NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	210.13
Volume:	220.093
LogP:	0.779
LogD:	0.565
LogS:	-3.371
# Rotatable Bonds:	0
TPSA:	57.53
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.631
Synthetic Accessibility Score:	4.196
Fsp3:	0.75
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:	-4.611
MDCK Permeability:	2.7116893761558458e-05
Pgp-inhibitor:	0.02
Pgp-substrate:	0.093
Human Intestinal Absorption (HIA):	0.01
20% Bioavailability (F20%):	0.009
30% Bioavailability (F30%):	0.01

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.912
Plasma Protein Binding (PPB):	72.35888671875%
Volume Distribution (VD):	0.694
Pgp-substrate:	38.319801330566406%

ADMET: Metabolism

CYP1A2-inhibitor:	0.009
CYP1A2-substrate:	0.785
CYP2C19-inhibitor:	0.026
CYP2C19-substrate:	0.745
CYP2C9-inhibitor:	0.029
CYP2C9-substrate:	0.444
CYP2D6-inhibitor:	0.002
CYP2D6-substrate:	0.107
CYP3A4-inhibitor:	0.024
CYP3A4-substrate:	0.225

ADMET: Excretion

Clearance (CL):	3.356
Half-life (T1/2):	0.859

ADMET: Toxicity

hERG Blockers:	0.034
Human Hepatotoxicity (H-HT):	0.296
Drug-inuced Liver Injury (DILI):	0.072
AMES Toxicity:	0.461
Rat Oral Acute Toxicity:	0.913
Maximum Recommended Daily Dose:	0.797
Skin Sensitization:	0.761
Carcinogencity:	0.695
Eye Corrosion:	0.045
Eye Irritation:	0.613
Respiratory Toxicity:	0.41

Download Data

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

Natural Product: NPC169941

Natural Product ID:	NPC169941
*Common Name:**	Oxyphyllenone A
IUPAC Name:	(4aR,7R,8R)-7,8-dihydroxy-4a,8-dimethyl-4,5,6,7-tetrahydro-3H-naphthalen-2-one
Synonyms:
Standard InCHIKey:	ORLGUEREMYIFNG-GRYCIOLGSA-N
Standard InCHI:	InChI=1S/C12H18O3/c1-11-5-3-8(13)7-9(11)12(2,15)10(14)4-6-11/h7,10,14-15H,3-6H2,1-2H3/t10-,11+,12-/m1/s1
SMILES:	O=C1CC[C@@]2(C(=C1)[C@@](C)(O)[C@@H](CC2)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL71537
PubChem CID:	10262534
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0001831] Carbonyl compounds [CHEMONTID:0000118] Ketones [CHEMONTID:0003487] Cyclic ketones [CHEMONTID:0004325] Cyclohexenones

*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
NPO22715	Alpinia oxyphylla	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/0031-9422(81)85171-0]
NPO24559	Cotinus coggygria	Species	Anacardiaceae	Eukaryota	Whole plant	n.a.	n.a.	PMID[11141121]
NPO22715	Alpinia oxyphylla	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11514174]
NPO22715	Alpinia oxyphylla	Species	Zingiberaceae	Eukaryota	fruit	Hainan Island, China	1998	PMID[12398545]
NPO22375	Saussurea salicifolia	Species	Asteraceae	Eukaryota	n.a.	aerial part	n.a.	PMID[18057725]
NPO24900	Vladimiria muliensis	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[18293903]
NPO24900	Vladimiria muliensis	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[19432411]
NPO22715	Alpinia oxyphylla	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22277277]
NPO25106	Arnica parryi	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23501116]
NPO22715	Alpinia oxyphylla	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23583435]
NPO27031	Methanosarcina barkeri	Species	Methanosarcinaceae	Archaea	n.a.	n.a.	n.a.	PMID[24669201]
NPO22715	Alpinia oxyphylla	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25757283]
NPO24843	Pachygone dasycarpa	Species	Menispermaceae	Eukaryota	stem bark	n.a.	n.a.	PMID[9157192]
NPO24843	Pachygone dasycarpa	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9157192]
NPO2838	Verbena officinalis	Species	Verbenaceae	Eukaryota	Flower	n.a.	n.a.	Database[FooDB]
NPO2838	Verbena officinalis	Species	Verbenaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO2838	Verbena officinalis	Species	Verbenaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO2838	Verbena officinalis	Species	Verbenaceae	Eukaryota	Root	n.a.	n.a.	Database[FooDB]
NPO2838	Verbena officinalis	Species	Verbenaceae	Eukaryota	Stem	n.a.	n.a.	Database[FooDB]
NPO2838	Verbena officinalis	Species	Verbenaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO23547	Strychnos amazonica	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24328	Gratiola officinalis	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2838	Verbena officinalis	Species	Verbenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29503	Alstonia spectabilis	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23478	Uncaria africana	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22715	Alpinia oxyphylla	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1674	Dalbergia nitidula	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24559	Cotinus coggygria	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2838	Verbena officinalis	Species	Verbenaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO22715	Alpinia oxyphylla	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2838	Verbena officinalis	Species	Verbenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23547	Strychnos amazonica	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29503	Alstonia spectabilis	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23478	Uncaria africana	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1674	Dalbergia nitidula	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24559	Cotinus coggygria	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23288	Justicia betonica	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24328	Gratiola officinalis	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2838	Verbena officinalis	Species	Verbenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO23547	Strychnos amazonica	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO24559	Cotinus coggygria	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO22715	Alpinia oxyphylla	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO2838	Verbena officinalis	Species	Verbenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO22715	Alpinia oxyphylla	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO22715	Alpinia oxyphylla	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24813	Agardhiella tenera	Species	Solieriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24688	Streptomyces ramocissimus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO24659	Eremurus chinensis	Species	Asphodelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23149	Callistemon coccineus	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13455	Hemiselmis virescens	Species	Hemiselmidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24328	Gratiola officinalis	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24874	Croton geayi	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24406	Rhizophora tagal	Species	Rhizophoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23657	Ophiocordyceps heteropoda	Species	Ophiocordycipitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2838	Verbena officinalis	Species	Verbenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1674	Dalbergia nitidula	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24900	Vladimiria muliensis	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO22375	Saussurea salicifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23837	Rubus laciniatus	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18875	Aconitum contortum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27093	Kniphofia foliosa	Species	Asphodelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21483	0nomuraea dietziae	Species	Streptosporangiaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO24969	Ageratum mexicanum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25226	Kalanchoe spathulata	Species	Crassulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24589	Grindelia discoidea	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19716	Uvaria lucida	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23288	Justicia betonica	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24268	Pteryxia terebinthina	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24118	Buxus hildebrandtii	Species	Buxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21799	Bacillus litoralis	Species	Bacillaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO24559	Cotinus coggygria	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29503	Alstonia spectabilis	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22924	Bombus terrestris	Species	Apidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25031	Petunia nyctaginiflora	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24021	Eucryphia cordifolia	Species	Cunoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27031	Methanosarcina barkeri	Species	Methanosarcinaceae	Archaea	n.a.	n.a.	n.a.	Database[UNPD]
NPO25068	Zebrina pendula	Species	Enidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17445	Streptomyces corchorusii	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO23660	Alpinia zerumbet	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23375	Hypericum reptans	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21242	Neolitsea villosa	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28259	Viguiera pinnatilobata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23478	Uncaria africana	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24493	Echinacea simulata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24191	Drypetes tessmanniana	Species	Putranjivaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18045	Holothuria atra	Species	Holothuriidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24843	Pachygone dasycarpa	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24456	Salvia lavandulifolia	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27277	Stenocarpella maydis	Species	Diaporthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24937	Callicarpa acuminata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24754	Tsitsikamma favus	Species	Latrunculiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23547	Strychnos amazonica	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25130	Hylotrupes bajulus	Species	Cerambycidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25106	Arnica parryi	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23750	Escontria chiotilla	Species	Cactaceae	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	4
Others	12

Activity Type	# Activity
Cell Line	6
Organism	5
Others	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT521	Cell Line	RBL-2H3	Rattus norvegicus	Inhibition	=	-4.7	%	PMID[451254]
NPT521	Cell Line	RBL-2H3	Rattus norvegicus	Inhibition	=	-3.3	%	PMID[451254]
NPT521	Cell Line	RBL-2H3	Rattus norvegicus	Inhibition	=	-4.5	%	PMID[451254]
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	11.99	ug.mL-1	PMID[451255]
NPT34	Cell Line	BV-2	Mus musculus	MNTD	=	100.0	uM	PMID[451256]
NPT32	Organism	Mus musculus	Mus musculus	Inhibition	=	1.6	%	PMID[451253]
NPT32	Organism	Mus musculus	Mus musculus	Inhibition	=	-2.9	%	PMID[451253]
NPT32	Organism	Mus musculus	Mus musculus	Inhibition	<	43.0	%	PMID[451253]
NPT32	Organism	Mus musculus	Mus musculus	Inhibition	<	85.7	%	PMID[451253]
NPT32	Organism	Mus musculus	Mus musculus	IC50	=	35000.0	nM	PMID[451253]
NPT2	Others	Unspecified		Inhibition	=	43.0	%	PMID[451254]
NPT2	Others	Unspecified		Inhibition	=	-2.9	%	PMID[451254]
NPT2	Others	Unspecified		Inhibition	=	85.7	%	PMID[451254]
NPT2	Others	Unspecified		Inhibition	=	1.6	%	PMID[451254]
NPT2	Others	Unspecified		IC50	=	35000.0	nM	PMID[451254]

☑ 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 NPC169941 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	173
0.1-0.2	1186
0.2-0.3	4649
0.3-0.4	9986
0.4-0.5	14509
0.5-0.6	7398
0.6-0.7	4040
0.7-0.8	709
0.8-0.85	33
0.85-0.9	10
0.9-0.95	2
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC251475
0.9136	High Similarity	NPC40687
0.8837	High Similarity	NPC116726
0.8824	High Similarity	NPC473100
0.875	High Similarity	NPC308038
0.875	High Similarity	NPC281138
0.8721	High Similarity	NPC473099
0.8701	High Similarity	NPC247586
0.869	High Similarity	NPC472974
0.8659	High Similarity	NPC93590
0.8636	High Similarity	NPC196227
0.8636	High Similarity	NPC472976
0.8636	High Similarity	NPC472977
0.8554	High Similarity	NPC66764
0.8554	High Similarity	NPC110150
0.8537	High Similarity	NPC470298
0.8523	High Similarity	NPC109305
0.8471	Intermediate Similarity	NPC179591
0.8471	Intermediate Similarity	NPC472985
0.8471	Intermediate Similarity	NPC472986
0.8415	Intermediate Similarity	NPC104120
0.8415	Intermediate Similarity	NPC157895
0.8415	Intermediate Similarity	NPC148685
0.8415	Intermediate Similarity	NPC172013
0.8391	Intermediate Similarity	NPC472973
0.8375	Intermediate Similarity	NPC263582
0.8333	Intermediate Similarity	NPC64600
0.8295	Intermediate Similarity	NPC134321
0.8276	Intermediate Similarity	NPC158778
0.8272	Intermediate Similarity	NPC266193
0.8272	Intermediate Similarity	NPC197659
0.8272	Intermediate Similarity	NPC257666
0.8272	Intermediate Similarity	NPC74995
0.825	Intermediate Similarity	NPC114236
0.8242	Intermediate Similarity	NPC117133
0.8202	Intermediate Similarity	NPC472978
0.8182	Intermediate Similarity	NPC472983
0.8171	Intermediate Similarity	NPC475994
0.8171	Intermediate Similarity	NPC178852
0.8171	Intermediate Similarity	NPC62336
0.8161	Intermediate Similarity	NPC472324
0.8152	Intermediate Similarity	NPC474785
0.8152	Intermediate Similarity	NPC474938
0.8148	Intermediate Similarity	NPC472305
0.814	Intermediate Similarity	NPC79573
0.8132	Intermediate Similarity	NPC53565
0.8125	Intermediate Similarity	NPC470299
0.8118	Intermediate Similarity	NPC105173
0.8101	Intermediate Similarity	NPC84790
0.809	Intermediate Similarity	NPC48010
0.809	Intermediate Similarity	NPC230332
0.809	Intermediate Similarity	NPC128672
0.8072	Intermediate Similarity	NPC152061
0.8049	Intermediate Similarity	NPC203403
0.8049	Intermediate Similarity	NPC34110
0.8046	Intermediate Similarity	NPC473226
0.8043	Intermediate Similarity	NPC471463
0.8023	Intermediate Similarity	NPC476412
0.8	Intermediate Similarity	NPC473424
0.8	Intermediate Similarity	NPC73457
0.8	Intermediate Similarity	NPC475441
0.8	Intermediate Similarity	NPC155304
0.8	Intermediate Similarity	NPC472975
0.8	Intermediate Similarity	NPC477915
0.8	Intermediate Similarity	NPC475806
0.7978	Intermediate Similarity	NPC77263
0.7978	Intermediate Similarity	NPC309603
0.7978	Intermediate Similarity	NPC473999
0.7978	Intermediate Similarity	NPC250592
0.7976	Intermediate Similarity	NPC472301
0.7976	Intermediate Similarity	NPC471514
0.7975	Intermediate Similarity	NPC173321
0.7957	Intermediate Similarity	NPC161147
0.7938	Intermediate Similarity	NPC149047
0.7935	Intermediate Similarity	NPC259286
0.7935	Intermediate Similarity	NPC271195
0.7935	Intermediate Similarity	NPC473170
0.7935	Intermediate Similarity	NPC476245
0.7931	Intermediate Similarity	NPC15807
0.7931	Intermediate Similarity	NPC470574
0.7927	Intermediate Similarity	NPC7629
0.7927	Intermediate Similarity	NPC470525
0.7927	Intermediate Similarity	NPC151622
0.7912	Intermediate Similarity	NPC69454
0.7912	Intermediate Similarity	NPC474736
0.7889	Intermediate Similarity	NPC472325
0.7882	Intermediate Similarity	NPC226068
0.7882	Intermediate Similarity	NPC473420
0.7865	Intermediate Similarity	NPC104560
0.7865	Intermediate Similarity	NPC471722
0.7865	Intermediate Similarity	NPC471791
0.7865	Intermediate Similarity	NPC471793
0.7857	Intermediate Similarity	NPC220229
0.7857	Intermediate Similarity	NPC475060
0.7857	Intermediate Similarity	NPC19900
0.7849	Intermediate Similarity	NPC249954
0.7841	Intermediate Similarity	NPC198761
0.7841	Intermediate Similarity	NPC194417
0.7841	Intermediate Similarity	NPC475069
0.7841	Intermediate Similarity	NPC470955
0.7841	Intermediate Similarity	NPC82979
0.7841	Intermediate Similarity	NPC175145
0.7835	Intermediate Similarity	NPC209502
0.7835	Intermediate Similarity	NPC204833
0.7831	Intermediate Similarity	NPC325946
0.7831	Intermediate Similarity	NPC85105
0.7831	Intermediate Similarity	NPC149550
0.7826	Intermediate Similarity	NPC8993
0.7826	Intermediate Similarity	NPC470957
0.7826	Intermediate Similarity	NPC470958
0.7826	Intermediate Similarity	NPC299100
0.7826	Intermediate Similarity	NPC474690
0.7816	Intermediate Similarity	NPC130966
0.7802	Intermediate Similarity	NPC473998
0.7802	Intermediate Similarity	NPC233116
0.7802	Intermediate Similarity	NPC63748
0.7792	Intermediate Similarity	NPC287339
0.7791	Intermediate Similarity	NPC38796
0.7791	Intermediate Similarity	NPC48362
0.7791	Intermediate Similarity	NPC158411
0.7791	Intermediate Similarity	NPC212083
0.7789	Intermediate Similarity	NPC198880
0.7778	Intermediate Similarity	NPC29542
0.7778	Intermediate Similarity	NPC186042
0.7778	Intermediate Similarity	NPC323437
0.7778	Intermediate Similarity	NPC118011
0.7778	Intermediate Similarity	NPC32830
0.7778	Intermediate Similarity	NPC201562
0.7778	Intermediate Similarity	NPC469319
0.7778	Intermediate Similarity	NPC217201
0.7778	Intermediate Similarity	NPC472971
0.7778	Intermediate Similarity	NPC36668
0.7778	Intermediate Similarity	NPC229871
0.7778	Intermediate Similarity	NPC119416
0.7778	Intermediate Similarity	NPC472970
0.7765	Intermediate Similarity	NPC2482
0.7755	Intermediate Similarity	NPC48733
0.7755	Intermediate Similarity	NPC202167
0.7755	Intermediate Similarity	NPC49958
0.7755	Intermediate Similarity	NPC476027
0.7755	Intermediate Similarity	NPC85829
0.7755	Intermediate Similarity	NPC302607
0.7755	Intermediate Similarity	NPC50692
0.7755	Intermediate Similarity	NPC150531
0.7755	Intermediate Similarity	NPC260268
0.7755	Intermediate Similarity	NPC319077
0.7755	Intermediate Similarity	NPC171137
0.7755	Intermediate Similarity	NPC152695
0.7755	Intermediate Similarity	NPC214264
0.7755	Intermediate Similarity	NPC296945
0.7755	Intermediate Similarity	NPC97202
0.7755	Intermediate Similarity	NPC323834
0.7753	Intermediate Similarity	NPC272039
0.7753	Intermediate Similarity	NPC138756
0.7753	Intermediate Similarity	NPC475740
0.7753	Intermediate Similarity	NPC220930
0.7753	Intermediate Similarity	NPC471792
0.7742	Intermediate Similarity	NPC316215
0.7742	Intermediate Similarity	NPC180950
0.7742	Intermediate Similarity	NPC134067
0.7742	Intermediate Similarity	NPC200702
0.7738	Intermediate Similarity	NPC80088
0.7738	Intermediate Similarity	NPC253561
0.7738	Intermediate Similarity	NPC275494
0.7738	Intermediate Similarity	NPC471409
0.7738	Intermediate Similarity	NPC207772
0.7732	Intermediate Similarity	NPC475050
0.7727	Intermediate Similarity	NPC52628
0.7727	Intermediate Similarity	NPC476426
0.7727	Intermediate Similarity	NPC476678
0.7727	Intermediate Similarity	NPC474853
0.7727	Intermediate Similarity	NPC471267
0.7727	Intermediate Similarity	NPC197823
0.7727	Intermediate Similarity	NPC179006
0.7711	Intermediate Similarity	NPC186554
0.7711	Intermediate Similarity	NPC250621
0.7711	Intermediate Similarity	NPC76966
0.7708	Intermediate Similarity	NPC115862
0.7708	Intermediate Similarity	NPC470184
0.7701	Intermediate Similarity	NPC297398
0.7701	Intermediate Similarity	NPC471987
0.77	Intermediate Similarity	NPC11710
0.77	Intermediate Similarity	NPC214644
0.7684	Intermediate Similarity	NPC478056
0.7683	Intermediate Similarity	NPC215050
0.7677	Intermediate Similarity	NPC83744
0.7677	Intermediate Similarity	NPC477916
0.7674	Intermediate Similarity	NPC159148
0.7674	Intermediate Similarity	NPC121984
0.7674	Intermediate Similarity	NPC136150
0.7674	Intermediate Similarity	NPC14151
0.7674	Intermediate Similarity	NPC119229
0.7667	Intermediate Similarity	NPC58271
0.7667	Intermediate Similarity	NPC206060
0.7667	Intermediate Similarity	NPC53454
0.7667	Intermediate Similarity	NPC472802
0.7667	Intermediate Similarity	NPC48107
0.7667	Intermediate Similarity	NPC328539
0.7667	Intermediate Similarity	NPC474677
0.7667	Intermediate Similarity	NPC473229

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 NPC169941 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	165
0.1-0.2	1652
0.2-0.3	3829
0.3-0.4	2395
0.4-0.5	699
0.5-0.6	252
0.6-0.7	152
0.7-0.8	6
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7841	Intermediate Similarity	NPD3618	Phase 1
0.7586	Intermediate Similarity	NPD3667	Approved
0.7582	Intermediate Similarity	NPD5328	Approved
0.7528	Intermediate Similarity	NPD1696	Phase 3
0.7527	Intermediate Similarity	NPD4202	Approved
0.7419	Intermediate Similarity	NPD7515	Phase 2
0.7419	Intermediate Similarity	NPD6079	Approved
0.7416	Intermediate Similarity	NPD3133	Approved
0.7416	Intermediate Similarity	NPD4786	Approved
0.7416	Intermediate Similarity	NPD3666	Approved
0.7416	Intermediate Similarity	NPD3665	Phase 1
0.7273	Intermediate Similarity	NPD5211	Phase 2
0.7253	Intermediate Similarity	NPD4623	Approved
0.7253	Intermediate Similarity	NPD5279	Phase 3
0.7253	Intermediate Similarity	NPD4519	Discontinued
0.7216	Intermediate Similarity	NPD4755	Approved
0.7159	Intermediate Similarity	NPD4695	Discontinued
0.7159	Intermediate Similarity	NPD8259	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD4225	Approved
0.7129	Intermediate Similarity	NPD5141	Approved
0.7113	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7113	Intermediate Similarity	NPD5221	Approved
0.7113	Intermediate Similarity	NPD5222	Approved
0.7113	Intermediate Similarity	NPD4697	Phase 3
0.7083	Intermediate Similarity	NPD7748	Approved
0.7071	Intermediate Similarity	NPD5286	Approved
0.7071	Intermediate Similarity	NPD4700	Approved
0.7071	Intermediate Similarity	NPD4696	Approved
0.7071	Intermediate Similarity	NPD5285	Approved
0.7065	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD5173	Approved
0.7037	Intermediate Similarity	NPD7115	Discovery
0.7021	Intermediate Similarity	NPD4753	Phase 2
0.7	Intermediate Similarity	NPD4223	Phase 3
0.7	Intermediate Similarity	NPD5223	Approved
0.7	Intermediate Similarity	NPD4221	Approved
0.6957	Remote Similarity	NPD1694	Approved
0.6931	Remote Similarity	NPD5226	Approved
0.6931	Remote Similarity	NPD5224	Approved
0.6931	Remote Similarity	NPD5225	Approved
0.6931	Remote Similarity	NPD4633	Approved
0.6869	Remote Similarity	NPD7902	Approved
0.6863	Remote Similarity	NPD5174	Approved
0.6863	Remote Similarity	NPD5175	Approved
0.6863	Remote Similarity	NPD4754	Approved
0.6857	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD3668	Phase 3
0.6848	Remote Similarity	NPD4197	Approved
0.6829	Remote Similarity	NPD7331	Phase 2
0.6792	Remote Similarity	NPD4634	Approved
0.6782	Remote Similarity	NPD8264	Approved
0.6774	Remote Similarity	NPD5329	Approved
0.6742	Remote Similarity	NPD3617	Approved
0.6733	Remote Similarity	NPD7639	Approved
0.6733	Remote Similarity	NPD7640	Approved
0.6731	Remote Similarity	NPD4768	Approved
0.6731	Remote Similarity	NPD6402	Approved
0.6731	Remote Similarity	NPD7128	Approved
0.6731	Remote Similarity	NPD5739	Approved
0.6731	Remote Similarity	NPD4767	Approved
0.6731	Remote Similarity	NPD6675	Approved
0.6707	Remote Similarity	NPD7341	Phase 2
0.6702	Remote Similarity	NPD4693	Phase 3
0.6702	Remote Similarity	NPD4138	Approved
0.6702	Remote Similarity	NPD5280	Approved
0.6702	Remote Similarity	NPD5690	Phase 2
0.6702	Remote Similarity	NPD4688	Approved
0.6702	Remote Similarity	NPD4689	Approved
0.6702	Remote Similarity	NPD5205	Approved
0.6702	Remote Similarity	NPD4690	Approved
0.6702	Remote Similarity	NPD4694	Approved
0.6667	Remote Similarity	NPD5697	Approved
0.6667	Remote Similarity	NPD5210	Approved
0.6667	Remote Similarity	NPD4629	Approved
0.6667	Remote Similarity	NPD5701	Approved
0.6634	Remote Similarity	NPD7638	Approved
0.6633	Remote Similarity	NPD6399	Phase 3
0.6632	Remote Similarity	NPD3573	Approved
0.6606	Remote Similarity	NPD4632	Approved
0.6604	Remote Similarity	NPD6899	Approved
0.6604	Remote Similarity	NPD6011	Approved
0.6604	Remote Similarity	NPD7320	Approved
0.6604	Remote Similarity	NPD6881	Approved
0.6604	Remote Similarity	NPD4730	Approved
0.6604	Remote Similarity	NPD4729	Approved
0.6604	Remote Similarity	NPD5128	Approved
0.6566	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6566	Remote Similarity	NPD7900	Approved
0.6542	Remote Similarity	NPD6012	Approved
0.6542	Remote Similarity	NPD6373	Approved
0.6542	Remote Similarity	NPD6013	Approved
0.6542	Remote Similarity	NPD6372	Approved
0.6542	Remote Similarity	NPD6014	Approved
0.6535	Remote Similarity	NPD6083	Phase 2
0.6535	Remote Similarity	NPD6084	Phase 2
0.6526	Remote Similarity	NPD7521	Approved
0.6526	Remote Similarity	NPD5330	Approved
0.6526	Remote Similarity	NPD7146	Approved
0.6526	Remote Similarity	NPD7334	Approved
0.6526	Remote Similarity	NPD6684	Approved
0.6526	Remote Similarity	NPD6409	Approved
0.6517	Remote Similarity	NPD6933	Approved
0.6517	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6514	Remote Similarity	NPD8297	Approved
0.65	Remote Similarity	NPD5695	Phase 3
0.6495	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6484	Remote Similarity	NPD7645	Phase 2
0.6481	Remote Similarity	NPD5169	Approved
0.6481	Remote Similarity	NPD6883	Approved
0.6481	Remote Similarity	NPD5250	Approved
0.6481	Remote Similarity	NPD7102	Approved
0.6481	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6481	Remote Similarity	NPD5135	Approved
0.6481	Remote Similarity	NPD5248	Approved
0.6481	Remote Similarity	NPD5249	Phase 3
0.6481	Remote Similarity	NPD7290	Approved
0.6481	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6481	Remote Similarity	NPD5247	Approved
0.6481	Remote Similarity	NPD5251	Approved
0.6465	Remote Similarity	NPD5779	Approved
0.6465	Remote Similarity	NPD5778	Approved
0.6458	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6449	Remote Similarity	NPD5168	Approved
0.6429	Remote Similarity	NPD4096	Approved
0.6422	Remote Similarity	NPD5127	Approved
0.6422	Remote Similarity	NPD6650	Approved
0.6422	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6422	Remote Similarity	NPD8130	Phase 1
0.6422	Remote Similarity	NPD5217	Approved
0.6422	Remote Similarity	NPD6649	Approved
0.6422	Remote Similarity	NPD6869	Approved
0.6422	Remote Similarity	NPD5216	Approved
0.6422	Remote Similarity	NPD6617	Approved
0.6422	Remote Similarity	NPD6847	Approved
0.6422	Remote Similarity	NPD5215	Approved
0.6421	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6413	Remote Similarity	NPD7525	Registered
0.6404	Remote Similarity	NPD6942	Approved
0.6404	Remote Similarity	NPD7339	Approved
0.6392	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6392	Remote Similarity	NPD6903	Approved
0.6392	Remote Similarity	NPD4518	Approved
0.6383	Remote Similarity	NPD4788	Approved
0.6374	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD6411	Approved
0.6364	Remote Similarity	NPD5284	Approved
0.6364	Remote Similarity	NPD5281	Approved
0.6364	Remote Similarity	NPD6882	Approved
0.6355	Remote Similarity	NPD6412	Phase 2
0.6346	Remote Similarity	NPD5344	Discontinued
0.6344	Remote Similarity	NPD4692	Approved
0.6344	Remote Similarity	NPD4139	Approved
0.6341	Remote Similarity	NPD368	Approved
0.6311	Remote Similarity	NPD5696	Approved
0.6304	Remote Similarity	NPD4195	Approved
0.63	Remote Similarity	NPD5133	Approved
0.6296	Remote Similarity	NPD6686	Approved
0.6292	Remote Similarity	NPD6924	Approved
0.6292	Remote Similarity	NPD6926	Approved
0.6289	Remote Similarity	NPD7524	Approved
0.6286	Remote Similarity	NPD7632	Discontinued
0.6283	Remote Similarity	NPD6009	Approved
0.6265	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.6263	Remote Similarity	NPD46	Approved
0.6263	Remote Similarity	NPD5785	Approved
0.6263	Remote Similarity	NPD6698	Approved
0.6262	Remote Similarity	NPD6008	Approved
0.6261	Remote Similarity	NPD6319	Approved
0.625	Remote Similarity	NPD5167	Approved
0.625	Remote Similarity	NPD5363	Approved
0.6239	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6237	Remote Similarity	NPD6931	Approved
0.6237	Remote Similarity	NPD4748	Discontinued
0.6237	Remote Similarity	NPD6930	Phase 2
0.6235	Remote Similarity	NPD3704	Approved
0.6224	Remote Similarity	NPD5737	Approved
0.6224	Remote Similarity	NPD6672	Approved
0.6211	Remote Similarity	NPD6110	Phase 1
0.6207	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6207	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6207	Remote Similarity	NPD4137	Phase 3
0.6204	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6196	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6195	Remote Similarity	NPD6274	Approved
0.6176	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6162	Remote Similarity	NPD6101	Approved
0.6162	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD5290	Discontinued
0.6147	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6146	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.614	Remote Similarity	NPD6317	Approved
0.6136	Remote Similarity	NPD4747	Approved
0.6136	Remote Similarity	NPD4691	Approved
0.6129	Remote Similarity	NPD6929	Approved
0.6121	Remote Similarity	NPD6054	Approved
0.6121	Remote Similarity	NPD6059	Approved
0.6105	Remote Similarity	NPD4269	Approved
0.6105	Remote Similarity	NPD4270	Approved
0.6087	Remote Similarity	NPD6313	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