NPASS Compound

Structure

CID278556 OpenBabel06191716082D 21 23 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 -0.8660 -3.5000 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 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 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 -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 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -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 -1.7321 -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 -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 -1.7321 -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 19 1 0 0 0 0 2 20 1 0 0 0 0 3 4 2 0 0 0 0 3 5 1 0 0 0 0 4 6 1 0 0 0 0 5 7 2 0 0 0 0 6 11 2 0 0 0 0 7 11 1 0 0 0 0 8 12 2 0 0 0 0 8 15 1 0 0 0 0 9 12 1 0 0 0 0 9 16 2 0 0 0 0 10 13 1 0 0 0 0 10 14 2 0 0 0 0 11 14 1 0 0 0 0 12 19 1 0 0 0 0 13 17 1 0 0 0 0 13 18 2 0 0 0 0 14 21 1 0 0 0 0 15 17 2 0 0 0 0 15 20 1 0 0 0 0 16 17 1 0 0 0 0 16 21 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	282.09
Volume:	290.988
LogP:	3.856
LogD:	3.148
LogS:	-5.345
# Rotatable Bonds:	3
TPSA:	48.67
# H-Bond Aceptor:	4
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.738
Synthetic Accessibility Score:	1.963
Fsp3:	0.118
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.719
MDCK Permeability:	2.6374431399744935e-05
Pgp-inhibitor:	0.998
Pgp-substrate:	0.008
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.009
30% Bioavailability (F30%):	0.988

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.1
Plasma Protein Binding (PPB):	90.72288513183594%
Volume Distribution (VD):	0.827
Pgp-substrate:	6.410961627960205%

ADMET: Metabolism

CYP1A2-inhibitor:	0.979
CYP1A2-substrate:	0.956
CYP2C19-inhibitor:	0.948
CYP2C19-substrate:	0.212
CYP2C9-inhibitor:	0.851
CYP2C9-substrate:	0.923
CYP2D6-inhibitor:	0.517
CYP2D6-substrate:	0.921
CYP3A4-inhibitor:	0.763
CYP3A4-substrate:	0.237

ADMET: Excretion

Clearance (CL):	5.028
Half-life (T1/2):	0.317

ADMET: Toxicity

hERG Blockers:	0.106
Human Hepatotoxicity (H-HT):	0.129
Drug-inuced Liver Injury (DILI):	0.855
AMES Toxicity:	0.709
Rat Oral Acute Toxicity:	0.069
Maximum Recommended Daily Dose:	0.52
Skin Sensitization:	0.621
Carcinogencity:	0.249
Eye Corrosion:	0.009
Eye Irritation:	0.915
Respiratory Toxicity:	0.59

Download Data

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

Natural Product: NPC278556

Natural Product ID:	NPC278556
*Common Name:**	Chrysin Dimethyl Ether
IUPAC Name:	5,7-dimethoxy-2-phenylchromen-4-one
Synonyms:	5,7-Dimethoxyflavone; Chrysin-Dimethylether
Standard InCHIKey:	JRFZSUMZAUHNSL-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C17H14O4/c1-19-12-8-15(20-2)17-13(18)10-14(21-16(17)9-12)11-6-4-3-5-7-11/h3-10H,1-2H3
SMILES:	COc1cc(c2c(=O)cc(c3ccccc3)oc2c1)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL275391
PubChem CID:	88881
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
NPO23105	Boesenbergia rotunda	Species	Zingiberaceae	Eukaryota	n.a.	rhizome	n.a.	DOI[10.1016/0031-9422(83)83075-1]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/0031-9422(90)85349-K]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	root	n.a.	DOI[10.1186/1471-2202-6-1]
NPO1373	Pulsatilla chinensis	Species	Ranunculaceae	Eukaryota	n.a.	root	n.a.	PMID[10514313]
NPO1373	Pulsatilla chinensis	Species	Ranunculaceae	Eukaryota	roots	n.a.	n.a.	PMID[10514313]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10579865]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	leaf	n.a.	PMID[10716597]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10757718]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11374948]
NPO27986	Lonchocarpus chiricanus	Species	Fabaceae	Eukaryota	Root barks	n.a.	n.a.	PMID[11421729]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11561442]
NPO1373	Pulsatilla chinensis	Species	Ranunculaceae	Eukaryota	roots	n.a.	n.a.	PMID[11575962]
NPO17333	Valeriana officinalis	Species	Caprifoliaceae	Eukaryota	roots	n.a.	n.a.	PMID[12398547]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12579877]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	root	n.a.	PMID[1375626]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1375626]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1602302]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	root	n.a.	PMID[1602302]
NPO27695	Centaurea sonchifolia	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[1624943]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	root	n.a.	PMID[16864458]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	roots	n.a.	n.a.	PMID[16989518]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	root	n.a.	PMID[17250858]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17265278]
NPO27600	Boesenbergia pandurata	Species	Zingiberaceae	Eukaryota	rhizomes	Pindaya Township, Shan State, Myanmar	2004-NOV	PMID[17896818]
NPO17333	Valeriana officinalis	Species	Caprifoliaceae	Eukaryota	n.a.	root	n.a.	PMID[18164718]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	leaf	n.a.	PMID[1823717]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	root	n.a.	PMID[1823717]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18554602]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	bark	n.a.	PMID[18996177]
NPO17186	Sibiraea angustata	Species	Rosaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[19252323]
NPO17333	Valeriana officinalis	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20853876]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	root	n.a.	n.a.	PMID[21486005]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	root	n.a.	PMID[21486005]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21514608]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	dried roots	purchased from Sichuan Neautus Traditional Chinese Medicine Co. Ltd. (Chengdu, P.R. China)	n.a.	PMID[22148431]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	leaves	n.a.	n.a.	PMID[23268606]
NPO19747	Maytenus emarginata	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[2380715]
NPO19747	Maytenus emarginata	Species	Celastraceae	Eukaryota	n.a.	stem	n.a.	PMID[2380715]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23852638]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24549173]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24963543]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25237706]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	bark	n.a.	PMID[2534610]
NPO20278	Scutellaria indica	Species	Lamiaceae	Eukaryota	whole plant	n.a.	n.a.	PMID[25637363]
NPO27600	Boesenbergia pandurata	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27508308]
NPO27600	Boesenbergia pandurata	Species	Zingiberaceae	Eukaryota	Rhizomes	n.a.	n.a.	PMID[28099006]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	root	n.a.	PMID[2816380]
NPO17333	Valeriana officinalis	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28485933]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	Leaves	n.a.	n.a.	PMID[29355322]
NPO1534	Jatropha gossypiifolia	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[30106289]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	Leaves	n.a.	n.a.	PMID[31556299]
NPO19745	Esox lucius	Species	Esocidae	Eukaryota	n.a.	n.a.	n.a.	PMID[3349210]
NPO17333	Valeriana officinalis	Species	Caprifoliaceae	Eukaryota	n.a.	root	n.a.	PMID[547813]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7102323]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7304185]
NPO19747	Maytenus emarginata	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8176403]
NPO28159	Rubia akane	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8176404]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8699928]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8722541]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[Article]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	root	n.a.	Database[Article]
NPO19745	Esox lucius	Species	Esocidae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO19745	Esox lucius	Species	Esocidae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO21600	Aconitum variegatum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18131	Micromelum falcatum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO16481	Xanthium canadense	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18492	Prunus pseudocerasus	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14941	Delphinium tricorne	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1373	Pulsatilla chinensis	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO20278	Scutellaria indica	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19614	Erica cinerea	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22500	Stephania dielsiana	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17333	Valeriana officinalis	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19614	Erica cinerea	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16481	Xanthium canadense	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14595	Lactarius torminosus	Species	Russulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1534	Jatropha gossypiifolia	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1373	Pulsatilla chinensis	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27397	Drymaria cordata	Species	Caryophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18492	Prunus pseudocerasus	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21600	Aconitum variegatum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18131	Micromelum falcatum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20278	Scutellaria indica	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14941	Delphinium tricorne	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27882	Boswellia ovalifoliolata	Species	Burseraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23156	Maclura cochinchinensis	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17333	Valeriana officinalis	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22500	Stephania dielsiana	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20278	Scutellaria indica	Species	Lamiaceae	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]
NPO17333	Valeriana officinalis	Species	Caprifoliaceae	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]
NPO18492	Prunus pseudocerasus	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO1373	Pulsatilla chinensis	Species	Ranunculaceae	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]
NPO18492	Prunus pseudocerasus	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17050	Haemanthus albiflos	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14595	Lactarius torminosus	Species	Russulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18899	Keyserlingia koreensis	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO18653	Cyathus intermedius	Species	Nidulariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8961	Bethencourtia palmensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20278	Scutellaria indica	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19614	Erica cinerea	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28289	Nepytia freemani	Species	Geometridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28159	Rubia akane	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27455	Dysidea fragilis	Species	Dysideidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17186	Sibiraea angustata	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26342	Dialium excelsum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27397	Drymaria cordata	Species	Caryophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15370	Tamarix dioica	Species	Tamaricaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16034	Lecanora sulphurata	Species	Lecanoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6570	Cinnamomum philippinense	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9142	Aeschynanthus parvifolius	Species	Gesneriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27702	Matricaria sabulosa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10957	Cladosiphon okamuranus	Species	Chordariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7328	Salvia miniata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17433	Peltophorum dubium	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17987	Mycosphaerella nawae	Species	Mycosphaerellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19383	Lactarius mitissimus	Species	Russulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2351	Echinocardium cordatum	Species	Loveniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27338	Senecio platyphylloides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27986	Lonchocarpus chiricanus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27234	Thalassiosira weissflogii	Species	Thalassiosiraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27506	Orgyia pseudotsugata	Species	Lymantriidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14941	Delphinium tricorne	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28426	Etmopterus spinax	Species	Etmopteridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19416	Streptomyces sakaiensis	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO18986	Betula papyrifera	Species	Betulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27916	Hardenbergia violacea	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11763	Cyperus capitatus	Species	Cyperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22500	Stephania dielsiana	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19069	Thelepus setosus	Species	Terebellidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9354	Lepechinia urbanii	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28412	Amorphophallus konjac	Species	Araceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2030	Mimosa pigra	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17333	Valeriana officinalis	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26476	Preussia terricola	Species	Sporormiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26553	Lemonia spectabilis	Species	Lemoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18824	Alpinia pulcherrima	Species	Staphylinidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18747	Bufo bankorensis	Species	Bufonidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19285	Chromodoris cavae	Species	Chromodorididae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19495	Bignonia unguiscati	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15709	Lobelia langeana	Species	Campanulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21344	Fadogia agrestis	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1184	Colchicum filifolium	Species	Colchicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16298	Quercus marilandica	Species	Fagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13245	Agelas longissima	Species	Agelasidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25499	Campanula choziatowskyi	Species	Campanulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27816	Pterocaulon serrulatum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28063	Beilschmiedia madang	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16256	Helleborus viridis	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17565	Hordeum bulbosum	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25835	Parmotrema nilgherrense	Species	Parmeliaceae	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]
NPO28044	Erythrina hypaphorus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17337	Centaurea scoparia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27882	Boswellia ovalifoliolata	Species	Burseraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27642	Podocarpus dacrydioides	Species	Podocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18131	Micromelum falcatum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16727	Iris sibirica	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28313	Mentzelia decapetala	Species	Loasaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27613	Helleborus macranthus	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4171	Isolona pilosa	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25549	Rhizophagus intraradices	Species	Glomeraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27614	Salix rosmarinifolia	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19745	Esox lucius	Species	Esocidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16481	Xanthium canadense	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12464	Litsea nitida	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16156	Mucuna holtonii	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19683	Pycnothymus rigidus	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO1560	Boronia alata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26321	Salvia patens	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23105	Boesenbergia rotunda	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19554	Coronilla hyrcana	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27057	Matsucoccus josephi	Species	Margarodidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1373	Pulsatilla chinensis	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4164	Salvia virgata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28206	Aniba santalodora	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17876	Magnolia henryi	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6642	Mocis latipes	Species	0ctuidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27145	Euphorbia hylonoma	Species	Euphorbiaceae	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]
NPO5970.1	Petunia axillaris subsp. parodii	Subspecies	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28083	Salvia lavanduloides	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19350	Ephedra altissima	Species	Ephedraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1457	Phoma asparagi	Species	Didymellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18326	Eria siamensis	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20584	Cheilanthes fragrans	Species	Pteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27600	Boesenbergia pandurata	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21600	Aconitum variegatum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18576	Vernonia aurea	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23156	Maclura cochinchinensis	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27637	Heliotropium scabrum	Species	Heliotropiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28003	Astragalus circassicus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19747	Maytenus emarginata	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21534	Ostrya carpinifolia	Species	Betulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28385	Iris kashmiriana	Species	Tarachodidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11849	Cynoglossum macrostylum	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20618	Penicilliopsis clavariiformis	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1534	Jatropha gossypiifolia	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19222	Mycale tenuis	Species	Mycalidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

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

NP Quantity Composition/Concentration

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

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

Biological Activity

Activity Type	# Activity
IC50	13
MIC	1
Others	42
Potency	24

Activity Type	# Activity
Cell Line	12
Individual Protein	21
Organism	21
Others	10
PROTEIN COMPLEX	2
Protein-Protein Interaction	1
Tissue	12
Uncleic Acid	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT515	Cell Line	SGC-7901	Homo sapiens	IC50	=	3700.0	nM	PMID[527299]
NPT139	Cell Line	HT-29	Homo sapiens	IC50	=	2000.0	nM	PMID[527299]
NPT48	Individual Protein	Lysine-specific demethylase 4D-like	Homo sapiens	Potency	=	25118.9	nM	PMID[527304]
NPT537	Individual Protein	Ras-related protein Rab-9A	Homo sapiens	Potency	=	1778.3	nM	PMID[527304]
NPT538	Individual Protein	Niemann-Pick C1 protein	Homo sapiens	Potency	=	2238.7	nM	PMID[527304]
NPT1422	Individual Protein	ATP-binding cassette sub-family G member 2	Homo sapiens	IC50	=	9200.0	nM	PMID[527305]
NPT1422	Individual Protein	ATP-binding cassette sub-family G member 2	Homo sapiens	IC50	=	11000.0	nM	PMID[527305]
NPT64	Individual Protein	ATPase family AAA domain-containing protein 5	Homo sapiens	Potency	n.a.	23099.9	nM	PMID[527304]
NPT64	Individual Protein	ATPase family AAA domain-containing protein 5	Homo sapiens	Potency	n.a.	16353.5	nM	PMID[527304]
NPT520	Cell Line	3T3-L1	Mus musculus	Activity	=	6.3	%	PMID[527306]
NPT520	Cell Line	3T3-L1	Mus musculus	Activity	=	3.4	%	PMID[527306]
NPT520	Cell Line	3T3-L1	Mus musculus	Activity	=	7.5	%	PMID[527306]
NPT520	Cell Line	3T3-L1	Mus musculus	Activity	=	-88.1	%	PMID[527306]
NPT65	Cell Line	HepG2	Homo sapiens	Potency	n.a.	12589.3	nM	PMID[527304]
NPT199	Individual Protein	DNA polymerase kappa	Homo sapiens	Potency	n.a.	89125.1	nM	PMID[527304]
NPT484	Individual Protein	Luciferin 4-monooxygenase	Photinus pyralis	Potency	n.a.	5358.2	nM	PMID[527304]
NPT101	Individual Protein	Glucagon-like peptide 1 receptor	Homo sapiens	Potency	n.a.	8912.5	nM	PMID[527304]
NPT157	Individual Protein	Breast cancer type 1 susceptibility protein	Homo sapiens	Potency	n.a.	7943.3	nM	PMID[527304]
NPT50	Individual Protein	Tyrosyl-DNA phosphodiesterase 1	Homo sapiens	Potency	n.a.	29092.9	nM	PMID[527304]
NPT50	Individual Protein	Tyrosyl-DNA phosphodiesterase 1	Homo sapiens	Potency	n.a.	20596.2	nM	PMID[527304]
NPT585	Individual Protein	Nuclear receptor subfamily 0 group B member 1	Homo sapiens	IC50	>	67615.0	nM	PMID[527304]
NPT160	Individual Protein	TAR DNA-binding protein 43	Homo sapiens	Potency	n.a.	35481.3	nM	PMID[527304]
NPT535	Individual Protein	Parathyroid hormone receptor	Homo sapiens	Potency	n.a.	56234.1	nM	PMID[527304]
NPT1443	Individual Protein	Pyruvate dehydrogenase kinase isoform 1	Homo sapiens	Inhibition	=	5.8	%	PMID[527310]
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	65590.0	nM	PMID[527311]
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	33170.0	nM	PMID[527311]
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	7430.0	nM	PMID[527311]
NPT113	Cell Line	RAW264.7	Mus musculus	Activity	=	133.51	%	PMID[527311]
NPT113	Cell Line	RAW264.7	Mus musculus	Inhibition	=	31.48	%	PMID[527311]
NPT32	Organism	Mus musculus	Mus musculus	Blood glucose	=	444.4	mg dl-1	PMID[527300]
NPT32	Organism	Mus musculus	Mus musculus	Blood glucose	=	399.5	mg dl-1	PMID[527300]
NPT2	Others	Unspecified		Ratio	=	89.9	n.a.	PMID[527300]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	25.0	ug.mL-1	PMID[527301]
NPT536	Uncleic Acid	microRNA 21	Homo sapiens	Potency	=	6561.4	nM	PMID[527304]
NPT94	Individual Protein	Aldehyde dehydrogenase 1A1	Homo sapiens	Potency	=	28183.8	nM	PMID[527304]
NPT197	Protein-Protein Interaction	Menin/Histone-lysine N-methyltransferase MLL	Homo sapiens	Potency	=	22387.2	nM	PMID[527304]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Potency	n.a.	3294.4	nM	PMID[527304]
NPT8	Individual Protein	DNA polymerase iota	Homo sapiens	Potency	n.a.	79432.8	nM	PMID[527304]
NPT2	Others	Unspecified		Potency	n.a.	10000.0	nM	PMID[527304]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Potency	n.a.	3696.4	nM	PMID[527304]
NPT2	Others	Unspecified		Potency	n.a.	35481.3	nM	PMID[527304]
NPT35	Others	n.a.		IC50	>	67615.0	nM	PMID[527304]
NPT22906	PROTEIN COMPLEX	Urease subunit alpha/Urease subunit beta	Helicobacter pylori (strain ATCC 700392 / 26695) (Campylobacterpylori)	IC50	=	2185000.0	nM	PMID[527307]
NPT72	Individual Protein	Solute carrier organic anion transporter family member 1B3	Homo sapiens	Inhibition	=	103.09	%	PMID[527308]
NPT73	Individual Protein	Solute carrier organic anion transporter family member 1B1	Homo sapiens	Inhibition	=	112.12	%	PMID[527308]
NPT27	Others	Unspecified		Drug excretion	=	3.1	%	PMID[527309]
NPT27	Others	Unspecified		Drug excretion	=	0.96	%	PMID[527309]
NPT27	Others	Unspecified		Tmax	=	2.86	hr	PMID[527309]
NPT632	Tissue	Brain	Rattus norvegicus	Tmax	=	3.14	hr	PMID[527309]
NPT21823	TISSUE	Lung	Rattus norvegicus	Tmax	=	1.2	hr	PMID[527309]
NPT1590	Tissue	Kidney	Rattus norvegicus	Tmax	=	3.43	hr	PMID[527309]
NPT1593	Tissue	Liver	Rattus norvegicus	Tmax	=	2.57	hr	PMID[527309]
NPT27	Others	Unspecified		Cmax	=	0.91	ug/g	PMID[527309]
NPT632	Tissue	Brain	Rattus norvegicus	Cmax	=	0.96	ug/g	PMID[527309]
NPT21823	TISSUE	Lung	Rattus norvegicus	Cmax	=	2.0	ug/g	PMID[527309]
NPT1590	Tissue	Kidney	Rattus norvegicus	Cmax	=	1.33	ug/g	PMID[527309]
NPT1593	Tissue	Liver	Rattus norvegicus	Cmax	=	3.85	ug/g	PMID[527309]
NPT27	Others	Unspecified		AUC	=	1.9	ug.hr/g	PMID[527309]
NPT632	Tissue	Brain	Rattus norvegicus	AUC	=	1.91	ug.hr/g	PMID[527309]
NPT21823	TISSUE	Lung	Rattus norvegicus	AUC	=	2.17	ug.hr/g	PMID[527309]
NPT1590	Tissue	Kidney	Rattus norvegicus	AUC	=	2.51	ug.hr/g	PMID[527309]
NPT1593	Tissue	Liver	Rattus norvegicus	AUC	=	8.6	ug.hr/g	PMID[527309]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	F	=	2.1	%	PMID[527309]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	ka	=	8.69	/hr	PMID[527309]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Vd	=	2957.53	ml	PMID[527309]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Cmax	=	0.78	ug.mL-1	PMID[527309]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Tmax	=	0.76	hr	PMID[527309]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	CL	=	7.98	ml/hr	PMID[527309]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	CL	=	367.28	ml/hr	PMID[527309]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Ke	=	0.32	/hr	PMID[527309]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Ke	=	0.13	/hr	PMID[527309]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	T1/2	=	3.75	hr	PMID[527309]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	T1/2	=	5.85	hr	PMID[527309]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	AUC	=	233480.0	ng.hr.mL-1	PMID[527309]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	AUC	=	7010.0	ng.hr.mL-1	PMID[527309]
NPT2	Others	Unspecified		Potency	n.a.	2818.4	nM	PMID[527304]
NPT471	Organism	Trypanosoma brucei brucei	Trypanosoma brucei brucei	IC50	<	30000.0	nM	PMID[527312]
NPT20555	ORGANISM	SARS-CoV-2	Severe acute respiratory syndrome coronavirus 2	IC50	>	20000.0	nM	PMID[527313]
NPT20555	ORGANISM	SARS-CoV-2	Severe acute respiratory syndrome coronavirus 2	IC50	>	19952.62	nM	PMID[527313]

☑ 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 NPC278556 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	517
0.1-0.2	1990
0.2-0.3	5535
0.3-0.4	12404
0.4-0.5	4643
0.5-0.6	4982
0.6-0.7	5904
0.7-0.8	3909
0.8-0.85	1758
0.85-0.9	873
0.9-0.95	156
0.95-1	26

Similarity Score	Similarity Level	Natural Product ID
0.9921	High Similarity	NPC473655
0.9921	High Similarity	NPC101294
0.9841	High Similarity	NPC284424
0.9688	High Similarity	NPC292998
0.9615	High Similarity	NPC231772
0.9615	High Similarity	NPC234133
0.9615	High Similarity	NPC161196
0.9615	High Similarity	NPC127447
0.9615	High Similarity	NPC72452
0.9615	High Similarity	NPC124784
0.9615	High Similarity	NPC473887
0.9615	High Similarity	NPC254741
0.9615	High Similarity	NPC47815
0.9615	High Similarity	NPC61546
0.9615	High Similarity	NPC194281
0.9615	High Similarity	NPC29353
0.9612	High Similarity	NPC125269
0.96	High Similarity	NPC475496
0.96	High Similarity	NPC49852
0.96	High Similarity	NPC41721
0.9542	High Similarity	NPC266597
0.9542	High Similarity	NPC250266
0.9538	High Similarity	NPC99854
0.9524	High Similarity	NPC473907
0.947	High Similarity	NPC17848
0.947	High Similarity	NPC276905
0.9466	High Similarity	NPC13408
0.9457	High Similarity	NPC182428
0.9449	High Similarity	NPC211120
0.9449	High Similarity	NPC473894
0.9398	High Similarity	NPC136095
0.9398	High Similarity	NPC78913
0.9398	High Similarity	NPC18260
0.9398	High Similarity	NPC241838
0.9398	High Similarity	NPC152042
0.9398	High Similarity	NPC143799
0.9394	High Similarity	NPC103001
0.9394	High Similarity	NPC259685
0.9389	High Similarity	NPC46869
0.9385	High Similarity	NPC223354
0.9385	High Similarity	NPC213216
0.9385	High Similarity	NPC78540
0.9385	High Similarity	NPC50898
0.9385	High Similarity	NPC274121
0.9328	High Similarity	NPC159275
0.9328	High Similarity	NPC269652
0.9328	High Similarity	NPC241100
0.9328	High Similarity	NPC230285
0.9328	High Similarity	NPC184536
0.9328	High Similarity	NPC281207
0.9328	High Similarity	NPC103342
0.9328	High Similarity	NPC103904
0.9328	High Similarity	NPC146679
0.9328	High Similarity	NPC150522
0.9328	High Similarity	NPC59951
0.9323	High Similarity	NPC280284
0.9323	High Similarity	NPC99333
0.9323	High Similarity	NPC188947
0.9323	High Similarity	NPC201395
0.9313	High Similarity	NPC172262
0.9313	High Similarity	NPC66705
0.9286	High Similarity	NPC2771
0.9259	High Similarity	NPC282300
0.9259	High Similarity	NPC103362
0.9259	High Similarity	NPC136840
0.9259	High Similarity	NPC110969
0.9259	High Similarity	NPC90582
0.9259	High Similarity	NPC262094
0.9254	High Similarity	NPC53181
0.9254	High Similarity	NPC96565
0.9254	High Similarity	NPC217186
0.9254	High Similarity	NPC20709
0.9254	High Similarity	NPC216978
0.9254	High Similarity	NPC310135
0.9254	High Similarity	NPC11566
0.9254	High Similarity	NPC329203
0.9254	High Similarity	NPC55018
0.9254	High Similarity	NPC150648
0.9254	High Similarity	NPC265871
0.9254	High Similarity	NPC225153
0.9254	High Similarity	NPC274784
0.9254	High Similarity	NPC301217
0.9254	High Similarity	NPC303633
0.9254	High Similarity	NPC222342
0.9254	High Similarity	NPC220062
0.9248	High Similarity	NPC157855
0.9248	High Similarity	NPC290291
0.9248	High Similarity	NPC188879
0.9248	High Similarity	NPC228661
0.9248	High Similarity	NPC275055
0.9237	High Similarity	NPC57601
0.9231	High Similarity	NPC475589
0.9231	High Similarity	NPC113006
0.9231	High Similarity	NPC31872
0.9231	High Similarity	NPC473584
0.9225	High Similarity	NPC228184
0.9219	High Similarity	NPC475017
0.9191	High Similarity	NPC226636
0.9191	High Similarity	NPC11561
0.9191	High Similarity	NPC70853
0.9191	High Similarity	NPC9966
0.9185	High Similarity	NPC474037
0.9185	High Similarity	NPC472409
0.9185	High Similarity	NPC6407
0.9185	High Similarity	NPC129853
0.9185	High Similarity	NPC110228
0.9185	High Similarity	NPC76445
0.9185	High Similarity	NPC284550
0.9185	High Similarity	NPC171094
0.9185	High Similarity	NPC188243
0.9185	High Similarity	NPC172986
0.9185	High Similarity	NPC261227
0.9185	High Similarity	NPC270883
0.9179	High Similarity	NPC118813
0.9179	High Similarity	NPC124269
0.9173	High Similarity	NPC256042
0.9173	High Similarity	NPC116775
0.9173	High Similarity	NPC281917
0.9173	High Similarity	NPC187432
0.9173	High Similarity	NPC240593
0.9173	High Similarity	NPC216361
0.916	High Similarity	NPC25937
0.916	High Similarity	NPC205468
0.916	High Similarity	NPC229646
0.916	High Similarity	NPC212631
0.916	High Similarity	NPC129132
0.916	High Similarity	NPC10971
0.916	High Similarity	NPC257756
0.916	High Similarity	NPC87231
0.9154	High Similarity	NPC137264
0.9154	High Similarity	NPC5515
0.9154	High Similarity	NPC270369
0.9134	High Similarity	NPC65041
0.9124	High Similarity	NPC113089
0.9124	High Similarity	NPC59522
0.9124	High Similarity	NPC470216
0.9118	High Similarity	NPC147688
0.9118	High Similarity	NPC156590
0.9118	High Similarity	NPC22467
0.9118	High Similarity	NPC4743
0.9118	High Similarity	NPC64908
0.9118	High Similarity	NPC118840
0.9118	High Similarity	NPC52576
0.9118	High Similarity	NPC3188
0.9118	High Similarity	NPC324386
0.9118	High Similarity	NPC213322
0.9118	High Similarity	NPC205006
0.9118	High Similarity	NPC312391
0.9118	High Similarity	NPC29536
0.9111	High Similarity	NPC140890
0.9111	High Similarity	NPC473209
0.9111	High Similarity	NPC261234
0.9104	High Similarity	NPC303644
0.9104	High Similarity	NPC296490
0.9104	High Similarity	NPC107586
0.9104	High Similarity	NPC243083
0.9104	High Similarity	NPC162680
0.9104	High Similarity	NPC32441
0.9104	High Similarity	NPC294409
0.9104	High Similarity	NPC181124
0.9104	High Similarity	NPC253616
0.9104	High Similarity	NPC79943
0.9104	High Similarity	NPC7013
0.9104	High Similarity	NPC13768
0.9104	High Similarity	NPC287246
0.9104	High Similarity	NPC116632
0.9104	High Similarity	NPC12296
0.9104	High Similarity	NPC299379
0.9104	High Similarity	NPC295261
0.9104	High Similarity	NPC209560
0.9098	High Similarity	NPC9985
0.9098	High Similarity	NPC239495
0.9091	High Similarity	NPC159623
0.9091	High Similarity	NPC144051
0.9091	High Similarity	NPC263670
0.9091	High Similarity	NPC28753
0.9091	High Similarity	NPC18877
0.9091	High Similarity	NPC175098
0.9091	High Similarity	NPC472365
0.9091	High Similarity	NPC223457
0.9091	High Similarity	NPC139813
0.9091	High Similarity	NPC82225
0.9091	High Similarity	NPC294593
0.9091	High Similarity	NPC188646
0.9091	High Similarity	NPC56031
0.9091	High Similarity	NPC204960
0.9091	High Similarity	NPC192304
0.9091	High Similarity	NPC242294
0.9091	High Similarity	NPC337373
0.9091	High Similarity	NPC20560
0.9091	High Similarity	NPC312318
0.9084	High Similarity	NPC64359
0.9084	High Similarity	NPC262359
0.9084	High Similarity	NPC308037
0.9077	High Similarity	NPC39753
0.9077	High Similarity	NPC115998
0.907	High Similarity	NPC125887
0.9058	High Similarity	NPC273538
0.9058	High Similarity	NPC179970
0.9058	High Similarity	NPC471590

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 NPC278556 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	472
0.1-0.2	998
0.2-0.3	1501
0.3-0.4	2743
0.4-0.5	1864
0.5-0.6	1079
0.6-0.7	335
0.7-0.8	97
0.8-0.85	41
0.85-0.9	18
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9466	High Similarity	NPD2796	Approved
0.9104	High Similarity	NPD1552	Clinical (unspecified phase)
0.9104	High Similarity	NPD1550	Clinical (unspecified phase)
0.9058	High Similarity	NPD4378	Clinical (unspecified phase)
0.9037	High Similarity	NPD1549	Phase 2
0.8955	High Similarity	NPD1510	Phase 2
0.8939	High Similarity	NPD1240	Approved
0.8849	High Similarity	NPD6799	Approved
0.8806	High Similarity	NPD1607	Approved
0.8786	High Similarity	NPD7410	Clinical (unspecified phase)
0.8714	High Similarity	NPD1511	Approved
0.8676	High Similarity	NPD3748	Approved
0.8592	High Similarity	NPD1512	Approved
0.8562	High Similarity	NPD2801	Approved
0.8561	High Similarity	NPD1243	Approved
0.8552	High Similarity	NPD7411	Suspended
0.8507	High Similarity	NPD6859	Clinical (unspecified phase)
0.8503	High Similarity	NPD3817	Phase 2
0.8493	Intermediate Similarity	NPD6801	Discontinued
0.8493	Intermediate Similarity	NPD1934	Approved
0.8483	Intermediate Similarity	NPD6599	Discontinued
0.8435	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8435	Intermediate Similarity	NPD7819	Suspended
0.8435	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8403	Intermediate Similarity	NPD920	Approved
0.8392	Intermediate Similarity	NPD5401	Approved
0.8385	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.838	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.8378	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8369	Intermediate Similarity	NPD3750	Approved
0.8358	Intermediate Similarity	NPD6832	Phase 2
0.8357	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8356	Intermediate Similarity	NPD4380	Phase 2
0.8276	Intermediate Similarity	NPD5403	Approved
0.8267	Intermediate Similarity	NPD7075	Discontinued
0.8267	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8264	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.8214	Intermediate Similarity	NPD1551	Phase 2
0.82	Intermediate Similarity	NPD3882	Suspended
0.8169	Intermediate Similarity	NPD2654	Approved
0.8169	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8158	Intermediate Similarity	NPD5494	Approved
0.8134	Intermediate Similarity	NPD3266	Approved
0.8134	Intermediate Similarity	NPD3267	Approved
0.8058	Intermediate Similarity	NPD1933	Approved
0.8042	Intermediate Similarity	NPD2800	Approved
0.8026	Intermediate Similarity	NPD3749	Approved
0.8	Intermediate Similarity	NPD1203	Approved
0.7986	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7974	Intermediate Similarity	NPD919	Approved
0.7971	Intermediate Similarity	NPD1296	Phase 2
0.7971	Intermediate Similarity	NPD2313	Discontinued
0.7969	Intermediate Similarity	NPD1241	Discontinued
0.7961	Intermediate Similarity	NPD7768	Phase 2
0.7949	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7949	Intermediate Similarity	NPD6166	Phase 2
0.7949	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7949	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7941	Intermediate Similarity	NPD2798	Approved
0.7939	Intermediate Similarity	NPD1548	Phase 1
0.7929	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7911	Intermediate Similarity	NPD7054	Approved
0.7911	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.791	Intermediate Similarity	NPD9717	Approved
0.791	Intermediate Similarity	NPD3972	Approved
0.7902	Intermediate Similarity	NPD2344	Approved
0.7895	Intermediate Similarity	NPD5402	Approved
0.7887	Intermediate Similarity	NPD2799	Discontinued
0.7885	Intermediate Similarity	NPD3926	Phase 2
0.7872	Intermediate Similarity	NPD6651	Approved
0.7871	Intermediate Similarity	NPD6959	Discontinued
0.7871	Intermediate Similarity	NPD1247	Approved
0.7862	Intermediate Similarity	NPD7472	Approved
0.7857	Intermediate Similarity	NPD4307	Phase 2
0.7848	Intermediate Similarity	NPD3818	Discontinued
0.7842	Intermediate Similarity	NPD3268	Approved
0.7836	Intermediate Similarity	NPD422	Phase 1
0.7812	Intermediate Similarity	NPD6797	Phase 2
0.781	Intermediate Similarity	NPD1019	Discontinued
0.7794	Intermediate Similarity	NPD3225	Approved
0.7785	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7764	Intermediate Similarity	NPD7251	Discontinued
0.7762	Intermediate Similarity	NPD7033	Discontinued
0.775	Intermediate Similarity	NPD7074	Phase 3
0.7737	Intermediate Similarity	NPD2797	Approved
0.7716	Intermediate Similarity	NPD7808	Phase 3
0.7716	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7708	Intermediate Similarity	NPD2935	Discontinued
0.7698	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7687	Intermediate Similarity	NPD17	Approved
0.7687	Intermediate Similarity	NPD2309	Approved
0.7639	Intermediate Similarity	NPD4308	Phase 3
0.7619	Intermediate Similarity	NPD4628	Phase 3
0.7613	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.761	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7607	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7606	Intermediate Similarity	NPD943	Approved
0.7595	Intermediate Similarity	NPD6232	Discontinued
0.7593	Intermediate Similarity	NPD5953	Discontinued
0.7586	Intermediate Similarity	NPD6100	Approved
0.7586	Intermediate Similarity	NPD6099	Approved
0.7578	Intermediate Similarity	NPD7286	Phase 2
0.7574	Intermediate Similarity	NPD1610	Phase 2
0.7571	Intermediate Similarity	NPD4908	Phase 1
0.7566	Intermediate Similarity	NPD3226	Approved
0.7562	Intermediate Similarity	NPD7473	Discontinued
0.7548	Intermediate Similarity	NPD4288	Approved
0.7536	Intermediate Similarity	NPD1876	Approved
0.7534	Intermediate Similarity	NPD2346	Discontinued
0.7534	Intermediate Similarity	NPD1471	Phase 3
0.7533	Intermediate Similarity	NPD2533	Approved
0.7533	Intermediate Similarity	NPD2534	Approved
0.7533	Intermediate Similarity	NPD2532	Approved
0.7518	Intermediate Similarity	NPD1608	Approved
0.7517	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD3142	Approved
0.7483	Intermediate Similarity	NPD3140	Approved
0.7468	Intermediate Similarity	NPD5889	Approved
0.7468	Intermediate Similarity	NPD5890	Approved
0.7465	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7439	Intermediate Similarity	NPD6559	Discontinued
0.7415	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.7415	Intermediate Similarity	NPD2353	Approved
0.7407	Intermediate Similarity	NPD9545	Approved
0.7403	Intermediate Similarity	NPD6585	Discontinued
0.7391	Intermediate Similarity	NPD2403	Approved
0.7388	Intermediate Similarity	NPD9493	Approved
0.7362	Intermediate Similarity	NPD5844	Phase 1
0.7348	Intermediate Similarity	NPD5535	Approved
0.7343	Intermediate Similarity	NPD411	Approved
0.7343	Intermediate Similarity	NPD6798	Discontinued
0.7333	Intermediate Similarity	NPD3887	Approved
0.731	Intermediate Similarity	NPD447	Suspended
0.731	Intermediate Similarity	NPD5124	Phase 1
0.731	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD6279	Approved
0.7308	Intermediate Similarity	NPD6280	Approved
0.7279	Intermediate Similarity	NPD1894	Discontinued
0.7267	Intermediate Similarity	NPD4360	Phase 2
0.7267	Intermediate Similarity	NPD4363	Phase 3
0.7267	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7261	Intermediate Similarity	NPD1465	Phase 2
0.7244	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7237	Intermediate Similarity	NPD7390	Discontinued
0.7229	Intermediate Similarity	NPD6104	Discontinued
0.7225	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD4361	Phase 2
0.7219	Intermediate Similarity	NPD2354	Approved
0.7203	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD1652	Phase 2
0.7197	Intermediate Similarity	NPD6844	Discontinued
0.7195	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7192	Intermediate Similarity	NPD230	Phase 1
0.719	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD4662	Approved
0.719	Intermediate Similarity	NPD4661	Approved
0.7184	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD6233	Phase 2
0.7169	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD6808	Phase 2
0.7143	Intermediate Similarity	NPD1481	Phase 2
0.7133	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD6971	Discontinued
0.7124	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7123	Intermediate Similarity	NPD1613	Approved
0.7123	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD1729	Discontinued
0.7107	Intermediate Similarity	NPD2296	Approved
0.7105	Intermediate Similarity	NPD3295	Clinical (unspecified phase)
0.7103	Intermediate Similarity	NPD3764	Approved
0.7101	Intermediate Similarity	NPD1651	Approved
0.7099	Intermediate Similarity	NPD7199	Phase 2
0.7091	Intermediate Similarity	NPD3751	Discontinued
0.708	Intermediate Similarity	NPD5536	Phase 2
0.7077	Intermediate Similarity	NPD9697	Approved
0.7075	Intermediate Similarity	NPD6355	Discontinued
0.7071	Intermediate Similarity	NPD1535	Discovery
0.7071	Intermediate Similarity	NPD1201	Approved
0.7067	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD5019	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD3787	Discontinued
0.7055	Intermediate Similarity	NPD7229	Phase 3
0.7054	Intermediate Similarity	NPD9261	Approved
0.7047	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7035	Intermediate Similarity	NPD4287	Approved
0.7034	Intermediate Similarity	NPD4625	Phase 3
0.7015	Intermediate Similarity	NPD1609	Clinical (unspecified phase)
0.7014	Intermediate Similarity	NPD3018	Phase 2
0.7012	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7012	Intermediate Similarity	NPD5242	Approved
0.7006	Intermediate Similarity	NPD7458	Discontinued
0.7006	Intermediate Similarity	NPD8158	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD1470	Approved
0.6987	Remote Similarity	NPD5586	Clinical (unspecified phase)
0.6972	Remote Similarity	NPD4749	Approved
0.6959	Remote Similarity	NPD4340	Discontinued
0.6959	Remote Similarity	NPD4622	Approved
0.6959	Remote Similarity	NPD4618	Approved
0.6951	Remote Similarity	NPD5711	Approved
0.6951	Remote Similarity	NPD5710	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