NPASS Compound

Structure

CID308267 OpenBabel06191716112D 26 30 0 0 0 0 0 0 0 0999 V2000 1.7377 -2.0534 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9187 2.2872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9242 2.3917 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2276 -1.2444 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2765 -1.5534 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2765 1.6826 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6814 -0.9354 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6814 1.0646 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7377 -0.4354 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.0862 0.0646 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3255 1.3736 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8154 -0.4354 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8154 0.5646 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7377 0.5646 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2276 1.3736 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3364 1.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5474 -0.4354 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5474 0.5646 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7431 0.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3255 -1.2444 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 4.8154 2.1826 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6581 1.4781 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.4985 -0.7444 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.4985 0.8736 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 1 21 1 0 0 0 0 2 3 2 0 0 0 0 2 12 1 0 0 0 0 3 17 1 0 0 0 0 4 5 1 0 0 0 0 4 13 1 0 0 0 0 5 21 1 0 0 0 0 6 12 1 0 0 0 0 6 16 1 0 0 0 0 7 13 2 0 0 0 0 7 18 1 0 0 0 0 8 14 2 0 0 0 0 8 19 1 0 0 0 0 9 15 1 0 0 0 0 9 21 1 0 0 0 0 10 24 1 0 0 0 0 10 25 1 0 0 0 0 11 23 1 0 0 0 0 11 26 1 0 0 0 0 12 15 2 0 0 0 0 13 14 1 0 0 0 0 14 16 1 0 0 0 0 15 20 1 0 0 0 0 16 22 2 0 0 0 0 17 20 2 0 0 0 0 17 23 1 0 0 0 0 18 19 2 0 0 0 0 18 24 1 0 0 0 0 19 25 1 0 0 0 0 20 26 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	353.13
Volume:	348.187
LogP:	3.188
LogD:	2.586
LogS:	-4.683
# Rotatable Bonds:	0
TPSA:	57.23
# H-Bond Aceptor:	6
# H-Bond Donor:	0
# Rings:	5
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.726
Synthetic Accessibility Score:	3.189
Fsp3:	0.35
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.999
MDCK Permeability:	3.0512112061842345e-05
Pgp-inhibitor:	0.011
Pgp-substrate:	0.004
Human Intestinal Absorption (HIA):	0.001
20% Bioavailability (F20%):	0.006
30% Bioavailability (F30%):	0.004

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.97
Plasma Protein Binding (PPB):	92.89724731445312%
Volume Distribution (VD):	2.131
Pgp-substrate:	4.743223190307617%

ADMET: Metabolism

CYP1A2-inhibitor:	0.955
CYP1A2-substrate:	0.258
CYP2C19-inhibitor:	0.939
CYP2C19-substrate:	0.847
CYP2C9-inhibitor:	0.064
CYP2C9-substrate:	0.778
CYP2D6-inhibitor:	0.986
CYP2D6-substrate:	0.918
CYP3A4-inhibitor:	0.964
CYP3A4-substrate:	0.771

ADMET: Excretion

Clearance (CL):	16.684
Half-life (T1/2):	0.229

ADMET: Toxicity

hERG Blockers:	0.523
Human Hepatotoxicity (H-HT):	0.284
Drug-inuced Liver Injury (DILI):	0.889
AMES Toxicity:	0.25
Rat Oral Acute Toxicity:	0.21
Maximum Recommended Daily Dose:	0.225
Skin Sensitization:	0.181
Carcinogencity:	0.875
Eye Corrosion:	0.003
Eye Irritation:	0.008
Respiratory Toxicity:	0.625

Download Data

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

Natural Product: NPC308267

Natural Product ID:	NPC308267
*Common Name:**	GPTFURBXHJWNHR-UHFFFAOYSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	GPTFURBXHJWNHR-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C20H19NO5/c1-21-5-4-13-7-18-19(25-10-24-18)8-14(13)16(22)6-12-2-3-17-20(15(12)9-21)26-11-23-17/h2-3,7-8H,4-6,9-11H2,1H3
SMILES:	CN1CCc2cc3OCOc3cc2C(=O)Cc2c(C1)c1OCOc1cc2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL453019
PubChem CID:	4970
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0002743] Protopine alkaloids

*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
NPO7103	Allium sativum	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.3923/pjbs.2013.1138.1144]
NPO24758	Angelica dahurica	Species	Apiaceae	Eukaryota	n.a.	root	n.a.	DOI[10.5012/bkcs.2003.24.11.1699]
NPO26193	Piper methysticum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11830162]
NPO29080	Ulex airensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11858751]
NPO20958	Smenospongia aurea	Species	Thorectidae	Eukaryota	n.a.	Jamaican	n.a.	PMID[11975483]
NPO24758	Angelica dahurica	Species	Apiaceae	Eukaryota	n.a.	root	n.a.	PMID[12510838]
NPO26193	Piper methysticum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12809361]
NPO14337	Ecklonia stolonifera	Species	Lessoniaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12913249]
NPO20254	Ipomoea leptophylla	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[14640518]
NPO9498	Papaver somniferum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15019787]
NPO22556	Dendrolobium lanceolatum	Species	Fabaceae	Eukaryota	n.a.	root	n.a.	PMID[15217275]
NPO24758	Angelica dahurica	Species	Apiaceae	Eukaryota	n.a.	root	n.a.	PMID[15646793]
NPO7103	Allium sativum	Species	Amaryllidaceae	Eukaryota	n.a.	leaf	n.a.	PMID[17262437]
NPO25373	Stereocaulon alpinum	Species	Stereocaulaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18288807]
NPO7103	Allium sativum	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18326559]
NPO7103	Allium sativum	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18460139]
NPO21782	Nuxia sphaerocephala	Species	Stilbaceae	Eukaryota	leaves	n.a.	n.a.	PMID[19299148]
NPO927	Swertia mussotii	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19645233]
NPO25345	Corydalis ternata	Species	Papaveraceae	Eukaryota	tubers	n.a.	n.a.	PMID[20594848]
NPO24758	Angelica dahurica	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21625478]
NPO24758	Angelica dahurica	Species	Apiaceae	Eukaryota	n.a.	root	n.a.	PMID[21657081]
NPO2020	Corydalis cava	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22029392]
NPO8675	Fumaria vaillantii	Species	Papaveraceae	Eukaryota	n.a.	seed	n.a.	PMID[22029392]
NPO8675	Fumaria vaillantii	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22029392]
NPO9498	Papaver somniferum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22029392]
NPO8675	Fumaria vaillantii	Species	Papaveraceae	Eukaryota	n.a.	aerial part	n.a.	PMID[22029392]
NPO8675	Fumaria vaillantii	Species	Papaveraceae	Eukaryota	n.a.	root	n.a.	PMID[22029392]
NPO827	Corydalis yanhusuo	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22737858]
NPO7103	Allium sativum	Species	Amaryllidaceae	Eukaryota	Essential oil	n.a.	n.a.	PMID[23163425]
NPO827	Corydalis yanhusuo	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23194502]
NPO9498	Papaver somniferum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23517479]
NPO7103	Allium sativum	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23865201]
NPO7103	Allium sativum	Species	Amaryllidaceae	Eukaryota	n.a.	bulb	n.a.	PMID[24508058]
NPO26428	Ligularia sagitta	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24913558]
NPO13962	Corydalis turtschaninovii	Species	Papaveraceae	Eukaryota	n.a.	rhizome	n.a.	PMID[25277281]
NPO26193	Piper methysticum	Species	Piperaceae	Eukaryota	root	n.a.	n.a.	PMID[25597012]
NPO7103	Allium sativum	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25650289]
NPO13962	Corydalis turtschaninovii	Species	Papaveraceae	Eukaryota	n.a.	tuber	n.a.	PMID[25670016]
NPO7103	Allium sativum	Species	Amaryllidaceae	Eukaryota	garlic skin	n.a.	n.a.	PMID[25726329]
NPO24758	Angelica dahurica	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27444348]
NPO5305	Corydalis mucronifera	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[29400966]
NPO41827	Yarrowia lipolytica ST7403 [crtW crtZ]	Strain	Dipodascaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[29552653]
NPO25373	Stereocaulon alpinum	Species	Stereocaulaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[29878768]
NPO22441	Senna spectabilis	Species	Fabaceae	Eukaryota	flowers	n.a.	n.a.	PMID[30413343]
NPO24758	Angelica dahurica	Species	Apiaceae	Eukaryota	Roots	n.a.	n.a.	PMID[31464439]
NPO14045	Corydalis decumbens	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31599578]
NPO827	Corydalis yanhusuo	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32058719]
NPO7103	Allium sativum	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8350088]
NPO25657	Mezzettia leptopoda	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9868159]
NPO927	Swertia mussotii	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[Article]
NPO7103	Allium sativum	Species	Amaryllidaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO7103	Allium sativum	Species	Amaryllidaceae	Eukaryota	Bulb	n.a.	n.a.	Database[FooDB]
NPO7103	Allium sativum	Species	Amaryllidaceae	Eukaryota	Flower	n.a.	n.a.	Database[FooDB]
NPO9498	Papaver somniferum	Species	Papaveraceae	Eukaryota	Latex Exudate	n.a.	n.a.	Database[FooDB]
NPO7103	Allium sativum	Species	Amaryllidaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO7103	Allium sativum	Species	Amaryllidaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO7103	Allium sativum	Species	Amaryllidaceae	Eukaryota	Root	n.a.	n.a.	Database[FooDB]
NPO9498	Papaver somniferum	Species	Papaveraceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO7103	Allium sativum	Species	Amaryllidaceae	Eukaryota	Shoot	n.a.	n.a.	Database[FooDB]
NPO9498	Papaver somniferum	Species	Papaveraceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO7103	Allium sativum	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO9498	Papaver somniferum	Species	Papaveraceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO24758	Angelica dahurica	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14045	Corydalis decumbens	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29249	Prunus humilis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8675	Fumaria vaillantii	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13887	Erythrophleum suaveolens	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29514	Stizolobium capitatum	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[HerDing]
NPO21782	Nuxia sphaerocephala	Species	Stilbaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24476	Phellodendron amurense	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO827	Corydalis yanhusuo	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO927	Swertia mussotii	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28612	Hypecoum leptocarpum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24480	Diospyros ebenum	Species	Ebenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2020	Corydalis cava	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22242	Phellodendron chinense	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7103	Allium sativum	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14337	Ecklonia stolonifera	Species	Lessoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11457	Chelidonium majus	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1106	Artabotrys maingayi	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23223	Symphytum officinale	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26193	Piper methysticum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO16414	Thuja plicata	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5305	Corydalis mucronifera	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO20090	Dalbergia spruceana	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24584	Corydalis bungeana	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9498	Papaver somniferum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26428	Ligularia sagitta	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7103	Allium sativum	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO29514	Stizolobium capitatum	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TCMID]
NPO1106	Artabotrys maingayi	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24758	Angelica dahurica	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21782	Nuxia sphaerocephala	Species	Stilbaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24480	Diospyros ebenum	Species	Ebenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29249	Prunus humilis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24476	Phellodendron amurense	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14045	Corydalis decumbens	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20090	Dalbergia spruceana	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24087	Psacalium peltatum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26230	Lappula echinata	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26506	Hypecoum erectum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5305	Corydalis mucronifera	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28612	Hypecoum leptocarpum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22242	Phellodendron chinense	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO927	Swertia mussotii	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24584	Corydalis bungeana	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25166	Corydalis ophiocarpa	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO827	Corydalis yanhusuo	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14337	Ecklonia stolonifera	Species	Lessoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9498	Papaver somniferum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26193	Piper methysticum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11457	Chelidonium majus	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7103	Allium sativum	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23223	Symphytum officinale	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2020	Corydalis cava	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26428	Ligularia sagitta	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13887	Erythrophleum suaveolens	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8675	Fumaria vaillantii	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25373	Stereocaulon alpinum	Species	Stereocaulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16414	Thuja plicata	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23223	Symphytum officinale	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO22242	Phellodendron chinense	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO7103	Allium sativum	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO26506	Hypecoum erectum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO8675	Fumaria vaillantii	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO25166	Corydalis ophiocarpa	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO827	Corydalis yanhusuo	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO26193	Piper methysticum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO24758	Angelica dahurica	Species	Apiaceae	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]
NPO13887	Erythrophleum suaveolens	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO24476	Phellodendron amurense	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO5305	Corydalis mucronifera	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO24480	Diospyros ebenum	Species	Ebenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO11457	Chelidonium majus	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO20090	Dalbergia spruceana	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO14045	Corydalis decumbens	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO24758	Angelica dahurica	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO24584	Corydalis bungeana	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO29249	Prunus humilis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO22242	Phellodendron chinense	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO26538	Phellodendron chinese	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO13962	Corydalis turtschaninovii	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO25345	Corydalis ternata	Species	Papaveraceae	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]
NPO11457	Chelidonium majus	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO14045	Corydalis decumbens	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO24476	Phellodendron amurense	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO7103	Allium sativum	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO827	Corydalis yanhusuo	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO1954	Colletotrichum capsici	Species	Glomerellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26230	Lappula echinata	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23223	Symphytum officinale	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21782	Nuxia sphaerocephala	Species	Stilbaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22441	Senna spectabilis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1112	Papaver armeniacum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25881	Stachys plumosa	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15455	Karwinskia johnstonii	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1818	Chelidonium japonicum	Species	Cerambycidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20090	Dalbergia spruceana	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO927	Swertia mussotii	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20958	Smenospongia aurea	Species	Thorectidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26193	Piper methysticum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25624	Teclea sudanica	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29520	Curculigo breviscapa	Species	Hypoxidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9498	Papaver somniferum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2466	Aloe microstigma	Species	Asphodelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22495	Cladonia alpestris	Species	Cladoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8144	Labidiaster annulatus	Species	Labidiasteridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29235	Musca autumnalis	Species	Muscidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23296	Teucrium carolipaui	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29514	Stizolobium capitatum	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO7103	Allium sativum	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16670	Centaurea sclerolepis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18257	Oberna wallichiana	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO7063	Gentianella amarella	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8675	Fumaria vaillantii	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24480	Diospyros ebenum	Species	Ebenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15522	Michelia fuscata	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26740	Tolypothrix distorta	Species	Tolypothrichaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO24087	Psacalium peltatum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21848	Rosa hybr	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19966	Dendrobium amplum	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22556	Dendrolobium lanceolatum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2826	Pseudocercospora cruenta	Species	Mycosphaerellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15415	Othonna obtusiloba	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25166	Corydalis ophiocarpa	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29249	Prunus humilis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25484	Bumelia obtusifolia	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO336	Chaetomorpha moniligera	Species	Cladophoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16414	Thuja plicata	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26963	Sarcocapnos enneaphylla	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13235	Berberis chitria	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10176	Chrozophora prostrata	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4595	Biprorulus bibax	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO25373	Stereocaulon alpinum	Species	Stereocaulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28873	Epinetrum mangenotii	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO20254	Ipomoea leptophylla	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5305	Corydalis mucronifera	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14659	Cereus pecten-aboriginum	Species	Sagartiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29053	Dictyostelium longosporum	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25316	Lasius niger	Species	Formicidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25505	Astilbe japonica	Species	Saxifragaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1106	Artabotrys maingayi	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5491	Critonia daleoides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14326	Pseudocercospora fijiensis	Species	Mycosphaerellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14045	Corydalis decumbens	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7177	Inocybe rimosa	Species	Inocybaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9511	Ranunculus serbicus	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29080	Ulex airensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO434	Parasenecio petasitoides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24476	Phellodendron amurense	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7312	Aplidium multiplicatum	Species	Polyclinidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25345	Corydalis ternata	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO827	Corydalis yanhusuo	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28458	Coccoloba dugandiana	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23007	Horsfieldia glabra	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22242	Phellodendron chinense	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24868	Streptomyces aizunensis	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO16169	Sedum altissimum	Species	Crassulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14337	Ecklonia stolonifera	Species	Lessoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22817	Actinidia valvata	Species	Actinidiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6137	Lepista glaucocana	Species	Tricholomataceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26428	Ligularia sagitta	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21026	Pericopsis mooniana	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24758	Angelica dahurica	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17383	Cyperus nipponicus	Species	Cyperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18680	Larix decidua	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12540	Fuligo septica	Species	Physaraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17360	Argemone albiflora	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29272	Paronychia argentea	Species	Caryophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4790	Bocconia cordata	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25657	Mezzettia leptopoda	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24584	Corydalis bungeana	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO260	Cyclacanthia bellae	Species	Latrunculiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13962	Corydalis turtschaninovii	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13887	Erythrophleum suaveolens	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4574	Eriocephalus giessii	Species	Asteraceae	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	4
Potency	11

Activity Type	# Activity
Individual Protein	10
Organism	3
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT48	Individual Protein	Lysine-specific demethylase 4D-like	Homo sapiens	Potency	=	31622.8	nM	PMID[526700]
NPT210	Individual Protein	Thyroid stimulating hormone receptor	Homo sapiens	Potency	=	12589.3	nM	PMID[526701]
NPT213	Individual Protein	Cytochrome P450 2C19	Homo sapiens	Potency	=	10000.0	nM	PMID[526701]
NPT583	Individual Protein	Inositol monophosphatase 1	Rattus norvegicus	Potency	=	11220.2	nM	PMID[526700]
NPT55	Individual Protein	Putative fructose-1,6-bisphosphate aldolase	Giardia intestinalis	Potency	=	7062.7	nM	PMID[526700]
NPT110	Individual Protein	Cytochrome P450 2D6	Homo sapiens	Potency	=	50.1	nM	PMID[526701]
NPT109	Individual Protein	Cytochrome P450 3A4	Homo sapiens	Potency	=	25118.9	nM	PMID[526700]
NPT204	Individual Protein	Acetylcholinesterase	Homo sapiens	IC50	>	100000.0	nM	PMID[526703]
NPT2	Others	Unspecified		Potency	=	17782.8	nM	PMID[526700]
NPT2	Others	Unspecified		Potency	n.a.	35481.3	nM	PMID[526702]
NPT844	Organism	Trypanosoma brucei rhodesiense	Trypanosoma brucei rhodesiense	IC50	=	8.71	ug.mL-1	PMID[526704]
NPT633	Organism	Leishmania donovani	Leishmania donovani	IC50	>	90.0	ug.mL-1	PMID[526704]
NPT580	Organism	Trypanosoma cruzi	Trypanosoma cruzi	IC50	=	46.27	ug.mL-1	PMID[526704]

☑ 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 NPC308267 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	311
0.1-0.2	1585
0.2-0.3	5349
0.3-0.4	12087
0.4-0.5	4378
0.5-0.6	10382
0.6-0.7	7813
0.7-0.8	714
0.8-0.85	60
0.85-0.9	12
0.9-0.95	1
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.9874	High Similarity	NPC67978
0.9874	High Similarity	NPC303581
0.9748	High Similarity	NPC86469
0.9512	High Similarity	NPC121400
0.9434	High Similarity	NPC153631
0.8663	High Similarity	NPC27887
0.8523	High Similarity	NPC169387
0.8523	High Similarity	NPC477259
0.8483	Intermediate Similarity	NPC226708
0.8409	Intermediate Similarity	NPC116007
0.8409	Intermediate Similarity	NPC83511
0.8407	Intermediate Similarity	NPC207239
0.8344	Intermediate Similarity	NPC470088
0.8278	Intermediate Similarity	NPC63152
0.8253	Intermediate Similarity	NPC470708
0.8251	Intermediate Similarity	NPC73020
0.8251	Intermediate Similarity	NPC14622
0.8251	Intermediate Similarity	NPC46744
0.8251	Intermediate Similarity	NPC124302
0.8251	Intermediate Similarity	NPC215098
0.8251	Intermediate Similarity	NPC70290
0.8242	Intermediate Similarity	NPC119669
0.8242	Intermediate Similarity	NPC477258
0.821	Intermediate Similarity	NPC469978
0.8197	Intermediate Similarity	NPC24228
0.8172	Intermediate Similarity	NPC202771
0.8172	Intermediate Similarity	NPC328700
0.8172	Intermediate Similarity	NPC2173
0.8172	Intermediate Similarity	NPC119818
0.8171	Intermediate Similarity	NPC207721
0.8162	Intermediate Similarity	NPC226652
0.8162	Intermediate Similarity	NPC120671
0.8162	Intermediate Similarity	NPC72788
0.8162	Intermediate Similarity	NPC314100
0.8156	Intermediate Similarity	NPC18306
0.8155	Intermediate Similarity	NPC234392
0.8155	Intermediate Similarity	NPC31311
0.8142	Intermediate Similarity	NPC125924
0.8125	Intermediate Similarity	NPC222524
0.8095	Intermediate Similarity	NPC41178
0.8095	Intermediate Similarity	NPC216459
0.8095	Intermediate Similarity	NPC138487
0.8087	Intermediate Similarity	NPC469816
0.8087	Intermediate Similarity	NPC469815
0.8072	Intermediate Similarity	NPC223125
0.8066	Intermediate Similarity	NPC141440
0.8061	Intermediate Similarity	NPC475959
0.8054	Intermediate Similarity	NPC71124
0.8047	Intermediate Similarity	NPC146288
0.7989	Intermediate Similarity	NPC268077
0.7988	Intermediate Similarity	NPC93593
0.7976	Intermediate Similarity	NPC210148
0.7976	Intermediate Similarity	NPC233029
0.7976	Intermediate Similarity	NPC223124
0.7967	Intermediate Similarity	NPC166979
0.7955	Intermediate Similarity	NPC227683
0.7953	Intermediate Similarity	NPC106786
0.7946	Intermediate Similarity	NPC33256
0.7937	Intermediate Similarity	NPC207971
0.7935	Intermediate Similarity	NPC254957
0.7927	Intermediate Similarity	NPC125134
0.7927	Intermediate Similarity	NPC137920
0.7927	Intermediate Similarity	NPC86455
0.7919	Intermediate Similarity	NPC59567
0.7914	Intermediate Similarity	NPC5374
0.7907	Intermediate Similarity	NPC135006
0.7886	Intermediate Similarity	NPC284842
0.7874	Intermediate Similarity	NPC231198
0.7833	Intermediate Similarity	NPC149285
0.7826	Intermediate Similarity	NPC7018
0.7821	Intermediate Similarity	NPC35680
0.7778	Intermediate Similarity	NPC78733
0.7772	Intermediate Similarity	NPC208890
0.7771	Intermediate Similarity	NPC306669
0.7771	Intermediate Similarity	NPC238530
0.7771	Intermediate Similarity	NPC276944
0.7771	Intermediate Similarity	NPC232514
0.7766	Intermediate Similarity	NPC23080
0.7766	Intermediate Similarity	NPC193906
0.7765	Intermediate Similarity	NPC148898
0.7765	Intermediate Similarity	NPC58661
0.7747	Intermediate Similarity	NPC102760
0.7725	Intermediate Similarity	NPC229787
0.7722	Intermediate Similarity	NPC5167
0.7722	Intermediate Similarity	NPC85613
0.7717	Intermediate Similarity	NPC474009
0.7717	Intermediate Similarity	NPC471650
0.7714	Intermediate Similarity	NPC476569
0.7701	Intermediate Similarity	NPC477559
0.7701	Intermediate Similarity	NPC232924
0.7701	Intermediate Similarity	NPC306902
0.7701	Intermediate Similarity	NPC160298
0.7701	Intermediate Similarity	NPC266753
0.7697	Intermediate Similarity	NPC28398
0.7697	Intermediate Similarity	NPC474708
0.7684	Intermediate Similarity	NPC210918
0.7679	Intermediate Similarity	NPC51957
0.7679	Intermediate Similarity	NPC476144
0.7679	Intermediate Similarity	NPC16107
0.7679	Intermediate Similarity	NPC210437
0.7679	Intermediate Similarity	NPC106295
0.7668	Intermediate Similarity	NPC80472
0.7665	Intermediate Similarity	NPC46880
0.7665	Intermediate Similarity	NPC145304
0.766	Intermediate Similarity	NPC470646
0.7647	Intermediate Similarity	NPC94499
0.7644	Intermediate Similarity	NPC477080
0.764	Intermediate Similarity	NPC475845
0.764	Intermediate Similarity	NPC241055
0.7636	Intermediate Similarity	NPC213206
0.7636	Intermediate Similarity	NPC328750
0.7636	Intermediate Similarity	NPC188163
0.7636	Intermediate Similarity	NPC474915
0.7633	Intermediate Similarity	NPC7467
0.7633	Intermediate Similarity	NPC37144
0.7633	Intermediate Similarity	NPC59907
0.7627	Intermediate Similarity	NPC476432
0.7627	Intermediate Similarity	NPC24264
0.7626	Intermediate Similarity	NPC55470
0.7619	Intermediate Similarity	NPC327052
0.7616	Intermediate Similarity	NPC220577
0.7616	Intermediate Similarity	NPC104353
0.7611	Intermediate Similarity	NPC4669
0.7602	Intermediate Similarity	NPC476579
0.7598	Intermediate Similarity	NPC75958
0.759	Intermediate Similarity	NPC908
0.759	Intermediate Similarity	NPC138438
0.7588	Intermediate Similarity	NPC211296
0.7588	Intermediate Similarity	NPC469539
0.7588	Intermediate Similarity	NPC469540
0.7584	Intermediate Similarity	NPC247389
0.7584	Intermediate Similarity	NPC57812
0.7584	Intermediate Similarity	NPC474324
0.7582	Intermediate Similarity	NPC148693
0.7582	Intermediate Similarity	NPC294790
0.7582	Intermediate Similarity	NPC118633
0.7576	Intermediate Similarity	NPC314682
0.7574	Intermediate Similarity	NPC476151
0.7572	Intermediate Similarity	NPC76079
0.7571	Intermediate Similarity	NPC302527
0.7571	Intermediate Similarity	NPC225774
0.7571	Intermediate Similarity	NPC167546
0.7571	Intermediate Similarity	NPC16805
0.7561	Intermediate Similarity	NPC194359
0.7561	Intermediate Similarity	NPC28641
0.7561	Intermediate Similarity	NPC95366
0.7561	Intermediate Similarity	NPC248505
0.7551	Intermediate Similarity	NPC46990
0.7547	Intermediate Similarity	NPC286683
0.7547	Intermediate Similarity	NPC172403
0.7544	Intermediate Similarity	NPC127827
0.7543	Intermediate Similarity	NPC111485
0.7543	Intermediate Similarity	NPC118804
0.7541	Intermediate Similarity	NPC99723
0.7528	Intermediate Similarity	NPC219341
0.7527	Intermediate Similarity	NPC162694
0.7527	Intermediate Similarity	NPC230098
0.7515	Intermediate Similarity	NPC290404
0.7514	Intermediate Similarity	NPC2314
0.7514	Intermediate Similarity	NPC118332
0.75	Intermediate Similarity	NPC145446
0.75	Intermediate Similarity	NPC89504
0.75	Intermediate Similarity	NPC215829
0.75	Intermediate Similarity	NPC95485
0.75	Intermediate Similarity	NPC474990
0.75	Intermediate Similarity	NPC137172
0.75	Intermediate Similarity	NPC88065
0.75	Intermediate Similarity	NPC37220
0.75	Intermediate Similarity	NPC97072
0.7486	Intermediate Similarity	NPC3273
0.7486	Intermediate Similarity	NPC298979
0.7485	Intermediate Similarity	NPC477565
0.7485	Intermediate Similarity	NPC103379
0.7472	Intermediate Similarity	NPC168409
0.7471	Intermediate Similarity	NPC224687
0.7471	Intermediate Similarity	NPC296575
0.7471	Intermediate Similarity	NPC169742
0.7471	Intermediate Similarity	NPC87295
0.7471	Intermediate Similarity	NPC308555
0.7459	Intermediate Similarity	NPC65403
0.7455	Intermediate Similarity	NPC252107
0.7455	Intermediate Similarity	NPC225745
0.7453	Intermediate Similarity	NPC160193
0.7446	Intermediate Similarity	NPC474745
0.7444	Intermediate Similarity	NPC266176
0.7444	Intermediate Similarity	NPC158148
0.7444	Intermediate Similarity	NPC82533
0.7444	Intermediate Similarity	NPC290759
0.7443	Intermediate Similarity	NPC261484
0.7442	Intermediate Similarity	NPC478189
0.744	Intermediate Similarity	NPC136860
0.744	Intermediate Similarity	NPC476567
0.744	Intermediate Similarity	NPC128019
0.7439	Intermediate Similarity	NPC96406
0.7432	Intermediate Similarity	NPC474470
0.743	Intermediate Similarity	NPC86144
0.743	Intermediate Similarity	NPC304659
0.743	Intermediate Similarity	NPC476002
0.743	Intermediate Similarity	NPC61141
0.7429	Intermediate Similarity	NPC57512

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 NPC308267 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	205
0.1-0.2	769
0.2-0.3	1000
0.3-0.4	2011
0.4-0.5	2615
0.5-0.6	1775
0.6-0.7	674
0.7-0.8	95
0.8-0.85	4
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8434	Intermediate Similarity	NPD5977	Approved
0.8434	Intermediate Similarity	NPD5978	Approved
0.8251	Intermediate Similarity	NPD4420	Approved
0.8172	Intermediate Similarity	NPD5006	Approved
0.8172	Intermediate Similarity	NPD5005	Approved
0.7927	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7824	Intermediate Similarity	NPD6386	Approved
0.7824	Intermediate Similarity	NPD6385	Approved
0.779	Intermediate Similarity	NPD7280	Phase 3
0.779	Intermediate Similarity	NPD7281	Phase 3
0.7706	Intermediate Similarity	NPD824	Approved
0.7692	Intermediate Similarity	NPD3641	Approved
0.7692	Intermediate Similarity	NPD3639	Approved
0.7692	Intermediate Similarity	NPD6662	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD3640	Phase 3
0.7684	Intermediate Similarity	NPD5242	Approved
0.7679	Intermediate Similarity	NPD4584	Approved
0.7661	Intermediate Similarity	NPD1337	Clinical (unspecified phase)
0.7636	Intermediate Similarity	NPD4664	Clinical (unspecified phase)
0.7634	Intermediate Similarity	NPD5525	Clinical (unspecified phase)
0.7616	Intermediate Similarity	NPD6873	Phase 2
0.7558	Intermediate Similarity	NPD6875	Approved
0.7558	Intermediate Similarity	NPD6876	Approved
0.7554	Intermediate Similarity	NPD6618	Phase 2
0.7526	Intermediate Similarity	NPD5564	Approved
0.7514	Intermediate Similarity	NPD7109	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD7110	Phase 1
0.75	Intermediate Similarity	NPD5457	Discontinued
0.75	Intermediate Similarity	NPD4859	Phase 1
0.7486	Intermediate Similarity	NPD5616	Clinical (unspecified phase)
0.7398	Intermediate Similarity	NPD7607	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD7235	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD2492	Phase 1
0.7312	Intermediate Similarity	NPD3534	Clinical (unspecified phase)
0.7289	Intermediate Similarity	NPD743	Approved
0.7283	Intermediate Similarity	NPD1670	Discontinued
0.7283	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7253	Intermediate Similarity	NPD2898	Approved
0.7251	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.7249	Intermediate Similarity	NPD7291	Discontinued
0.7245	Intermediate Similarity	NPD956	Clinical (unspecified phase)
0.724	Intermediate Similarity	NPD4413	Clinical (unspecified phase)
0.7231	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7231	Intermediate Similarity	NPD4107	Approved
0.7228	Intermediate Similarity	NPD5312	Approved
0.7228	Intermediate Similarity	NPD3050	Clinical (unspecified phase)
0.7228	Intermediate Similarity	NPD5313	Approved
0.7219	Intermediate Similarity	NPD2971	Approved
0.7219	Intermediate Similarity	NPD2968	Approved
0.7217	Intermediate Similarity	NPD6625	Approved
0.7207	Intermediate Similarity	NPD8005	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD7667	Clinical (unspecified phase)
0.7158	Intermediate Similarity	NPD6040	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD6297	Approved
0.7135	Intermediate Similarity	NPD7296	Approved
0.712	Intermediate Similarity	NPD6377	Clinical (unspecified phase)
0.711	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD3140	Approved
0.7108	Intermediate Similarity	NPD3142	Approved
0.7107	Intermediate Similarity	NPD4482	Phase 3
0.7102	Intermediate Similarity	NPD4017	Approved
0.7095	Intermediate Similarity	NPD2560	Approved
0.7095	Intermediate Similarity	NPD2563	Approved
0.7088	Intermediate Similarity	NPD6107	Approved
0.7086	Intermediate Similarity	NPD6030	Approved
0.7086	Intermediate Similarity	NPD6031	Approved
0.7083	Intermediate Similarity	NPD6895	Approved
0.7083	Intermediate Similarity	NPD3808	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD6896	Approved
0.7073	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7065	Intermediate Similarity	NPD5950	Discontinued
0.7056	Intermediate Similarity	NPD4947	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD5071	Phase 2
0.7041	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD4846	Phase 2
0.7037	Intermediate Similarity	NPD6146	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD2669	Clinical (unspecified phase)
0.7017	Intermediate Similarity	NPD1309	Phase 2
0.7017	Intermediate Similarity	NPD1307	Phase 2
0.7016	Intermediate Similarity	NPD4084	Clinical (unspecified phase)
0.701	Intermediate Similarity	NPD4466	Phase 1
0.7006	Intermediate Similarity	NPD2649	Approved
0.7006	Intermediate Similarity	NPD2651	Approved
0.7005	Intermediate Similarity	NPD5441	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6851	Approved
0.7	Intermediate Similarity	NPD6853	Approved
0.7	Intermediate Similarity	NPD5353	Approved
0.6995	Remote Similarity	NPD2488	Approved
0.6995	Remote Similarity	NPD2490	Approved
0.699	Remote Similarity	NPD2975	Approved
0.699	Remote Similarity	NPD2974	Approved
0.699	Remote Similarity	NPD2973	Approved
0.6989	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6988	Remote Similarity	NPD5718	Phase 2
0.6985	Remote Similarity	NPD3057	Approved
0.6983	Remote Similarity	NPD7248	Discontinued
0.6983	Remote Similarity	NPD7298	Approved
0.6983	Remote Similarity	NPD6279	Approved
0.6983	Remote Similarity	NPD6280	Approved
0.6977	Remote Similarity	NPD2654	Approved
0.6957	Remote Similarity	NPD4166	Phase 2
0.6957	Remote Similarity	NPD6747	Phase 1
0.6946	Remote Similarity	NPD554	Clinical (unspecified phase)
0.6932	Remote Similarity	NPD3647	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD3863	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD7832	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD7833	Phase 2
0.6923	Remote Similarity	NPD7831	Phase 2
0.6912	Remote Similarity	NPD5914	Approved
0.69	Remote Similarity	NPD2491	Approved
0.69	Remote Similarity	NPD3448	Approved
0.69	Remote Similarity	NPD3533	Approved
0.69	Remote Similarity	NPD2972	Approved
0.6898	Remote Similarity	NPD8251	Approved
0.6898	Remote Similarity	NPD2822	Clinical (unspecified phase)
0.6898	Remote Similarity	NPD8099	Discontinued
0.6898	Remote Similarity	NPD7177	Discontinued
0.6898	Remote Similarity	NPD8252	Approved
0.6895	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6895	Remote Similarity	NPD7190	Clinical (unspecified phase)
0.6893	Remote Similarity	NPD5586	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD6844	Discontinued
0.6889	Remote Similarity	NPD7577	Discontinued
0.6884	Remote Similarity	NPD4580	Approved
0.6884	Remote Similarity	NPD7255	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD4481	Phase 3
0.6882	Remote Similarity	NPD6894	Phase 1
0.6882	Remote Similarity	NPD4575	Clinical (unspecified phase)
0.6878	Remote Similarity	NPD683	Approved
0.6868	Remote Similarity	NPD5019	Clinical (unspecified phase)
0.6868	Remote Similarity	NPD6788	Approved
0.6865	Remote Similarity	NPD6808	Phase 2
0.6865	Remote Similarity	NPD6071	Discontinued
0.6862	Remote Similarity	NPD8156	Discontinued
0.6854	Remote Similarity	NPD4210	Discontinued
0.685	Remote Similarity	NPD2493	Approved
0.685	Remote Similarity	NPD3452	Approved
0.685	Remote Similarity	NPD2494	Approved
0.685	Remote Similarity	NPD3450	Approved
0.6842	Remote Similarity	NPD5192	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD7038	Approved
0.6842	Remote Similarity	NPD7039	Approved
0.684	Remote Similarity	NPD7279	Phase 2
0.684	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.684	Remote Similarity	NPD7278	Phase 2
0.6837	Remote Similarity	NPD6181	Discontinued
0.6833	Remote Similarity	NPD4773	Phase 2
0.6833	Remote Similarity	NPD4772	Phase 2
0.6828	Remote Similarity	NPD8051	Clinical (unspecified phase)
0.6816	Remote Similarity	NPD7261	Clinical (unspecified phase)
0.6816	Remote Similarity	NPD7626	Approved
0.6816	Remote Similarity	NPD7627	Approved
0.6811	Remote Similarity	NPD2821	Approved
0.6811	Remote Similarity	NPD7802	Discontinued
0.6809	Remote Similarity	NPD3818	Discontinued
0.6809	Remote Similarity	NPD2163	Approved
0.6802	Remote Similarity	NPD4476	Approved
0.6802	Remote Similarity	NPD4477	Approved
0.68	Remote Similarity	NPD5241	Discontinued
0.68	Remote Similarity	NPD5307	Clinical (unspecified phase)
0.6798	Remote Similarity	NPD5976	Discontinued
0.6796	Remote Similarity	NPD7317	Phase 3
0.6792	Remote Similarity	NPD6997	Phase 2
0.6791	Remote Similarity	NPD3451	Clinical (unspecified phase)
0.6789	Remote Similarity	NPD3823	Discontinued
0.678	Remote Similarity	NPD1424	Approved
0.6778	Remote Similarity	NPD7028	Phase 2
0.6774	Remote Similarity	NPD5183	Approved
0.6774	Remote Similarity	NPD5186	Approved
0.6763	Remote Similarity	NPD7827	Phase 1
0.6761	Remote Similarity	NPD7124	Phase 2
0.6758	Remote Similarity	NPD4585	Approved
0.6758	Remote Similarity	NPD2977	Approved
0.6758	Remote Similarity	NPD2978	Approved
0.6757	Remote Similarity	NPD5494	Approved
0.6757	Remote Similarity	NPD7201	Clinical (unspecified phase)
0.6755	Remote Similarity	NPD3446	Phase 1
0.675	Remote Similarity	NPD5536	Phase 2
0.6749	Remote Similarity	NPD4582	Approved
0.6749	Remote Similarity	NPD4583	Approved
0.6746	Remote Similarity	NPD4475	Approved
0.6746	Remote Similarity	NPD4474	Approved
0.6737	Remote Similarity	NPD3885	Approved
0.6727	Remote Similarity	NPD1876	Approved
0.6725	Remote Similarity	NPD2653	Approved
0.6724	Remote Similarity	NPD3655	Clinical (unspecified phase)
0.6722	Remote Similarity	NPD7458	Discontinued
0.6721	Remote Similarity	NPD7318	Phase 3
0.672	Remote Similarity	NPD7199	Phase 2
0.6718	Remote Similarity	NPD3349	Phase 2
0.6718	Remote Similarity	NPD7693	Approved
0.6717	Remote Similarity	NPD3473	Clinical (unspecified phase)
0.6715	Remote Similarity	NPD5676	Approved
0.6714	Remote Similarity	NPD5980	Discovery
0.6707	Remote Similarity	NPD3972	Approved
0.6704	Remote Similarity	NPD7427	Discontinued
0.6704	Remote Similarity	NPD1914	Approved
0.67	Remote Similarity	NPD4002	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