NPASS Compound

Structure

CID268204 OpenBabel06191716072D 26 28 0 0 0 0 0 0 0 0999 V2000 -5.1962 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -0.5000 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 -3.4641 0.0000 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 2.5981 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 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 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 1.7321 -0.0000 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 1.7321 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 -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 -1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 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 0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -2.0000 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 5 1 0 0 0 0 3 10 2 0 0 0 0 4 6 2 0 0 0 0 4 11 1 0 0 0 0 5 13 1 0 0 0 0 6 12 1 0 0 0 0 7 11 2 0 0 0 0 7 15 1 0 0 0 0 8 16 2 0 0 0 0 8 17 1 0 0 0 0 9 14 2 0 0 0 0 9 26 1 0 0 0 0 11 21 1 0 0 0 0 12 14 1 0 0 0 0 12 15 2 0 0 0 0 13 16 1 0 0 0 0 13 19 2 0 0 0 0 14 20 1 0 0 0 0 15 22 1 0 0 0 0 16 23 1 0 0 0 0 17 18 2 0 0 0 0 17 26 1 0 0 0 0 18 19 1 0 0 0 0 18 20 1 0 0 0 0 19 24 1 0 0 0 0 20 25 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	354.11
Volume:	357.82
LogP:	4.455
LogD:	2.619
LogS:	-3.175
# 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:	2.88
Fsp3:	0.15
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.891
MDCK Permeability:	9.425599273527041e-06
Pgp-inhibitor:	0.012
Pgp-substrate:	0.596
Human Intestinal Absorption (HIA):	0.01
20% Bioavailability (F20%):	0.937
30% Bioavailability (F30%):	0.975

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.004
Plasma Protein Binding (PPB):	96.73332214355469%
Volume Distribution (VD):	0.595
Pgp-substrate:	3.400681257247925%

ADMET: Metabolism

CYP1A2-inhibitor:	0.897
CYP1A2-substrate:	0.164
CYP2C19-inhibitor:	0.767
CYP2C19-substrate:	0.049
CYP2C9-inhibitor:	0.829
CYP2C9-substrate:	0.869
CYP2D6-inhibitor:	0.865
CYP2D6-substrate:	0.304
CYP3A4-inhibitor:	0.284
CYP3A4-substrate:	0.075

ADMET: Excretion

Clearance (CL):	8.389
Half-life (T1/2):	0.828

ADMET: Toxicity

hERG Blockers:	0.024
Human Hepatotoxicity (H-HT):	0.308
Drug-inuced Liver Injury (DILI):	0.663
AMES Toxicity:	0.104
Rat Oral Acute Toxicity:	0.298
Maximum Recommended Daily Dose:	0.149
Skin Sensitization:	0.93
Carcinogencity:	0.102
Eye Corrosion:	0.003
Eye Irritation:	0.896
Respiratory Toxicity:	0.081

Download Data

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

Natural Product: NPC268204

Natural Product ID:	NPC268204
*Common Name:**	Uncinanone A
IUPAC Name:	3-(2,4-dihydroxyphenyl)-5,7-dihydroxy-6-(3-methylbut-2-enyl)chromen-4-one
Synonyms:
Standard InCHIKey:	MMPVAPMCVABQPS-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C20H18O6/c1-10(2)3-5-13-16(23)8-17-18(19(13)24)20(25)14(9-26-17)12-6-4-11(21)7-15(12)22/h3-4,6-9,21-24H,5H2,1-2H3
SMILES:	CC(=CCc1c(cc2c(c1O)c(=O)c(co2)c1ccc(cc1O)O)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL549617
PubChem CID:	5281797
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002506] Isoflavonoids [CHEMONTID:0001612] Isoflavans [CHEMONTID:0001827] Isoflavanones [CHEMONTID:0003526] 6-prenylated isoflavanones

*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]
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]
NPO11451	Lespedeza cyrtobotrya	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19102656]
NPO3152	Morella rubra	Species	Myricaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19407970]
NPO3152	Morella rubra	Species	Myricaceae	Eukaryota	n.a.	bark	n.a.	PMID[21553897]
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]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	rhizome	n.a.	PMID[23867078]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	root	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]
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]
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]
NPO1468	Crassostrea virginica	Species	Ostreidae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO24342	Lupinus albus	Species	Fabaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO24342	Lupinus albus	Species	Fabaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO17334	Onopordum acanthium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21170	Embelia parviflora	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18176	Ephedra sinica	Species	Ephedraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11451	Lespedeza cyrtobotrya	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]
NPO12056	Chondrodendron tomentosum	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO20598	Lythrum salicaria	Species	Lythraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7154	Glycyrrhiza uralensis	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]
NPO24342	Lupinus albus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18176	Ephedra sinica	Species	Ephedraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20680	Erythrina melanacantha	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3152	Morella rubra	Species	Myricaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11451	Lespedeza cyrtobotrya	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20879	Clerodendrum bungei	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18286	Lycogala epidendrum	Species	Enteridiidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21170	Embelia parviflora	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24342	Lupinus albus	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]
NPO20598	Lythrum salicaria	Species	Lythraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20489	Epilobium hirsutum	Species	Onagraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12056	Chondrodendron tomentosum	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17334	Onopordum acanthium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18668	Asimina parviflora	Species	Annonaceae	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[TCM_Taiwan]
NPO19231	Sophora flavescens	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]
NPO18176	Ephedra sinica	Species	Ephedraceae	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]
NPO20598	Lythrum salicaria	Species	Lythraceae	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]
NPO24342	Lupinus albus	Species	Fabaceae	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]
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]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO17334	Onopordum acanthium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18473	Plathymenia reticulata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16141	Piper regnellii	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19511	Dolabella californica	Species	Aplysiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13449	Syzygium polycephaloides	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21631	Faramea salicifolia	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17560	Pancratium sickenbergeri	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5903	Conus mus	Species	Conidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21170	Embelia parviflora	Species	Primulaceae	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]
NPO3152	Morella rubra	Species	Myricaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20843	Monsonia senegalensis	Species	Geraniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20879	Clerodendrum bungei	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20084	Atraphaxis spinosa	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19036	Esenbeckia leiocarpa	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20142	Embelia schimperi	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1077	Piper dilatatum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14241	Planchonia grandis	Species	Asterolecaniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16569	Gymnocalycium schickendantzii	Species	Cactaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21038	Lemaireocereus longispinus	Species	Cactaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12056	Chondrodendron tomentosum	Species	Menispermaceae	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]
NPO18866	Pteridium esculentum	Species	Dennstaedtiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20489	Epilobium hirsutum	Species	Onagraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6679	Tephrosia watsoniana	Species	Geometridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28202	Helichrysum tenuifolium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17258	Rhinella marina	Species	Bufonidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21375	Euphorbia nematocypha	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17849	Centaurea maculosa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19667	Hypericum styphelioides	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18668	Asimina parviflora	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20680	Erythrina melanacantha	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27367	Latrunculia magnifica	Species	Latrunculiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4051	Tricholoma columbetta	Species	Tricholomataceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18143	Dendronephthya griffini	Species	Nephtheidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12313	Haplophyllum obtusifolium	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19995	Baccharis neglecta	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22961	Cordia leucocephala	Species	Cordiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21562	Diospyros assimilis	Species	Ebenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11523	Erysimum leptophyllum	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20624	Simarouba glauca	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1468	Crassostrea virginica	Species	Ostreidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6060	Amaranthus spinosus	Species	Amaranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18286	Lycogala epidendrum	Species	Enteridiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28072	Theonella conica	Species	Theonellidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21243	Siphonaria capensis	Species	Siphonariidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22937	Vernonia fagifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9968	Shigella dysenteriae	Species	Enterobacteriaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO2610	Chionodoxa gigantea	n.a.	n.a.	n.a.	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]
NPO24342	Lupinus albus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21495	Abelia chinensis	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2419	Macrocentrus cingulum	Species	Braconidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11451	Lespedeza cyrtobotrya	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20598	Lythrum salicaria	Species	Lythraceae	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	1
Others	2

Activity Type	# Activity
Individual Protein	1
Organism	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT152	Individual Protein	Nuclear factor erythroid 2-related factor 2	Homo sapiens	FC	=	6.68	n.a.	PMID[546267]
NPT2	Others	Unspecified		IC50	=	5400.0	nM	PMID[546266]
NPT742	Organism	Influenza A virus	Influenza A virus	Activity	>	30.0	%	PMID[546267]

☑ 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 NPC268204 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	396
0.1-0.2	1708
0.2-0.3	4023
0.3-0.4	10283
0.4-0.5	8083
0.5-0.6	3814
0.6-0.7	5542
0.7-0.8	4528
0.8-0.85	1978
0.85-0.9	1719
0.9-0.95	523
0.95-1	100

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC52789
1.0	High Similarity	NPC26051
1.0	High Similarity	NPC55832
0.9926	High Similarity	NPC48624
0.9926	High Similarity	NPC80962
0.9926	High Similarity	NPC253822
0.9926	High Similarity	NPC219917
0.9926	High Similarity	NPC215311
0.9926	High Similarity	NPC101366
0.9926	High Similarity	NPC259166
0.9926	High Similarity	NPC213659
0.9926	High Similarity	NPC326109
0.9926	High Similarity	NPC172250
0.9926	High Similarity	NPC144118
0.9926	High Similarity	NPC204985
0.9853	High Similarity	NPC469404
0.9852	High Similarity	NPC283429
0.9852	High Similarity	NPC295384
0.9783	High Similarity	NPC476055
0.9778	High Similarity	NPC12175
0.9778	High Similarity	NPC279668
0.9778	High Similarity	NPC90665
0.9778	High Similarity	NPC55162
0.9778	High Similarity	NPC309154
0.9778	High Similarity	NPC278323
0.971	High Similarity	NPC475705
0.971	High Similarity	NPC476178
0.971	High Similarity	NPC51887
0.971	High Similarity	NPC117836
0.9706	High Similarity	NPC477956
0.9704	High Similarity	NPC7013
0.9704	High Similarity	NPC294409
0.9704	High Similarity	NPC472419
0.9704	High Similarity	NPC303644
0.9704	High Similarity	NPC181124
0.9704	High Similarity	NPC116632
0.9704	High Similarity	NPC209560
0.9704	High Similarity	NPC162680
0.964	High Similarity	NPC311741
0.964	High Similarity	NPC234629
0.9632	High Similarity	NPC21350
0.963	High Similarity	NPC41461
0.963	High Similarity	NPC87545
0.963	High Similarity	NPC66349
0.963	High Similarity	NPC477243
0.963	High Similarity	NPC477244
0.963	High Similarity	NPC186838
0.963	High Similarity	NPC25287
0.963	High Similarity	NPC12165
0.963	High Similarity	NPC98115
0.963	High Similarity	NPC249606
0.963	High Similarity	NPC235428
0.963	High Similarity	NPC150399
0.963	High Similarity	NPC168105
0.963	High Similarity	NPC1486
0.963	High Similarity	NPC477242
0.963	High Similarity	NPC274109
0.9574	High Similarity	NPC266572
0.9565	High Similarity	NPC470089
0.9565	High Similarity	NPC321980
0.9565	High Similarity	NPC470087
0.9565	High Similarity	NPC110969
0.9562	High Similarity	NPC470211
0.9559	High Similarity	NPC317119
0.9559	High Similarity	NPC153979
0.9556	High Similarity	NPC39426
0.9556	High Similarity	NPC234560
0.9556	High Similarity	NPC156092
0.9556	High Similarity	NPC13575
0.9556	High Similarity	NPC131039
0.9507	High Similarity	NPC317492
0.9504	High Similarity	NPC222298
0.9504	High Similarity	NPC51070
0.9504	High Similarity	NPC201731
0.9504	High Similarity	NPC24673
0.9504	High Similarity	NPC97716
0.9504	High Similarity	NPC79469
0.9504	High Similarity	NPC104406
0.9504	High Similarity	NPC237635
0.9496	High Similarity	NPC11561
0.9496	High Similarity	NPC226636
0.9493	High Similarity	NPC159275
0.9493	High Similarity	NPC172986
0.9493	High Similarity	NPC270883
0.9493	High Similarity	NPC261227
0.9493	High Similarity	NPC241100
0.9493	High Similarity	NPC11056
0.9489	High Similarity	NPC243528
0.9489	High Similarity	NPC471620
0.9489	High Similarity	NPC251681
0.9481	High Similarity	NPC103842
0.9481	High Similarity	NPC286336
0.9437	High Similarity	NPC39195
0.9437	High Similarity	NPC6511
0.9437	High Similarity	NPC168085
0.9429	High Similarity	NPC301751
0.9429	High Similarity	NPC149026
0.9429	High Similarity	NPC143896
0.9429	High Similarity	NPC91560
0.9429	High Similarity	NPC245482
0.9429	High Similarity	NPC106985
0.9429	High Similarity	NPC75049
0.9429	High Similarity	NPC18585
0.9429	High Similarity	NPC39329
0.9429	High Similarity	NPC310130
0.9429	High Similarity	NPC169591
0.9429	High Similarity	NPC175504
0.9429	High Similarity	NPC257097
0.9429	High Similarity	NPC68104
0.9429	High Similarity	NPC166138
0.9429	High Similarity	NPC150408
0.9429	High Similarity	NPC164980
0.9429	High Similarity	NPC221432
0.9424	High Similarity	NPC205006
0.9424	High Similarity	NPC147688
0.9424	High Similarity	NPC3188
0.9424	High Similarity	NPC64908
0.9424	High Similarity	NPC282300
0.9424	High Similarity	NPC156590
0.9424	High Similarity	NPC103362
0.9424	High Similarity	NPC118840
0.942	High Similarity	NPC53181
0.942	High Similarity	NPC220062
0.942	High Similarity	NPC217186
0.942	High Similarity	NPC18260
0.942	High Similarity	NPC216978
0.942	High Similarity	NPC472366
0.942	High Similarity	NPC55018
0.942	High Similarity	NPC303633
0.942	High Similarity	NPC78913
0.942	High Similarity	NPC96565
0.942	High Similarity	NPC301217
0.9416	High Similarity	NPC212767
0.9407	High Similarity	NPC312318
0.9407	High Similarity	NPC159623
0.9407	High Similarity	NPC337373
0.9407	High Similarity	NPC144051
0.9407	High Similarity	NPC82225
0.9407	High Similarity	NPC28753
0.9407	High Similarity	NPC175098
0.9407	High Similarity	NPC56031
0.9407	High Similarity	NPC263670
0.9407	High Similarity	NPC223354
0.9407	High Similarity	NPC188646
0.9407	High Similarity	NPC204960
0.9407	High Similarity	NPC18877
0.9407	High Similarity	NPC192304
0.9407	High Similarity	NPC472365
0.9407	High Similarity	NPC20560
0.9407	High Similarity	NPC139813
0.9407	High Similarity	NPC294593
0.9407	High Similarity	NPC242294
0.9407	High Similarity	NPC27643
0.9371	High Similarity	NPC38545
0.9371	High Similarity	NPC171916
0.9366	High Similarity	NPC110303
0.9366	High Similarity	NPC308200
0.9366	High Similarity	NPC296998
0.9366	High Similarity	NPC473077
0.9366	High Similarity	NPC23728
0.9362	High Similarity	NPC216538
0.9362	High Similarity	NPC319752
0.9362	High Similarity	NPC271288
0.9362	High Similarity	NPC273538
0.9362	High Similarity	NPC224714
0.9362	High Similarity	NPC197252
0.9362	High Similarity	NPC209040
0.9362	High Similarity	NPC473013
0.9362	High Similarity	NPC236766
0.9362	High Similarity	NPC473015
0.9357	High Similarity	NPC182852
0.9357	High Similarity	NPC37496
0.9357	High Similarity	NPC167624
0.9357	High Similarity	NPC40833
0.9357	High Similarity	NPC107572
0.9357	High Similarity	NPC227579
0.9357	High Similarity	NPC76338
0.9357	High Similarity	NPC223500
0.9357	High Similarity	NPC1089
0.9357	High Similarity	NPC265040
0.9357	High Similarity	NPC78
0.9357	High Similarity	NPC297600
0.9357	High Similarity	NPC66515
0.9357	High Similarity	NPC76372
0.9357	High Similarity	NPC32739
0.9357	High Similarity	NPC324436
0.9357	High Similarity	NPC161506
0.9357	High Similarity	NPC148545
0.9357	High Similarity	NPC177354
0.9357	High Similarity	NPC64915
0.9357	High Similarity	NPC328164
0.9357	High Similarity	NPC306829
0.9357	High Similarity	NPC194432
0.9357	High Similarity	NPC144499
0.9357	High Similarity	NPC10937
0.9357	High Similarity	NPC148757
0.9357	High Similarity	NPC125855
0.9357	High Similarity	NPC166482
0.9357	High Similarity	NPC296917
0.9357	High Similarity	NPC324134

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 NPC268204 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	367
0.1-0.2	958
0.2-0.3	1547
0.3-0.4	2621
0.4-0.5	1956
0.5-0.6	1131
0.6-0.7	372
0.7-0.8	123
0.8-0.85	45
0.85-0.9	26
0.9-0.95	3
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9556	High Similarity	NPD1510	Phase 2
0.9362	High Similarity	NPD4378	Clinical (unspecified phase)
0.9259	High Similarity	NPD1240	Approved
0.9172	High Similarity	NPD4380	Phase 2
0.9124	High Similarity	NPD1607	Approved
0.9091	High Similarity	NPD7410	Clinical (unspecified phase)
0.9071	High Similarity	NPD1549	Phase 2
0.9065	High Similarity	NPD2796	Approved
0.9	High Similarity	NPD1550	Clinical (unspecified phase)
0.9	High Similarity	NPD1552	Clinical (unspecified phase)
0.8859	High Similarity	NPD2393	Clinical (unspecified phase)
0.8851	High Similarity	NPD7411	Suspended
0.8808	High Similarity	NPD7075	Discontinued
0.88	High Similarity	NPD8443	Clinical (unspecified phase)
0.8733	High Similarity	NPD7819	Suspended
0.8733	High Similarity	NPD7096	Clinical (unspecified phase)
0.8667	High Similarity	NPD6801	Discontinued
0.8609	High Similarity	NPD2801	Approved
0.8562	High Similarity	NPD4381	Clinical (unspecified phase)
0.8552	High Similarity	NPD1878	Clinical (unspecified phase)
0.8543	High Similarity	NPD1934	Approved
0.8531	High Similarity	NPD2935	Discontinued
0.8503	High Similarity	NPD1511	Approved
0.8503	High Similarity	NPD6799	Approved
0.8497	Intermediate Similarity	NPD3882	Suspended
0.8497	Intermediate Similarity	NPD7768	Phase 2
0.8483	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8471	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8451	Intermediate Similarity	NPD6651	Approved
0.8425	Intermediate Similarity	NPD3750	Approved
0.8414	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8389	Intermediate Similarity	NPD1512	Approved
0.8356	Intermediate Similarity	NPD2800	Approved
0.8344	Intermediate Similarity	NPD6232	Discontinued
0.8333	Intermediate Similarity	NPD920	Approved
0.8333	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.8322	Intermediate Similarity	NPD2533	Approved
0.8322	Intermediate Similarity	NPD2534	Approved
0.8322	Intermediate Similarity	NPD2532	Approved
0.8313	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8302	Intermediate Similarity	NPD7473	Discontinued
0.8289	Intermediate Similarity	NPD6599	Discontinued
0.828	Intermediate Similarity	NPD6959	Discontinued
0.8276	Intermediate Similarity	NPD1551	Phase 2
0.825	Intermediate Similarity	NPD3818	Discontinued
0.8231	Intermediate Similarity	NPD1243	Approved
0.8217	Intermediate Similarity	NPD5494	Approved
0.821	Intermediate Similarity	NPD5953	Discontinued
0.8207	Intermediate Similarity	NPD2799	Discontinued
0.8205	Intermediate Similarity	NPD3749	Approved
0.82	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.8194	Intermediate Similarity	NPD3817	Phase 2
0.8188	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.8182	Intermediate Similarity	NPD943	Approved
0.8169	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8169	Intermediate Similarity	NPD2313	Discontinued
0.8143	Intermediate Similarity	NPD2798	Approved
0.8125	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8125	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8125	Intermediate Similarity	NPD6166	Phase 2
0.811	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.8095	Intermediate Similarity	NPD2344	Approved
0.8092	Intermediate Similarity	NPD5403	Approved
0.8086	Intermediate Similarity	NPD7286	Phase 2
0.8082	Intermediate Similarity	NPD3748	Approved
0.8025	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7975	Intermediate Similarity	NPD7054	Approved
0.7962	Intermediate Similarity	NPD5402	Approved
0.7961	Intermediate Similarity	NPD5401	Approved
0.7939	Intermediate Similarity	NPD6559	Discontinued
0.7927	Intermediate Similarity	NPD7074	Phase 3
0.7927	Intermediate Similarity	NPD7472	Approved
0.7917	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7895	Intermediate Similarity	NPD7390	Discontinued
0.7881	Intermediate Similarity	NPD2309	Approved
0.7879	Intermediate Similarity	NPD6797	Phase 2
0.7871	Intermediate Similarity	NPD3226	Approved
0.7831	Intermediate Similarity	NPD7251	Discontinued
0.7826	Intermediate Similarity	NPD1247	Approved
0.7817	Intermediate Similarity	NPD1203	Approved
0.7815	Intermediate Similarity	NPD4628	Phase 3
0.7812	Intermediate Similarity	NPD919	Approved
0.7786	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7784	Intermediate Similarity	NPD7808	Phase 3
0.7784	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD6832	Phase 2
0.7778	Intermediate Similarity	NPD4908	Phase 1
0.7758	Intermediate Similarity	NPD5844	Phase 1
0.7756	Intermediate Similarity	NPD7458	Discontinued
0.7754	Intermediate Similarity	NPD1548	Phase 1
0.7748	Intermediate Similarity	NPD2654	Approved
0.7742	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7733	Intermediate Similarity	NPD2346	Discontinued
0.773	Intermediate Similarity	NPD3972	Approved
0.7718	Intermediate Similarity	NPD7033	Discontinued
0.7692	Intermediate Similarity	NPD1470	Approved
0.7671	Intermediate Similarity	NPD3268	Approved
0.7669	Intermediate Similarity	NPD5710	Approved
0.7669	Intermediate Similarity	NPD5711	Approved
0.7667	Intermediate Similarity	NPD6100	Approved
0.7667	Intermediate Similarity	NPD6099	Approved
0.766	Intermediate Similarity	NPD1610	Phase 2
0.7644	Intermediate Similarity	NPD4360	Phase 2
0.7644	Intermediate Similarity	NPD4363	Phase 3
0.7635	Intermediate Similarity	NPD230	Phase 1
0.7626	Intermediate Similarity	NPD9545	Approved
0.7622	Intermediate Similarity	NPD3926	Phase 2
0.7609	Intermediate Similarity	NPD9493	Approved
0.7606	Intermediate Similarity	NPD9717	Approved
0.76	Intermediate Similarity	NPD4361	Phase 2
0.76	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD4308	Phase 3
0.7582	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7582	Intermediate Similarity	NPD7003	Approved
0.7569	Intermediate Similarity	NPD1164	Approved
0.7569	Intermediate Similarity	NPD2797	Approved
0.756	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7557	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7551	Intermediate Similarity	NPD3764	Approved
0.755	Intermediate Similarity	NPD5406	Approved
0.755	Intermediate Similarity	NPD5408	Approved
0.755	Intermediate Similarity	NPD5405	Approved
0.755	Intermediate Similarity	NPD5404	Approved
0.7547	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7535	Intermediate Similarity	NPD422	Phase 1
0.7535	Intermediate Similarity	NPD1201	Approved
0.7529	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7517	Intermediate Similarity	NPD5124	Phase 1
0.7517	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1729	Discontinued
0.7483	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7453	Intermediate Similarity	NPD1465	Phase 2
0.743	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD4288	Approved
0.74	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7379	Intermediate Similarity	NPD1876	Approved
0.7379	Intermediate Similarity	NPD3225	Approved
0.7365	Intermediate Similarity	NPD3027	Phase 3
0.7365	Intermediate Similarity	NPD4625	Phase 3
0.7349	Intermediate Similarity	NPD7229	Phase 3
0.7347	Intermediate Similarity	NPD9494	Approved
0.7333	Intermediate Similarity	NPD4307	Phase 2
0.7329	Intermediate Similarity	NPD3266	Approved
0.7329	Intermediate Similarity	NPD5890	Approved
0.7329	Intermediate Similarity	NPD5889	Approved
0.7329	Intermediate Similarity	NPD3267	Approved
0.7325	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7324	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7314	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7301	Intermediate Similarity	NPD2296	Approved
0.7285	Intermediate Similarity	NPD1933	Approved
0.7285	Intermediate Similarity	NPD447	Suspended
0.7284	Intermediate Similarity	NPD6844	Discontinued
0.7284	Intermediate Similarity	NPD37	Approved
0.7283	Intermediate Similarity	NPD7584	Approved
0.7278	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD1471	Phase 3
0.7266	Intermediate Similarity	NPD1241	Discontinued
0.7241	Intermediate Similarity	NPD1608	Approved
0.7238	Intermediate Similarity	NPD6782	Approved
0.7238	Intermediate Similarity	NPD6776	Approved
0.7238	Intermediate Similarity	NPD6780	Approved
0.7238	Intermediate Similarity	NPD6777	Approved
0.7238	Intermediate Similarity	NPD6781	Approved
0.7238	Intermediate Similarity	NPD6778	Approved
0.7238	Intermediate Similarity	NPD6779	Approved
0.7225	Intermediate Similarity	NPD8313	Approved
0.7225	Intermediate Similarity	NPD8312	Approved
0.7219	Intermediate Similarity	NPD1613	Approved
0.7219	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7216	Intermediate Similarity	NPD4287	Approved
0.7209	Intermediate Similarity	NPD6104	Discontinued
0.7203	Intermediate Similarity	NPD1651	Approved
0.72	Intermediate Similarity	NPD411	Approved
0.72	Intermediate Similarity	NPD1296	Phase 2
0.72	Intermediate Similarity	NPD6798	Discontinued
0.7197	Intermediate Similarity	NPD3295	Clinical (unspecified phase)
0.7192	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7178	Intermediate Similarity	NPD6279	Approved
0.7178	Intermediate Similarity	NPD6280	Approved
0.7176	Intermediate Similarity	NPD3751	Discontinued
0.717	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7169	Intermediate Similarity	NPD6234	Discontinued
0.7162	Intermediate Similarity	NPD1019	Discontinued
0.716	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD6585	Discontinued
0.7152	Intermediate Similarity	NPD4965	Approved
0.7152	Intermediate Similarity	NPD4967	Phase 2
0.7152	Intermediate Similarity	NPD4966	Approved
0.7143	Intermediate Similarity	NPD1283	Approved
0.7134	Intermediate Similarity	NPD5761	Phase 2
0.7134	Intermediate Similarity	NPD5760	Phase 2
0.712	Intermediate Similarity	NPD7697	Approved
0.712	Intermediate Similarity	NPD7698	Approved
0.712	Intermediate Similarity	NPD7435	Discontinued
0.712	Intermediate Similarity	NPD7696	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