NPASS Compound

Structure

CID195202 OpenBabel06191715582D 24 26 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 -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 -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 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 -3.4641 -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 -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 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 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 21 1 0 0 0 0 2 22 1 0 0 0 0 3 23 1 0 0 0 0 4 5 2 0 0 0 0 4 10 1 0 0 0 0 5 14 1 0 0 0 0 6 10 2 0 0 0 0 6 16 1 0 0 0 0 7 11 2 0 0 0 0 7 12 1 0 0 0 0 8 11 1 0 0 0 0 8 17 2 0 0 0 0 9 13 1 0 0 0 0 9 15 2 0 0 0 0 10 15 1 0 0 0 0 11 21 1 0 0 0 0 12 18 2 0 0 0 0 12 19 1 0 0 0 0 13 18 1 0 0 0 0 13 20 2 0 0 0 0 14 16 2 0 0 0 0 14 22 1 0 0 0 0 15 24 1 0 0 0 0 16 23 1 0 0 0 0 17 18 1 0 0 0 0 17 24 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	328.09
Volume:	325.865
LogP:	3.615
LogD:	2.889
LogS:	-4.421
# Rotatable Bonds:	4
TPSA:	78.13
# H-Bond Aceptor:	6
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.792
Synthetic Accessibility Score:	2.148
Fsp3:	0.167
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:	-4.733
MDCK Permeability:	3.134089638479054e-05
Pgp-inhibitor:	0.933
Pgp-substrate:	0.018
Human Intestinal Absorption (HIA):	0.017
20% Bioavailability (F20%):	0.009
30% Bioavailability (F30%):	0.839

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.034
Plasma Protein Binding (PPB):	87.2718734741211%
Volume Distribution (VD):	0.785
Pgp-substrate:	11.311453819274902%

ADMET: Metabolism

CYP1A2-inhibitor:	0.957
CYP1A2-substrate:	0.966
CYP2C19-inhibitor:	0.794
CYP2C19-substrate:	0.295
CYP2C9-inhibitor:	0.726
CYP2C9-substrate:	0.925
CYP2D6-inhibitor:	0.481
CYP2D6-substrate:	0.939
CYP3A4-inhibitor:	0.799
CYP3A4-substrate:	0.346

ADMET: Excretion

Clearance (CL):	6.627
Half-life (T1/2):	0.509

ADMET: Toxicity

hERG Blockers:	0.052
Human Hepatotoxicity (H-HT):	0.171
Drug-inuced Liver Injury (DILI):	0.889
AMES Toxicity:	0.484
Rat Oral Acute Toxicity:	0.063
Maximum Recommended Daily Dose:	0.451
Skin Sensitization:	0.649
Carcinogencity:	0.039
Eye Corrosion:	0.004
Eye Irritation:	0.471
Respiratory Toxicity:	0.58

Download Data

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

Natural Product: NPC195202

Natural Product ID:	NPC195202
*Common Name:**	7,3',4'-Tri-O-Methylluteolin
IUPAC Name:	2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one
Synonyms:
Standard InCHIKey:	HIXDQWDOVZUNNA-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C18H16O6/c1-21-11-7-12(19)18-13(20)9-15(24-17(18)8-11)10-4-5-14(22-2)16(6-10)23-3/h4-9,19H,1-3H3
SMILES:	COc1cc(O)c2c(c1)oc(cc2=O)c1ccc(c(c1)OC)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL468876
PubChem CID:	5272653
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
NPO33004	lethedon tannaensis	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10075750]
NPO29103	Spongia matamata	Species	Spongiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[10075761]
NPO28014	Garcinia gaudichaudii	Species	Clusiaceae	Eukaryota	n.a.	bark	n.a.	PMID[11101460]
NPO22900	Orthosiphon stamineus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11374950]
NPO19451	Salvia prionitis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11473439]
NPO19451	Salvia prionitis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12141863]
NPO22900	Orthosiphon stamineus	Species	Lamiaceae	Eukaryota	n.a.	Indonesia	n.a.	PMID[12467611]
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]
NPO22900	Orthosiphon stamineus	Species	Lamiaceae	Eukaryota	aerial parts	Bangdung, Indonesia	2000-Aug	PMID[12608860]
NPO27888	Sarcococca saligna	Species	Buxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[14584959]
NPO27888	Sarcococca saligna	Species	Buxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[14643329]
NPO22900	Orthosiphon stamineus	Species	Lamiaceae	Eukaryota	n.a.	Taiwan	n.a.	PMID[15104497]
NPO29463	Pogostemon cablin	Species	Lamiaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[15577255]
NPO27718	Peperomia dindygulensis	Species	Piperaceae	Eukaryota	whole plant	Yunnan Province, China	2002-FEB	PMID[16309318]
NPO27718	Peperomia dindygulensis	Species	Piperaceae	Eukaryota	whole plant	Yunnan Province, China	2002-FEB	PMID[16724842]
NPO21944	Laurencia mariannensis	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18076141]
NPO16665	Tephrosia semiglabra	Species	Geometridae	Eukaryota	n.a.	n.a.	n.a.	PMID[2089123]
NPO9756	Daphne genkwa	Species	Thymelaeaceae	Eukaryota	n.a.	flower	n.a.	PMID[21916433]
NPO5877	Morus yunnanensis	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22165973]
NPO9756	Daphne genkwa	Species	Thymelaeaceae	Eukaryota	flower buds	n.a.	n.a.	PMID[23558238]
NPO19152	Empetrum nigrum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26473275]
NPO9756	Daphne genkwa	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27228307]
NPO23000	Zephyranthes carinata	Species	Amaryllidaceae	Eukaryota	Whole Plants	n.a.	n.a.	PMID[28898076]
NPO29463	Pogostemon cablin	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[30188125]
NPO9756	Daphne genkwa	Species	Thymelaeaceae	Eukaryota	Roots	n.a.	n.a.	PMID[31150241]
NPO3549	Euonymus maackii	Species	Celastraceae	Eukaryota	Seeds	n.a.	n.a.	PMID[31713425]
NPO9756	Daphne genkwa	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31860304]
NPO9756	Daphne genkwa	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32223193]
NPO33004	lethedon tannaensis	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8759170]
NPO27888	Sarcococca saligna	Species	Buxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9548847]
NPO23226	Satureja montana	Species	Lamiaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO19152	Empetrum nigrum	Species	Ericaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO22500	Stephania dielsiana	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21807	Lindera umbellata	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO27842	Gentiana makinoi	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19929	Jateorhiza palmata	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22661	Pinus aristata	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29463	Pogostemon cablin	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28939	Piptanthus nepalensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO27888	Sarcococca saligna	Species	Buxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19451	Salvia prionitis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO16710	Pandanus tectorius	Species	Pandanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23141	Angelica ursina	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21600	Aconitum variegatum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22900	Orthosiphon stamineus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9756	Daphne genkwa	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19152	Empetrum nigrum	Species	Ericaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO19152	Empetrum nigrum	Species	Ericaceae	Eukaryota	Fruits	n.a.		Database[Phenol-Explorer]
NPO23226	Satureja montana	Species	Lamiaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO13304	Piper spp.	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28014	Garcinia gaudichaudii	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27842	Gentiana makinoi	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28939	Piptanthus nepalensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22500	Stephania dielsiana	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22900	Orthosiphon stamineus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22661	Pinus aristata	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19451	Salvia prionitis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23141	Angelica ursina	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22462	Chlorophytum malayense	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29463	Pogostemon cablin	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16710	Pandanus tectorius	Species	Pandanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9756	Daphne genkwa	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21881	Stephania succifera	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21807	Lindera umbellata	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26562	Salvia spp.	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2116	Arnica spp.	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21600	Aconitum variegatum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19929	Jateorhiza palmata	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27888	Sarcococca saligna	Species	Buxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3549	Euonymus maackii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22071	Gentiana olivieri	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16710	Pandanus tectorius	Species	Pandanaceae	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]
NPO19929	Jateorhiza palmata	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO22900	Orthosiphon stamineus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO9756	Daphne genkwa	Species	Thymelaeaceae	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]
NPO19451	Salvia prionitis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO28939	Piptanthus nepalensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO21807	Lindera umbellata	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO29463	Pogostemon cablin	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO9756	Daphne genkwa	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO10353	Rauvolfia tetraphylla	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16665	Tephrosia semiglabra	Species	Geometridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19929	Jateorhiza palmata	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21545	Maytenus guianensis	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13728	Metanarthecium luteoviride	Species	Nartheciaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23101	Ircinia aruensis	Species	Irciniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22137	Vernonia serratuloides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23226	Satureja montana	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20584	Cheilanthes fragrans	Species	Pteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27135	Tubularia larynx	Species	Tubulariidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22071	Gentiana olivieri	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14664	Stevia salicifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21600	Aconitum variegatum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21680	Saussurea triangulata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19152	Empetrum nigrum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18852	Plenckia populnea	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22500	Stephania dielsiana	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22518	Gnetum cleistostachyum	Species	Gnetaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO984	Hippocrepis emerus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20726	Ophioplocus japonicus	Species	Ophiolepididae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25969	Aspergillus nomius	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27401	Aniba riparia	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16710	Pandanus tectorius	Species	Pandanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20100	Ephedra lomatolepis	Species	Ephedraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22015	Clausena indica	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21344	Fadogia agrestis	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27888	Sarcococca saligna	Species	Buxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22773	Teucrium alyssifolium	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28133	Geigeria filifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22952	Senecio grandiflorus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27184	Bonellia macrocarpa	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22405	Litsea monopetala	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28870	Clausena lenis	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27718	Peperomia dindygulensis	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22395	Ardisia macrocarpa	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22717	Pinus thunbergii	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22197	Eriogaster lanestris	Species	Lasiocampidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21807	Lindera umbellata	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11524	Macrotomia ugamensis	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13234	Gyalolechia fulgida	Species	Teloschistaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9756	Daphne genkwa	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27439	Letharia vulpina	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23000	Zephyranthes carinata	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28808	Piptanthus mongolicus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27953	Eugenia formosa	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29013	Annulohypoxylon cohaerens	Species	Xylariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5877	Morus yunnanensis	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21384	Tetraria capillaris	Species	Cyperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20964	Picradeniopsis oppositifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17401	Kopsia lapidilecta	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22462	Chlorophytum malayense	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22661	Pinus aristata	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28939	Piptanthus nepalensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28974	Smilax ornata	Species	Staphylinidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21944	Laurencia mariannensis	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3549	Euonymus maackii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28829	Pelvetia wrightii	Species	Fucaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16275	Pterocaulon rugosum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23183	Pinus halepensis	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29463	Pogostemon cablin	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21881	Stephania succifera	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22900	Orthosiphon stamineus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17547	Dryopteris arguta	Species	Dryopteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7320	Nicotiana gossei	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19451	Salvia prionitis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22911	Enterococcus faecalis	Species	Enterococcaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO21534	Ostrya carpinifolia	Species	Betulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29103	Spongia matamata	Species	Spongiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14529	Asterias rubens	Species	Asteriidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11024	Bellardia viscosa	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29194	Harziella entomophila	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO19590	Daedaleopsis tricolor	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17271	Aegialitis annulata	Species	Plumbaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27362	Hypericum elodes	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21140	Igernella notabilis	Species	Dictyodendrillidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23062	Melibe leonina	Species	Dendronotidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27842	Gentiana makinoi	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29402	Launaea arborescens	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28066	Aloe speciosa	Species	Xanthorrhoeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26540	Echinopsis spachiana	Species	Cactaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29157	Reichardia gaditana	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21745	Phleum africanum	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23141	Angelica ursina	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28014	Garcinia gaudichaudii	Species	Clusiaceae	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	8
Others	4

Activity Type	# Activity
Cell Line	8
NON-MOLECULAR	1
Organism	1
SINGLE PROTEIN	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	IC50	=	19.4	ug.mL-1	PMID[511798]
NPT83	Cell Line	MCF7	Homo sapiens	Activity	=	71.3	%	PMID[511799]
NPT83	Cell Line	MCF7	Homo sapiens	Activity	=	13.0	%	PMID[511799]
NPT65	Cell Line	HepG2	Homo sapiens	IC50	=	15000.0	nM	PMID[511799]
NPT189	Cell Line	Vero	Chlorocebus aethiops	IC50	=	125000.0	nM	PMID[511799]
NPT1374	Cell Line	WI-38	Homo sapiens	IC50	=	105000.0	nM	PMID[511799]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	10000.0	nM	PMID[511799]
NPT885	Cell Line	PBL		Activity	=	65.0	%	PMID[511799]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	45.8	%	PMID[511799]
NPT21851	SINGLE PROTEIN	Dihydroorotate dehydrogenase (fumarate)	Leishmania major	IC50	=	217000.0	nM	PMID[511800]
NPT21851	SINGLE PROTEIN	Dihydroorotate dehydrogenase (fumarate)	Leishmania major	IC50	=	199526.23	nM	PMID[511800]
NPT580	Organism	Trypanosoma cruzi	Trypanosoma cruzi	IC50	=	217300.0	nM	PMID[511800]

☑ 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 NPC195202 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	450
0.1-0.2	1931
0.2-0.3	4825
0.3-0.4	11259
0.4-0.5	6122
0.5-0.6	3684
0.6-0.7	4988
0.7-0.8	4825
0.8-0.85	2273
0.85-0.9	1479
0.9-0.95	679
0.95-1	182

Similarity Score	Similarity Level	Natural Product ID
0.9929	High Similarity	NPC62536
0.9929	High Similarity	NPC12200
0.9929	High Similarity	NPC33265
0.986	High Similarity	NPC50728
0.986	High Similarity	NPC166753
0.9792	High Similarity	NPC236769
0.9792	High Similarity	NPC226973
0.9792	High Similarity	NPC208043
0.9792	High Similarity	NPC308451
0.979	High Similarity	NPC137062
0.979	High Similarity	NPC177298
0.979	High Similarity	NPC159103
0.979	High Similarity	NPC328119
0.979	High Similarity	NPC223579
0.979	High Similarity	NPC48479
0.979	High Similarity	NPC183950
0.979	High Similarity	NPC287101
0.979	High Similarity	NPC52005
0.9724	High Similarity	NPC39732
0.9724	High Similarity	NPC60972
0.9722	High Similarity	NPC306821
0.9722	High Similarity	NPC219330
0.972	High Similarity	NPC120464
0.972	High Similarity	NPC261548
0.9658	High Similarity	NPC47781
0.9658	High Similarity	NPC183878
0.9658	High Similarity	NPC160951
0.9658	High Similarity	NPC86485
0.9658	High Similarity	NPC236223
0.9658	High Similarity	NPC270620
0.9658	High Similarity	NPC69394
0.9658	High Similarity	NPC22519
0.9658	High Similarity	NPC255350
0.9658	High Similarity	NPC78326
0.9658	High Similarity	NPC145379
0.9658	High Similarity	NPC176775
0.9658	High Similarity	NPC179126
0.9658	High Similarity	NPC231018
0.9658	High Similarity	NPC274327
0.9655	High Similarity	NPC252933
0.9655	High Similarity	NPC76376
0.9655	High Similarity	NPC200740
0.9655	High Similarity	NPC54394
0.9655	High Similarity	NPC125062
0.965	High Similarity	NPC108406
0.9645	High Similarity	NPC70853
0.9645	High Similarity	NPC9966
0.9592	High Similarity	NPC20830
0.9592	High Similarity	NPC183597
0.9592	High Similarity	NPC50715
0.9592	High Similarity	NPC227325
0.9592	High Similarity	NPC163780
0.9592	High Similarity	NPC196439
0.9592	High Similarity	NPC201136
0.9592	High Similarity	NPC256612
0.9592	High Similarity	NPC128863
0.9592	High Similarity	NPC92659
0.9592	High Similarity	NPC213622
0.9592	High Similarity	NPC146165
0.9592	High Similarity	NPC167815
0.9592	High Similarity	NPC4455
0.9592	High Similarity	NPC2476
0.9592	High Similarity	NPC189960
0.9592	High Similarity	NPC138360
0.9592	High Similarity	NPC280339
0.9592	High Similarity	NPC32557
0.9589	High Similarity	NPC162313
0.9589	High Similarity	NPC71334
0.9589	High Similarity	NPC156222
0.9589	High Similarity	NPC301123
0.9589	High Similarity	NPC82325
0.9589	High Similarity	NPC275836
0.9589	High Similarity	NPC188203
0.9589	High Similarity	NPC55205
0.9589	High Similarity	NPC120163
0.9589	High Similarity	NPC83508
0.9589	High Similarity	NPC241498
0.9589	High Similarity	NPC198826
0.9589	High Similarity	NPC187498
0.9589	High Similarity	NPC57030
0.9589	High Similarity	NPC301323
0.9589	High Similarity	NPC100887
0.9589	High Similarity	NPC212678
0.9589	High Similarity	NPC222830
0.9589	High Similarity	NPC131624
0.9589	High Similarity	NPC239128
0.9589	High Similarity	NPC293183
0.9589	High Similarity	NPC25270
0.9589	High Similarity	NPC279989
0.9589	High Similarity	NPC471982
0.9589	High Similarity	NPC256283
0.9589	High Similarity	NPC275722
0.9586	High Similarity	NPC338131
0.9577	High Similarity	NPC113089
0.9574	High Similarity	NPC29536
0.9527	High Similarity	NPC49824
0.9527	High Similarity	NPC265511
0.9527	High Similarity	NPC178854
0.9524	High Similarity	NPC276409
0.9524	High Similarity	NPC162351
0.9524	High Similarity	NPC18727
0.9524	High Similarity	NPC75279
0.9524	High Similarity	NPC246204
0.9524	High Similarity	NPC472915
0.9524	High Similarity	NPC280937
0.9524	High Similarity	NPC250822
0.9524	High Similarity	NPC58382
0.9521	High Similarity	NPC133953
0.9521	High Similarity	NPC28274
0.9521	High Similarity	NPC117579
0.9521	High Similarity	NPC50403
0.9517	High Similarity	NPC87125
0.9517	High Similarity	NPC270465
0.951	High Similarity	NPC136278
0.9507	High Similarity	NPC119663
0.9463	High Similarity	NPC224137
0.9463	High Similarity	NPC189179
0.9463	High Similarity	NPC93376
0.9463	High Similarity	NPC75215
0.9463	High Similarity	NPC470402
0.9463	High Similarity	NPC110070
0.9463	High Similarity	NPC183
0.9463	High Similarity	NPC183851
0.9463	High Similarity	NPC227192
0.9463	High Similarity	NPC63454
0.9463	High Similarity	NPC101830
0.9463	High Similarity	NPC473272
0.9463	High Similarity	NPC476981
0.9463	High Similarity	NPC203891
0.9463	High Similarity	NPC284820
0.9459	High Similarity	NPC44079
0.9459	High Similarity	NPC26227
0.9459	High Similarity	NPC234255
0.9459	High Similarity	NPC472909
0.9459	High Similarity	NPC255807
0.9459	High Similarity	NPC201451
0.9459	High Similarity	NPC208197
0.9459	High Similarity	NPC37392
0.9459	High Similarity	NPC31018
0.9459	High Similarity	NPC226025
0.9456	High Similarity	NPC477231
0.9456	High Similarity	NPC123886
0.9456	High Similarity	NPC219582
0.9456	High Similarity	NPC142540
0.9456	High Similarity	NPC302950
0.9456	High Similarity	NPC134677
0.9456	High Similarity	NPC236637
0.9456	High Similarity	NPC472912
0.9456	High Similarity	NPC257648
0.9452	High Similarity	NPC88804
0.9452	High Similarity	NPC188871
0.9452	High Similarity	NPC149127
0.9452	High Similarity	NPC184136
0.9452	High Similarity	NPC286342
0.9452	High Similarity	NPC3825
0.9448	High Similarity	NPC119059
0.9444	High Similarity	NPC310259
0.9444	High Similarity	NPC14958
0.9444	High Similarity	NPC40818
0.9444	High Similarity	NPC106461
0.9444	High Similarity	NPC110639
0.9444	High Similarity	NPC215932
0.9444	High Similarity	NPC12377
0.9441	High Similarity	NPC279121
0.94	High Similarity	NPC4481
0.94	High Similarity	NPC22472
0.94	High Similarity	NPC476410
0.94	High Similarity	NPC18772
0.94	High Similarity	NPC172202
0.94	High Similarity	NPC176300
0.94	High Similarity	NPC19687
0.94	High Similarity	NPC105242
0.94	High Similarity	NPC288669
0.94	High Similarity	NPC7846
0.94	High Similarity	NPC261004
0.94	High Similarity	NPC25495
0.94	High Similarity	NPC115798
0.94	High Similarity	NPC9609
0.94	High Similarity	NPC18607
0.94	High Similarity	NPC143828
0.94	High Similarity	NPC191459
0.94	High Similarity	NPC300943
0.94	High Similarity	NPC152166
0.94	High Similarity	NPC253634
0.94	High Similarity	NPC204854
0.94	High Similarity	NPC130894
0.94	High Similarity	NPC284127
0.9396	High Similarity	NPC98661
0.9396	High Similarity	NPC55619
0.9396	High Similarity	NPC247017
0.9396	High Similarity	NPC245546
0.9396	High Similarity	NPC291878
0.9396	High Similarity	NPC471985
0.9396	High Similarity	NPC200388
0.9396	High Similarity	NPC278778
0.9396	High Similarity	NPC474520
0.9396	High Similarity	NPC35038
0.9396	High Similarity	NPC266960
0.9396	High Similarity	NPC43243
0.9396	High Similarity	NPC292107

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 NPC195202 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	426
0.1-0.2	968
0.2-0.3	1749
0.3-0.4	2651
0.4-0.5	1760
0.5-0.6	1028
0.6-0.7	390
0.7-0.8	110
0.8-0.85	37
0.85-0.9	23
0.9-0.95	5
0.95-1	3

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9658	High Similarity	NPD2801	Approved
0.9456	High Similarity	NPD1934	Approved
0.9441	High Similarity	NPD1511	Approved
0.931	High Similarity	NPD1512	Approved
0.9262	High Similarity	NPD2393	Clinical (unspecified phase)
0.92	High Similarity	NPD3817	Phase 2
0.9139	High Similarity	NPD3882	Suspended
0.911	High Similarity	NPD4378	Clinical (unspecified phase)
0.8974	High Similarity	NPD6167	Clinical (unspecified phase)
0.8974	High Similarity	NPD6168	Clinical (unspecified phase)
0.8974	High Similarity	NPD6166	Phase 2
0.8924	High Similarity	NPD7054	Approved
0.8868	High Similarity	NPD7472	Approved
0.8861	High Similarity	NPD3818	Discontinued
0.8759	High Similarity	NPD1552	Clinical (unspecified phase)
0.8759	High Similarity	NPD1550	Clinical (unspecified phase)
0.875	High Similarity	NPD1510	Phase 2
0.875	High Similarity	NPD7074	Phase 3
0.8704	High Similarity	NPD7808	Phase 3
0.8699	High Similarity	NPD1549	Phase 2
0.8696	High Similarity	NPD6797	Phase 2
0.869	High Similarity	NPD2796	Approved
0.8684	High Similarity	NPD4380	Phase 2
0.8642	High Similarity	NPD7251	Discontinued
0.8608	High Similarity	NPD6232	Discontinued
0.8601	High Similarity	NPD1240	Approved
0.86	High Similarity	NPD7410	Clinical (unspecified phase)
0.8599	High Similarity	NPD5494	Approved
0.859	High Similarity	NPD4381	Clinical (unspecified phase)
0.8589	High Similarity	NPD4338	Clinical (unspecified phase)
0.8562	High Similarity	NPD7473	Discontinued
0.8533	High Similarity	NPD6799	Approved
0.8526	High Similarity	NPD4868	Clinical (unspecified phase)
0.8483	Intermediate Similarity	NPD1607	Approved
0.8471	Intermediate Similarity	NPD7075	Discontinued
0.8446	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8397	Intermediate Similarity	NPD7819	Suspended
0.8397	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8344	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD6801	Discontinued
0.8269	Intermediate Similarity	NPD7411	Suspended
0.8232	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8232	Intermediate Similarity	NPD5844	Phase 1
0.8228	Intermediate Similarity	NPD5402	Approved
0.8219	Intermediate Similarity	NPD943	Approved
0.8212	Intermediate Similarity	NPD3750	Approved
0.821	Intermediate Similarity	NPD3926	Phase 2
0.8205	Intermediate Similarity	NPD6599	Discontinued
0.8199	Intermediate Similarity	NPD6959	Discontinued
0.8199	Intermediate Similarity	NPD1247	Approved
0.8187	Intermediate Similarity	NPD919	Approved
0.8165	Intermediate Similarity	NPD1465	Phase 2
0.8163	Intermediate Similarity	NPD447	Suspended
0.8129	Intermediate Similarity	NPD5403	Approved
0.8129	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.8082	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8069	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.8067	Intermediate Similarity	NPD2935	Discontinued
0.8067	Intermediate Similarity	NPD1551	Phase 2
0.8026	Intermediate Similarity	NPD2800	Approved
0.8024	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD5401	Approved
0.8	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7976	Intermediate Similarity	NPD6559	Discontinued
0.7973	Intermediate Similarity	NPD1613	Approved
0.7973	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.795	Intermediate Similarity	NPD7768	Phase 2
0.7939	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7935	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7919	Intermediate Similarity	NPD230	Phase 1
0.7919	Intermediate Similarity	NPD1933	Approved
0.7908	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7901	Intermediate Similarity	NPD3749	Approved
0.7891	Intermediate Similarity	NPD3027	Phase 3
0.7885	Intermediate Similarity	NPD2532	Approved
0.7885	Intermediate Similarity	NPD2534	Approved
0.7885	Intermediate Similarity	NPD2533	Approved
0.7881	Intermediate Similarity	NPD3748	Approved
0.7857	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7829	Intermediate Similarity	NPD6099	Approved
0.7829	Intermediate Similarity	NPD6100	Approved
0.7792	Intermediate Similarity	NPD1243	Approved
0.7785	Intermediate Similarity	NPD920	Approved
0.7778	Intermediate Similarity	NPD2344	Approved
0.7763	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7758	Intermediate Similarity	NPD7199	Phase 2
0.7748	Intermediate Similarity	NPD6651	Approved
0.7742	Intermediate Similarity	NPD4628	Phase 3
0.774	Intermediate Similarity	NPD1203	Approved
0.7724	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7719	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7718	Intermediate Similarity	NPD2313	Discontinued
0.7688	Intermediate Similarity	NPD3226	Approved
0.7676	Intermediate Similarity	NPD1548	Phase 1
0.7667	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7665	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7658	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD2799	Discontinued
0.7647	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7643	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7635	Intermediate Similarity	NPD9494	Approved
0.7625	Intermediate Similarity	NPD1653	Approved
0.7602	Intermediate Similarity	NPD5953	Discontinued
0.76	Intermediate Similarity	NPD3268	Approved
0.7595	Intermediate Similarity	NPD7390	Discontinued
0.7588	Intermediate Similarity	NPD7286	Phase 2
0.7586	Intermediate Similarity	NPD422	Phase 1
0.7584	Intermediate Similarity	NPD6832	Phase 2
0.7584	Intermediate Similarity	NPD4908	Phase 1
0.758	Intermediate Similarity	NPD2309	Approved
0.7568	Intermediate Similarity	NPD2798	Approved
0.7566	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7548	Intermediate Similarity	NPD2346	Discontinued
0.7546	Intermediate Similarity	NPD37	Approved
0.7534	Intermediate Similarity	NPD9717	Approved
0.7532	Intermediate Similarity	NPD7033	Discontinued
0.753	Intermediate Similarity	NPD6234	Discontinued
0.7529	Intermediate Similarity	NPD3751	Discontinued
0.7517	Intermediate Similarity	NPD3018	Phase 2
0.7516	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD4965	Approved
0.7515	Intermediate Similarity	NPD4967	Phase 2
0.7515	Intermediate Similarity	NPD4966	Approved
0.75	Intermediate Similarity	NPD3787	Discontinued
0.75	Intermediate Similarity	NPD2797	Approved
0.7483	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD5536	Phase 2
0.7468	Intermediate Similarity	NPD6190	Approved
0.7466	Intermediate Similarity	NPD1610	Phase 2
0.7466	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7458	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7456	Intermediate Similarity	NPD5242	Approved
0.7452	Intermediate Similarity	NPD2654	Approved
0.7432	Intermediate Similarity	NPD3225	Approved
0.7419	Intermediate Similarity	NPD4308	Phase 3
0.7415	Intermediate Similarity	NPD1608	Approved
0.7389	Intermediate Similarity	NPD4363	Phase 3
0.7389	Intermediate Similarity	NPD4360	Phase 2
0.7378	Intermediate Similarity	NPD6386	Approved
0.7378	Intermediate Similarity	NPD6385	Approved
0.7375	Intermediate Similarity	NPD4357	Discontinued
0.7368	Intermediate Similarity	NPD411	Approved
0.7365	Intermediate Similarity	NPD2983	Phase 2
0.7365	Intermediate Similarity	NPD2982	Phase 2
0.7356	Intermediate Similarity	NPD7685	Pre-registration
0.7349	Intermediate Similarity	NPD5353	Approved
0.7333	Intermediate Similarity	NPD6844	Discontinued
0.7329	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD2403	Approved
0.7308	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD4625	Phase 3
0.7297	Intermediate Similarity	NPD9269	Phase 2
0.7297	Intermediate Similarity	NPD2981	Phase 2
0.7294	Intermediate Similarity	NPD5710	Approved
0.7294	Intermediate Similarity	NPD5711	Approved
0.7288	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD3267	Approved
0.7267	Intermediate Similarity	NPD3266	Approved
0.726	Intermediate Similarity	NPD9268	Approved
0.7255	Intermediate Similarity	NPD6798	Discontinued
0.7253	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7253	Intermediate Similarity	NPD4361	Phase 2
0.7248	Intermediate Similarity	NPD4749	Approved
0.7246	Intermediate Similarity	NPD4288	Approved
0.7233	Intermediate Similarity	NPD1652	Phase 2
0.723	Intermediate Similarity	NPD1201	Approved
0.7225	Intermediate Similarity	NPD7228	Approved
0.7211	Intermediate Similarity	NPD17	Approved
0.7209	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD6233	Phase 2
0.7193	Intermediate Similarity	NPD7229	Phase 3
0.7192	Intermediate Similarity	NPD9545	Approved
0.7181	Intermediate Similarity	NPD3972	Approved
0.7175	Intermediate Similarity	NPD8313	Approved
0.7175	Intermediate Similarity	NPD8312	Approved
0.7172	Intermediate Similarity	NPD9493	Approved
0.7171	Intermediate Similarity	NPD2861	Phase 2
0.7169	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7161	Intermediate Similarity	NPD4307	Phase 2
0.716	Intermediate Similarity	NPD6971	Discontinued
0.7159	Intermediate Similarity	NPD7039	Approved
0.7159	Intermediate Similarity	NPD7038	Approved
0.7152	Intermediate Similarity	NPD7458	Discontinued
0.7152	Intermediate Similarity	NPD1470	Approved
0.7151	Intermediate Similarity	NPD8434	Phase 2
0.7143	Intermediate Similarity	NPD7584	Approved
0.7143	Intermediate Similarity	NPD1296	Phase 2
0.7119	Intermediate Similarity	NPD7549	Discontinued
0.7117	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD5124	Phase 1
0.7115	Intermediate Similarity	NPD6355	Discontinued
0.7115	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD1019	Discontinued
0.7101	Intermediate Similarity	NPD5019	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD1241	Discontinued
0.7083	Intermediate Similarity	NPD5283	Phase 1
0.7081	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD4110	Phase 3
0.7073	Intermediate Similarity	NPD1940	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