NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	152.12
Volume:	170.557
LogP:	2.775
LogD:	2.367
LogS:	-2.835
# Rotatable Bonds:	1
TPSA:	12.53
# H-Bond Aceptor:	1
# H-Bond Donor:	0
# Rings:	2
# Heavy Atoms:	1

MedChem Properties

QED Drug-Likeness Score:	0.415
Synthetic Accessibility Score:	3.909
Fsp3:	0.8
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.431
MDCK Permeability:	2.3474425688618794e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.01
30% Bioavailability (F30%):	0.007

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.976
Plasma Protein Binding (PPB):	52.90496063232422%
Volume Distribution (VD):	1.679
Pgp-substrate:	41.384098052978516%

ADMET: Metabolism

CYP1A2-inhibitor:	0.106
CYP1A2-substrate:	0.491
CYP2C19-inhibitor:	0.054
CYP2C19-substrate:	0.913
CYP2C9-inhibitor:	0.041
CYP2C9-substrate:	0.421
CYP2D6-inhibitor:	0.008
CYP2D6-substrate:	0.887
CYP3A4-inhibitor:	0.046
CYP3A4-substrate:	0.337

ADMET: Excretion

Clearance (CL):	16.98
Half-life (T1/2):	0.298

ADMET: Toxicity

hERG Blockers:	0.035
Human Hepatotoxicity (H-HT):	0.318
Drug-inuced Liver Injury (DILI):	0.044
AMES Toxicity:	0.032
Rat Oral Acute Toxicity:	0.026
Maximum Recommended Daily Dose:	0.286
Skin Sensitization:	0.243
Carcinogencity:	0.675
Eye Corrosion:	0.649
Eye Irritation:	0.972
Respiratory Toxicity:	0.932

Download Data

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

Natural Product: NPC210316

Natural Product ID:	NPC210316
*Common Name:**	Limonene Oxide
IUPAC Name:	6-methyl-3-prop-1-en-2-yl-7-oxabicyclo[4.1.0]heptane
Synonyms:
Standard InCHIKey:	CCEFMUBVSUDRLG-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C10H16O/c1-7(2)8-4-5-10(3)9(6-8)11-10/h8-9H,1,4-6H2,2-3H3
SMILES:	CC(=C)C1CCC2(C(C1)O2)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2268547
PubChem CID:	91496
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001729] Oxepanes

*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
NPO319	Citrus limon	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/S0031-9422(99)00119-3]
NPO19787	Citrus sinensis	Species	Rutaceae	Eukaryota	n.a.	fruit	n.a.	PMID[10606547]
NPO319	Citrus limon	Species	Rutaceae	Eukaryota	n.a.	fruit	n.a.	PMID[10606547]
NPO7317	Citrus aurantium	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10606602]
NPO11438	Angelica gigas	Species	Apiaceae	Eukaryota	n.a.	root	n.a.	PMID[11374978]
NPO16501	Capsicum annuum	Species	Solanaceae	Eukaryota	n.a.	fruit	n.a.	PMID[12932131]
NPO11438	Angelica gigas	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15679317]
NPO11169	Piper cubeba	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15679319]
NPO15462	Angelica sinensis	Species	Apiaceae	Eukaryota	roots	purchased from Kiu Shun Trading Ltd., Vancouver, Canada	2000	PMID[16643021]
NPO5270	Citrus natsudaidai	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17689080]
NPO11438	Angelica gigas	Species	Apiaceae	Eukaryota	n.a.	root	n.a.	PMID[17997069]
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota	rhizomes	n.a.	n.a.	PMID[18177011]
NPO29110	Litsea cubeba	Species	Lauraceae	Eukaryota	n.a.	aerial part	n.a.	PMID[18991207]
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19271742]
NPO16501	Capsicum annuum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20460582]
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20590154]
NPO29110	Litsea cubeba	Species	Lauraceae	Eukaryota	essential oil	Tibet	n.a.	PMID[20944522]
NPO21771	Citrus trifoliata	Species	Rutaceae	Eukaryota	n.a.	fruit	n.a.	PMID[23872723]
NPO16501	Capsicum annuum	Species	Solanaceae	Eukaryota	n.a.	fruit	n.a.	PMID[25172746]
NPO15462	Angelica sinensis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25538068]
NPO15462	Angelica sinensis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27400088]
NPO29110	Litsea cubeba	Species	Lauraceae	Eukaryota	Twigs	n.a.	n.a.	PMID[28541690]
NPO21771	Citrus trifoliata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32996318]
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota	n.a.	rhizome	n.a.	PMID[8064299]
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8064299]
NPO16501	Capsicum annuum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8910532]
NPO11169	Piper cubeba	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[Article]
NPO19787	Citrus sinensis	Species	Rutaceae	Eukaryota	Bark	n.a.	n.a.	Database[FooDB]
NPO319	Citrus limon	Species	Rutaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO319	Citrus limon	Species	Rutaceae	Eukaryota	Essential Oil	n.a.	n.a.	Database[FooDB]
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO319	Citrus limon	Species	Rutaceae	Eukaryota	Flower	n.a.	n.a.	Database[FooDB]
NPO16501	Capsicum annuum	Species	Solanaceae	Eukaryota	Resin, Exudate, Sap	n.a.	n.a.	Database[FooDB]
NPO7698	Elettaria cardamomum	Species	Zingiberaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota	Resin, Exudate, Sap	n.a.	n.a.	Database[FooDB]
NPO16501	Capsicum annuum	Species	Solanaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota	Rhizome	n.a.	n.a.	Database[FooDB]
NPO319	Citrus limon	Species	Rutaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO16501	Capsicum annuum	Species	Solanaceae	Eukaryota	Root	n.a.	n.a.	Database[FooDB]
NPO19787	Citrus sinensis	Species	Rutaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota	Root	n.a.	n.a.	Database[FooDB]
NPO19787	Citrus sinensis	Species	Rutaceae	Eukaryota	Fruit Juice	n.a.	n.a.	Database[FooDB]
NPO19787	Citrus sinensis	Species	Rutaceae	Eukaryota	Root Bark	n.a.	n.a.	Database[FooDB]
NPO16501	Capsicum annuum	Species	Solanaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO7698	Elettaria cardamomum	Species	Zingiberaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO319	Citrus limon	Species	Rutaceae	Eukaryota	Leaf Essent. Oil	n.a.	n.a.	Database[FooDB]
NPO16501	Capsicum annuum	Species	Solanaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO16501	Capsicum annuum	Species	Solanaceae	Eukaryota	Pericarp	n.a.	n.a.	Database[FooDB]
NPO16501	Capsicum annuum	Species	Solanaceae	Eukaryota	Tissue Culture	n.a.	n.a.	Database[FooDB]
NPO7698	Elettaria cardamomum	Species	Zingiberaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO19787	Citrus sinensis	Species	Rutaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO16501	Capsicum annuum	Species	Solanaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO319	Citrus limon	Species	Rutaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO319	Citrus limon	Species	Rutaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO19787	Citrus sinensis	Species	Rutaceae	Eukaryota	Pericarp	n.a.	n.a.	Database[FooDB]
NPO19787	Citrus sinensis	Species	Rutaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO7698	Elettaria cardamomum	Species	Zingiberaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO7698	Elettaria cardamomum	Species	Zingiberaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO16501	Capsicum annuum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11169	Piper cubeba	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19787	Citrus sinensis	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15730.2	Citrus medica var. sarcodactylis	Varieties	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29110	Litsea cubeba	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11438	Angelica gigas	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7317	Citrus aurantium	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15462	Angelica sinensis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2921	Angelica acutiloba	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO319	Citrus limon	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO319	Citrus limon	Species	Rutaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO319	Citrus limon	Species	Rutaceae	Eukaryota	Fruits	n.a.		Database[Phenol-Explorer]
NPO7698	Elettaria cardamomum	Species	Zingiberaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO16501	Capsicum annuum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12916	Radix et rhizoma rhodiolae	Species	Lymnaeidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7317	Citrus aurantium	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19787	Citrus sinensis	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11169	Piper cubeba	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2921	Angelica acutiloba	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15462	Angelica sinensis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11438	Angelica gigas	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO319	Citrus limon	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21771	Citrus trifoliata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22178.1	Centranthus longiflorus ssp. longiflorus	Subspecies	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15730.2	Citrus medica var. sarcodactylis	Varieties	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29110	Litsea cubeba	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16501	Capsicum annuum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO15462	Angelica sinensis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO15730.2	Citrus medica var. sarcodactylis	Varieties	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO19787	Citrus sinensis	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO2921	Angelica acutiloba	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO319	Citrus limon	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO11438	Angelica gigas	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO7317	Citrus aurantium	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO5270	Citrus natsudaidai	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[Title]
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO16501	Capsicum annuum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO2921	Angelica acutiloba	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO7317	Citrus aurantium	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO5270	Citrus natsudaidai	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO19787	Citrus sinensis	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO15462	Angelica sinensis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO21771	Citrus trifoliata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO11438	Angelica gigas	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO7698	Elettaria cardamomum	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO11169	Piper cubeba	Species	Piperaceae	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]
NPO11438	Angelica gigas	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7698	Elettaria cardamomum	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19787	Citrus sinensis	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21771	Citrus trifoliata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2921	Angelica acutiloba	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5270	Citrus natsudaidai	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15462	Angelica sinensis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16501	Capsicum annuum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7317	Citrus aurantium	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO319	Citrus limon	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29110	Litsea cubeba	Species	Lauraceae	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
LD50	1
Others	33

Activity Type	# Activity
Individual Protein	1
Organism	33

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1275	Organism	Leptinotarsa decemlineata	Leptinotarsa decemlineata	mortality	=	10.0	%	PMID[513217]
NPT1275	Organism	Leptinotarsa decemlineata	Leptinotarsa decemlineata	mortality	=	100.0	%	PMID[513217]
NPT1275	Organism	Leptinotarsa decemlineata	Leptinotarsa decemlineata	mortality	=	40.0	%	PMID[513217]
NPT1275	Organism	Leptinotarsa decemlineata	Leptinotarsa decemlineata	mortality	=	30.0	%	PMID[513217]
NPT1275	Organism	Leptinotarsa decemlineata	Leptinotarsa decemlineata	mortality	=	73.3	%	PMID[513217]
NPT1275	Organism	Leptinotarsa decemlineata	Leptinotarsa decemlineata	mortality	=	56.7	%	PMID[513217]
NPT1275	Organism	Leptinotarsa decemlineata	Leptinotarsa decemlineata	mortality	=	53.3	%	PMID[513217]
NPT1275	Organism	Leptinotarsa decemlineata	Leptinotarsa decemlineata	mortality	=	60.0	%	PMID[513217]
NPT1275	Organism	Leptinotarsa decemlineata	Leptinotarsa decemlineata	mortality	=	20.0	%	PMID[513217]
NPT1275	Organism	Leptinotarsa decemlineata	Leptinotarsa decemlineata	mortality	=	80.0	%	PMID[513217]
NPT1275	Organism	Leptinotarsa decemlineata	Leptinotarsa decemlineata	mortality	=	83.3	%	PMID[513217]
NPT1275	Organism	Leptinotarsa decemlineata	Leptinotarsa decemlineata	mortality	=	16.7	%	PMID[513217]
NPT1275	Organism	Leptinotarsa decemlineata	Leptinotarsa decemlineata	mortality	=	93.3	%	PMID[513217]
NPT1275	Organism	Leptinotarsa decemlineata	Leptinotarsa decemlineata	mortality	=	46.7	%	PMID[513217]
NPT1275	Organism	Leptinotarsa decemlineata	Leptinotarsa decemlineata	mortality	=	43.3	%	PMID[513217]
NPT1275	Organism	Leptinotarsa decemlineata	Leptinotarsa decemlineata	mortality	=	33.3	%	PMID[513217]
NPT1275	Organism	Leptinotarsa decemlineata	Leptinotarsa decemlineata	mortality	=	26.7	%	PMID[513217]
NPT1275	Organism	Leptinotarsa decemlineata	Leptinotarsa decemlineata	mortality	=	13.3	%	PMID[513217]
NPT1275	Organism	Leptinotarsa decemlineata	Leptinotarsa decemlineata	mortality	=	90.0	%	PMID[513217]
NPT1275	Organism	Leptinotarsa decemlineata	Leptinotarsa decemlineata	mortality	=	70.0	%	PMID[513217]
NPT1275	Organism	Leptinotarsa decemlineata	Leptinotarsa decemlineata	mortality	=	96.7	%	PMID[513217]
NPT1275	Organism	Leptinotarsa decemlineata	Leptinotarsa decemlineata	mortality	=	23.3	%	PMID[513217]
NPT734	Organism	Musca domestica	Musca domestica	LD50	=	67.8	ug	PMID[513218]
NPT735	Individual Protein	GABA receptor subunit	Musca domestica	Activity	=	141.0	%	PMID[513218]

☑ 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 NPC210316 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	229
0.1-0.2	3396
0.2-0.3	15246
0.3-0.4	12689
0.4-0.5	8436
0.5-0.6	2470
0.6-0.7	213
0.7-0.8	16
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.8276	Intermediate Similarity	NPC240206
0.807	Intermediate Similarity	NPC84824
0.807	Intermediate Similarity	NPC67508
0.7797	Intermediate Similarity	NPC13789
0.7797	Intermediate Similarity	NPC65786
0.7797	Intermediate Similarity	NPC101285
0.7797	Intermediate Similarity	NPC7491
0.7797	Intermediate Similarity	NPC27853
0.7759	Intermediate Similarity	NPC223604
0.7679	Intermediate Similarity	NPC251335
0.7458	Intermediate Similarity	NPC300189
0.7455	Intermediate Similarity	NPC100445
0.7344	Intermediate Similarity	NPC101128
0.7333	Intermediate Similarity	NPC170780
0.7273	Intermediate Similarity	NPC139207
0.7273	Intermediate Similarity	NPC269077
0.7273	Intermediate Similarity	NPC185874
0.7273	Intermediate Similarity	NPC253303
0.7222	Intermediate Similarity	NPC52755
0.7188	Intermediate Similarity	NPC50435
0.7164	Intermediate Similarity	NPC244790
0.7143	Intermediate Similarity	NPC71152
0.7121	Intermediate Similarity	NPC473929
0.7119	Intermediate Similarity	NPC165755
0.7097	Intermediate Similarity	NPC189290
0.7097	Intermediate Similarity	NPC474769
0.7077	Intermediate Similarity	NPC287744
0.7077	Intermediate Similarity	NPC144650
0.7077	Intermediate Similarity	NPC68656
0.7077	Intermediate Similarity	NPC140233
0.7077	Intermediate Similarity	NPC219940
0.7031	Intermediate Similarity	NPC194208
0.7031	Intermediate Similarity	NPC282694
0.7031	Intermediate Similarity	NPC79576
0.7015	Intermediate Similarity	NPC474477
0.697	Remote Similarity	NPC172613
0.697	Remote Similarity	NPC208198
0.697	Remote Similarity	NPC282619
0.697	Remote Similarity	NPC474768
0.697	Remote Similarity	NPC258595
0.697	Remote Similarity	NPC11555
0.697	Remote Similarity	NPC2728
0.697	Remote Similarity	NPC60837
0.6944	Remote Similarity	NPC470766
0.6923	Remote Similarity	NPC283247
0.6912	Remote Similarity	NPC245795
0.6912	Remote Similarity	NPC276616
0.6912	Remote Similarity	NPC266578
0.6912	Remote Similarity	NPC139785
0.6897	Remote Similarity	NPC142103
0.6875	Remote Similarity	NPC240506
0.6866	Remote Similarity	NPC475897
0.6866	Remote Similarity	NPC469328
0.6857	Remote Similarity	NPC167706
0.6857	Remote Similarity	NPC164022
0.6857	Remote Similarity	NPC242992
0.6857	Remote Similarity	NPC23954
0.6849	Remote Similarity	NPC470750
0.6849	Remote Similarity	NPC470751
0.6818	Remote Similarity	NPC225415
0.6812	Remote Similarity	NPC234511
0.6786	Remote Similarity	NPC87439
0.678	Remote Similarity	NPC291724
0.678	Remote Similarity	NPC274261
0.6774	Remote Similarity	NPC264779
0.6774	Remote Similarity	NPC39068
0.6765	Remote Similarity	NPC33583
0.6765	Remote Similarity	NPC161612
0.6761	Remote Similarity	NPC95165
0.6761	Remote Similarity	NPC220939
0.6761	Remote Similarity	NPC265485
0.6719	Remote Similarity	NPC83838
0.6719	Remote Similarity	NPC143810
0.6716	Remote Similarity	NPC300442
0.6716	Remote Similarity	NPC64123
0.6714	Remote Similarity	NPC45296
0.6714	Remote Similarity	NPC283316
0.6714	Remote Similarity	NPC92801
0.6712	Remote Similarity	NPC92489
0.6667	Remote Similarity	NPC49168
0.6667	Remote Similarity	NPC283789
0.6667	Remote Similarity	NPC254509
0.6667	Remote Similarity	NPC196358
0.6667	Remote Similarity	NPC145552
0.6667	Remote Similarity	NPC96484
0.6667	Remote Similarity	NPC47808
0.6667	Remote Similarity	NPC84030
0.6667	Remote Similarity	NPC223468
0.6667	Remote Similarity	NPC306951
0.6667	Remote Similarity	NPC176309
0.6667	Remote Similarity	NPC287550
0.6667	Remote Similarity	NPC147343
0.6667	Remote Similarity	NPC86238
0.6667	Remote Similarity	NPC198540
0.6667	Remote Similarity	NPC5046
0.6622	Remote Similarity	NPC477427
0.6622	Remote Similarity	NPC477426
0.6622	Remote Similarity	NPC477425
0.6622	Remote Similarity	NPC474826
0.6622	Remote Similarity	NPC84868
0.662	Remote Similarity	NPC111234
0.662	Remote Similarity	NPC301226
0.6618	Remote Similarity	NPC42630
0.6618	Remote Similarity	NPC327815
0.6615	Remote Similarity	NPC127824
0.6579	Remote Similarity	NPC206735
0.6575	Remote Similarity	NPC3403
0.6575	Remote Similarity	NPC70982
0.6575	Remote Similarity	NPC200243
0.6575	Remote Similarity	NPC230704
0.6571	Remote Similarity	NPC210323
0.6571	Remote Similarity	NPC239373
0.6571	Remote Similarity	NPC9942
0.6571	Remote Similarity	NPC329989
0.6571	Remote Similarity	NPC329656
0.6567	Remote Similarity	NPC323424
0.6567	Remote Similarity	NPC96793
0.6533	Remote Similarity	NPC472342
0.6528	Remote Similarity	NPC182717
0.6528	Remote Similarity	NPC195489
0.6528	Remote Similarity	NPC211009
0.6522	Remote Similarity	NPC259299
0.6508	Remote Similarity	NPC24443
0.65	Remote Similarity	NPC255143
0.65	Remote Similarity	NPC125399
0.6494	Remote Similarity	NPC116202
0.6486	Remote Similarity	NPC91573
0.6486	Remote Similarity	NPC265588
0.6486	Remote Similarity	NPC476607
0.6486	Remote Similarity	NPC63958
0.6471	Remote Similarity	NPC471200
0.6462	Remote Similarity	NPC185116
0.6456	Remote Similarity	NPC474047
0.6447	Remote Similarity	NPC305835
0.6441	Remote Similarity	NPC224987
0.6438	Remote Similarity	NPC100334
0.6438	Remote Similarity	NPC62657
0.6438	Remote Similarity	NPC476366
0.6438	Remote Similarity	NPC472503
0.6438	Remote Similarity	NPC25511
0.6438	Remote Similarity	NPC201048
0.6438	Remote Similarity	NPC308440
0.6438	Remote Similarity	NPC192638
0.6429	Remote Similarity	NPC302939
0.6429	Remote Similarity	NPC2648
0.6429	Remote Similarity	NPC287331
0.6429	Remote Similarity	NPC305698
0.6429	Remote Similarity	NPC94192
0.6429	Remote Similarity	NPC208999
0.642	Remote Similarity	NPC475087
0.641	Remote Similarity	NPC155521
0.64	Remote Similarity	NPC283619
0.64	Remote Similarity	NPC470758
0.64	Remote Similarity	NPC470711
0.64	Remote Similarity	NPC169994
0.64	Remote Similarity	NPC257191
0.64	Remote Similarity	NPC331618
0.6393	Remote Similarity	NPC181255
0.6393	Remote Similarity	NPC157781
0.6393	Remote Similarity	NPC179169
0.6393	Remote Similarity	NPC35519
0.6393	Remote Similarity	NPC306195
0.6389	Remote Similarity	NPC110799
0.6389	Remote Similarity	NPC471272
0.6389	Remote Similarity	NPC477792
0.6377	Remote Similarity	NPC202017
0.6377	Remote Similarity	NPC326310
0.6364	Remote Similarity	NPC66020
0.6364	Remote Similarity	NPC304194
0.6351	Remote Similarity	NPC104387
0.6351	Remote Similarity	NPC240235
0.6351	Remote Similarity	NPC144075
0.6351	Remote Similarity	NPC212879
0.6351	Remote Similarity	NPC178383
0.6351	Remote Similarity	NPC121744
0.6351	Remote Similarity	NPC118508
0.6351	Remote Similarity	NPC475861
0.6351	Remote Similarity	NPC322353
0.6351	Remote Similarity	NPC185536
0.6351	Remote Similarity	NPC231256
0.6341	Remote Similarity	NPC93411
0.6338	Remote Similarity	NPC74722
0.6338	Remote Similarity	NPC477448
0.6338	Remote Similarity	NPC304690
0.6338	Remote Similarity	NPC476431
0.6338	Remote Similarity	NPC269841
0.6338	Remote Similarity	NPC477449
0.6329	Remote Similarity	NPC127917
0.6329	Remote Similarity	NPC194637
0.6329	Remote Similarity	NPC139206
0.6329	Remote Similarity	NPC477978
0.6316	Remote Similarity	NPC302041
0.6316	Remote Similarity	NPC31828
0.6316	Remote Similarity	NPC68119
0.6316	Remote Similarity	NPC476314
0.6316	Remote Similarity	NPC312328
0.6316	Remote Similarity	NPC85346
0.6316	Remote Similarity	NPC42853
0.6316	Remote Similarity	NPC285761
0.6316	Remote Similarity	NPC301707

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 NPC210316 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	221
0.1-0.2	3623
0.2-0.3	3753
0.3-0.4	1183
0.4-0.5	304
0.5-0.6	61
0.6-0.7	3
0.7-0.8	1
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7963	Intermediate Similarity	NPD9410	Clinical (unspecified phase)
0.7705	Intermediate Similarity	NPD1145	Discontinued
0.6667	Remote Similarity	NPD385	Approved
0.6667	Remote Similarity	NPD384	Approved
0.6429	Remote Similarity	NPD367	Approved
0.6269	Remote Similarity	NPD368	Approved
0.6234	Remote Similarity	NPD7645	Phase 2
0.6232	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD7525	Registered
0.6094	Remote Similarity	NPD342	Phase 1
0.6087	Remote Similarity	NPD371	Approved
0.6	Remote Similarity	NPD3168	Discontinued
0.5932	Remote Similarity	NPD388	Approved
0.5932	Remote Similarity	NPD386	Approved
0.5921	Remote Similarity	NPD6942	Approved
0.5921	Remote Similarity	NPD7339	Approved
0.5844	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.5789	Remote Similarity	NPD6926	Approved
0.5789	Remote Similarity	NPD6924	Approved
0.5641	Remote Similarity	NPD6933	Approved
0.5614	Remote Similarity	NPD1460	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