NPASS Compound

Structure

CID44260 OpenBabel06191715372D 45 48 0 0 1 0 0 0 0 0999 V2000 3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 3.5000 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 2.5981 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 0.5000 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 4.3301 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 0.5000 0.0000 C 0 0 0 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 -2.5981 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 5.0000 0.0000 C 0 0 0 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 -1.7321 -1.0000 0.0000 C 0 0 1 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 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.1962 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 5.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 5.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 2.0000 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 -0.8660 -2.5000 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 1.7321 -4.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -1.0000 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 0.0000 -0.0000 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 -0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 8 2 0 0 0 0 1 11 1 0 0 0 0 2 8 1 0 0 0 0 2 12 2 0 0 0 0 3 9 2 0 0 0 0 3 13 1 0 0 0 0 4 9 1 0 0 0 0 4 14 2 0 0 0 0 5 10 2 0 0 0 0 5 15 1 0 0 0 0 6 10 1 0 0 0 0 6 16 2 0 0 0 0 7 42 1 0 0 0 0 8 24 1 0 0 0 0 9 25 1 0 0 0 0 10 26 1 0 0 0 0 11 18 2 0 0 0 0 11 28 1 0 0 0 0 12 18 1 0 0 0 0 12 29 1 0 0 0 0 13 19 2 0 0 0 0 13 30 1 0 0 0 0 14 19 1 0 0 0 0 14 31 1 0 0 0 0 15 20 2 0 0 0 0 15 32 1 0 0 0 0 16 20 1 0 0 0 0 16 33 1 0 0 0 0 17 7 1 6 0 0 0 17 21 1 0 0 0 0 17 43 1 0 0 0 0 18 34 1 0 0 0 0 19 35 1 0 0 0 0 20 36 1 0 0 0 0 21 22 1 0 0 0 0 21 37 1 1 0 0 0 22 23 1 0 0 0 0 22 38 1 6 0 0 0 23 27 1 0 0 0 0 23 44 1 1 0 0 0 24 39 2 0 0 0 0 24 42 1 0 0 0 0 25 40 2 0 0 0 0 25 44 1 0 0 0 0 26 41 2 0 0 0 0 26 45 1 0 0 0 0 27 43 1 0 0 0 0 27 45 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	636.1
Volume:	567.909
LogP:	1.217
LogD:	0.517
LogS:	-2.638
# Rotatable Bonds:	10
TPSA:	310.66
# H-Bond Aceptor:	18
# H-Bond Donor:	11
# Rings:	4
# Heavy Atoms:	18

MedChem Properties

QED Drug-Likeness Score:	0.09
Synthetic Accessibility Score:	4.311
Fsp3:	0.222
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.953
MDCK Permeability:	1.311219239141792e-05
Pgp-inhibitor:	0.037
Pgp-substrate:	0.004
Human Intestinal Absorption (HIA):	0.95
20% Bioavailability (F20%):	0.992
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.024
Plasma Protein Binding (PPB):	85.72900390625%
Volume Distribution (VD):	0.487
Pgp-substrate:	18.6990909576416%

ADMET: Metabolism

CYP1A2-inhibitor:	0.5
CYP1A2-substrate:	0.011
CYP2C19-inhibitor:	0.015
CYP2C19-substrate:	0.023
CYP2C9-inhibitor:	0.417
CYP2C9-substrate:	0.031
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.088
CYP3A4-inhibitor:	0.038
CYP3A4-substrate:	0.003

ADMET: Excretion

Clearance (CL):	12.374
Half-life (T1/2):	0.978

ADMET: Toxicity

hERG Blockers:	0.389
Human Hepatotoxicity (H-HT):	0.081
Drug-inuced Liver Injury (DILI):	0.948
AMES Toxicity:	0.083
Rat Oral Acute Toxicity:	0.0
Maximum Recommended Daily Dose:	0.003
Skin Sensitization:	0.966
Carcinogencity:	0.021
Eye Corrosion:	0.003
Eye Irritation:	0.937
Respiratory Toxicity:	0.003

Download Data

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

Natural Product: NPC44260

Natural Product ID:	NPC44260
*Common Name:**	1,2,6-Tri-O-Galloyl-Beta-D-Glucose
IUPAC Name:	[(2R,3S,4S,5R,6S)-3,4-dihydroxy-5,6-bis[(3,4,5-trihydroxybenzoyl)oxy]oxan-2-yl]methyl 3,4,5-trihydroxybenzoate
Synonyms:
Standard InCHIKey:	LLENXGNWVNSBQG-VFTFQOQOSA-N
Standard InCHI:	InChI=1S/C27H24O18/c28-11-1-8(2-12(29)18(11)34)24(39)42-7-17-21(37)22(38)23(44-25(40)9-3-13(30)19(35)14(31)4-9)27(43-17)45-26(41)10-5-15(32)20(36)16(33)6-10/h1-6,17,21-23,27-38H,7H2/t17-,21-,22+,23-,27+/m1/s1
SMILES:	c1c(cc(c(c1O)O)O)C(=O)OC[C@@H]1[C@H]([C@@H]([C@H]([C@@H](O1)OC(=O)c1cc(c(c(c1)O)O)O)OC(=O)c1cc(c(c(c1)O)O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL447974
PubChem CID:	440308
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000238] Tannins

*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
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	n.a.	fruit	n.a.	DOI[10.1007/s00217-007-0799-1]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	n.a.	flower	n.a.	DOI[10.1016/j.foodchem.2011.01.077]
NPO21244	Delphinium nuttallianum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10978210]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11520216]
NPO20652	Phytolacca acinosa	Species	Phytolaccaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12932140]
NPO18674	Juglans regia	Species	Juglandaceae	Eukaryota	n.a.	root	n.a.	PMID[14727919]
NPO18674	Juglans regia	Species	Juglandaceae	Eukaryota	n.a.	bark	n.a.	PMID[14727919]
NPO18674	Juglans regia	Species	Juglandaceae	Eukaryota	n.a.	xylem	n.a.	PMID[14727919]
NPO18674	Juglans regia	Species	Juglandaceae	Eukaryota	n.a.	leaf	n.a.	PMID[14727919]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	Seeds	n.a.	n.a.	PMID[15620261]
NPO20779	Garcinia hombroniana	Species	Clusiaceae	Eukaryota	leaves	n.a.	n.a.	PMID[16124765]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	root	n.a.	PMID[16441081]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16675659]
NPO18674	Juglans regia	Species	Juglandaceae	Eukaryota	n.a.	pericarp	n.a.	PMID[18496782]
NPO27524	Eugenia hyemalis	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18763827]
NPO27524	Eugenia hyemalis	Species	Myrtaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[18763827]
NPO21244	Delphinium nuttallianum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19012276]
NPO12088	Conyza canadensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20121251]
NPO20842	Beauveria felina	Species	Cordycipitaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21438588]
NPO20146	Cladiella krempfi	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[21861494]
NPO20096	Cirsium japonicum	Species	Asteraceae	Eukaryota	n.a.	whole plant	n.a.	PMID[21899269]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22074222]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	root	n.a.	PMID[22074222]
NPO12088	Conyza canadensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22612410]
NPO20842	Beauveria felina	Species	Cordycipitaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23822585]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	root	n.a.	PMID[23867078]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	rhizome	n.a.	PMID[23867078]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24479468]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	roots	n.a.	n.a.	PMID[24957203]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25445757]
NPO18674	Juglans regia	Species	Juglandaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25466114]
NPO19996	Caulerpa peltata	Species	Caulerpaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25593390]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25744461]
NPO20842	Beauveria felina	Species	Cordycipitaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26295595]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26841168]
NPO18674	Juglans regia	Species	Juglandaceae	Eukaryota	Flowers	n.a.	n.a.	PMID[28737396]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32196343]
NPO22052	Aspergillus candidus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[5391291]
NPO12148.2	Acer pictum subsp. okamotoanum	Subspecies	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9461665]
NPO18674	Juglans regia	Species	Juglandaceae	Eukaryota	n.a.	leaf	n.a.	Database[Article]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	Pericarp	n.a.	n.a.	Database[FooDB]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	Root Bark	n.a.	n.a.	Database[FooDB]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO18674	Juglans regia	Species	Juglandaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	Stem Bark	n.a.	n.a.	Database[FooDB]
NPO18674	Juglans regia	Species	Juglandaceae	Eukaryota	Stem Bark	n.a.	n.a.	Database[FooDB]
NPO18674	Juglans regia	Species	Juglandaceae	Eukaryota	Testa	n.a.	n.a.	Database[FooDB]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	Twig	n.a.	n.a.	Database[FooDB]
NPO18674	Juglans regia	Species	Juglandaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO17336	Benincasa hispida	Species	Cucurbitaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	Bark	n.a.	n.a.	Database[FooDB]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO18674	Juglans regia	Species	Juglandaceae	Eukaryota	Embryo	n.a.	n.a.	Database[FooDB]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO17336	Benincasa hispida	Species	Cucurbitaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO18674	Juglans regia	Species	Juglandaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO18674	Juglans regia	Species	Juglandaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO5731	Euphorbia humifusa	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26917	Quercus rubra	Species	Fagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO20096	Cirsium japonicum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22976	Ruta microcarpa	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21096	Cardiospermum halicacabum	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12088	Conyza canadensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO20881	Rheum officinale	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO20144	Lespedeza tomentosa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19095	Strophanthus preussii	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO16414	Thuja plicata	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO20490	Erythrophleum ivorense	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17336	Benincasa hispida	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18674	Juglans regia	Species	Juglandaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	Fruits	n.a.		Database[Phenol-Explorer]
NPO2228	Photinia serratifolia	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18674	Juglans regia	Species	Juglandaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21096	Cardiospermum halicacabum	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29466	Triglochin maritima	Species	Juncaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16414	Thuja plicata	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13754	Tanacetum coccineum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20881	Rheum officinale	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20490	Erythrophleum ivorense	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26917	Quercus rubra	Species	Fagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22121	Piper arboreum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17018	Salvia greggii	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22976	Ruta microcarpa	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5731	Euphorbia humifusa	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6395	Phedimus kamtschaticus	Species	Crassulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21691	Dillenia indica	Species	Dilleniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20144	Lespedeza tomentosa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12088	Conyza canadensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20652	Phytolacca acinosa	Species	Phytolaccaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20096	Cirsium japonicum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19095	Strophanthus preussii	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17336	Benincasa hispida	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO20881	Rheum officinale	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO20490	Erythrophleum ivorense	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO20096	Cirsium japonicum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO22976	Ruta microcarpa	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO18674	Juglans regia	Species	Juglandaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO20652	Phytolacca acinosa	Species	Phytolaccaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO12088	Conyza canadensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO17336	Benincasa hispida	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO21096	Cardiospermum halicacabum	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO20096	Cirsium japonicum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO18674	Juglans regia	Species	Juglandaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO20652	Phytolacca acinosa	Species	Phytolaccaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO20881	Rheum officinale	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO5731	Euphorbia humifusa	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO17336	Benincasa hispida	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO28912	Astragalus gummifer	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO22250	Parastrephia lepidophylla	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18680	Larix decidua	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19818	Jacquemontia paniculata	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26917	Quercus rubra	Species	Fagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23010	Crinum defixum	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12362	Coreopsis fasciculata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13454	Amphorogyne spicata	Species	Amphorogynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12148.2	Acer pictum subsp. okamotoanum	Subspecies	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19512	Gleichenia quadripartita	Species	Gleicheniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2922	Botryosphaeria berengeriana	Species	Botryosphaeriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22829	Ozoroa insignis	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17856	Anaphalis lactea	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16572	Rhododendron dahuricum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17018	Salvia greggii	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20947	Tagetes filifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17336	Benincasa hispida	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21096	Cardiospermum halicacabum	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22893	Apterostigma dentigerum	Species	Formicidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18144	Metrodorea nigra	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13823	Hypericum mysorense	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22121	Piper arboreum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19899	Crepis foetida	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21112	Chaetomium carinthiacum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20332	Dioscoreophyllum cumminsii	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19996	Caulerpa peltata	Species	Caulerpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19395	Nepeta granatensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20625	Delphinium virgatum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22568	Aristolochia elegans	Species	Aristolochiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20844	Sphaerella rosigena	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO20972	Oscillatoria princeps	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO14932.1	Dalbergia lanceolaria subsp. paniculata	Subspecies	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18537	Leontopodium nanum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20223	Rosa pomifera	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20779	Garcinia hombroniana	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12108	Aizopsis selskiana	Species	Crassulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22381	Euphorbia segetalis	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21564	Senecio behnii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6395	Phedimus kamtschaticus	Species	Crassulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21376	Lupinus corymbosus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20490	Erythrophleum ivorense	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20652	Phytolacca acinosa	Species	Phytolaccaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19095	Strophanthus preussii	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22976	Ruta microcarpa	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13355	Selinum carvifolium	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2228	Photinia serratifolia	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21691	Dillenia indica	Species	Dilleniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21227	Aglaia elaeagnoidea	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17568	Balanophora laxiflora	Species	Balanophoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20881	Rheum officinale	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22763	Cuphea carthagenensis	Species	Lythraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20753	Grangea maderaspatana	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7786	Lentinus tigrinus	Species	Lentinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5731	Euphorbia humifusa	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20209	Dorstenia lindeniana	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19232	Anchusa azurea	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10216	Leptocereus quadricostatus	Species	Cactaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20353	Degenia velebitica	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20560	Polyporus betulinus	Species	Polyporaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16142	Verbascum thapsiforme	Species	Scrophulariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18867	Stephanitis takeyai	Species	Tingidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20146	Cladiella krempfi	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19671	Dipsacus azureus	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2780	Brenneria rubrifaciens	Species	Pectobacteriaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO22052	Aspergillus candidus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22447	Sidastrum acuminatum	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18674	Juglans regia	Species	Juglandaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24407	Bipolaris heveae	Species	Pleosporaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22635	Penstemon secundiflorus	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12088	Conyza canadensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21282	Aplidium orthium	Species	Polyclinidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23953	Zanthoxylum monophyllum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14248	Mandragora autumnalis	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21991	Modiolus demissus	Species	Mytilidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21603	Eskemukerjea megacarpum	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO14800	Oophaga granulifera	Species	Dendrobatidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18775	Cratena peregrina	Species	Facelinidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29466	Triglochin maritima	Species	Juncaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10359	Chaiturus marrubiastrum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21859	Centaurea nigrescens	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13246	Pinalia stricta	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20144	Lespedeza tomentosa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22315	Phlogacanthus thyrsiflorus	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21473	Urtica triangularis	Species	Urticaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22675	Helichrysum chionosphaerum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20422	Albizia myriophylla	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10026	Mitracarpus scaber	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27524	Eugenia hyemalis	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28912	Astragalus gummifer	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20096	Cirsium japonicum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19037	Senecio praecox	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20842	Beauveria felina	Species	Cordycipitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13754	Tanacetum coccineum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15422	Carduus tenuiflorus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27737	Penicillium shearii	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17247	Actinoplanes friuliensis	Species	Micromonosporaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO18287	Penicillium bilaiae	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11580	Onobrychis arenaria	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2359	Cynoglossum germanicum	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16414	Thuja plicata	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19521	Inella verrucosa	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO22509	Syncolostemon parviflorus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19913	Rhynchophorus ferrugineus	Species	Curculionidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21730	Pouzolzia occidentalis	Species	Urticaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26393.1	Petunia integrifolia subsp. inflata	Subspecies	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21420	Phormia regina	Species	Calliphoridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21244	Delphinium nuttallianum	Species	Ranunculaceae	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
EC50	1
ED50	5
IC50	8
Others	3

Activity Type	# Activity
Cell Line	4
Individual Protein	4
NON-MOLECULAR	1
Organism	3
Others	4
Protein Family	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT459	Individual Protein	Human immunodeficiency virus type 1 reverse transcriptase	Human immunodeficiency virus 1	Inhibition	=	16.0	%	PMID[469951]
NPT5224	Individual Protein	NS3	Hepatitis C virus	IC50	=	1890.0	nM	PMID[469953]
NPT326	Individual Protein	Squalene monooxygenase	Rattus norvegicus	IC50	=	630.0	nM	PMID[469954]
NPT672	Cell Line	TE-671	Homo sapiens	ED50	>	10.0	ug ml-1	PMID[469955]
NPT180	Cell Line	HCT-8	Homo sapiens	ED50	>	10.0	ug ml-1	PMID[469955]
NPT81	Cell Line	A549	Homo sapiens	ED50	>	10.0	ug ml-1	PMID[469955]
NPT91	Cell Line	KB	Homo sapiens	ED50	>	10.0	ug ml-1	PMID[469955]
NPT12	Individual Protein	Human immunodeficiency virus type 1 integrase	Human immunodeficiency virus 1	IC50	=	28.3	ug.mL-1	PMID[469957]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	IC50	=	19000.0	nM	PMID[469951]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	EC50	=	50000.0	nM	PMID[469951]
NPT27	Others	Unspecified		Therapeutic index	=	0.4	n.a.	PMID[469951]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	Inhibition	=	20.0	%	PMID[469951]
NPT316	Protein Family	Protein kinase C (PKC)	Homo sapiens	IC50	>	100000.0	nM	PMID[469952]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ED50	>	10.0	ug ml-1	PMID[469955]
NPT2	Others	Unspecified		IC50	=	10210.0	nM	PMID[469956]
NPT2	Others	Unspecified		IC50	=	280.0	nM	PMID[469956]
NPT2	Others	Unspecified		IC50	=	550.0	nM	PMID[469956]

☑ 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 NPC44260 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	358
0.1-0.2	1574
0.2-0.3	3814
0.3-0.4	8337
0.4-0.5	9656
0.5-0.6	5193
0.6-0.7	7038
0.7-0.8	5534
0.8-0.85	947
0.85-0.9	165
0.9-0.95	59
0.95-1	22

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC61152
1.0	High Similarity	NPC205037
1.0	High Similarity	NPC16024
1.0	High Similarity	NPC3746
0.9732	High Similarity	NPC172419
0.9732	High Similarity	NPC238419
0.9724	High Similarity	NPC92117
0.9664	High Similarity	NPC247629
0.9664	High Similarity	NPC239019
0.9655	High Similarity	NPC142528
0.9655	High Similarity	NPC248257
0.9655	High Similarity	NPC120621
0.9592	High Similarity	NPC140151
0.9536	High Similarity	NPC114791
0.9536	High Similarity	NPC104222
0.9536	High Similarity	NPC318826
0.9536	High Similarity	NPC210501
0.9536	High Similarity	NPC141331
0.9477	High Similarity	NPC14030
0.9477	High Similarity	NPC291957
0.9474	High Similarity	NPC289346
0.9448	High Similarity	NPC108455
0.9416	High Similarity	NPC470898
0.9379	High Similarity	NPC22176
0.9379	High Similarity	NPC190587
0.9379	High Similarity	NPC121573
0.9379	High Similarity	NPC226738
0.9379	High Similarity	NPC229036
0.9351	High Similarity	NPC90905
0.9351	High Similarity	NPC285108
0.9351	High Similarity	NPC4013
0.9351	High Similarity	NPC33298
0.9324	High Similarity	NPC75945
0.9236	High Similarity	NPC470271
0.9236	High Similarity	NPC311389
0.9216	High Similarity	NPC472860
0.9216	High Similarity	NPC1913
0.92	High Similarity	NPC252979
0.9177	High Similarity	NPC198125
0.9177	High Similarity	NPC197708
0.9177	High Similarity	NPC95421
0.9177	High Similarity	NPC658
0.9172	High Similarity	NPC175793
0.9156	High Similarity	NPC289811
0.9156	High Similarity	NPC74319
0.9156	High Similarity	NPC287872
0.9156	High Similarity	NPC160780
0.9128	High Similarity	NPC43123
0.9119	High Similarity	NPC470272
0.9114	High Similarity	NPC43918
0.9114	High Similarity	NPC261411
0.9114	High Similarity	NPC190204
0.9103	High Similarity	NPC225036
0.9103	High Similarity	NPC75763
0.9103	High Similarity	NPC105525
0.9103	High Similarity	NPC12218
0.9097	High Similarity	NPC119125
0.9097	High Similarity	NPC239966
0.9097	High Similarity	NPC166277
0.9097	High Similarity	NPC203020
0.9091	High Similarity	NPC133984
0.9085	High Similarity	NPC172920
0.9085	High Similarity	NPC156624
0.9085	High Similarity	NPC203757
0.9067	High Similarity	NPC42464
0.9062	High Similarity	NPC102851
0.9062	High Similarity	NPC5786
0.9057	High Similarity	NPC149300
0.9038	High Similarity	NPC472859
0.9038	High Similarity	NPC25389
0.9038	High Similarity	NPC311803
0.9007	High Similarity	NPC306343
0.9	High Similarity	NPC204937
0.9	High Similarity	NPC149011
0.9	High Similarity	NPC47521
0.8994	High Similarity	NPC31034
0.8993	High Similarity	NPC473867
0.8968	High Similarity	NPC135222
0.8968	High Similarity	NPC474010
0.8968	High Similarity	NPC104275
0.8968	High Similarity	NPC4747
0.8954	High Similarity	NPC310661
0.8954	High Similarity	NPC105827
0.8924	High Similarity	NPC121290
0.8904	High Similarity	NPC239943
0.8903	High Similarity	NPC300845
0.8903	High Similarity	NPC250436
0.8903	High Similarity	NPC88803
0.8903	High Similarity	NPC104983
0.8903	High Similarity	NPC134925
0.8903	High Similarity	NPC291948
0.8896	High Similarity	NPC327032
0.8896	High Similarity	NPC191046
0.8896	High Similarity	NPC472723
0.8896	High Similarity	NPC194095
0.8896	High Similarity	NPC297574
0.8889	High Similarity	NPC172033
0.8889	High Similarity	NPC175230
0.8889	High Similarity	NPC88560
0.8867	High Similarity	NPC474465
0.8859	High Similarity	NPC50221
0.8859	High Similarity	NPC114242
0.8854	High Similarity	NPC24164
0.8846	High Similarity	NPC160512
0.8846	High Similarity	NPC289322
0.8846	High Similarity	NPC38779
0.8846	High Similarity	NPC114179
0.8846	High Similarity	NPC156818
0.8846	High Similarity	NPC49173
0.8846	High Similarity	NPC68324
0.8841	High Similarity	NPC293626
0.8841	High Similarity	NPC217387
0.8841	High Similarity	NPC196127
0.8841	High Similarity	NPC253521
0.8841	High Similarity	NPC258044
0.8841	High Similarity	NPC37668
0.8841	High Similarity	NPC113836
0.8841	High Similarity	NPC267680
0.8827	High Similarity	NPC47140
0.8827	High Similarity	NPC67134
0.879	High Similarity	NPC87317
0.8788	High Similarity	NPC198902
0.8788	High Similarity	NPC80956
0.8782	High Similarity	NPC318432
0.8782	High Similarity	NPC471405
0.878	High Similarity	NPC61904
0.878	High Similarity	NPC67629
0.878	High Similarity	NPC144097
0.878	High Similarity	NPC79736
0.878	High Similarity	NPC472991
0.878	High Similarity	NPC472992
0.8773	High Similarity	NPC472993
0.8773	High Similarity	NPC163165
0.8766	High Similarity	NPC134905
0.8766	High Similarity	NPC36130
0.8758	High Similarity	NPC116745
0.8758	High Similarity	NPC473818
0.8742	High Similarity	NPC41009
0.8742	High Similarity	NPC148273
0.8734	High Similarity	NPC53889
0.8727	High Similarity	NPC476620
0.8727	High Similarity	NPC267549
0.8727	High Similarity	NPC476619
0.8727	High Similarity	NPC476621
0.8727	High Similarity	NPC476623
0.8727	High Similarity	NPC35167
0.8727	High Similarity	NPC476622
0.8727	High Similarity	NPC476618
0.8726	High Similarity	NPC187205
0.8726	High Similarity	NPC257309
0.8726	High Similarity	NPC226759
0.872	High Similarity	NPC169645
0.872	High Similarity	NPC223426
0.872	High Similarity	NPC84482
0.872	High Similarity	NPC34267
0.872	High Similarity	NPC214621
0.872	High Similarity	NPC171706
0.872	High Similarity	NPC81042
0.8718	High Similarity	NPC10205
0.8718	High Similarity	NPC145425
0.871	High Similarity	NPC157898
0.8707	High Similarity	NPC310252
0.8707	High Similarity	NPC302583
0.8707	High Similarity	NPC84789
0.8707	High Similarity	NPC100558
0.8704	High Similarity	NPC138927
0.8699	High Similarity	NPC18646
0.8688	High Similarity	NPC168822
0.8688	High Similarity	NPC88043
0.8683	High Similarity	NPC97119
0.8683	High Similarity	NPC135831
0.8683	High Similarity	NPC297503
0.8667	High Similarity	NPC154741
0.8667	High Similarity	NPC296018
0.865	High Similarity	NPC20505
0.865	High Similarity	NPC155763
0.865	High Similarity	NPC235260
0.8645	High Similarity	NPC75695
0.8642	High Similarity	NPC217781
0.8642	High Similarity	NPC45400
0.8639	High Similarity	NPC471345
0.8639	High Similarity	NPC156892
0.8634	High Similarity	NPC165720
0.8634	High Similarity	NPC162169
0.8634	High Similarity	NPC475738
0.8634	High Similarity	NPC166851
0.8634	High Similarity	NPC471788
0.8631	High Similarity	NPC231254
0.8627	High Similarity	NPC473138
0.8627	High Similarity	NPC28776
0.8625	High Similarity	NPC77660
0.8625	High Similarity	NPC473043
0.8625	High Similarity	NPC189142
0.8625	High Similarity	NPC246024
0.8623	High Similarity	NPC469371
0.8623	High Similarity	NPC8940
0.8623	High Similarity	NPC53680
0.8623	High Similarity	NPC208797
0.8616	High Similarity	NPC476373
0.8616	High Similarity	NPC24627

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 NPC44260 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	307
0.1-0.2	874
0.2-0.3	1890
0.3-0.4	2807
0.4-0.5	1922
0.5-0.6	972
0.6-0.7	272
0.7-0.8	91
0.8-0.85	13
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8903	High Similarity	NPD4868	Clinical (unspecified phase)
0.8562	High Similarity	NPD230	Phase 1
0.8543	High Similarity	NPD6190	Approved
0.8494	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8485	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8424	Intermediate Similarity	NPD7472	Approved
0.8415	Intermediate Similarity	NPD3818	Discontinued
0.84	Intermediate Similarity	NPD7266	Discontinued
0.8373	Intermediate Similarity	NPD6797	Phase 2
0.8364	Intermediate Similarity	NPD7054	Approved
0.8323	Intermediate Similarity	NPD7251	Discontinued
0.8313	Intermediate Similarity	NPD7074	Phase 3
0.8261	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8214	Intermediate Similarity	NPD7685	Pre-registration
0.8166	Intermediate Similarity	NPD7808	Phase 3
0.8153	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.8084	Intermediate Similarity	NPD7228	Approved
0.8072	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8072	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8072	Intermediate Similarity	NPD6166	Phase 2
0.7988	Intermediate Similarity	NPD6234	Discontinued
0.7987	Intermediate Similarity	NPD1653	Approved
0.7963	Intermediate Similarity	NPD1465	Phase 2
0.7931	Intermediate Similarity	NPD9269	Phase 2
0.7929	Intermediate Similarity	NPD5844	Phase 1
0.7901	Intermediate Similarity	NPD37	Approved
0.7901	Intermediate Similarity	NPD1934	Approved
0.7888	Intermediate Similarity	NPD4380	Phase 2
0.7866	Intermediate Similarity	NPD4967	Phase 2
0.7866	Intermediate Similarity	NPD4965	Approved
0.7866	Intermediate Similarity	NPD4966	Approved
0.7853	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7848	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7791	Intermediate Similarity	NPD6559	Discontinued
0.7744	Intermediate Similarity	NPD2801	Approved
0.7738	Intermediate Similarity	NPD6232	Discontinued
0.7719	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7714	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD3817	Phase 2
0.7688	Intermediate Similarity	NPD7240	Approved
0.7679	Intermediate Similarity	NPD7199	Phase 2
0.7655	Intermediate Similarity	NPD9268	Approved
0.7651	Intermediate Similarity	NPD3882	Suspended
0.7625	Intermediate Similarity	NPD1511	Approved
0.7605	Intermediate Similarity	NPD7075	Discontinued
0.7602	Intermediate Similarity	NPD7473	Discontinued
0.76	Intermediate Similarity	NPD8313	Approved
0.76	Intermediate Similarity	NPD8312	Approved
0.7598	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.759	Intermediate Similarity	NPD5402	Approved
0.7553	Intermediate Similarity	NPD8151	Discontinued
0.7532	Intermediate Similarity	NPD943	Approved
0.7531	Intermediate Similarity	NPD1512	Approved
0.753	Intermediate Similarity	NPD8455	Phase 2
0.7515	Intermediate Similarity	NPD7411	Suspended
0.7486	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7438	Intermediate Similarity	NPD4628	Phase 3
0.7425	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7403	Intermediate Similarity	NPD3764	Approved
0.7381	Intermediate Similarity	NPD5353	Approved
0.7378	Intermediate Similarity	NPD5403	Approved
0.7365	Intermediate Similarity	NPD6801	Discontinued
0.7356	Intermediate Similarity	NPD3751	Discontinued
0.7347	Intermediate Similarity	NPD9545	Approved
0.7338	Intermediate Similarity	NPD3027	Phase 3
0.7321	Intermediate Similarity	NPD7819	Suspended
0.7312	Intermediate Similarity	NPD1549	Phase 2
0.731	Intermediate Similarity	NPD5494	Approved
0.7308	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD1613	Approved
0.7301	Intermediate Similarity	NPD6799	Approved
0.7278	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD6959	Discontinued
0.7258	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7256	Intermediate Similarity	NPD5401	Approved
0.725	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7233	Intermediate Similarity	NPD1510	Phase 2
0.7228	Intermediate Similarity	NPD6535	Approved
0.7228	Intermediate Similarity	NPD6534	Approved
0.7225	Intermediate Similarity	NPD3787	Discontinued
0.7222	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD3750	Approved
0.7208	Intermediate Similarity	NPD9494	Approved
0.7205	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7196	Intermediate Similarity	NPD7680	Approved
0.7196	Intermediate Similarity	NPD7435	Discontinued
0.7193	Intermediate Similarity	NPD3749	Approved
0.7186	Intermediate Similarity	NPD3455	Phase 2
0.7182	Intermediate Similarity	NPD8150	Discontinued
0.716	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7158	Intermediate Similarity	NPD8320	Phase 1
0.7158	Intermediate Similarity	NPD8319	Approved
0.7152	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD7768	Phase 2
0.7128	Intermediate Similarity	NPD6778	Approved
0.7128	Intermediate Similarity	NPD6780	Approved
0.7128	Intermediate Similarity	NPD6776	Approved
0.7128	Intermediate Similarity	NPD6782	Approved
0.7128	Intermediate Similarity	NPD6781	Approved
0.7128	Intermediate Similarity	NPD6777	Approved
0.7128	Intermediate Similarity	NPD6779	Approved
0.7125	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD8166	Discontinued
0.7112	Intermediate Similarity	NPD7699	Phase 2
0.7112	Intermediate Similarity	NPD7700	Phase 2
0.7097	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD5242	Approved
0.7083	Intermediate Similarity	NPD7458	Discontinued
0.7081	Intermediate Similarity	NPD1551	Phase 2
0.7072	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.707	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD2532	Approved
0.7048	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD2534	Approved
0.7048	Intermediate Similarity	NPD2533	Approved
0.7044	Intermediate Similarity	NPD1933	Approved
0.7041	Intermediate Similarity	NPD6599	Discontinued
0.7026	Intermediate Similarity	NPD7783	Phase 2
0.7026	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6385	Approved
0.7	Intermediate Similarity	NPD6386	Approved
0.6989	Remote Similarity	NPD6212	Phase 3
0.6989	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD6213	Phase 3
0.6988	Remote Similarity	NPD7390	Discontinued
0.6982	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD1240	Approved
0.6979	Remote Similarity	NPD7871	Phase 2
0.6979	Remote Similarity	NPD7870	Phase 2
0.6975	Remote Similarity	NPD2935	Discontinued
0.6975	Remote Similarity	NPD2796	Approved
0.6974	Remote Similarity	NPD7874	Approved
0.6974	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD7585	Approved
0.6948	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD447	Suspended
0.6927	Remote Similarity	NPD7698	Approved
0.6927	Remote Similarity	NPD7697	Approved
0.6927	Remote Similarity	NPD7696	Phase 3
0.6918	Remote Similarity	NPD6233	Phase 2
0.6914	Remote Similarity	NPD3748	Approved
0.6914	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6907	Remote Similarity	NPD7583	Approved
0.6906	Remote Similarity	NPD7039	Approved
0.6906	Remote Similarity	NPD7038	Approved
0.6894	Remote Similarity	NPD1607	Approved
0.6875	Remote Similarity	NPD6823	Phase 2
0.6872	Remote Similarity	NPD7701	Phase 2
0.6871	Remote Similarity	NPD5406	Approved
0.6871	Remote Similarity	NPD5404	Approved
0.6871	Remote Similarity	NPD5408	Approved
0.6871	Remote Similarity	NPD5405	Approved
0.6852	Remote Similarity	NPD4978	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD7584	Approved
0.6818	Remote Similarity	NPD1091	Approved
0.6811	Remote Similarity	NPD8434	Phase 2
0.6807	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6798	Remote Similarity	NPD3926	Phase 2
0.6789	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.678	Remote Similarity	NPD8127	Discontinued
0.6768	Remote Similarity	NPD7801	Approved
0.6761	Remote Similarity	NPD919	Approved
0.675	Remote Similarity	NPD6798	Discontinued
0.6747	Remote Similarity	NPD6674	Discontinued
0.673	Remote Similarity	NPD4908	Phase 1
0.6716	Remote Similarity	NPD8155	Clinical (unspecified phase)
0.6712	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6706	Remote Similarity	NPD6273	Approved
0.6705	Remote Similarity	NPD6971	Discontinued
0.6687	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD4357	Discontinued
0.6686	Remote Similarity	NPD3226	Approved
0.6684	Remote Similarity	NPD7211	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5953	Discontinued
0.6648	Remote Similarity	NPD5711	Approved
0.6648	Remote Similarity	NPD7229	Phase 3
0.6648	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.6648	Remote Similarity	NPD5710	Approved
0.6647	Remote Similarity	NPD1652	Phase 2
0.6646	Remote Similarity	NPD7097	Phase 1
0.6646	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD1203	Approved
0.6645	Remote Similarity	NPD9493	Approved
0.6627	Remote Similarity	NPD7440	Discontinued
0.6609	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6595	Remote Similarity	NPD7549	Discontinued
0.6593	Remote Similarity	NPD7799	Discontinued
0.6592	Remote Similarity	NPD1247	Approved
0.6582	Remote Similarity	NPD3225	Approved
0.657	Remote Similarity	NPD920	Approved
0.6566	Remote Similarity	NPD6099	Approved
0.6566	Remote Similarity	NPD6100	Approved
0.6564	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6561	Remote Similarity	NPD1608	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