NPASS Compound

Structure

CID211309 OpenBabel06191716002D 25 28 0 0 0 0 0 0 0 0999 V2000 9.7219 1.7891 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.2219 2.6551 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.2219 0.9230 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2219 0.9230 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7219 0.0570 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6342 -1.6180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 -1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7219 -1.6750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5878 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.7219 1.7891 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7219 0.0570 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2219 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2219 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7219 -1.6750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2219 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.2219 -0.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.2219 -2.5411 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.6180 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 3.6342 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 11 1 0 0 0 0 2 11 1 0 0 0 0 3 4 1 0 0 0 0 3 11 2 0 0 0 0 4 12 1 0 0 0 0 5 12 2 0 0 0 0 5 14 1 0 0 0 0 6 13 1 0 0 0 0 6 18 2 0 0 0 0 7 13 2 0 0 0 0 7 19 1 0 0 0 0 8 15 2 0 0 0 0 8 16 1 0 0 0 0 9 17 2 0 0 0 0 9 20 1 0 0 0 0 10 23 1 0 0 0 0 10 24 1 0 0 0 0 12 15 1 0 0 0 0 13 17 1 0 0 0 0 14 16 2 0 0 0 0 14 18 1 0 0 0 0 15 21 1 0 0 0 0 16 22 1 0 0 0 0 17 25 1 0 0 0 0 18 25 1 0 0 0 0 19 20 2 0 0 0 0 19 23 1 0 0 0 0 20 24 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	338.12
Volume:	343.11
LogP:	5.646
LogD:	3.6
LogS:	-4.728
# Rotatable Bonds:	3
TPSA:	72.06
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.674
Synthetic Accessibility Score:	2.795
Fsp3:	0.2
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.834
MDCK Permeability:	1.5061174053698778e-05
Pgp-inhibitor:	0.274
Pgp-substrate:	0.021
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.864
30% Bioavailability (F30%):	0.99

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.014
Plasma Protein Binding (PPB):	98.81980895996094%
Volume Distribution (VD):	1.529
Pgp-substrate:	3.5191826820373535%

ADMET: Metabolism

CYP1A2-inhibitor:	0.984
CYP1A2-substrate:	0.16
CYP2C19-inhibitor:	0.974
CYP2C19-substrate:	0.061
CYP2C9-inhibitor:	0.808
CYP2C9-substrate:	0.822
CYP2D6-inhibitor:	0.968
CYP2D6-substrate:	0.908
CYP3A4-inhibitor:	0.837
CYP3A4-substrate:	0.112

ADMET: Excretion

Clearance (CL):	15.836
Half-life (T1/2):	0.22

ADMET: Toxicity

hERG Blockers:	0.045
Human Hepatotoxicity (H-HT):	0.272
Drug-inuced Liver Injury (DILI):	0.886
AMES Toxicity:	0.12
Rat Oral Acute Toxicity:	0.103
Maximum Recommended Daily Dose:	0.9
Skin Sensitization:	0.827
Carcinogencity:	0.605
Eye Corrosion:	0.003
Eye Irritation:	0.837
Respiratory Toxicity:	0.726

Download Data

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

Natural Product: NPC211309

Natural Product ID:	NPC211309
*Common Name:**	2-(2,4-Dihydroxy-5-Prenylphenyl)-5,6-Methylenedioxybenzofuran
IUPAC Name:	4-furo[2,3-f][1,3]benzodioxol-6-yl-6-(3-methylbut-2-enyl)benzene-1,3-diol
Synonyms:
Standard InCHIKey:	SOYHFIGRYCLZKD-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C20H18O5/c1-11(2)3-4-12-5-14(16(22)8-15(12)21)18-6-13-7-19-20(24-10-23-19)9-17(13)25-18/h3,5-9,21-22H,4,10H2,1-2H3
SMILES:	CC(=CCc1cc(c(cc1O)O)c1oc2c(c1)cc1c(c2)OCO1)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL524641
PubChem CID:	15953774
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0003405] 2-arylbenzofuran flavonoids

*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	n.a.	leaf	n.a.	PMID[15165152]
NPO19667	Hypericum styphelioides	Species	Hypericaceae	Eukaryota	leaves	n.a.	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]
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	n.a.	root	n.a.	PMID[16933887]
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[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]
NPO3152	Morella rubra	Species	Myricaceae	Eukaryota	n.a.	bark	n.a.	PMID[21553897]
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]
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]
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]
NPO21375	Euphorbia nematocypha	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO20598	Lythrum salicaria	Species	Lythraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18286	Lycogala epidendrum	Species	Enteridiidae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18176	Ephedra sinica	Species	Ephedraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
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]
NPO12056	Chondrodendron tomentosum	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17334	Onopordum acanthium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21375	Euphorbia nematocypha	Species	Euphorbiaceae	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]
NPO20489	Epilobium hirsutum	Species	Onagraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12056	Chondrodendron tomentosum	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20598	Lythrum salicaria	Species	Lythraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18668	Asimina parviflora	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20879	Clerodendrum bungei	Species	Lamiaceae	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]
NPO21170	Embelia parviflora	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20142	Embelia schimperi	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20680	Erythrina melanacantha	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20680	Erythrina melanacantha	Species	Fabaceae	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]
NPO21170	Embelia parviflora	Species	Primulaceae	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]
NPO21375	Euphorbia nematocypha	Species	Euphorbiaceae	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]
NPO19231	Sophora flavescens	Species	Fabaceae	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]
NPO18176	Ephedra sinica	Species	Ephedraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20680	Erythrina melanacantha	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]
NPO4051	Tricholoma columbetta	Species	Tricholomataceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21108	Eria anomala	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12313	Haplophyllum obtusifolium	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13449	Syzygium polycephaloides	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16141	Piper regnellii	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12056	Chondrodendron tomentosum	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21562	Diospyros assimilis	Species	Ebenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14241	Planchonia grandis	Species	Asterolecaniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17560	Pancratium sickenbergeri	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17258	Rhinella marina	Species	Bufonidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18286	Lycogala epidendrum	Species	Enteridiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18866	Pteridium esculentum	Species	Dennstaedtiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19810	Myxococcus stipitatus	Species	Myxococcaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO9968	Shigella dysenteriae	Species	Enterobacteriaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO21495	Abelia chinensis	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18668	Asimina parviflora	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20843	Monsonia senegalensis	Species	Geraniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20624	Simarouba glauca	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17334	Onopordum acanthium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27367	Latrunculia magnifica	Species	Latrunculiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22961	Cordia leucocephala	Species	Cordiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18473	Plathymenia reticulata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19036	Esenbeckia leiocarpa	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19511	Dolabella californica	Species	Aplysiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22937	Vernonia fagifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21631	Faramea salicifolia	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21038	Lemaireocereus longispinus	Species	Cactaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19912	Vellozia nanuzae	Species	Velloziaceae	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]
NPO28202	Helichrysum tenuifolium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3152	Morella rubra	Species	Myricaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19667	Hypericum styphelioides	Species	Hypericaceae	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]
NPO18143	Dendronephthya griffini	Species	Nephtheidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20142	Embelia schimperi	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20598	Lythrum salicaria	Species	Lythraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16569	Gymnocalycium schickendantzii	Species	Cactaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19995	Baccharis neglecta	Species	Asteraceae	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]
NPO20489	Epilobium hirsutum	Species	Onagraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11523	Erysimum leptophyllum	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21375	Euphorbia nematocypha	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17849	Centaurea maculosa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28072	Theonella conica	Species	Theonellidae	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

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	IC50	=	8.0	ug.mL-1	PMID[568658]

☑ 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 NPC211309 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	418
0.1-0.2	1953
0.2-0.3	4637
0.3-0.4	10722
0.4-0.5	7122
0.5-0.6	3865
0.6-0.7	5223
0.7-0.8	5160
0.8-0.85	2419
0.85-0.9	1131
0.9-0.95	45
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9623	High Similarity	NPC110257
0.9394	High Similarity	NPC290304
0.9394	High Similarity	NPC236327
0.939	High Similarity	NPC157522
0.9367	High Similarity	NPC45131
0.925	High Similarity	NPC196879
0.9207	High Similarity	NPC247973
0.9202	High Similarity	NPC187923
0.9198	High Similarity	NPC84515
0.9198	High Similarity	NPC312056
0.9141	High Similarity	NPC133065
0.9136	High Similarity	NPC188486
0.9136	High Similarity	NPC94155
0.913	High Similarity	NPC16935
0.9102	High Similarity	NPC72455
0.9085	High Similarity	NPC36320
0.9085	High Similarity	NPC37183
0.9085	High Similarity	NPC39306
0.908	High Similarity	NPC469575
0.9074	High Similarity	NPC220582
0.9074	High Similarity	NPC304839
0.9068	High Similarity	NPC474990
0.9068	High Similarity	NPC167595
0.9048	High Similarity	NPC66804
0.9042	High Similarity	NPC223375
0.9042	High Similarity	NPC475825
0.9036	High Similarity	NPC41853
0.903	High Similarity	NPC277480
0.9018	High Similarity	NPC162668
0.9012	High Similarity	NPC215375
0.9012	High Similarity	NPC62518
0.9006	High Similarity	NPC261090
0.9	High Similarity	NPC183843
0.8994	High Similarity	NPC170169
0.8988	High Similarity	NPC65885
0.8988	High Similarity	NPC310794
0.8987	High Similarity	NPC178202
0.8976	High Similarity	NPC167479
0.8976	High Similarity	NPC50394
0.897	High Similarity	NPC45449
0.8963	High Similarity	NPC272722
0.8963	High Similarity	NPC81679
0.8963	High Similarity	NPC125991
0.8951	High Similarity	NPC476981
0.8951	High Similarity	NPC36852
0.8951	High Similarity	NPC262286
0.8944	High Similarity	NPC478238
0.8944	High Similarity	NPC18954
0.8938	High Similarity	NPC125300
0.8931	High Similarity	NPC234152
0.8931	High Similarity	NPC230713
0.8931	High Similarity	NPC78335
0.8929	High Similarity	NPC475964
0.8922	High Similarity	NPC471287
0.8909	High Similarity	NPC39305
0.8909	High Similarity	NPC59295
0.8909	High Similarity	NPC470178
0.8909	High Similarity	NPC1706
0.8909	High Similarity	NPC1755
0.8909	High Similarity	NPC263092
0.8902	High Similarity	NPC99968
0.8902	High Similarity	NPC260640
0.8902	High Similarity	NPC295009
0.8889	High Similarity	NPC138243
0.8882	High Similarity	NPC156635
0.8882	High Similarity	NPC183874
0.8882	High Similarity	NPC244371
0.8882	High Similarity	NPC8127
0.8882	High Similarity	NPC49667
0.8882	High Similarity	NPC280937
0.8876	High Similarity	NPC62640
0.8876	High Similarity	NPC261471
0.8869	High Similarity	NPC78830
0.8869	High Similarity	NPC218533
0.8869	High Similarity	NPC131866
0.8869	High Similarity	NPC476641
0.8868	High Similarity	NPC37226
0.8868	High Similarity	NPC226644
0.8862	High Similarity	NPC76482
0.8861	High Similarity	NPC17816
0.8855	High Similarity	NPC291110
0.8855	High Similarity	NPC300053
0.8848	High Similarity	NPC238995
0.8848	High Similarity	NPC273021
0.8848	High Similarity	NPC18284
0.8841	High Similarity	NPC225624
0.8841	High Similarity	NPC285973
0.8841	High Similarity	NPC269906
0.8841	High Similarity	NPC476980
0.8837	High Similarity	NPC97523
0.8834	High Similarity	NPC78225
0.8834	High Similarity	NPC217677
0.8834	High Similarity	NPC165977
0.8834	High Similarity	NPC258644
0.8834	High Similarity	NPC310206
0.8827	High Similarity	NPC198490
0.8827	High Similarity	NPC148938
0.8827	High Similarity	NPC113906
0.8827	High Similarity	NPC3273
0.8824	High Similarity	NPC472607
0.882	High Similarity	NPC292460
0.8817	High Similarity	NPC174700
0.8817	High Similarity	NPC260263
0.8817	High Similarity	NPC292794
0.8812	High Similarity	NPC179183
0.881	High Similarity	NPC247136
0.8802	High Similarity	NPC53640
0.8802	High Similarity	NPC113093
0.8802	High Similarity	NPC119589
0.8795	High Similarity	NPC65846
0.8795	High Similarity	NPC273959
0.8788	High Similarity	NPC258331
0.8788	High Similarity	NPC45124
0.8788	High Similarity	NPC30655
0.8788	High Similarity	NPC74854
0.8788	High Similarity	NPC66288
0.878	High Similarity	NPC195832
0.8773	High Similarity	NPC472461
0.8773	High Similarity	NPC155063
0.8773	High Similarity	NPC68093
0.8773	High Similarity	NPC261484
0.8773	High Similarity	NPC180924
0.8773	High Similarity	NPC191146
0.8765	High Similarity	NPC478213
0.8765	High Similarity	NPC233956
0.8765	High Similarity	NPC82217
0.8765	High Similarity	NPC216842
0.8765	High Similarity	NPC476640
0.8765	High Similarity	NPC57211
0.8765	High Similarity	NPC235333
0.8765	High Similarity	NPC472462
0.8765	High Similarity	NPC37606
0.8765	High Similarity	NPC473834
0.8765	High Similarity	NPC472915
0.8758	High Similarity	NPC226973
0.8758	High Similarity	NPC318424
0.8758	High Similarity	NPC117579
0.8758	High Similarity	NPC58668
0.8758	High Similarity	NPC149614
0.8758	High Similarity	NPC106372
0.8758	High Similarity	NPC308451
0.8758	High Similarity	NPC208043
0.8758	High Similarity	NPC279061
0.8757	High Similarity	NPC44558
0.8757	High Similarity	NPC212748
0.8757	High Similarity	NPC224462
0.8757	High Similarity	NPC105511
0.875	High Similarity	NPC86477
0.875	High Similarity	NPC42892
0.875	High Similarity	NPC328119
0.875	High Similarity	NPC471288
0.8743	High Similarity	NPC470773
0.8743	High Similarity	NPC326520
0.8742	High Similarity	NPC93034
0.8742	High Similarity	NPC119660
0.8742	High Similarity	NPC12148
0.8742	High Similarity	NPC130581
0.8735	High Similarity	NPC472448
0.8735	High Similarity	NPC83922
0.8727	High Similarity	NPC228785
0.8727	High Similarity	NPC474287
0.8727	High Similarity	NPC14353
0.8727	High Similarity	NPC56085
0.8727	High Similarity	NPC475886
0.8727	High Similarity	NPC246478
0.8727	High Similarity	NPC131557
0.8721	High Similarity	NPC67302
0.872	High Similarity	NPC164110
0.872	High Similarity	NPC223787
0.872	High Similarity	NPC212967
0.872	High Similarity	NPC246647
0.872	High Similarity	NPC96342
0.872	High Similarity	NPC76458
0.872	High Similarity	NPC181960
0.872	High Similarity	NPC82733
0.8713	High Similarity	NPC287243
0.8713	High Similarity	NPC227906
0.8712	High Similarity	NPC208197
0.8712	High Similarity	NPC57674
0.8712	High Similarity	NPC213936
0.8712	High Similarity	NPC20830
0.8712	High Similarity	NPC297531
0.8712	High Similarity	NPC130589
0.8712	High Similarity	NPC256612
0.8712	High Similarity	NPC117992
0.8712	High Similarity	NPC230149
0.8712	High Similarity	NPC37392
0.8712	High Similarity	NPC472909
0.8712	High Similarity	NPC152951
0.8712	High Similarity	NPC134287
0.8712	High Similarity	NPC168247
0.8706	High Similarity	NPC230619
0.8706	High Similarity	NPC48773
0.8706	High Similarity	NPC307518
0.8706	High Similarity	NPC54098
0.8706	High Similarity	NPC205076
0.8704	High Similarity	NPC148497
0.8704	High Similarity	NPC35544
0.8704	High Similarity	NPC471982
0.8704	High Similarity	NPC52623

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 NPC211309 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	386
0.1-0.2	979
0.2-0.3	1937
0.3-0.4	2756
0.4-0.5	1705
0.5-0.6	926
0.6-0.7	305
0.7-0.8	119
0.8-0.85	29
0.85-0.9	8
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.875	High Similarity	NPD3818	Discontinued
0.865	High Similarity	NPD2801	Approved
0.8547	High Similarity	NPD6559	Discontinued
0.8545	High Similarity	NPD3882	Suspended
0.8503	High Similarity	NPD5494	Approved
0.8452	Intermediate Similarity	NPD1247	Approved
0.8424	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8364	Intermediate Similarity	NPD1934	Approved
0.8324	Intermediate Similarity	NPD7074	Phase 3
0.8294	Intermediate Similarity	NPD6232	Discontinued
0.8286	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8266	Intermediate Similarity	NPD7054	Approved
0.8256	Intermediate Similarity	NPD7473	Discontinued
0.8246	Intermediate Similarity	NPD3926	Phase 2
0.8225	Intermediate Similarity	NPD919	Approved
0.8218	Intermediate Similarity	NPD7472	Approved
0.8171	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.8166	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8161	Intermediate Similarity	NPD5844	Phase 1
0.816	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8107	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8098	Intermediate Similarity	NPD1511	Approved
0.8092	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8092	Intermediate Similarity	NPD6166	Phase 2
0.8092	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8079	Intermediate Similarity	NPD7808	Phase 3
0.8068	Intermediate Similarity	NPD6797	Phase 2
0.8047	Intermediate Similarity	NPD3817	Phase 2
0.8023	Intermediate Similarity	NPD7251	Discontinued
0.8	Intermediate Similarity	NPD1512	Approved
0.7988	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7963	Intermediate Similarity	NPD1243	Approved
0.7955	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7953	Intermediate Similarity	NPD3749	Approved
0.7953	Intermediate Similarity	NPD7075	Discontinued
0.7952	Intermediate Similarity	NPD920	Approved
0.7939	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7917	Intermediate Similarity	NPD4380	Phase 2
0.7907	Intermediate Similarity	NPD6234	Discontinued
0.7895	Intermediate Similarity	NPD4966	Approved
0.7895	Intermediate Similarity	NPD4967	Phase 2
0.7895	Intermediate Similarity	NPD4965	Approved
0.7888	Intermediate Similarity	NPD2935	Discontinued
0.7882	Intermediate Similarity	NPD7819	Suspended
0.7882	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.787	Intermediate Similarity	NPD7411	Suspended
0.7853	Intermediate Similarity	NPD2800	Approved
0.784	Intermediate Similarity	NPD2344	Approved
0.7831	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7831	Intermediate Similarity	NPD2532	Approved
0.7831	Intermediate Similarity	NPD2534	Approved
0.7831	Intermediate Similarity	NPD2533	Approved
0.7816	Intermediate Similarity	NPD6959	Discontinued
0.7816	Intermediate Similarity	NPD7199	Phase 2
0.7814	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7799	Intermediate Similarity	NPD1240	Approved
0.7791	Intermediate Similarity	NPD1549	Phase 2
0.7778	Intermediate Similarity	NPD1465	Phase 2
0.7771	Intermediate Similarity	NPD6799	Approved
0.7733	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.773	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.773	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7719	Intermediate Similarity	NPD37	Approved
0.7719	Intermediate Similarity	NPD6801	Discontinued
0.7716	Intermediate Similarity	NPD1510	Phase 2
0.7711	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7702	Intermediate Similarity	NPD1607	Approved
0.7688	Intermediate Similarity	NPD7768	Phase 2
0.7684	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7669	Intermediate Similarity	NPD2796	Approved
0.7667	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7651	Intermediate Similarity	NPD2309	Approved
0.763	Intermediate Similarity	NPD5402	Approved
0.7602	Intermediate Similarity	NPD6599	Discontinued
0.7598	Intermediate Similarity	NPD7228	Approved
0.7578	Intermediate Similarity	NPD943	Approved
0.7576	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7554	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.754	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7531	Intermediate Similarity	NPD447	Suspended
0.753	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7423	Intermediate Similarity	NPD1933	Approved
0.7423	Intermediate Similarity	NPD230	Phase 1
0.7403	Intermediate Similarity	NPD3751	Discontinued
0.7394	Intermediate Similarity	NPD2799	Discontinued
0.7384	Intermediate Similarity	NPD1653	Approved
0.7381	Intermediate Similarity	NPD3750	Approved
0.7377	Intermediate Similarity	NPD5953	Discontinued
0.7363	Intermediate Similarity	NPD7286	Phase 2
0.7351	Intermediate Similarity	NPD8312	Approved
0.7351	Intermediate Similarity	NPD8313	Approved
0.7349	Intermediate Similarity	NPD1551	Phase 2
0.7341	Intermediate Similarity	NPD3226	Approved
0.7323	Intermediate Similarity	NPD8151	Discontinued
0.7305	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7289	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD5711	Approved
0.7278	Intermediate Similarity	NPD5710	Approved
0.7278	Intermediate Similarity	NPD3787	Discontinued
0.7273	Intermediate Similarity	NPD6651	Approved
0.7268	Intermediate Similarity	NPD6777	Approved
0.7268	Intermediate Similarity	NPD6779	Approved
0.7268	Intermediate Similarity	NPD6776	Approved
0.7268	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7268	Intermediate Similarity	NPD6778	Approved
0.7268	Intermediate Similarity	NPD6780	Approved
0.7268	Intermediate Similarity	NPD6782	Approved
0.7268	Intermediate Similarity	NPD6781	Approved
0.7251	Intermediate Similarity	NPD7390	Discontinued
0.7243	Intermediate Similarity	NPD7240	Approved
0.7239	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD2313	Discontinued
0.7234	Intermediate Similarity	NPD8434	Phase 2
0.7225	Intermediate Similarity	NPD5403	Approved
0.7208	Intermediate Similarity	NPD7871	Phase 2
0.7208	Intermediate Similarity	NPD7870	Phase 2
0.7204	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD2346	Discontinued
0.7182	Intermediate Similarity	NPD7229	Phase 3
0.7176	Intermediate Similarity	NPD4628	Phase 3
0.7164	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7164	Intermediate Similarity	NPD7783	Phase 2
0.716	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7157	Intermediate Similarity	NPD7697	Approved
0.7157	Intermediate Similarity	NPD7435	Discontinued
0.7157	Intermediate Similarity	NPD7698	Approved
0.7157	Intermediate Similarity	NPD7696	Phase 3
0.7151	Intermediate Similarity	NPD7685	Pre-registration
0.7143	Intermediate Similarity	NPD7458	Discontinued
0.7135	Intermediate Similarity	NPD2296	Approved
0.7128	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.712	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.711	Intermediate Similarity	NPD5401	Approved
0.7083	Intermediate Similarity	NPD3748	Approved
0.7083	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7076	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD3027	Phase 3
0.7068	Intermediate Similarity	NPD4287	Approved
0.705	Intermediate Similarity	NPD7584	Approved
0.7049	Intermediate Similarity	NPD5242	Approved
0.7048	Intermediate Similarity	NPD1613	Approved
0.7048	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD6099	Approved
0.7041	Intermediate Similarity	NPD6100	Approved
0.7037	Intermediate Similarity	NPD1203	Approved
0.702	Intermediate Similarity	NPD5006	Approved
0.702	Intermediate Similarity	NPD5005	Approved
0.702	Intermediate Similarity	NPD6823	Phase 2
0.7015	Intermediate Similarity	NPD7701	Phase 2
0.7011	Intermediate Similarity	NPD2403	Approved
0.701	Intermediate Similarity	NPD6534	Approved
0.701	Intermediate Similarity	NPD6535	Approved
0.7	Intermediate Similarity	NPD1471	Phase 3
0.6994	Remote Similarity	NPD2798	Approved
0.6983	Remote Similarity	NPD8455	Phase 2
0.6952	Remote Similarity	NPD1729	Discontinued
0.6951	Remote Similarity	NPD9494	Approved
0.6946	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD7874	Approved
0.6944	Remote Similarity	NPD5353	Approved
0.6939	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6936	Remote Similarity	NPD6190	Approved
0.6928	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD6279	Approved
0.6927	Remote Similarity	NPD6280	Approved
0.6919	Remote Similarity	NPD2654	Approved
0.6914	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6912	Remote Similarity	NPD7801	Approved
0.691	Remote Similarity	NPD7028	Phase 2
0.6909	Remote Similarity	NPD6832	Phase 2
0.6905	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6904	Remote Similarity	NPD7699	Phase 2
0.6904	Remote Similarity	NPD7700	Phase 2
0.6904	Remote Similarity	NPD4420	Approved
0.6902	Remote Similarity	NPD6808	Phase 2
0.69	Remote Similarity	NPD7680	Approved
0.6889	Remote Similarity	NPD5761	Phase 2
0.6889	Remote Similarity	NPD5760	Phase 2
0.6872	Remote Similarity	NPD6385	Approved
0.6872	Remote Similarity	NPD6386	Approved
0.6869	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD4357	Discontinued
0.6854	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD9269	Phase 2
0.6852	Remote Similarity	NPD9717	Approved
0.6845	Remote Similarity	NPD2163	Approved
0.6842	Remote Similarity	NPD5406	Approved
0.6842	Remote Similarity	NPD5404	Approved
0.6842	Remote Similarity	NPD5408	Approved
0.6842	Remote Similarity	NPD5405	Approved
0.6826	Remote Similarity	NPD3764	Approved
0.6813	Remote Similarity	NPD9268	Approved
0.6807	Remote Similarity	NPD4908	Phase 1
0.6802	Remote Similarity	NPD4362	Clinical (unspecified phase)
0.6802	Remote Similarity	NPD4361	Phase 2

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