NPASS Compound

Structure

CID214770 OpenBabel06191716002D 31 35 0 0 1 0 0 0 0 0999 V2000 -4.3932 5.4195 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9985 4.8974 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8836 3.1612 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6901 -2.9585 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5626 -2.4546 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6904 1.9823 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6896 -1.0083 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7903 3.5659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7437 3.7682 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4889 2.6391 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0006 -1.9512 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8445 -1.4636 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3788 0.9740 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5337 -0.4871 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3785 -0.0010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6893 0.0005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8453 1.4626 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0003 0.9750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8448 0.4881 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0451 4.6951 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5355 2.4367 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5352 1.4621 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8453 -1.4632 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8448 -0.4880 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5340 -1.4627 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6898 -1.9507 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6901 0.9745 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6899 -0.0005 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8451 -0.4876 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.4003 -1.9623 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 20 1 0 0 0 0 2 20 1 0 0 0 0 4 26 1 0 0 0 0 5 26 1 0 0 0 0 6 27 1 0 0 0 0 8 9 1 0 0 0 0 8 10 1 0 0 0 0 9 20 2 0 0 0 0 10 21 1 0 0 0 0 11 12 1 0 0 0 0 11 23 1 0 0 0 0 12 24 1 0 0 0 0 13 15 1 0 0 0 0 13 22 1 0 0 0 0 14 16 1 0 0 0 0 14 25 1 0 0 0 0 15 28 1 0 0 0 0 16 29 1 0 0 0 0 17 18 1 0 0 0 0 17 27 1 0 0 0 0 19 29 1 0 0 0 0 19 30 1 0 0 0 0 21 3 1 1 0 0 0 21 22 1 0 0 0 0 22 27 1 6 0 0 0 23 26 1 0 0 0 0 23 29 1 6 0 0 0 24 28 1 1 0 0 0 24 30 1 0 0 0 0 25 26 1 0 0 0 0 25 31 2 0 0 0 0 27 28 1 6 0 0 0 28 7 1 1 0 0 0 29 30 1 1 0 0 0 30 18 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	424.37
Volume:	488.171
LogP:	8.136
LogD:	5.821
LogS:	-6.819
# Rotatable Bonds:	4
TPSA:	17.07
# H-Bond Aceptor:	1
# H-Bond Donor:	0
# Rings:	5
# Heavy Atoms:	1

MedChem Properties

QED Drug-Likeness Score:	0.414
Synthetic Accessibility Score:	5.364
Fsp3:	0.9
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.115
MDCK Permeability:	9.925998710968997e-06
Pgp-inhibitor:	0.019
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.994
30% Bioavailability (F30%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.079
Plasma Protein Binding (PPB):	95.86158752441406%
Volume Distribution (VD):	1.326
Pgp-substrate:	1.3618568181991577%

ADMET: Metabolism

CYP1A2-inhibitor:	0.068
CYP1A2-substrate:	0.306
CYP2C19-inhibitor:	0.186
CYP2C19-substrate:	0.957
CYP2C9-inhibitor:	0.231
CYP2C9-substrate:	0.706
CYP2D6-inhibitor:	0.234
CYP2D6-substrate:	0.327
CYP3A4-inhibitor:	0.856
CYP3A4-substrate:	0.621

ADMET: Excretion

Clearance (CL):	11.471
Half-life (T1/2):	0.102

ADMET: Toxicity

hERG Blockers:	0.489
Human Hepatotoxicity (H-HT):	0.613
Drug-inuced Liver Injury (DILI):	0.104
AMES Toxicity:	0.003
Rat Oral Acute Toxicity:	0.13
Maximum Recommended Daily Dose:	0.594
Skin Sensitization:	0.928
Carcinogencity:	0.186
Eye Corrosion:	0.179
Eye Irritation:	0.511
Respiratory Toxicity:	0.948

Download Data

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

Natural Product: NPC214770

Natural Product ID:	NPC214770
*Common Name:**	Cycloartenone
IUPAC Name:	n.a.
Synonyms:	Cycloartenone
Standard InCHIKey:	NAJCQAAOHKVCES-ZZOQNIIDSA-N
Standard InCHI:	InChI=1S/C30H48O/c1-20(2)9-8-10-21(3)22-13-15-28(7)24-12-11-23-26(4,5)25(31)14-16-29(23)19-30(24,29)18-17-27(22,28)6/h9,21-24H,8,10-19H2,1-7H3/t21-,22-,23+,24+,27-,28+,29-,30+/m1/s1
SMILES:	CC(=CCC[C@H]([C@H]1CC[C@@]2([C@]1(C)CC[C@@]13[C@H]2CC[C@@H]2[C@]3(C1)CCC(=O)C2(C)C)C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL226084
PubChem CID:	12305360
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0002321] Cycloartanols and derivatives

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1007/s11746-997-0093-1]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	n.a.	Wrocław, Poland	2004–2005	DOI[10.1016/J.FOODCHEM.2006.08.014]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	n.a.	retail stores, supermarkets and market stalls in Forssa and in the Helsinki area	2003–2005	DOI[10.1016/j.jfca.2006.05.007]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1021/jf950732o]
NPO29314	Mangifera indica	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1246/bcsj.30.618]
NPO25443	Citrus reticulata	Species	Rutaceae	Eukaryota	n.a.	fruit	n.a.	PMID[10606547]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10775096]
NPO17694	Nicotiana tabacum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11559179]
NPO10031	Euphorbia antiquorum	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11858748]
NPO29276	Juglans nigra	Species	Juglandaceae	Eukaryota	n.a.	leaf	n.a.	PMID[14727919]
NPO29276	Juglans nigra	Species	Juglandaceae	Eukaryota	n.a.	bark	n.a.	PMID[14727919]
NPO29276	Juglans nigra	Species	Juglandaceae	Eukaryota	n.a.	xylem	n.a.	PMID[14727919]
NPO29276	Juglans nigra	Species	Juglandaceae	Eukaryota	n.a.	root	n.a.	PMID[14727919]
NPO9498	Papaver somniferum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15019787]
NPO10828	Adina racemosa	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15043423]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	n.a.	root	n.a.	PMID[1622242]
NPO29530	Kaempferia marginata	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16309313]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16659156]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16668466]
NPO27743	Aaptos aaptos	Species	Suberitidae	Eukaryota	n.a.	n.a.	n.a.	PMID[17716892]
NPO17694	Nicotiana tabacum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18001808]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18460139]
NPO29381	Trichilia rubescens	Species	Meliaceae	Eukaryota	leaves	Kibale National Park, Uganda	2000-2001	PMID[19299148]
NPO2865	Abrus precatorius	Species	Fabaceae	Eukaryota	aerial parts	n.a.	n.a.	PMID[19299148]
NPO28864	Nauclea officinalis	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19299148]
NPO8666	Acorus tatarinowii	Species	Acoraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20476749]
NPO17694	Nicotiana tabacum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20954721]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20963508]
NPO5681	Acorus gramineus	Species	Acoraceae	Eukaryota	Rhizomes	n.a.	n.a.	PMID[21936523]
NPO5681	Acorus gramineus	Species	Acoraceae	Eukaryota	n.a.	rhizome	n.a.	PMID[21936523]
NPO9498	Papaver somniferum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22029392]
NPO2865	Abrus precatorius	Species	Fabaceae	Eukaryota	n.a.	leaf	n.a.	PMID[22210168]
NPO2865	Abrus precatorius	Species	Fabaceae	Eukaryota	n.a.	stem	n.a.	PMID[22210168]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22537213]
NPO5681	Acorus gramineus	Species	Acoraceae	Eukaryota	rhizomes	n.a.	n.a.	PMID[22951040]
NPO17694	Nicotiana tabacum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23479199]
NPO9498	Papaver somniferum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23517479]
NPO8666	Acorus tatarinowii	Species	Acoraceae	Eukaryota	n.a.	rhizome	n.a.	PMID[23713285]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	Seeds	Tekirdag, Turkey		PMID[24499198]
NPO10031	Euphorbia antiquorum	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24840014]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25053043]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25070365]
NPO27743	Aaptos aaptos	Species	Suberitidae	Eukaryota	n.a.	South China Sea	n.a.	PMID[25211032]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25369450]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	n.a.	seed	n.a.	PMID[25369450]
NPO8666	Acorus tatarinowii	Species	Acoraceae	Eukaryota	rhizomes	n.a.	n.a.	PMID[26296476]
NPO8666	Acorus tatarinowii	Species	Acoraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26305406]
NPO2865	Abrus precatorius	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[2691636]
NPO2865	Abrus precatorius	Species	Fabaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[2691636]
NPO29314	Mangifera indica	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27466882]
NPO41067	Trigona minor	Species	Apidae	Eukaryota	n.a.	n.a.	n.a.	PMID[28783356]
NPO8666	Acorus tatarinowii	Species	Acoraceae	Eukaryota	Rhizomes	n.a.	n.a.	PMID[29116780]
NPO4490	Cephalotaxus sinensis	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[29182349]
NPO4055	Aspergillus unguis	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31117521]
NPO10031	Euphorbia antiquorum	Species	Euphorbiaceae	Eukaryota	Stems	n.a.	n.a.	PMID[31180680]
NPO29530	Kaempferia marginata	Species	Zingiberaceae	Eukaryota	Rhizomes	n.a.	n.a.	PMID[31873014]
NPO29276	Juglans nigra	Species	Juglandaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO29276	Juglans nigra	Species	Juglandaceae	Eukaryota	Pericarp	n.a.	n.a.	Database[FooDB]
NPO25443	Citrus reticulata	Species	Rutaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	Pericarp	n.a.	n.a.	Database[FooDB]
NPO29314	Mangifera indica	Species	Anacardiaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	Cotyledon	n.a.	n.a.	Database[FooDB]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	Root	n.a.	n.a.	Database[FooDB]
NPO29276	Juglans nigra	Species	Juglandaceae	Eukaryota	Essential Oil	n.a.	n.a.	Database[FooDB]
NPO9498	Papaver somniferum	Species	Papaveraceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO29314	Mangifera indica	Species	Anacardiaceae	Eukaryota	Flower	n.a.	n.a.	Database[FooDB]
NPO25443	Citrus reticulata	Species	Rutaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO29276	Juglans nigra	Species	Juglandaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO29276	Juglans nigra	Species	Juglandaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO29314	Mangifera indica	Species	Anacardiaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO29314	Mangifera indica	Species	Anacardiaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO25443	Citrus reticulata	Species	Rutaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO29276	Juglans nigra	Species	Juglandaceae	Eukaryota	Shoot	n.a.	n.a.	Database[FooDB]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO9498	Papaver somniferum	Species	Papaveraceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	Sprout Seedling	n.a.	n.a.	Database[FooDB]
NPO29314	Mangifera indica	Species	Anacardiaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	Stem	n.a.	n.a.	Database[FooDB]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	Hypocotyl	n.a.	n.a.	Database[FooDB]
NPO9498	Papaver somniferum	Species	Papaveraceae	Eukaryota	Latex Exudate	n.a.	n.a.	Database[FooDB]
NPO29276	Juglans nigra	Species	Juglandaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	Testa	n.a.	n.a.	Database[FooDB]
NPO29314	Mangifera indica	Species	Anacardiaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO9498	Papaver somniferum	Species	Papaveraceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	Oil	n.a.	n.a.	Database[FooDB]
NPO9498	Papaver somniferum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO4490	Cephalotaxus sinensis	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13272	Ulva lactuca	Species	Ulvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1459	Euonymus mupinensis	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28949	Croton cumingii	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28864	Nauclea officinalis	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5681	Acorus gramineus	Species	Acoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17694	Nicotiana tabacum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29004	Ruta pinnata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2865	Abrus precatorius	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25443	Citrus reticulata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5665	Ulva pertusa	Species	Ulvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8666	Acorus tatarinowii	Species	Acoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29276	Juglans nigra	Species	Juglandaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO10031	Euphorbia antiquorum	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29314	Mangifera indica	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO30490	Citrus chachiensis	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[MetaboLights]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	n.a.	seed	n.a.	Database[MetaboLights]
NPO25443	Citrus reticulata	Species	Rutaceae	Eukaryota	Fruits	n.a.		Database[Phenol-Explorer]
NPO25443	Citrus reticulata	Species	Rutaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO29314	Mangifera indica	Species	Anacardiaceae	Eukaryota	Fruits	n.a.		Database[Phenol-Explorer]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	Seeds	n.a.		Database[Phenol-Explorer]
NPO5665	Ulva pertusa	Species	Ulvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9498	Papaver somniferum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1459	Euonymus mupinensis	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13272	Ulva lactuca	Species	Ulvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29344	Parabenzoin trilobum	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TCMID]
NPO4490	Cephalotaxus sinensis	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29530	Kaempferia marginata	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28949	Croton cumingii	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17694	Nicotiana tabacum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10031	Euphorbia antiquorum	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28864	Nauclea officinalis	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2865	Abrus precatorius	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7676	Caesalpinia japonica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4055	Aspergillus unguis	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29276	Juglans nigra	Species	Juglandaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29004	Ruta pinnata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5681	Acorus gramineus	Species	Acoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28805	Thymus piperella	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8666	Acorus tatarinowii	Species	Acoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29314	Mangifera indica	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25443	Citrus reticulata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17694	Nicotiana tabacum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO2865	Abrus precatorius	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO29276	Juglans nigra	Species	Juglandaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO1459	Euonymus mupinensis	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO25443	Citrus reticulata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO30490	Citrus chachiensis	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO28864	Nauclea officinalis	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO5665	Ulva pertusa	Species	Ulvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO8666	Acorus tatarinowii	Species	Acoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO4490	Cephalotaxus sinensis	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO9498	Papaver somniferum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO29314	Mangifera indica	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO13272	Ulva lactuca	Species	Ulvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO9498	Papaver somniferum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO5681	Acorus gramineus	Species	Acoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO25443	Citrus reticulata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO8666	Acorus tatarinowii	Species	Acoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO28949	Croton cumingii	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28971	Bersama yangambiensis	Species	Melianthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29189	Castanopsis sclerophylla	Species	Fagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1245	Eunicella cavolinii	Species	Gorgoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO466	Chrysanthemum lacustre	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29363	Aconitum nevadense	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4055	Aspergillus unguis	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29127	Cystophora scalaris	Species	Sargassaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13272	Ulva lactuca	Species	Ulvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26192	Cordylanthus kingii	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13818	Narcissus concolor	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25981	Crinipellis scabella	Species	Marasmiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29381	Trichilia rubescens	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28824	Forsteronia refracta	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1459	Euonymus mupinensis	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28784	Alseodaphne corneri	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29004	Ruta pinnata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29530	Kaempferia marginata	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9498	Papaver somniferum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5447	Digitalis canariensis	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3744	Polycephalomyces nipponicus	Species	Ophiocordycipitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21552	Oreaster nodosus	Species	Oreasteridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28898	Grewia mollis	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29510	Aulacocephalus temmincki	Species	Serranidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28864	Nauclea officinalis	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9157	Rubrivivax gelatinosus	Species	n.a.	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO29400	Conocephalum japonicum	Species	Conocephalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2865	Abrus precatorius	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27269	Annona impressivenia	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4244	Doodia picta	Species	Blechnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29488	Sophora angustifolia	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29446	Stevia polycephala	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4490	Cephalotaxus sinensis	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11422	Aster yunnanensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29142	Kaunia saltensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29344	Parabenzoin trilobum	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO29415	Hovenia acerba	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9052	Pseudocyphellaria norvegica	Species	Lobariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29154	Heliotropium floridum	Species	Heliotropiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27743	Aaptos aaptos	Species	Suberitidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10409	Methanothermobacter thermautotrophicus	Species	Methanobacteriaceae	Archaea	n.a.	n.a.	n.a.	Database[UNPD]
NPO28805	Thymus piperella	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29292	Teucrium depressum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29203	Gymnocarpium robertianum	Species	Cystopteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29068	Papilio phorcas	Species	Papilionidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25443	Citrus reticulata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8666	Acorus tatarinowii	Species	Acoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29314	Mangifera indica	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5665	Ulva pertusa	Species	Ulvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28937	Heterotheca grandiflora	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7956	Discaria chacaye	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28918	Ophiolepis superba	Species	Ophiolepididae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29450	Streptomyces parvisporogenes	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO10828	Adina racemosa	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28845	Eragrostis viscosa	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29242	Salvia dorrii	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10031	Euphorbia antiquorum	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17694	Nicotiana tabacum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29225	Oncoba echinata	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29047	Disynaphia halimifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29276	Juglans nigra	Species	Juglandaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3340	Fridericia chica	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7676	Caesalpinia japonica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	1
Others	7

Activity Type	# Activity
Cell Line	2
Organism	5
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT80	Cell Line	Raji	Homo sapiens	Activity	=	70.0	%	PMID[450478]
NPT461	Cell Line	PANC-1	Homo sapiens	PC50	>	100.0	uM	PMID[450479]
NPT164	Organism	Human herpesvirus 4	Human herpesvirus 4	Inhibition	=	2.3	%	PMID[450478]
NPT164	Organism	Human herpesvirus 4	Human herpesvirus 4	Inhibition	=	24.6	%	PMID[450478]
NPT164	Organism	Human herpesvirus 4	Human herpesvirus 4	Inhibition	=	71.3	%	PMID[450478]
NPT164	Organism	Human herpesvirus 4	Human herpesvirus 4	Inhibition	=	92.6	%	PMID[450478]
NPT164	Organism	Human herpesvirus 4	Human herpesvirus 4	IC50	=	8.8	nM	PMID[450478]
NPT2	Others	Unspecified		Activity	=	1.5	n.a.	PMID[450478]

☑ 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 NPC214770 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	209
0.1-0.2	2425
0.2-0.3	16188
0.3-0.4	10081
0.4-0.5	6855
0.5-0.6	4958
0.6-0.7	1695
0.7-0.8	238
0.8-0.85	26
0.85-0.9	13
0.9-0.95	7
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC477856
0.9394	High Similarity	NPC20610
0.9385	High Similarity	NPC39462
0.9385	High Similarity	NPC189917
0.9385	High Similarity	NPC107704
0.9385	High Similarity	NPC96812
0.9385	High Similarity	NPC168824
0.9254	High Similarity	NPC182815
0.9143	High Similarity	NPC255650
0.9118	High Similarity	NPC159577
0.9118	High Similarity	NPC40574
0.9118	High Similarity	NPC282593
0.9118	High Similarity	NPC35734
0.9014	High Similarity	NPC69408
0.9	High Similarity	NPC255021
0.8986	High Similarity	NPC115023
0.8986	High Similarity	NPC470078
0.8971	High Similarity	NPC477857
0.8873	High Similarity	NPC293803
0.8857	High Similarity	NPC251705
0.8857	High Similarity	NPC303613
0.8857	High Similarity	NPC474228
0.8841	High Similarity	NPC307176
0.8806	High Similarity	NPC43300
0.8806	High Similarity	NPC323005
0.8714	High Similarity	NPC234707
0.8696	High Similarity	NPC139397
0.863	High Similarity	NPC91665
0.8592	High Similarity	NPC470044
0.8592	High Similarity	NPC470045
0.8571	High Similarity	NPC260040
0.8571	High Similarity	NPC2634
0.8571	High Similarity	NPC265782
0.8571	High Similarity	NPC251929
0.8551	High Similarity	NPC142754
0.8551	High Similarity	NPC82477
0.8551	High Similarity	NPC39157
0.8551	High Similarity	NPC296697
0.8507	High Similarity	NPC469662
0.8472	Intermediate Similarity	NPC309852
0.8451	Intermediate Similarity	NPC305501
0.8451	Intermediate Similarity	NPC54123
0.8429	Intermediate Similarity	NPC286814
0.8406	Intermediate Similarity	NPC220210
0.8406	Intermediate Similarity	NPC20181
0.84	Intermediate Similarity	NPC215843
0.8378	Intermediate Similarity	NPC470557
0.8358	Intermediate Similarity	NPC197238
0.8358	Intermediate Similarity	NPC202118
0.8333	Intermediate Similarity	NPC181743
0.8333	Intermediate Similarity	NPC16287
0.8333	Intermediate Similarity	NPC178025
0.8289	Intermediate Similarity	NPC474509
0.8267	Intermediate Similarity	NPC470052
0.8267	Intermediate Similarity	NPC82635
0.8235	Intermediate Similarity	NPC285371
0.8228	Intermediate Similarity	NPC60350
0.8219	Intermediate Similarity	NPC474796
0.8219	Intermediate Similarity	NPC474797
0.8219	Intermediate Similarity	NPC329866
0.8209	Intermediate Similarity	NPC60565
0.8194	Intermediate Similarity	NPC190035
0.8194	Intermediate Similarity	NPC5701
0.8154	Intermediate Similarity	NPC49575
0.8154	Intermediate Similarity	NPC230823
0.8154	Intermediate Similarity	NPC55004
0.8154	Intermediate Similarity	NPC267626
0.8143	Intermediate Similarity	NPC176107
0.8108	Intermediate Similarity	NPC473171
0.8082	Intermediate Similarity	NPC474488
0.8025	Intermediate Similarity	NPC476293
0.8	Intermediate Similarity	NPC474105
0.8	Intermediate Similarity	NPC92327
0.7973	Intermediate Similarity	NPC159497
0.7949	Intermediate Similarity	NPC147066
0.7945	Intermediate Similarity	NPC223187
0.7945	Intermediate Similarity	NPC225467
0.7941	Intermediate Similarity	NPC213152
0.7922	Intermediate Similarity	NPC170793
0.7922	Intermediate Similarity	NPC158846
0.7922	Intermediate Similarity	NPC90965
0.7848	Intermediate Similarity	NPC320514
0.7848	Intermediate Similarity	NPC472239
0.7846	Intermediate Similarity	NPC184819
0.7826	Intermediate Similarity	NPC165695
0.7826	Intermediate Similarity	NPC472306
0.7794	Intermediate Similarity	NPC25853
0.7794	Intermediate Similarity	NPC127582
0.7792	Intermediate Similarity	NPC469996
0.7778	Intermediate Similarity	NPC310992
0.7778	Intermediate Similarity	NPC260474
0.7778	Intermediate Similarity	NPC188292
0.7763	Intermediate Similarity	NPC469793
0.7763	Intermediate Similarity	NPC469796
0.7761	Intermediate Similarity	NPC266295
0.7761	Intermediate Similarity	NPC30215
0.7761	Intermediate Similarity	NPC94991
0.775	Intermediate Similarity	NPC21667
0.775	Intermediate Similarity	NPC470047
0.775	Intermediate Similarity	NPC470046
0.7727	Intermediate Similarity	NPC143597
0.7727	Intermediate Similarity	NPC151464
0.7722	Intermediate Similarity	NPC201912
0.7722	Intermediate Similarity	NPC4166
0.7722	Intermediate Similarity	NPC38350
0.7714	Intermediate Similarity	NPC212210
0.7714	Intermediate Similarity	NPC475124
0.7703	Intermediate Similarity	NPC181204
0.7692	Intermediate Similarity	NPC477371
0.7671	Intermediate Similarity	NPC256846
0.7654	Intermediate Similarity	NPC59453
0.7654	Intermediate Similarity	NPC214043
0.7654	Intermediate Similarity	NPC221758
0.7654	Intermediate Similarity	NPC85774
0.7654	Intermediate Similarity	NPC82902
0.7647	Intermediate Similarity	NPC259261
0.7647	Intermediate Similarity	NPC23217
0.7647	Intermediate Similarity	NPC276764
0.7647	Intermediate Similarity	NPC472304
0.7625	Intermediate Similarity	NPC311092
0.7625	Intermediate Similarity	NPC142253
0.7625	Intermediate Similarity	NPC477858
0.7625	Intermediate Similarity	NPC3511
0.7625	Intermediate Similarity	NPC193347
0.7625	Intermediate Similarity	NPC472867
0.7625	Intermediate Similarity	NPC260956
0.7595	Intermediate Similarity	NPC472478
0.759	Intermediate Similarity	NPC93778
0.7576	Intermediate Similarity	NPC200258
0.7568	Intermediate Similarity	NPC246722
0.7568	Intermediate Similarity	NPC151045
0.7564	Intermediate Similarity	NPC228911
0.7564	Intermediate Similarity	NPC115515
0.7564	Intermediate Similarity	NPC63020
0.7561	Intermediate Similarity	NPC137493
0.7561	Intermediate Similarity	NPC29447
0.7561	Intermediate Similarity	NPC470223
0.7561	Intermediate Similarity	NPC471224
0.7561	Intermediate Similarity	NPC469948
0.7561	Intermediate Similarity	NPC474218
0.7558	Intermediate Similarity	NPC12722
0.7558	Intermediate Similarity	NPC478129
0.7536	Intermediate Similarity	NPC270042
0.7534	Intermediate Similarity	NPC87141
0.7532	Intermediate Similarity	NPC474463
0.7532	Intermediate Similarity	NPC20466
0.7531	Intermediate Similarity	NPC83569
0.7531	Intermediate Similarity	NPC41539
0.7531	Intermediate Similarity	NPC167103
0.7531	Intermediate Similarity	NPC69279
0.75	Intermediate Similarity	NPC477372
0.75	Intermediate Similarity	NPC27610
0.75	Intermediate Similarity	NPC211641
0.75	Intermediate Similarity	NPC193360
0.75	Intermediate Similarity	NPC56905
0.75	Intermediate Similarity	NPC259252
0.75	Intermediate Similarity	NPC176171
0.747	Intermediate Similarity	NPC469994
0.747	Intermediate Similarity	NPC470051
0.747	Intermediate Similarity	NPC474778
0.747	Intermediate Similarity	NPC145879
0.747	Intermediate Similarity	NPC474733
0.747	Intermediate Similarity	NPC31564
0.747	Intermediate Similarity	NPC470050
0.747	Intermediate Similarity	NPC474732
0.747	Intermediate Similarity	NPC51014
0.7468	Intermediate Similarity	NPC192744
0.7468	Intermediate Similarity	NPC201459
0.7467	Intermediate Similarity	NPC304983
0.7465	Intermediate Similarity	NPC473902
0.7439	Intermediate Similarity	NPC194937
0.7439	Intermediate Similarity	NPC476038
0.7439	Intermediate Similarity	NPC237712
0.7439	Intermediate Similarity	NPC144258
0.7439	Intermediate Similarity	NPC87552
0.7439	Intermediate Similarity	NPC473246
0.7436	Intermediate Similarity	NPC66105
0.7429	Intermediate Similarity	NPC475795
0.7424	Intermediate Similarity	NPC288296
0.7424	Intermediate Similarity	NPC53245
0.7407	Intermediate Similarity	NPC100297
0.7407	Intermediate Similarity	NPC328351
0.7407	Intermediate Similarity	NPC133391
0.7407	Intermediate Similarity	NPC469804
0.7407	Intermediate Similarity	NPC240302
0.7407	Intermediate Similarity	NPC327969
0.7407	Intermediate Similarity	NPC469805
0.7407	Intermediate Similarity	NPC151519
0.7407	Intermediate Similarity	NPC321289
0.7397	Intermediate Similarity	NPC193770
0.7397	Intermediate Similarity	NPC475523
0.7386	Intermediate Similarity	NPC476174
0.7381	Intermediate Similarity	NPC475740
0.7381	Intermediate Similarity	NPC58063
0.7381	Intermediate Similarity	NPC317590
0.7381	Intermediate Similarity	NPC136948
0.7381	Intermediate Similarity	NPC90652
0.7381	Intermediate Similarity	NPC96496
0.7375	Intermediate Similarity	NPC267517
0.7368	Intermediate Similarity	NPC52667

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 NPC214770 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	207
0.1-0.2	2382
0.2-0.3	4676
0.3-0.4	1276
0.4-0.5	293
0.5-0.6	162
0.6-0.7	118
0.7-0.8	32
0.8-0.85	2
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8841	High Similarity	NPD4747	Approved
0.8824	High Similarity	NPD3621	Clinical (unspecified phase)
0.8696	High Similarity	NPD4137	Phase 3
0.8571	High Similarity	NPD4691	Approved
0.8472	Intermediate Similarity	NPD5733	Approved
0.8219	Intermediate Similarity	NPD4058	Approved
0.8219	Intermediate Similarity	NPD4687	Approved
0.8194	Intermediate Similarity	NPD5276	Approved
0.7654	Intermediate Similarity	NPD4786	Approved
0.7625	Intermediate Similarity	NPD4223	Phase 3
0.7625	Intermediate Similarity	NPD4221	Approved
0.7561	Intermediate Similarity	NPD5329	Approved
0.747	Intermediate Similarity	NPD6098	Approved
0.7439	Intermediate Similarity	NPD4197	Approved
0.7407	Intermediate Similarity	NPD3667	Approved
0.7294	Intermediate Similarity	NPD5737	Approved
0.7294	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7294	Intermediate Similarity	NPD6672	Approved
0.7262	Intermediate Similarity	NPD6409	Approved
0.7262	Intermediate Similarity	NPD4688	Approved
0.7262	Intermediate Similarity	NPD5205	Approved
0.7262	Intermediate Similarity	NPD6684	Approved
0.7262	Intermediate Similarity	NPD4138	Approved
0.7262	Intermediate Similarity	NPD4693	Phase 3
0.7262	Intermediate Similarity	NPD4690	Approved
0.7262	Intermediate Similarity	NPD5330	Approved
0.7262	Intermediate Similarity	NPD7334	Approved
0.7262	Intermediate Similarity	NPD4689	Approved
0.7262	Intermediate Similarity	NPD7146	Approved
0.7262	Intermediate Similarity	NPD7521	Approved
0.7229	Intermediate Similarity	NPD3665	Phase 1
0.7229	Intermediate Similarity	NPD3668	Phase 3
0.7229	Intermediate Similarity	NPD3133	Approved
0.7229	Intermediate Similarity	NPD3666	Approved
0.7209	Intermediate Similarity	NPD6904	Approved
0.7209	Intermediate Similarity	NPD6673	Approved
0.7209	Intermediate Similarity	NPD6080	Approved
0.7209	Intermediate Similarity	NPD5328	Approved
0.7191	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD3617	Approved
0.7108	Intermediate Similarity	NPD4788	Approved
0.7108	Intermediate Similarity	NPD3527	Clinical (unspecified phase)
0.7093	Intermediate Similarity	NPD5208	Approved
0.7093	Intermediate Similarity	NPD6903	Approved
0.7079	Intermediate Similarity	NPD6001	Approved
0.7073	Intermediate Similarity	NPD8028	Phase 2
0.7059	Intermediate Similarity	NPD3618	Phase 1
0.7059	Intermediate Similarity	NPD4694	Approved
0.7059	Intermediate Similarity	NPD5690	Phase 2
0.7059	Intermediate Similarity	NPD5280	Approved
0.7045	Intermediate Similarity	NPD6079	Approved
0.7013	Intermediate Similarity	NPD4243	Approved
0.7011	Intermediate Similarity	NPD4753	Phase 2
0.7	Intermediate Similarity	NPD287	Approved
0.6966	Remote Similarity	NPD6399	Phase 3
0.6867	Remote Similarity	NPD4139	Approved
0.6867	Remote Similarity	NPD4692	Approved
0.686	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.686	Remote Similarity	NPD5279	Phase 3
0.6854	Remote Similarity	NPD6050	Approved
0.6854	Remote Similarity	NPD5693	Phase 1
0.6835	Remote Similarity	NPD4785	Approved
0.6835	Remote Similarity	NPD4784	Approved
0.6829	Remote Similarity	NPD4195	Approved
0.6778	Remote Similarity	NPD5133	Approved
0.6778	Remote Similarity	NPD4202	Approved
0.675	Remote Similarity	NPD7339	Approved
0.675	Remote Similarity	NPD6942	Approved
0.6747	Remote Similarity	NPD4695	Discontinued
0.6744	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6742	Remote Similarity	NPD5207	Approved
0.6742	Remote Similarity	NPD5692	Phase 3
0.6667	Remote Similarity	NPD4623	Approved
0.6667	Remote Similarity	NPD6083	Phase 2
0.6667	Remote Similarity	NPD6084	Phase 2
0.6667	Remote Similarity	NPD5281	Approved
0.6667	Remote Similarity	NPD4519	Discontinued
0.6667	Remote Similarity	NPD5694	Approved
0.6667	Remote Similarity	NPD5284	Approved
0.663	Remote Similarity	NPD4629	Approved
0.663	Remote Similarity	NPD5210	Approved
0.6623	Remote Similarity	NPD5360	Phase 3
0.6623	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.6559	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6559	Remote Similarity	NPD5222	Approved
0.6559	Remote Similarity	NPD4697	Phase 3
0.6559	Remote Similarity	NPD5221	Approved
0.6556	Remote Similarity	NPD4096	Approved
0.6548	Remote Similarity	NPD7525	Registered
0.6543	Remote Similarity	NPD4190	Phase 3
0.6543	Remote Similarity	NPD5275	Approved
0.6538	Remote Similarity	NPD6923	Approved
0.6538	Remote Similarity	NPD6922	Approved
0.6522	Remote Similarity	NPD5769	Clinical (unspecified phase)
0.6489	Remote Similarity	NPD5173	Approved
0.6489	Remote Similarity	NPD4755	Approved
0.6489	Remote Similarity	NPD5959	Approved
0.6484	Remote Similarity	NPD7515	Phase 2
0.6456	Remote Similarity	NPD7143	Approved
0.6456	Remote Similarity	NPD4789	Approved
0.6456	Remote Similarity	NPD7144	Approved
0.6456	Remote Similarity	NPD6938	Clinical (unspecified phase)
0.6456	Remote Similarity	NPD6939	Phase 2
0.6452	Remote Similarity	NPD5695	Phase 3
0.6444	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6421	Remote Similarity	NPD5696	Approved
0.6404	Remote Similarity	NPD3573	Approved
0.6375	Remote Similarity	NPD7150	Approved
0.6375	Remote Similarity	NPD6081	Approved
0.6375	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6375	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6375	Remote Similarity	NPD7152	Approved
0.6375	Remote Similarity	NPD7151	Approved
0.6364	Remote Similarity	NPD4224	Phase 2
0.6354	Remote Similarity	NPD4700	Approved
0.6354	Remote Similarity	NPD5286	Approved
0.6354	Remote Similarity	NPD5285	Approved
0.6354	Remote Similarity	NPD4696	Approved
0.6344	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6344	Remote Similarity	NPD7748	Approved
0.6344	Remote Similarity	NPD7900	Approved
0.6333	Remote Similarity	NPD4518	Approved
0.6327	Remote Similarity	NPD6052	Approved
0.631	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6304	Remote Similarity	NPD8034	Phase 2
0.6304	Remote Similarity	NPD8035	Phase 2
0.6289	Remote Similarity	NPD5223	Approved
0.6277	Remote Similarity	NPD5654	Approved
0.6265	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.625	Remote Similarity	NPD4244	Approved
0.625	Remote Similarity	NPD4245	Approved
0.6234	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.6224	Remote Similarity	NPD5224	Approved
0.6224	Remote Similarity	NPD5226	Approved
0.6224	Remote Similarity	NPD5211	Phase 2
0.6224	Remote Similarity	NPD5225	Approved
0.6224	Remote Similarity	NPD5091	Approved
0.6224	Remote Similarity	NPD4633	Approved
0.622	Remote Similarity	NPD6924	Approved
0.622	Remote Similarity	NPD6926	Approved
0.6207	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.62	Remote Similarity	NPD6008	Approved
0.62	Remote Similarity	NPD5739	Approved
0.62	Remote Similarity	NPD6402	Approved
0.62	Remote Similarity	NPD7128	Approved
0.62	Remote Similarity	NPD6675	Approved
0.6173	Remote Similarity	NPD4758	Discontinued
0.6173	Remote Similarity	NPD5777	Approved
0.6162	Remote Similarity	NPD5175	Approved
0.6162	Remote Similarity	NPD5174	Approved
0.6162	Remote Similarity	NPD4754	Approved
0.6146	Remote Similarity	NPD7902	Approved
0.6139	Remote Similarity	NPD6614	Approved
0.6125	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6125	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6125	Remote Similarity	NPD3698	Phase 2
0.6119	Remote Similarity	NPD345	Approved
0.6119	Remote Similarity	NPD344	Approved
0.6119	Remote Similarity	NPD343	Approved
0.61	Remote Similarity	NPD5141	Approved
0.6092	Remote Similarity	NPD6902	Approved
0.6087	Remote Similarity	NPD6051	Approved
0.6082	Remote Similarity	NPD7638	Approved
0.6078	Remote Similarity	NPD6899	Approved
0.6078	Remote Similarity	NPD7320	Approved
0.6078	Remote Similarity	NPD6881	Approved
0.6071	Remote Similarity	NPD6933	Approved
0.6042	Remote Similarity	NPD7614	Phase 1
0.6042	Remote Similarity	NPD7732	Phase 3
0.604	Remote Similarity	NPD4767	Approved
0.604	Remote Similarity	NPD4768	Approved
0.6024	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.602	Remote Similarity	NPD7639	Approved
0.602	Remote Similarity	NPD6404	Discontinued
0.602	Remote Similarity	NPD7640	Approved
0.6019	Remote Similarity	NPD6372	Approved
0.6019	Remote Similarity	NPD6373	Approved
0.6	Remote Similarity	NPD6925	Approved
0.6	Remote Similarity	NPD6932	Approved
0.6	Remote Similarity	NPD5776	Phase 2
0.598	Remote Similarity	NPD6412	Phase 2
0.598	Remote Similarity	NPD5701	Approved
0.598	Remote Similarity	NPD5697	Approved
0.5962	Remote Similarity	NPD7102	Approved
0.5962	Remote Similarity	NPD7290	Approved
0.5962	Remote Similarity	NPD6883	Approved
0.5949	Remote Similarity	NPD7331	Phase 2
0.593	Remote Similarity	NPD7145	Approved
0.593	Remote Similarity	NPD5364	Discontinued
0.5922	Remote Similarity	NPD6011	Approved
0.5922	Remote Similarity	NPD4729	Approved
0.5922	Remote Similarity	NPD4730	Approved
0.5922	Remote Similarity	NPD5168	Approved
0.5922	Remote Similarity	NPD5128	Approved
0.5905	Remote Similarity	NPD6650	Approved
0.5905	Remote Similarity	NPD6617	Approved
0.5905	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5905	Remote Similarity	NPD6869	Approved
0.5905	Remote Similarity	NPD6847	Approved
0.5905	Remote Similarity	NPD8130	Phase 1

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