NPASS Compound

Structure

CID257191 OpenBabel06191716062D 32 36 0 0 1 0 0 0 0 0999 V2000 4.3963 -5.4234 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0028 -4.9010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8849 -3.1634 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6913 2.9607 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5645 2.4564 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6917 -1.9838 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6908 1.0090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4914 -2.6410 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7930 -3.5685 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0006 1.9526 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8451 1.4647 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3813 -0.9748 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5356 0.4874 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3810 0.0010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6905 -0.0005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8460 -1.4636 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0003 -0.9757 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8454 -0.4884 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0488 -4.6985 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5373 -2.4385 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5370 -1.4631 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.7471 -3.7710 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8460 1.4642 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8454 0.4884 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5359 1.4637 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6911 1.9521 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6914 -0.9752 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6911 0.0005 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8457 0.4879 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.3995 -3.0460 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4021 1.9634 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 19 2 0 0 0 0 2 19 1 0 0 0 0 4 26 1 0 0 0 0 5 26 1 0 0 0 0 6 27 1 0 0 0 0 8 9 1 0 0 0 0 8 20 1 0 0 0 0 9 22 1 0 0 0 0 10 11 1 0 0 0 0 10 23 1 0 0 0 0 11 24 1 0 0 0 0 12 14 1 0 0 0 0 12 21 1 0 0 0 0 13 15 1 0 0 0 0 13 25 1 0 0 0 0 14 28 1 0 0 0 0 15 29 1 0 0 0 0 16 17 1 0 0 0 0 16 27 1 0 0 0 0 18 29 1 0 0 0 0 18 30 1 0 0 0 0 19 22 1 0 0 0 0 20 3 1 1 0 0 0 20 21 1 0 0 0 0 21 27 1 6 0 0 0 22 31 1 1 0 0 0 23 26 1 0 0 0 0 23 29 1 6 0 0 0 24 28 1 1 0 0 0 24 30 1 0 0 0 0 25 26 1 0 0 0 0 25 32 1 6 0 0 0 27 28 1 6 0 0 0 28 7 1 1 0 0 0 29 30 1 1 0 0 0 30 17 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	442.38
Volume:	499.598
LogP:	6.504
LogD:	5.131
LogS:	-5.533
# Rotatable Bonds:	5
TPSA:	40.46
# H-Bond Aceptor:	2
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.444
Synthetic Accessibility Score:	5.572
Fsp3:	0.933
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.026
MDCK Permeability:	1.4189841749612242e-05
Pgp-inhibitor:	0.137
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.944
30% Bioavailability (F30%):	0.973

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.127
Plasma Protein Binding (PPB):	95.89183807373047%
Volume Distribution (VD):	1.226
Pgp-substrate:	1.9309738874435425%

ADMET: Metabolism

CYP1A2-inhibitor:	0.027
CYP1A2-substrate:	0.278
CYP2C19-inhibitor:	0.06
CYP2C19-substrate:	0.932
CYP2C9-inhibitor:	0.22
CYP2C9-substrate:	0.334
CYP2D6-inhibitor:	0.023
CYP2D6-substrate:	0.641
CYP3A4-inhibitor:	0.799
CYP3A4-substrate:	0.627

ADMET: Excretion

Clearance (CL):	6.596
Half-life (T1/2):	0.081

ADMET: Toxicity

hERG Blockers:	0.46
Human Hepatotoxicity (H-HT):	0.313
Drug-inuced Liver Injury (DILI):	0.032
AMES Toxicity:	0.003
Rat Oral Acute Toxicity:	0.862
Maximum Recommended Daily Dose:	0.975
Skin Sensitization:	0.943
Carcinogencity:	0.058
Eye Corrosion:	0.668
Eye Irritation:	0.284
Respiratory Toxicity:	0.891

Download Data

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

Natural Product: NPC257191

Natural Product ID:	NPC257191
*Common Name:**	MHGLNDDJLDJDBG-BBEZHFTESA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	MHGLNDDJLDJDBG-BBEZHFTESA-N
Standard InCHI:	InChI=1S/C30H50O2/c1-19(2)22(31)9-8-20(3)21-12-14-28(7)24-11-10-23-26(4,5)25(32)13-15-29(23)18-30(24,29)17-16-27(21,28)6/h20-25,31-32H,1,8-18H2,2-7H3/t20-,21-,22-,23+,24+,25+,27-,28+,29-,30+/m1/s1
SMILES:	CC(=C)[C@@H](CC[C@H]([C@H]1CC[C@@]2([C@]1(C)CC[C@@]13[C@H]2CC[C@@H]2[C@]3(C1)CC[C@@H](C2(C)C)O)C)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL225870
PubChem CID:	14313591
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0002321] Cycloartanols and derivatives

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

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO19965	Helenium alternifolium	Species	Asteraceae	Eukaryota	n.a.	aerial part	n.a.	DOI[10.1021/jo01271a036]
NPO26629	Caesalpinia pulcherrima	Species	Fabaceae	Eukaryota	n.a.	stem	n.a.	DOI[10.1021/np0201523]
NPO29314	Mangifera indica	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1246/bcsj.30.618]
NPO21850	Paeonia delavayi	Species	Paeoniaceae	Eukaryota	n.a.	root	n.a.	PMID[10945272]
NPO26629	Caesalpinia pulcherrima	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12193012]
NPO23006	Moringa stenopetala	Species	Moringaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12709911]
NPO29276	Juglans nigra	Species	Juglandaceae	Eukaryota	n.a.	root	n.a.	PMID[14727919]
NPO29276	Juglans nigra	Species	Juglandaceae	Eukaryota	n.a.	bark	n.a.	PMID[14727919]
NPO29276	Juglans nigra	Species	Juglandaceae	Eukaryota	n.a.	xylem	n.a.	PMID[14727919]
NPO29276	Juglans nigra	Species	Juglandaceae	Eukaryota	n.a.	leaf	n.a.	PMID[14727919]
NPO22820	Sarcophyton glaucum	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[15332846]
NPO29530	Kaempferia marginata	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16309313]
NPO22820	Sarcophyton glaucum	Species	Alcyoniidae	Eukaryota	n.a.	Amami Oshima, Kagoshima Prefecture, Japan	n.a.	PMID[16933862]
NPO27743	Aaptos aaptos	Species	Suberitidae	Eukaryota	n.a.	n.a.	n.a.	PMID[17716892]
NPO28864	Nauclea officinalis	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19299148]
NPO26661	Heimia salicifolia	Species	Lythraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19299148]
NPO29381	Trichilia rubescens	Species	Meliaceae	Eukaryota	leaves	Kibale National Park, Uganda	2000-2001	PMID[19299148]
NPO22820	Sarcophyton glaucum	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[19331379]
NPO22820	Sarcophyton glaucum	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[21563811]
NPO20835	Medicago truncatula	Species	Fabaceae	Eukaryota	n.a.	root	n.a.	PMID[21615146]
NPO21278	Lysimachia clethroides	Species	Primulaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[21928797]
NPO21850	Paeonia delavayi	Species	Paeoniaceae	Eukaryota	n.a.	seed	n.a.	PMID[23497864]
NPO27743	Aaptos aaptos	Species	Suberitidae	Eukaryota	n.a.	South China Sea	n.a.	PMID[25211032]
NPO29314	Mangifera indica	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27466882]
NPO22372	Callicarpa bodinieri	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[29578342]
NPO40126	Euphorbia pedroi	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[30199257]
NPO4055	Aspergillus unguis	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31117521]
NPO29530	Kaempferia marginata	Species	Zingiberaceae	Eukaryota	Rhizomes	n.a.	n.a.	PMID[31873014]
NPO26629	Caesalpinia pulcherrima	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[3783154]
NPO14240	Justicia ghiesbreghtiana	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9748395]
NPO29276	Juglans nigra	Species	Juglandaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO12807	Citrus aurantiifolia	Species	Rutaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO29314	Mangifera indica	Species	Anacardiaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO29276	Juglans nigra	Species	Juglandaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO29314	Mangifera indica	Species	Anacardiaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO29276	Juglans nigra	Species	Juglandaceae	Eukaryota	Pericarp	n.a.	n.a.	Database[FooDB]
NPO12807	Citrus aurantiifolia	Species	Rutaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO29276	Juglans nigra	Species	Juglandaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO29314	Mangifera indica	Species	Anacardiaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO29276	Juglans nigra	Species	Juglandaceae	Eukaryota	Shoot	n.a.	n.a.	Database[FooDB]
NPO12807	Citrus aurantiifolia	Species	Rutaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO29314	Mangifera indica	Species	Anacardiaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO29276	Juglans nigra	Species	Juglandaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO12807	Citrus aurantiifolia	Species	Rutaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO29314	Mangifera indica	Species	Anacardiaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO29276	Juglans nigra	Species	Juglandaceae	Eukaryota	Essential Oil	n.a.	n.a.	Database[FooDB]
NPO29314	Mangifera indica	Species	Anacardiaceae	Eukaryota	Flower	n.a.	n.a.	Database[FooDB]
NPO29314	Mangifera indica	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO819	Heliotropium olgae	Species	Heliotropiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28864	Nauclea officinalis	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26629	Caesalpinia pulcherrima	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29004	Ruta pinnata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21850	Paeonia delavayi	Species	Paeoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21221	Trapa bispinosa	Species	Lythraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29276	Juglans nigra	Species	Juglandaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28949	Croton cumingii	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21343	Eupatorium fortunei	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12807	Citrus aurantiifolia	Species	Rutaceae	Eukaryota	Fruits	n.a.		Database[Phenol-Explorer]
NPO12807	Citrus aurantiifolia	Species	Rutaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO29314	Mangifera indica	Species	Anacardiaceae	Eukaryota	Fruits	n.a.		Database[Phenol-Explorer]
NPO29530	Kaempferia marginata	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28949	Croton cumingii	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21850	Paeonia delavayi	Species	Paeoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4055	Aspergillus unguis	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21413	Armillaria tabescens	Species	Physalacriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28805	Thymus piperella	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29004	Ruta pinnata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12807	Citrus aurantiifolia	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29314	Mangifera indica	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21343	Eupatorium fortunei	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26172	Dryopteris sacrosancta	Species	Dryopteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15478	Senna sophera	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22438	Asclepias speciosa	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21221	Trapa bispinosa	Species	Lythraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21278	Lysimachia clethroides	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29344	Parabenzoin trilobum	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TCMID]
NPO28864	Nauclea officinalis	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO819	Heliotropium olgae	Species	Heliotropiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29276	Juglans nigra	Species	Juglandaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26629	Caesalpinia pulcherrima	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15763	Huperzia lucidula	Species	Lycopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29314	Mangifera indica	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO21221	Trapa bispinosa	Species	Lythraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO21343	Eupatorium fortunei	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO28864	Nauclea officinalis	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO29276	Juglans nigra	Species	Juglandaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO17030	Calvatia lilacina	Species	Lycoperdaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO28864	Nauclea officinalis	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2591	Io fluvialis	Species	Pleuroceridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26888	Narcissus asturiensis	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4055	Aspergillus unguis	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29292	Teucrium depressum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2480	Amoora rohituka	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO29127	Cystophora scalaris	Species	Sargassaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28805	Thymus piperella	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26906	Astragalus interpositus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18123	Dichapetalum madagascariense	Species	Dichapetalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4283	Tripteris vaillantii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23695	Setosphaeria turcica	Species	Pleosporaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22372	Callicarpa bodinieri	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27929	Aphanamixis polystachya	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29381	Trichilia rubescens	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28937	Heterotheca grandiflora	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15763	Huperzia lucidula	Species	Lycopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20771	Thalictrum fortunei	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9524	Kalanchoe blossfeldiana	Species	Crassulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21413	Armillaria tabescens	Species	Physalacriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13818	Narcissus concolor	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20203	Syringa komarowi	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29068	Papilio phorcas	Species	Papilionidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28898	Grewia mollis	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22048	Pteris palmiformis	Species	Pteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17373.1	Cunninghamia lanceolata var. konishii	Varieties	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21221	Trapa bispinosa	Species	Lythraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7674	Tragopogon orientalis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26172	Dryopteris sacrosancta	Species	Dryopteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21725	Uncaria glabrata	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9750	Dysoxylum malabaricum	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27489	Alloascoidea hylecoeti	Species	Alloascoideaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20896	Mimosa tenuiflora	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29400	Conocephalum japonicum	Species	Conocephalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28845	Eragrostis viscosa	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17707	Dioscorea villosa	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27269	Annona impressivenia	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21599	Ricciocarpos natans	Species	Ricciaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20967	Doriopsilla albopunctata	Species	Dendrodorididae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17030	Calvatia lilacina	Species	Lycoperdaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29242	Salvia dorrii	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29189	Castanopsis sclerophylla	Species	Fagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26383	Lemna trisulca	Species	Araceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13409	Crocus asturicus	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26839	Microlepia speluncae	Species	Dennstaedtiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29415	Hovenia acerba	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20835	Medicago truncatula	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28784	Alseodaphne corneri	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3446	Acanthaster planci	Species	Acanthasteridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22887	Scutellaria violacea	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29446	Stevia polycephala	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23006	Moringa stenopetala	Species	Moringaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19965	Helenium alternifolium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26931	Dolichothele uberiformis	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO27743	Aaptos aaptos	Species	Suberitidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29488	Sophora angustifolia	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16377	Juniperus ashei	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29225	Oncoba echinata	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20583	Phaulopsis imbricata	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28824	Forsteronia refracta	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29203	Gymnocarpium robertianum	Species	Cystopteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29344	Parabenzoin trilobum	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO26190	Aspergillus wentii	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28949	Croton cumingii	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20088	Piper sintenense	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20522	Pyura sacciformis	Species	Pyuridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4668	Sideritis flavovirens	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29004	Ruta pinnata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21295	Botryotrichum piluliferum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29314	Mangifera indica	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22113	Anthocercis genistoides	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26215	Eleusine indica	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29363	Aconitum nevadense	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25981	Crinipellis scabella	Species	Marasmiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21654	Cyerce cristallina	Species	Caliphyllidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14240	Justicia ghiesbreghtiana	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26411	Stemphylium radicinum	Species	Pleosporaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12807	Citrus aurantiifolia	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7856	Streptomyces halstedii	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO21343	Eupatorium fortunei	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18768	Haliclona tubifera	Species	Chalinidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO819	Heliotropium olgae	Species	Heliotropiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26433	Conus marmoreus	Species	Conidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3990	Acacia salicina	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16254	Backhousia angustifolia	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15966	Sassafras officinalis	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29510	Aulacocephalus temmincki	Species	Serranidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26661	Heimia salicifolia	Species	Lythraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29450	Streptomyces parvisporogenes	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO4244	Doodia picta	Species	Blechnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21665.1	Mycobacterium avium subsp. paratuberculosis	Subspecies	Mycobacteriaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO26192	Cordylanthus kingii	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21278	Lysimachia clethroides	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20261	Teucrium trifidum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13182	Achillea wilhelmsii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28918	Ophiolepis superba	Species	Ophiolepididae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26568	Rubus koehneanus	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3340	Fridericia chica	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29142	Kaunia saltensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22698	Achillea pannonica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10438	Tanacetum nubigenum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29047	Disynaphia halimifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22756	Epimedium versicolor	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22438	Asclepias speciosa	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26325	Annulusmagnus triseptatus	Species	Annulatascaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22308	Stevia satureiaefolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29530	Kaempferia marginata	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3744	Polycephalomyces nipponicus	Species	Ophiocordycipitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4478	Parmelia pseudoreticulata	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15478	Senna sophera	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21032	Manilkara hexandra	Species	Sapotaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25876	Chromodoris inornata	Species	Chromodorididae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18031	Russula vesca	Species	Russulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4372	Halimium halimifolium	Species	Cistaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2633	Baccharis minutiflora	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20021	Physcia aegialita	Species	Physciaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9157	Rubrivivax gelatinosus	Species	n.a.	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO20457	Spirastrella inconstans	Species	Spirastrellidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29276	Juglans nigra	Species	Juglandaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8115	Polyopes affinis	Species	Halymeniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29041	Scutellaria orientalis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22953	Eupatorium pauciflorum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21850	Paeonia delavayi	Species	Paeoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22499	Corydalis flabellata	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22820	Sarcophyton glaucum	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21089	Mourera fluviatilis	Species	Podostemaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20381	Echites hirsuta	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19891	Diospyros crassiflora	Species	Ebenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28971	Bersama yangambiensis	Species	Melianthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29154	Heliotropium floridum	Species	Heliotropiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20707	Stillingia sanguinolenta	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21158	Viburnum fur	Species	Adoxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1245	Eunicella cavolinii	Species	Gorgoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28103	Erica carnea	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6746	Blighia welwitschii	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26629	Caesalpinia pulcherrima	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

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

NP Quantity Composition/Concentration

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

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

Biological Activity

Activity Type	# Activity
IC50	7
Others	10

Activity Type	# Activity
Cell Line	7
Individual Protein	4
Organism	5
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT80	Cell Line	Raji	Homo sapiens	Activity	=	70.0	%	PMID[496354]
NPT171	Cell Line	MRC5	Homo sapiens	IC50	>	10000.0	nM	PMID[496355]
NPT886	Cell Line	NIH3T3	Mus musculus	IC50	>	10000.0	nM	PMID[496355]
NPT407	Cell Line	COLO 205	Homo sapiens	IC50	>	10000.0	nM	PMID[496355]
NPT2641	Cell Line	COLO 320	Homo sapiens	IC50	>	10000.0	nM	PMID[496355]
NPT1864	Cell Line	L5178Y	Mus musculus	IC50	>	10000.0	nM	PMID[496355]
NPT164	Organism	Human herpesvirus 4	Human herpesvirus 4	Inhibition	=	0.0	%	PMID[496354]
NPT164	Organism	Human herpesvirus 4	Human herpesvirus 4	Inhibition	=	15.0	%	PMID[496354]
NPT164	Organism	Human herpesvirus 4	Human herpesvirus 4	Inhibition	=	57.8	%	PMID[496354]
NPT164	Organism	Human herpesvirus 4	Human herpesvirus 4	Inhibition	=	84.4	%	PMID[496354]
NPT164	Organism	Human herpesvirus 4	Human herpesvirus 4	IC50	=	6.4	nM	PMID[496354]
NPT2	Others	Unspecified		Activity	=	2.0	n.a.	PMID[496354]
NPT668	Individual Protein	P-glycoprotein 1	Homo sapiens	Ratio	=	5.91	n.a.	PMID[496355]
NPT668	Individual Protein	P-glycoprotein 1	Homo sapiens	Ratio	=	43.58	n.a.	PMID[496355]
NPT668	Individual Protein	P-glycoprotein 1	Homo sapiens	Ratio	=	0.77	n.a.	PMID[496355]

☑ 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 NPC257191 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	171
0.1-0.2	2144
0.2-0.3	10550
0.3-0.4	14503
0.4-0.5	5611
0.5-0.6	5427
0.6-0.7	3172
0.7-0.8	916
0.8-0.85	113
0.85-0.9	64
0.9-0.95	16
0.95-1	10

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC331618
0.9861	High Similarity	NPC472342
0.9718	High Similarity	NPC70982
0.9718	High Similarity	NPC185536
0.9718	High Similarity	NPC230704
0.9577	High Similarity	NPC254509
0.9577	High Similarity	NPC5046
0.9577	High Similarity	NPC49168
0.9577	High Similarity	NPC196358
0.9577	High Similarity	NPC145552
0.9452	High Similarity	NPC212241
0.9452	High Similarity	NPC119355
0.9452	High Similarity	NPC248830
0.9444	High Similarity	NPC200243
0.9437	High Similarity	NPC195489
0.9324	High Similarity	NPC301707
0.9296	High Similarity	NPC111234
0.9189	High Similarity	NPC260301
0.9189	High Similarity	NPC307336
0.9189	High Similarity	NPC138502
0.9178	High Similarity	NPC240235
0.9178	High Similarity	NPC3403
0.9178	High Similarity	NPC231256
0.9178	High Similarity	NPC178383
0.9178	High Similarity	NPC212879
0.9178	High Similarity	NPC104387
0.9155	High Similarity	NPC45296
0.9067	High Similarity	NPC85346
0.9067	High Similarity	NPC472501
0.9067	High Similarity	NPC472500
0.9067	High Similarity	NPC65897
0.9067	High Similarity	NPC302041
0.9067	High Similarity	NPC472499
0.9054	High Similarity	NPC278091
0.9054	High Similarity	NPC14112
0.9054	High Similarity	NPC91573
0.9054	High Similarity	NPC38141
0.9054	High Similarity	NPC93662
0.9054	High Similarity	NPC78067
0.9054	High Similarity	NPC86305
0.9041	High Similarity	NPC308440
0.9041	High Similarity	NPC25511
0.9041	High Similarity	NPC476736
0.9041	High Similarity	NPC62657
0.9041	High Similarity	NPC192638
0.9041	High Similarity	NPC472503
0.8974	High Similarity	NPC82623
0.8947	High Similarity	NPC24504
0.8947	High Similarity	NPC476316
0.8933	High Similarity	NPC202540
0.8904	High Similarity	NPC472506
0.8846	High Similarity	NPC296701
0.8846	High Similarity	NPC218616
0.8831	High Similarity	NPC47149
0.8816	High Similarity	NPC312328
0.8816	High Similarity	NPC472502
0.8816	High Similarity	NPC31828
0.8816	High Similarity	NPC167037
0.8816	High Similarity	NPC102708
0.8816	High Similarity	NPC6978
0.8816	High Similarity	NPC475
0.8816	High Similarity	NPC42853
0.8816	High Similarity	NPC138621
0.8816	High Similarity	NPC244385
0.8816	High Similarity	NPC477817
0.8816	High Similarity	NPC285761
0.8816	High Similarity	NPC477819
0.88	High Similarity	NPC237460
0.8767	High Similarity	NPC164045
0.8734	High Similarity	NPC113978
0.8734	High Similarity	NPC134481
0.8718	High Similarity	NPC157655
0.8701	High Similarity	NPC80297
0.8701	High Similarity	NPC273410
0.8701	High Similarity	NPC49599
0.8701	High Similarity	NPC30986
0.8701	High Similarity	NPC209430
0.8701	High Similarity	NPC472742
0.8701	High Similarity	NPC49627
0.8701	High Similarity	NPC475727
0.8701	High Similarity	NPC5604
0.8701	High Similarity	NPC80530
0.8701	High Similarity	NPC116119
0.8667	High Similarity	NPC144075
0.8667	High Similarity	NPC103822
0.8659	High Similarity	NPC67872
0.8608	High Similarity	NPC477858
0.859	High Similarity	NPC102253
0.859	High Similarity	NPC13554
0.859	High Similarity	NPC78545
0.859	High Similarity	NPC322313
0.859	High Similarity	NPC236237
0.859	High Similarity	NPC475679
0.859	High Similarity	NPC71535
0.8571	High Similarity	NPC474216
0.8553	High Similarity	NPC73875
0.8553	High Similarity	NPC189883
0.8533	High Similarity	NPC469534
0.8533	High Similarity	NPC469593
0.8533	High Similarity	NPC469533
0.8519	High Similarity	NPC76518
0.8519	High Similarity	NPC292553
0.8472	Intermediate Similarity	NPC475884
0.8472	Intermediate Similarity	NPC473230
0.8462	Intermediate Similarity	NPC84694
0.8462	Intermediate Similarity	NPC109546
0.8462	Intermediate Similarity	NPC1319
0.8462	Intermediate Similarity	NPC81306
0.8462	Intermediate Similarity	NPC143182
0.8462	Intermediate Similarity	NPC28862
0.8462	Intermediate Similarity	NPC47982
0.8451	Intermediate Similarity	NPC27243
0.8451	Intermediate Similarity	NPC473276
0.8451	Intermediate Similarity	NPC41577
0.8451	Intermediate Similarity	NPC476737
0.8451	Intermediate Similarity	NPC474380
0.8442	Intermediate Similarity	NPC34019
0.8442	Intermediate Similarity	NPC470758
0.8442	Intermediate Similarity	NPC214570
0.8442	Intermediate Similarity	NPC470711
0.8421	Intermediate Similarity	NPC322353
0.8421	Intermediate Similarity	NPC257347
0.8421	Intermediate Similarity	NPC471723
0.8421	Intermediate Similarity	NPC118508
0.8421	Intermediate Similarity	NPC121744
0.8421	Intermediate Similarity	NPC141071
0.8415	Intermediate Similarity	NPC472738
0.8415	Intermediate Similarity	NPC168231
0.8415	Intermediate Similarity	NPC269058
0.8415	Intermediate Similarity	NPC71520
0.84	Intermediate Similarity	NPC211009
0.8395	Intermediate Similarity	NPC256567
0.8395	Intermediate Similarity	NPC86238
0.8395	Intermediate Similarity	NPC474047
0.8375	Intermediate Similarity	NPC49964
0.8375	Intermediate Similarity	NPC470049
0.8375	Intermediate Similarity	NPC87489
0.8375	Intermediate Similarity	NPC101462
0.8375	Intermediate Similarity	NPC477599
0.8375	Intermediate Similarity	NPC202389
0.8354	Intermediate Similarity	NPC241290
0.8354	Intermediate Similarity	NPC236112
0.8354	Intermediate Similarity	NPC234193
0.8354	Intermediate Similarity	NPC206735
0.8354	Intermediate Similarity	NPC164840
0.8354	Intermediate Similarity	NPC209944
0.8353	Intermediate Similarity	NPC110923
0.8353	Intermediate Similarity	NPC74296
0.8333	Intermediate Similarity	NPC11908
0.8333	Intermediate Similarity	NPC275910
0.8333	Intermediate Similarity	NPC473943
0.8313	Intermediate Similarity	NPC4643
0.8313	Intermediate Similarity	NPC89747
0.8312	Intermediate Similarity	NPC129165
0.8312	Intermediate Similarity	NPC240604
0.8312	Intermediate Similarity	NPC321016
0.8312	Intermediate Similarity	NPC107059
0.8312	Intermediate Similarity	NPC202642
0.8312	Intermediate Similarity	NPC300324
0.8312	Intermediate Similarity	NPC247325
0.8312	Intermediate Similarity	NPC470749
0.8312	Intermediate Similarity	NPC46160
0.8312	Intermediate Similarity	NPC321381
0.8312	Intermediate Similarity	NPC244488
0.8312	Intermediate Similarity	NPC134330
0.831	Intermediate Similarity	NPC69149
0.831	Intermediate Similarity	NPC68656
0.8293	Intermediate Similarity	NPC22133
0.8272	Intermediate Similarity	NPC477818
0.8272	Intermediate Similarity	NPC246956
0.8272	Intermediate Similarity	NPC232023
0.8272	Intermediate Similarity	NPC475726
0.8272	Intermediate Similarity	NPC207013
0.8272	Intermediate Similarity	NPC470558
0.8272	Intermediate Similarity	NPC216420
0.8272	Intermediate Similarity	NPC110778
0.8272	Intermediate Similarity	NPC85095
0.8272	Intermediate Similarity	NPC470929
0.8272	Intermediate Similarity	NPC317458
0.8272	Intermediate Similarity	NPC211135
0.8272	Intermediate Similarity	NPC5280
0.8272	Intermediate Similarity	NPC472743
0.8272	Intermediate Similarity	NPC475789
0.8267	Intermediate Similarity	NPC301226
0.8256	Intermediate Similarity	NPC476304
0.825	Intermediate Similarity	NPC264245
0.825	Intermediate Similarity	NPC23852
0.825	Intermediate Similarity	NPC209620
0.825	Intermediate Similarity	NPC474531
0.8243	Intermediate Similarity	NPC241085
0.8243	Intermediate Similarity	NPC470830
0.8243	Intermediate Similarity	NPC9942
0.8243	Intermediate Similarity	NPC299948
0.8243	Intermediate Similarity	NPC210323
0.8228	Intermediate Similarity	NPC47808
0.8228	Intermediate Similarity	NPC472463
0.8214	Intermediate Similarity	NPC16377
0.8214	Intermediate Similarity	NPC146937
0.8205	Intermediate Similarity	NPC198968
0.8205	Intermediate Similarity	NPC318495

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 NPC257191 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	169
0.1-0.2	2448
0.2-0.3	4429
0.3-0.4	1500
0.4-0.5	244
0.5-0.6	169
0.6-0.7	147
0.7-0.8	43
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.859	High Similarity	NPD7525	Registered
0.8182	Intermediate Similarity	NPD6942	Approved
0.8182	Intermediate Similarity	NPD7339	Approved
0.8072	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7848	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD7645	Phase 2
0.7763	Intermediate Similarity	NPD4267	Clinical (unspecified phase)
0.7595	Intermediate Similarity	NPD6924	Approved
0.7595	Intermediate Similarity	NPD6926	Approved
0.7561	Intermediate Similarity	NPD6929	Approved
0.7529	Intermediate Similarity	NPD4786	Approved
0.75	Intermediate Similarity	NPD5328	Approved
0.7471	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.747	Intermediate Similarity	NPD6930	Phase 2
0.747	Intermediate Similarity	NPD6931	Approved
0.7436	Intermediate Similarity	NPD4787	Phase 1
0.7412	Intermediate Similarity	NPD4788	Approved
0.7407	Intermediate Similarity	NPD6933	Approved
0.7381	Intermediate Similarity	NPD6902	Approved
0.7356	Intermediate Similarity	NPD3618	Phase 1
0.7342	Intermediate Similarity	NPD7150	Approved
0.7342	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.7342	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.7342	Intermediate Similarity	NPD7151	Approved
0.7342	Intermediate Similarity	NPD4243	Approved
0.7342	Intermediate Similarity	NPD7152	Approved
0.7333	Intermediate Similarity	NPD6079	Approved
0.7333	Intermediate Similarity	NPD8034	Phase 2
0.7333	Intermediate Similarity	NPD8035	Phase 2
0.7317	Intermediate Similarity	NPD5776	Phase 2
0.7317	Intermediate Similarity	NPD6925	Approved
0.7308	Intermediate Similarity	NPD6922	Approved
0.7308	Intermediate Similarity	NPD6923	Approved
0.7294	Intermediate Similarity	NPD3667	Approved
0.7262	Intermediate Similarity	NPD4748	Discontinued
0.7229	Intermediate Similarity	NPD7145	Approved
0.7215	Intermediate Similarity	NPD7143	Approved
0.7215	Intermediate Similarity	NPD7144	Approved
0.7209	Intermediate Similarity	NPD6695	Phase 3
0.7195	Intermediate Similarity	NPD6117	Approved
0.716	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD4784	Approved
0.716	Intermediate Similarity	NPD4785	Approved
0.7158	Intermediate Similarity	NPD7640	Approved
0.7158	Intermediate Similarity	NPD7639	Approved
0.7126	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD6116	Phase 1
0.7089	Intermediate Similarity	NPD3700	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD3699	Clinical (unspecified phase)
0.7065	Intermediate Similarity	NPD4202	Approved
0.7059	Intermediate Similarity	NPD7509	Discontinued
0.7059	Intermediate Similarity	NPD7514	Phase 3
0.7053	Intermediate Similarity	NPD7638	Approved
0.7045	Intermediate Similarity	NPD6893	Approved
0.7024	Intermediate Similarity	NPD7322	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD6118	Approved
0.7024	Intermediate Similarity	NPD6114	Approved
0.7024	Intermediate Similarity	NPD6115	Approved
0.7024	Intermediate Similarity	NPD6697	Approved
0.6932	Remote Similarity	NPD3665	Phase 1
0.6932	Remote Similarity	NPD3666	Approved
0.6932	Remote Similarity	NPD3133	Approved
0.6905	Remote Similarity	NPD6932	Approved
0.6889	Remote Similarity	NPD7524	Approved
0.6889	Remote Similarity	NPD7750	Discontinued
0.6867	Remote Similarity	NPD4190	Phase 3
0.6867	Remote Similarity	NPD8264	Approved
0.6867	Remote Similarity	NPD5275	Approved
0.6867	Remote Similarity	NPD3703	Phase 2
0.686	Remote Similarity	NPD7332	Phase 2
0.6842	Remote Similarity	NPD5221	Approved
0.6842	Remote Similarity	NPD4697	Phase 3
0.6842	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD5222	Approved
0.6837	Remote Similarity	NPD5211	Phase 2
0.679	Remote Similarity	NPD4245	Approved
0.679	Remote Similarity	NPD4244	Approved
0.679	Remote Similarity	NPD4789	Approved
0.6782	Remote Similarity	NPD6898	Phase 1
0.6774	Remote Similarity	NPD7515	Phase 2
0.6771	Remote Similarity	NPD4755	Approved
0.6771	Remote Similarity	NPD5173	Approved
0.675	Remote Similarity	NPD5360	Phase 3
0.675	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.6744	Remote Similarity	NPD4195	Approved
0.6744	Remote Similarity	NPD6683	Phase 2
0.6702	Remote Similarity	NPD6399	Phase 3
0.67	Remote Similarity	NPD5141	Approved
0.6667	Remote Similarity	NPD7632	Discontinued
0.6667	Remote Similarity	NPD3698	Phase 2
0.6667	Remote Similarity	NPD6928	Phase 2
0.6633	Remote Similarity	NPD4696	Approved
0.6633	Remote Similarity	NPD5286	Approved
0.6633	Remote Similarity	NPD4700	Approved
0.6633	Remote Similarity	NPD5285	Approved
0.6596	Remote Similarity	NPD7087	Discontinued
0.6593	Remote Similarity	NPD5279	Phase 3
0.6582	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.6566	Remote Similarity	NPD5223	Approved
0.6559	Remote Similarity	NPD4753	Phase 2
0.6556	Remote Similarity	NPD3668	Phase 3
0.6531	Remote Similarity	NPD5290	Discontinued
0.6517	Remote Similarity	NPD4221	Approved
0.6517	Remote Similarity	NPD4223	Phase 3
0.65	Remote Similarity	NPD5225	Approved
0.65	Remote Similarity	NPD5226	Approved
0.65	Remote Similarity	NPD4633	Approved
0.65	Remote Similarity	NPD5224	Approved
0.6484	Remote Similarity	NPD5329	Approved
0.6471	Remote Similarity	NPD5739	Approved
0.6471	Remote Similarity	NPD7128	Approved
0.6471	Remote Similarity	NPD6675	Approved
0.6471	Remote Similarity	NPD6402	Approved
0.6458	Remote Similarity	NPD7748	Approved
0.6437	Remote Similarity	NPD3671	Phase 1
0.6436	Remote Similarity	NPD5174	Approved
0.6436	Remote Similarity	NPD4754	Approved
0.6436	Remote Similarity	NPD5175	Approved
0.64	Remote Similarity	NPD4159	Approved
0.6383	Remote Similarity	NPD6051	Approved
0.6374	Remote Similarity	NPD4197	Approved
0.6346	Remote Similarity	NPD6899	Approved
0.6346	Remote Similarity	NPD6881	Approved
0.6346	Remote Similarity	NPD7320	Approved
0.6341	Remote Similarity	NPD6705	Phase 1
0.633	Remote Similarity	NPD7115	Discovery
0.6311	Remote Similarity	NPD4767	Approved
0.6311	Remote Similarity	NPD4768	Approved
0.631	Remote Similarity	NPD4758	Discontinued
0.6286	Remote Similarity	NPD6372	Approved
0.6286	Remote Similarity	NPD6373	Approved
0.6277	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6263	Remote Similarity	NPD6083	Phase 2
0.6263	Remote Similarity	NPD7902	Approved
0.6263	Remote Similarity	NPD6084	Phase 2
0.625	Remote Similarity	NPD5697	Approved
0.625	Remote Similarity	NPD5701	Approved
0.625	Remote Similarity	NPD3617	Approved
0.625	Remote Similarity	NPD7637	Suspended
0.6237	Remote Similarity	NPD6684	Approved
0.6237	Remote Similarity	NPD7521	Approved
0.6237	Remote Similarity	NPD4693	Phase 3
0.6237	Remote Similarity	NPD7334	Approved
0.6237	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6237	Remote Similarity	NPD7146	Approved
0.6237	Remote Similarity	NPD4688	Approved
0.6237	Remote Similarity	NPD6409	Approved
0.6237	Remote Similarity	NPD4138	Approved
0.6237	Remote Similarity	NPD4690	Approved
0.6237	Remote Similarity	NPD5205	Approved
0.6237	Remote Similarity	NPD4689	Approved
0.6237	Remote Similarity	NPD5330	Approved
0.6226	Remote Similarity	NPD7290	Approved
0.6226	Remote Similarity	NPD7102	Approved
0.6226	Remote Similarity	NPD6883	Approved
0.6224	Remote Similarity	NPD4629	Approved
0.6224	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6224	Remote Similarity	NPD5210	Approved
0.6203	Remote Similarity	NPD368	Approved
0.62	Remote Similarity	NPD4225	Approved
0.619	Remote Similarity	NPD4729	Approved
0.619	Remote Similarity	NPD6011	Approved
0.619	Remote Similarity	NPD5128	Approved
0.619	Remote Similarity	NPD5168	Approved
0.619	Remote Similarity	NPD4730	Approved
0.6168	Remote Similarity	NPD6650	Approved
0.6168	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6168	Remote Similarity	NPD6847	Approved
0.6168	Remote Similarity	NPD6617	Approved
0.6168	Remote Similarity	NPD6649	Approved
0.6168	Remote Similarity	NPD6869	Approved
0.6168	Remote Similarity	NPD8130	Phase 1
0.6146	Remote Similarity	NPD6701	Clinical (unspecified phase)
0.6146	Remote Similarity	NPD6700	Approved
0.6146	Remote Similarity	NPD7136	Phase 2
0.6132	Remote Similarity	NPD6012	Approved
0.6132	Remote Similarity	NPD6013	Approved
0.6132	Remote Similarity	NPD6014	Approved
0.6126	Remote Similarity	NPD7327	Approved
0.6126	Remote Similarity	NPD7328	Approved
0.6118	Remote Similarity	NPD6081	Approved
0.6111	Remote Similarity	NPD6882	Approved
0.6111	Remote Similarity	NPD8297	Approved
0.6105	Remote Similarity	NPD4723	Approved
0.6105	Remote Similarity	NPD6903	Approved
0.6105	Remote Similarity	NPD6672	Approved
0.6105	Remote Similarity	NPD5737	Approved
0.6105	Remote Similarity	NPD4722	Approved
0.6098	Remote Similarity	NPD4224	Phase 2
0.6082	Remote Similarity	NPD6702	Approved
0.6082	Remote Similarity	NPD6703	Approved
0.6075	Remote Similarity	NPD5169	Approved
0.6075	Remote Similarity	NPD5250	Approved
0.6075	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6075	Remote Similarity	NPD5251	Approved
0.6075	Remote Similarity	NPD4634	Approved
0.6075	Remote Similarity	NPD5248	Approved
0.6075	Remote Similarity	NPD5135	Approved
0.6075	Remote Similarity	NPD5247	Approved
0.6075	Remote Similarity	NPD5249	Phase 3

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