	NPC477565
0.8614	High Similarity	NPC219341
0.8614	High Similarity	NPC264850
0.8614	High Similarity	NPC13916
0.8614	High Similarity	NPC195392
0.8608	High Similarity	NPC191376
0.8608	High Similarity	NPC321505
0.8608	High Similarity	NPC179825
0.8605	High Similarity	NPC248642
0.8605	High Similarity	NPC275132
0.8596	High Similarity	NPC126284
0.8589	High Similarity	NPC79328
0.858	High Similarity	NPC478093
0.8563	High Similarity	NPC320088
0.8555	High Similarity	NPC156576
0.8531	High Similarity	NPC473589
0.8531	High Similarity	NPC478091
0.8531	High Similarity	NPC478092
0.8531	High Similarity	NPC30182
0.8521	High Similarity	NPC19520
0.8521	High Similarity	NPC108434
0.8521	High Similarity	NPC149090
0.8521	High Similarity	NPC475215
0.8491	Intermediate Similarity	NPC476151
0.8488	Intermediate Similarity	NPC32154
0.8485	Intermediate Similarity	NPC477559
0.8485	Intermediate Similarity	NPC306902
0.8485	Intermediate Similarity	NPC266753
0.8485	Intermediate Similarity	NPC160298
0.8485	Intermediate Similarity	NPC232924
0.8481	Intermediate Similarity	NPC185838
0.8466	Intermediate Similarity	NPC48490
0.8466	Intermediate Similarity	NPC82457
0.8466	Intermediate Similarity	NPC175890
0.8466	Intermediate Similarity	NPC244112
0.8466	Intermediate Similarity	NPC274661
0.8466	Intermediate Similarity	NPC11296
0.8452	Intermediate Similarity	NPC150879
0.8452	Intermediate Similarity	NPC210140
0.8427	Intermediate Similarity	NPC256124
0.8424	Intermediate Similarity	NPC7393
0.8418	Intermediate Similarity	NPC60295
0.8418	Intermediate Similarity	NPC191132
0.8415	Intermediate Similarity	NPC29647
0.8412	Intermediate Similarity	NPC231371
0.8402	Intermediate Similarity	NPC83198
0.8402	Intermediate Similarity	NPC204908
0.8393	Intermediate Similarity	NPC124657
0.8373	Intermediate Similarity	NPC235143
0.8373	Intermediate Similarity	NPC205255
0.8373	Intermediate Similarity	NPC119649
0.8373	Intermediate Similarity	NPC230956
0.8373	Intermediate Similarity	NPC205167
0.8373	Intermediate Similarity	NPC271388
0.8373	Intermediate Similarity	NPC249274
0.8372	Intermediate Similarity	NPC241704
0.8352	Intermediate Similarity	NPC214116
0.8344	Intermediate Similarity	NPC26601
0.8343	Intermediate Similarity	NPC33902
0.8343	Intermediate Similarity	NPC276674
0.8333	Intermediate Similarity	NPC134858
0.8333	Intermediate Similarity	NPC232514
0.8333	Intermediate Similarity	NPC276944
0.8333	Intermediate Similarity	NPC169743
0.8333	Intermediate Similarity	NPC238530
0.8324	Intermediate Similarity	NPC148693
0.8324	Intermediate Similarity	NPC118633

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 NPC26240 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	190
0.1-0.2	750
0.2-0.3	1148
0.3-0.4	2032
0.4-0.5	2622
0.5-0.6	1602
0.6-0.7	634
0.7-0.8	151
0.8-0.85	21
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8544	High Similarity	NPD2421	Approved
0.8544	High Similarity	NPD2420	Approved
0.8481	Intermediate Similarity	NPD3845	Phase 1
0.8481	Intermediate Similarity	NPD2422	Clinical (unspecified phase)
0.8294	Intermediate Similarity	NPD27	Approved
0.8294	Intermediate Similarity	NPD2489	Approved
0.8284	Intermediate Similarity	NPD3051	Approved
0.8261	Intermediate Similarity	NPD4584	Approved
0.8242	Intermediate Similarity	NPD7298	Approved
0.8235	Intermediate Similarity	NPD2970	Approved
0.8235	Intermediate Similarity	NPD2969	Approved
0.8228	Intermediate Similarity	NPD4664	Clinical (unspecified phase)
0.8182	Intermediate Similarity	NPD8053	Approved
0.8182	Intermediate Similarity	NPD8054	Approved
0.8171	Intermediate Similarity	NPD8453	Clinical (unspecified phase)
0.8146	Intermediate Similarity	NPD7906	Approved
0.8095	Intermediate Similarity	NPD4581	Clinical (unspecified phase)
0.8049	Intermediate Similarity	NPD6031	Approved
0.8049	Intermediate Similarity	NPD6030	Approved
0.8023	Intermediate Similarity	NPD7312	Approved
0.8023	Intermediate Similarity	NPD4578	Approved
0.8023	Intermediate Similarity	NPD7313	Approved
0.8023	Intermediate Similarity	NPD4577	Approved
0.8023	Intermediate Similarity	NPD7311	Approved
0.8023	Intermediate Similarity	NPD7310	Approved
0.7989	Intermediate Similarity	NPD4663	Approved
0.7987	Intermediate Similarity	NPD1632	Clinical (unspecified phase)
0.7978	Intermediate Similarity	NPD7309	Approved
0.7977	Intermediate Similarity	NPD2898	Approved
0.7965	Intermediate Similarity	NPD4010	Discontinued
0.787	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.7853	Intermediate Similarity	NPD5241	Discontinued
0.7849	Intermediate Similarity	NPD7201	Clinical (unspecified phase)
0.784	Intermediate Similarity	NPD3060	Approved
0.7784	Intermediate Similarity	NPD8252	Approved
0.7784	Intermediate Similarity	NPD8099	Discontinued
0.7784	Intermediate Similarity	NPD8251	Approved
0.7771	Intermediate Similarity	NPD4481	Phase 3
0.7765	Intermediate Similarity	NPD2977	Approved
0.7765	Intermediate Similarity	NPD2978	Approved
0.776	Intermediate Similarity	NPD2490	Approved
0.776	Intermediate Similarity	NPD2488	Approved
0.774	Intermediate Similarity	NPD8156	Discontinued
0.7733	Intermediate Similarity	NPD7832	Clinical (unspecified phase)
0.7733	Intermediate Similarity	NPD7831	Phase 2
0.7733	Intermediate Similarity	NPD7833	Phase 2
0.7722	Intermediate Similarity	NPD3534	Clinical (unspecified phase)
0.7674	Intermediate Similarity	NPD6788	Approved
0.7654	Intermediate Similarity	NPD6297	Approved
0.7647	Intermediate Similarity	NPD4773	Phase 2
0.7647	Intermediate Similarity	NPD4772	Phase 2
0.7644	Intermediate Similarity	NPD4666	Phase 3
0.764	Intermediate Similarity	NPD42	Phase 2
0.764	Intermediate Similarity	NPD6042	Phase 2
0.7633	Intermediate Similarity	NPD4017	Approved
0.7607	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7605	Intermediate Similarity	NPD1424	Approved
0.7605	Intermediate Similarity	NPD1754	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD5709	Phase 3
0.7579	Intermediate Similarity	NPD3450	Approved
0.7579	Intermediate Similarity	NPD2493	Approved
0.7579	Intermediate Similarity	NPD2494	Approved
0.7579	Intermediate Similarity	NPD3452	Approved
0.756	Intermediate Similarity	NPD3647	Clinical (unspecified phase)
0.7557	Intermediate Similarity	NPD6071	Discontinued
0.753	Intermediate Similarity	NPD5160	Discontinued
0.7515	Intermediate Similarity	NPD3641	Approved
0.7515	Intermediate Similarity	NPD3639	Approved
0.7515	Intermediate Similarity	NPD5976	Discontinued
0.7515	Intermediate Similarity	NPD4727	Phase 1
0.7515	Intermediate Similarity	NPD3640	Phase 3
0.7514	Intermediate Similarity	NPD2563	Approved
0.7514	Intermediate Similarity	NPD2560	Approved
0.75	Intermediate Similarity	NPD4160	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6107	Approved
0.7486	Intermediate Similarity	NPD6853	Approved
0.7486	Intermediate Similarity	NPD6851	Approved
0.7462	Intermediate Similarity	NPD7827	Phase 1
0.7461	Intermediate Similarity	NPD4582	Approved
0.7461	Intermediate Similarity	NPD4040	Phase 1
0.7461	Intermediate Similarity	NPD4583	Approved
0.7453	Intermediate Similarity	NPD3109	Approved
0.7453	Intermediate Similarity	NPD3110	Approved
0.7452	Intermediate Similarity	NPD3053	Approved
0.7452	Intermediate Similarity	NPD3055	Approved
0.7446	Intermediate Similarity	NPD5087	Clinical (unspecified phase)
0.744	Intermediate Similarity	NPD7598	Phase 2
0.7432	Intermediate Similarity	NPD2968	Approved
0.7432	Intermediate Similarity	NPD2971	Approved
0.7429	Intermediate Similarity	NPD4055	Discovery
0.741	Intermediate Similarity	NPD4162	Approved
0.7409	Intermediate Similarity	NPD4002	Approved
0.7409	Intermediate Similarity	NPD4004	Approved
0.7407	Intermediate Similarity	NPD7667	Clinical (unspecified phase)
0.7403	Intermediate Similarity	NPD7479	Phase 2
0.7378	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7378	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD2975	Approved
0.7368	Intermediate Similarity	NPD2974	Approved
0.7368	Intermediate Similarity	NPD2973	Approved
0.7362	Intermediate Similarity	NPD823	Approved
0.7362	Intermediate Similarity	NPD817	Approved
0.736	Intermediate Similarity	NPD4166	Phase 2
0.7356	Intermediate Similarity	NPD4585	Approved
0.7353	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.7349	Intermediate Similarity	NPD4257	Approved
0.7349	Intermediate Similarity	NPD4256	Phase 2
0.7348	Intermediate Similarity	NPD4873	Discontinued
0.7329	Intermediate Similarity	NPD2028	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD2677	Approved
0.7284	Intermediate Similarity	NPD2674	Phase 3
0.7267	Intermediate Similarity	NPD5155	Approved
0.7267	Intermediate Similarity	NPD5156	Approved
0.7267	Intermediate Similarity	NPD2669	Clinical (unspecified phase)
0.7264	Intermediate Similarity	NPD7047	Phase 3
0.7262	Intermediate Similarity	NPD3977	Clinical (unspecified phase)
0.7254	Intermediate Similarity	NPD4580	Approved
0.7254	Intermediate Similarity	NPD6612	Phase 2
0.7251	Intermediate Similarity	NPD6090	Discontinued
0.7239	Intermediate Similarity	NPD3061	Approved
0.7239	Intermediate Similarity	NPD3062	Approved
0.7239	Intermediate Similarity	NPD3059	Approved
0.7238	Intermediate Similarity	NPD5602	Clinical (unspecified phase)
0.7238	Intermediate Similarity	NPD7922	Phase 1
0.7225	Intermediate Similarity	NPD7261	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD4005	Discontinued
0.7222	Intermediate Similarity	NPD4083	Discontinued
0.7222	Intermediate Similarity	NPD5718	Phase 2
0.722	Intermediate Similarity	NPD6997	Phase 2
0.7219	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7207	Intermediate Similarity	NPD7802	Discontinued
0.7205	Intermediate Similarity	NPD3594	Approved
0.7205	Intermediate Similarity	NPD2605	Approved
0.7205	Intermediate Similarity	NPD3595	Approved
0.7205	Intermediate Similarity	NPD2606	Approved
0.7202	Intermediate Similarity	NPD5177	Phase 3
0.7193	Intermediate Similarity	NPD3645	Discontinued
0.7186	Intermediate Similarity	NPD4725	Approved
0.7186	Intermediate Similarity	NPD4726	Approved
0.7186	Intermediate Similarity	NPD4721	Approved
0.7178	Intermediate Similarity	NPD1130	Approved
0.7178	Intermediate Similarity	NPD1132	Approved
0.7178	Intermediate Similarity	NPD1136	Approved
0.717	Intermediate Similarity	NPD5311	Approved
0.717	Intermediate Similarity	NPD5310	Approved
0.7169	Intermediate Similarity	NPD2156	Approved
0.7169	Intermediate Similarity	NPD1753	Discontinued
0.7169	Intermediate Similarity	NPD2154	Approved
0.7169	Intermediate Similarity	NPD2155	Approved
0.7152	Intermediate Similarity	NPD5314	Approved
0.7143	Intermediate Similarity	NPD3636	Approved
0.7143	Intermediate Similarity	NPD7045	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD3637	Approved
0.7143	Intermediate Similarity	NPD6072	Discontinued
0.7143	Intermediate Similarity	NPD3635	Approved
0.7126	Intermediate Similarity	NPD6523	Clinical (unspecified phase)
0.7118	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD601	Approved
0.7117	Intermediate Similarity	NPD598	Approved
0.7117	Intermediate Similarity	NPD3145	Approved
0.7117	Intermediate Similarity	NPD597	Approved
0.7117	Intermediate Similarity	NPD3144	Approved
0.7113	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7092	Intermediate Similarity	NPD2491	Approved
0.7092	Intermediate Similarity	NPD3057	Approved
0.7092	Intermediate Similarity	NPD3448	Approved
0.7076	Intermediate Similarity	NPD3122	Phase 3
0.7075	Intermediate Similarity	NPD6723	Discontinued
0.7073	Intermediate Similarity	NPD4475	Approved
0.7073	Intermediate Similarity	NPD554	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD4474	Approved
0.7069	Intermediate Similarity	NPD3687	Approved
0.7069	Intermediate Similarity	NPD3686	Approved
0.7065	Intermediate Similarity	NPD5096	Phase 3
0.7065	Intermediate Similarity	NPD5095	Phase 3
0.7065	Intermediate Similarity	NPD3933	Discontinued
0.7059	Intermediate Similarity	NPD5917	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD3052	Approved
0.7048	Intermediate Similarity	NPD3054	Approved
0.7043	Intermediate Similarity	NPD7038	Approved
0.7043	Intermediate Similarity	NPD7039	Approved
0.7035	Intermediate Similarity	NPD1774	Approved
0.7035	Intermediate Similarity	NPD3124	Discontinued
0.7026	Intermediate Similarity	NPD8095	Phase 1
0.7025	Intermediate Similarity	NPD2688	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD6618	Phase 2
0.7021	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD5708	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD5720	Discontinued
0.7006	Intermediate Similarity	NPD6896	Approved
0.7006	Intermediate Similarity	NPD6895	Approved
0.7005	Intermediate Similarity	NPD2972	Approved
0.7005	Intermediate Similarity	NPD3533	Approved
0.7	Intermediate Similarity	NPD4236	Phase 3
0.7	Intermediate Similarity	NPD4237	Approved
0.6994	Remote Similarity	NPD4123	Phase 3
0.6994	Remote Similarity	NPD3536	Discontinued
0.6994	Remote Similarity	NPD5752	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD7124	Phase 2
0.6977	Remote Similarity	NPD6667	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