NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	222.13
Volume:	240.673
LogP:	1.275
LogD:	1.321
LogS:	-2.5
# Rotatable Bonds:	2
TPSA:	54.37
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	1
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.725
Synthetic Accessibility Score:	3.759
Fsp3:	0.538
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.543
MDCK Permeability:	2.305445377714932e-05
Pgp-inhibitor:	0.007
Pgp-substrate:	0.007
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.001
30% Bioavailability (F30%):	0.001

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.851
Plasma Protein Binding (PPB):	71.56693267822266%
Volume Distribution (VD):	0.396
Pgp-substrate:	21.753337860107422%

ADMET: Metabolism

CYP1A2-inhibitor:	0.024
CYP1A2-substrate:	0.512
CYP2C19-inhibitor:	0.097
CYP2C19-substrate:	0.761
CYP2C9-inhibitor:	0.049
CYP2C9-substrate:	0.164
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.117
CYP3A4-inhibitor:	0.008
CYP3A4-substrate:	0.755

ADMET: Excretion

Clearance (CL):	4.722
Half-life (T1/2):	0.699

ADMET: Toxicity

hERG Blockers:	0.029
Human Hepatotoxicity (H-HT):	0.574
Drug-inuced Liver Injury (DILI):	0.268
AMES Toxicity:	0.546
Rat Oral Acute Toxicity:	0.645
Maximum Recommended Daily Dose:	0.496
Skin Sensitization:	0.887
Carcinogencity:	0.939
Eye Corrosion:	0.557
Eye Irritation:	0.688
Respiratory Toxicity:	0.955

Download Data

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

Natural Product: NPC136473

Natural Product ID:	NPC136473
*Common Name:**	Dehydrovomifoliol
IUPAC Name:	(4S)-4-hydroxy-3,5,5-trimethyl-4-[(E)-3-oxobut-1-enyl]cyclohex-2-en-1-one
Synonyms:	(+)-Dehydrovomifoliol; (6S)-Dehydrovomifoliol
Standard InCHIKey:	JJRYPZMXNLLZFH-URWSZGRFSA-N
Standard InCHI:	InChI=1S/C13H18O3/c1-9-7-11(15)8-12(3,4)13(9,16)6-5-10(2)14/h5-7,16H,8H2,1-4H3/b6-5+/t13-/m1/s1
SMILES:	CC1=CC(=O)CC(C)(C)[C@]1(/C=C/C(=O)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL461278
PubChem CID:	688492
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001550] Sesquiterpenoids

*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
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	Nigeria(latitude 80°N and longitude 4°E)	2005; 2006	DOI[10.1002/ejlt.201000080]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1007/s11306-010-0259-y]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1007/s11306-014-0638-x]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1007/s11746-997-0093-1]
NPO14685	Swertia franchetiana	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/j.bse.2004.02.008]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/j.phytol.2008.07.007]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	Seeds	Plovdiv, Plovdiv region in South Bulgaria		DOI[10.1051/CTV/20163101031]
NPO947	Rauvolfia vomitoria	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1080/01496395.2011.635623]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11170689]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	leaf	n.a.	PMID[11312782]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	fruit	n.a.	PMID[11312782]
NPO15659	Zanthoxylum tetraspermum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11324918]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11408943]
NPO23024	Epimedium koreanum	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12081149]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	fruit	n.a.	PMID[12105962]
NPO26327	Chaenomeles sinensis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[14600382]
NPO16333	Chenopodium album	Species	Chenopodiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15387648]
NPO15063	Leathesia nana	Species	Chordariaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15497936]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15516765]
NPO9516	Gnetum latifolium	Species	Gnetaceae	Eukaryota	stem bark	Veikabu bridge along the Hiritano highway 40 km from Port Moresby, Papua New Guinea	1998-FEB	PMID[16038553]
NPO6160	Vaccinium oxycoccos	Species	Ericaceae	Eukaryota	n.a.	fruit	n.a.	PMID[16417304]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	Esuela Tecnica Superior de Ingenieros Agrónomos de Albacete	2007	PMID[19256538]
NPO11917	Asterospicularia laurae	Species	Xeniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[19863101]
NPO3478	Nelumbo nucifera	Species	Nelumbonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19919095]
NPO17094	Sinularia depressa	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[20121250]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20826702]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20973550]
NPO4181	Pseudoalteromonas luteoviolacea	Species	Pseudoalteromonadaceae	Bacteria	n.a.	n.a.	n.a.	PMID[20973551]
NPO29956	Sanicula lamelligera	Species	Apiaceae	Eukaryota	Whole plants	Mountain Emei, Sichuan Province, China	2008-OCT	PMID[21561060]
NPO29956	Sanicula lamelligera	Species	Apiaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[21561060]
NPO13642	Pastinaca sativa	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21800857]
NPO23024	Epimedium koreanum	Species	Berberidaceae	Eukaryota	n.a.	root	n.a.	PMID[22051934]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22537213]
NPO3478	Nelumbo nucifera	Species	Nelumbonaceae	Eukaryota	flower buds and leaves	Khon Kaen province, Thailand	2010	PMID[23270663]
NPO17094	Sinularia depressa	Species	Alcyoniidae	Eukaryota	n.a.	Hainan soft coral	n.a.	PMID[23357636]
NPO3478	Nelumbo nucifera	Species	Nelumbonaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[23642481]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23700450]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23759170]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	leaf	n.a.	PMID[23849114]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24310066]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	Stalks	n.a.	n.a.	PMID[24521157]
NPO23024	Epimedium koreanum	Species	Berberidaceae	Eukaryota	aerial parts	herbal garden of Chungbuk National University, Cheongju, Korea	2012-Oct	PMID[24963714]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	seed	n.a.	PMID[25433632]
NPO13847	Streptomyces avermectinius	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[25611131]
NPO26327	Chaenomeles sinensis	Species	Rosaceae	Eukaryota	Twigs	n.a.	n.a.	PMID[25894905]
NPO3478	Nelumbo nucifera	Species	Nelumbonaceae	Eukaryota	Flowers	n.a.	n.a.	PMID[26462418]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	seed	n.a.	PMID[26860358]
NPO26327	Chaenomeles sinensis	Species	Rosaceae	Eukaryota	Twigs	n.a.	n.a.	PMID[28358502]
NPO2722	Humulus japonicus	Species	Cannabaceae	Eukaryota	Aerial Parts	n.a.	n.a.	PMID[29254897]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	Seeds	Benedictine Pannonhalma Archabbey, Hungary		PMID[29803478]
NPO40939	Syzygium corticosum	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[30057155]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31433178]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	n.a.		PMID[31861466]
NPO4554	Isatis tinctoria	Species	Brassicaceae	Eukaryota	Roots	n.a.	n.a.	PMID[32004936]
NPO13847	Streptomyces avermectinius	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[464561]
NPO14685	Swertia franchetiana	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7513747]
NPO14685	Swertia franchetiana	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7561895]
NPO23024	Epimedium koreanum	Species	Berberidaceae	Eukaryota	n.a.	aerial part	n.a.	Database[Article]
NPO13642	Pastinaca sativa	Species	Apiaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO3478	Nelumbo nucifera	Species	Nelumbonaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO3478	Nelumbo nucifera	Species	Nelumbonaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO16333	Chenopodium album	Species	Chenopodiaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	Shoot	n.a.	n.a.	Database[FooDB]
NPO13642	Pastinaca sativa	Species	Apiaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	Stem	n.a.	n.a.	Database[FooDB]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	Leaf Essent. Oil	n.a.	n.a.	Database[FooDB]
NPO6160	Vaccinium oxycoccos	Species	Ericaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	Petiole	n.a.	n.a.	Database[FooDB]
NPO16333	Chenopodium album	Species	Chenopodiaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO3478	Nelumbo nucifera	Species	Nelumbonaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO16333	Chenopodium album	Species	Chenopodiaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	Protoplast	n.a.	n.a.	Database[FooDB]
NPO3478	Nelumbo nucifera	Species	Nelumbonaceae	Eukaryota	Rhizome	n.a.	n.a.	Database[FooDB]
NPO13642	Pastinaca sativa	Species	Apiaceae	Eukaryota	Root	n.a.	n.a.	Database[FooDB]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO13642	Pastinaca sativa	Species	Apiaceae	Eukaryota	Roots	n.a.		Database[FooDB]
NPO13642	Pastinaca sativa	Species	Apiaceae	Eukaryota	Root Essent. Oil	n.a.	n.a.	Database[FooDB]
NPO13642	Pastinaca sativa	Species	Apiaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	Fruits	n.a.		Database[FooDB]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO16333	Chenopodium album	Species	Chenopodiaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO947	Rauvolfia vomitoria	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26327	Chaenomeles sinensis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23024	Epimedium koreanum	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13167	Scutellaria amoena	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13642	Pastinaca sativa	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2722	Humulus japonicus	Species	Cannabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8650.1	Perilla frutescens var. arguta	Varieties	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO16333	Chenopodium album	Species	Chenopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO4554	Isatis tinctoria	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14685	Swertia franchetiana	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3478	Nelumbo nucifera	Species	Nelumbonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[MetaboLights]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	seed	n.a.	Database[MetaboLights]
NPO13642	Pastinaca sativa	Species	Apiaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO6160	Vaccinium oxycoccos	Species	Ericaceae	Eukaryota	Fruits	n.a.		Database[Phenol-Explorer]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO11641	Solanum laxum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26327	Chaenomeles sinensis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13642	Pastinaca sativa	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO947	Rauvolfia vomitoria	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13167	Scutellaria amoena	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2722	Humulus japonicus	Species	Cannabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9516	Gnetum latifolium	Species	Gnetaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14685	Swertia franchetiana	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16333	Chenopodium album	Species	Chenopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8650.1	Perilla frutescens var. arguta	Varieties	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4554	Isatis tinctoria	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16857	Hypericum laricifolium	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3478	Nelumbo nucifera	Species	Nelumbonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23024	Epimedium koreanum	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2722	Humulus japonicus	Species	Cannabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO3478	Nelumbo nucifera	Species	Nelumbonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO13642	Pastinaca sativa	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO23024	Epimedium koreanum	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO13167	Scutellaria amoena	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO26327	Chaenomeles sinensis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO4554	Isatis tinctoria	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO3478	Nelumbo nucifera	Species	Nelumbonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO23024	Epimedium koreanum	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO26327	Chaenomeles sinensis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16857	Hypericum laricifolium	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9533	Pterocaulon polystachyum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18022	Naucleopsis ternstroemiiflora	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO947	Rauvolfia vomitoria	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11538	Salvia syriaca	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3964	Calostephane divaricata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8	Buphthalmum salicifolium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15227	Helipterum roseum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4325	Blastochloris viridis	Species	Hyphomicrobiaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO16611	Alstonia spathulata	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2722	Humulus japonicus	Species	Cannabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17472	Drechslera avenae	Species	Pleosporaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15803	Artemisia assoana	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17865	Amathia pinnata	Species	Vesiculariidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13642	Pastinaca sativa	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14859	Bishovia boliviensis	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO16333	Chenopodium album	Species	Chenopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8506	Cotyledon secunda	Species	Crassulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16089	Dumortiera hirsuta	Species	Dumortieraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17242	Laurencia spectabilis	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14395	Lysimachia mauritiana	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10989	Annona cornifolia	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16493	Nasutitermes ephratae	Species	Termitoidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8650.1	Perilla frutescens var. arguta	Varieties	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3478	Nelumbo nucifera	Species	Nelumbonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16731	Phoebe pittieri	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15063	Leathesia nana	Species	Chordariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4554	Isatis tinctoria	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17400	Peltostigma guatemalense	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4181	Pseudoalteromonas luteoviolacea	Species	Pseudoalteromonadaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO17786	Marrubium anisodon	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14685	Swertia franchetiana	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4578	Cystoseira fimbriata	Species	Sargassaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6881	Caragana aurantiaca	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2507	Rumex maritimus	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17544	Acacia adunca	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10417	Ipomoea digitata	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7562	Premna odorata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17702	Astragalus sempervirens	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3676	Fusarium sambucinum	Species	Nectriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23024	Epimedium koreanum	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12703	Eucalyptus melliodora	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15659	Zanthoxylum tetraspermum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17633	Viguiera incana	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17094	Sinularia depressa	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11917	Asterospicularia laurae	Species	Xeniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15467	Hedysarum connatum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16369	Lepisorus ussuriensis	Species	Polypodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21724	Sabina sargentii	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO13407	Goniothalamus malayanus	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17169	Adiantum lunulatum	Species	Pteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11641	Solanum laxum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13167	Scutellaria amoena	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25853	Sideritis argosphacelus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12897	Dolichospermum viguieri	Species	Aphanizomenonaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO13847	Streptomyces avermectinius	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO15552	Anacystis montana	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO17942	Wikstroemia retusa	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9516	Gnetum latifolium	Species	Gnetaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6160	Vaccinium oxycoccos	Species	Ericaceae	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
NPO8541	NPC136473	Other	Petiole	0.1	0.1	0.1	mg/100g	Database [DUKE]

☑ 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	1
IC50	13
Others	2

Activity Type	# Activity
Cell Line	13
Organism	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	64400.0	nM	PMID[459774]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	64400.0	nM	PMID[459774]
NPT659	Cell Line	SMMC-7721	Homo sapiens	IC50	>	64400.0	nM	PMID[459774]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	>	64400.0	nM	PMID[459774]
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	>	64400.0	nM	PMID[459774]
NPT1452	Cell Line	C8166	Homo sapiens	CC50	>	450500.0	nM	PMID[459774]
NPT660	Cell Line	SW480	Homo sapiens	IC50	>	64400.0	nM	PMID[459774]
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	38500.0	nM	PMID[459776]
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	>	50000.0	nM	PMID[459776]
NPT139	Cell Line	HT-29	Homo sapiens	IC50	>	10000.0	nM	PMID[459778]
NPT400	Cell Line	MDA-MB-435	Homo sapiens	IC50	>	10000.0	nM	PMID[459778]
NPT377	Cell Line	OVCAR-3	Homo sapiens	IC50	>	10000.0	nM	PMID[459778]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	>	10.0	ug.mL-1	PMID[459772]
NPT364	Organism	Lactuca sativa	Lactuca sativa	Activity	=	30.0	%	PMID[459773]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	EC50	>	450500.0	nM	PMID[459774]

☑ 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 NPC136473 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	147
0.1-0.2	1498
0.2-0.3	9255
0.3-0.4	17378
0.4-0.5	8336
0.5-0.6	4743
0.6-0.7	1170
0.7-0.8	147
0.8-0.85	11
0.85-0.9	6
0.9-0.95	4
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9552	High Similarity	NPC153660
0.9265	High Similarity	NPC323437
0.9265	High Similarity	NPC29542
0.9265	High Similarity	NPC201562
0.9	High Similarity	NPC169056
0.9	High Similarity	NPC166018
0.9	High Similarity	NPC225665
0.8529	High Similarity	NPC269985
0.8451	Intermediate Similarity	NPC186042
0.84	Intermediate Similarity	NPC160582
0.8267	Intermediate Similarity	NPC19900
0.8261	Intermediate Similarity	NPC106613
0.8154	Intermediate Similarity	NPC311852
0.8143	Intermediate Similarity	NPC117804
0.8108	Intermediate Similarity	NPC151622
0.8108	Intermediate Similarity	NPC7629
0.8082	Intermediate Similarity	NPC215050
0.8	Intermediate Similarity	NPC34110
0.7949	Intermediate Similarity	NPC38796
0.7949	Intermediate Similarity	NPC158411
0.7945	Intermediate Similarity	NPC247586
0.7895	Intermediate Similarity	NPC275494
0.7895	Intermediate Similarity	NPC471409
0.7895	Intermediate Similarity	NPC475994
0.7821	Intermediate Similarity	NPC226068
0.7808	Intermediate Similarity	NPC95863
0.7763	Intermediate Similarity	NPC257666
0.7763	Intermediate Similarity	NPC82666
0.7763	Intermediate Similarity	NPC266193
0.7763	Intermediate Similarity	NPC97377
0.7733	Intermediate Similarity	NPC476346
0.7681	Intermediate Similarity	NPC288253
0.7662	Intermediate Similarity	NPC62336
0.7632	Intermediate Similarity	NPC472305
0.7632	Intermediate Similarity	NPC186554
0.7632	Intermediate Similarity	NPC263582
0.7632	Intermediate Similarity	NPC76966
0.76	Intermediate Similarity	NPC122244
0.759	Intermediate Similarity	NPC48107
0.7568	Intermediate Similarity	NPC21944
0.7568	Intermediate Similarity	NPC84790
0.7564	Intermediate Similarity	NPC170394
0.7564	Intermediate Similarity	NPC308038
0.7561	Intermediate Similarity	NPC472974
0.7536	Intermediate Similarity	NPC269737
0.7532	Intermediate Similarity	NPC97173
0.7531	Intermediate Similarity	NPC476412
0.75	Intermediate Similarity	NPC279186
0.75	Intermediate Similarity	NPC92226
0.747	Intermediate Similarity	NPC471792
0.7468	Intermediate Similarity	NPC45495
0.7468	Intermediate Similarity	NPC172013
0.7468	Intermediate Similarity	NPC476809
0.7468	Intermediate Similarity	NPC469637
0.7468	Intermediate Similarity	NPC472301
0.7467	Intermediate Similarity	NPC130016
0.7467	Intermediate Similarity	NPC109576
0.7467	Intermediate Similarity	NPC180015
0.7467	Intermediate Similarity	NPC56747
0.7439	Intermediate Similarity	NPC70685
0.7439	Intermediate Similarity	NPC476426
0.7429	Intermediate Similarity	NPC190049
0.7407	Intermediate Similarity	NPC49019
0.7403	Intermediate Similarity	NPC470525
0.7385	Intermediate Similarity	NPC23117
0.7385	Intermediate Similarity	NPC14002
0.7381	Intermediate Similarity	NPC471793
0.7381	Intermediate Similarity	NPC58271
0.7381	Intermediate Similarity	NPC471791
0.7356	Intermediate Similarity	NPC78159
0.7349	Intermediate Similarity	NPC194417
0.7344	Intermediate Similarity	NPC64866
0.7342	Intermediate Similarity	NPC7232
0.7333	Intermediate Similarity	NPC133253
0.7324	Intermediate Similarity	NPC212210
0.7324	Intermediate Similarity	NPC150162
0.7308	Intermediate Similarity	NPC74995
0.7308	Intermediate Similarity	NPC203403
0.7294	Intermediate Similarity	NPC474918
0.7294	Intermediate Similarity	NPC472973
0.7286	Intermediate Similarity	NPC64985
0.7284	Intermediate Similarity	NPC93590
0.7273	Intermediate Similarity	NPC114236
0.7273	Intermediate Similarity	NPC476795
0.7273	Intermediate Similarity	NPC5626
0.7273	Intermediate Similarity	NPC476245
0.7262	Intermediate Similarity	NPC476409
0.726	Intermediate Similarity	NPC263161
0.725	Intermediate Similarity	NPC471514
0.725	Intermediate Similarity	NPC148685
0.725	Intermediate Similarity	NPC138492
0.725	Intermediate Similarity	NPC824
0.725	Intermediate Similarity	NPC233352
0.725	Intermediate Similarity	NPC157895
0.725	Intermediate Similarity	NPC104120
0.7237	Intermediate Similarity	NPC276336
0.7222	Intermediate Similarity	NPC251118
0.7215	Intermediate Similarity	NPC179028
0.7215	Intermediate Similarity	NPC19443
0.7215	Intermediate Similarity	NPC74410
0.7215	Intermediate Similarity	NPC231739
0.7215	Intermediate Similarity	NPC198240
0.7215	Intermediate Similarity	NPC207772
0.7215	Intermediate Similarity	NPC169095
0.7215	Intermediate Similarity	NPC189485
0.7209	Intermediate Similarity	NPC134321
0.72	Intermediate Similarity	NPC203819
0.7195	Intermediate Similarity	NPC169941
0.7195	Intermediate Similarity	NPC251475
0.7179	Intermediate Similarity	NPC1254
0.7179	Intermediate Similarity	NPC180886
0.7176	Intermediate Similarity	NPC72397
0.7162	Intermediate Similarity	NPC188292
0.7162	Intermediate Similarity	NPC260474
0.7162	Intermediate Similarity	NPC87141
0.716	Intermediate Similarity	NPC6663
0.716	Intermediate Similarity	NPC473217
0.716	Intermediate Similarity	NPC470298
0.7143	Intermediate Similarity	NPC472986
0.7143	Intermediate Similarity	NPC472985
0.7143	Intermediate Similarity	NPC127582
0.7143	Intermediate Similarity	NPC213223
0.7126	Intermediate Similarity	NPC472978
0.7126	Intermediate Similarity	NPC116726
0.7126	Intermediate Similarity	NPC475441
0.7126	Intermediate Similarity	NPC252433
0.7125	Intermediate Similarity	NPC281138
0.7125	Intermediate Similarity	NPC27817
0.7125	Intermediate Similarity	NPC152061
0.7123	Intermediate Similarity	NPC100719
0.7123	Intermediate Similarity	NPC166791
0.7123	Intermediate Similarity	NPC197089
0.7123	Intermediate Similarity	NPC322035
0.7121	Intermediate Similarity	NPC37644
0.7108	Intermediate Similarity	NPC251170
0.7108	Intermediate Similarity	NPC7927
0.7108	Intermediate Similarity	NPC40687
0.7108	Intermediate Similarity	NPC230527
0.7105	Intermediate Similarity	NPC144627
0.7101	Intermediate Similarity	NPC308108
0.7101	Intermediate Similarity	NPC170799
0.7093	Intermediate Similarity	NPC472688
0.7093	Intermediate Similarity	NPC36668
0.7093	Intermediate Similarity	NPC472676
0.7093	Intermediate Similarity	NPC262043
0.7093	Intermediate Similarity	NPC118011
0.7093	Intermediate Similarity	NPC472983
0.7089	Intermediate Similarity	NPC471061
0.7089	Intermediate Similarity	NPC85105
0.7089	Intermediate Similarity	NPC197659
0.7089	Intermediate Similarity	NPC61952
0.7089	Intermediate Similarity	NPC149550
0.7089	Intermediate Similarity	NPC165711
0.7073	Intermediate Similarity	NPC238991
0.7073	Intermediate Similarity	NPC302661
0.7073	Intermediate Similarity	NPC227925
0.7073	Intermediate Similarity	NPC472867
0.7073	Intermediate Similarity	NPC3511
0.7073	Intermediate Similarity	NPC472239
0.7073	Intermediate Similarity	NPC142253
0.7073	Intermediate Similarity	NPC469806
0.7073	Intermediate Similarity	NPC469799
0.7067	Intermediate Similarity	NPC469914
0.7067	Intermediate Similarity	NPC256846
0.7051	Intermediate Similarity	NPC472327
0.7051	Intermediate Similarity	NPC251435
0.7045	Intermediate Similarity	NPC131840
0.7045	Intermediate Similarity	NPC476416
0.7042	Intermediate Similarity	NPC213152
0.7037	Intermediate Similarity	NPC108955
0.7037	Intermediate Similarity	NPC271104
0.7027	Intermediate Similarity	NPC254886
0.7027	Intermediate Similarity	NPC475523
0.7024	Intermediate Similarity	NPC255174
0.7024	Intermediate Similarity	NPC179006
0.7024	Intermediate Similarity	NPC474853
0.7015	Intermediate Similarity	NPC474127
0.7013	Intermediate Similarity	NPC35656
0.7011	Intermediate Similarity	NPC230332
0.7011	Intermediate Similarity	NPC128672
0.7	Intermediate Similarity	NPC80088
0.7	Intermediate Similarity	NPC253561
0.7	Intermediate Similarity	NPC248624
0.7	Intermediate Similarity	NPC297996
0.7	Intermediate Similarity	NPC478122
0.6988	Remote Similarity	NPC279639
0.6988	Remote Similarity	NPC64600
0.6988	Remote Similarity	NPC97913
0.6988	Remote Similarity	NPC3856
0.6988	Remote Similarity	NPC105173
0.6988	Remote Similarity	NPC297398
0.6974	Remote Similarity	NPC107848
0.6966	Remote Similarity	NPC472977
0.6966	Remote Similarity	NPC472976
0.6966	Remote Similarity	NPC299100
0.6966	Remote Similarity	NPC196227
0.6962	Remote Similarity	NPC26504
0.6962	Remote Similarity	NPC110725
0.6962	Remote Similarity	NPC250621
0.6962	Remote Similarity	NPC19907

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 NPC136473 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	144
0.1-0.2	2106
0.2-0.3	4328
0.3-0.4	1898
0.4-0.5	433
0.5-0.6	208
0.6-0.7	31
0.7-0.8	2
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7349	Intermediate Similarity	NPD4623	Approved
0.7349	Intermediate Similarity	NPD4519	Discontinued
0.7123	Intermediate Similarity	NPD7331	Phase 2
0.7101	Intermediate Similarity	NPD287	Approved
0.7037	Intermediate Similarity	NPD4695	Discontinued
0.7024	Intermediate Similarity	NPD1696	Phase 3
0.6941	Remote Similarity	NPD5690	Phase 2
0.6941	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD4221	Approved
0.6867	Remote Similarity	NPD4223	Phase 3
0.6806	Remote Similarity	NPD4191	Approved
0.6806	Remote Similarity	NPD4194	Approved
0.6806	Remote Similarity	NPD4192	Approved
0.6806	Remote Similarity	NPD4193	Approved
0.6753	Remote Similarity	NPD4691	Approved
0.6744	Remote Similarity	NPD3618	Phase 1
0.6709	Remote Similarity	NPD4058	Approved
0.6707	Remote Similarity	NPD4195	Approved
0.6706	Remote Similarity	NPD4197	Approved
0.6628	Remote Similarity	NPD5329	Approved
0.6627	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6623	Remote Similarity	NPD4137	Phase 3
0.6575	Remote Similarity	NPD368	Approved
0.6556	Remote Similarity	NPD5284	Approved
0.6556	Remote Similarity	NPD5281	Approved
0.6556	Remote Similarity	NPD6079	Approved
0.6552	Remote Similarity	NPD4138	Approved
0.6552	Remote Similarity	NPD4693	Phase 3
0.6552	Remote Similarity	NPD4690	Approved
0.6552	Remote Similarity	NPD5280	Approved
0.6552	Remote Similarity	NPD4689	Approved
0.6552	Remote Similarity	NPD5205	Approved
0.6552	Remote Similarity	NPD4688	Approved
0.6552	Remote Similarity	NPD4694	Approved
0.6538	Remote Similarity	NPD4747	Approved
0.6533	Remote Similarity	NPD7341	Phase 2
0.6522	Remote Similarity	NPD4629	Approved
0.6522	Remote Similarity	NPD5210	Approved
0.6512	Remote Similarity	NPD3666	Approved
0.6512	Remote Similarity	NPD3665	Phase 1
0.6512	Remote Similarity	NPD3133	Approved
0.65	Remote Similarity	NPD4687	Approved
0.6486	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.6477	Remote Similarity	NPD3573	Approved
0.6458	Remote Similarity	NPD5211	Phase 2
0.6456	Remote Similarity	NPD5276	Approved
0.6437	Remote Similarity	NPD1694	Approved
0.6404	Remote Similarity	NPD4518	Approved
0.6386	Remote Similarity	NPD3617	Approved
0.6386	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD5279	Phase 3
0.6333	Remote Similarity	NPD5328	Approved
0.6333	Remote Similarity	NPD4753	Phase 2
0.6327	Remote Similarity	NPD5141	Approved
0.6304	Remote Similarity	NPD4202	Approved
0.6296	Remote Similarity	NPD5733	Approved
0.6279	Remote Similarity	NPD3667	Approved
0.6277	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6277	Remote Similarity	NPD5221	Approved
0.6277	Remote Similarity	NPD5222	Approved
0.6265	Remote Similarity	NPD4756	Discovery
0.6264	Remote Similarity	NPD5785	Approved
0.6264	Remote Similarity	NPD4096	Approved
0.625	Remote Similarity	NPD5285	Approved
0.625	Remote Similarity	NPD5286	Approved
0.625	Remote Similarity	NPD4696	Approved
0.625	Remote Similarity	NPD5363	Approved
0.622	Remote Similarity	NPD8264	Approved
0.6211	Remote Similarity	NPD5173	Approved
0.6207	Remote Similarity	NPD6110	Phase 1
0.6196	Remote Similarity	NPD7515	Phase 2
0.6186	Remote Similarity	NPD5223	Approved
0.6136	Remote Similarity	NPD4786	Approved
0.6122	Remote Similarity	NPD5091	Approved
0.6122	Remote Similarity	NPD5224	Approved
0.6122	Remote Similarity	NPD4633	Approved
0.6122	Remote Similarity	NPD5226	Approved
0.6122	Remote Similarity	NPD5225	Approved
0.6111	Remote Similarity	NPD4219	Approved
0.6105	Remote Similarity	NPD4697	Phase 3
0.6092	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6087	Remote Similarity	NPD5207	Approved
0.6076	Remote Similarity	NPD3621	Clinical (unspecified phase)
0.6064	Remote Similarity	NPD7748	Approved
0.6061	Remote Similarity	NPD5174	Approved
0.6061	Remote Similarity	NPD5175	Approved
0.6047	Remote Similarity	NPD4252	Approved
0.6042	Remote Similarity	NPD4755	Approved
0.6042	Remote Similarity	NPD7902	Approved
0.6026	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.6024	Remote Similarity	NPD8039	Approved
0.6023	Remote Similarity	NPD3527	Clinical (unspecified phase)
0.6	Remote Similarity	NPD5695	Phase 3
0.5981	Remote Similarity	NPD7115	Discovery
0.5979	Remote Similarity	NPD4225	Approved
0.5979	Remote Similarity	NPD5696	Approved
0.5978	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.5977	Remote Similarity	NPD4692	Approved
0.5977	Remote Similarity	NPD4139	Approved
0.5972	Remote Similarity	NPD342	Phase 1
0.5957	Remote Similarity	NPD5133	Approved
0.5918	Remote Similarity	NPD6404	Discontinued
0.5918	Remote Similarity	NPD4700	Approved
0.5909	Remote Similarity	NPD5209	Approved
0.5909	Remote Similarity	NPD4269	Approved
0.5909	Remote Similarity	NPD4270	Approved
0.5895	Remote Similarity	NPD6001	Approved
0.5895	Remote Similarity	NPD5282	Discontinued
0.5882	Remote Similarity	NPD5697	Approved
0.5876	Remote Similarity	NPD6083	Phase 2
0.5876	Remote Similarity	NPD6084	Phase 2
0.587	Remote Similarity	NPD5208	Approved
0.5851	Remote Similarity	NPD5694	Approved
0.5851	Remote Similarity	NPD5693	Phase 1
0.5843	Remote Similarity	NPD4788	Approved
0.5833	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.5833	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.5825	Remote Similarity	NPD6011	Approved
0.5825	Remote Similarity	NPD4730	Approved
0.5825	Remote Similarity	NPD4729	Approved
0.5825	Remote Similarity	NPD6899	Approved
0.5825	Remote Similarity	NPD6881	Approved
0.5824	Remote Similarity	NPD6684	Approved
0.5824	Remote Similarity	NPD7521	Approved
0.5824	Remote Similarity	NPD6409	Approved
0.5824	Remote Similarity	NPD7146	Approved
0.5824	Remote Similarity	NPD5330	Approved
0.5824	Remote Similarity	NPD7334	Approved
0.5814	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.581	Remote Similarity	NPD6649	Approved
0.581	Remote Similarity	NPD6650	Approved
0.5806	Remote Similarity	NPD6673	Approved
0.5806	Remote Similarity	NPD6904	Approved
0.5806	Remote Similarity	NPD6080	Approved
0.5797	Remote Similarity	NPD3173	Approved
0.5795	Remote Similarity	NPD8028	Phase 2
0.5789	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.5789	Remote Similarity	NPD6399	Phase 3
0.5783	Remote Similarity	NPD4732	Discontinued
0.5778	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.5778	Remote Similarity	NPD3668	Phase 3
0.5773	Remote Similarity	NPD7614	Phase 1
0.5769	Remote Similarity	NPD6012	Approved
0.5769	Remote Similarity	NPD6014	Approved
0.5769	Remote Similarity	NPD6013	Approved
0.5758	Remote Similarity	NPD7640	Approved
0.5758	Remote Similarity	NPD7639	Approved
0.5753	Remote Similarity	NPD4627	Clinical (unspecified phase)
0.5745	Remote Similarity	NPD5692	Phase 3
0.5743	Remote Similarity	NPD4754	Approved
0.573	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.5729	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.5729	Remote Similarity	NPD7900	Approved
0.5714	Remote Similarity	NPD5250	Approved
0.5714	Remote Similarity	NPD4785	Approved
0.5714	Remote Similarity	NPD5247	Approved
0.5714	Remote Similarity	NPD4634	Approved
0.5714	Remote Similarity	NPD5249	Phase 3
0.5714	Remote Similarity	NPD7290	Approved
0.5714	Remote Similarity	NPD5251	Approved
0.5714	Remote Similarity	NPD5248	Approved
0.5714	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD5135	Approved
0.5714	Remote Similarity	NPD6883	Approved
0.5714	Remote Similarity	NPD7102	Approved
0.5714	Remote Similarity	NPD4784	Approved
0.5714	Remote Similarity	NPD5169	Approved
0.5699	Remote Similarity	NPD6903	Approved
0.5699	Remote Similarity	NPD6672	Approved
0.5699	Remote Similarity	NPD5737	Approved
0.5699	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.5694	Remote Similarity	NPD3172	Approved
0.5684	Remote Similarity	NPD6050	Approved
0.5682	Remote Similarity	NPD4820	Approved
0.5682	Remote Similarity	NPD4821	Approved
0.5682	Remote Similarity	NPD7332	Phase 2
0.5682	Remote Similarity	NPD4819	Approved
0.5682	Remote Similarity	NPD4822	Approved
0.5682	Remote Similarity	NPD7514	Phase 3
0.5673	Remote Similarity	NPD5168	Approved
0.5673	Remote Similarity	NPD5128	Approved
0.5667	Remote Similarity	NPD5362	Discontinued
0.5663	Remote Similarity	NPD4243	Approved
0.566	Remote Similarity	NPD5216	Approved
0.566	Remote Similarity	NPD5217	Approved
0.566	Remote Similarity	NPD5215	Approved
0.566	Remote Similarity	NPD8130	Phase 1
0.566	Remote Similarity	NPD6869	Approved
0.566	Remote Similarity	NPD6617	Approved
0.566	Remote Similarity	NPD6847	Approved
0.566	Remote Similarity	NPD5127	Approved
0.5657	Remote Similarity	NPD7638	Approved
0.5652	Remote Similarity	NPD5786	Approved
0.5652	Remote Similarity	NPD6098	Approved
0.5632	Remote Similarity	NPD4268	Approved
0.5632	Remote Similarity	NPD4271	Approved
0.5631	Remote Similarity	NPD4767	Approved
0.5631	Remote Similarity	NPD6675	Approved
0.5631	Remote Similarity	NPD5739	Approved
0.5631	Remote Similarity	NPD4768	Approved

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