NPASS Compound

Structure

CID271138 OpenBabel06191716072D 47 52 0 0 1 0 0 0 0 0999 V2000 2.5491 4.4151 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6994 0.9811 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0396 -2.3214 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8497 -1.4717 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8497 -0.4906 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2088 3.7931 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.9623 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8497 1.4717 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3987 2.9434 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8497 -1.4717 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.9811 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3987 1.9623 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6994 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5491 0.4906 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5491 0.4906 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6472 1.4717 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0585 -2.3214 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5491 3.4340 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8497 1.4717 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3987 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 6.7975 0.9811 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6994 -0.9811 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8497 0.4906 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 6.7975 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.9478 -0.4906 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.0981 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6994 1.9623 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.3987 -0.9811 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.0981 0.9811 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.3987 0.9811 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6994 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5491 -1.4717 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8497 0.4906 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6994 2.9434 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5491 1.4717 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 8.4969 0.9811 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5491 -3.1711 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2484 0.4906 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.6472 -0.4906 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.9478 -1.4717 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2484 -0.4906 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2484 -1.4717 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3987 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7182 2.9434 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.9478 1.4717 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2484 1.4717 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 18 1 0 0 0 0 4 33 1 0 0 0 0 7 8 1 0 0 0 0 7 19 2 0 0 0 0 8 23 1 0 0 0 0 9 12 1 0 0 0 0 9 18 1 0 0 0 0 10 11 1 0 0 0 0 10 22 1 0 0 0 0 11 34 1 0 0 0 0 12 36 1 0 0 0 0 13 14 1 0 0 0 0 13 33 1 0 0 0 0 14 36 1 0 0 0 0 15 20 1 0 0 0 0 15 31 1 0 0 0 0 16 37 1 0 0 0 0 17 32 1 0 0 0 0 17 38 1 0 0 0 0 18 35 1 6 0 0 0 19 27 1 0 0 0 0 19 33 1 0 0 0 0 20 28 1 0 0 0 0 20 39 1 6 0 0 0 21 16 1 6 0 0 0 21 24 1 0 0 0 0 21 46 1 0 0 0 0 22 31 1 1 0 0 0 22 32 1 0 0 0 0 23 31 1 1 0 0 0 23 34 1 0 0 0 0 24 25 1 0 0 0 0 24 40 1 1 0 0 0 25 26 1 0 0 0 0 25 41 1 6 0 0 0 26 29 1 0 0 0 0 26 42 1 1 0 0 0 27 35 1 6 0 0 0 27 36 1 0 0 0 0 28 32 1 1 0 0 0 28 43 1 0 0 0 0 29 46 1 0 0 0 0 29 47 1 6 0 0 0 30 44 2 0 0 0 0 30 47 1 0 0 0 0 31 2 1 1 0 0 0 32 3 1 1 0 0 0 33 34 1 1 0 0 0 34 5 1 1 0 0 0 35 6 1 1 0 0 0 35 45 1 0 0 0 0 36 30 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	666.4
Volume:	671.293
LogP:	2.317
LogD:	1.69
LogS:	-3.479
# Rotatable Bonds:	5
TPSA:	197.37
# H-Bond Aceptor:	11
# H-Bond Donor:	8
# Rings:	6
# Heavy Atoms:	11

MedChem Properties

QED Drug-Likeness Score:	0.16
Synthetic Accessibility Score:	5.655
Fsp3:	0.917
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.752
MDCK Permeability:	2.192087958974298e-05
Pgp-inhibitor:	0.091
Pgp-substrate:	0.016
Human Intestinal Absorption (HIA):	0.601
20% Bioavailability (F20%):	0.61
30% Bioavailability (F30%):	0.969

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.022
Plasma Protein Binding (PPB):	84.16815185546875%
Volume Distribution (VD):	0.397
Pgp-substrate:	9.425529479980469%

ADMET: Metabolism

CYP1A2-inhibitor:	0.006
CYP1A2-substrate:	0.636
CYP2C19-inhibitor:	0.001
CYP2C19-substrate:	0.68
CYP2C9-inhibitor:	0.002
CYP2C9-substrate:	0.034
CYP2D6-inhibitor:	0.001
CYP2D6-substrate:	0.061
CYP3A4-inhibitor:	0.318
CYP3A4-substrate:	0.081

ADMET: Excretion

Clearance (CL):	1.215
Half-life (T1/2):	0.622

ADMET: Toxicity

hERG Blockers:	0.034
Human Hepatotoxicity (H-HT):	0.197
Drug-inuced Liver Injury (DILI):	0.029
AMES Toxicity:	0.051
Rat Oral Acute Toxicity:	0.194
Maximum Recommended Daily Dose:	0.771
Skin Sensitization:	0.076
Carcinogencity:	0.011
Eye Corrosion:	0.003
Eye Irritation:	0.012
Respiratory Toxicity:	0.965

Download Data

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

Natural Product: NPC271138

Natural Product ID:	NPC271138
*Common Name:**	Nigaichigoside F1
IUPAC Name:	[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] (1R,2R,4aS,6aR,6aS,6bR,8aR,9R,10R,11R,12aR,14bS)-1,10,11-trihydroxy-9-(hydroxymethyl)-1,2,6a,6b,9,12a-hexamethyl-2,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylate
Synonyms:	Nigaichigoside F1
Standard InCHIKey:	WKKBYJLXSKPKSC-JVJIQXRHSA-N
Standard InCHI:	InChI=1S/C36H58O11/c1-18-9-12-36(30(44)47-29-26(42)25(41)24(40)21(16-37)46-29)14-13-33(4)19(27(36)35(18,6)45)7-8-23-31(2)15-20(39)28(43)32(3,17-38)22(31)10-11-34(23,33)5/h7,18,20-29,37-43,45H,8-17H2,1-6H3/t18-,20-,21-,22-,23-,24-,25+,26-,27-,28+,29+,31+,32+,33-,34-,35-,36+/m1/s1
SMILES:	OC[C@H]1O[C@@H](OC(=O)[C@@]23CC[C@H]([C@@]([C@H]3C3=CC[C@H]4[C@@]([C@@]3(CC2)C)(C)CC[C@@H]2[C@]4(C)C[C@H]([C@@H]([C@@]2(C)CO)O)O)(C)O)C)[C@@H]([C@H]([C@@H]1O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL449365
PubChem CID:	16118969
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0002049] Terpene glycosides [CHEMONTID:0001580] Triterpene glycosides [CHEMONTID:0002358] Triterpene saponins

*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
NPO19774	Rubus idaeus	Species	n.a.	n.a.	Fruit	n.a.	n.a.	DOI[10.1016/S0963-9969(99)00095-2]
NPO19281	Rubus imperialis	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[10479322]
NPO30384	Combretum quadrangulare	Species	Combretaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10650080]
NPO30384	Combretum quadrangulare	Species	Combretaceae	Eukaryota	seeds	n.a.	n.a.	PMID[10785422]
NPO30384	Combretum quadrangulare	Species	Combretaceae	Eukaryota	Seeds	n.a.	n.a.	PMID[11277757]
NPO26650	Terminalia chebula	Species	Combretaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11520216]
NPO15275	Briareum asbestinum	Species	Briareidae	Eukaryota	n.a.	n.a.	n.a.	PMID[12662092]
NPO1396	Cladogynos orientalis	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[15679308]
NPO15275	Briareum asbestinum	Species	Briareidae	Eukaryota	n.a.	Caribbean	n.a.	PMID[1686898]
NPO6741	Metasequoia glyptostroboides	Species	Cupressaceae	Eukaryota	n.a.	stem	n.a.	PMID[21226514]
NPO6741	Metasequoia glyptostroboides	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21226514]
NPO6741	Metasequoia glyptostroboides	Species	Cupressaceae	Eukaryota	n.a.	leaf	n.a.	PMID[21226514]
NPO30384	Combretum quadrangulare	Species	Combretaceae	Eukaryota	leaves	Khon Kaen, Thailand	2006-AUG	PMID[21265555]
NPO30384	Combretum quadrangulare	Species	Combretaceae	Eukaryota	n.a.	leaf	n.a.	PMID[21265555]
NPO19774	Rubus idaeus	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[21381697]
NPO7372	Rosa laevigata	Species	Rosaceae	Eukaryota	Leaves	Huangshan, Anhui Province, China	2008-NOV	PMID[21384845]
NPO7372	Rosa laevigata	Species	Rosaceae	Eukaryota	n.a.	leaf	n.a.	PMID[21384845]
NPO7372	Rosa laevigata	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23632365]
NPO25140	Sapium sebiferum	Species	Euphorbiaceae	Eukaryota	n.a.	leaf	n.a.	PMID[26281591]
NPO26261	Streptomyces tendae	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[27642865]
NPO25140	Sapium sebiferum	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[3404159]
NPO30384	Combretum quadrangulare	Species	Combretaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9934464]
NPO26622	Taraxacum officinale	Species	Asteraceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO10980	Petasites japonicus	Species	Asteraceae	Eukaryota	Pt	n.a.	n.a.	Database[FooDB]
NPO26622	Taraxacum officinale	Species	Asteraceae	Eukaryota	Root	n.a.	n.a.	Database[FooDB]
NPO19774	Rubus idaeus	Species	n.a.	n.a.	Seed	n.a.	n.a.	Database[FooDB]
NPO19774	Rubus idaeus	Species	n.a.	n.a.		n.a.	n.a.	Database[FooDB]
NPO10980	Petasites japonicus	Species	Asteraceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO19774	Rubus idaeus	Species	n.a.	n.a.	Fruits	n.a.		Database[FooDB]
NPO26622	Taraxacum officinale	Species	Asteraceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO26622	Taraxacum officinale	Species	Asteraceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO19774	Rubus idaeus	Species	n.a.	n.a.	Fruit	n.a.	n.a.	Database[FooDB]
NPO19774	Rubus idaeus	Species	n.a.	n.a.	Leaf	n.a.	n.a.	Database[FooDB]
NPO26622	Taraxacum officinale	Species	Asteraceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO7372	Rosa laevigata	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26650	Terminalia chebula	Species	Combretaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28375	Pygeum topengii	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18564	Ligularia dentata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12320	Adonis amurensis	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5166	Adonis sutchuenensis	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19774	Rubus idaeus	Species	n.a.	n.a.	n.a.	n.a.	n.a.	Database[HerDing]
NPO6741	Metasequoia glyptostroboides	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26622	Taraxacum officinale	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO10980	Petasites japonicus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19774	Rubus idaeus	Species	n.a.	n.a.	Fruits	n.a.		Database[Phenol-Explorer]
NPO19774	Rubus idaeus	Species	n.a.	n.a.	n.a.	n.a.		Database[Phenol-Explorer]
NPO26622	Taraxacum officinale	Species	Asteraceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO26650	Terminalia chebula	Species	Combretaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19774	Rubus idaeus	Species	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TCMID]
NPO28375	Pygeum topengii	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5166	Adonis sutchuenensis	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18564	Ligularia dentata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6741	Metasequoia glyptostroboides	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7372	Rosa laevigata	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11222	Rubus alceifolius	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12320	Adonis amurensis	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25140	Sapium sebiferum	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10980	Petasites japonicus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2663	Casimiroa tetrameria	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26622	Taraxacum officinale	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8306	Berneuxia thibetica	Species	Diapensiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26422	Rubus chingii	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO8306	Berneuxia thibetica	Species	Diapensiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO7372	Rosa laevigata	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO28375	Pygeum topengii	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO26622	Taraxacum officinale	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO12320	Adonis amurensis	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO26650	Terminalia chebula	Species	Combretaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO10980	Petasites japonicus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO26422	Rubus chingii	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO26622	Taraxacum officinale	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO26650	Terminalia chebula	Species	Combretaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO7372	Rosa laevigata	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO18930	Rubus coreanus	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO10980	Petasites japonicus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9182	Lychnophora passerina	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21493	Bunodosoma caissarum	Species	Actiniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26283	Streptomyces djakartensis	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO1507	Cissus quinquefolia	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1049	Tethya amamensis	Species	Tethyidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3868	Senecio sinuatus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26048	Grateloupia elliptica	Species	Halymeniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9388	Heliomeris multiflora	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1396	Cladogynos orientalis	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO28950	Angelonia integerrima	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7793	Matricaria matricarioides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25339	Trillium smallii	Species	Melanthiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4836	Sideritis arborescens	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18930	Rubus coreanus	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2977	Colletotrichum lagenaria	Species	Glomerellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17179	Elizabethkingia meningoseptica	Species	Flavobacteriaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO7372	Rosa laevigata	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19281	Rubus imperialis	Species	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO28375	Pygeum topengii	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1541	Clusia ellipticifolia	Species	Clusiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4318	Aspergillus cristatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19991	Mantella aurantiaca	Species	Mantellidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26422	Rubus chingii	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5166	Adonis sutchuenensis	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12320	Adonis amurensis	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2323	Plantago lundborgii	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18564	Ligularia dentata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26261	Streptomyces tendae	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO13682	Lonchocarpus laxiflorus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11165	Spirographis spallanzani	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO643	Astragalus ernestii	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5214	Machaerium nictitans	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15275	Briareum asbestinum	Species	Briareidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26650	Terminalia chebula	Species	Combretaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26399	Crepidiastrum lanceolatum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25140	Sapium sebiferum	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5339	Isophysis tasmanica	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1706	Eragrostis curvula	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25649	Calliandra haematocephala	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25765	Dryopteris aemula	Species	Dryopteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1203	Solanum pseudoquina	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26345	Sideroxylon tomentosum	Species	Sapotaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21211	Penicillium stipitatum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8306	Berneuxia thibetica	Species	Diapensiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8433	Bongardia chrysogonum	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8950	Stilpnopappus pickelii	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO24698	Protium unifoliolatum	Species	Burseraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3367	Cassytha racemosa	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO117	Acacia armata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19774	Rubus idaeus	Species	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO6741	Metasequoia glyptostroboides	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11222	Rubus alceifolius	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4855	Colchicum speciosum	Species	Colchicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8132	Fritillaria meleagris	Species	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2663	Casimiroa tetrameria	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2008	Streptomyces ehimensis	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO25992	Lasallia papulosa	Species	Umbilicariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26622	Taraxacum officinale	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3445	Dumoria heckeli	n.a.	n.a.	n.a.	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
Others	7

Activity Type	# Activity
Organism	7

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT32	Organism	Mus musculus	Mus musculus	ID50	=	4.6	umol.kg-1	PMID[489694]
NPT32	Organism	Mus musculus	Mus musculus	Inhibition	=	67.6	%	PMID[489694]
NPT32	Organism	Mus musculus	Mus musculus	ID50	=	3.9	umol.kg-1	PMID[489694]
NPT32	Organism	Mus musculus	Mus musculus	Inhibition	=	70.4	%	PMID[489694]
NPT32	Organism	Mus musculus	Mus musculus	ID50	=	4.1	umol.kg-1	PMID[489694]
NPT32	Organism	Mus musculus	Mus musculus	Inhibition	=	94.0	%	PMID[489694]
NPT786	Organism	Tobacco mosaic virus	Tobacco mosaic virus	Inhibition	=	24.9	%	PMID[489695]

☑ 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 NPC271138 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	273
0.1-0.2	1749
0.2-0.3	4944
0.3-0.4	10846
0.4-0.5	10906
0.5-0.6	6450
0.6-0.7	4331
0.7-0.8	1936
0.8-0.85	595
0.85-0.9	311
0.9-0.95	169
0.95-1	187

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC269315
0.9904	High Similarity	NPC116794
0.9904	High Similarity	NPC37739
0.9904	High Similarity	NPC46388
0.981	High Similarity	NPC47063
0.981	High Similarity	NPC204458
0.981	High Similarity	NPC138334
0.981	High Similarity	NPC189884
0.9808	High Similarity	NPC191763
0.9717	High Similarity	NPC475633
0.9714	High Similarity	NPC256798
0.9714	High Similarity	NPC128925
0.9712	High Similarity	NPC102914
0.9712	High Similarity	NPC7870
0.9712	High Similarity	NPC75747
0.9712	High Similarity	NPC68419
0.9712	High Similarity	NPC108709
0.9712	High Similarity	NPC110139
0.9712	High Similarity	NPC274507
0.9712	High Similarity	NPC199457
0.9626	High Similarity	NPC160415
0.9626	High Similarity	NPC58448
0.9619	High Similarity	NPC108748
0.9619	High Similarity	NPC211798
0.9619	High Similarity	NPC473481
0.9619	High Similarity	NPC297208
0.9619	High Similarity	NPC30397
0.9619	High Similarity	NPC235841
0.9619	High Similarity	NPC179434
0.9615	High Similarity	NPC237503
0.9615	High Similarity	NPC167383
0.9615	High Similarity	NPC306746
0.9615	High Similarity	NPC204407
0.9615	High Similarity	NPC57362
0.9615	High Similarity	NPC127853
0.9537	High Similarity	NPC68175
0.9528	High Similarity	NPC473383
0.9528	High Similarity	NPC139894
0.9528	High Similarity	NPC48249
0.9524	High Similarity	NPC476880
0.9524	High Similarity	NPC174679
0.9524	High Similarity	NPC164194
0.9524	High Similarity	NPC476881
0.9524	High Similarity	NPC90856
0.9524	High Similarity	NPC270667
0.9524	High Similarity	NPC476886
0.9524	High Similarity	NPC29069
0.9524	High Similarity	NPC475296
0.9524	High Similarity	NPC476883
0.9524	High Similarity	NPC220984
0.9524	High Similarity	NPC127056
0.9524	High Similarity	NPC56713
0.9524	High Similarity	NPC136877
0.9524	High Similarity	NPC476885
0.9524	High Similarity	NPC476887
0.9524	High Similarity	NPC476884
0.9524	High Similarity	NPC476882
0.9524	High Similarity	NPC474589
0.9524	High Similarity	NPC279554
0.9524	High Similarity	NPC59804
0.9519	High Similarity	NPC177246
0.9519	High Similarity	NPC476123
0.9519	High Similarity	NPC285576
0.9519	High Similarity	NPC284807
0.9519	High Similarity	NPC28198
0.945	High Similarity	NPC36831
0.9444	High Similarity	NPC161674
0.9444	High Similarity	NPC471384
0.9439	High Similarity	NPC73318
0.9439	High Similarity	NPC258885
0.9439	High Similarity	NPC134835
0.9439	High Similarity	NPC96641
0.9439	High Similarity	NPC475208
0.9439	High Similarity	NPC150400
0.9439	High Similarity	NPC124296
0.9439	High Similarity	NPC238935
0.9439	High Similarity	NPC163183
0.9439	High Similarity	NPC473343
0.9434	High Similarity	NPC31839
0.9434	High Similarity	NPC164419
0.9429	High Similarity	NPC137917
0.9423	High Similarity	NPC283849
0.9423	High Similarity	NPC473538
0.9358	High Similarity	NPC110633
0.9358	High Similarity	NPC148417
0.9358	High Similarity	NPC300419
0.9358	High Similarity	NPC136768
0.9346	High Similarity	NPC109079
0.9346	High Similarity	NPC101744
0.9346	High Similarity	NPC324875
0.9346	High Similarity	NPC10320
0.9346	High Similarity	NPC471383
0.9346	High Similarity	NPC102439
0.9346	High Similarity	NPC212968
0.9346	High Similarity	NPC104071
0.9346	High Similarity	NPC80843
0.9346	High Similarity	NPC79718
0.9346	High Similarity	NPC469946
0.9346	High Similarity	NPC471967
0.9346	High Similarity	NPC1046
0.9346	High Similarity	NPC475516
0.9346	High Similarity	NPC139044
0.9346	High Similarity	NPC104400
0.9346	High Similarity	NPC292677
0.9346	High Similarity	NPC125923
0.9346	High Similarity	NPC475504
0.9346	High Similarity	NPC65590
0.9346	High Similarity	NPC64106
0.9346	High Similarity	NPC276093
0.9346	High Similarity	NPC257468
0.9346	High Similarity	NPC473373
0.934	High Similarity	NPC269095
0.934	High Similarity	NPC78046
0.934	High Similarity	NPC242611
0.9327	High Similarity	NPC475611
0.9279	High Similarity	NPC473645
0.9279	High Similarity	NPC268184
0.9273	High Similarity	NPC475899
0.9266	High Similarity	NPC37134
0.9266	High Similarity	NPC291903
0.9259	High Similarity	NPC219180
0.9259	High Similarity	NPC475287
0.9259	High Similarity	NPC475467
0.9259	High Similarity	NPC473826
0.9259	High Similarity	NPC192600
0.9259	High Similarity	NPC166422
0.9259	High Similarity	NPC114304
0.9259	High Similarity	NPC174720
0.9259	High Similarity	NPC241909
0.9259	High Similarity	NPC155410
0.9259	High Similarity	NPC295823
0.9259	High Similarity	NPC114287
0.9259	High Similarity	NPC151543
0.9259	High Similarity	NPC133818
0.9259	High Similarity	NPC323341
0.9259	High Similarity	NPC309714
0.9259	High Similarity	NPC251263
0.9259	High Similarity	NPC46665
0.9252	High Similarity	NPC190837
0.9196	High Similarity	NPC75417
0.9189	High Similarity	NPC471577
0.9189	High Similarity	NPC477464
0.9182	High Similarity	NPC475119
0.9182	High Similarity	NPC471547
0.9182	High Similarity	NPC473824
0.9182	High Similarity	NPC473405
0.9174	High Similarity	NPC294453
0.9174	High Similarity	NPC67857
0.9174	High Similarity	NPC227551
0.9174	High Similarity	NPC76972
0.9174	High Similarity	NPC293330
0.9174	High Similarity	NPC250247
0.9174	High Similarity	NPC71065
0.9174	High Similarity	NPC119592
0.9174	High Similarity	NPC298034
0.9174	High Similarity	NPC54636
0.9174	High Similarity	NPC79643
0.9174	High Similarity	NPC4328
0.9174	High Similarity	NPC475140
0.9174	High Similarity	NPC164389
0.9174	High Similarity	NPC261506
0.9174	High Similarity	NPC57484
0.9174	High Similarity	NPC471550
0.9174	High Similarity	NPC202828
0.9174	High Similarity	NPC476068
0.9174	High Similarity	NPC123199
0.9174	High Similarity	NPC41061
0.9174	High Similarity	NPC305981
0.9174	High Similarity	NPC309907
0.9174	High Similarity	NPC471385
0.9174	High Similarity	NPC60557
0.9174	High Similarity	NPC236638
0.9174	High Similarity	NPC224381
0.9174	High Similarity	NPC161717
0.9174	High Similarity	NPC70809
0.9174	High Similarity	NPC102088
0.9174	High Similarity	NPC204414
0.9174	High Similarity	NPC473714
0.9174	High Similarity	NPC469782
0.9174	High Similarity	NPC43550
0.9174	High Similarity	NPC65105
0.9174	High Similarity	NPC475486
0.9174	High Similarity	NPC100639
0.9174	High Similarity	NPC475160
0.9167	High Similarity	NPC100383
0.9167	High Similarity	NPC161434
0.9167	High Similarity	NPC195132
0.9159	High Similarity	NPC475501
0.9143	High Similarity	NPC477877
0.9107	High Similarity	NPC153673
0.9107	High Similarity	NPC142151
0.9107	High Similarity	NPC37860
0.9107	High Similarity	NPC110385
0.9107	High Similarity	NPC267694
0.9107	High Similarity	NPC144644
0.9099	High Similarity	NPC232237
0.9099	High Similarity	NPC105800
0.9099	High Similarity	NPC109588
0.9099	High Similarity	NPC237191
0.9099	High Similarity	NPC471548

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 NPC271138 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	250
0.1-0.2	2046
0.2-0.3	3803
0.3-0.4	1965
0.4-0.5	635
0.5-0.6	290
0.6-0.7	127
0.7-0.8	27
0.8-0.85	4
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9065	High Similarity	NPD8132	Clinical (unspecified phase)
0.8839	High Similarity	NPD8295	Clinical (unspecified phase)
0.8707	High Similarity	NPD8328	Phase 3
0.8246	Intermediate Similarity	NPD8133	Approved
0.8036	Intermediate Similarity	NPD6412	Phase 2
0.7965	Intermediate Similarity	NPD6686	Approved
0.7963	Intermediate Similarity	NPD7902	Approved
0.7951	Intermediate Similarity	NPD7507	Approved
0.7917	Intermediate Similarity	NPD8033	Approved
0.785	Intermediate Similarity	NPD7748	Approved
0.7833	Intermediate Similarity	NPD8377	Approved
0.7833	Intermediate Similarity	NPD8294	Approved
0.7769	Intermediate Similarity	NPD8380	Approved
0.7769	Intermediate Similarity	NPD8335	Approved
0.7769	Intermediate Similarity	NPD8378	Approved
0.7769	Intermediate Similarity	NPD8513	Phase 3
0.7769	Intermediate Similarity	NPD8379	Approved
0.7769	Intermediate Similarity	NPD8296	Approved
0.7769	Intermediate Similarity	NPD8515	Approved
0.7769	Intermediate Similarity	NPD8517	Approved
0.7769	Intermediate Similarity	NPD8516	Approved
0.776	Intermediate Similarity	NPD7319	Approved
0.775	Intermediate Similarity	NPD7516	Approved
0.7685	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7685	Intermediate Similarity	NPD7900	Approved
0.768	Intermediate Similarity	NPD7736	Approved
0.7667	Intermediate Similarity	NPD7327	Approved
0.7667	Intermediate Similarity	NPD7328	Approved
0.7664	Intermediate Similarity	NPD7515	Phase 2
0.748	Intermediate Similarity	NPD7503	Approved
0.746	Intermediate Similarity	NPD8293	Discontinued
0.735	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7339	Intermediate Similarity	NPD8035	Phase 2
0.7339	Intermediate Similarity	NPD8034	Phase 2
0.7311	Intermediate Similarity	NPD8413	Clinical (unspecified phase)
0.7288	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.728	Intermediate Similarity	NPD6370	Approved
0.7273	Intermediate Similarity	NPD6399	Phase 3
0.725	Intermediate Similarity	NPD8297	Approved
0.725	Intermediate Similarity	NPD6882	Approved
0.7227	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7165	Intermediate Similarity	NPD7492	Approved
0.7154	Intermediate Similarity	NPD7115	Discovery
0.7154	Intermediate Similarity	NPD6009	Approved
0.7143	Intermediate Similarity	NPD6373	Approved
0.7143	Intermediate Similarity	NPD6372	Approved
0.712	Intermediate Similarity	NPD6319	Approved
0.712	Intermediate Similarity	NPD6059	Approved
0.712	Intermediate Similarity	NPD6054	Approved
0.7109	Intermediate Similarity	NPD6616	Approved
0.7105	Intermediate Similarity	NPD7638	Approved
0.7094	Intermediate Similarity	NPD8170	Clinical (unspecified phase)
0.7054	Intermediate Similarity	NPD7078	Approved
0.7049	Intermediate Similarity	NPD4632	Approved
0.7043	Intermediate Similarity	NPD7639	Approved
0.7043	Intermediate Similarity	NPD7640	Approved
0.7034	Intermediate Similarity	NPD6402	Approved
0.7034	Intermediate Similarity	NPD7128	Approved
0.7034	Intermediate Similarity	NPD5739	Approved
0.7034	Intermediate Similarity	NPD6675	Approved
0.7025	Intermediate Similarity	NPD6650	Approved
0.7025	Intermediate Similarity	NPD6649	Approved
0.7019	Intermediate Similarity	NPD7645	Phase 2
0.6975	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6953	Remote Similarity	NPD6067	Discontinued
0.6944	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6929	Remote Similarity	NPD6016	Approved
0.6929	Remote Similarity	NPD6015	Approved
0.6923	Remote Similarity	NPD8074	Phase 3
0.6917	Remote Similarity	NPD6899	Approved
0.6917	Remote Similarity	NPD7320	Approved
0.6917	Remote Similarity	NPD6881	Approved
0.6891	Remote Similarity	NPD6008	Approved
0.6885	Remote Similarity	NPD8130	Phase 1
0.6875	Remote Similarity	NPD5988	Approved
0.6875	Remote Similarity	NPD6411	Approved
0.6833	Remote Similarity	NPD5697	Approved
0.6833	Remote Similarity	NPD5701	Approved
0.681	Remote Similarity	NPD4225	Approved
0.6803	Remote Similarity	NPD6883	Approved
0.6803	Remote Similarity	NPD7102	Approved
0.6803	Remote Similarity	NPD7290	Approved
0.6797	Remote Similarity	NPD6921	Approved
0.6786	Remote Similarity	NPD46	Approved
0.6786	Remote Similarity	NPD6698	Approved
0.6748	Remote Similarity	NPD6869	Approved
0.6748	Remote Similarity	NPD6847	Approved
0.6748	Remote Similarity	NPD6617	Approved
0.6727	Remote Similarity	NPD3618	Phase 1
0.6724	Remote Similarity	NPD6084	Phase 2
0.6724	Remote Similarity	NPD6083	Phase 2
0.6721	Remote Similarity	NPD6014	Approved
0.6721	Remote Similarity	NPD6013	Approved
0.6721	Remote Similarity	NPD6012	Approved
0.6697	Remote Similarity	NPD4786	Approved
0.6696	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6696	Remote Similarity	NPD6101	Approved
0.6692	Remote Similarity	NPD7604	Phase 2
0.6667	Remote Similarity	NPD3667	Approved
0.6667	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5983	Phase 2
0.6667	Remote Similarity	NPD8171	Discontinued
0.6667	Remote Similarity	NPD3573	Approved
0.6639	Remote Similarity	NPD6011	Approved
0.6617	Remote Similarity	NPD6033	Approved
0.6613	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6607	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6606	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.6606	Remote Similarity	NPD3669	Approved
0.6591	Remote Similarity	NPD6336	Discontinued
0.6581	Remote Similarity	NPD4755	Approved
0.6579	Remote Similarity	NPD7983	Approved
0.6555	Remote Similarity	NPD5344	Discontinued
0.6549	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6549	Remote Similarity	NPD5328	Approved
0.6532	Remote Similarity	NPD4634	Approved
0.6525	Remote Similarity	NPD5696	Approved
0.6522	Remote Similarity	NPD5778	Approved
0.6522	Remote Similarity	NPD5779	Approved
0.6522	Remote Similarity	NPD4202	Approved
0.65	Remote Similarity	NPD7632	Discontinued
0.6481	Remote Similarity	NPD7525	Registered
0.6471	Remote Similarity	NPD4700	Approved
0.6471	Remote Similarity	NPD5285	Approved
0.6471	Remote Similarity	NPD5286	Approved
0.6471	Remote Similarity	NPD4696	Approved
0.6435	Remote Similarity	NPD6079	Approved
0.6429	Remote Similarity	NPD6684	Approved
0.6429	Remote Similarity	NPD7521	Approved
0.6429	Remote Similarity	NPD6409	Approved
0.6429	Remote Similarity	NPD7146	Approved
0.6429	Remote Similarity	NPD5330	Approved
0.6429	Remote Similarity	NPD7334	Approved
0.6423	Remote Similarity	NPD8449	Approved
0.6422	Remote Similarity	NPD1779	Approved
0.6422	Remote Similarity	NPD1780	Approved
0.6414	Remote Similarity	NPD7625	Phase 1
0.641	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.641	Remote Similarity	NPD5695	Phase 3
0.6406	Remote Similarity	NPD6940	Discontinued
0.6406	Remote Similarity	NPD6274	Approved
0.6391	Remote Similarity	NPD8342	Approved
0.6391	Remote Similarity	NPD8340	Approved
0.6391	Remote Similarity	NPD8341	Approved
0.6391	Remote Similarity	NPD8299	Approved
0.6385	Remote Similarity	NPD7100	Approved
0.6385	Remote Similarity	NPD7101	Approved
0.6377	Remote Similarity	NPD8450	Suspended
0.6372	Remote Similarity	NPD7524	Approved
0.6364	Remote Similarity	NPD5224	Approved
0.6364	Remote Similarity	NPD4633	Approved
0.6364	Remote Similarity	NPD5211	Phase 2
0.6364	Remote Similarity	NPD5225	Approved
0.6364	Remote Similarity	NPD5226	Approved
0.6357	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.6356	Remote Similarity	NPD4697	Phase 3
0.6343	Remote Similarity	NPD8451	Approved
0.6341	Remote Similarity	NPD4767	Approved
0.6341	Remote Similarity	NPD4768	Approved
0.6316	Remote Similarity	NPD5737	Approved
0.6316	Remote Similarity	NPD6903	Approved
0.6316	Remote Similarity	NPD6672	Approved
0.6311	Remote Similarity	NPD5174	Approved
0.6311	Remote Similarity	NPD5175	Approved
0.6308	Remote Similarity	NPD7641	Discontinued
0.6308	Remote Similarity	NPD6335	Approved
0.6299	Remote Similarity	NPD6053	Discontinued
0.6296	Remote Similarity	NPD8448	Approved
0.6296	Remote Similarity	NPD6114	Approved
0.6296	Remote Similarity	NPD6697	Approved
0.6296	Remote Similarity	NPD6115	Approved
0.6296	Remote Similarity	NPD6118	Approved
0.629	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6288	Remote Similarity	NPD6909	Approved
0.6288	Remote Similarity	NPD6908	Approved
0.6281	Remote Similarity	NPD5223	Approved
0.6277	Remote Similarity	NPD8390	Approved
0.6277	Remote Similarity	NPD8392	Approved
0.6277	Remote Similarity	NPD8391	Approved
0.627	Remote Similarity	NPD6371	Approved
0.6261	Remote Similarity	NPD4753	Phase 2
0.626	Remote Similarity	NPD5141	Approved
0.625	Remote Similarity	NPD3665	Phase 1
0.625	Remote Similarity	NPD3668	Phase 3
0.625	Remote Similarity	NPD3666	Approved
0.625	Remote Similarity	NPD3133	Approved
0.624	Remote Similarity	NPD4730	Approved
0.624	Remote Similarity	NPD4729	Approved
0.6231	Remote Similarity	NPD6317	Approved
0.6218	Remote Similarity	NPD5221	Approved
0.6218	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6218	Remote Similarity	NPD5222	Approved
0.6218	Remote Similarity	NPD7839	Suspended
0.6207	Remote Similarity	NPD7838	Discovery
0.6207	Remote Similarity	NPD3168	Discontinued
0.6204	Remote Similarity	NPD6116	Phase 1
0.6198	Remote Similarity	NPD6648	Approved
0.6187	Remote Similarity	NPD8338	Approved
0.6186	Remote Similarity	NPD5282	Discontinued
0.6183	Remote Similarity	NPD6314	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