NPASS Compound

Structure

CID175738 OpenBabel06191715552D 29 31 0 0 1 0 0 0 0 0999 V2000 -0.8390 4.3594 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 2.9063 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3558 2.9063 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3558 -2.9062 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5169 -2.4219 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1948 -2.4219 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5169 -1.4531 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1948 -1.4531 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6779 2.9063 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1948 1.4531 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6779 1.9375 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1948 0.4844 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6779 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8390 1.4531 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8390 3.3906 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3558 1.9375 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3558 -0.9687 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6779 0.9687 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5169 1.4531 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.3558 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8390 -0.4844 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.9688 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5169 0.4844 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8390 -0.4844 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5169 1.4531 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8390 -1.4531 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8390 1.4531 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8390 -1.4531 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 15 1 0 0 0 0 2 15 1 0 0 0 0 3 16 1 0 0 0 0 4 5 2 0 0 0 0 4 6 1 0 0 0 0 5 7 1 0 0 0 0 6 8 2 0 0 0 0 7 17 2 0 0 0 0 8 17 1 0 0 0 0 9 11 1 0 0 0 0 9 15 2 0 0 0 0 10 12 1 0 0 0 0 10 16 2 0 0 0 0 12 20 1 0 0 0 0 13 18 2 0 0 0 0 13 21 1 0 0 0 0 14 18 1 0 0 0 0 14 22 2 0 0 0 0 16 19 1 0 0 0 0 18 26 1 0 0 0 0 19 11 1 1 0 0 0 19 23 1 0 0 0 0 20 17 1 6 0 0 0 20 23 1 0 0 0 0 21 24 2 0 0 0 0 21 27 1 0 0 0 0 22 24 1 0 0 0 0 22 28 1 0 0 0 0 23 25 1 1 0 0 0 24 25 1 0 0 0 0 25 29 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	392.2
Volume:	426.719
LogP:	6.604
LogD:	4.214
LogS:	-3.047
# Rotatable Bonds:	5
TPSA:	77.76
# H-Bond Aceptor:	4
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.45
Synthetic Accessibility Score:	3.878
Fsp3:	0.32
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.808
MDCK Permeability:	1.61556490638759e-05
Pgp-inhibitor:	0.412
Pgp-substrate:	0.014
Human Intestinal Absorption (HIA):	0.011
20% Bioavailability (F20%):	0.946
30% Bioavailability (F30%):	0.989

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.011
Plasma Protein Binding (PPB):	99.96707916259766%
Volume Distribution (VD):	2.484
Pgp-substrate:	1.2776591777801514%

ADMET: Metabolism

CYP1A2-inhibitor:	0.922
CYP1A2-substrate:	0.407
CYP2C19-inhibitor:	0.957
CYP2C19-substrate:	0.072
CYP2C9-inhibitor:	0.937
CYP2C9-substrate:	0.945
CYP2D6-inhibitor:	0.955
CYP2D6-substrate:	0.225
CYP3A4-inhibitor:	0.822
CYP3A4-substrate:	0.166

ADMET: Excretion

Clearance (CL):	14.718
Half-life (T1/2):	0.145

ADMET: Toxicity

hERG Blockers:	0.214
Human Hepatotoxicity (H-HT):	0.448
Drug-inuced Liver Injury (DILI):	0.557
AMES Toxicity:	0.101
Rat Oral Acute Toxicity:	0.178
Maximum Recommended Daily Dose:	0.887
Skin Sensitization:	0.838
Carcinogencity:	0.183
Eye Corrosion:	0.004
Eye Irritation:	0.703
Respiratory Toxicity:	0.774

Download Data

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

Natural Product: NPC175738

Natural Product ID:	NPC175738
*Common Name:**	4-Hydroxypanduratin A
IUPAC Name:	[(1R,2S,6R)-3-methyl-2-(3-methylbut-2-enyl)-6-phenylcyclohex-3-en-1-yl]-(2,4,6-trihydroxyphenyl)methanone
Synonyms:
Standard InCHIKey:	AYPOOQWQTQIRFW-ZRCGQRJVSA-N
Standard InCHI:	InChI=1S/C25H28O4/c1-15(2)9-11-19-16(3)10-12-20(17-7-5-4-6-8-17)23(19)25(29)24-21(27)13-18(26)14-22(24)28/h4-10,13-14,19-20,23,26-28H,11-12H2,1-3H3/t19-,20+,23-/m1/s1
SMILES:	CC(=CC[C@@H]1C(=CC[C@H]([C@@H]1C(=O)c1c(O)cc(cc1O)O)c1ccccc1)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL210882
PubChem CID:	636530
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002650] Diarylheptanoids [CHEMONTID:0002651] Linear diarylheptanoids

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

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO1373	Pulsatilla chinensis	Species	Ranunculaceae	Eukaryota	roots	n.a.	n.a.	PMID[10514313]
NPO1373	Pulsatilla chinensis	Species	Ranunculaceae	Eukaryota	n.a.	root	n.a.	PMID[10514313]
NPO27986	Lonchocarpus chiricanus	Species	Fabaceae	Eukaryota	Root barks	n.a.	n.a.	PMID[11421729]
NPO1373	Pulsatilla chinensis	Species	Ranunculaceae	Eukaryota	roots	n.a.	n.a.	PMID[11575962]
NPO24946	Kaempferia pandurata	Species	Zingiberaceae	Eukaryota	n.a.	rhizome	n.a.	PMID[15930750]
NPO27695	Centaurea sonchifolia	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[1624943]
NPO27600	Boesenbergia pandurata	Species	Zingiberaceae	Eukaryota	rhizomes	Pindaya Township, Shan State, Myanmar	2004-NOV	PMID[17896818]
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]
NPO19745	Esox lucius	Species	Esocidae	Eukaryota	n.a.	n.a.	n.a.	PMID[3349210]
NPO28159	Rubia akane	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8176404]
NPO19745	Esox lucius	Species	Esocidae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO19745	Esox lucius	Species	Esocidae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO1373	Pulsatilla chinensis	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24946	Kaempferia pandurata	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1373	Pulsatilla chinensis	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23156	Maclura cochinchinensis	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27397	Drymaria cordata	Species	Caryophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27882	Boswellia ovalifoliolata	Species	Burseraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24946	Kaempferia pandurata	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1373	Pulsatilla chinensis	Species	Ranunculaceae	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]
NPO27986	Lonchocarpus chiricanus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27882	Boswellia ovalifoliolata	Species	Burseraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26553	Lemonia spectabilis	Species	Lemoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28063	Beilschmiedia madang	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27338	Senecio platyphylloides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26321	Salvia patens	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27613	Helleborus macranthus	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27637	Heliotropium scabrum	Species	Heliotropiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27816	Pterocaulon serrulatum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28003	Astragalus circassicus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8961	Bethencourtia palmensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17337	Centaurea scoparia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19383	Lactarius mitissimus	Species	Russulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27397	Drymaria cordata	Species	Caryophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10367	Gaillardia coahuilensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28313	Mentzelia decapetala	Species	Loasaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2030	Mimosa pigra	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28426	Etmopterus spinax	Species	Etmopteridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26342	Dialium excelsum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16298	Quercus marilandica	Species	Fagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27702	Matricaria sabulosa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28206	Aniba santalodora	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25499	Campanula choziatowskyi	Species	Campanulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28412	Amorphophallus konjac	Species	Araceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25835	Parmotrema nilgherrense	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9354	Lepechinia urbanii	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28083	Salvia lavanduloides	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28044	Erythrina hypaphorus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19745	Esox lucius	Species	Esocidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27695	Centaurea sonchifolia	Species	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO23156	Maclura cochinchinensis	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16156	Mucuna holtonii	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1373	Pulsatilla chinensis	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24946	Kaempferia pandurata	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1184	Colchicum filifolium	Species	Colchicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5970.1	Petunia axillaris subsp. parodii	Subspecies	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27854	Sphaeria rousseliana	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO27642	Podocarpus dacrydioides	Species	Podocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11849	Cynoglossum macrostylum	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27506	Orgyia pseudotsugata	Species	Lymantriidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27600	Boesenbergia pandurata	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4164	Salvia virgata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27057	Matsucoccus josephi	Species	Margarodidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8738	Xylopia emarginata	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28159	Rubia akane	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27145	Euphorbia hylonoma	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27614	Salix rosmarinifolia	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28385	Iris kashmiriana	Species	Tarachodidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28289	Nepytia freemani	Species	Geometridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27916	Hardenbergia violacea	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27455	Dysidea fragilis	Species	Dysideidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26476	Preussia terricola	Species	Sporormiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27234	Thalassiosira weissflogii	Species	Thalassiosiraceae	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
Ki	1
Others	11

Activity Type	# Activity
Cell Line	2
Individual Protein	10

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT461	Cell Line	PANC-1	Homo sapiens	PC100	=	16.0	uM	PMID[493433]
NPT461	Cell Line	PANC-1	Homo sapiens	PC50	=	3.1	uM	PMID[493434]
NPT917	Individual Protein	Dengue virus type 2 NS3 protein	Dengue virus type 2 (strain Thailand/16681/1984) (DENV-2)	Inhibition	=	78.1	%	PMID[493432]
NPT917	Individual Protein	Dengue virus type 2 NS3 protein	Dengue virus type 2 (strain Thailand/16681/1984) (DENV-2)	Inhibition	=	52.0	%	PMID[493432]
NPT917	Individual Protein	Dengue virus type 2 NS3 protein	Dengue virus type 2 (strain Thailand/16681/1984) (DENV-2)	Inhibition	=	87.6	%	PMID[493432]
NPT917	Individual Protein	Dengue virus type 2 NS3 protein	Dengue virus type 2 (strain Thailand/16681/1984) (DENV-2)	Inhibition	=	96.0	%	PMID[493432]
NPT917	Individual Protein	Dengue virus type 2 NS3 protein	Dengue virus type 2 (strain Thailand/16681/1984) (DENV-2)	Inhibition	=	97.3	%	PMID[493432]
NPT917	Individual Protein	Dengue virus type 2 NS3 protein	Dengue virus type 2 (strain Thailand/16681/1984) (DENV-2)	Inhibition	=	99.8	%	PMID[493432]
NPT917	Individual Protein	Dengue virus type 2 NS3 protein	Dengue virus type 2 (strain Thailand/16681/1984) (DENV-2)	Inhibition	=	96.1	%	PMID[493432]
NPT917	Individual Protein	Dengue virus type 2 NS3 protein	Dengue virus type 2 (strain Thailand/16681/1984) (DENV-2)	Inhibition	=	99.2	%	PMID[493432]
NPT917	Individual Protein	Dengue virus type 2 NS3 protein	Dengue virus type 2 (strain Thailand/16681/1984) (DENV-2)	Inhibition	=	90.4	%	PMID[493432]
NPT917	Individual Protein	Dengue virus type 2 NS3 protein	Dengue virus type 2 (strain Thailand/16681/1984) (DENV-2)	Ki	=	21000.0	nM	PMID[493432]

☑ 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 NPC175738 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	328
0.1-0.2	1467
0.2-0.3	3346
0.3-0.4	9496
0.4-0.5	9838
0.5-0.6	4734
0.6-0.7	7114
0.7-0.8	4965
0.8-0.85	1044
0.85-0.9	287
0.9-0.95	77
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9385	High Similarity	NPC475088
0.937	High Similarity	NPC473017
0.9365	High Similarity	NPC267846
0.9297	High Similarity	NPC92624
0.9297	High Similarity	NPC474998
0.9291	High Similarity	NPC30501
0.9291	High Similarity	NPC103356
0.9291	High Similarity	NPC105157
0.9291	High Similarity	NPC100067
0.9291	High Similarity	NPC72158
0.9291	High Similarity	NPC23126
0.9291	High Similarity	NPC98254
0.9291	High Similarity	NPC169250
0.9291	High Similarity	NPC266689
0.9291	High Similarity	NPC162612
0.9291	High Similarity	NPC116513
0.9291	High Similarity	NPC190043
0.9259	High Similarity	NPC40118
0.9259	High Similarity	NPC126534
0.9259	High Similarity	NPC232021
0.9254	High Similarity	NPC169452
0.9254	High Similarity	NPC181560
0.9242	High Similarity	NPC191976
0.9237	High Similarity	NPC282780
0.9237	High Similarity	NPC166480
0.9225	High Similarity	NPC259942
0.9219	High Similarity	NPC21305
0.9219	High Similarity	NPC221777
0.9213	High Similarity	NPC62952
0.9185	High Similarity	NPC265178
0.9179	High Similarity	NPC242994
0.9179	High Similarity	NPC138099
0.916	High Similarity	NPC267205
0.9147	High Similarity	NPC109123
0.9134	High Similarity	NPC475733
0.9127	High Similarity	NPC472029
0.9127	High Similarity	NPC65761
0.912	High Similarity	NPC196976
0.912	High Similarity	NPC242895
0.9118	High Similarity	NPC193555
0.9104	High Similarity	NPC473622
0.9098	High Similarity	NPC118919
0.9091	High Similarity	NPC44437
0.9051	High Similarity	NPC474203
0.9051	High Similarity	NPC313047
0.9051	High Similarity	NPC451542
0.9051	High Similarity	NPC297600
0.9051	High Similarity	NPC295712
0.9048	High Similarity	NPC133909
0.9048	High Similarity	NPC91105
0.9048	High Similarity	NPC32032
0.904	High Similarity	NPC146642
0.904	High Similarity	NPC149246
0.903	High Similarity	NPC471905
0.903	High Similarity	NPC53206
0.903	High Similarity	NPC53001
0.903	High Similarity	NPC53414
0.9023	High Similarity	NPC290803
0.9015	High Similarity	NPC40524
0.9015	High Similarity	NPC139074
0.9015	High Similarity	NPC213485
0.9008	High Similarity	NPC475042
0.8984	High Similarity	NPC477454
0.8968	High Similarity	NPC143427
0.8968	High Similarity	NPC19174
0.8968	High Similarity	NPC73532
0.8968	High Similarity	NPC267552
0.8968	High Similarity	NPC115159
0.8968	High Similarity	NPC156139
0.8968	High Similarity	NPC45438
0.8968	High Similarity	NPC215392
0.8968	High Similarity	NPC224273
0.8963	High Similarity	NPC87723
0.896	High Similarity	NPC294037
0.8955	High Similarity	NPC254847
0.8947	High Similarity	NPC12070
0.8915	High Similarity	NPC473691
0.8915	High Similarity	NPC8745
0.8913	High Similarity	NPC293545
0.8913	High Similarity	NPC174905
0.8906	High Similarity	NPC13238
0.8898	High Similarity	NPC309765
0.8889	High Similarity	NPC213603
0.8889	High Similarity	NPC44960
0.8889	High Similarity	NPC297186
0.8889	High Similarity	NPC290030
0.8889	High Similarity	NPC474110
0.8881	High Similarity	NPC130899
0.8881	High Similarity	NPC61153
0.8881	High Similarity	NPC249272
0.8881	High Similarity	NPC283590
0.8881	High Similarity	NPC70859
0.888	High Similarity	NPC188814
0.888	High Similarity	NPC195262
0.8872	High Similarity	NPC114183
0.8864	High Similarity	NPC275504
0.8857	High Similarity	NPC85393
0.8857	High Similarity	NPC271944
0.8857	High Similarity	NPC110882
0.8855	High Similarity	NPC476119
0.8841	High Similarity	NPC474961
0.8841	High Similarity	NPC135524
0.8837	High Similarity	NPC10926
0.8832	High Similarity	NPC470986
0.8819	High Similarity	NPC303737
0.8815	High Similarity	NPC65005
0.8815	High Similarity	NPC194764
0.8815	High Similarity	NPC264112
0.881	High Similarity	NPC159525
0.8806	High Similarity	NPC270899
0.88	High Similarity	NPC40649
0.88	High Similarity	NPC209486
0.8788	High Similarity	NPC17840
0.8788	High Similarity	NPC247477
0.8768	High Similarity	NPC204045
0.8768	High Similarity	NPC110810
0.8768	High Similarity	NPC246638
0.8768	High Similarity	NPC305845
0.8759	High Similarity	NPC472368
0.8759	High Similarity	NPC162939
0.8759	High Similarity	NPC143438
0.8759	High Similarity	NPC472903
0.8741	High Similarity	NPC470210
0.874	High Similarity	NPC229649
0.8731	High Similarity	NPC180261
0.8731	High Similarity	NPC37299
0.873	High Similarity	NPC161617
0.873	High Similarity	NPC158222
0.872	High Similarity	NPC121259
0.8714	High Similarity	NPC193703
0.8714	High Similarity	NPC21599
0.8714	High Similarity	NPC227841
0.8705	High Similarity	NPC137649
0.8696	High Similarity	NPC477956
0.8696	High Similarity	NPC109232
0.8696	High Similarity	NPC472366
0.8696	High Similarity	NPC203063
0.8686	High Similarity	NPC153979
0.8676	High Similarity	NPC13575
0.8676	High Similarity	NPC131039
0.8672	High Similarity	NPC226275
0.8671	High Similarity	NPC329933
0.8667	High Similarity	NPC28753
0.8667	High Similarity	NPC204960
0.8667	High Similarity	NPC294593
0.8667	High Similarity	NPC159623
0.8667	High Similarity	NPC18877
0.8667	High Similarity	NPC82225
0.8667	High Similarity	NPC20560
0.8667	High Similarity	NPC144051
0.8652	High Similarity	NPC12402
0.8652	High Similarity	NPC34482
0.8652	High Similarity	NPC271288
0.8647	High Similarity	NPC233056
0.8647	High Similarity	NPC244441
0.8643	High Similarity	NPC296752
0.8636	High Similarity	NPC96024
0.8633	High Similarity	NPC213659
0.8633	High Similarity	NPC172250
0.8633	High Similarity	NPC259166
0.8633	High Similarity	NPC80962
0.8633	High Similarity	NPC144118
0.8633	High Similarity	NPC187843
0.8633	High Similarity	NPC472904
0.8633	High Similarity	NPC219917
0.8633	High Similarity	NPC48624
0.8633	High Similarity	NPC215311
0.8633	High Similarity	NPC326109
0.8633	High Similarity	NPC204985
0.8633	High Similarity	NPC11056
0.8626	High Similarity	NPC3224
0.8626	High Similarity	NPC328983
0.8626	High Similarity	NPC160499
0.8623	High Similarity	NPC190457
0.8623	High Similarity	NPC21350
0.8623	High Similarity	NPC19622
0.8623	High Similarity	NPC112789
0.8623	High Similarity	NPC251681
0.8623	High Similarity	NPC243528
0.8615	High Similarity	NPC199273
0.8613	High Similarity	NPC477243
0.8613	High Similarity	NPC472367
0.8613	High Similarity	NPC168105
0.8613	High Similarity	NPC150399
0.8613	High Similarity	NPC186838
0.8613	High Similarity	NPC477244
0.8613	High Similarity	NPC98115
0.8613	High Similarity	NPC249606
0.8613	High Similarity	NPC274109
0.8613	High Similarity	NPC477242
0.8613	High Similarity	NPC12165
0.8613	High Similarity	NPC24394
0.8613	High Similarity	NPC41461
0.8613	High Similarity	NPC476333
0.8613	High Similarity	NPC1486
0.8613	High Similarity	NPC25287
0.8613	High Similarity	NPC66349
0.8605	High Similarity	NPC232708
0.8603	High Similarity	NPC286336
0.8603	High Similarity	NPC103842

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 NPC175738 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	316
0.1-0.2	927
0.2-0.3	1298
0.3-0.4	2689
0.4-0.5	2216
0.5-0.6	1198
0.6-0.7	377
0.7-0.8	115
0.8-0.85	11
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8955	High Similarity	NPD1509	Clinical (unspecified phase)
0.8714	High Similarity	NPD7390	Discontinued
0.8527	High Similarity	NPD1201	Approved
0.8519	High Similarity	NPD943	Approved
0.8409	Intermediate Similarity	NPD1470	Approved
0.8406	Intermediate Similarity	NPD1510	Phase 2
0.8394	Intermediate Similarity	NPD1607	Approved
0.8392	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8382	Intermediate Similarity	NPD1240	Approved
0.8214	Intermediate Similarity	NPD5404	Approved
0.8214	Intermediate Similarity	NPD5408	Approved
0.8214	Intermediate Similarity	NPD5406	Approved
0.8214	Intermediate Similarity	NPD5405	Approved
0.8156	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8156	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8138	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8133	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8099	Intermediate Similarity	NPD1549	Phase 2
0.8014	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD1164	Approved
0.7987	Intermediate Similarity	NPD4380	Phase 2
0.7986	Intermediate Similarity	NPD3750	Approved
0.7972	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7958	Intermediate Similarity	NPD2796	Approved
0.7947	Intermediate Similarity	NPD7819	Suspended
0.7947	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7898	Intermediate Similarity	NPD7473	Discontinued
0.7872	Intermediate Similarity	NPD6651	Approved
0.7823	Intermediate Similarity	NPD1511	Approved
0.7821	Intermediate Similarity	NPD6232	Discontinued
0.782	Intermediate Similarity	NPD2932	Approved
0.7815	Intermediate Similarity	NPD7411	Suspended
0.7793	Intermediate Similarity	NPD2800	Approved
0.7792	Intermediate Similarity	NPD7075	Discontinued
0.7786	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7763	Intermediate Similarity	NPD1934	Approved
0.7756	Intermediate Similarity	NPD6959	Discontinued
0.7755	Intermediate Similarity	NPD3300	Phase 2
0.7744	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7718	Intermediate Similarity	NPD1512	Approved
0.7712	Intermediate Similarity	NPD2801	Approved
0.7712	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7708	Intermediate Similarity	NPD2935	Discontinued
0.7687	Intermediate Similarity	NPD3019	Approved
0.7681	Intermediate Similarity	NPD2798	Approved
0.7677	Intermediate Similarity	NPD3749	Approved
0.7656	Intermediate Similarity	NPD4750	Phase 3
0.7651	Intermediate Similarity	NPD2534	Approved
0.7651	Intermediate Similarity	NPD2532	Approved
0.7651	Intermediate Similarity	NPD2533	Approved
0.7651	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7639	Intermediate Similarity	NPD3748	Approved
0.7639	Intermediate Similarity	NPD2799	Discontinued
0.7632	Intermediate Similarity	NPD6599	Discontinued
0.7613	Intermediate Similarity	NPD7768	Phase 2
0.761	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD6100	Approved
0.7586	Intermediate Similarity	NPD6099	Approved
0.7584	Intermediate Similarity	NPD6799	Approved
0.7578	Intermediate Similarity	NPD6020	Phase 2
0.7564	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7534	Intermediate Similarity	NPD2344	Approved
0.7532	Intermediate Similarity	NPD6801	Discontinued
0.752	Intermediate Similarity	NPD846	Approved
0.752	Intermediate Similarity	NPD940	Approved
0.7517	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD3882	Suspended
0.7466	Intermediate Similarity	NPD1551	Phase 2
0.7465	Intermediate Similarity	NPD3764	Approved
0.7442	Intermediate Similarity	NPD74	Approved
0.7442	Intermediate Similarity	NPD9266	Approved
0.7432	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD6166	Phase 2
0.7388	Intermediate Similarity	NPD9493	Approved
0.7383	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7383	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7364	Intermediate Similarity	NPD9267	Approved
0.7364	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7364	Intermediate Similarity	NPD9264	Approved
0.7364	Intermediate Similarity	NPD9263	Approved
0.7362	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.736	Intermediate Similarity	NPD3020	Approved
0.7358	Intermediate Similarity	NPD5494	Approved
0.7343	Intermediate Similarity	NPD3268	Approved
0.7343	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD3226	Approved
0.7333	Intermediate Similarity	NPD2309	Approved
0.7325	Intermediate Similarity	NPD3817	Phase 2
0.7315	Intermediate Similarity	NPD1243	Approved
0.7297	Intermediate Similarity	NPD2346	Discontinued
0.7267	Intermediate Similarity	NPD7003	Approved
0.7266	Intermediate Similarity	NPD3972	Approved
0.7266	Intermediate Similarity	NPD9269	Phase 2
0.7246	Intermediate Similarity	NPD3023	Approved
0.7246	Intermediate Similarity	NPD3026	Approved
0.7234	Intermediate Similarity	NPD1203	Approved
0.7234	Intermediate Similarity	NPD2797	Approved
0.7226	Intermediate Similarity	NPD3025	Approved
0.7226	Intermediate Similarity	NPD9268	Approved
0.7226	Intermediate Similarity	NPD7458	Discontinued
0.7226	Intermediate Similarity	NPD3024	Approved
0.7222	Intermediate Similarity	NPD2313	Discontinued
0.7222	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD7074	Phase 3
0.7203	Intermediate Similarity	NPD4908	Phase 1
0.7195	Intermediate Similarity	NPD3818	Discontinued
0.7169	Intermediate Similarity	NPD5953	Discontinued
0.7165	Intermediate Similarity	NPD1242	Phase 1
0.7153	Intermediate Similarity	NPD9545	Approved
0.7152	Intermediate Similarity	NPD5844	Phase 1
0.7152	Intermediate Similarity	NPD4628	Phase 3
0.7152	Intermediate Similarity	NPD7054	Approved
0.7126	Intermediate Similarity	NPD6559	Discontinued
0.712	Intermediate Similarity	NPD2859	Approved
0.712	Intermediate Similarity	NPD2860	Approved
0.7111	Intermediate Similarity	NPD9281	Approved
0.7111	Intermediate Similarity	NPD5951	Approved
0.7108	Intermediate Similarity	NPD7472	Approved
0.7107	Intermediate Similarity	NPD8438	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD5403	Approved
0.7097	Intermediate Similarity	NPD920	Approved
0.7086	Intermediate Similarity	NPD2654	Approved
0.7075	Intermediate Similarity	NPD230	Phase 1
0.7071	Intermediate Similarity	NPD1610	Phase 2
0.7066	Intermediate Similarity	NPD6797	Phase 2
0.7063	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD5710	Approved
0.7055	Intermediate Similarity	NPD5711	Approved
0.7054	Intermediate Similarity	NPD9261	Approved
0.7048	Intermediate Similarity	NPD7286	Phase 2
0.7047	Intermediate Similarity	NPD4308	Phase 3
0.7042	Intermediate Similarity	NPD1876	Approved
0.704	Intermediate Similarity	NPD2934	Approved
0.704	Intermediate Similarity	NPD2933	Approved
0.7039	Intermediate Similarity	NPD8166	Discontinued
0.7034	Intermediate Similarity	NPD4625	Phase 3
0.7024	Intermediate Similarity	NPD7251	Discontinued
0.7021	Intermediate Similarity	NPD4878	Approved
0.7021	Intermediate Similarity	NPD9717	Approved
0.7018	Intermediate Similarity	NPD8150	Discontinued
0.7	Intermediate Similarity	NPD4288	Approved
0.6993	Remote Similarity	NPD3267	Approved
0.6993	Remote Similarity	NPD3266	Approved
0.6992	Remote Similarity	NPD3022	Approved
0.6992	Remote Similarity	NPD3021	Approved
0.6987	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6982	Remote Similarity	NPD7808	Phase 3
0.6972	Remote Similarity	NPD4749	Approved
0.6971	Remote Similarity	NPD4363	Phase 3
0.6971	Remote Similarity	NPD4360	Phase 2
0.6968	Remote Similarity	NPD5401	Approved
0.6968	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD6832	Phase 2
0.6963	Remote Similarity	NPD7635	Approved
0.6954	Remote Similarity	NPD1471	Phase 3
0.695	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD6663	Approved
0.6937	Remote Similarity	NPD1465	Phase 2
0.6932	Remote Similarity	NPD4362	Clinical (unspecified phase)
0.6932	Remote Similarity	NPD4361	Phase 2
0.6929	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD3400	Discontinued
0.6923	Remote Similarity	NPD1930	Approved
0.6923	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD1283	Approved
0.6923	Remote Similarity	NPD1929	Approved
0.6917	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD3926	Phase 2
0.6901	Remote Similarity	NPD1608	Approved
0.6899	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD5736	Approved
0.6894	Remote Similarity	NPD5402	Approved
0.6882	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD37	Approved
0.6859	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD1651	Approved
0.6857	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD2342	Discontinued
0.6831	Remote Similarity	NPD422	Phase 1
0.6828	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6825	Remote Similarity	NPD845	Approved
0.6824	Remote Similarity	NPD5027	Approved
0.6824	Remote Similarity	NPD5029	Approved
0.6824	Remote Similarity	NPD5031	Approved
0.6821	Remote Similarity	NPD7033	Discontinued
0.6809	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6797	Remote Similarity	NPD288	Approved
0.679	Remote Similarity	NPD2296	Approved
0.6786	Remote Similarity	NPD1548	Phase 1
0.6786	Remote Similarity	NPD3091	Approved
0.6784	Remote Similarity	NPD5026	Approved
0.6784	Remote Similarity	NPD4955	Approved
0.6784	Remote Similarity	NPD5028	Approved
0.6784	Remote Similarity	NPD4954	Approved
0.6784	Remote Similarity	NPD36	Approved
0.6784	Remote Similarity	NPD5034	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