NPASS Compound

Structure

CID236769 OpenBabel06191716032D 26 28 0 0 0 0 0 0 0 0999 V2000 3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -1.0000 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 -2.5981 1.5000 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 -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 -0.0000 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 1.7321 2.0000 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 -3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -0.0000 0.0000 O 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 -4.3301 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 22 1 0 0 0 0 2 23 1 0 0 0 0 3 24 1 0 0 0 0 4 25 1 0 0 0 0 5 6 2 0 0 0 0 5 10 1 0 0 0 0 6 13 1 0 0 0 0 7 10 2 0 0 0 0 7 14 1 0 0 0 0 8 11 2 0 0 0 0 8 12 1 0 0 0 0 9 11 1 0 0 0 0 9 15 2 0 0 0 0 10 18 1 0 0 0 0 11 22 1 0 0 0 0 12 16 2 0 0 0 0 12 20 1 0 0 0 0 13 14 2 0 0 0 0 13 23 1 0 0 0 0 14 24 1 0 0 0 0 15 16 1 0 0 0 0 15 26 1 0 0 0 0 16 17 1 0 0 0 0 17 19 1 0 0 0 0 17 21 2 0 0 0 0 18 19 2 0 0 0 0 18 26 1 0 0 0 0 19 25 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	358.11
Volume:	351.951
LogP:	3.305
LogD:	2.906
LogS:	-4.397
# Rotatable Bonds:	5
TPSA:	87.36
# H-Bond Aceptor:	7
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.749
Synthetic Accessibility Score:	2.246
Fsp3:	0.211
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:	-4.704
MDCK Permeability:	3.5863384255208075e-05
Pgp-inhibitor:	0.998
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.009

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.019
Plasma Protein Binding (PPB):	81.54876708984375%
Volume Distribution (VD):	0.86
Pgp-substrate:	17.187210083007812%

ADMET: Metabolism

CYP1A2-inhibitor:	0.873
CYP1A2-substrate:	0.974
CYP2C19-inhibitor:	0.744
CYP2C19-substrate:	0.601
CYP2C9-inhibitor:	0.699
CYP2C9-substrate:	0.925
CYP2D6-inhibitor:	0.381
CYP2D6-substrate:	0.926
CYP3A4-inhibitor:	0.756
CYP3A4-substrate:	0.427

ADMET: Excretion

Clearance (CL):	6.298
Half-life (T1/2):	0.662

ADMET: Toxicity

hERG Blockers:	0.034
Human Hepatotoxicity (H-HT):	0.161
Drug-inuced Liver Injury (DILI):	0.963
AMES Toxicity:	0.47
Rat Oral Acute Toxicity:	0.146
Maximum Recommended Daily Dose:	0.132
Skin Sensitization:	0.141
Carcinogencity:	0.034
Eye Corrosion:	0.004
Eye Irritation:	0.218
Respiratory Toxicity:	0.26

Download Data

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

Natural Product: NPC236769

Natural Product ID:	NPC236769
*Common Name:**	Retusin
IUPAC Name:	2-(3,4-dimethoxyphenyl)-5-hydroxy-3,7-dimethoxychromen-4-one
Synonyms:	NSC-61837
Standard InCHIKey:	HHGPYJLEJGNWJA-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C19H18O7/c1-22-11-8-12(20)16-15(9-11)26-18(19(25-4)17(16)21)10-5-6-13(23-2)14(7-10)24-3/h5-9,20H,1-4H3
SMILES:	COc1cc(c2c(c1)oc(c1ccc(c(c1)OC)OC)c(c2=O)OC)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL77966
PubChem CID:	5352005
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0002585] O-methylated flavonoids [CHEMONTID:0002592] 7-O-methylated 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
NPO1373	Pulsatilla chinensis	Species	Ranunculaceae	Eukaryota	roots	n.a.	n.a.	PMID[10514313]
NPO1373	Pulsatilla chinensis	Species	Ranunculaceae	Eukaryota	n.a.	root	n.a.	PMID[10514313]
NPO27986	Lonchocarpus chiricanus	Species	Fabaceae	Eukaryota	Root barks	n.a.	n.a.	PMID[11421729]
NPO20244	Melicope semecarpifolia	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11575945]
NPO1373	Pulsatilla chinensis	Species	Ranunculaceae	Eukaryota	roots	n.a.	n.a.	PMID[11575962]
NPO29463	Pogostemon cablin	Species	Lamiaceae	Eukaryota	n.a.	stem	n.a.	PMID[12575075]
NPO29463	Pogostemon cablin	Species	Lamiaceae	Eukaryota	n.a.	leaf	n.a.	PMID[12575075]
NPO29463	Pogostemon cablin	Species	Lamiaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[15577255]
NPO27695	Centaurea sonchifolia	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[1624943]
NPO27600	Boesenbergia pandurata	Species	Zingiberaceae	Eukaryota	rhizomes	Pindaya Township, Shan State, Myanmar	2004-NOV	PMID[17896818]
NPO20244	Melicope semecarpifolia	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18163582]
NPO13135	Campylotropis hirtella	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19481938]
NPO17376	Bacillus amyloliquefaciens	Species	Bacillaceae	Bacteria	n.a.	n.a.	n.a.	PMID[23265519]
NPO17376	Bacillus amyloliquefaciens	Species	Bacillaceae	Bacteria	n.a.	n.a.	n.a.	PMID[24698790]
NPO27600	Boesenbergia pandurata	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27508308]
NPO17376	Bacillus amyloliquefaciens	Species	Bacillaceae	Bacteria	n.a.	n.a.	n.a.	PMID[27934031]
NPO27600	Boesenbergia pandurata	Species	Zingiberaceae	Eukaryota	Rhizomes	n.a.	n.a.	PMID[28099006]
NPO12796	Periploca sepium	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28294615]
NPO29463	Pogostemon cablin	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[30188125]
NPO865	Dendrobium loddigesii	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31291099]
NPO19745	Esox lucius	Species	Esocidae	Eukaryota	n.a.	n.a.	n.a.	PMID[3349210]
NPO28159	Rubia akane	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8176404]
NPO19745	Esox lucius	Species	Esocidae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO19745	Esox lucius	Species	Esocidae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO12796	Periploca sepium	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO20244	Melicope semecarpifolia	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21600	Aconitum variegatum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18591	Senecio vulgaris	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1373	Pulsatilla chinensis	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3642	Crotalaria spartioides	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7773	Crinum moorei	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21175	Senecio retrorsus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13135	Campylotropis hirtella	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3392	Agastache rugosus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22500	Stephania dielsiana	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2379	Senecio oryzetorum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29463	Pogostemon cablin	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO865	Dendrobium loddigesii	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO6731	Ononis spinosa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1373	Pulsatilla chinensis	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13135	Campylotropis hirtella	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO865	Dendrobium loddigesii	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20244	Melicope semecarpifolia	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22683	Pteris bella	Species	Pteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23156	Maclura cochinchinensis	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22500	Stephania dielsiana	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27882	Boswellia ovalifoliolata	Species	Burseraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6731	Ononis spinosa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12796	Periploca sepium	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27397	Drymaria cordata	Species	Caryophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24496	Gymnopetalum integrifolium	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3642	Crotalaria spartioides	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3392	Agastache rugosus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2379	Senecio oryzetorum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18591	Senecio vulgaris	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29463	Pogostemon cablin	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21600	Aconitum variegatum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21175	Senecio retrorsus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7773	Crinum moorei	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO865	Dendrobium loddigesii	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO1373	Pulsatilla chinensis	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO6731	Ononis spinosa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO18591	Senecio vulgaris	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO29463	Pogostemon cablin	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO12796	Periploca sepium	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO21600	Aconitum variegatum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO2379	Senecio oryzetorum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO12796	Periploca sepium	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO29463	Pogostemon cablin	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO28159	Rubia akane	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO1373	Pulsatilla chinensis	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO865	Dendrobium loddigesii	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO27882	Boswellia ovalifoliolata	Species	Burseraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27397	Drymaria cordata	Species	Caryophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12565	Hypericum polyanthemum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18591	Senecio vulgaris	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7822.1	Eucalyptus globulus subsp. bicostata	Subspecies	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27145	Euphorbia hylonoma	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27234	Thalassiosira weissflogii	Species	Thalassiosiraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26553	Lemonia spectabilis	Species	Lemoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21175	Senecio retrorsus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27702	Matricaria sabulosa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1373	Pulsatilla chinensis	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28206	Aniba santalodora	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23426	Andromeda polifolia	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19383	Lactarius mitissimus	Species	Russulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3711	Acalypha australis	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13135	Campylotropis hirtella	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3642	Crotalaria spartioides	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11190	Veronica polita	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24014	Scapania bolanderi	Species	Scapaniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19778	Streptomyces flaveus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO11576	Glycosmis macrophylla	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28426	Etmopterus spinax	Species	Etmopteridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26321	Salvia patens	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24576	Genista lydia	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9354	Lepechinia urbanii	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27854	Sphaeria rousseliana	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO27614	Salix rosmarinifolia	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28083	Salvia lavanduloides	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13008	Methanobrevibacter arboriphilus	Species	Methanobacteriaceae	Archaea	n.a.	n.a.	n.a.	Database[UNPD]
NPO26342	Dialium excelsum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28412	Amorphophallus konjac	Species	Araceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6289	Ceropegia dichotoma	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23156	Maclura cochinchinensis	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27695	Centaurea sonchifolia	Species	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO10922	Pentaclethra macrophylla	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20584	Cheilanthes fragrans	Species	Pteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28289	Nepytia freemani	Species	Geometridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1815	Breonia chinensis	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2030	Mimosa pigra	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5456	Juniperus drupacea	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12091	Martensia denticulata	Species	Delesseriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27600	Boesenbergia pandurata	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9704	Sonneratia caseolaris	Species	Lythraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25499	Campanula choziatowskyi	Species	Campanulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28044	Erythrina hypaphorus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7773	Crinum moorei	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23300	Trichilia heudelotii	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27986	Lonchocarpus chiricanus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23384	Rhodiola semenovii	Species	Crassulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16156	Mucuna holtonii	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27338	Senecio platyphylloides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24184	Argyrochosma pilifera	Species	Pteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5043	Eria japonica	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28063	Beilschmiedia madang	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16298	Quercus marilandica	Species	Fagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5970.1	Petunia axillaris subsp. parodii	Subspecies	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22500	Stephania dielsiana	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4164	Salvia virgata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21534	Ostrya carpinifolia	Species	Betulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27613	Helleborus macranthus	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO865	Dendrobium loddigesii	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11849	Cynoglossum macrostylum	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1257	Distephanus angulifolius	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29463	Pogostemon cablin	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO526	Salvia sessei	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28159	Rubia akane	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10605	Tristania conferta	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25835	Parmotrema nilgherrense	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27816	Pterocaulon serrulatum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6731	Ononis spinosa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21600	Aconitum variegatum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8934	Gypsophila perfoliata	Species	Caryophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10638	Plectranthus myrianthus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24139	Calamus strictus	Species	Sparidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12796	Periploca sepium	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2379	Senecio oryzetorum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1184	Colchicum filifolium	Species	Colchicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22691	Mentha cardiaca	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3873	Crotalaria candicans	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22683	Pteris bella	Species	Pteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17337	Centaurea scoparia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27642	Podocarpus dacrydioides	Species	Podocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28385	Iris kashmiriana	Species	Tarachodidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9532	Vernonia cistifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27637	Heliotropium scabrum	Species	Heliotropiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17376	Bacillus amyloliquefaciens	Species	Bacillaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO27506	Orgyia pseudotsugata	Species	Lymantriidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9319	Pterocaulon virgatum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12205	Eucalyptus apodophylla	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25120	Vincetoxicum forrestii	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27916	Hardenbergia violacea	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19745	Esox lucius	Species	Esocidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28313	Mentzelia decapetala	Species	Loasaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20244	Melicope semecarpifolia	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28003	Astragalus circassicus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27455	Dysidea fragilis	Species	Dysideidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26476	Preussia terricola	Species	Sporormiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8961	Bethencourtia palmensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11843	Stephania zippeliana	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16803	Libanothamnus occultus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21720	Talaromyces variabilis	Species	Trichocomaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27057	Matsucoccus josephi	Species	Margarodidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24496	Gymnopetalum integrifolium	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21344	Fadogia agrestis	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

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

NP Quantity Composition/Concentration

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

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

Biological Activity

Activity Type	# Activity
ED50	2
GI50	49
IC50	41
Others	27

Activity Type	# Activity
Cell Line	78
CELL-LINE	1
Individual Protein	14
NON-MOLECULAR	15
Organism	3
Others	8

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT517	Cell Line	Panel NCI-60 (60 carcinoma cell lines)	Homo sapiens	GI50	=	65000.0	nM	PMID[527456]
NPT91	Cell Line	KB	Homo sapiens	ED50	>	25.0	ug ml-1	PMID[527459]
NPT91	Cell Line	KB	Homo sapiens	ED50	=	41.0	ug ml-1	PMID[527460]
NPT1422	Individual Protein	ATP-binding cassette sub-family G member 2	Homo sapiens	IC50	=	390.0	nM	PMID[527462]
NPT1422	Individual Protein	ATP-binding cassette sub-family G member 2	Homo sapiens	IC50	=	900.0	nM	PMID[527462]
NPT1594	Individual Protein	Multidrug resistance-associated protein 1	Homo sapiens	IC50	=	50000.0	nM	PMID[527462]
NPT520	Cell Line	3T3-L1	Mus musculus	Activity	=	21.0	%	PMID[527463]
NPT520	Cell Line	3T3-L1	Mus musculus	Activity	=	11.2	%	PMID[527463]
NPT520	Cell Line	3T3-L1	Mus musculus	Activity	=	3.8	%	PMID[527463]
NPT367	Cell Line	MDA-N	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[527464]
NPT369	Cell Line	ACHN	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[527464]
NPT371	Cell Line	UO-31	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[527464]
NPT116	Cell Line	HL-60	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[527464]
NPT90	Cell Line	DU-145	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[527464]
NPT373	Cell Line	SK-MEL-5	Homo sapiens	GI50	n.a.	82035.15	nM	PMID[527464]
NPT375	Cell Line	Malme-3M	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[527464]
NPT111	Cell Line	K562	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[527464]
NPT376	Cell Line	A498	Homo sapiens	GI50	n.a.	16106.46	nM	PMID[527464]
NPT377	Cell Line	OVCAR-3	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[527464]
NPT112	Cell Line	MOLT-4	Homo sapiens	GI50	n.a.	10000.0	nM	PMID[527464]
NPT379	Cell Line	HOP-62	Homo sapiens	GI50	n.a.	58479.01	nM	PMID[527464]
NPT378	Cell Line	NCI/ADR-RES	Homo sapiens	GI50	n.a.	62661.39	nM	PMID[527464]
NPT380	Cell Line	U-251	Homo sapiens	GI50	n.a.	15135.61	nM	PMID[527464]
NPT381	Cell Line	OVCAR-8	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[527464]
NPT382	Cell Line	OVCAR-5	Homo sapiens	GI50	n.a.	22961.49	nM	PMID[527464]
NPT383	Cell Line	SNB-19	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[527464]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[527464]
NPT385	Cell Line	SR	Homo sapiens	GI50	n.a.	10000.0	nM	PMID[527464]
NPT384	Cell Line	TK-10	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[527464]
NPT323	Cell Line	SW-620	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[527464]
NPT455	Cell Line	NCI-H522	Homo sapiens	GI50	n.a.	2786.12	nM	PMID[527464]
NPT387	Cell Line	M14	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[527464]
NPT388	Cell Line	NCI-H322M	Homo sapiens	GI50	n.a.	41020.41	nM	PMID[527464]
NPT389	Cell Line	RPMI-8226	Homo sapiens	GI50	n.a.	87700.08	nM	PMID[527464]
NPT456	Cell Line	OVCAR-4	Homo sapiens	GI50	n.a.	61801.64	nM	PMID[527464]
NPT390	Cell Line	LOX IMVI	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[527464]
NPT391	Cell Line	HCC 2998	Homo sapiens	GI50	n.a.	94406.09	nM	PMID[527464]
NPT81	Cell Line	A549	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[527464]
NPT148	Cell Line	HCT-15	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[527464]
NPT393	Cell Line	HCT-116	Homo sapiens	GI50	n.a.	68706.84	nM	PMID[527464]
NPT395	Cell Line	SF-268	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[527464]
NPT394	Cell Line	EKVX	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[527464]
NPT83	Cell Line	MCF7	Homo sapiens	GI50	n.a.	45708.82	nM	PMID[527464]
NPT306	Cell Line	PC-3	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[527464]
NPT146	Cell Line	SK-OV-3	Homo sapiens	GI50	n.a.	5023.43	nM	PMID[527464]
NPT397	Cell Line	NCI-H460	Homo sapiens	GI50	n.a.	19952.62	nM	PMID[527464]
NPT396	Cell Line	T47D	Homo sapiens	GI50	n.a.	31045.6	nM	PMID[527464]
NPT308	Cell Line	CAKI-1	Homo sapiens	GI50	n.a.	6165.95	nM	PMID[527464]
NPT398	Cell Line	UACC-62	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[527464]
NPT400	Cell Line	MDA-MB-435	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[527464]
NPT458	Cell Line	IGROV-1	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[527464]
NPT399	Cell Line	SF-295	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[527464]
NPT403	Cell Line	UACC-257	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[527464]
NPT404	Cell Line	CCRF-CEM	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[527464]
NPT139	Cell Line	HT-29	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[527464]
NPT170	Cell Line	SK-MEL-28	Homo sapiens	GI50	n.a.	18030.18	nM	PMID[527464]
NPT407	Cell Line	COLO 205	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[527464]
NPT1628	Individual Protein	Thrombin	Oryctolagus cuniculus	TT	=	14.2	s	PMID[527465]
NPT1628	Individual Protein	Thrombin	Oryctolagus cuniculus	PT	=	5.4	s	PMID[527465]
NPT1628	Individual Protein	Thrombin	Oryctolagus cuniculus	APTT	=	42.4	s	PMID[527465]
NPT1628	Individual Protein	Thrombin	Oryctolagus cuniculus	Activity	=	8.4	g/L	PMID[527465]
NPT1460	Cell Line	L929	Mus musculus	IC50	>	100000.0	nM	PMID[527466]
NPT1422	Individual Protein	ATP-binding cassette sub-family G member 2	Homo sapiens	FC	=	13.0	n.a.	PMID[527466]
NPT1422	Individual Protein	ATP-binding cassette sub-family G member 2	Homo sapiens	FC	=	19.3	n.a.	PMID[527466]
NPT1594	Individual Protein	Multidrug resistance-associated protein 1	Homo sapiens	FC	=	0.7	n.a.	PMID[527466]
NPT1380	Individual Protein	Avian myoblastosis virus polyprotein II	Avian myeloblastosis virus	Inhibition	=	9.2	%	PMID[527467]
NPT1422	Individual Protein	ATP-binding cassette sub-family G member 2	Homo sapiens	IC50	=	570.0	nM	PMID[527469]
NPT1422	Individual Protein	ATP-binding cassette sub-family G member 2	Homo sapiens	IC50	=	540.0	nM	PMID[527469]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	50000.0	nM	PMID[527471]
NPT1668	Cell Line	NCI-H157	Homo sapiens	IC50	>	50000.0	nM	PMID[527471]
NPT1669	Cell Line	NCI-H1792	Homo sapiens	IC50	>	50000.0	nM	PMID[527471]
NPT455	Cell Line	NCI-H522	Homo sapiens	IC50	>	50000.0	nM	PMID[527471]
NPT379	Cell Line	HOP-62	Homo sapiens	IC50	>	50000.0	nM	PMID[527471]
NPT387	Cell Line	M14	Homo sapiens	IC50	=	380.0	nM	PMID[527471]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	46370.0	nM	PMID[527471]
NPT762	Cell Line	A-431	Homo sapiens	IC50	=	82250.0	nM	PMID[527473]
NPT1719	Cell Line	2008	Homo sapiens	IC50	>	100000.0	nM	PMID[527473]
NPT762	Cell Line	A-431	Homo sapiens	Ratio IC50	=	1.4	n.a.	PMID[527473]
NPT71	Cell Line	HEK293	Homo sapiens	IC50	=	141870.0	nM	PMID[527473]
NPT71	Cell Line	HEK293	Homo sapiens	Ratio IC50	=	1.6	n.a.	PMID[527473]
NPT1083	Cell Line	A-375	Homo sapiens	IC50	=	69720.0	nM	PMID[527473]
NPT148	Cell Line	HCT-15	Homo sapiens	IC50	=	68110.0	nM	PMID[527473]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	100000.0	nM	PMID[527473]
NPT762	Cell Line	A-431	Homo sapiens	IC50	=	57540.0	nM	PMID[527473]
NPT1048	Organism	Poliovirus	Human enterovirus C	Max non-toxic dose	>	50.0	ug ml-1	PMID[527455]
NPT1048	Organism	Poliovirus	Human enterovirus C	Reduction factor	=	1.0	n.a.	PMID[527455]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	73300.0	nM	PMID[527457]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	1.43	ug.mL-1	PMID[527458]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	1.69	ug.mL-1	PMID[527458]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	deltaA	=	0.23	n.a.	PMID[527461]
NPT2	Others	Unspecified		IC50	=	12000.0	nM	PMID[527462]
NPT668	Individual Protein	P-glycoprotein 1	Homo sapiens	IC50	=	16000.0	nM	PMID[527462]
NPT27	Others	Unspecified		IC50	>	100000.0	nM	PMID[527466]
NPT2	Others	Unspecified		FC	=	3.7	n.a.	PMID[527466]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	28000.0	nM	PMID[527470]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	50000.0	nM	PMID[527471]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	10460.0	nM	PMID[527471]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	6530.0	nM	PMID[527471]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	390.0	nM	PMID[527471]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	100000.0	nM	PMID[527473]
NPT23294	CELL-LINE	C13	n.a.	Ratio IC50	=	1.6	n.a.	PMID[527473]
NPT35	Others	n.a.		Activity	=	2.5	%	PMID[527473]
NPT2	Others	Unspecified		IC50	>	50000.0	nM	PMID[527475]
NPT2	Others	Unspecified		Ratio IC50	=	1.6	n.a.	PMID[25906385]
NPT2	Others	Unspecified		IC50	>	100000	nM	PMID[25906385]

☑ 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 NPC236769 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	426
0.1-0.2	1877
0.2-0.3	4806
0.3-0.4	10982
0.4-0.5	6530
0.5-0.6	3706
0.6-0.7	5092
0.7-0.8	4733
0.8-0.85	2267
0.85-0.9	1497
0.9-0.95	570
0.95-1	211

Similarity Score	Similarity Level	Natural Product ID
0.9931	High Similarity	NPC166753
0.9931	High Similarity	NPC50728
0.9863	High Similarity	NPC236223
0.9863	High Similarity	NPC78326
0.9863	High Similarity	NPC179126
0.9863	High Similarity	NPC270620
0.9862	High Similarity	NPC76376
0.9861	High Similarity	NPC159103
0.9796	High Similarity	NPC32557
0.9796	High Similarity	NPC189960
0.9795	High Similarity	NPC82325
0.9795	High Similarity	NPC279989
0.9793	High Similarity	NPC219330
0.9792	High Similarity	NPC261548
0.9792	High Similarity	NPC195202
0.973	High Similarity	NPC178854
0.973	High Similarity	NPC265511
0.9728	High Similarity	NPC246204
0.9728	High Similarity	NPC86485
0.9728	High Similarity	NPC58382
0.9728	High Similarity	NPC162351
0.9726	High Similarity	NPC200740
0.9726	High Similarity	NPC125062
0.9726	High Similarity	NPC252933
0.9726	High Similarity	NPC54394
0.9722	High Similarity	NPC12200
0.9722	High Similarity	NPC33265
0.9722	High Similarity	NPC62536
0.9664	High Similarity	NPC203891
0.9664	High Similarity	NPC110070
0.9664	High Similarity	NPC101830
0.966	High Similarity	NPC123886
0.966	High Similarity	NPC301123
0.966	High Similarity	NPC55205
0.9658	High Similarity	NPC188871
0.9658	High Similarity	NPC149127
0.9658	High Similarity	NPC286342
0.9653	High Similarity	NPC310259
0.96	High Similarity	NPC22472
0.96	High Similarity	NPC176300
0.96	High Similarity	NPC19687
0.96	High Similarity	NPC4481
0.96	High Similarity	NPC204854
0.96	High Similarity	NPC288669
0.96	High Similarity	NPC7846
0.96	High Similarity	NPC18607
0.96	High Similarity	NPC25495
0.96	High Similarity	NPC115798
0.96	High Similarity	NPC9609
0.96	High Similarity	NPC18772
0.96	High Similarity	NPC143828
0.96	High Similarity	NPC191459
0.96	High Similarity	NPC105242
0.96	High Similarity	NPC300943
0.96	High Similarity	NPC152166
0.96	High Similarity	NPC130894
0.96	High Similarity	NPC261004
0.96	High Similarity	NPC253634
0.9597	High Similarity	NPC43243
0.9597	High Similarity	NPC55619
0.9597	High Similarity	NPC200388
0.9597	High Similarity	NPC49824
0.9597	High Similarity	NPC292107
0.9597	High Similarity	NPC245546
0.9597	High Similarity	NPC100916
0.9597	High Similarity	NPC266960
0.9592	High Similarity	NPC28274
0.9592	High Similarity	NPC50403
0.9592	High Similarity	NPC226973
0.9592	High Similarity	NPC308451
0.9592	High Similarity	NPC133953
0.9592	High Similarity	NPC208043
0.9592	High Similarity	NPC260895
0.9589	High Similarity	NPC287101
0.9589	High Similarity	NPC270465
0.9589	High Similarity	NPC87125
0.9589	High Similarity	NPC223579
0.9589	High Similarity	NPC328119
0.9589	High Similarity	NPC183950
0.9589	High Similarity	NPC52005
0.9589	High Similarity	NPC48479
0.9589	High Similarity	NPC137062
0.9589	High Similarity	NPC177298
0.9586	High Similarity	NPC299923
0.9533	High Similarity	NPC75215
0.9533	High Similarity	NPC472438
0.9533	High Similarity	NPC224137
0.9533	High Similarity	NPC7973
0.9533	High Similarity	NPC227192
0.9533	High Similarity	NPC29841
0.9533	High Similarity	NPC287979
0.9533	High Similarity	NPC189179
0.9533	High Similarity	NPC471479
0.9533	High Similarity	NPC305663
0.9533	High Similarity	NPC78302
0.9533	High Similarity	NPC93376
0.9533	High Similarity	NPC471515
0.9533	High Similarity	NPC176665
0.9533	High Similarity	NPC235215
0.9533	High Similarity	NPC163524
0.953	High Similarity	NPC44079
0.953	High Similarity	NPC56786
0.953	High Similarity	NPC201451
0.953	High Similarity	NPC26227
0.953	High Similarity	NPC80534
0.953	High Similarity	NPC133392
0.9527	High Similarity	NPC60972
0.9527	High Similarity	NPC134677
0.9527	High Similarity	NPC39732
0.9524	High Similarity	NPC306821
0.9521	High Similarity	NPC120464
0.947	High Similarity	NPC193842
0.9467	High Similarity	NPC98661
0.9467	High Similarity	NPC471500
0.9467	High Similarity	NPC474520
0.9467	High Similarity	NPC247017
0.9467	High Similarity	NPC268161
0.9463	High Similarity	NPC47781
0.9463	High Similarity	NPC22519
0.9463	High Similarity	NPC176775
0.9463	High Similarity	NPC160951
0.9463	High Similarity	NPC274327
0.9463	High Similarity	NPC255350
0.9463	High Similarity	NPC145379
0.9463	High Similarity	NPC69394
0.9463	High Similarity	NPC183878
0.9463	High Similarity	NPC231018
0.9456	High Similarity	NPC69752
0.9452	High Similarity	NPC108406
0.9444	High Similarity	NPC70853
0.9444	High Similarity	NPC9966
0.9408	High Similarity	NPC246478
0.9408	High Similarity	NPC269906
0.9404	High Similarity	NPC174908
0.9404	High Similarity	NPC67876
0.94	High Similarity	NPC146165
0.94	High Similarity	NPC196439
0.94	High Similarity	NPC138360
0.94	High Similarity	NPC2476
0.94	High Similarity	NPC50715
0.94	High Similarity	NPC4455
0.94	High Similarity	NPC213622
0.94	High Similarity	NPC280339
0.94	High Similarity	NPC167815
0.94	High Similarity	NPC214138
0.94	High Similarity	NPC201136
0.94	High Similarity	NPC163780
0.94	High Similarity	NPC20830
0.94	High Similarity	NPC128863
0.94	High Similarity	NPC183597
0.94	High Similarity	NPC227325
0.94	High Similarity	NPC92659
0.94	High Similarity	NPC256612
0.9396	High Similarity	NPC471982
0.9396	High Similarity	NPC275722
0.9396	High Similarity	NPC239128
0.9396	High Similarity	NPC25270
0.9396	High Similarity	NPC71334
0.9396	High Similarity	NPC37684
0.9396	High Similarity	NPC304954
0.9396	High Similarity	NPC100887
0.9396	High Similarity	NPC301323
0.9396	High Similarity	NPC187498
0.9396	High Similarity	NPC156222
0.9396	High Similarity	NPC63187
0.9396	High Similarity	NPC131624
0.9396	High Similarity	NPC198826
0.9396	High Similarity	NPC188203
0.9396	High Similarity	NPC293183
0.9396	High Similarity	NPC241498
0.9396	High Similarity	NPC162313
0.9396	High Similarity	NPC120163
0.9396	High Similarity	NPC275836
0.9396	High Similarity	NPC256283
0.9396	High Similarity	NPC222830
0.9396	High Similarity	NPC212678
0.9396	High Similarity	NPC57030
0.9396	High Similarity	NPC157784
0.9396	High Similarity	NPC83508
0.9392	High Similarity	NPC259058
0.9392	High Similarity	NPC201547
0.9392	High Similarity	NPC338131
0.9384	High Similarity	NPC20791
0.9384	High Similarity	NPC179271
0.9379	High Similarity	NPC113089
0.9375	High Similarity	NPC29536
0.9375	High Similarity	NPC90582
0.9375	High Similarity	NPC262094
0.9342	High Similarity	NPC280680
0.9342	High Similarity	NPC152904
0.9342	High Similarity	NPC195832
0.9338	High Similarity	NPC326037
0.9338	High Similarity	NPC320825
0.9338	High Similarity	NPC13858
0.9333	High Similarity	NPC250822
0.9333	High Similarity	NPC280937
0.9333	High Similarity	NPC276409
0.9333	High Similarity	NPC75279
0.9333	High Similarity	NPC472915
0.9333	High Similarity	NPC18727

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 NPC236769 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	398
0.1-0.2	985
0.2-0.3	1739
0.3-0.4	2645
0.4-0.5	1800
0.5-0.6	1021
0.6-0.7	375
0.7-0.8	126
0.8-0.85	36
0.85-0.9	16
0.9-0.95	8
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9463	High Similarity	NPD2801	Approved
0.94	High Similarity	NPD3817	Phase 2
0.9384	High Similarity	NPD1512	Approved
0.9338	High Similarity	NPD3882	Suspended
0.9267	High Similarity	NPD1934	Approved
0.9247	High Similarity	NPD1511	Approved
0.9184	High Similarity	NPD4378	Clinical (unspecified phase)
0.9079	High Similarity	NPD2393	Clinical (unspecified phase)
0.9045	High Similarity	NPD6167	Clinical (unspecified phase)
0.9045	High Similarity	NPD6166	Phase 2
0.9045	High Similarity	NPD6168	Clinical (unspecified phase)
0.8889	High Similarity	NPD7808	Phase 3
0.8882	High Similarity	NPD6797	Phase 2
0.8827	High Similarity	NPD7251	Discontinued
0.8773	High Similarity	NPD4338	Clinical (unspecified phase)
0.8758	High Similarity	NPD7054	Approved
0.8733	High Similarity	NPD6799	Approved
0.8704	High Similarity	NPD7472	Approved
0.8696	High Similarity	NPD3818	Discontinued
0.8662	High Similarity	NPD7075	Discontinued
0.859	High Similarity	NPD7096	Clinical (unspecified phase)
0.8589	High Similarity	NPD7074	Phase 3
0.8581	High Similarity	NPD1550	Clinical (unspecified phase)
0.8581	High Similarity	NPD1552	Clinical (unspecified phase)
0.8571	High Similarity	NPD1510	Phase 2
0.8526	High Similarity	NPD6801	Discontinued
0.8523	High Similarity	NPD1549	Phase 2
0.8516	High Similarity	NPD4380	Phase 2
0.8514	High Similarity	NPD2796	Approved
0.8447	Intermediate Similarity	NPD6232	Discontinued
0.8438	Intermediate Similarity	NPD5494	Approved
0.8431	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8428	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8425	Intermediate Similarity	NPD1240	Approved
0.8418	Intermediate Similarity	NPD5402	Approved
0.8415	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8405	Intermediate Similarity	NPD7473	Discontinued
0.8397	Intermediate Similarity	NPD6599	Discontinued
0.8385	Intermediate Similarity	NPD1247	Approved
0.8375	Intermediate Similarity	NPD919	Approved
0.8365	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8323	Intermediate Similarity	NPD5403	Approved
0.8311	Intermediate Similarity	NPD1607	Approved
0.8282	Intermediate Similarity	NPD3926	Phase 2
0.8278	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8239	Intermediate Similarity	NPD7819	Suspended
0.8194	Intermediate Similarity	NPD5401	Approved
0.8187	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8113	Intermediate Similarity	NPD7411	Suspended
0.8095	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8084	Intermediate Similarity	NPD5844	Phase 1
0.8054	Intermediate Similarity	NPD943	Approved
0.8052	Intermediate Similarity	NPD3750	Approved
0.8049	Intermediate Similarity	NPD6959	Discontinued
0.8012	Intermediate Similarity	NPD1465	Phase 2
0.8	Intermediate Similarity	NPD447	Suspended
0.7975	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7919	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7908	Intermediate Similarity	NPD2935	Discontinued
0.7908	Intermediate Similarity	NPD1551	Phase 2
0.7905	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7871	Intermediate Similarity	NPD2800	Approved
0.7844	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7843	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7838	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7836	Intermediate Similarity	NPD6559	Discontinued
0.7815	Intermediate Similarity	NPD1613	Approved
0.7815	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7805	Intermediate Similarity	NPD7768	Phase 2
0.7798	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7785	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7763	Intermediate Similarity	NPD1933	Approved
0.7763	Intermediate Similarity	NPD230	Phase 1
0.7758	Intermediate Similarity	NPD3749	Approved
0.7756	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7736	Intermediate Similarity	NPD2533	Approved
0.7736	Intermediate Similarity	NPD2532	Approved
0.7736	Intermediate Similarity	NPD2534	Approved
0.7733	Intermediate Similarity	NPD3027	Phase 3
0.7727	Intermediate Similarity	NPD3748	Approved
0.7707	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7706	Intermediate Similarity	NPD3751	Discontinued
0.7679	Intermediate Similarity	NPD3787	Discontinued
0.7677	Intermediate Similarity	NPD6099	Approved
0.7677	Intermediate Similarity	NPD6100	Approved
0.7658	Intermediate Similarity	NPD6190	Approved
0.7643	Intermediate Similarity	NPD1243	Approved
0.764	Intermediate Similarity	NPD920	Approved
0.7628	Intermediate Similarity	NPD2344	Approved
0.7619	Intermediate Similarity	NPD7199	Phase 2
0.7597	Intermediate Similarity	NPD6651	Approved
0.7595	Intermediate Similarity	NPD4628	Phase 3
0.7586	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7584	Intermediate Similarity	NPD1203	Approved
0.7568	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7566	Intermediate Similarity	NPD2313	Discontinued
0.7546	Intermediate Similarity	NPD3226	Approved
0.7541	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7517	Intermediate Similarity	NPD1548	Phase 1
0.7516	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD2799	Discontinued
0.75	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD2403	Approved
0.7485	Intermediate Similarity	NPD1653	Approved
0.7483	Intermediate Similarity	NPD9494	Approved
0.7473	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7471	Intermediate Similarity	NPD5953	Discontinued
0.7457	Intermediate Similarity	NPD7286	Phase 2
0.7453	Intermediate Similarity	NPD7390	Discontinued
0.7451	Intermediate Similarity	NPD3268	Approved
0.7451	Intermediate Similarity	NPD6798	Discontinued
0.7444	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7438	Intermediate Similarity	NPD2309	Approved
0.7434	Intermediate Similarity	NPD6832	Phase 2
0.7434	Intermediate Similarity	NPD4908	Phase 1
0.7432	Intermediate Similarity	NPD422	Phase 1
0.7419	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7417	Intermediate Similarity	NPD2798	Approved
0.741	Intermediate Similarity	NPD37	Approved
0.7405	Intermediate Similarity	NPD2346	Discontinued
0.7403	Intermediate Similarity	NPD6233	Phase 2
0.7396	Intermediate Similarity	NPD6234	Discontinued
0.7389	Intermediate Similarity	NPD7033	Discontinued
0.7384	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7383	Intermediate Similarity	NPD9717	Approved
0.7381	Intermediate Similarity	NPD4966	Approved
0.7381	Intermediate Similarity	NPD4965	Approved
0.7381	Intermediate Similarity	NPD4967	Phase 2
0.7375	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD3018	Phase 2
0.736	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7351	Intermediate Similarity	NPD2797	Approved
0.7338	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD5536	Phase 2
0.7326	Intermediate Similarity	NPD5242	Approved
0.7315	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD1610	Phase 2
0.7312	Intermediate Similarity	NPD2654	Approved
0.7308	Intermediate Similarity	NPD6355	Discontinued
0.7285	Intermediate Similarity	NPD3225	Approved
0.7278	Intermediate Similarity	NPD4308	Phase 3
0.7268	Intermediate Similarity	NPD4360	Phase 2
0.7268	Intermediate Similarity	NPD4363	Phase 3
0.7267	Intermediate Similarity	NPD1608	Approved
0.7246	Intermediate Similarity	NPD6385	Approved
0.7246	Intermediate Similarity	NPD6386	Approved
0.7244	Intermediate Similarity	NPD4060	Phase 1
0.7239	Intermediate Similarity	NPD4357	Discontinued
0.7232	Intermediate Similarity	NPD7685	Pre-registration
0.7226	Intermediate Similarity	NPD411	Approved
0.7222	Intermediate Similarity	NPD8434	Phase 2
0.7222	Intermediate Similarity	NPD2354	Approved
0.7219	Intermediate Similarity	NPD2983	Phase 2
0.7219	Intermediate Similarity	NPD2982	Phase 2
0.7219	Intermediate Similarity	NPD5353	Approved
0.7202	Intermediate Similarity	NPD6844	Discontinued
0.72	Intermediate Similarity	NPD2163	Approved
0.7195	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7195	Intermediate Similarity	NPD3688	Clinical (unspecified phase)
0.7195	Intermediate Similarity	NPD3146	Approved
0.7188	Intermediate Similarity	NPD1471	Phase 3
0.7168	Intermediate Similarity	NPD5710	Approved
0.7168	Intermediate Similarity	NPD5711	Approved
0.7161	Intermediate Similarity	NPD7095	Approved
0.7161	Intermediate Similarity	NPD4625	Phase 3
0.7152	Intermediate Similarity	NPD9269	Phase 2
0.7152	Intermediate Similarity	NPD2981	Phase 2
0.7135	Intermediate Similarity	NPD4361	Phase 2
0.7135	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD3266	Approved
0.7124	Intermediate Similarity	NPD3267	Approved
0.7118	Intermediate Similarity	NPD4288	Approved
0.7117	Intermediate Similarity	NPD3887	Approved
0.7114	Intermediate Similarity	NPD9268	Approved
0.7105	Intermediate Similarity	NPD4749	Approved
0.7102	Intermediate Similarity	NPD7228	Approved
0.7099	Intermediate Similarity	NPD1652	Phase 2
0.7089	Intermediate Similarity	NPD4340	Discontinued
0.7086	Intermediate Similarity	NPD1201	Approved
0.7081	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD2353	Approved
0.7074	Intermediate Similarity	NPD6782	Approved
0.7074	Intermediate Similarity	NPD6779	Approved
0.7074	Intermediate Similarity	NPD6777	Approved
0.7074	Intermediate Similarity	NPD6778	Approved
0.7074	Intermediate Similarity	NPD6781	Approved
0.7074	Intermediate Similarity	NPD6780	Approved
0.7074	Intermediate Similarity	NPD6776	Approved
0.707	Intermediate Similarity	NPD4062	Phase 3
0.7069	Intermediate Similarity	NPD7229	Phase 3
0.7067	Intermediate Similarity	NPD17	Approved
0.7056	Intermediate Similarity	NPD8313	Approved
0.7056	Intermediate Similarity	NPD8312	Approved
0.7053	Intermediate Similarity	NPD7435	Discontinued
0.7048	Intermediate Similarity	NPD5049	Phase 3
0.7047	Intermediate Similarity	NPD9545	Approved
0.7041	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD7038	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