NPASS Compound

Structure

CID204985 OpenBabel06191715592D 30 32 0 0 0 0 0 0 0 0999 V2000 5.1962 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 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 4.3301 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 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 3.0000 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 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 14 1 0 0 0 0 2 14 1 0 0 0 0 3 15 1 0 0 0 0 4 15 1 0 0 0 0 5 11 1 0 0 0 0 5 14 2 0 0 0 0 6 12 1 0 0 0 0 6 15 2 0 0 0 0 7 9 1 0 0 0 0 7 16 2 0 0 0 0 8 10 2 0 0 0 0 8 16 1 0 0 0 0 9 17 2 0 0 0 0 10 17 1 0 0 0 0 11 18 1 0 0 0 0 12 19 1 0 0 0 0 13 20 2 0 0 0 0 13 30 1 0 0 0 0 16 20 1 0 0 0 0 17 26 1 0 0 0 0 18 22 2 0 0 0 0 18 23 1 0 0 0 0 19 22 1 0 0 0 0 19 25 2 0 0 0 0 20 24 1 0 0 0 0 21 23 2 0 0 0 0 21 24 1 0 0 0 0 21 25 1 0 0 0 0 22 27 1 0 0 0 0 23 28 1 0 0 0 0 24 29 2 0 0 0 0 25 30 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	406.18
Volume:	432.873
LogP:	6.321
LogD:	3.238
LogS:	-3.119
# Rotatable Bonds:	5
TPSA:	90.9
# H-Bond Aceptor:	5
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.48
Synthetic Accessibility Score:	3.001
Fsp3:	0.24
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.828
MDCK Permeability:	1.326249821431702e-05
Pgp-inhibitor:	0.515
Pgp-substrate:	0.474
Human Intestinal Absorption (HIA):	0.018
20% Bioavailability (F20%):	0.957
30% Bioavailability (F30%):	0.361

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.007
Plasma Protein Binding (PPB):	90.82225799560547%
Volume Distribution (VD):	1.031
Pgp-substrate:	9.695008277893066%

ADMET: Metabolism

CYP1A2-inhibitor:	0.494
CYP1A2-substrate:	0.151
CYP2C19-inhibitor:	0.859
CYP2C19-substrate:	0.056
CYP2C9-inhibitor:	0.851
CYP2C9-substrate:	0.904
CYP2D6-inhibitor:	0.126
CYP2D6-substrate:	0.223
CYP3A4-inhibitor:	0.138
CYP3A4-substrate:	0.07

ADMET: Excretion

Clearance (CL):	7.811
Half-life (T1/2):	0.449

ADMET: Toxicity

hERG Blockers:	0.021
Human Hepatotoxicity (H-HT):	0.833
Drug-inuced Liver Injury (DILI):	0.7
AMES Toxicity:	0.015
Rat Oral Acute Toxicity:	0.717
Maximum Recommended Daily Dose:	0.025
Skin Sensitization:	0.886
Carcinogencity:	0.119
Eye Corrosion:	0.003
Eye Irritation:	0.098
Respiratory Toxicity:	0.123

Download Data

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

Natural Product: NPC204985

Natural Product ID:	NPC204985
*Common Name:**	5,7-Dihydroxy-3-(4-Hydroxyphenyl)-6,8-Bis(3-Methylbut-2-Enyl)Chromen-4-One
IUPAC Name:	5,7-dihydroxy-3-(4-hydroxyphenyl)-6,8-bis(3-methylbut-2-enyl)chromen-4-one
Synonyms:
Standard InCHIKey:	UCHYSPNEUSDFQR-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C25H26O5/c1-14(2)5-11-18-22(27)19(12-6-15(3)4)25-21(23(18)28)24(29)20(13-30-25)16-7-9-17(26)10-8-16/h5-10,13,26-28H,11-12H2,1-4H3
SMILES:	CC(=CCc1c(O)c(CC=C(C)C)c2c(c1O)c(=O)c(co2)c1ccc(cc1)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL494252
PubChem CID:	480783
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002506] Isoflavonoids [CHEMONTID:0001612] Isoflavans [CHEMONTID:0001827] Isoflavanones [CHEMONTID:0003526] 6-prenylated isoflavanones

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO27553	Derris scandens	Species	Fabaceae	Eukaryota	n.a.	stem	n.a.	DOI[10.1016/S0031-9422(99)00103-X]
NPO29113	Erythrina vogelii	Species	Fabaceae	Eukaryota	root bark	n.a.	n.a.	PMID[11908991]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[12713396]
NPO30804	Cudrania tricuspidata	Species	Moraceae	Eukaryota	n.a.	root	n.a.	PMID[15787460]
NPO30804	Cudrania tricuspidata	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15787460]
NPO28587	Axinella weltneri	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[16124780]
NPO30804	Cudrania tricuspidata	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16203143]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	root	n.a.	PMID[16441081]
NPO22654	Millettia pachycarpa	Species	Fabaceae	Eukaryota	n.a.	leaf	n.a.	PMID[16441086]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16675659]
NPO30804	Cudrania tricuspidata	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16919944]
NPO30804	Cudrania tricuspidata	Species	Moraceae	Eukaryota	root bark	n.a.	n.a.	PMID[17608532]
NPO30804	Cudrania tricuspidata	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17950599]
NPO30804	Cudrania tricuspidata	Species	Moraceae	Eukaryota	fruits	n.a.	n.a.	PMID[19113968]
NPO30804	Cudrania tricuspidata	Species	Moraceae	Eukaryota	Roots	n.a.	n.a.	PMID[19191562]
NPO30804	Cudrania tricuspidata	Species	Moraceae	Eukaryota	n.a.	root	n.a.	PMID[19280148]
NPO30804	Cudrania tricuspidata	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19285413]
NPO30804	Cudrania tricuspidata	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19660948]
NPO27553	Derris scandens	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19969457]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	roots	n.a.	n.a.	PMID[20022509]
NPO1698	Glycyrrhiza inflata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21123068]
NPO27553	Derris scandens	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21314138]
NPO30804	Cudrania tricuspidata	Species	Moraceae	Eukaryota	n.a.	root	n.a.	PMID[21319773]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21866899]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	root	n.a.	PMID[22074222]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22074222]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23325115]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	Roots	n.a.	n.a.	PMID[23541646]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	rhizome	n.a.	PMID[23867078]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	root	n.a.	PMID[23867078]
NPO4010	Flemingia philippinensis	Species	Fabaceae	Eukaryota	Roots	n.a.	n.a.	PMID[24054487]
NPO4010	Flemingia philippinensis	Species	Fabaceae	Eukaryota	roots	n.a.	n.a.	PMID[24412339]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24479468]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	roots	n.a.	n.a.	PMID[24957203]
NPO30804	Cudrania tricuspidata	Species	Moraceae	Eukaryota	Roots	n.a.	n.a.	PMID[25322455]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25445757]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25744461]
NPO28764	Phyllidia ocellata	Species	Phyllidiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[26056748]
NPO30804	Cudrania tricuspidata	Species	Moraceae	Eukaryota	root barks	purchased from the local herbal market, Chungbuk, Korea	2012-JUL	PMID[26227773]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26841168]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28140583]
NPO1698	Glycyrrhiza inflata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28522265]
NPO1698	Glycyrrhiza inflata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[29641206]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32196343]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7381508]
NPO28587	Axinella weltneri	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[9249974]
NPO27553	Derris scandens	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29113	Erythrina vogelii	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1698	Glycyrrhiza inflata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO4010	Flemingia philippinensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12908	Euchresta japonica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO30804	Cudrania tricuspidata	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22654	Millettia pachycarpa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28553	Nannoglottis ravida	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29113	Erythrina vogelii	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1698	Glycyrrhiza inflata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22654	Millettia pachycarpa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12908	Euchresta japonica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27553	Derris scandens	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4010	Flemingia philippinensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO4010	Flemingia philippinensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO1698	Glycyrrhiza inflata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO30804	Cudrania tricuspidata	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO22654	Millettia pachycarpa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO1698	Glycyrrhiza inflata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10026	Mitracarpus scaber	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4010	Flemingia philippinensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28553	Nannoglottis ravida	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5436	Absidia caerulea	Species	Cunninghamellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29056	Dactynotus ambrosiae	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO12908	Euchresta japonica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1698	Glycyrrhiza inflata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28399	Anthotroche myoporoides	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28436	Helenium virginicum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28587	Axinella weltneri	Species	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO28517	Hypericum caprifoliatum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28944	Heliotropium digynum	Species	Heliotropiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7786	Lentinus tigrinus	Species	Lentinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22654	Millettia pachycarpa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28764	Phyllidia ocellata	Species	Phyllidiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29181	Galdieria sulphuraria	Species	Cyanidiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25617	Lactococcus lactis	Species	Streptococcaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO29113	Erythrina vogelii	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28535	Astragalus flexus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28640	Alsidium corallinum	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27553	Derris scandens	Species	Fabaceae	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
AC50	2
EC50	3
IC50	8
Ki	2
Others	14
Potency	32

Activity Type	# Activity
Cell Line	9
CELL-LINE	1
Individual Protein	34
Organism	6
Others	11

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	19200.0	nM	PMID[531678]
NPT51	Individual Protein	Microtubule-associated protein tau	Homo sapiens	Potency	=	15848.9	nM	PMID[531679]
NPT51	Individual Protein	Microtubule-associated protein tau	Homo sapiens	Potency	=	39810.7	nM	PMID[531679]
NPT531	Individual Protein	Nuclear receptor ROR-gamma	Mus musculus	Potency	=	31622.8	nM	PMID[531679]
NPT442	Individual Protein	Ferritin light chain	Equus caballus	Potency	=	19952.6	nM	PMID[531679]
NPT51	Individual Protein	Microtubule-associated protein tau	Homo sapiens	Potency	=	14125.4	nM	PMID[531679]
NPT282	Individual Protein	MAP kinase ERK2	Homo sapiens	Potency	=	19952.6	nM	PMID[531679]
NPT1254	Individual Protein	Streptokinase A	Streptococcus pyogenes serotype M1	EC50	=	1863.0	nM	PMID[531679]
NPT531	Individual Protein	Nuclear receptor ROR-gamma	Mus musculus	Potency	=	398.1	nM	PMID[531679]
NPT61	Individual Protein	Beta-glucocerebrosidase	Homo sapiens	Potency	n.a.	12589.3	nM	PMID[531679]
NPT532	Individual Protein	Lysine-specific demethylase 4A	Homo sapiens	Potency	n.a.	44668.4	nM	PMID[531679]
NPT152	Individual Protein	Nuclear factor erythroid 2-related factor 2	Homo sapiens	Potency	n.a.	29092.9	nM	PMID[531679]
NPT64	Individual Protein	ATPase family AAA domain-containing protein 5	Homo sapiens	Potency	n.a.	29081.0	nM	PMID[531679]
NPT65	Cell Line	HepG2	Homo sapiens	Potency	n.a.	22387.2	nM	PMID[531679]
NPT154	Individual Protein	Mothers against decapentaplegic homolog 3	Homo sapiens	Potency	n.a.	25118.9	nM	PMID[531679]
NPT484	Individual Protein	Luciferin 4-monooxygenase	Photinus pyralis	Potency	n.a.	37933.0	nM	PMID[531679]
NPT10	Individual Protein	Geminin	Homo sapiens	Potency	n.a.	9200.0	nM	PMID[531679]
NPT10	Individual Protein	Geminin	Homo sapiens	Potency	n.a.	29092.9	nM	PMID[531679]
NPT478	Individual Protein	Ataxin-2	Homo sapiens	Potency	n.a.	39810.7	nM	PMID[531679]
NPT101	Individual Protein	Glucagon-like peptide 1 receptor	Homo sapiens	Potency	n.a.	11220.2	nM	PMID[531679]
NPT159	Individual Protein	Aberrant vpr protein	Human immunodeficiency virus 1	Potency	n.a.	63095.7	nM	PMID[531679]
NPT1043	Individual Protein	Glycoprotein hormones alpha chain	Homo sapiens	Potency	n.a.	28183.8	nM	PMID[531679]
NPT50	Individual Protein	Tyrosyl-DNA phosphodiesterase 1	Homo sapiens	Potency	n.a.	25929.0	nM	PMID[531679]
NPT50	Individual Protein	Tyrosyl-DNA phosphodiesterase 1	Homo sapiens	Potency	n.a.	18356.4	nM	PMID[531679]
NPT344	Individual Protein	Sialidase	Clostridium perfringens	Ki	=	4290.0	nM	PMID[531680]
NPT344	Individual Protein	Sialidase	Clostridium perfringens	IC50	=	4040.0	nM	PMID[531680]
NPT535	Individual Protein	Parathyroid hormone receptor	Homo sapiens	Potency	n.a.	44668.4	nM	PMID[531679]
NPT1120	Individual Protein	Pancreatic triacylglycerol lipase	Sus scrofa	IC50	=	65000.0	nM	PMID[531681]
NPT1120	Individual Protein	Pancreatic triacylglycerol lipase	Sus scrofa	Inhibition	=	72.2	%	PMID[531681]
NPT178	Individual Protein	Protein-tyrosine phosphatase 1B	Homo sapiens	IC50	=	9300.0	nM	PMID[531682]
NPT178	Individual Protein	Protein-tyrosine phosphatase 1B	Homo sapiens	Ki	=	9600.0	nM	PMID[531682]
NPT178	Individual Protein	Protein-tyrosine phosphatase 1B	Homo sapiens	Inhibition	>	95.0	%	PMID[531683]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	8580.0	nM	PMID[531684]
NPT660	Cell Line	SW480	Homo sapiens	IC50	=	8080.0	nM	PMID[531684]
NPT83	Cell Line	MCF7	Homo sapiens	GI	=	73.0	%	PMID[531684]
NPT660	Cell Line	SW480	Homo sapiens	GI	=	81.0	%	PMID[531684]
NPT65	Cell Line	HepG2	Homo sapiens	GI	=	30.0	%	PMID[531684]
NPT2615	Cell Line	HEK-293T	Homo sapiens	GI	=	49.0	%	PMID[531684]
NPT113	Cell Line	RAW264.7	Mus musculus	Inhibition	=	22.0	%	PMID[531684]
NPT178	Individual Protein	Protein-tyrosine phosphatase 1B	Homo sapiens	Inhibition	=	51.0	%	PMID[531684]
NPT152	Individual Protein	Nuclear factor erythroid 2-related factor 2	Homo sapiens	FC	=	1.21	n.a.	PMID[531685]
NPT178	Individual Protein	Protein-tyrosine phosphatase 1B	Homo sapiens	IC50	=	2300.0	nM	PMID[531686]
NPT878	Organism	Streptococcus mutans	Streptococcus mutans	Activity	=	2.0	ug ml-1	PMID[531677]
NPT174	Organism	Streptococcus	Streptococcus	EC50	=	3281.0	nM	PMID[531679]
NPT1252	Organism	Streptococcus sp. 'group A'	Streptococcus sp. 'group A'	EC50	=	2660.0	nM	PMID[531679]
NPT312	Organism	Saccharomyces cerevisiae	Saccharomyces cerevisiae	Potency	=	35481.3	nM	PMID[531679]
NPT2	Others	Unspecified		Potency	=	23109.3	nM	PMID[531679]
NPT2	Others	Unspecified		AC50	=	2616.0	nM	PMID[531679]
NPT2	Others	Unspecified		Potency	n.a.	32642.7	nM	PMID[531679]
NPT2	Others	Unspecified		Potency	n.a.	5623.4	nM	PMID[531679]
NPT2	Others	Unspecified		AC50	=	3494.0	nM	PMID[531679]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Potency	n.a.	2936.2	nM	PMID[531679]
NPT2	Others	Unspecified		Potency	n.a.	28183.8	nM	PMID[531679]
NPT2	Others	Unspecified		Potency	n.a.	3162.3	nM	PMID[531679]
NPT2	Others	Unspecified		Potency	n.a.	29092.9	nM	PMID[531679]
NPT861	Individual Protein	Isocitrate dehydrogenase [NADP] cytoplasmic	Homo sapiens	Potency	n.a.	29092.9	nM	PMID[531679]
NPT742	Organism	Influenza A virus	Influenza A virus	Activity	>	30.0	%	PMID[531683]
NPT21742	CELL-LINE	L02	Homo sapiens	GI	=	12.0	%	PMID[531684]
NPT2	Others	Unspecified		Inhibition	=	26.0	%	PMID[531684]
NPT2	Others	Unspecified		Inhibition	=	7.0	%	PMID[531684]
NPT2	Others	Unspecified		IC50	=	16300.0	nM	PMID[531686]

☑ 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 NPC204985 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	391
0.1-0.2	1579
0.2-0.3	3841
0.3-0.4	10204
0.4-0.5	8329
0.5-0.6	3741
0.6-0.7	5714
0.7-0.8	4735
0.8-0.85	2004
0.85-0.9	1464
0.9-0.95	577
0.95-1	118

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC80962
1.0	High Similarity	NPC219917
1.0	High Similarity	NPC172250
1.0	High Similarity	NPC259166
1.0	High Similarity	NPC215311
1.0	High Similarity	NPC326109
1.0	High Similarity	NPC213659
1.0	High Similarity	NPC144118
1.0	High Similarity	NPC48624
0.9926	High Similarity	NPC52789
0.9926	High Similarity	NPC26051
0.9926	High Similarity	NPC55832
0.9926	High Similarity	NPC469404
0.9926	High Similarity	NPC268204
0.9925	High Similarity	NPC295384
0.9925	High Similarity	NPC283429
0.9852	High Similarity	NPC101366
0.9852	High Similarity	NPC253822
0.9781	High Similarity	NPC117836
0.9781	High Similarity	NPC475705
0.9781	High Similarity	NPC476178
0.9781	High Similarity	NPC51887
0.9776	High Similarity	NPC181124
0.9776	High Similarity	NPC209560
0.9776	High Similarity	NPC162680
0.9776	High Similarity	NPC7013
0.9776	High Similarity	NPC303644
0.9776	High Similarity	NPC294409
0.9776	High Similarity	NPC116632
0.971	High Similarity	NPC476055
0.9704	High Similarity	NPC12175
0.9704	High Similarity	NPC21350
0.9704	High Similarity	NPC278323
0.9704	High Similarity	NPC55162
0.9704	High Similarity	NPC309154
0.9704	High Similarity	NPC279668
0.9704	High Similarity	NPC90665
0.9701	High Similarity	NPC66349
0.9701	High Similarity	NPC168105
0.9701	High Similarity	NPC186838
0.9701	High Similarity	NPC98115
0.9701	High Similarity	NPC249606
0.9701	High Similarity	NPC150399
0.9701	High Similarity	NPC12165
0.9701	High Similarity	NPC477243
0.9701	High Similarity	NPC274109
0.9701	High Similarity	NPC41461
0.9701	High Similarity	NPC1486
0.9701	High Similarity	NPC25287
0.9701	High Similarity	NPC477244
0.9701	High Similarity	NPC477242
0.9635	High Similarity	NPC110969
0.9635	High Similarity	NPC470087
0.9635	High Similarity	NPC321980
0.9635	High Similarity	NPC470089
0.9632	High Similarity	NPC477956
0.9632	High Similarity	NPC470211
0.963	High Similarity	NPC472419
0.963	High Similarity	NPC153979
0.963	High Similarity	NPC317119
0.9627	High Similarity	NPC39426
0.9627	High Similarity	NPC13575
0.9627	High Similarity	NPC234560
0.9627	High Similarity	NPC156092
0.9627	High Similarity	NPC131039
0.9571	High Similarity	NPC237635
0.9571	High Similarity	NPC222298
0.9571	High Similarity	NPC79469
0.9571	High Similarity	NPC104406
0.9571	High Similarity	NPC51070
0.9571	High Similarity	NPC24673
0.9571	High Similarity	NPC201731
0.9571	High Similarity	NPC97716
0.9568	High Similarity	NPC234629
0.9568	High Similarity	NPC311741
0.9565	High Similarity	NPC226636
0.9565	High Similarity	NPC11561
0.9562	High Similarity	NPC11056
0.9562	High Similarity	NPC261227
0.9562	High Similarity	NPC241100
0.9562	High Similarity	NPC270883
0.9562	High Similarity	NPC159275
0.9562	High Similarity	NPC172986
0.9559	High Similarity	NPC471620
0.9559	High Similarity	NPC251681
0.9559	High Similarity	NPC243528
0.9556	High Similarity	NPC235428
0.9556	High Similarity	NPC87545
0.9552	High Similarity	NPC103842
0.9552	High Similarity	NPC286336
0.9504	High Similarity	NPC266572
0.9504	High Similarity	NPC168085
0.9504	High Similarity	NPC6511
0.9496	High Similarity	NPC257097
0.9496	High Similarity	NPC143896
0.9496	High Similarity	NPC18585
0.9496	High Similarity	NPC175504
0.9496	High Similarity	NPC166138
0.9496	High Similarity	NPC221432
0.9496	High Similarity	NPC169591
0.9496	High Similarity	NPC68104
0.9496	High Similarity	NPC301751
0.9496	High Similarity	NPC150408
0.9496	High Similarity	NPC106985
0.9496	High Similarity	NPC164980
0.9496	High Similarity	NPC149026
0.9496	High Similarity	NPC75049
0.9496	High Similarity	NPC245482
0.9496	High Similarity	NPC39329
0.9496	High Similarity	NPC310130
0.9496	High Similarity	NPC91560
0.9493	High Similarity	NPC205006
0.9493	High Similarity	NPC103362
0.9493	High Similarity	NPC156590
0.9493	High Similarity	NPC3188
0.9493	High Similarity	NPC64908
0.9493	High Similarity	NPC147688
0.9493	High Similarity	NPC118840
0.9493	High Similarity	NPC282300
0.9489	High Similarity	NPC216978
0.9489	High Similarity	NPC472366
0.9489	High Similarity	NPC301217
0.9489	High Similarity	NPC303633
0.9489	High Similarity	NPC53181
0.9489	High Similarity	NPC217186
0.9489	High Similarity	NPC55018
0.9489	High Similarity	NPC18260
0.9489	High Similarity	NPC96565
0.9489	High Similarity	NPC220062
0.9489	High Similarity	NPC78913
0.9485	High Similarity	NPC212767
0.9478	High Similarity	NPC472365
0.9478	High Similarity	NPC139813
0.9478	High Similarity	NPC188646
0.9478	High Similarity	NPC242294
0.9478	High Similarity	NPC192304
0.9478	High Similarity	NPC20560
0.9478	High Similarity	NPC144051
0.9478	High Similarity	NPC27643
0.9478	High Similarity	NPC294593
0.9478	High Similarity	NPC159623
0.9478	High Similarity	NPC337373
0.9478	High Similarity	NPC28753
0.9478	High Similarity	NPC312318
0.9478	High Similarity	NPC175098
0.9478	High Similarity	NPC82225
0.9478	High Similarity	NPC263670
0.9478	High Similarity	NPC56031
0.9478	High Similarity	NPC223354
0.9478	High Similarity	NPC18877
0.9478	High Similarity	NPC204960
0.9437	High Similarity	NPC171916
0.9437	High Similarity	NPC38545
0.9437	High Similarity	NPC317492
0.9433	High Similarity	NPC296998
0.9433	High Similarity	NPC473077
0.9433	High Similarity	NPC110303
0.9433	High Similarity	NPC23728
0.9429	High Similarity	NPC273538
0.9429	High Similarity	NPC319752
0.9429	High Similarity	NPC473015
0.9429	High Similarity	NPC197252
0.9429	High Similarity	NPC236766
0.9429	High Similarity	NPC473013
0.9429	High Similarity	NPC271288
0.9429	High Similarity	NPC209040
0.9429	High Similarity	NPC216538
0.9429	High Similarity	NPC224714
0.9424	High Similarity	NPC297600
0.9424	High Similarity	NPC148757
0.9424	High Similarity	NPC76372
0.9424	High Similarity	NPC32739
0.9424	High Similarity	NPC66515
0.9424	High Similarity	NPC107572
0.9424	High Similarity	NPC324134
0.9424	High Similarity	NPC161506
0.9424	High Similarity	NPC324436
0.9424	High Similarity	NPC194432
0.9424	High Similarity	NPC220998
0.9424	High Similarity	NPC167624
0.9424	High Similarity	NPC37496
0.9424	High Similarity	NPC166934
0.9424	High Similarity	NPC76338
0.9424	High Similarity	NPC1089
0.9424	High Similarity	NPC64915
0.9424	High Similarity	NPC227579
0.9424	High Similarity	NPC228504
0.9424	High Similarity	NPC78
0.9424	High Similarity	NPC166482
0.9424	High Similarity	NPC223500
0.9424	High Similarity	NPC328164
0.9424	High Similarity	NPC177354
0.9424	High Similarity	NPC10937
0.9424	High Similarity	NPC265040
0.9424	High Similarity	NPC40833
0.9424	High Similarity	NPC125855
0.9424	High Similarity	NPC182852
0.9424	High Similarity	NPC296917
0.9424	High Similarity	NPC144499
0.9424	High Similarity	NPC306829

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 NPC204985 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	350
0.1-0.2	955
0.2-0.3	1474
0.3-0.4	2603
0.4-0.5	1967
0.5-0.6	1188
0.6-0.7	412
0.7-0.8	126
0.8-0.85	46
0.85-0.9	24
0.9-0.95	4
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9627	High Similarity	NPD1510	Phase 2
0.9429	High Similarity	NPD4378	Clinical (unspecified phase)
0.9328	High Similarity	NPD1240	Approved
0.9236	High Similarity	NPD4380	Phase 2
0.9191	High Similarity	NPD1607	Approved
0.9155	High Similarity	NPD7410	Clinical (unspecified phase)
0.9137	High Similarity	NPD1549	Phase 2
0.913	High Similarity	NPD2796	Approved
0.9065	High Similarity	NPD1550	Clinical (unspecified phase)
0.9065	High Similarity	NPD1552	Clinical (unspecified phase)
0.8919	High Similarity	NPD2393	Clinical (unspecified phase)
0.8912	High Similarity	NPD7411	Suspended
0.8867	High Similarity	NPD7075	Discontinued
0.8859	High Similarity	NPD8443	Clinical (unspecified phase)
0.8792	High Similarity	NPD7096	Clinical (unspecified phase)
0.8792	High Similarity	NPD7819	Suspended
0.8725	High Similarity	NPD6801	Discontinued
0.8618	High Similarity	NPD4381	Clinical (unspecified phase)
0.86	High Similarity	NPD1934	Approved
0.8592	High Similarity	NPD2935	Discontinued
0.8562	High Similarity	NPD6799	Approved
0.8562	High Similarity	NPD1511	Approved
0.8553	High Similarity	NPD7768	Phase 2
0.8543	High Similarity	NPD2801	Approved
0.8542	High Similarity	NPD7421	Clinical (unspecified phase)
0.8526	High Similarity	NPD7852	Clinical (unspecified phase)
0.8511	High Similarity	NPD6651	Approved
0.8483	Intermediate Similarity	NPD3750	Approved
0.8483	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.8472	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8446	Intermediate Similarity	NPD1512	Approved
0.8431	Intermediate Similarity	NPD3882	Suspended
0.8365	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8344	Intermediate Similarity	NPD6599	Discontinued
0.8333	Intermediate Similarity	NPD1551	Phase 2
0.8333	Intermediate Similarity	NPD6959	Discontinued
0.8288	Intermediate Similarity	NPD1243	Approved
0.8288	Intermediate Similarity	NPD2800	Approved
0.828	Intermediate Similarity	NPD6232	Discontinued
0.8267	Intermediate Similarity	NPD920	Approved
0.8264	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.8255	Intermediate Similarity	NPD2533	Approved
0.8255	Intermediate Similarity	NPD2534	Approved
0.8255	Intermediate Similarity	NPD2532	Approved
0.8247	Intermediate Similarity	NPD3817	Phase 2
0.8243	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.8239	Intermediate Similarity	NPD7473	Discontinued
0.8227	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8201	Intermediate Similarity	NPD2798	Approved
0.8187	Intermediate Similarity	NPD3818	Discontinued
0.8176	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8176	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8176	Intermediate Similarity	NPD6166	Phase 2
0.816	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.8153	Intermediate Similarity	NPD5494	Approved
0.8148	Intermediate Similarity	NPD5953	Discontinued
0.8146	Intermediate Similarity	NPD5403	Approved
0.8141	Intermediate Similarity	NPD3749	Approved
0.8138	Intermediate Similarity	NPD3748	Approved
0.8138	Intermediate Similarity	NPD2799	Discontinued
0.8133	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.8112	Intermediate Similarity	NPD943	Approved
0.8099	Intermediate Similarity	NPD2313	Discontinued
0.8027	Intermediate Similarity	NPD2344	Approved
0.8025	Intermediate Similarity	NPD7286	Phase 2
0.8025	Intermediate Similarity	NPD7054	Approved
0.8013	Intermediate Similarity	NPD5401	Approved
0.7988	Intermediate Similarity	NPD6559	Discontinued
0.7975	Intermediate Similarity	NPD7472	Approved
0.7975	Intermediate Similarity	NPD7074	Phase 3
0.7972	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7962	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7947	Intermediate Similarity	NPD7390	Discontinued
0.7927	Intermediate Similarity	NPD6797	Phase 2
0.7898	Intermediate Similarity	NPD5402	Approved
0.7879	Intermediate Similarity	NPD7251	Discontinued
0.7872	Intermediate Similarity	NPD1203	Approved
0.7867	Intermediate Similarity	NPD4628	Phase 3
0.7862	Intermediate Similarity	NPD919	Approved
0.7842	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7832	Intermediate Similarity	NPD6832	Phase 2
0.7832	Intermediate Similarity	NPD4908	Phase 1
0.7831	Intermediate Similarity	NPD7808	Phase 3
0.7815	Intermediate Similarity	NPD2309	Approved
0.781	Intermediate Similarity	NPD1548	Phase 1
0.7806	Intermediate Similarity	NPD7458	Discontinued
0.7806	Intermediate Similarity	NPD3226	Approved
0.7805	Intermediate Similarity	NPD5844	Phase 1
0.78	Intermediate Similarity	NPD2654	Approved
0.7792	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7786	Intermediate Similarity	NPD3972	Approved
0.777	Intermediate Similarity	NPD7033	Discontinued
0.7764	Intermediate Similarity	NPD1247	Approved
0.7725	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7724	Intermediate Similarity	NPD3268	Approved
0.7718	Intermediate Similarity	NPD6099	Approved
0.7718	Intermediate Similarity	NPD6100	Approved
0.7714	Intermediate Similarity	NPD1610	Phase 2
0.7688	Intermediate Similarity	NPD4363	Phase 3
0.7688	Intermediate Similarity	NPD4360	Phase 2
0.7681	Intermediate Similarity	NPD9545	Approved
0.7667	Intermediate Similarity	NPD2346	Discontinued
0.7664	Intermediate Similarity	NPD9493	Approved
0.766	Intermediate Similarity	NPD9717	Approved
0.7651	Intermediate Similarity	NPD4308	Phase 3
0.7644	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7644	Intermediate Similarity	NPD4361	Phase 2
0.7632	Intermediate Similarity	NPD7003	Approved
0.7632	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7622	Intermediate Similarity	NPD1164	Approved
0.7622	Intermediate Similarity	NPD2797	Approved
0.7622	Intermediate Similarity	NPD1470	Approved
0.7607	Intermediate Similarity	NPD5710	Approved
0.7607	Intermediate Similarity	NPD5711	Approved
0.76	Intermediate Similarity	NPD5404	Approved
0.76	Intermediate Similarity	NPD5408	Approved
0.76	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD5406	Approved
0.76	Intermediate Similarity	NPD5405	Approved
0.7589	Intermediate Similarity	NPD422	Phase 1
0.7589	Intermediate Similarity	NPD1201	Approved
0.7568	Intermediate Similarity	NPD5124	Phase 1
0.7568	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7568	Intermediate Similarity	NPD230	Phase 1
0.7561	Intermediate Similarity	NPD3926	Phase 2
0.7545	Intermediate Similarity	NPD1729	Discontinued
0.75	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD3764	Approved
0.7471	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7453	Intermediate Similarity	NPD4288	Approved
0.745	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7431	Intermediate Similarity	NPD1876	Approved
0.7431	Intermediate Similarity	NPD3225	Approved
0.7417	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7415	Intermediate Similarity	NPD3027	Phase 3
0.7415	Intermediate Similarity	NPD4625	Phase 3
0.7391	Intermediate Similarity	NPD1465	Phase 2
0.7383	Intermediate Similarity	NPD4307	Phase 2
0.7379	Intermediate Similarity	NPD3267	Approved
0.7379	Intermediate Similarity	NPD3266	Approved
0.7376	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7375	Intermediate Similarity	NPD5890	Approved
0.7375	Intermediate Similarity	NPD5889	Approved
0.7374	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7372	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD1933	Approved
0.7325	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7322	Intermediate Similarity	NPD7584	Approved
0.732	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7319	Intermediate Similarity	NPD1241	Discontinued
0.7292	Intermediate Similarity	NPD1608	Approved
0.7289	Intermediate Similarity	NPD7229	Phase 3
0.7279	Intermediate Similarity	NPD9494	Approved
0.7267	Intermediate Similarity	NPD1613	Approved
0.7267	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7257	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7254	Intermediate Similarity	NPD1651	Approved
0.7251	Intermediate Similarity	NPD6104	Discontinued
0.7248	Intermediate Similarity	NPD6798	Discontinued
0.7248	Intermediate Similarity	NPD411	Approved
0.7248	Intermediate Similarity	NPD1296	Phase 2
0.7244	Intermediate Similarity	NPD3295	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD2296	Approved
0.723	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD37	Approved
0.7222	Intermediate Similarity	NPD6844	Discontinued
0.7219	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD447	Suspended
0.7211	Intermediate Similarity	NPD1019	Discontinued
0.7208	Intermediate Similarity	NPD1471	Phase 3
0.7205	Intermediate Similarity	NPD6585	Discontinued
0.7202	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7192	Intermediate Similarity	NPD1283	Approved
0.7182	Intermediate Similarity	NPD6776	Approved
0.7182	Intermediate Similarity	NPD6778	Approved
0.7182	Intermediate Similarity	NPD6777	Approved
0.7182	Intermediate Similarity	NPD6780	Approved
0.7182	Intermediate Similarity	NPD6782	Approved
0.7182	Intermediate Similarity	NPD6781	Approved
0.7182	Intermediate Similarity	NPD6779	Approved
0.7168	Intermediate Similarity	NPD8313	Approved
0.7168	Intermediate Similarity	NPD8312	Approved
0.7162	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7159	Intermediate Similarity	NPD4287	Approved
0.7143	Intermediate Similarity	NPD4477	Approved
0.7143	Intermediate Similarity	NPD4476	Approved
0.7133	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD7199	Phase 2
0.7123	Intermediate Similarity	NPD4749	Approved
0.7123	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7118	Intermediate Similarity	NPD7177	Discontinued
0.7118	Intermediate Similarity	NPD3751	Discontinued
0.7117	Intermediate Similarity	NPD6280	Approved
0.7117	Intermediate Similarity	NPD6279	Approved
0.7108	Intermediate Similarity	NPD6234	Discontinued
0.7107	Intermediate Similarity	NPD4662	Approved
0.7107	Intermediate Similarity	NPD7422	Clinical (unspecified phase)

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data