NPASS Compound

Structure

CID243272 OpenBabel06191716042D 22 22 0 0 0 0 0 0 0 0999 V2000 -8.6603 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6603 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 3 1 0 0 0 0 2 22 1 0 0 0 0 3 4 1 0 0 0 0 4 5 1 0 0 0 0 5 6 1 0 0 0 0 6 7 1 0 0 0 0 7 8 1 0 0 0 0 8 9 1 0 0 0 0 9 10 1 0 0 0 0 10 11 1 0 0 0 0 11 12 1 0 0 0 0 12 14 1 0 0 0 0 13 15 1 0 0 0 0 13 16 2 0 0 0 0 14 17 2 0 0 0 0 14 18 1 0 0 0 0 15 17 1 0 0 0 0 15 19 2 0 0 0 0 16 18 1 0 0 0 0 16 22 1 0 0 0 0 17 20 1 0 0 0 0 18 21 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	308.2
Volume:	335.943
LogP:	5.252
LogD:	3.702
LogS:	-4.1
# Rotatable Bonds:	10
TPSA:	69.92
# H-Bond Aceptor:	4
# H-Bond Donor:	3
# Rings:	1
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.254
Synthetic Accessibility Score:	2.552
Fsp3:	0.556
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	2
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.78
MDCK Permeability:	2.27777363761561e-05
Pgp-inhibitor:	0.005
Pgp-substrate:	0.005
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.969
30% Bioavailability (F30%):	0.964

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.042
Plasma Protein Binding (PPB):	98.97312927246094%
Volume Distribution (VD):	4.908
Pgp-substrate:	1.7782589197158813%

ADMET: Metabolism

CYP1A2-inhibitor:	0.874
CYP1A2-substrate:	0.712
CYP2C19-inhibitor:	0.616
CYP2C19-substrate:	0.161
CYP2C9-inhibitor:	0.518
CYP2C9-substrate:	0.921
CYP2D6-inhibitor:	0.757
CYP2D6-substrate:	0.801
CYP3A4-inhibitor:	0.207
CYP3A4-substrate:	0.063

ADMET: Excretion

Clearance (CL):	9.858
Half-life (T1/2):	0.78

ADMET: Toxicity

hERG Blockers:	0.019
Human Hepatotoxicity (H-HT):	0.006
Drug-inuced Liver Injury (DILI):	0.011
AMES Toxicity:	0.145
Rat Oral Acute Toxicity:	0.097
Maximum Recommended Daily Dose:	0.033
Skin Sensitization:	0.968
Carcinogencity:	0.155
Eye Corrosion:	0.111
Eye Irritation:	0.932
Respiratory Toxicity:	0.434

Download Data

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

Natural Product: NPC243272

Natural Product ID:	NPC243272
*Common Name:**	5-O-Methylembelin
IUPAC Name:	2-hydroxy-5-methoxy-3-undecylcyclohexa-2,5-diene-1,4-dione
Synonyms:	5-O-Methylembelin
Standard InCHIKey:	KHBJLRRAMCJZLZ-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C18H28O4/c1-3-4-5-6-7-8-9-10-11-12-14-17(20)15(19)13-16(22-2)18(14)21/h13,20H,3-12H2,1-2H3
SMILES:	CCCCCCCCCCCC1=C(C(=O)C=C(C1=O)OC)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL471270
PubChem CID:	171489
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:0002495] Quinones [CHEMONTID:0002384] Benzoquinones [CHEMONTID:0002494] P-benzoquinones

*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
NPO17145	Aegiceras corniculatum	Species	Primulaceae	Eukaryota	n.a.	twig	n.a.	DOI[10.1021/np50063a031]
NPO17145	Aegiceras corniculatum	Species	Primulaceae	Eukaryota	n.a.	stem	n.a.	DOI[10.1021/np50063a031]
NPO20142	Embelia schimperi	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11054840]
NPO31207	Oxalis erythrorhiza	Species	Oxalidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12963150]
NPO17145	Aegiceras corniculatum	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15165134]
NPO26772	Lysimachia punctata	Species	Primulaceae	Eukaryota	n.a.	root	n.a.	PMID[15890461]
NPO17145	Aegiceras corniculatum	Species	Primulaceae	Eukaryota	n.a.	stem	n.a.	PMID[16254827]
NPO17145	Aegiceras corniculatum	Species	Primulaceae	Eukaryota	n.a.	twig	n.a.	PMID[16254827]
NPO15741	Embelia ribes	Species	Primulaceae	Eukaryota	n.a.	leaf	n.a.	PMID[17124632]
NPO15741	Embelia ribes	Species	Primulaceae	Eukaryota	n.a.	fruit	n.a.	PMID[17124632]
NPO15741	Embelia ribes	Species	Primulaceae	Eukaryota	roots	n.a.	n.a.	PMID[17125236]
NPO15741	Embelia ribes	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17125236]
NPO15388	Eucalyptus globulus	Species	Myrtaceae	Eukaryota	n.a.	fruit	n.a.	PMID[18020353]
NPO17145	Aegiceras corniculatum	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22316191]
NPO15388	Eucalyptus globulus	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22934600]
NPO15388	Eucalyptus globulus	Species	Myrtaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[23678820]
NPO17145	Aegiceras corniculatum	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[2778454]
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]
NPO15388	Eucalyptus globulus	Species	Myrtaceae	Eukaryota	Fruits	n.a.	n.a.	PMID[30543429]
NPO15388	Eucalyptus globulus	Species	Myrtaceae	Eukaryota	Fruits	n.a.	n.a.	PMID[30848923]
NPO15388	Eucalyptus globulus	Species	Myrtaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[8864235]
NPO23736	Myrsine africana	Species	Primulaceae	Eukaryota	n.a.	fruit	n.a.	Database[Article]
NPO15741	Embelia ribes	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15388	Eucalyptus globulus	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23736	Myrsine africana	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17145	Aegiceras corniculatum	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO20142	Embelia schimperi	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23736	Myrsine africana	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17145	Aegiceras corniculatum	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15388	Eucalyptus globulus	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15741	Embelia ribes	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15388	Eucalyptus globulus	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO23736	Myrsine africana	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15388	Eucalyptus globulus	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26772	Lysimachia punctata	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20142	Embelia schimperi	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17145	Aegiceras corniculatum	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15741	Embelia ribes	Species	Primulaceae	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	9
MIC	2
Others	3

Activity Type	# Activity
Cell Line	4
Individual Protein	6
Organism	3
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT116	Cell Line	HL-60	Homo sapiens	IC50	=	3.0	ug.mL-1	PMID[459736]
NPT181	Cell Line	Bel-7402	Homo sapiens	IC50	=	3.6	ug.mL-1	PMID[459736]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	9.0	ug.mL-1	PMID[459736]
NPT466	Cell Line	U-937	Homo sapiens	IC50	=	1.5	ug.mL-1	PMID[459736]
NPT570	Individual Protein	Arachidonate 5-lipoxygenase	Homo sapiens	IC50	=	680.0	nM	PMID[459740]
NPT570	Individual Protein	Arachidonate 5-lipoxygenase	Homo sapiens	IC50	=	3800.0	nM	PMID[459740]
NPT570	Individual Protein	Arachidonate 5-lipoxygenase	Homo sapiens	IC50	=	1300.0	nM	PMID[459740]
NPT1119	Individual Protein	Arachidonate 12-lipoxygenase	Homo sapiens	Activity	=	138.4	%	PMID[459740]
NPT3167	Individual Protein	Macrophage-expressed gene 1 protein	Homo sapiens	IC50	=	9100.0	nM	PMID[459740]
NPT2527	Organism	Pythium ultimum	Pythium ultimum	IZ	=	8.0	mm	PMID[459737]
NPT88	Organism	Mycobacterium tuberculosis	Mycobacterium tuberculosis	MIC	=	32.9	ug.mL-1	PMID[459738]
NPT790	Organism	Mycobacterium tuberculosis H37Rv	Mycobacterium tuberculosis H37Rv	MIC	=	15.0	ug.mL-1	PMID[459738]
NPT2	Others	Unspecified		IC50	=	90190.0	nM	PMID[459739]
NPT792	Individual Protein	Arachidonate 15-lipoxygenase	Homo sapiens	Activity	=	131.2	%	PMID[459740]

☑ 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 NPC243272 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	155
0.1-0.2	1741
0.2-0.3	8741
0.3-0.4	18309
0.4-0.5	8738
0.5-0.6	4145
0.6-0.7	776
0.7-0.8	60
0.8-0.85	7
0.85-0.9	4
0.9-0.95	13
0.95-1	8

Similarity Score	Similarity Level	Natural Product ID
0.9841	High Similarity	NPC146376
0.9841	High Similarity	NPC263382
0.9841	High Similarity	NPC125578
0.9688	High Similarity	NPC262673
0.9688	High Similarity	NPC94488
0.9538	High Similarity	NPC291062
0.9538	High Similarity	NPC94743
0.9355	High Similarity	NPC143168
0.9355	High Similarity	NPC53109
0.9206	High Similarity	NPC474400
0.9206	High Similarity	NPC7029
0.9206	High Similarity	NPC34622
0.9118	High Similarity	NPC264178
0.9077	High Similarity	NPC474619
0.9062	High Similarity	NPC98897
0.9048	High Similarity	NPC151728
0.9048	High Similarity	NPC57463
0.9048	High Similarity	NPC477830
0.8939	High Similarity	NPC134385
0.8923	High Similarity	NPC16119
0.871	High Similarity	NPC320421
0.8571	High Similarity	NPC473494
0.8472	Intermediate Similarity	NPC473536
0.8125	Intermediate Similarity	NPC139056
0.7971	Intermediate Similarity	NPC251429
0.791	Intermediate Similarity	NPC477707
0.7848	Intermediate Similarity	NPC132228
0.7848	Intermediate Similarity	NPC8518
0.7848	Intermediate Similarity	NPC263997
0.7848	Intermediate Similarity	NPC241512
0.7848	Intermediate Similarity	NPC6185
0.7838	Intermediate Similarity	NPC477708
0.7808	Intermediate Similarity	NPC147438
0.7778	Intermediate Similarity	NPC317796
0.7742	Intermediate Similarity	NPC137396
0.7692	Intermediate Similarity	NPC224103
0.7692	Intermediate Similarity	NPC200831
0.7692	Intermediate Similarity	NPC299369
0.7619	Intermediate Similarity	NPC474805
0.76	Intermediate Similarity	NPC26504
0.75	Intermediate Similarity	NPC283087
0.7424	Intermediate Similarity	NPC192843
0.7407	Intermediate Similarity	NPC474680
0.7381	Intermediate Similarity	NPC475823
0.7381	Intermediate Similarity	NPC474209
0.7349	Intermediate Similarity	NPC53454
0.7342	Intermediate Similarity	NPC474085
0.7342	Intermediate Similarity	NPC55869
0.7342	Intermediate Similarity	NPC99308
0.7317	Intermediate Similarity	NPC472009
0.7317	Intermediate Similarity	NPC203795
0.7308	Intermediate Similarity	NPC475681
0.7302	Intermediate Similarity	NPC22329
0.7297	Intermediate Similarity	NPC474539
0.726	Intermediate Similarity	NPC469914
0.725	Intermediate Similarity	NPC103486
0.725	Intermediate Similarity	NPC47450
0.7246	Intermediate Similarity	NPC40082
0.7237	Intermediate Similarity	NPC175079
0.7229	Intermediate Similarity	NPC472007
0.7222	Intermediate Similarity	NPC473213
0.7222	Intermediate Similarity	NPC298249
0.7215	Intermediate Similarity	NPC108955
0.7206	Intermediate Similarity	NPC274927
0.7206	Intermediate Similarity	NPC106851
0.7195	Intermediate Similarity	NPC77971
0.7195	Intermediate Similarity	NPC470177
0.7195	Intermediate Similarity	NPC90287
0.7195	Intermediate Similarity	NPC32037
0.7179	Intermediate Similarity	NPC231739
0.7164	Intermediate Similarity	NPC281230
0.7162	Intermediate Similarity	NPC477455
0.7162	Intermediate Similarity	NPC173321
0.716	Intermediate Similarity	NPC105803
0.7143	Intermediate Similarity	NPC472008
0.7143	Intermediate Similarity	NPC110725
0.7143	Intermediate Similarity	NPC220191
0.7123	Intermediate Similarity	NPC477452
0.7101	Intermediate Similarity	NPC174447
0.7101	Intermediate Similarity	NPC251042
0.7101	Intermediate Similarity	NPC122521
0.7101	Intermediate Similarity	NPC235242
0.7051	Intermediate Similarity	NPC471061
0.7027	Intermediate Similarity	NPC474060
0.7	Intermediate Similarity	NPC254449
0.7	Intermediate Similarity	NPC115752
0.7	Intermediate Similarity	NPC138056
0.7	Intermediate Similarity	NPC15130
0.7	Intermediate Similarity	NPC473212
0.6988	Remote Similarity	NPC133652
0.6977	Remote Similarity	NPC471399
0.6962	Remote Similarity	NPC23778
0.6962	Remote Similarity	NPC478122
0.6962	Remote Similarity	NPC475994
0.6962	Remote Similarity	NPC30321
0.6951	Remote Similarity	NPC477784
0.6951	Remote Similarity	NPC477785
0.6951	Remote Similarity	NPC477786
0.6944	Remote Similarity	NPC61473
0.6923	Remote Similarity	NPC470525
0.6923	Remote Similarity	NPC92080
0.6914	Remote Similarity	NPC275766
0.6914	Remote Similarity	NPC225515
0.6901	Remote Similarity	NPC473211
0.6901	Remote Similarity	NPC473210
0.6897	Remote Similarity	NPC146852
0.6875	Remote Similarity	NPC27817
0.6857	Remote Similarity	NPC229252
0.6857	Remote Similarity	NPC143857
0.6854	Remote Similarity	NPC279313
0.6849	Remote Similarity	NPC197089
0.6849	Remote Similarity	NPC137163
0.6835	Remote Similarity	NPC211279
0.6818	Remote Similarity	NPC61275
0.68	Remote Similarity	NPC143396
0.68	Remote Similarity	NPC10758
0.68	Remote Similarity	NPC250928
0.679	Remote Similarity	NPC162741
0.679	Remote Similarity	NPC91332
0.6782	Remote Similarity	NPC223093
0.6782	Remote Similarity	NPC166554
0.6782	Remote Similarity	NPC265856
0.6769	Remote Similarity	NPC477458
0.6765	Remote Similarity	NPC477201
0.6761	Remote Similarity	NPC201939
0.675	Remote Similarity	NPC74410
0.675	Remote Similarity	NPC189485
0.6747	Remote Similarity	NPC8091
0.6744	Remote Similarity	NPC475001
0.6744	Remote Similarity	NPC185059
0.6716	Remote Similarity	NPC129710
0.6712	Remote Similarity	NPC474304
0.6712	Remote Similarity	NPC296436
0.6712	Remote Similarity	NPC176215
0.6712	Remote Similarity	NPC474329
0.6711	Remote Similarity	NPC318766
0.6709	Remote Similarity	NPC180886
0.6709	Remote Similarity	NPC1254
0.6707	Remote Similarity	NPC116797
0.6707	Remote Similarity	NPC474353
0.6707	Remote Similarity	NPC286229
0.6706	Remote Similarity	NPC261721
0.6705	Remote Similarity	NPC174167
0.6705	Remote Similarity	NPC470036
0.6705	Remote Similarity	NPC26865
0.6705	Remote Similarity	NPC193396
0.6705	Remote Similarity	NPC45579
0.6705	Remote Similarity	NPC32944
0.6703	Remote Similarity	NPC20066
0.6667	Remote Similarity	NPC192329
0.6667	Remote Similarity	NPC268185
0.6667	Remote Similarity	NPC142159
0.6667	Remote Similarity	NPC469809
0.6667	Remote Similarity	NPC476614
0.6667	Remote Similarity	NPC160540
0.6667	Remote Similarity	NPC471740
0.6667	Remote Similarity	NPC91408
0.6667	Remote Similarity	NPC469884
0.6667	Remote Similarity	NPC474251
0.6667	Remote Similarity	NPC95364
0.6667	Remote Similarity	NPC280833
0.6667	Remote Similarity	NPC122244
0.6667	Remote Similarity	NPC134593
0.6667	Remote Similarity	NPC474321
0.6667	Remote Similarity	NPC227396
0.663	Remote Similarity	NPC300584
0.6629	Remote Similarity	NPC263780
0.6628	Remote Similarity	NPC471738
0.6625	Remote Similarity	NPC316324
0.6623	Remote Similarity	NPC144627
0.6623	Remote Similarity	NPC84790
0.6622	Remote Similarity	NPC83965
0.662	Remote Similarity	NPC243532
0.6613	Remote Similarity	NPC106547
0.6591	Remote Similarity	NPC469464
0.6588	Remote Similarity	NPC307112
0.6588	Remote Similarity	NPC307126
0.6588	Remote Similarity	NPC79573
0.6588	Remote Similarity	NPC255174
0.6588	Remote Similarity	NPC68303
0.6588	Remote Similarity	NPC187529
0.6585	Remote Similarity	NPC2482
0.6585	Remote Similarity	NPC74086
0.6585	Remote Similarity	NPC304795
0.6582	Remote Similarity	NPC114236
0.6582	Remote Similarity	NPC474885
0.6579	Remote Similarity	NPC67608
0.6575	Remote Similarity	NPC150162
0.6575	Remote Similarity	NPC328089
0.6575	Remote Similarity	NPC68343
0.6571	Remote Similarity	NPC34416
0.6567	Remote Similarity	NPC36061
0.6567	Remote Similarity	NPC294548
0.6567	Remote Similarity	NPC1813
0.6567	Remote Similarity	NPC168521
0.6567	Remote Similarity	NPC139029
0.6556	Remote Similarity	NPC23170
0.6552	Remote Similarity	NPC26078
0.6552	Remote Similarity	NPC307298
0.6552	Remote Similarity	NPC58271

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 NPC243272 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	139
0.1-0.2	2525
0.2-0.3	4170
0.3-0.4	1735
0.4-0.5	364
0.5-0.6	193
0.6-0.7	18
0.7-0.8	2
0.8-0.85	0
0.85-0.9	1
0.9-0.95	3
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9355	High Similarity	NPD2664	Clinical (unspecified phase)
0.9219	High Similarity	NPD3704	Approved
0.8923	High Similarity	NPD6108	Clinical (unspecified phase)
0.8732	High Similarity	NPD4756	Discovery
0.7692	Intermediate Similarity	NPD8779	Phase 3
0.7436	Intermediate Similarity	NPD4695	Discontinued
0.7324	Intermediate Similarity	NPD7331	Phase 2
0.6944	Remote Similarity	NPD7341	Phase 2
0.6866	Remote Similarity	NPD4627	Clinical (unspecified phase)
0.6585	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6575	Remote Similarity	NPD3197	Phase 1
0.6567	Remote Similarity	NPD3172	Approved
0.6556	Remote Similarity	NPD5282	Discontinued
0.6548	Remote Similarity	NPD6110	Phase 1
0.6543	Remote Similarity	NPD3617	Approved
0.6477	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD3195	Phase 2
0.6471	Remote Similarity	NPD3196	Approved
0.6471	Remote Similarity	NPD4266	Approved
0.6471	Remote Similarity	NPD3194	Approved
0.6322	Remote Similarity	NPD5690	Phase 2
0.6322	Remote Similarity	NPD5279	Phase 3
0.6304	Remote Similarity	NPD5695	Phase 3
0.6292	Remote Similarity	NPD4753	Phase 2
0.6279	Remote Similarity	NPD4197	Approved
0.6207	Remote Similarity	NPD5329	Approved
0.6207	Remote Similarity	NPD1696	Phase 3
0.618	Remote Similarity	NPD6672	Approved
0.618	Remote Similarity	NPD5737	Approved
0.617	Remote Similarity	NPD6083	Phase 2
0.617	Remote Similarity	NPD6084	Phase 2
0.6163	Remote Similarity	NPD7154	Phase 3
0.6136	Remote Similarity	NPD4694	Approved
0.6136	Remote Similarity	NPD5280	Approved
0.6136	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6129	Remote Similarity	NPD5210	Approved
0.6129	Remote Similarity	NPD4629	Approved
0.6105	Remote Similarity	NPD5696	Approved
0.6092	Remote Similarity	NPD3666	Approved
0.6092	Remote Similarity	NPD3665	Phase 1
0.6092	Remote Similarity	NPD3133	Approved
0.6064	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6064	Remote Similarity	NPD5222	Approved
0.6064	Remote Similarity	NPD5221	Approved
0.6047	Remote Similarity	NPD4221	Approved
0.6047	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.6047	Remote Similarity	NPD4223	Phase 3
0.6047	Remote Similarity	NPD3667	Approved
0.6029	Remote Similarity	NPD29	Approved
0.6029	Remote Similarity	NPD28	Approved
0.6023	Remote Similarity	NPD5363	Approved
0.6	Remote Similarity	NPD5173	Approved
0.6	Remote Similarity	NPD9090	Phase 3
0.597	Remote Similarity	NPD3173	Approved
0.5955	Remote Similarity	NPD3618	Phase 1
0.5934	Remote Similarity	NPD6080	Approved
0.5934	Remote Similarity	NPD6904	Approved
0.5934	Remote Similarity	NPD6673	Approved
0.593	Remote Similarity	NPD5369	Approved
0.5909	Remote Similarity	NPD4786	Approved
0.5895	Remote Similarity	NPD4697	Phase 3
0.5876	Remote Similarity	NPD5286	Approved
0.5876	Remote Similarity	NPD4696	Approved
0.5876	Remote Similarity	NPD5285	Approved
0.587	Remote Similarity	NPD6698	Approved
0.587	Remote Similarity	NPD5692	Phase 3
0.587	Remote Similarity	NPD5785	Approved
0.587	Remote Similarity	NPD46	Approved
0.5851	Remote Similarity	NPD7748	Approved
0.5842	Remote Similarity	NPD5697	Approved
0.5833	Remote Similarity	NPD4755	Approved
0.5824	Remote Similarity	NPD4518	Approved
0.5821	Remote Similarity	NPD622	Approved
0.5816	Remote Similarity	NPD5223	Approved
0.5806	Remote Similarity	NPD7515	Phase 2
0.5806	Remote Similarity	NPD6050	Approved
0.5806	Remote Similarity	NPD5693	Phase 1
0.5806	Remote Similarity	NPD5694	Approved
0.5806	Remote Similarity	NPD6079	Approved
0.5795	Remote Similarity	NPD5362	Discontinued
0.5784	Remote Similarity	NPD6881	Approved
0.5784	Remote Similarity	NPD6899	Approved
0.5784	Remote Similarity	NPD6011	Approved
0.5778	Remote Similarity	NPD4689	Approved
0.5778	Remote Similarity	NPD4688	Approved
0.5778	Remote Similarity	NPD4693	Phase 3
0.5778	Remote Similarity	NPD4519	Discontinued
0.5778	Remote Similarity	NPD4690	Approved
0.5778	Remote Similarity	NPD4138	Approved
0.5778	Remote Similarity	NPD4623	Approved
0.5778	Remote Similarity	NPD5205	Approved
0.5761	Remote Similarity	NPD5328	Approved
0.5761	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.5761	Remote Similarity	NPD6101	Approved
0.5758	Remote Similarity	NPD5226	Approved
0.5758	Remote Similarity	NPD5211	Phase 2
0.5758	Remote Similarity	NPD4633	Approved
0.5758	Remote Similarity	NPD5224	Approved
0.5758	Remote Similarity	NPD5225	Approved
0.5745	Remote Similarity	NPD6399	Phase 3
0.5745	Remote Similarity	NPD5133	Approved
0.5743	Remote Similarity	NPD6675	Approved
0.5743	Remote Similarity	NPD5739	Approved
0.5743	Remote Similarity	NPD6402	Approved
0.5743	Remote Similarity	NPD7128	Approved
0.573	Remote Similarity	NPD3668	Phase 3
0.5728	Remote Similarity	NPD6014	Approved
0.5728	Remote Similarity	NPD6013	Approved
0.5728	Remote Similarity	NPD6012	Approved
0.5714	Remote Similarity	NPD4700	Approved
0.57	Remote Similarity	NPD5175	Approved
0.57	Remote Similarity	NPD5174	Approved
0.5686	Remote Similarity	NPD5701	Approved
0.5682	Remote Similarity	NPD4269	Approved
0.5682	Remote Similarity	NPD6435	Approved
0.5682	Remote Similarity	NPD4270	Approved
0.5682	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.5679	Remote Similarity	NPD4691	Approved
0.5676	Remote Similarity	NPD6109	Phase 1
0.5673	Remote Similarity	NPD6883	Approved
0.5673	Remote Similarity	NPD7102	Approved
0.5673	Remote Similarity	NPD7290	Approved
0.567	Remote Similarity	NPD7902	Approved
0.5667	Remote Similarity	NPD1694	Approved
0.5644	Remote Similarity	NPD5141	Approved
0.5638	Remote Similarity	NPD5284	Approved
0.5638	Remote Similarity	NPD5281	Approved
0.5638	Remote Similarity	NPD6411	Approved
0.5636	Remote Similarity	NPD7299	Clinical (unspecified phase)
0.5632	Remote Similarity	NPD4252	Approved
0.5632	Remote Similarity	NPD5368	Approved
0.5631	Remote Similarity	NPD7320	Approved
0.5625	Remote Similarity	NPD5654	Approved
0.5625	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.5619	Remote Similarity	NPD8130	Phase 1
0.5619	Remote Similarity	NPD6650	Approved
0.5619	Remote Similarity	NPD6869	Approved
0.5619	Remote Similarity	NPD6847	Approved
0.5619	Remote Similarity	NPD6617	Approved
0.5619	Remote Similarity	NPD6649	Approved
0.5604	Remote Similarity	NPD6422	Discontinued
0.5604	Remote Similarity	NPD6098	Approved
0.5604	Remote Similarity	NPD5330	Approved
0.5604	Remote Similarity	NPD7146	Approved
0.5604	Remote Similarity	NPD7521	Approved
0.5604	Remote Similarity	NPD7334	Approved
0.5604	Remote Similarity	NPD6684	Approved
0.5604	Remote Similarity	NPD6409	Approved
0.5604	Remote Similarity	NPD5786	Approved
0.56	Remote Similarity	NPD5091	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