NPASS Compound

Structure

CID239584 OpenBabel06191716042D 42 49 0 0 1 0 0 0 0 0999 V2000 2.3821 -4.2830 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2450 -2.3222 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0805 -2.0918 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7880 -2.0448 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6463 -2.4497 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2094 -4.7248 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4894 -2.9069 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4142 -3.1197 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9449 -3.7781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3515 -0.4827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2481 -1.7830 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5215 -0.2145 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2481 -2.7830 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4199 -1.0695 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1804 -3.4075 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0116 -4.1757 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3821 -0.2830 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0605 -1.2482 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6501 -1.2830 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6483 -1.7407 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6601 -3.8891 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3821 -1.2830 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4988 -0.7640 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9772 -3.6780 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5161 -1.7830 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9860 -0.5088 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.5161 -2.7830 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0072 -3.5338 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6948 -4.2362 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5161 0.2170 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6501 -0.2830 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4087 -1.2074 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3936 -0.1194 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0341 -0.6723 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7067 0.0566 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8387 -0.2275 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.3821 -3.2830 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.2763 -2.5707 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0806 -2.0795 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3826 -4.0641 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9551 -0.6009 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 37 1 0 0 0 0 2 38 1 0 0 0 0 3 39 1 0 0 0 0 4 7 1 0 0 0 0 4 20 2 0 0 0 0 5 8 2 0 0 0 0 5 20 1 0 0 0 0 6 9 2 0 0 0 0 6 21 1 0 0 0 0 7 24 2 0 0 0 0 8 24 1 0 0 0 0 9 28 1 0 0 0 0 10 12 1 0 0 0 0 10 23 1 0 0 0 0 11 13 1 0 0 0 0 11 22 1 0 0 0 0 12 36 1 0 0 0 0 13 37 1 0 0 0 0 14 20 1 0 0 0 0 15 21 1 0 0 0 0 16 21 2 0 0 0 0 16 29 1 0 0 0 0 17 22 2 0 0 0 0 17 30 1 0 0 0 0 18 23 2 0 0 0 0 18 32 1 0 0 0 0 19 25 2 0 0 0 0 19 31 1 0 0 0 0 22 25 1 0 0 0 0 23 33 1 0 0 0 0 24 40 1 0 0 0 0 25 27 1 0 0 0 0 26 14 1 6 0 0 0 26 33 1 0 0 0 0 26 36 1 0 0 0 0 27 15 1 1 0 0 0 27 37 1 0 0 0 0 28 29 2 0 0 0 0 28 38 1 0 0 0 0 29 40 1 0 0 0 0 30 31 2 0 0 0 0 30 41 1 0 0 0 0 31 42 1 0 0 0 0 32 34 2 0 0 0 0 32 39 1 0 0 0 0 33 35 2 0 0 0 0 34 35 1 0 0 0 0 34 41 1 0 0 0 0 35 42 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	562.25
Volume:	579.771
LogP:	6.72
LogD:	3.71
LogS:	-7.902
# Rotatable Bonds:	2
TPSA:	61.42
# H-Bond Aceptor:	7
# H-Bond Donor:	1
# Rings:	9
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.251
Synthetic Accessibility Score:	5.892
Fsp3:	0.314
Lipinski Rule-of-5:	Rejected
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:	-5.726
MDCK Permeability:	2.1610096155200154e-05
Pgp-inhibitor:	0.999
Pgp-substrate:	0.987
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.752
30% Bioavailability (F30%):	0.955

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.058
Plasma Protein Binding (PPB):	61.5849609375%
Volume Distribution (VD):	0.765
Pgp-substrate:	16.420394897460938%

ADMET: Metabolism

CYP1A2-inhibitor:	0.097
CYP1A2-substrate:	0.95
CYP2C19-inhibitor:	0.207
CYP2C19-substrate:	0.952
CYP2C9-inhibitor:	0.052
CYP2C9-substrate:	0.67
CYP2D6-inhibitor:	0.016
CYP2D6-substrate:	0.955
CYP3A4-inhibitor:	0.12
CYP3A4-substrate:	0.949

ADMET: Excretion

Clearance (CL):	7.849
Half-life (T1/2):	0.109

ADMET: Toxicity

hERG Blockers:	0.967
Human Hepatotoxicity (H-HT):	0.023
Drug-inuced Liver Injury (DILI):	0.641
AMES Toxicity:	0.136
Rat Oral Acute Toxicity:	0.745
Maximum Recommended Daily Dose:	0.997
Skin Sensitization:	0.726
Carcinogencity:	0.049
Eye Corrosion:	0.003
Eye Irritation:	0.004
Respiratory Toxicity:	0.377

Download Data

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

Natural Product: NPC239584

Natural Product ID:	NPC239584
*Common Name:**	Trilobine
IUPAC Name:	n.a.
Synonyms:	(+)-N-Methyltelobine; Trilobine
Standard InCHIKey:	XZAXGQMTBGFTFE-SVBPBHIXSA-N
Standard InCHI:	InChI=1S/C35H34N2O5/c1-37-13-11-22-17-30-31-19-25(22)27(37)15-21-6-9-28(38-2)29(16-21)40-24-7-4-20(5-8-24)14-26-33-23(10-12-36-26)18-32(39-3)34(41-30)35(33)42-31/h4-9,16-19,26-27,36H,10-15H2,1-3H3/t26-,27-/m0/s1
SMILES:	COc1ccc2cc1Oc1ccc(cc1)C[C@@H]1NCCc3c1c1Oc4cc5[C@H](C2)N(C)CCc5cc4Oc1c(c3)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL500324
PubChem CID:	169007
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0001392] Lignans, neolignans and related compounds

*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
NPO27739	Erythrina mildbraedii	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/0031-9422(88)80746-5]
NPO27686	Aglaia odorata	Species	Meliaceae	Eukaryota	n.a.	leaf	n.a.	DOI[10.1016/S0031-9422(00)94986-0]
NPO25388	Siliquariaspongia japonica	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[10425118]
NPO12170	Solanum indicum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11575964]
NPO27931	Caulerpa taxifolia	Species	Caulerpaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16563751]
NPO27739	Erythrina mildbraedii	Species	Fabaceae	Eukaryota	root bark	Buea, Southwest Province, Cameroon	1997-JUL	PMID[17125223]
NPO27686	Aglaia odorata	Species	Meliaceae	Eukaryota	n.a.	flower	n.a.	PMID[17679444]
NPO27646	Cystoseira baccata	Species	Sargassaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18980381]
NPO13135	Campylotropis hirtella	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19481938]
NPO11351	Stephania japonica	Species	Menispermaceae	Eukaryota	Aerial parts	n.a.	n.a.	PMID[20426456]
NPO1698	Glycyrrhiza inflata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21123068]
NPO27617	Phoenix dactylifera	Species	Arecaceae	Eukaryota	n.a.	fruit	n.a.	PMID[23132311]
NPO12796	Periploca sepium	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28294615]
NPO1698	Glycyrrhiza inflata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28522265]
NPO1698	Glycyrrhiza inflata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[29641206]
NPO865	Dendrobium loddigesii	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31291099]
NPO26964	Stephania erecta	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8450319]
NPO26964	Stephania erecta	Species	Menispermaceae	Eukaryota	tubers	n.a.	n.a.	PMID[8450319]
NPO27686	Aglaia odorata	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8759160]
NPO11351	Stephania japonica	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9392886]
NPO27617	Phoenix dactylifera	Species	Arecaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO27617	Phoenix dactylifera	Species	Arecaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO27617	Phoenix dactylifera	Species	Arecaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO27617	Phoenix dactylifera	Species	Arecaceae	Eukaryota	Fruits	n.a.		Database[FooDB]
NPO1698	Glycyrrhiza inflata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO27666	Sophora tetraptera	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO865	Dendrobium loddigesii	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO96	Rhododendron capitatum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO27617	Phoenix dactylifera	Species	Arecaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7773	Crinum moorei	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO27803	Cercidiphyllum japonicum	Species	Cercidiphyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23450	Chionographis japonica	Species	Melanthiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO27686	Aglaia odorata	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26964	Stephania erecta	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13135	Campylotropis hirtella	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12796	Periploca sepium	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO6731	Ononis spinosa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11351	Stephania japonica	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26964	Stephania erecta	Species	Menispermaceae	Eukaryota	tubers	n.a.	n.a.	Database[PMID; Title]
NPO6731	Ononis spinosa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7389	Rhodiola atuntsuensis	Species	Crassulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13135	Campylotropis hirtella	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO96	Rhododendron capitatum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO865	Dendrobium loddigesii	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12796	Periploca sepium	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23450	Chionographis japonica	Species	Melanthiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11351	Stephania japonica	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7773	Crinum moorei	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1698	Glycyrrhiza inflata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12170	Solanum indicum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27686	Aglaia odorata	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27803	Cercidiphyllum japonicum	Species	Cercidiphyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26964	Stephania erecta	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27617	Phoenix dactylifera	Species	Arecaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27666	Sophora tetraptera	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5156	Hypoestes rosea	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO96	Rhododendron capitatum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO27617	Phoenix dactylifera	Species	Arecaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO27686	Aglaia odorata	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO6731	Ononis spinosa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO27666	Sophora tetraptera	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO1698	Glycyrrhiza inflata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO12796	Periploca sepium	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO865	Dendrobium loddigesii	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO27803	Cercidiphyllum japonicum	Species	Cercidiphyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO11351	Stephania japonica	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO12796	Periploca sepium	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO1698	Glycyrrhiza inflata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO865	Dendrobium loddigesii	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO11190	Veronica polita	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27216	Oreodaphne porosa	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO27869	Bombacopsis glabra	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO12796	Periploca sepium	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9319	Pterocaulon virgatum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10922	Pentaclethra macrophylla	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12170	Solanum indicum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25388	Siliquariaspongia japonica	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO27522	Gongronella urceolifera	Species	Cunninghamellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21720	Talaromyces variabilis	Species	Trichocomaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27726	Diplocarpon mali	Species	Dermateaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10605	Tristania conferta	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1698	Glycyrrhiza inflata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26964	Stephania erecta	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22691	Mentha cardiaca	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7822.1	Eucalyptus globulus subsp. bicostata	Subspecies	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5043	Eria japonica	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7389	Rhodiola atuntsuensis	Species	Crassulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24372	Artemisia palustris	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1815	Breonia chinensis	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1516	Passiflora suberosa	Species	Passifloraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18354	Meiothermus ruber	Species	Thermaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO9704	Sonneratia caseolaris	Species	Lythraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27686	Aglaia odorata	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12091	Martensia denticulata	Species	Delesseriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8934	Gypsophila perfoliata	Species	Caryophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27931	Caulerpa taxifolia	Species	Caulerpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27703	Eclipta erecta	Species	Cerambycidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26332	Ramalina tumidula	Species	Ramalinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO96	Rhododendron capitatum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5156	Hypoestes rosea	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23384	Rhodiola semenovii	Species	Crassulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27838	Rebutia marsoneri	Species	Cactaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9532	Vernonia cistifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO865	Dendrobium loddigesii	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23450	Chionographis japonica	Species	Melanthiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13135	Campylotropis hirtella	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6730	Crossopteryx febrifuga	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10638	Plectranthus myrianthus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO526	Salvia sessei	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27617	Phoenix dactylifera	Species	Arecaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6289	Ceropegia dichotoma	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3873	Crotalaria candicans	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27646	Cystoseira baccata	Species	Sargassaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6731	Ononis spinosa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5456	Juniperus drupacea	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12205	Eucalyptus apodophylla	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7773	Crinum moorei	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27976	Astragalus wootoni	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27803	Cercidiphyllum japonicum	Species	Cercidiphyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11843	Stephania zippeliana	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27739	Erythrina mildbraedii	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11576	Glycosmis macrophylla	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27666	Sophora tetraptera	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12565	Hypericum polyanthemum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27468	Rhizopogon roseolus	Species	Rhizopogonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19931	Pyrus x nivalis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1257	Distephanus angulifolius	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11351	Stephania japonica	Species	Menispermaceae	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
ED50	2
IC50	2
Others	10

Activity Type	# Activity
Cell Line	1
Organism	2
Others	11

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	ED50	=	8300.0	nM	PMID[491516]
NPT2	Others	Unspecified		Activity	=	2.0	n.a.	PMID[491515]
NPT2	Others	Unspecified		Activity	=	1.5	n.a.	PMID[491515]
NPT2	Others	Unspecified		Activity	=	1.0	n.a.	PMID[491515]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	169.0	nM	PMID[491516]
NPT2	Others	Unspecified		Selectivity Index	=	49.0	n.a.	PMID[491516]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	451.0	nM	PMID[491516]
NPT2	Others	Unspecified		Selectivity Index	=	19.0	n.a.	PMID[491516]
NPT2	Others	Unspecified		ED50	=	1	ug/ml	PMID[9392886]
NPT2	Others	Unspecified		Activity	=	0.17	n.a.	PMID[9392886]
NPT2	Others	Unspecified		Activity	=	0.13	n.a.	PMID[9392886]
NPT2	Others	Unspecified		Activity	=	0.1	n.a.	PMID[9392886]
NPT2	Others	Unspecified		Activity	=	0.05	n.a.	PMID[9392886]

☑ 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 NPC239584 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	435
0.1-0.2	2084
0.2-0.3	11106
0.3-0.4	7026
0.4-0.5	7252
0.5-0.6	10694
0.6-0.7	3342
0.7-0.8	527
0.8-0.85	113
0.85-0.9	45
0.9-0.95	47
0.95-1	26

Similarity Score	Similarity Level	Natural Product ID
0.9939	High Similarity	NPC475479
0.9939	High Similarity	NPC243454
0.9693	High Similarity	NPC129518
0.9693	High Similarity	NPC12424
0.9693	High Similarity	NPC41376
0.9693	High Similarity	NPC251580
0.9632	High Similarity	NPC76682
0.9632	High Similarity	NPC317439
0.9632	High Similarity	NPC227060
0.9632	High Similarity	NPC317145
0.9632	High Similarity	NPC198498
0.9632	High Similarity	NPC10908
0.9632	High Similarity	NPC276890
0.9632	High Similarity	NPC63646
0.9632	High Similarity	NPC115284
0.9588	High Similarity	NPC191132
0.9588	High Similarity	NPC60295
0.9529	High Similarity	NPC175890
0.9529	High Similarity	NPC274661
0.9529	High Similarity	NPC281581
0.9529	High Similarity	NPC11296
0.9529	High Similarity	NPC48490
0.9529	High Similarity	NPC82457
0.9477	High Similarity	NPC256124
0.9458	High Similarity	NPC293093
0.9294	High Similarity	NPC167116
0.9294	High Similarity	NPC274716
0.9294	High Similarity	NPC254441
0.9264	High Similarity	NPC475393
0.9235	High Similarity	NPC279228
0.9235	High Similarity	NPC258657
0.9235	High Similarity	NPC290582
0.9235	High Similarity	NPC15414
0.9235	High Similarity	NPC104196
0.9235	High Similarity	NPC182052
0.9235	High Similarity	NPC73492
0.9235	High Similarity	NPC271013
0.9235	High Similarity	NPC42663
0.9235	High Similarity	NPC223690
0.9235	High Similarity	NPC229373
0.9235	High Similarity	NPC185639
0.9235	High Similarity	NPC299990
0.9235	High Similarity	NPC328155
0.9235	High Similarity	NPC8836
0.9235	High Similarity	NPC222661
0.9235	High Similarity	NPC285931
0.9235	High Similarity	NPC311973
0.9235	High Similarity	NPC217748
0.9235	High Similarity	NPC290005
0.9235	High Similarity	NPC7715
0.9235	High Similarity	NPC54654
0.9235	High Similarity	NPC49075
0.9235	High Similarity	NPC239824
0.9235	High Similarity	NPC90998
0.9235	High Similarity	NPC181796
0.9235	High Similarity	NPC251735
0.9186	High Similarity	NPC65312
0.9186	High Similarity	NPC139783
0.9176	High Similarity	NPC286119
0.9128	High Similarity	NPC16357
0.9128	High Similarity	NPC302245
0.9128	High Similarity	NPC95426
0.9123	High Similarity	NPC30779
0.9075	High Similarity	NPC116465
0.9075	High Similarity	NPC212237
0.907	High Similarity	NPC302275
0.9023	High Similarity	NPC22115
0.9023	High Similarity	NPC275680
0.9017	High Similarity	NPC249996
0.8971	High Similarity	NPC206900
0.8957	High Similarity	NPC25084
0.8957	High Similarity	NPC247639
0.8953	High Similarity	NPC195538
0.892	High Similarity	NPC475597
0.892	High Similarity	NPC473716
0.8902	High Similarity	NPC476202
0.887	High Similarity	NPC24260
0.8857	High Similarity	NPC14507
0.8857	High Similarity	NPC47077
0.8824	High Similarity	NPC475215
0.8824	High Similarity	NPC108434
0.8764	High Similarity	NPC478093
0.8715	High Similarity	NPC478092
0.8715	High Similarity	NPC478091
0.8715	High Similarity	NPC30182
0.8715	High Similarity	NPC473589
0.8713	High Similarity	NPC10871
0.8667	High Similarity	NPC187022
0.8667	High Similarity	NPC80129
0.8647	High Similarity	NPC204947
0.8611	High Similarity	NPC85381
0.8603	High Similarity	NPC318805
0.8603	High Similarity	NPC41122
0.8588	High Similarity	NPC317272
0.8588	High Similarity	NPC42549
0.8588	High Similarity	NPC240841
0.8588	High Similarity	NPC268503
0.8588	High Similarity	NPC13916
0.8588	High Similarity	NPC250846
0.8588	High Similarity	NPC256012
0.8588	High Similarity	NPC264850
0.8579	High Similarity	NPC475654
0.8541	High Similarity	NPC254581
0.8529	High Similarity	NPC24465
0.8523	High Similarity	NPC257269
0.8523	High Similarity	NPC230276
0.8516	High Similarity	NPC234318
0.8512	High Similarity	NPC7393
0.8488	Intermediate Similarity	NPC204908
0.8488	Intermediate Similarity	NPC83198
0.8466	Intermediate Similarity	NPC106295
0.8466	Intermediate Similarity	NPC476144
0.8466	Intermediate Similarity	NPC40496
0.8466	Intermediate Similarity	NPC210437
0.8466	Intermediate Similarity	NPC51957
0.8466	Intermediate Similarity	NPC119068
0.8466	Intermediate Similarity	NPC16107
0.8415	Intermediate Similarity	NPC7467
0.8362	Intermediate Similarity	NPC474507
0.8343	Intermediate Similarity	NPC152680
0.8343	Intermediate Similarity	NPC232386
0.8343	Intermediate Similarity	NPC190783
0.8333	Intermediate Similarity	NPC123323
0.8333	Intermediate Similarity	NPC109925
0.8315	Intermediate Similarity	NPC474506
0.8315	Intermediate Similarity	NPC32413
0.8314	Intermediate Similarity	NPC4138
0.8314	Intermediate Similarity	NPC284183
0.8314	Intermediate Similarity	NPC121275
0.8305	Intermediate Similarity	NPC23219
0.8266	Intermediate Similarity	NPC223077
0.8266	Intermediate Similarity	NPC193853
0.8266	Intermediate Similarity	NPC56887
0.8258	Intermediate Similarity	NPC470879
0.8258	Intermediate Similarity	NPC258695
0.8249	Intermediate Similarity	NPC148709
0.8249	Intermediate Similarity	NPC173416
0.8249	Intermediate Similarity	NPC476577
0.8249	Intermediate Similarity	NPC112575
0.8221	Intermediate Similarity	NPC476567
0.8221	Intermediate Similarity	NPC128019
0.8221	Intermediate Similarity	NPC136860
0.8214	Intermediate Similarity	NPC114124
0.8208	Intermediate Similarity	NPC209377
0.8176	Intermediate Similarity	NPC203784
0.8176	Intermediate Similarity	NPC170503
0.8176	Intermediate Similarity	NPC126519
0.8129	Intermediate Similarity	NPC476572
0.8118	Intermediate Similarity	NPC193949
0.8118	Intermediate Similarity	NPC54379
0.8118	Intermediate Similarity	NPC207757
0.8118	Intermediate Similarity	NPC278799
0.8118	Intermediate Similarity	NPC127674
0.8118	Intermediate Similarity	NPC39701
0.8118	Intermediate Similarity	NPC172765
0.8118	Intermediate Similarity	NPC189266
0.8118	Intermediate Similarity	NPC276588
0.8118	Intermediate Similarity	NPC2413
0.8118	Intermediate Similarity	NPC295691
0.8118	Intermediate Similarity	NPC138487
0.8118	Intermediate Similarity	NPC325871
0.8118	Intermediate Similarity	NPC204828
0.8118	Intermediate Similarity	NPC99659
0.8118	Intermediate Similarity	NPC249797
0.8118	Intermediate Similarity	NPC216459
0.8118	Intermediate Similarity	NPC184026
0.8118	Intermediate Similarity	NPC5238
0.8118	Intermediate Similarity	NPC41178
0.8118	Intermediate Similarity	NPC110416
0.8118	Intermediate Similarity	NPC469817
0.8098	Intermediate Similarity	NPC328750
0.8098	Intermediate Similarity	NPC188163
0.8098	Intermediate Similarity	NPC475754
0.8098	Intermediate Similarity	NPC213206
0.8098	Intermediate Similarity	NPC474915
0.8079	Intermediate Similarity	NPC149090
0.8079	Intermediate Similarity	NPC239775
0.8079	Intermediate Similarity	NPC19520
0.807	Intermediate Similarity	NPC146288
0.8061	Intermediate Similarity	NPC38964
0.8059	Intermediate Similarity	NPC2295
0.8059	Intermediate Similarity	NPC477564
0.8054	Intermediate Similarity	NPC476565
0.8037	Intermediate Similarity	NPC314682
0.8036	Intermediate Similarity	NPC92541
0.8036	Intermediate Similarity	NPC207824
0.8036	Intermediate Similarity	NPC60538
0.8035	Intermediate Similarity	NPC205255
0.8035	Intermediate Similarity	NPC235143
0.8035	Intermediate Similarity	NPC271388
0.8035	Intermediate Similarity	NPC119649
0.8035	Intermediate Similarity	NPC230956
0.8034	Intermediate Similarity	NPC66341
0.8034	Intermediate Similarity	NPC477020
0.8034	Intermediate Similarity	NPC192135
0.8033	Intermediate Similarity	NPC57036
0.8023	Intermediate Similarity	NPC118274
0.8023	Intermediate Similarity	NPC69712
0.8023	Intermediate Similarity	NPC477562
0.8023	Intermediate Similarity	NPC168753

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 NPC239584 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	219
0.1-0.2	793
0.2-0.3	1127
0.3-0.4	2159
0.4-0.5	2550
0.5-0.6	1577
0.6-0.7	603
0.7-0.8	107
0.8-0.85	8
0.85-0.9	1
0.9-0.95	3
0.95-1	3

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9632	High Similarity	NPD8252	Approved
0.9632	High Similarity	NPD8099	Discontinued
0.9632	High Similarity	NPD8251	Approved
0.9573	High Similarity	NPD8156	Discontinued
0.9235	High Similarity	NPD8053	Approved
0.9235	High Similarity	NPD8054	Approved
0.8667	High Similarity	NPD7298	Approved
0.8626	High Similarity	NPD8095	Phase 1
0.8466	Intermediate Similarity	NPD8453	Clinical (unspecified phase)
0.8466	Intermediate Similarity	NPD4584	Approved
0.8402	Intermediate Similarity	NPD6788	Approved
0.8242	Intermediate Similarity	NPD1424	Approved
0.8144	Intermediate Similarity	NPD6030	Approved
0.8144	Intermediate Similarity	NPD6031	Approved
0.8098	Intermediate Similarity	NPD4664	Clinical (unspecified phase)
0.7941	Intermediate Similarity	NPD7261	Clinical (unspecified phase)
0.7898	Intermediate Similarity	NPD6107	Approved
0.7857	Intermediate Similarity	NPD7598	Phase 2
0.7849	Intermediate Similarity	NPD4773	Phase 2
0.7849	Intermediate Similarity	NPD4772	Phase 2
0.7778	Intermediate Similarity	NPD7667	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD7045	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7657	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.7654	Intermediate Similarity	NPD6071	Discontinued
0.7633	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7588	Intermediate Similarity	NPD7124	Phase 2
0.7571	Intermediate Similarity	NPD4581	Clinical (unspecified phase)
0.7557	Intermediate Similarity	NPD4585	Approved
0.7556	Intermediate Similarity	NPD3051	Approved
0.7553	Intermediate Similarity	NPD7906	Approved
0.7542	Intermediate Similarity	NPD5677	Discontinued
0.7542	Intermediate Similarity	NPD7201	Clinical (unspecified phase)
0.7529	Intermediate Similarity	NPD4017	Approved
0.7528	Intermediate Similarity	NPD7832	Clinical (unspecified phase)
0.7528	Intermediate Similarity	NPD7833	Phase 2
0.7528	Intermediate Similarity	NPD7831	Phase 2
0.7514	Intermediate Similarity	NPD3641	Approved
0.7514	Intermediate Similarity	NPD3639	Approved
0.7514	Intermediate Similarity	NPD3640	Phase 3
0.75	Intermediate Similarity	NPD7802	Discontinued
0.7473	Intermediate Similarity	NPD4481	Phase 3
0.7459	Intermediate Similarity	NPD4166	Phase 2
0.7457	Intermediate Similarity	NPD3647	Clinical (unspecified phase)
0.743	Intermediate Similarity	NPD4055	Discovery
0.7418	Intermediate Similarity	NPD2970	Approved
0.7418	Intermediate Similarity	NPD2969	Approved
0.7416	Intermediate Similarity	NPD2560	Approved
0.7416	Intermediate Similarity	NPD2563	Approved
0.7414	Intermediate Similarity	NPD5976	Discontinued
0.7399	Intermediate Similarity	NPD7447	Phase 1
0.7394	Intermediate Similarity	NPD4474	Approved
0.7394	Intermediate Similarity	NPD6851	Approved
0.7394	Intermediate Similarity	NPD4475	Approved
0.7394	Intermediate Similarity	NPD6853	Approved
0.738	Intermediate Similarity	NPD7549	Discontinued
0.7368	Intermediate Similarity	NPD6748	Discontinued
0.7366	Intermediate Similarity	NPD6297	Approved
0.7341	Intermediate Similarity	NPD3124	Discontinued
0.734	Intermediate Similarity	NPD7310	Approved
0.734	Intermediate Similarity	NPD7312	Approved
0.734	Intermediate Similarity	NPD7311	Approved
0.734	Intermediate Similarity	NPD7313	Approved
0.7333	Intermediate Similarity	NPD5718	Phase 2
0.7321	Intermediate Similarity	NPD2200	Suspended
0.7317	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD4162	Approved
0.7303	Intermediate Similarity	NPD3383	Approved
0.7303	Intermediate Similarity	NPD3384	Approved
0.7303	Intermediate Similarity	NPD3382	Approved
0.7302	Intermediate Similarity	NPD6618	Phase 2
0.7302	Intermediate Similarity	NPD7309	Approved
0.7283	Intermediate Similarity	NPD2489	Approved
0.7283	Intermediate Similarity	NPD3845	Phase 1
0.7283	Intermediate Similarity	NPD27	Approved
0.7273	Intermediate Similarity	NPD5006	Approved
0.7273	Intermediate Similarity	NPD6996	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD5005	Approved
0.7267	Intermediate Similarity	NPD7466	Approved
0.7267	Intermediate Similarity	NPD3977	Clinical (unspecified phase)
0.7258	Intermediate Similarity	NPD5312	Approved
0.7258	Intermediate Similarity	NPD5313	Approved
0.7249	Intermediate Similarity	NPD4578	Approved
0.7249	Intermediate Similarity	NPD4577	Approved
0.7241	Intermediate Similarity	NPD7213	Phase 3
0.7241	Intermediate Similarity	NPD7212	Phase 2
0.7232	Intermediate Similarity	NPD8158	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD5160	Discontinued
0.7225	Intermediate Similarity	NPD4663	Approved
0.7207	Intermediate Similarity	NPD8153	Approved
0.7207	Intermediate Similarity	NPD5720	Discontinued
0.7207	Intermediate Similarity	NPD8152	Approved
0.72	Intermediate Similarity	NPD1754	Clinical (unspecified phase)
0.7191	Intermediate Similarity	NPD4675	Approved
0.7191	Intermediate Similarity	NPD4678	Approved
0.7166	Intermediate Similarity	NPD42	Phase 2
0.7166	Intermediate Similarity	NPD6042	Phase 2
0.7158	Intermediate Similarity	NPD2971	Approved
0.7158	Intermediate Similarity	NPD2968	Approved
0.7135	Intermediate Similarity	NPD4005	Discontinued
0.7135	Intermediate Similarity	NPD1632	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD5241	Discontinued
0.7126	Intermediate Similarity	NPD2677	Approved
0.7118	Intermediate Similarity	NPD6896	Approved
0.7118	Intermediate Similarity	NPD6111	Discontinued
0.7118	Intermediate Similarity	NPD6895	Approved
0.711	Intermediate Similarity	NPD3060	Approved
0.7107	Intermediate Similarity	NPD6621	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD2422	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD3532	Approved
0.7083	Intermediate Similarity	NPD5087	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD3531	Approved
0.7083	Intermediate Similarity	NPD3530	Approved
0.7081	Intermediate Similarity	NPD4010	Discontinued
0.7071	Intermediate Similarity	NPD4420	Approved
0.7066	Intermediate Similarity	NPD2669	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD3489	Phase 3
0.7056	Intermediate Similarity	NPD6072	Discontinued
0.7049	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD1774	Approved
0.7039	Intermediate Similarity	NPD7827	Phase 1
0.7037	Intermediate Similarity	NPD7479	Phase 2
0.7029	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7022	Intermediate Similarity	NPD2122	Discontinued
0.702	Intermediate Similarity	NPD2973	Approved
0.702	Intermediate Similarity	NPD2975	Approved
0.702	Intermediate Similarity	NPD2974	Approved
0.7017	Intermediate Similarity	NPD5722	Discontinued
0.701	Intermediate Similarity	NPD7291	Discontinued
0.7005	Intermediate Similarity	NPD2898	Approved
0.6978	Remote Similarity	NPD5773	Approved
0.6978	Remote Similarity	NPD5772	Approved
0.6978	Remote Similarity	NPD7046	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD2156	Approved
0.6977	Remote Similarity	NPD2155	Approved
0.6977	Remote Similarity	NPD2154	Approved
0.6971	Remote Similarity	NPD6658	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD5602	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD5261	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD7527	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD52	Approved
0.6966	Remote Similarity	NPD7526	Approved
0.6959	Remote Similarity	NPD2653	Approved
0.6954	Remote Similarity	NPD7153	Discontinued
0.6954	Remote Similarity	NPD1372	Clinical (unspecified phase)
0.695	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6949	Remote Similarity	NPD2420	Approved
0.6949	Remote Similarity	NPD2421	Approved
0.6944	Remote Similarity	NPD6523	Clinical (unspecified phase)
0.6935	Remote Similarity	NPD7034	Discontinued
0.6931	Remote Similarity	NPD5940	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD7132	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD6812	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD7945	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD5709	Phase 3
0.6915	Remote Similarity	NPD4580	Approved
0.6914	Remote Similarity	NPD5177	Phase 3
0.691	Remote Similarity	NPD4123	Phase 3
0.6905	Remote Similarity	NPD3537	Clinical (unspecified phase)
0.6888	Remote Similarity	NPD2845	Phase 2
0.6888	Remote Similarity	NPD2843	Phase 2
0.6885	Remote Similarity	NPD2978	Approved
0.6885	Remote Similarity	NPD2977	Approved
0.6882	Remote Similarity	NPD4666	Phase 3
0.6882	Remote Similarity	NPD554	Clinical (unspecified phase)
0.6881	Remote Similarity	NPD3452	Approved
0.6881	Remote Similarity	NPD3450	Approved
0.6881	Remote Similarity	NPD2493	Approved
0.6881	Remote Similarity	NPD2494	Approved
0.6868	Remote Similarity	NPD7110	Phase 1
0.6868	Remote Similarity	NPD7109	Clinical (unspecified phase)
0.6868	Remote Similarity	NPD5090	Approved
0.6868	Remote Similarity	NPD5089	Approved
0.6867	Remote Similarity	NPD7258	Clinical (unspecified phase)
0.6862	Remote Similarity	NPD5242	Approved
0.6854	Remote Similarity	NPD6087	Phase 1
0.6853	Remote Similarity	NPD2488	Approved
0.6853	Remote Similarity	NPD2490	Approved
0.6853	Remote Similarity	NPD5525	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD3109	Approved
0.6842	Remote Similarity	NPD5708	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD3110	Approved
0.684	Remote Similarity	NPD8318	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD3156	Discontinued
0.6833	Remote Similarity	NPD4727	Phase 1
0.6832	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD5457	Discontinued
0.6831	Remote Similarity	NPD1769	Discontinued
0.6824	Remote Similarity	NPD1336	Approved
0.6822	Remote Similarity	NPD6997	Phase 2
0.6818	Remote Similarity	NPD5061	Approved
0.6818	Remote Similarity	NPD2460	Phase 3
0.6818	Remote Similarity	NPD2458	Approved
0.6818	Remote Similarity	NPD4237	Approved
0.6818	Remote Similarity	NPD5062	Approved
0.6818	Remote Similarity	NPD4236	Phase 3
0.6818	Remote Similarity	NPD2459	Approved
0.6816	Remote Similarity	NPD4160	Clinical (unspecified phase)

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