NPASS Compound

Structure

CID24821 OpenBabel06191715352D 26 28 0 0 0 0 0 0 0 0999 V2000 5.1962 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 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 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 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 -4.3301 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 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 10 1 0 0 0 0 2 10 1 0 0 0 0 3 8 1 0 0 0 0 3 10 2 0 0 0 0 4 6 1 0 0 0 0 4 11 2 0 0 0 0 5 7 2 0 0 0 0 5 11 1 0 0 0 0 6 12 2 0 0 0 0 7 12 1 0 0 0 0 8 13 1 0 0 0 0 9 14 2 0 0 0 0 9 15 1 0 0 0 0 11 20 1 0 0 0 0 12 21 1 0 0 0 0 13 14 1 0 0 0 0 13 17 2 0 0 0 0 14 22 1 0 0 0 0 15 16 2 0 0 0 0 15 26 1 0 0 0 0 16 17 1 0 0 0 0 16 18 1 0 0 0 0 17 23 1 0 0 0 0 18 19 1 0 0 0 0 18 24 2 0 0 0 0 19 20 2 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:	354.11
Volume:	357.82
LogP:	4.58
LogD:	2.322
LogS:	-3.27
# Rotatable Bonds:	3
TPSA:	111.13
# H-Bond Aceptor:	6
# H-Bond Donor:	4
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.533
Synthetic Accessibility Score:	2.742
Fsp3:	0.15
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.942
MDCK Permeability:	1.2414883713063318e-05
Pgp-inhibitor:	0.043
Pgp-substrate:	0.065
Human Intestinal Absorption (HIA):	0.012
20% Bioavailability (F20%):	0.763
30% Bioavailability (F30%):	0.982

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.006
Plasma Protein Binding (PPB):	97.27860260009766%
Volume Distribution (VD):	0.545
Pgp-substrate:	4.416414737701416%

ADMET: Metabolism

CYP1A2-inhibitor:	0.898
CYP1A2-substrate:	0.141
CYP2C19-inhibitor:	0.73
CYP2C19-substrate:	0.051
CYP2C9-inhibitor:	0.791
CYP2C9-substrate:	0.78
CYP2D6-inhibitor:	0.758
CYP2D6-substrate:	0.211
CYP3A4-inhibitor:	0.26
CYP3A4-substrate:	0.07

ADMET: Excretion

Clearance (CL):	6.356
Half-life (T1/2):	0.821

ADMET: Toxicity

hERG Blockers:	0.011
Human Hepatotoxicity (H-HT):	0.394
Drug-inuced Liver Injury (DILI):	0.976
AMES Toxicity:	0.607
Rat Oral Acute Toxicity:	0.233
Maximum Recommended Daily Dose:	0.04
Skin Sensitization:	0.87
Carcinogencity:	0.098
Eye Corrosion:	0.003
Eye Irritation:	0.886
Respiratory Toxicity:	0.08

Download Data

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

Natural Product: NPC24821

Natural Product ID:	NPC24821
*Common Name:**	Licoflavonol
IUPAC Name:	3,5,7-trihydroxy-2-(4-hydroxyphenyl)-6-(3-methylbut-2-enyl)chromen-4-one
Synonyms:	Licoflavonol
Standard InCHIKey:	TVMHBSODLWMMMV-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C20H18O6/c1-10(2)3-8-13-14(22)9-15-16(17(13)23)18(24)19(25)20(26-15)11-4-6-12(21)7-5-11/h3-7,9,21-23,25H,8H2,1-2H3
SMILES:	CC(=CCc1c(cc2c(c1O)c(=O)c(c(c1ccc(cc1)O)o2)O)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL600185
PubChem CID:	5481964
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001615] Flavones [CHEMONTID:0003503] 6-prenylated flavones

*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
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10654410]
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	n.a.	root	n.a.	PMID[10843587]
NPO20142	Embelia schimperi	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11054840]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[12713396]
NPO18668	Asimina parviflora	Species	Annonaceae	Eukaryota	twigs	n.a.	n.a.	PMID[1453182]
NPO19667	Hypericum styphelioides	Species	Hypericaceae	Eukaryota	leaves	n.a.	n.a.	PMID[15165152]
NPO19667	Hypericum styphelioides	Species	Hypericaceae	Eukaryota	n.a.	leaf	n.a.	PMID[15165152]
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	Roots	n.a.	n.a.	PMID[15568770]
NPO18286	Lycogala epidendrum	Species	Enteridiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[15911254]
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	n.a.	root	n.a.	PMID[16392664]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	root	n.a.	PMID[16441081]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16675659]
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	roots	Hualien Hsien, Taiwan	2003-JUL	PMID[16933887]
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	n.a.	root	n.a.	PMID[16933887]
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	n.a.	root	n.a.	PMID[17951038]
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18175961]
NPO20879	Clerodendrum bungei	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18348535]
NPO18176	Ephedra sinica	Species	Ephedraceae	Eukaryota	n.a.	root	n.a.	PMID[18975262]
NPO3152	Morella rubra	Species	Myricaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19407970]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	roots	n.a.	n.a.	PMID[20022509]
NPO1698	Glycyrrhiza inflata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21123068]
NPO3152	Morella rubra	Species	Myricaceae	Eukaryota	n.a.	bark	n.a.	PMID[21553897]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21866899]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	root	n.a.	PMID[22074222]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22074222]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23325115]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	Roots	n.a.	n.a.	PMID[23541646]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	root	n.a.	PMID[23867078]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	rhizome	n.a.	PMID[23867078]
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24295087]
NPO18176	Ephedra sinica	Species	Ephedraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24333010]
NPO20598	Lythrum salicaria	Species	Lythraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24459770]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24479468]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	roots	n.a.	n.a.	PMID[24957203]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25445757]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25744461]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26841168]
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27575476]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28140583]
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]
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	Roots	n.a.	n.a.	PMID[30298740]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32196343]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7381508]
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	Roots	n.a.	n.a.	PMID[9868163]
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	n.a.	root	n.a.	Database[Article]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18286	Lycogala epidendrum	Species	Enteridiidae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18176	Ephedra sinica	Species	Ephedraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1698	Glycyrrhiza inflata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21375	Euphorbia nematocypha	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17334	Onopordum acanthium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12056	Chondrodendron tomentosum	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21170	Embelia parviflora	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO20598	Lythrum salicaria	Species	Lythraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO16193	Glycyrrhiza sp.	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18668	Asimina parviflora	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12056	Chondrodendron tomentosum	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3152	Morella rubra	Species	Myricaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18286	Lycogala epidendrum	Species	Enteridiidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20142	Embelia schimperi	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17334	Onopordum acanthium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20680	Erythrina melanacantha	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18176	Ephedra sinica	Species	Ephedraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20879	Clerodendrum bungei	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21170	Embelia parviflora	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20598	Lythrum salicaria	Species	Lythraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21375	Euphorbia nematocypha	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1698	Glycyrrhiza inflata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20489	Epilobium hirsutum	Species	Onagraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18176	Ephedra sinica	Species	Ephedraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO21375	Euphorbia nematocypha	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO20598	Lythrum salicaria	Species	Lythraceae	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]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO17334	Onopordum acanthium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO20680	Erythrina melanacantha	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO21170	Embelia parviflora	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO18286	Lycogala epidendrum	Species	Enteridiidae	Eukaryota	n.a.	n.a.	n.a.	Database[Title]
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO18176	Ephedra sinica	Species	Ephedraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO1698	Glycyrrhiza inflata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO21631	Faramea salicifolia	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19912	Vellozia nanuzae	Species	Velloziaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21108	Eria anomala	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22937	Vernonia fagifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17334	Onopordum acanthium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7786	Lentinus tigrinus	Species	Lentinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20598	Lythrum salicaria	Species	Lythraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19511	Dolabella californica	Species	Aplysiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21170	Embelia parviflora	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16141	Piper regnellii	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5903	Conus mus	Species	Conidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11523	Erysimum leptophyllum	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17560	Pancratium sickenbergeri	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3152	Morella rubra	Species	Myricaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28072	Theonella conica	Species	Theonellidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20084	Atraphaxis spinosa	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16569	Gymnocalycium schickendantzii	Species	Cactaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19810	Myxococcus stipitatus	Species	Myxococcaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO18176	Ephedra sinica	Species	Ephedraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20879	Clerodendrum bungei	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20142	Embelia schimperi	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20489	Epilobium hirsutum	Species	Onagraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20421	Aplophyllum alberti-regelii	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO17849	Centaurea maculosa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21375	Euphorbia nematocypha	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13449	Syzygium polycephaloides	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20680	Erythrina melanacantha	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20843	Monsonia senegalensis	Species	Geraniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12056	Chondrodendron tomentosum	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14241	Planchonia grandis	Species	Asterolecaniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4051	Tricholoma columbetta	Species	Tricholomataceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19036	Esenbeckia leiocarpa	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17258	Rhinella marina	Species	Bufonidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1698	Glycyrrhiza inflata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18866	Pteridium esculentum	Species	Dennstaedtiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21038	Lemaireocereus longispinus	Species	Cactaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12313	Haplophyllum obtusifolium	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28202	Helichrysum tenuifolium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18668	Asimina parviflora	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21562	Diospyros assimilis	Species	Ebenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19667	Hypericum styphelioides	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20624	Simarouba glauca	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27367	Latrunculia magnifica	Species	Latrunculiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18286	Lycogala epidendrum	Species	Enteridiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18473	Plathymenia reticulata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21243	Siphonaria capensis	Species	Siphonariidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9968	Shigella dysenteriae	Species	Enterobacteriaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO18143	Dendronephthya griffini	Species	Nephtheidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19995	Baccharis neglecta	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10026	Mitracarpus scaber	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22961	Cordia leucocephala	Species	Cordiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21495	Abelia chinensis	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

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

NP Quantity Composition/Concentration

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

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

Biological Activity

Activity Type	# Activity
EC50	3
IC50	1
Ki	1
MIC	2
Others	8

Activity Type	# Activity
Cell Line	1
Individual Protein	2
NON-MOLECULAR	5
Others	7

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT178	Individual Protein	Protein-tyrosine phosphatase 1B	Homo sapiens	Inhibition	=	51.0	%	PMID[523460]
NPT178	Individual Protein	Protein-tyrosine phosphatase 1B	Homo sapiens	Inhibition	>	60.0	%	PMID[523461]
NPT65	Cell Line	HepG2	Homo sapiens	Activity	=	80.0	%	PMID[523461]
NPT2	Others	Unspecified		IC50	=	20600.0	nM	PMID[523458]
NPT2	Others	Unspecified		Ki	=	33000.0	nM	PMID[523458]
NPT27	Others	Unspecified		CC50	=	85300.0	nM	PMID[523459]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	EC50	=	15500.0	nM	PMID[523459]
NPT2	Others	Unspecified		Ratio CC50/EC50	=	5.5	n.a.	PMID[523459]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	EC50	=	36800.0	nM	PMID[523459]
NPT2	Others	Unspecified		Ratio CC50/EC50	=	2.3	n.a.	PMID[523459]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	EC50	=	25900.0	nM	PMID[523459]
NPT2	Others	Unspecified		Ratio CC50/EC50	=	3.3	n.a.	PMID[523459]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	MIC	=	17200.0	nM	PMID[523459]
NPT2	Others	Unspecified		Inhibition	>	40.0	%	PMID[523461]

☑ 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 NPC24821 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	430
0.1-0.2	1889
0.2-0.3	4734
0.3-0.4	11167
0.4-0.5	6512
0.5-0.6	3948
0.6-0.7	5329
0.7-0.8	4278
0.8-0.85	2146
0.85-0.9	1647
0.9-0.95	543
0.95-1	74

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC293053
1.0	High Similarity	NPC9117
1.0	High Similarity	NPC190637
1.0	High Similarity	NPC212932
0.9928	High Similarity	NPC216538
0.9928	High Similarity	NPC326500
0.9928	High Similarity	NPC273538
0.9927	High Similarity	NPC200694
0.9927	High Similarity	NPC473042
0.9856	High Similarity	NPC306488
0.9856	High Similarity	NPC124729
0.9856	High Similarity	NPC178343
0.9856	High Similarity	NPC5820
0.9786	High Similarity	NPC14001
0.9786	High Similarity	NPC166757
0.9716	High Similarity	NPC296869
0.9716	High Similarity	NPC244407
0.9714	High Similarity	NPC220418
0.9712	High Similarity	NPC158874
0.9708	High Similarity	NPC96565
0.9708	High Similarity	NPC301217
0.9708	High Similarity	NPC216978
0.9708	High Similarity	NPC303633
0.9708	High Similarity	NPC55018
0.9708	High Similarity	NPC220062
0.9648	High Similarity	NPC269420
0.9648	High Similarity	NPC470461
0.9638	High Similarity	NPC270883
0.9638	High Similarity	NPC241100
0.9638	High Similarity	NPC172986
0.9638	High Similarity	NPC261227
0.9638	High Similarity	NPC159275
0.9635	High Similarity	NPC201395
0.958	High Similarity	NPC61258
0.9577	High Similarity	NPC470460
0.9574	High Similarity	NPC470458
0.9571	High Similarity	NPC219915
0.9571	High Similarity	NPC11700
0.9568	High Similarity	NPC118840
0.9568	High Similarity	NPC110969
0.9568	High Similarity	NPC64908
0.9568	High Similarity	NPC282300
0.9568	High Similarity	NPC147688
0.9568	High Similarity	NPC262094
0.9568	High Similarity	NPC90582
0.9568	High Similarity	NPC205006
0.9568	High Similarity	NPC156590
0.9565	High Similarity	NPC241838
0.9565	High Similarity	NPC143799
0.9565	High Similarity	NPC18260
0.9565	High Similarity	NPC78913
0.9565	High Similarity	NPC217186
0.9565	High Similarity	NPC53181
0.9565	High Similarity	NPC152042
0.9504	High Similarity	NPC234629
0.9504	High Similarity	NPC224714
0.9504	High Similarity	NPC311741
0.95	High Similarity	NPC11561
0.95	High Similarity	NPC226636
0.95	High Similarity	NPC214236
0.95	High Similarity	NPC299080
0.95	High Similarity	NPC62840
0.95	High Similarity	NPC78803
0.95	High Similarity	NPC217083
0.95	High Similarity	NPC293852
0.95	High Similarity	NPC59739
0.95	High Similarity	NPC144499
0.9496	High Similarity	NPC475680
0.9496	High Similarity	NPC184536
0.9496	High Similarity	NPC146679
0.9496	High Similarity	NPC305355
0.9496	High Similarity	NPC281207
0.9496	High Similarity	NPC235239
0.9496	High Similarity	NPC230285
0.9496	High Similarity	NPC269652
0.9496	High Similarity	NPC150522
0.9496	High Similarity	NPC59951
0.9496	High Similarity	NPC103342
0.9496	High Similarity	NPC69769
0.9496	High Similarity	NPC103904
0.9493	High Similarity	NPC276905
0.9489	High Similarity	NPC187432
0.9489	High Similarity	NPC13408
0.9489	High Similarity	NPC281917
0.9489	High Similarity	NPC256042
0.9489	High Similarity	NPC116775
0.9489	High Similarity	NPC216361
0.9448	High Similarity	NPC157784
0.9448	High Similarity	NPC37684
0.9448	High Similarity	NPC45934
0.9448	High Similarity	NPC63187
0.9448	High Similarity	NPC142527
0.9441	High Similarity	NPC168085
0.9437	High Similarity	NPC472629
0.9437	High Similarity	NPC154217
0.9433	High Similarity	NPC166138
0.9433	High Similarity	NPC38219
0.9433	High Similarity	NPC106985
0.9433	High Similarity	NPC18585
0.9429	High Similarity	NPC469404
0.9429	High Similarity	NPC136840
0.9429	High Similarity	NPC103362
0.9429	High Similarity	NPC14871
0.942	High Similarity	NPC299379
0.942	High Similarity	NPC228661
0.9384	High Similarity	NPC193200
0.9384	High Similarity	NPC236756
0.9384	High Similarity	NPC311579
0.9379	High Similarity	NPC278476
0.9379	High Similarity	NPC304295
0.9379	High Similarity	NPC262038
0.9379	High Similarity	NPC59162
0.9379	High Similarity	NPC205046
0.9379	High Similarity	NPC262039
0.9379	High Similarity	NPC319910
0.9379	High Similarity	NPC254412
0.9375	High Similarity	NPC317492
0.9375	High Similarity	NPC5173
0.9371	High Similarity	NPC237635
0.9371	High Similarity	NPC79469
0.9371	High Similarity	NPC473077
0.9371	High Similarity	NPC104406
0.9371	High Similarity	NPC24673
0.9371	High Similarity	NPC296998
0.9371	High Similarity	NPC201731
0.9371	High Similarity	NPC97716
0.9371	High Similarity	NPC308200
0.9366	High Similarity	NPC470890
0.9366	High Similarity	NPC319752
0.9366	High Similarity	NPC196137
0.9366	High Similarity	NPC1886
0.9366	High Similarity	NPC271288
0.9366	High Similarity	NPC87486
0.9366	High Similarity	NPC124780
0.9362	High Similarity	NPC161506
0.9362	High Similarity	NPC324436
0.9362	High Similarity	NPC66515
0.9362	High Similarity	NPC328164
0.9362	High Similarity	NPC36181
0.9362	High Similarity	NPC194432
0.9362	High Similarity	NPC306829
0.9362	High Similarity	NPC148757
0.9362	High Similarity	NPC125855
0.9362	High Similarity	NPC296917
0.9362	High Similarity	NPC324134
0.9362	High Similarity	NPC32739
0.9362	High Similarity	NPC166934
0.9362	High Similarity	NPC182852
0.9362	High Similarity	NPC220998
0.9362	High Similarity	NPC228504
0.9362	High Similarity	NPC204469
0.9362	High Similarity	NPC37496
0.9362	High Similarity	NPC64915
0.9362	High Similarity	NPC167624
0.9362	High Similarity	NPC107572
0.9362	High Similarity	NPC227579
0.9362	High Similarity	NPC10937
0.9362	High Similarity	NPC40833
0.9362	High Similarity	NPC265040
0.9362	High Similarity	NPC76338
0.9362	High Similarity	NPC223500
0.9362	High Similarity	NPC1089
0.9362	High Similarity	NPC78
0.9362	High Similarity	NPC166482
0.9362	High Similarity	NPC177354
0.9362	High Similarity	NPC76372
0.9357	High Similarity	NPC215311
0.9357	High Similarity	NPC172250
0.9357	High Similarity	NPC144118
0.9357	High Similarity	NPC259166
0.9357	High Similarity	NPC219917
0.9357	High Similarity	NPC326109
0.9357	High Similarity	NPC80962
0.9357	High Similarity	NPC213659
0.9357	High Similarity	NPC48624
0.9357	High Similarity	NPC204985
0.9353	High Similarity	NPC470669
0.9353	High Similarity	NPC131130
0.9353	High Similarity	NPC470668
0.9348	High Similarity	NPC194281
0.9348	High Similarity	NPC29353
0.9348	High Similarity	NPC47815
0.9348	High Similarity	NPC174999
0.9348	High Similarity	NPC473887
0.9348	High Similarity	NPC124784
0.9348	High Similarity	NPC127447
0.9348	High Similarity	NPC231772
0.9348	High Similarity	NPC234133
0.9343	High Similarity	NPC248872
0.932	High Similarity	NPC217706
0.932	High Similarity	NPC476169
0.932	High Similarity	NPC304745
0.932	High Similarity	NPC207809
0.932	High Similarity	NPC304207
0.932	High Similarity	NPC111341
0.932	High Similarity	NPC275575
0.932	High Similarity	NPC259710
0.932	High Similarity	NPC48579
0.932	High Similarity	NPC133392
0.9315	High Similarity	NPC35567

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 NPC24821 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	402
0.1-0.2	981
0.2-0.3	1690
0.3-0.4	2727
0.4-0.5	1817
0.5-0.6	1017
0.6-0.7	344
0.7-0.8	101
0.8-0.85	51
0.85-0.9	14
0.9-0.95	5
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9928	High Similarity	NPD4378	Clinical (unspecified phase)
0.9231	High Similarity	NPD7410	Clinical (unspecified phase)
0.9034	High Similarity	NPD1512	Approved
0.9007	High Similarity	NPD1552	Clinical (unspecified phase)
0.9007	High Similarity	NPD1550	Clinical (unspecified phase)
0.9	High Similarity	NPD1510	Phase 2
0.8993	High Similarity	NPD2393	Clinical (unspecified phase)
0.8944	High Similarity	NPD1549	Phase 2
0.894	High Similarity	NPD7075	Discontinued
0.8936	High Similarity	NPD2796	Approved
0.8919	High Similarity	NPD4380	Phase 2
0.8897	High Similarity	NPD1511	Approved
0.8867	High Similarity	NPD7096	Clinical (unspecified phase)
0.8849	High Similarity	NPD1240	Approved
0.8808	High Similarity	NPD8443	Clinical (unspecified phase)
0.88	High Similarity	NPD6801	Discontinued
0.8742	High Similarity	NPD2801	Approved
0.8733	High Similarity	NPD7411	Suspended
0.8723	High Similarity	NPD1607	Approved
0.8675	High Similarity	NPD1934	Approved
0.8671	High Similarity	NPD7804	Clinical (unspecified phase)
0.8639	High Similarity	NPD6799	Approved
0.8621	High Similarity	NPD2800	Approved
0.8618	High Similarity	NPD7819	Suspended
0.8571	High Similarity	NPD4381	Clinical (unspecified phase)
0.8562	High Similarity	NPD3750	Approved
0.8562	High Similarity	NPD3817	Phase 2
0.8506	High Similarity	NPD3882	Suspended
0.8481	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8481	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8481	Intermediate Similarity	NPD6166	Phase 2
0.8421	Intermediate Similarity	NPD6599	Discontinued
0.8408	Intermediate Similarity	NPD6959	Discontinued
0.8387	Intermediate Similarity	NPD7768	Phase 2
0.8367	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8367	Intermediate Similarity	NPD1243	Approved
0.8365	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.831	Intermediate Similarity	NPD2313	Discontinued
0.8299	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8288	Intermediate Similarity	NPD2935	Discontinued
0.8224	Intermediate Similarity	NPD920	Approved
0.8224	Intermediate Similarity	NPD5403	Approved
0.8221	Intermediate Similarity	NPD6797	Phase 2
0.8219	Intermediate Similarity	NPD2799	Discontinued
0.8219	Intermediate Similarity	NPD3748	Approved
0.8217	Intermediate Similarity	NPD3749	Approved
0.8207	Intermediate Similarity	NPD6651	Approved
0.8182	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8171	Intermediate Similarity	NPD7251	Discontinued
0.8163	Intermediate Similarity	NPD1551	Phase 2
0.8148	Intermediate Similarity	NPD3818	Discontinued
0.8125	Intermediate Similarity	NPD6232	Discontinued
0.8121	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.8121	Intermediate Similarity	NPD7808	Phase 3
0.8113	Intermediate Similarity	NPD5494	Approved
0.8108	Intermediate Similarity	NPD2344	Approved
0.8098	Intermediate Similarity	NPD7054	Approved
0.8092	Intermediate Similarity	NPD2534	Approved
0.8092	Intermediate Similarity	NPD5401	Approved
0.8092	Intermediate Similarity	NPD2533	Approved
0.8092	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.8092	Intermediate Similarity	NPD2532	Approved
0.8089	Intermediate Similarity	NPD5402	Approved
0.8086	Intermediate Similarity	NPD7473	Discontinued
0.8079	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.8049	Intermediate Similarity	NPD7074	Phase 3
0.8049	Intermediate Similarity	NPD7472	Approved
0.8012	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD3226	Approved
0.8	Intermediate Similarity	NPD5953	Discontinued
0.7988	Intermediate Similarity	NPD7286	Phase 2
0.7973	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7958	Intermediate Similarity	NPD1203	Approved
0.7952	Intermediate Similarity	NPD6559	Discontinued
0.795	Intermediate Similarity	NPD1247	Approved
0.7947	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7937	Intermediate Similarity	NPD919	Approved
0.7931	Intermediate Similarity	NPD3268	Approved
0.7931	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7925	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7919	Intermediate Similarity	NPD6099	Approved
0.7919	Intermediate Similarity	NPD6100	Approved
0.7908	Intermediate Similarity	NPD7390	Discontinued
0.7902	Intermediate Similarity	NPD2798	Approved
0.7895	Intermediate Similarity	NPD2309	Approved
0.7867	Intermediate Similarity	NPD2346	Discontinued
0.7832	Intermediate Similarity	NPD2797	Approved
0.7823	Intermediate Similarity	NPD943	Approved
0.7801	Intermediate Similarity	NPD422	Phase 1
0.7793	Intermediate Similarity	NPD4908	Phase 1
0.7771	Intermediate Similarity	NPD5844	Phase 1
0.777	Intermediate Similarity	NPD1548	Phase 1
0.7759	Intermediate Similarity	NPD4360	Phase 2
0.7759	Intermediate Similarity	NPD4363	Phase 3
0.7746	Intermediate Similarity	NPD9717	Approved
0.7744	Intermediate Similarity	NPD3926	Phase 2
0.7733	Intermediate Similarity	NPD4308	Phase 3
0.7733	Intermediate Similarity	NPD7033	Discontinued
0.7712	Intermediate Similarity	NPD4628	Phase 3
0.7712	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7679	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7676	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7676	Intermediate Similarity	NPD1610	Phase 2
0.7671	Intermediate Similarity	NPD6832	Phase 2
0.767	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7639	Intermediate Similarity	NPD3225	Approved
0.7619	Intermediate Similarity	NPD4625	Phase 3
0.7614	Intermediate Similarity	NPD4361	Phase 2
0.7614	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD3266	Approved
0.7586	Intermediate Similarity	NPD3267	Approved
0.7578	Intermediate Similarity	NPD1465	Phase 2
0.7562	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7551	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7533	Intermediate Similarity	NPD5124	Phase 1
0.7533	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD2654	Approved
0.7531	Intermediate Similarity	NPD4288	Approved
0.7516	Intermediate Similarity	NPD1471	Phase 3
0.75	Intermediate Similarity	NPD1608	Approved
0.75	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.747	Intermediate Similarity	NPD5710	Approved
0.747	Intermediate Similarity	NPD5711	Approved
0.7467	Intermediate Similarity	NPD4307	Phase 2
0.745	Intermediate Similarity	NPD1296	Phase 2
0.745	Intermediate Similarity	NPD6798	Discontinued
0.7443	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7431	Intermediate Similarity	NPD1201	Approved
0.7421	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7417	Intermediate Similarity	NPD447	Suspended
0.7417	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7412	Intermediate Similarity	NPD1729	Discontinued
0.7381	Intermediate Similarity	NPD2403	Approved
0.7379	Intermediate Similarity	NPD3972	Approved
0.7365	Intermediate Similarity	NPD7229	Phase 3
0.7358	Intermediate Similarity	NPD5049	Phase 3
0.7351	Intermediate Similarity	NPD1613	Approved
0.7351	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD1164	Approved
0.7347	Intermediate Similarity	NPD1470	Approved
0.7338	Intermediate Similarity	NPD5405	Approved
0.7338	Intermediate Similarity	NPD5406	Approved
0.7338	Intermediate Similarity	NPD5408	Approved
0.7338	Intermediate Similarity	NPD5404	Approved
0.7333	Intermediate Similarity	NPD411	Approved
0.7333	Intermediate Similarity	NPD3764	Approved
0.7329	Intermediate Similarity	NPD4749	Approved
0.7329	Intermediate Similarity	NPD7458	Discontinued
0.7325	Intermediate Similarity	NPD2354	Approved
0.7317	Intermediate Similarity	NPD2296	Approved
0.7303	Intermediate Similarity	NPD230	Phase 1
0.7303	Intermediate Similarity	NPD6355	Discontinued
0.7303	Intermediate Similarity	NPD1933	Approved
0.7297	Intermediate Similarity	NPD7584	Approved
0.7296	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7294	Intermediate Similarity	NPD3751	Discontinued
0.7292	Intermediate Similarity	NPD17	Approved
0.729	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7285	Intermediate Similarity	NPD6233	Phase 2
0.7284	Intermediate Similarity	NPD6585	Discontinued
0.7278	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD9545	Approved
0.7262	Intermediate Similarity	NPD3787	Discontinued
0.7261	Intermediate Similarity	NPD7003	Approved
0.726	Intermediate Similarity	NPD1481	Phase 2
0.7254	Intermediate Similarity	NPD9493	Approved
0.7253	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD5890	Approved
0.7239	Intermediate Similarity	NPD5889	Approved
0.7237	Intermediate Similarity	NPD4060	Phase 1
0.7233	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7232	Intermediate Similarity	NPD4287	Approved
0.7222	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7216	Intermediate Similarity	NPD8434	Phase 2
0.7195	Intermediate Similarity	NPD6844	Discontinued
0.7192	Intermediate Similarity	NPD1535	Discovery
0.7181	Intermediate Similarity	NPD1019	Discontinued
0.7179	Intermediate Similarity	NPD2353	Approved
0.7179	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.7163	Intermediate Similarity	NPD1241	Discontinued
0.7158	Intermediate Similarity	NPD6778	Approved
0.7158	Intermediate Similarity	NPD6781	Approved
0.7158	Intermediate Similarity	NPD6782	Approved
0.7158	Intermediate Similarity	NPD6776	Approved
0.7158	Intermediate Similarity	NPD6780	Approved
0.7158	Intermediate Similarity	NPD6779	Approved
0.7158	Intermediate Similarity	NPD6777	Approved
0.7152	Intermediate Similarity	NPD3027	Phase 3
0.7143	Intermediate Similarity	NPD8312	Approved
0.7143	Intermediate Similarity	NPD8313	Approved
0.7134	Intermediate Similarity	NPD2424	Discontinued
0.7133	Intermediate Similarity	NPD2861	Phase 2
0.7126	Intermediate Similarity	NPD6104	Discontinued
0.7115	Intermediate Similarity	NPD4477	Approved
0.7115	Intermediate Similarity	NPD4476	Approved
0.7107	Intermediate Similarity	NPD3887	Approved
0.7105	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7103	Intermediate Similarity	NPD4196	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