NPASS Compound

Structure

CID296643 OpenBabel06191716102D 38 40 0 0 1 0 0 0 0 0999 V2000 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 -6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -4.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 -5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.4641 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 -5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -2.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.6603 -4.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.6603 -6.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -6.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -6.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 3 1 0 0 0 0 2 34 1 0 0 0 0 3 13 2 0 0 0 0 4 5 2 0 0 0 0 4 12 1 0 0 0 0 5 16 1 0 0 0 0 6 7 1 0 0 0 0 6 12 1 0 0 0 0 7 35 1 0 0 0 0 8 12 2 0 0 0 0 8 17 1 0 0 0 0 9 19 1 0 0 0 0 10 26 1 0 0 0 0 11 15 2 0 0 0 0 11 36 1 0 0 0 0 13 14 1 0 0 0 0 13 24 1 0 0 0 0 14 9 1 1 0 0 0 14 15 1 0 0 0 0 15 23 1 0 0 0 0 16 17 2 0 0 0 0 16 27 1 0 0 0 0 17 28 1 0 0 0 0 18 10 1 6 0 0 0 18 20 1 0 0 0 0 18 37 1 0 0 0 0 19 29 2 0 0 0 0 19 35 1 0 0 0 0 20 21 1 0 0 0 0 20 30 1 1 0 0 0 21 22 1 0 0 0 0 21 31 1 6 0 0 0 22 25 1 0 0 0 0 22 32 1 1 0 0 0 23 33 2 0 0 0 0 23 34 1 0 0 0 0 24 36 1 0 0 0 0 24 38 1 6 0 0 0 25 37 1 0 0 0 0 25 38 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	540.18
Volume:	511.104
LogP:	0.498
LogD:	0.171
LogS:	-1.443
# Rotatable Bonds:	11
TPSA:	201.67
# H-Bond Aceptor:	13
# H-Bond Donor:	6
# Rings:	3
# Heavy Atoms:	13

MedChem Properties

QED Drug-Likeness Score:	0.131
Synthetic Accessibility Score:	4.677
Fsp3:	0.52
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.677
MDCK Permeability:	9.636813047109172e-05
Pgp-inhibitor:	0.002
Pgp-substrate:	0.99
Human Intestinal Absorption (HIA):	0.908
20% Bioavailability (F20%):	0.012
30% Bioavailability (F30%):	0.997

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.311
Plasma Protein Binding (PPB):	70.22289276123047%
Volume Distribution (VD):	0.528
Pgp-substrate:	26.131343841552734%

ADMET: Metabolism

CYP1A2-inhibitor:	0.061
CYP1A2-substrate:	0.088
CYP2C19-inhibitor:	0.063
CYP2C19-substrate:	0.063
CYP2C9-inhibitor:	0.061
CYP2C9-substrate:	0.132
CYP2D6-inhibitor:	0.192
CYP2D6-substrate:	0.124
CYP3A4-inhibitor:	0.198
CYP3A4-substrate:	0.167

ADMET: Excretion

Clearance (CL):	3.091
Half-life (T1/2):	0.929

ADMET: Toxicity

hERG Blockers:	0.025
Human Hepatotoxicity (H-HT):	0.157
Drug-inuced Liver Injury (DILI):	0.931
AMES Toxicity:	0.88
Rat Oral Acute Toxicity:	0.39
Maximum Recommended Daily Dose:	0.944
Skin Sensitization:	0.296
Carcinogencity:	0.903
Eye Corrosion:	0.003
Eye Irritation:	0.019
Respiratory Toxicity:	0.897

Download Data

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

Natural Product: NPC296643

Natural Product ID:	NPC296643
*Common Name:**	Oleuropein
IUPAC Name:	methyl (4S,5E,6S)-4-[2-[2-(3,4-dihydroxyphenyl)ethoxy]-2-oxoethyl]-5-ethylidene-6-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4H-pyran-3-carboxylate
Synonyms:	Oleuropein
Standard InCHIKey:	RFWGABANNQMHMZ-ZCHJGGQASA-N
Standard InCHI:	InChI=1S/C25H32O13/c1-3-13-14(9-19(29)35-7-6-12-4-5-16(27)17(28)8-12)15(23(33)34-2)11-36-24(13)38-25-22(32)21(31)20(30)18(10-26)37-25/h3-5,8,11,14,18,20-22,24-28,30-32H,6-7,9-10H2,1-2H3/b13-3+/t14-,18+,20+,21-,22+,24-,25-/m0/s1
SMILES:	C/C=C/1[C@H](CC(=O)OCCc2ccc(c(c2)O)O)C(=CO[C@H]1O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O)C(=O)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1911053
PubChem CID:	5281544
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0002049] Terpene glycosides

*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
NPO28608	Olea europaea	Species	Oleaceae	Eukaryota	n.a.	fruit	n.a.	PMID[12802735]
NPO28608	Olea europaea	Species	Oleaceae	Eukaryota	n.a.	fruit	n.a.	PMID[18384095]
NPO16259	Syringa reticulata	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21955940]
NPO28608	Olea europaea	Species	Oleaceae	Eukaryota	n.a.	fruit	n.a.	PMID[22014120]
NPO28608	Olea europaea	Species	Oleaceae	Eukaryota	n.a.	leaf	n.a.	PMID[22014120]
NPO28608	Olea europaea	Species	Oleaceae	Eukaryota	n.a.	leaf	n.a.	PMID[22014168]
NPO28608	Olea europaea	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23540838]
NPO28608	Olea europaea	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24295708]
NPO28608	Olea europaea	Species	Oleaceae	Eukaryota	n.a.	leaf	n.a.	PMID[25102361]
NPO28608	Olea europaea	Species	Oleaceae	Eukaryota	n.a.	fruit	n.a.	PMID[25306330]
NPO41060	Syringa dilatata	Species	Oleaceae	Eukaryota	Flowers	n.a.	n.a.	PMID[32936639]
NPO19935	Evodia rutaecarpa	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7463094]
NPO19935	Evodia rutaecarpa	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8201313]
NPO19935	Evodia rutaecarpa	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8699182]
NPO28608	Olea europaea	Species	Oleaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO28608	Olea europaea	Species	Oleaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO28608	Olea europaea	Species	Oleaceae	Eukaryota	Oil	n.a.	n.a.	Database[FooDB]
NPO3564	Fraxinus stylosa	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28608	Olea europaea	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15212	Fraxinus chinensis	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9661	Fraxinus szaboana	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28608	Olea europaea	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15212	Fraxinus chinensis	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19935	Evodia rutaecarpa	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9661	Fraxinus szaboana	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15212.1	Fraxinus chinensis subsp. rhynchophylla	Subspecies	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3564	Fraxinus stylosa	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15212	Fraxinus chinensis	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO3564	Fraxinus stylosa	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO28608	Olea europaea	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO9661	Fraxinus szaboana	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO4877	Euodia officinalis	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO8314	Euodia ruticarpa	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO16845	Euodia bodinieri	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO19935	Evodia rutaecarpa	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO15212.1	Fraxinus chinensis subsp. rhynchophylla	Subspecies	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO3564	Fraxinus stylosa	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO15212	Fraxinus chinensis	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO9661	Fraxinus szaboana	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO19935	Evodia rutaecarpa	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16259	Syringa reticulata	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15212	Fraxinus chinensis	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28608	Olea europaea	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15212.1	Fraxinus chinensis subsp. rhynchophylla	Subspecies	Oleaceae	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
NPO28608	NPC296643	Oil	n.a.	0.000055	n.a.	n.a.	mg/100g	Database [PHENOL EXPLORER]
NPO28608	NPC296643	Oil	n.a.	0.167111105	n.a.	n.a.	mg/100g	Database [PHENOL EXPLORER]
NPO28608	NPC296643	Raw	n.a.	55.57500006	n.a.	n.a.	mg/100g	Database [PHENOL EXPLORER]
NPO28608	NPC296643	Raw	n.a.	72.01629982	n.a.	n.a.	mg/100g	Database [PHENOL EXPLORER]

☑ 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
EC50	2
IC50	12
Others	46

Activity Type	# Activity
Cell Line	22
CELL-LINE	12
Individual Protein	1
NON-MOLECULAR	3
Organism	19
Others	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT570	Individual Protein	Arachidonate 5-lipoxygenase	Homo sapiens	Inhibition	=	35.0	%	PMID[468013]
NPT393	Cell Line	HCT-116	Homo sapiens	IC50	=	181860.0	nM	PMID[468014]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	265280.0	nM	PMID[468014]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	161570.0	nM	PMID[468014]
NPT134	Cell Line	SK-BR-3	Homo sapiens	IC50	=	160440.0	nM	PMID[468014]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	=	54260.0	nM	PMID[468014]
NPT111	Cell Line	K562	Homo sapiens	IC50	=	64730.0	nM	PMID[468014]
NPT927	Cell Line	PBMC	Homo sapiens	Activity	=	0.8	%	PMID[468014]
NPT927	Cell Line	PBMC	Homo sapiens	Activity	=	1.5	%	PMID[468014]
NPT927	Cell Line	PBMC	Homo sapiens	Activity	=	2.5	%	PMID[468014]
NPT927	Cell Line	PBMC	Homo sapiens	Activity	=	1.2	%	PMID[468014]
NPT927	Cell Line	PBMC	Homo sapiens	Activity	=	1.9	%	PMID[468014]
NPT927	Cell Line	PBMC	Homo sapiens	Activity	=	3.9	%	PMID[468014]
NPT927	Cell Line	PBMC	Homo sapiens	Activity	=	1.6	%	PMID[468014]
NPT927	Cell Line	PBMC	Homo sapiens	Activity	=	3.0	%	PMID[468014]
NPT927	Cell Line	PBMC	Homo sapiens	Activity	=	4.3	%	PMID[468014]
NPT927	Cell Line	PBMC	Homo sapiens	Activity	=	3.1	%	PMID[468014]
NPT927	Cell Line	PBMC	Homo sapiens	Activity	=	6.3	%	PMID[468014]
NPT927	Cell Line	PBMC	Homo sapiens	Activity	=	10.3	%	PMID[468014]
NPT927	Cell Line	PBMC	Homo sapiens	Activity	=	6.5	%	PMID[468014]
NPT927	Cell Line	PBMC	Homo sapiens	Activity	=	12.4	%	PMID[468014]
NPT927	Cell Line	PBMC	Homo sapiens	Activity	=	16.4	%	PMID[468014]
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	>	80000.0	nM	PMID[468016]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	EC50	=	2570.0	nM	PMID[468009]
NPT1	Others	Radical scavenging activity		EC50	=	20840.0	nM	PMID[468009]
NPT1503	Organism	Verticillium dahliae	Verticillium dahliae	IC50	=	170.0	ug.mL-1	PMID[468011]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	80.0	%	PMID[468012]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	57.0	%	PMID[468012]
NPT32	Organism	Mus musculus	Mus musculus	FC	=	46.0	n.a.	PMID[468012]
NPT2	Others	Unspecified		Inhibition	=	83.0	%	PMID[468012]
NPT32	Organism	Mus musculus	Mus musculus	Activity	<=	65.0	%	PMID[468012]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	58.0	%	PMID[468012]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	68.0	%	PMID[468012]
NPT32	Organism	Mus musculus	Mus musculus	Inhibition	=	34.0	%	PMID[468012]
NPT32	Organism	Mus musculus	Mus musculus	Inhibition	=	25.0	%	PMID[468012]
NPT32	Organism	Mus musculus	Mus musculus	Inhibition	=	37.0	%	PMID[468012]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	46.0	%	PMID[468012]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	42.0	%	PMID[468012]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	36.0	%	PMID[468012]
NPT2	Others	Unspecified		IC50	=	268820.0	nM	PMID[468014]
NPT24776	CELL-LINE	B16-F1	Mus musculus	IC50	=	283900.0	nM	PMID[468014]
NPT24776	CELL-LINE	B16-F1	Mus musculus	Activity	=	9.3	%	PMID[468014]
NPT24776	CELL-LINE	B16-F1	Mus musculus	Activity	=	6.9	%	PMID[468014]
NPT24776	CELL-LINE	B16-F1	Mus musculus	Activity	=	2.1	%	PMID[468014]
NPT24776	CELL-LINE	B16-F1	Mus musculus	Activity	=	13.6	%	PMID[468014]
NPT24776	CELL-LINE	B16-F1	Mus musculus	Activity	=	9.8	%	PMID[468014]
NPT24776	CELL-LINE	B16-F1	Mus musculus	Activity	=	4.2	%	PMID[468014]
NPT24776	CELL-LINE	B16-F1	Mus musculus	Activity	=	22.5	%	PMID[468014]
NPT24776	CELL-LINE	B16-F1	Mus musculus	Activity	=	15.5	%	PMID[468014]
NPT24776	CELL-LINE	B16-F1	Mus musculus	Activity	=	6.3	%	PMID[468014]
NPT24776	CELL-LINE	B16-F1	Mus musculus	Activity	=	2.41	cm3	PMID[468014]
NPT24776	CELL-LINE	B16-F1	Mus musculus	Activity	=	2.33	cm3	PMID[468014]
NPT32	Organism	Mus musculus	Mus musculus	Flu intensity	=	2.9	n.a.	PMID[468014]
NPT32	Organism	Mus musculus	Mus musculus	Flu intensity	=	2.3	n.a.	PMID[468014]
NPT32	Organism	Mus musculus	Mus musculus	Flu intensity	=	6.6	n.a.	PMID[468014]
NPT32	Organism	Mus musculus	Mus musculus	Flu intensity	=	3.2	n.a.	PMID[468014]
NPT32	Organism	Mus musculus	Mus musculus	Flu intensity	=	2.5	n.a.	PMID[468014]
NPT32	Organism	Mus musculus	Mus musculus	Flu intensity	=	1.1	n.a.	PMID[468014]
NPT20555	ORGANISM	SARS-CoV-2	Severe acute respiratory syndrome coronavirus 2	IC50	>	20000.0	nM	PMID[468015]
NPT20555	ORGANISM	SARS-CoV-2	Severe acute respiratory syndrome coronavirus 2	IC50	>	19952.62	nM	PMID[468015]

☑ 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 NPC296643 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	294
0.1-0.2	1157
0.2-0.3	2860
0.3-0.4	6630
0.4-0.5	10459
0.5-0.6	6911
0.6-0.7	9695
0.7-0.8	4127
0.8-0.85	422
0.85-0.9	126
0.9-0.95	14
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9571	High Similarity	NPC23677
0.9478	High Similarity	NPC169398
0.927	High Similarity	NPC469364
0.927	High Similarity	NPC101686
0.927	High Similarity	NPC65262
0.9065	High Similarity	NPC64141
0.9065	High Similarity	NPC197316
0.9065	High Similarity	NPC472350
0.9065	High Similarity	NPC89105
0.9065	High Similarity	NPC68092
0.9065	High Similarity	NPC81515
0.9065	High Similarity	NPC476383
0.9051	High Similarity	NPC34293
0.9051	High Similarity	NPC886
0.9051	High Similarity	NPC287597
0.9044	High Similarity	NPC473285
0.9034	High Similarity	NPC69367
0.8993	High Similarity	NPC476376
0.8993	High Similarity	NPC260425
0.8986	High Similarity	NPC476870
0.8986	High Similarity	NPC475484
0.8966	High Similarity	NPC478242
0.8963	High Similarity	NPC229784
0.8963	High Similarity	NPC477294
0.8963	High Similarity	NPC477293
0.8936	High Similarity	NPC134405
0.8936	High Similarity	NPC476385
0.8936	High Similarity	NPC476377
0.8936	High Similarity	NPC47471
0.8929	High Similarity	NPC328273
0.8929	High Similarity	NPC220942
0.8929	High Similarity	NPC205195
0.8929	High Similarity	NPC171134
0.8929	High Similarity	NPC321184
0.8929	High Similarity	NPC321638
0.8913	High Similarity	NPC471883
0.8912	High Similarity	NPC203664
0.8889	High Similarity	NPC232880
0.8881	High Similarity	NPC202391
0.8881	High Similarity	NPC296659
0.8873	High Similarity	NPC265648
0.8873	High Similarity	NPC222433
0.8873	High Similarity	NPC140502
0.8865	High Similarity	NPC473799
0.8865	High Similarity	NPC475530
0.8857	High Similarity	NPC100558
0.8857	High Similarity	NPC84789
0.8857	High Similarity	NPC78363
0.8857	High Similarity	NPC302583
0.8857	High Similarity	NPC310252
0.8849	High Similarity	NPC123988
0.8841	High Similarity	NPC254398
0.8832	High Similarity	NPC219677
0.8819	High Similarity	NPC100998
0.8819	High Similarity	NPC34587
0.8819	High Similarity	NPC34927
0.8819	High Similarity	NPC252292
0.8819	High Similarity	NPC476382
0.8815	High Similarity	NPC476873
0.8811	High Similarity	NPC175214
0.8811	High Similarity	NPC247032
0.8811	High Similarity	NPC476397
0.8811	High Similarity	NPC269141
0.8811	High Similarity	NPC205864
0.8811	High Similarity	NPC264632
0.8811	High Similarity	NPC96795
0.8811	High Similarity	NPC476384
0.8811	High Similarity	NPC76406
0.8811	High Similarity	NPC476381
0.8811	High Similarity	NPC476375
0.8811	High Similarity	NPC112
0.8811	High Similarity	NPC476380
0.8811	High Similarity	NPC476378
0.8811	High Similarity	NPC119537
0.8811	High Similarity	NPC298257
0.8808	High Similarity	NPC469384
0.8808	High Similarity	NPC179914
0.8786	High Similarity	NPC470572
0.8786	High Similarity	NPC157554
0.8776	High Similarity	NPC12006
0.8768	High Similarity	NPC473924
0.8759	High Similarity	NPC212808
0.875	High Similarity	NPC196063
0.875	High Similarity	NPC296954
0.875	High Similarity	NPC141455
0.875	High Similarity	NPC64195
0.875	High Similarity	NPC300894
0.8742	High Similarity	NPC286919
0.8742	High Similarity	NPC475663
0.8742	High Similarity	NPC187205
0.8725	High Similarity	NPC246893
0.8699	High Similarity	NPC232992
0.8686	High Similarity	NPC469549
0.8681	High Similarity	NPC40305
0.8681	High Similarity	NPC105005
0.8681	High Similarity	NPC478239
0.8681	High Similarity	NPC469367
0.8671	High Similarity	NPC186406
0.8662	High Similarity	NPC226005
0.8662	High Similarity	NPC31745
0.8662	High Similarity	NPC220936
0.8662	High Similarity	NPC100389
0.8658	High Similarity	NPC106818
0.8652	High Similarity	NPC472132
0.8643	High Similarity	NPC35731
0.8639	High Similarity	NPC28776
0.8639	High Similarity	NPC473138
0.8636	High Similarity	NPC145847
0.863	High Similarity	NPC143246
0.863	High Similarity	NPC475539
0.863	High Similarity	NPC474268
0.863	High Similarity	NPC119773
0.863	High Similarity	NPC473867
0.863	High Similarity	NPC229505
0.8621	High Similarity	NPC63304
0.8621	High Similarity	NPC251062
0.8621	High Similarity	NPC110063
0.8621	High Similarity	NPC184464
0.8618	High Similarity	NPC226759
0.8611	High Similarity	NPC157816
0.8603	High Similarity	NPC471157
0.8601	High Similarity	NPC202700
0.86	High Similarity	NPC87403
0.86	High Similarity	NPC299706
0.86	High Similarity	NPC245615
0.86	High Similarity	NPC61604
0.86	High Similarity	NPC157898
0.86	High Similarity	NPC115466
0.8591	High Similarity	NPC478249
0.8591	High Similarity	NPC269914
0.8591	High Similarity	NPC140151
0.8581	High Similarity	NPC94871
0.8581	High Similarity	NPC476386
0.8581	High Similarity	NPC471062
0.8581	High Similarity	NPC106138
0.8581	High Similarity	NPC306890
0.8581	High Similarity	NPC476398
0.8581	High Similarity	NPC96599
0.8581	High Similarity	NPC473427
0.8581	High Similarity	NPC259347
0.8581	High Similarity	NPC109990
0.8581	High Similarity	NPC470933
0.8571	High Similarity	NPC18789
0.8562	High Similarity	NPC287615
0.8562	High Similarity	NPC262182
0.8562	High Similarity	NPC216819
0.8562	High Similarity	NPC83743
0.8562	High Similarity	NPC475528
0.8561	High Similarity	NPC248307
0.8561	High Similarity	NPC235294
0.8561	High Similarity	NPC46137
0.8561	High Similarity	NPC65942
0.8553	High Similarity	NPC471405
0.8553	High Similarity	NPC228357
0.8552	High Similarity	NPC293154
0.8552	High Similarity	NPC186296
0.8543	High Similarity	NPC472127
0.8543	High Similarity	NPC327032
0.8543	High Similarity	NPC191046
0.8543	High Similarity	NPC194095
0.8543	High Similarity	NPC472128
0.854	High Similarity	NPC106677
0.854	High Similarity	NPC288416
0.854	High Similarity	NPC108659
0.854	High Similarity	NPC231607
0.854	High Similarity	NPC264900
0.854	High Similarity	NPC79715
0.8533	High Similarity	NPC478268
0.8529	High Similarity	NPC126991
0.8529	High Similarity	NPC83218
0.8523	High Similarity	NPC240592
0.8523	High Similarity	NPC470927
0.8523	High Similarity	NPC117346
0.8523	High Similarity	NPC257970
0.8523	High Similarity	NPC470934
0.8523	High Similarity	NPC188393
0.8521	High Similarity	NPC37468
0.8521	High Similarity	NPC199459
0.8521	High Similarity	NPC177035
0.8521	High Similarity	NPC186418
0.8521	High Similarity	NPC52277
0.8507	High Similarity	NPC266045
0.8503	High Similarity	NPC476865
0.8503	High Similarity	NPC199928
0.85	High Similarity	NPC254275
0.8497	Intermediate Similarity	NPC472860
0.8497	Intermediate Similarity	NPC49173
0.8493	Intermediate Similarity	NPC476867
0.8493	Intermediate Similarity	NPC297342
0.8493	Intermediate Similarity	NPC292443
0.8493	Intermediate Similarity	NPC232228
0.8487	Intermediate Similarity	NPC38699
0.8487	Intermediate Similarity	NPC172920
0.8487	Intermediate Similarity	NPC156624
0.8487	Intermediate Similarity	NPC10205
0.8487	Intermediate Similarity	NPC131532
0.8477	Intermediate Similarity	NPC471874
0.8477	Intermediate Similarity	NPC44730
0.8467	Intermediate Similarity	NPC94179
0.8462	Intermediate Similarity	NPC304152

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 NPC296643 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	251
0.1-0.2	742
0.2-0.3	1682
0.3-0.4	2754
0.4-0.5	2047
0.5-0.6	1136
0.6-0.7	484
0.7-0.8	52
0.8-0.85	1
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9065	High Similarity	NPD7266	Discontinued
0.8212	Intermediate Similarity	NPD1653	Approved
0.8176	Intermediate Similarity	NPD6190	Approved
0.8098	Intermediate Similarity	NPD7685	Pre-registration
0.7914	Intermediate Similarity	NPD7054	Approved
0.7866	Intermediate Similarity	NPD7472	Approved
0.7853	Intermediate Similarity	NPD7228	Approved
0.7771	Intermediate Similarity	NPD7251	Discontinued
0.7758	Intermediate Similarity	NPD7074	Phase 3
0.775	Intermediate Similarity	NPD6234	Discontinued
0.7744	Intermediate Similarity	NPD3818	Discontinued
0.7725	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7712	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7711	Intermediate Similarity	NPD6797	Phase 2
0.7687	Intermediate Similarity	NPD230	Phase 1
0.7658	Intermediate Similarity	NPD37	Approved
0.7625	Intermediate Similarity	NPD4965	Approved
0.7625	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7625	Intermediate Similarity	NPD4966	Approved
0.7625	Intermediate Similarity	NPD4967	Phase 2
0.7619	Intermediate Similarity	NPD7808	Phase 3
0.7588	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7578	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7534	Intermediate Similarity	NPD3027	Phase 3
0.7516	Intermediate Similarity	NPD8166	Discontinued
0.7439	Intermediate Similarity	NPD7199	Phase 2
0.7391	Intermediate Similarity	NPD8455	Phase 2
0.7383	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7383	Intermediate Similarity	NPD1613	Approved
0.7361	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD7240	Approved
0.7343	Intermediate Similarity	NPD1091	Approved
0.7342	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD6674	Discontinued
0.7329	Intermediate Similarity	NPD1934	Approved
0.729	Intermediate Similarity	NPD4628	Phase 3
0.7285	Intermediate Similarity	NPD6653	Approved
0.7284	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7251	Intermediate Similarity	NPD6559	Discontinued
0.7246	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD3817	Phase 2
0.7237	Intermediate Similarity	NPD7097	Phase 1
0.7237	Intermediate Similarity	NPD4978	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD3705	Approved
0.7205	Intermediate Similarity	NPD4380	Phase 2
0.7202	Intermediate Similarity	NPD6166	Phase 2
0.7202	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7183	Intermediate Similarity	NPD9545	Approved
0.7178	Intermediate Similarity	NPD2801	Approved
0.7168	Intermediate Similarity	NPD8313	Approved
0.7168	Intermediate Similarity	NPD8312	Approved
0.7159	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD7966	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD7075	Discontinued
0.7133	Intermediate Similarity	NPD1357	Approved
0.7126	Intermediate Similarity	NPD8127	Discontinued
0.7114	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD6233	Phase 2
0.7079	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7076	Intermediate Similarity	NPD5844	Phase 1
0.7055	Intermediate Similarity	NPD9269	Phase 2
0.705	Intermediate Similarity	NPD228	Approved
0.7047	Intermediate Similarity	NPD5736	Approved
0.7047	Intermediate Similarity	NPD9494	Approved
0.7047	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD1511	Approved
0.7037	Intermediate Similarity	NPD3455	Phase 2
0.7033	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7029	Intermediate Similarity	NPD3022	Approved
0.7029	Intermediate Similarity	NPD3021	Approved
0.702	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD1652	Phase 2
0.7	Intermediate Similarity	NPD8389	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD6355	Discontinued
0.6988	Remote Similarity	NPD3882	Suspended
0.6973	Remote Similarity	NPD7680	Approved
0.697	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.697	Remote Similarity	NPD1465	Phase 2
0.6968	Remote Similarity	NPD7033	Discontinued
0.6962	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6962	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6962	Remote Similarity	NPD4110	Phase 3
0.6962	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD7473	Discontinued
0.6957	Remote Similarity	NPD1512	Approved
0.6954	Remote Similarity	NPD7095	Approved
0.6943	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD7458	Discontinued
0.6932	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD826	Approved
0.6928	Remote Similarity	NPD4060	Phase 1
0.6928	Remote Similarity	NPD5402	Approved
0.6928	Remote Similarity	NPD5353	Approved
0.6928	Remote Similarity	NPD825	Approved
0.6923	Remote Similarity	NPD9570	Approved
0.6909	Remote Similarity	NPD6801	Discontinued
0.6908	Remote Similarity	NPD6798	Discontinued
0.6899	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6883	Remote Similarity	NPD5124	Phase 1
0.6883	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD6232	Discontinued
0.6875	Remote Similarity	NPD5536	Phase 2
0.6871	Remote Similarity	NPD3686	Approved
0.6871	Remote Similarity	NPD3687	Approved
0.6867	Remote Similarity	NPD7819	Suspended
0.6863	Remote Similarity	NPD6663	Approved
0.6849	Remote Similarity	NPD1778	Approved
0.6848	Remote Similarity	NPD6386	Approved
0.6848	Remote Similarity	NPD6385	Approved
0.6846	Remote Similarity	NPD3225	Approved
0.6824	Remote Similarity	NPD1608	Approved
0.6821	Remote Similarity	NPD3751	Discontinued
0.6821	Remote Similarity	NPD2861	Phase 2
0.6818	Remote Similarity	NPD3620	Phase 2
0.6818	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6815	Remote Similarity	NPD2935	Discontinued
0.681	Remote Similarity	NPD5403	Approved
0.6797	Remote Similarity	NPD3268	Approved
0.6797	Remote Similarity	NPD3764	Approved
0.6784	Remote Similarity	NPD3787	Discontinued
0.6781	Remote Similarity	NPD9268	Approved
0.6774	Remote Similarity	NPD4340	Discontinued
0.6774	Remote Similarity	NPD447	Suspended
0.6774	Remote Similarity	NPD555	Phase 2
0.6774	Remote Similarity	NPD1933	Approved
0.6772	Remote Similarity	NPD5762	Approved
0.6772	Remote Similarity	NPD5763	Approved
0.6772	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.677	Remote Similarity	NPD5058	Phase 3
0.6766	Remote Similarity	NPD2978	Approved
0.6766	Remote Similarity	NPD2977	Approved
0.6763	Remote Similarity	NPD1358	Approved
0.6761	Remote Similarity	NPD7843	Approved
0.676	Remote Similarity	NPD8150	Discontinued
0.6757	Remote Similarity	NPD422	Phase 1
0.6753	Remote Similarity	NPD4062	Phase 3
0.6747	Remote Similarity	NPD7411	Suspended
0.6736	Remote Similarity	NPD7157	Approved
0.6735	Remote Similarity	NPD5126	Approved
0.6735	Remote Similarity	NPD5125	Phase 3
0.6728	Remote Similarity	NPD6799	Approved
0.6726	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6713	Remote Similarity	NPD5283	Phase 1
0.671	Remote Similarity	NPD943	Approved
0.6709	Remote Similarity	NPD2438	Suspended
0.6702	Remote Similarity	NPD7435	Discontinued
0.6691	Remote Similarity	NPD3134	Approved
0.669	Remote Similarity	NPD969	Suspended
0.6689	Remote Similarity	NPD2797	Approved
0.6689	Remote Similarity	NPD3496	Discontinued
0.6689	Remote Similarity	NPD3094	Phase 2
0.6689	Remote Similarity	NPD6362	Approved
0.6687	Remote Similarity	NPD5401	Approved
0.6687	Remote Similarity	NPD7028	Phase 2
0.6667	Remote Similarity	NPD8434	Phase 2
0.6667	Remote Similarity	NPD5585	Approved
0.6667	Remote Similarity	NPD7038	Approved
0.6667	Remote Similarity	NPD8320	Phase 1
0.6667	Remote Similarity	NPD8319	Approved
0.6667	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4908	Phase 1
0.6667	Remote Similarity	NPD6002	Phase 3
0.6667	Remote Similarity	NPD2629	Approved
0.6667	Remote Similarity	NPD5494	Approved
0.6667	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6005	Phase 3
0.6667	Remote Similarity	NPD6004	Phase 3
0.6667	Remote Similarity	NPD7039	Approved
0.6647	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD3750	Approved
0.6646	Remote Similarity	NPD1510	Phase 2
0.6646	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6645	Remote Similarity	NPD258	Approved
0.6645	Remote Similarity	NPD259	Phase 1
0.6645	Remote Similarity	NPD257	Approved
0.6645	Remote Similarity	NPD5647	Approved
0.663	Remote Similarity	NPD6841	Approved
0.663	Remote Similarity	NPD6843	Phase 3
0.663	Remote Similarity	NPD6842	Approved
0.6625	Remote Similarity	NPD2424	Discontinued
0.6625	Remote Similarity	NPD1549	Phase 2
0.6622	Remote Similarity	NPD9384	Approved
0.6622	Remote Similarity	NPD9381	Approved
0.6622	Remote Similarity	NPD17	Approved
0.6615	Remote Similarity	NPD8151	Discontinued
0.6604	Remote Similarity	NPD6100	Approved
0.6604	Remote Similarity	NPD6099	Approved
0.6603	Remote Similarity	NPD4140	Approved
0.6596	Remote Similarity	NPD2684	Approved
0.6591	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.6585	Remote Similarity	NPD4160	Clinical (unspecified phase)
0.6585	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6585	Remote Similarity	NPD3688	Clinical (unspecified phase)
0.6585	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6585	Remote Similarity	NPD3146	Approved
0.6584	Remote Similarity	NPD5698	Clinical (unspecified phase)

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