NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	256.07
Volume:	259.033
LogP:	3.718
LogD:	2.948
LogS:	-3.369
# Rotatable Bonds:	0
TPSA:	80.92
# H-Bond Aceptor:	4
# H-Bond Donor:	4
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.466
Synthetic Accessibility Score:	2.567
Fsp3:	0.067
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:	-5.127
MDCK Permeability:	5.66713561056531e-06
Pgp-inhibitor:	0.011
Pgp-substrate:	0.006
Human Intestinal Absorption (HIA):	0.113
20% Bioavailability (F20%):	0.927
30% Bioavailability (F30%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.012
Plasma Protein Binding (PPB):	97.26334381103516%
Volume Distribution (VD):	0.534
Pgp-substrate:	3.5157532691955566%

ADMET: Metabolism

CYP1A2-inhibitor:	0.986
CYP1A2-substrate:	0.618
CYP2C19-inhibitor:	0.143
CYP2C19-substrate:	0.056
CYP2C9-inhibitor:	0.595
CYP2C9-substrate:	0.82
CYP2D6-inhibitor:	0.563
CYP2D6-substrate:	0.354
CYP3A4-inhibitor:	0.169
CYP3A4-substrate:	0.083

ADMET: Excretion

Clearance (CL):	11.092
Half-life (T1/2):	0.877

ADMET: Toxicity

hERG Blockers:	0.03
Human Hepatotoxicity (H-HT):	0.093
Drug-inuced Liver Injury (DILI):	0.771
AMES Toxicity:	0.629
Rat Oral Acute Toxicity:	0.219
Maximum Recommended Daily Dose:	0.944
Skin Sensitization:	0.956
Carcinogencity:	0.088
Eye Corrosion:	0.062
Eye Irritation:	0.952
Respiratory Toxicity:	0.611

Download Data

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

Natural Product: NPC267205

Natural Product ID:	NPC267205
*Common Name:**	Emodin Anthrone
IUPAC Name:	1,3,8-trihydroxy-6-methyl-10H-anthracen-9-one
Synonyms:	Emodin Anthrone
Standard InCHIKey:	LAJSXCAVRQXZIO-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C15H12O4/c1-7-2-8-4-9-5-10(16)6-12(18)14(9)15(19)13(8)11(17)3-7/h2-3,5-6,16-18H,4H2,1H3
SMILES:	Cc1cc2Cc3cc(cc(c3C(=O)c2c(c1)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL122192
PubChem CID:	122635
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000018] Anthracenes

*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
NPO12955	Rumex crispus	Species	Polygonaceae	Eukaryota	n.a.	leaf	n.a.	DOI[10.1002/ardp.19542870405]
NPO11391	Polygonum cuspidatum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11076555]
NPO27239	Maclura tinctoria	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11087602]
NPO11391	Polygonum cuspidatum	Species	Polygonaceae	Eukaryota	Roots	n.a.	n.a.	PMID[11459643]
NPO23024	Epimedium koreanum	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12081149]
NPO27239	Maclura tinctoria	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12932124]
NPO27239	Maclura tinctoria	Species	Moraceae	Eukaryota	n.a.	stem	n.a.	PMID[12932124]
NPO11391	Polygonum cuspidatum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1517743]
NPO29417	Fallopia multiflora	Species	Polygonaceae	Eukaryota	n.a.	root	n.a.	PMID[16564530]
NPO30179	Cassia occidentalis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21080643]
NPO23024	Epimedium koreanum	Species	Berberidaceae	Eukaryota	n.a.	root	n.a.	PMID[22051934]
NPO31520	Polygonum multiflorum	Species	Polygonaceae	Eukaryota	roots	n.a.	n.a.	PMID[24499304]
NPO23024	Epimedium koreanum	Species	Berberidaceae	Eukaryota	aerial parts	herbal garden of Chungbuk National University, Cheongju, Korea	2012-Oct	PMID[24963714]
NPO31136	Cassia tora	Species	Fabaceae	Eukaryota	seeds	n.a.	n.a.	PMID[26483136]
NPO23736	Myrsine africana	Species	Primulaceae	Eukaryota	root	n.a.	n.a.	PMID[2778455]
NPO23736	Myrsine africana	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[29300477]
NPO29417	Fallopia multiflora	Species	Polygonaceae	Eukaryota	Roots	n.a.	n.a.	PMID[29359942]
NPO27164	Aspergillus alliaceus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[29517220]
NPO29417	Fallopia multiflora	Species	Polygonaceae	Eukaryota	Roots	n.a.	n.a.	PMID[31944695]
NPO27164	Aspergillus alliaceus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[3417561]
NPO29417	Fallopia multiflora	Species	Polygonaceae	Eukaryota	Roots; Tubers	n.a.	n.a.	PMID[7714535]
NPO11391	Polygonum cuspidatum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8277318]
NPO23024	Epimedium koreanum	Species	Berberidaceae	Eukaryota	n.a.	aerial part	n.a.	Database[Article]
NPO23736	Myrsine africana	Species	Primulaceae	Eukaryota	n.a.	fruit	n.a.	Database[Article]
NPO1475.1	Lilium brownii var. viridulum	Varieties	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23024	Epimedium koreanum	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11391	Polygonum cuspidatum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24601	Rumex dentatus	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23736	Myrsine africana	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7632	Rheum tanguticum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO27678	Boehmeria platanifolia	Species	Urticaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO31520	Polygonum multiflorum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12955	Rumex crispus	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO30326	Polygonum perfoliatum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28024	Rheum palmatum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO20881	Rheum officinale	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO31136	Cassia tora	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25658	Rumex japonicus	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO574	Rumex nepalensis	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO30179	Cassia occidentalis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18339	Rheum wittrocki	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3004	Ventilago calyculata	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13054	Rhamnus davurica	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18681	Artemisia scoparia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO30631	Rhamnus frangula	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18681	Artemisia scoparia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3004	Ventilago calyculata	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13054	Rhamnus davurica	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12327	Senna occidentalis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27678	Boehmeria platanifolia	Species	Urticaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24601	Rumex dentatus	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28024	Rheum palmatum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23736	Myrsine africana	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO574	Rumex nepalensis	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7632	Rheum tanguticum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1475.1	Lilium brownii var. viridulum	Varieties	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27140	Amanita phalloides	Species	Amanitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18339	Rheum wittrocki	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6826	Persicaria perfoliata	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23024	Epimedium koreanum	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7672	Senna tora	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29417	Fallopia multiflora	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12955	Rumex crispus	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11391	Polygonum cuspidatum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20881	Rheum officinale	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25658	Rumex japonicus	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19050	Garcinia polyantha	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5990	Frangula alnus	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3980	Frangula purshiana	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO30179	Cassia occidentalis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO30631	Rhamnus frangula	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO25658	Rumex japonicus	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO11391	Polygonum cuspidatum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO7632	Rheum tanguticum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO28024	Rheum palmatum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO13054	Rhamnus davurica	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO18339	Rheum wittrocki	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO31136	Cassia tora	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO20881	Rheum officinale	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO24601	Rumex dentatus	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO23024	Epimedium koreanum	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO18681	Artemisia scoparia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO31520	Polygonum multiflorum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO574	Rumex nepalensis	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO6826	Persicaria perfoliata	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO7672	Senna tora	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO23024	Epimedium koreanum	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO28024	Rheum palmatum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO29417	Fallopia multiflora	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO20881	Rheum officinale	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO11391	Polygonum cuspidatum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO7632	Rheum tanguticum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO25658	Rumex japonicus	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO27164	Aspergillus alliaceus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13054	Rhamnus davurica	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5990	Frangula alnus	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26972	Baccharis potosina	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4132	Cranfillia fluviatilis	Species	Blechnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27239	Maclura tinctoria	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27454	Turbo cornutus	Species	Turbinidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3004	Ventilago calyculata	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6826	Persicaria perfoliata	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28024	Rheum palmatum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25658	Rumex japonicus	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12955	Rumex crispus	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7672	Senna tora	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27873	Ravenia spectabilis	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24629	Achromobacter denitrificans	Species	Alcaligenaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO11391	Polygonum cuspidatum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3980	Frangula purshiana	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO574	Rumex nepalensis	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12327	Senna occidentalis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27790	Delia arenicola	Species	Anthomyiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17822	Fridericia triplinervia	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23024	Epimedium koreanum	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23736	Myrsine africana	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20881	Rheum officinale	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27564	Stevia berlandieri	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18681	Artemisia scoparia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10239	Magnolia figo	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27678	Boehmeria platanifolia	Species	Urticaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24601	Rumex dentatus	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27140	Amanita phalloides	Species	Amanitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7632	Rheum tanguticum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19050	Garcinia polyantha	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	3
Ki	1
Others	6

Activity Type	# Activity
Cell Line	3
Individual Protein	4
Others	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT3021	Individual Protein	Arachidonate 5-lipoxygenase	Bos taurus	IC50	=	14000.0	nM	PMID[559973]
NPT941	Cell Line	HaCaT	Homo sapiens	IC50	>	5000.0	nM	PMID[559973]
NPT941	Cell Line	HaCaT	Homo sapiens	LDH	=	114.0	MU	PMID[559973]
NPT91	Cell Line	KB	Homo sapiens	IC50	=	3900.0	nM	PMID[559974]
NPT2757	Individual Protein	Purinergic receptor P2Y12	Homo sapiens	Ki	>	10000.0	nM	PMID[559975]
NPT2757	Individual Protein	Purinergic receptor P2Y12	Homo sapiens	Inhibition	=	1.0	%	PMID[559975]
NPT35	Others	n.a.		LogP	=	3.9	n.a.	PMID[559973]
NPT610	Others	Molecular identity unknown		kDPPH	=	21.4	M-1 s-1	PMID[559973]
NPT610	Others	Molecular identity unknown		Ratio	=	2.04	n.a.	PMID[559973]
NPT946	Individual Protein	ATP-citrate synthase	Homo sapiens	Inhibition	=	0.0	%	PMID[559977]

☑ 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 NPC267205 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	410
0.1-0.2	1806
0.2-0.3	4033
0.3-0.4	11267
0.4-0.5	7578
0.5-0.6	5214
0.6-0.7	6162
0.7-0.8	4926
0.8-0.85	912
0.85-0.9	302
0.9-0.95	76
0.95-1	11

Similarity Score	Similarity Level	Natural Product ID
0.9767	High Similarity	NPC191976
0.9767	High Similarity	NPC254847
0.9692	High Similarity	NPC471905
0.9692	High Similarity	NPC53414
0.9692	High Similarity	NPC53206
0.9545	High Similarity	NPC242994
0.9545	High Similarity	NPC143438
0.9545	High Similarity	NPC138099
0.9474	High Similarity	NPC169452
0.9474	High Similarity	NPC181560
0.9462	High Similarity	NPC44437
0.9403	High Similarity	NPC246638
0.9403	High Similarity	NPC204045
0.9403	High Similarity	NPC305845
0.9398	High Similarity	NPC190457
0.9333	High Similarity	NPC193555
0.9333	High Similarity	NPC135524
0.9333	High Similarity	NPC474961
0.9318	High Similarity	NPC118919
0.9313	High Similarity	NPC166480
0.9313	High Similarity	NPC282780
0.9265	High Similarity	NPC174905
0.9265	High Similarity	NPC313047
0.9265	High Similarity	NPC295712
0.9265	High Similarity	NPC474203
0.9265	High Similarity	NPC451542
0.9265	High Similarity	NPC293545
0.9259	High Similarity	NPC110810
0.9259	High Similarity	NPC290550
0.9248	High Similarity	NPC53001
0.9237	High Similarity	NPC48036
0.9225	High Similarity	NPC92624
0.9197	High Similarity	NPC21599
0.9197	High Similarity	NPC244691
0.9197	High Similarity	NPC227841
0.9197	High Similarity	NPC193703
0.9197	High Similarity	NPC471906
0.9197	High Similarity	NPC48762
0.9191	High Similarity	NPC73061
0.9179	High Similarity	NPC87723
0.9167	High Similarity	NPC474519
0.9167	High Similarity	NPC12070
0.916	High Similarity	NPC175738
0.9154	High Similarity	NPC259942
0.9154	High Similarity	NPC62219
0.9141	High Similarity	NPC160499
0.9134	High Similarity	NPC173978
0.913	High Similarity	NPC12402
0.913	High Similarity	NPC34482
0.9098	High Similarity	NPC290803
0.9098	High Similarity	NPC249272
0.9091	High Similarity	NPC114183
0.9091	High Similarity	NPC37299
0.9091	High Similarity	NPC180261
0.9077	High Similarity	NPC99731
0.9065	High Similarity	NPC470570
0.9062	High Similarity	NPC477454
0.9062	High Similarity	NPC10926
0.9051	High Similarity	NPC182255
0.9051	High Similarity	NPC94076
0.9044	High Similarity	NPC203063
0.9023	High Similarity	NPC270899
0.9	High Similarity	NPC312929
0.9	High Similarity	NPC190648
0.9	High Similarity	NPC126767
0.9	High Similarity	NPC118027
0.9	High Similarity	NPC37709
0.9	High Similarity	NPC289042
0.9	High Similarity	NPC34802
0.9	High Similarity	NPC282923
0.9	High Similarity	NPC290194
0.9	High Similarity	NPC245584
0.9	High Similarity	NPC56433
0.8992	High Similarity	NPC473691
0.8992	High Similarity	NPC267846
0.8992	High Similarity	NPC8745
0.8986	High Similarity	NPC84266
0.8986	High Similarity	NPC296752
0.8984	High Similarity	NPC13238
0.8955	High Similarity	NPC161632
0.8955	High Similarity	NPC278375
0.8947	High Similarity	NPC314048
0.8939	High Similarity	NPC72669
0.8939	High Similarity	NPC474517
0.8931	High Similarity	NPC474998
0.8931	High Similarity	NPC109123
0.8923	High Similarity	NPC30501
0.8923	High Similarity	NPC162612
0.8923	High Similarity	NPC100067
0.8923	High Similarity	NPC116513
0.8923	High Similarity	NPC103356
0.8923	High Similarity	NPC23126
0.8923	High Similarity	NPC266689
0.8923	High Similarity	NPC169250
0.8923	High Similarity	NPC98254
0.8923	High Similarity	NPC72158
0.8923	High Similarity	NPC190043
0.8923	High Similarity	NPC105157
0.8921	High Similarity	NPC19896
0.8921	High Similarity	NPC10764
0.8915	High Similarity	NPC201728
0.8915	High Similarity	NPC262671
0.8898	High Similarity	NPC242895
0.8898	High Similarity	NPC215392
0.8897	High Similarity	NPC4214
0.8897	High Similarity	NPC416
0.8897	High Similarity	NPC61398
0.8897	High Similarity	NPC13715
0.8889	High Similarity	NPC158481
0.8873	High Similarity	NPC329933
0.8873	High Similarity	NPC477221
0.8865	High Similarity	NPC22005
0.8865	High Similarity	NPC123202
0.8865	High Similarity	NPC7943
0.8864	High Similarity	NPC147757
0.8855	High Similarity	NPC473017
0.8855	High Similarity	NPC21305
0.8855	High Similarity	NPC41263
0.8855	High Similarity	NPC221777
0.8849	High Similarity	NPC238629
0.8846	High Similarity	NPC62952
0.8841	High Similarity	NPC187843
0.8832	High Similarity	NPC162939
0.8828	High Similarity	NPC91105
0.8828	High Similarity	NPC32032
0.8828	High Similarity	NPC133909
0.8824	High Similarity	NPC290030
0.8819	High Similarity	NPC146642
0.8815	High Similarity	NPC283088
0.8811	High Similarity	NPC255641
0.8811	High Similarity	NPC290954
0.8811	High Similarity	NPC147735
0.8811	High Similarity	NPC470568
0.8811	High Similarity	NPC294646
0.8806	High Similarity	NPC52407
0.8803	High Similarity	NPC27221
0.8803	High Similarity	NPC256672
0.8803	High Similarity	NPC7025
0.8803	High Similarity	NPC471907
0.8797	High Similarity	NPC93015
0.8797	High Similarity	NPC205992
0.8797	High Similarity	NPC41847
0.8794	High Similarity	NPC110882
0.8794	High Similarity	NPC271944
0.8794	High Similarity	NPC85393
0.8769	High Similarity	NPC103540
0.8769	High Similarity	NPC475733
0.876	High Similarity	NPC65761
0.876	High Similarity	NPC472029
0.875	High Similarity	NPC35
0.875	High Similarity	NPC115159
0.875	High Similarity	NPC267552
0.875	High Similarity	NPC156139
0.875	High Similarity	NPC65005
0.875	High Similarity	NPC45438
0.875	High Similarity	NPC478148
0.875	High Similarity	NPC470569
0.875	High Similarity	NPC194764
0.875	High Similarity	NPC224273
0.875	High Similarity	NPC149526
0.875	High Similarity	NPC73532
0.875	High Similarity	NPC264112
0.875	High Similarity	NPC143427
0.875	High Similarity	NPC223836
0.875	High Similarity	NPC19174
0.875	High Similarity	NPC474417
0.875	High Similarity	NPC226275
0.8741	High Similarity	NPC65589
0.8741	High Similarity	NPC158338
0.8741	High Similarity	NPC97028
0.8741	High Similarity	NPC475088
0.8741	High Similarity	NPC288036
0.8741	High Similarity	NPC100985
0.8741	High Similarity	NPC50924
0.8741	High Similarity	NPC474394
0.8741	High Similarity	NPC97029
0.874	High Similarity	NPC294037
0.8731	High Similarity	NPC70622
0.8731	High Similarity	NPC478190
0.873	High Similarity	NPC40649
0.873	High Similarity	NPC209486
0.8722	High Similarity	NPC247477
0.8722	High Similarity	NPC31799
0.8722	High Similarity	NPC233056
0.8722	High Similarity	NPC17840
0.8712	High Similarity	NPC179898
0.8712	High Similarity	NPC48248
0.8705	High Similarity	NPC275734
0.8696	High Similarity	NPC472903
0.8692	High Similarity	NPC199273
0.8692	High Similarity	NPC142956
0.869	High Similarity	NPC154683
0.869	High Similarity	NPC40356
0.8686	High Similarity	NPC471452
0.8686	High Similarity	NPC44960
0.8686	High Similarity	NPC474110
0.8682	High Similarity	NPC309765
0.8681	High Similarity	NPC202595
0.8681	High Similarity	NPC325983
0.8681	High Similarity	NPC280295

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 NPC267205 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	388
0.1-0.2	985
0.2-0.3	1511
0.3-0.4	2905
0.4-0.5	1940
0.5-0.6	999
0.6-0.7	307
0.7-0.8	99
0.8-0.85	10
0.85-0.9	4
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9767	High Similarity	NPD1509	Clinical (unspecified phase)
0.9197	High Similarity	NPD7390	Discontinued
0.8898	High Similarity	NPD1201	Approved
0.8769	High Similarity	NPD1470	Approved
0.8593	High Similarity	NPD943	Approved
0.8551	High Similarity	NPD5405	Approved
0.8551	High Similarity	NPD5404	Approved
0.8551	High Similarity	NPD5406	Approved
0.8551	High Similarity	NPD5408	Approved
0.8333	Intermediate Similarity	NPD1607	Approved
0.8214	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.8214	Intermediate Similarity	NPD1510	Phase 2
0.8188	Intermediate Similarity	NPD1240	Approved
0.817	Intermediate Similarity	NPD6959	Discontinued
0.8169	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8117	Intermediate Similarity	NPD6232	Discontinued
0.8082	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8077	Intermediate Similarity	NPD7473	Discontinued
0.8013	Intermediate Similarity	NPD7819	Suspended
0.7972	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7972	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7959	Intermediate Similarity	NPD2532	Approved
0.7959	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7959	Intermediate Similarity	NPD2533	Approved
0.7959	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7959	Intermediate Similarity	NPD2534	Approved
0.7941	Intermediate Similarity	NPD1164	Approved
0.7917	Intermediate Similarity	NPD1549	Phase 2
0.7895	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7891	Intermediate Similarity	NPD1511	Approved
0.7863	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7843	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7785	Intermediate Similarity	NPD1512	Approved
0.7748	Intermediate Similarity	NPD3226	Approved
0.7712	Intermediate Similarity	NPD1934	Approved
0.7697	Intermediate Similarity	NPD4380	Phase 2
0.7687	Intermediate Similarity	NPD3750	Approved
0.7655	Intermediate Similarity	NPD2935	Discontinued
0.7647	Intermediate Similarity	NPD7411	Suspended
0.763	Intermediate Similarity	NPD3019	Approved
0.7628	Intermediate Similarity	NPD3749	Approved
0.7619	Intermediate Similarity	NPD2800	Approved
0.7603	Intermediate Similarity	NPD2346	Discontinued
0.7556	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7548	Intermediate Similarity	NPD2801	Approved
0.7534	Intermediate Similarity	NPD6100	Approved
0.7534	Intermediate Similarity	NPD2796	Approved
0.7534	Intermediate Similarity	NPD6099	Approved
0.7516	Intermediate Similarity	NPD7075	Discontinued
0.75	Intermediate Similarity	NPD2932	Approved
0.7467	Intermediate Similarity	NPD3300	Phase 2
0.7464	Intermediate Similarity	NPD9269	Phase 2
0.7462	Intermediate Similarity	NPD4750	Phase 3
0.7453	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7452	Intermediate Similarity	NPD7768	Phase 2
0.7448	Intermediate Similarity	NPD6651	Approved
0.7436	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7426	Intermediate Similarity	NPD9268	Approved
0.7423	Intermediate Similarity	NPD6020	Phase 2
0.7423	Intermediate Similarity	NPD5844	Phase 1
0.7415	Intermediate Similarity	NPD1551	Phase 2
0.7413	Intermediate Similarity	NPD3764	Approved
0.7383	Intermediate Similarity	NPD1243	Approved
0.7355	Intermediate Similarity	NPD6599	Discontinued
0.7347	Intermediate Similarity	NPD3748	Approved
0.7347	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.7346	Intermediate Similarity	NPD6166	Phase 2
0.7346	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7346	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7342	Intermediate Similarity	NPD3882	Suspended
0.7329	Intermediate Similarity	NPD5711	Approved
0.7329	Intermediate Similarity	NPD5710	Approved
0.7308	Intermediate Similarity	NPD2342	Discontinued
0.7267	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7261	Intermediate Similarity	NPD6801	Discontinued
0.726	Intermediate Similarity	NPD230	Phase 1
0.7252	Intermediate Similarity	NPD74	Approved
0.7252	Intermediate Similarity	NPD9266	Approved
0.7248	Intermediate Similarity	NPD2344	Approved
0.7244	Intermediate Similarity	NPD1242	Phase 1
0.7234	Intermediate Similarity	NPD1283	Approved
0.723	Intermediate Similarity	NPD2799	Discontinued
0.7222	Intermediate Similarity	NPD4625	Phase 3
0.7219	Intermediate Similarity	NPD7003	Approved
0.7219	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD1465	Phase 2
0.7206	Intermediate Similarity	NPD9493	Approved
0.7205	Intermediate Similarity	NPD5494	Approved
0.7194	Intermediate Similarity	NPD3026	Approved
0.7194	Intermediate Similarity	NPD3023	Approved
0.719	Intermediate Similarity	NPD6799	Approved
0.7188	Intermediate Similarity	NPD940	Approved
0.7188	Intermediate Similarity	NPD846	Approved
0.7188	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7186	Intermediate Similarity	NPD6559	Discontinued
0.7185	Intermediate Similarity	NPD5951	Approved
0.7176	Intermediate Similarity	NPD9267	Approved
0.7176	Intermediate Similarity	NPD9264	Approved
0.7176	Intermediate Similarity	NPD9263	Approved
0.7176	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7174	Intermediate Similarity	NPD3025	Approved
0.7174	Intermediate Similarity	NPD1651	Approved
0.7174	Intermediate Similarity	NPD3024	Approved
0.717	Intermediate Similarity	NPD3817	Phase 2
0.7133	Intermediate Similarity	NPD2798	Approved
0.7125	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.711	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7076	Intermediate Similarity	NPD8150	Discontinued
0.707	Intermediate Similarity	NPD7458	Discontinued
0.707	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7066	Intermediate Similarity	NPD7074	Phase 3
0.7063	Intermediate Similarity	NPD1203	Approved
0.7059	Intermediate Similarity	NPD2309	Approved
0.7055	Intermediate Similarity	NPD2313	Discontinued
0.7051	Intermediate Similarity	NPD920	Approved
0.7048	Intermediate Similarity	NPD3818	Discontinued
0.7041	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD7635	Approved
0.7021	Intermediate Similarity	NPD1281	Approved
0.702	Intermediate Similarity	NPD1471	Phase 3
0.7013	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD7054	Approved
0.6978	Remote Similarity	NPD9545	Approved
0.6972	Remote Similarity	NPD3972	Approved
0.6964	Remote Similarity	NPD7472	Approved
0.6957	Remote Similarity	NPD8438	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD411	Approved
0.6937	Remote Similarity	NPD37	Approved
0.6934	Remote Similarity	NPD9281	Approved
0.6933	Remote Similarity	NPD919	Approved
0.6932	Remote Similarity	NPD6535	Approved
0.6932	Remote Similarity	NPD6534	Approved
0.6923	Remote Similarity	NPD6797	Phase 2
0.6923	Remote Similarity	NPD5953	Discontinued
0.6923	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6892	Remote Similarity	NPD6663	Approved
0.6887	Remote Similarity	NPD4308	Phase 3
0.6883	Remote Similarity	NPD4628	Phase 3
0.6882	Remote Similarity	NPD7251	Discontinued
0.6879	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD4626	Approved
0.6879	Remote Similarity	NPD2286	Discontinued
0.6875	Remote Similarity	NPD288	Approved
0.687	Remote Similarity	NPD9261	Approved
0.6853	Remote Similarity	NPD9717	Approved
0.6853	Remote Similarity	NPD1608	Approved
0.6849	Remote Similarity	NPD5736	Approved
0.6848	Remote Similarity	NPD1247	Approved
0.6842	Remote Similarity	NPD7808	Phase 3
0.6833	Remote Similarity	NPD6781	Approved
0.6833	Remote Similarity	NPD6778	Approved
0.6833	Remote Similarity	NPD6782	Approved
0.6833	Remote Similarity	NPD6777	Approved
0.6833	Remote Similarity	NPD6776	Approved
0.6833	Remote Similarity	NPD6780	Approved
0.6833	Remote Similarity	NPD6779	Approved
0.6833	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD6234	Discontinued
0.6824	Remote Similarity	NPD3268	Approved
0.6818	Remote Similarity	NPD2654	Approved
0.6816	Remote Similarity	NPD7700	Phase 2
0.6816	Remote Similarity	NPD7699	Phase 2
0.6815	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6811	Remote Similarity	NPD8151	Discontinued
0.681	Remote Similarity	NPD4965	Approved
0.681	Remote Similarity	NPD4966	Approved
0.681	Remote Similarity	NPD4967	Phase 2
0.6807	Remote Similarity	NPD7229	Phase 3
0.6806	Remote Similarity	NPD4749	Approved
0.6805	Remote Similarity	NPD7286	Phase 2
0.6803	Remote Similarity	NPD4908	Phase 1
0.6802	Remote Similarity	NPD8312	Approved
0.6802	Remote Similarity	NPD8313	Approved
0.6797	Remote Similarity	NPD844	Approved
0.6783	Remote Similarity	NPD1610	Phase 2
0.6783	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD8166	Discontinued
0.6769	Remote Similarity	NPD3020	Approved
0.6766	Remote Similarity	NPD3926	Phase 2
0.6759	Remote Similarity	NPD1876	Approved
0.6748	Remote Similarity	NPD4288	Approved
0.6748	Remote Similarity	NPD5402	Approved
0.6746	Remote Similarity	NPD7177	Discontinued
0.6744	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6738	Remote Similarity	NPD3091	Approved
0.6735	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.673	Remote Similarity	NPD5403	Approved
0.6725	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6721	Remote Similarity	NPD7435	Discontinued
0.6721	Remote Similarity	NPD7696	Phase 3
0.6721	Remote Similarity	NPD7697	Approved
0.6721	Remote Similarity	NPD7698	Approved
0.6712	Remote Similarity	NPD2797	Approved
0.6712	Remote Similarity	NPD3094	Phase 2

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