NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	196.07
Volume:	197.575
LogP:	2.311
LogD:	1.662
LogS:	-2.431
# Rotatable Bonds:	2
TPSA:	66.76
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	1
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.705
Synthetic Accessibility Score:	2.266
Fsp3:	0.3
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.775
MDCK Permeability:	1.2209464330226183e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.004
Human Intestinal Absorption (HIA):	0.014
20% Bioavailability (F20%):	0.017
30% Bioavailability (F30%):	0.005

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.118
Plasma Protein Binding (PPB):	94.73707580566406%
Volume Distribution (VD):	0.735
Pgp-substrate:	5.825477123260498%

ADMET: Metabolism

CYP1A2-inhibitor:	0.911
CYP1A2-substrate:	0.918
CYP2C19-inhibitor:	0.149
CYP2C19-substrate:	0.444
CYP2C9-inhibitor:	0.242
CYP2C9-substrate:	0.767
CYP2D6-inhibitor:	0.273
CYP2D6-substrate:	0.498
CYP3A4-inhibitor:	0.19
CYP3A4-substrate:	0.267

ADMET: Excretion

Clearance (CL):	11.083
Half-life (T1/2):	0.738

ADMET: Toxicity

hERG Blockers:	0.025
Human Hepatotoxicity (H-HT):	0.047
Drug-inuced Liver Injury (DILI):	0.6
AMES Toxicity:	0.128
Rat Oral Acute Toxicity:	0.309
Maximum Recommended Daily Dose:	0.339
Skin Sensitization:	0.617
Carcinogencity:	0.108
Eye Corrosion:	0.086
Eye Irritation:	0.967
Respiratory Toxicity:	0.78

Download Data

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

Natural Product: NPC230818

Natural Product ID:	NPC230818
*Common Name:**	2,6-Dihydroxy-3-Methyl-4-Methoxyacetophenone
IUPAC Name:	1-(2,6-dihydroxy-4-methoxy-3-methylphenyl)ethanone
Synonyms:
Standard InCHIKey:	LWIPTFGZKUVFKC-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C10H12O4/c1-5-8(14-3)4-7(12)9(6(2)11)10(5)13/h4,12-13H,1-3H3
SMILES:	Cc1c(cc(c(C(=O)C)c1O)O)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL505640
PubChem CID:	14602300
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0001831] Carbonyl compounds [CHEMONTID:0000118] Ketones [CHEMONTID:0003670] Aryl ketones [CHEMONTID:0004296] Phenylketones [CHEMONTID:0004298] Alkyl-phenylketones

*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
NPO25715	Senna siamea	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10757709]
NPO2130	Ehretia dicksonii	Species	Ehretiaceae	Eukaryota	n.a.	leaf	n.a.	PMID[10830513]
NPO2130	Ehretia dicksonii	Species	Ehretiaceae	Eukaryota	n.a.	twig	n.a.	PMID[10830513]
NPO2130	Ehretia dicksonii	Species	Ehretiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10830513]
NPO26880	Mallotus japonicus	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11520216]
NPO6774	Khaya senegalensis	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12193039]
NPO25715	Senna siamea	Species	Fabaceae	Eukaryota	n.a.	leaf	n.a.	PMID[17685627]
NPO26880	Mallotus japonicus	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1800639]
NPO1103	Dioscorea japonica	Species	Dioscoreaceae	Eukaryota	rhizomes	n.a.	n.a.	PMID[21353549]
NPO13504	Lotus japonicus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21510636]
NPO25715	Senna siamea	Species	Fabaceae	Eukaryota	Stems	n.a.	n.a.	PMID[23078294]
NPO6774	Khaya senegalensis	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23210623]
NPO26880	Mallotus japonicus	Species	Euphorbiaceae	Eukaryota	n.a.	pericarp	n.a.	PMID[2347013]
NPO25715	Senna siamea	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23513740]
NPO14089	Hypericum ascyron	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[30379546]
NPO14089	Hypericum ascyron	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31596079]
NPO26880	Mallotus japonicus	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[3210017]
NPO26880	Mallotus japonicus	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[3734813]
NPO26880	Mallotus japonicus	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[4040956]
NPO25809	Helleborus niger	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1103	Dioscorea japonica	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26880	Mallotus japonicus	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14089	Hypericum ascyron	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13907	Senecio renardii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25774	Virola multinervia	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14089	Hypericum ascyron	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25715	Senna siamea	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25809	Helleborus niger	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25774	Virola multinervia	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3199	Balanophora involucrata	Species	Balanophoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26880	Mallotus japonicus	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1103	Dioscorea japonica	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13907	Senecio renardii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14089	Hypericum ascyron	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO1103	Dioscorea japonica	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO10389	Larix cajanderi	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25715	Senna siamea	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6179	Aframomum amaniense	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10865	Sextonia rubra	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13701	Melaleuca rhaphiophylla	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11882	Cedrus libani	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12069	Isaria felina	Species	Cordycipitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3458	Lupinus verbasciformis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1661	Bartramia pomiformis	Species	Bartramiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14615	Streptomyces paulus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO13907	Senecio renardii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12234	Khaya ivorensis	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12910	Ixeris stolonifera	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6774	Khaya senegalensis	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13504	Lotus japonicus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14200	Aristolochia zollingeriana	Species	Aristolochiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21498	Coccus ilicis	Species	Coccidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13076	Cephalaria grossheimii	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26880	Mallotus japonicus	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14504	Alectoria divergens	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25511	Streptomyces ghanaensis	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO9669	Dictyopteris acrostichoides	Species	Dictyotaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12061	Justicia paniculata	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12754	Cerinthe minor	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2130	Ehretia dicksonii	Species	Ehretiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14289	Pieris napi	Species	Pieridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3199	Balanophora involucrata	Species	Balanophoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25809	Helleborus niger	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10012	Triaenophora rupestris	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25774	Virola multinervia	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7169	Nama hispidum	Species	Namaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14089	Hypericum ascyron	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12585	Craspidospermum verticillatum	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7752	Beilschmiedia anacardioides	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1103	Dioscorea japonica	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12414	Penicillium paxilli	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22010	Dasyscyphus nidulus	Species	Hyaloscyphaceae	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
ED50	4
IC50	1
Others	3

Activity Type	# Activity
Cell Line	4
Individual Protein	1
NON-MOLECULAR	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	ED50	>	100.0	ug ml-1	PMID[485186]
NPT1864	Cell Line	L5178Y	Mus musculus	ED50	>	100.0	ug ml-1	PMID[485186]
NPT91	Cell Line	KB	Homo sapiens	ED50	>	100.0	ug ml-1	PMID[485187]
NPT1864	Cell Line	L5178Y	Mus musculus	ED50	>	100.0	ug ml-1	PMID[485187]
NPT178	Individual Protein	Protein-tyrosine phosphatase 1B	Homo sapiens	IC50	>	200000.0	nM	PMID[485188]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	100.0	%	PMID[485185]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	49.5	%	PMID[485185]

☑ 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 NPC230818 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	338
0.1-0.2	1659
0.2-0.3	4894
0.3-0.4	11837
0.4-0.5	6056
0.5-0.6	4568
0.6-0.7	5958
0.7-0.8	4975
0.8-0.85	1452
0.85-0.9	661
0.9-0.95	281
0.95-1	18

Similarity Score	Similarity Level	Natural Product ID
0.9919	High Similarity	NPC84772
0.9839	High Similarity	NPC324482
0.976	High Similarity	NPC27490
0.9677	High Similarity	NPC212379
0.9677	High Similarity	NPC69235
0.9675	High Similarity	NPC305518
0.9675	High Similarity	NPC128428
0.9531	High Similarity	NPC164136
0.9531	High Similarity	NPC125920
0.9457	High Similarity	NPC13575
0.9457	High Similarity	NPC60667
0.9457	High Similarity	NPC84699
0.9453	High Similarity	NPC93756
0.9453	High Similarity	NPC108113
0.944	High Similarity	NPC186098
0.944	High Similarity	NPC80694
0.9385	High Similarity	NPC249606
0.9385	High Similarity	NPC98115
0.9385	High Similarity	NPC186838
0.9385	High Similarity	NPC1486
0.9385	High Similarity	NPC222633
0.9385	High Similarity	NPC12165
0.9385	High Similarity	NPC477242
0.9385	High Similarity	NPC168105
0.9385	High Similarity	NPC41461
0.9385	High Similarity	NPC25287
0.9385	High Similarity	NPC156910
0.9385	High Similarity	NPC477243
0.9385	High Similarity	NPC274109
0.9385	High Similarity	NPC150399
0.9385	High Similarity	NPC477244
0.9385	High Similarity	NPC174999
0.9385	High Similarity	NPC66349
0.938	High Similarity	NPC103842
0.937	High Similarity	NPC250057
0.9313	High Similarity	NPC317119
0.9313	High Similarity	NPC472419
0.9313	High Similarity	NPC153979
0.9308	High Similarity	NPC156092
0.9308	High Similarity	NPC131039
0.9302	High Similarity	NPC28753
0.9302	High Similarity	NPC20560
0.9302	High Similarity	NPC294593
0.9302	High Similarity	NPC82225
0.9302	High Similarity	NPC204960
0.9302	High Similarity	NPC18877
0.9302	High Similarity	NPC144051
0.9302	High Similarity	NPC159623
0.9297	High Similarity	NPC313618
0.9297	High Similarity	NPC31872
0.9297	High Similarity	NPC473584
0.9297	High Similarity	NPC475589
0.9286	High Similarity	NPC293453
0.9242	High Similarity	NPC477056
0.9242	High Similarity	NPC21350
0.9242	High Similarity	NPC477055
0.9242	High Similarity	NPC251681
0.9242	High Similarity	NPC131130
0.9242	High Similarity	NPC243528
0.9231	High Similarity	NPC236974
0.9231	High Similarity	NPC286336
0.9231	High Similarity	NPC144027
0.9225	High Similarity	NPC103105
0.9225	High Similarity	NPC25937
0.9225	High Similarity	NPC257756
0.9225	High Similarity	NPC212631
0.9225	High Similarity	NPC129132
0.9225	High Similarity	NPC285054
0.9225	High Similarity	NPC215875
0.9225	High Similarity	NPC205468
0.9225	High Similarity	NPC15834
0.9225	High Similarity	NPC87231
0.9225	High Similarity	NPC203817
0.9219	High Similarity	NPC5515
0.9219	High Similarity	NPC270369
0.9173	High Similarity	NPC78913
0.9173	High Similarity	NPC18260
0.9173	High Similarity	NPC472366
0.9173	High Similarity	NPC23257
0.9173	High Similarity	NPC477956
0.9173	High Similarity	NPC37206
0.9173	High Similarity	NPC470211
0.9173	High Similarity	NPC471697
0.9173	High Similarity	NPC295384
0.9173	High Similarity	NPC139554
0.9173	High Similarity	NPC473076
0.916	High Similarity	NPC151113
0.9154	High Similarity	NPC223457
0.9154	High Similarity	NPC472365
0.9154	High Similarity	NPC263670
0.9154	High Similarity	NPC188646
0.9154	High Similarity	NPC242294
0.9154	High Similarity	NPC337373
0.9154	High Similarity	NPC175098
0.9154	High Similarity	NPC192304
0.9154	High Similarity	NPC56031
0.9154	High Similarity	NPC312318
0.9154	High Similarity	NPC139813
0.9154	High Similarity	NPC16197
0.9154	High Similarity	NPC27643
0.9147	High Similarity	NPC475008
0.9147	High Similarity	NPC64359
0.9147	High Similarity	NPC186097
0.9147	High Similarity	NPC475009
0.9147	High Similarity	NPC308037
0.9147	High Similarity	NPC262359
0.9141	High Similarity	NPC186628
0.9141	High Similarity	NPC185497
0.9141	High Similarity	NPC42292
0.9141	High Similarity	NPC307732
0.9104	High Similarity	NPC172250
0.9104	High Similarity	NPC253822
0.9104	High Similarity	NPC215311
0.9104	High Similarity	NPC144118
0.9104	High Similarity	NPC80962
0.9104	High Similarity	NPC326109
0.9104	High Similarity	NPC241100
0.9104	High Similarity	NPC219917
0.9104	High Similarity	NPC48624
0.9104	High Similarity	NPC471587
0.9104	High Similarity	NPC101366
0.9104	High Similarity	NPC11056
0.9104	High Similarity	NPC16455
0.9104	High Similarity	NPC204985
0.9104	High Similarity	NPC213659
0.9104	High Similarity	NPC259166
0.9104	High Similarity	NPC159275
0.9104	High Similarity	NPC307990
0.9098	High Similarity	NPC474504
0.9098	High Similarity	NPC201395
0.9098	High Similarity	NPC470668
0.9098	High Similarity	NPC470669
0.9098	High Similarity	NPC471620
0.9098	High Similarity	NPC470671
0.9098	High Similarity	NPC470672
0.9098	High Similarity	NPC474487
0.9091	High Similarity	NPC470397
0.9091	High Similarity	NPC187826
0.9091	High Similarity	NPC470398
0.9077	High Similarity	NPC10971
0.907	High Similarity	NPC279566
0.9062	High Similarity	NPC78662
0.9062	High Similarity	NPC8005
0.9062	High Similarity	NPC60558
0.9048	High Similarity	NPC65041
0.9037	High Similarity	NPC279650
0.9037	High Similarity	NPC3188
0.9037	High Similarity	NPC94076
0.9037	High Similarity	NPC258630
0.9037	High Similarity	NPC470089
0.9037	High Similarity	NPC26051
0.9037	High Similarity	NPC156190
0.9037	High Similarity	NPC52789
0.9037	High Similarity	NPC469404
0.9037	High Similarity	NPC324386
0.9037	High Similarity	NPC282300
0.9037	High Similarity	NPC312391
0.9037	High Similarity	NPC171870
0.9037	High Similarity	NPC470087
0.9037	High Similarity	NPC96408
0.9037	High Similarity	NPC26238
0.9037	High Similarity	NPC4743
0.9037	High Similarity	NPC213322
0.9037	High Similarity	NPC110969
0.9037	High Similarity	NPC268204
0.9037	High Similarity	NPC182255
0.9037	High Similarity	NPC17170
0.9037	High Similarity	NPC321980
0.9037	High Similarity	NPC166689
0.9037	High Similarity	NPC55832
0.9032	High Similarity	NPC215392
0.9032	High Similarity	NPC226275
0.903	High Similarity	NPC303633
0.903	High Similarity	NPC217186
0.903	High Similarity	NPC283429
0.903	High Similarity	NPC216978
0.903	High Similarity	NPC165172
0.903	High Similarity	NPC55018
0.903	High Similarity	NPC96565
0.903	High Similarity	NPC220062
0.903	High Similarity	NPC53181
0.903	High Similarity	NPC301217
0.903	High Similarity	NPC137009
0.9023	High Similarity	NPC162680
0.9023	High Similarity	NPC116632
0.9023	High Similarity	NPC181124
0.9023	High Similarity	NPC7013
0.9023	High Similarity	NPC209560
0.9023	High Similarity	NPC294409
0.9023	High Similarity	NPC303644
0.9015	High Similarity	NPC39426
0.9015	High Similarity	NPC101752
0.9015	High Similarity	NPC234560
0.9	High Similarity	NPC164236
0.9	High Similarity	NPC112192
0.9	High Similarity	NPC128348
0.9	High Similarity	NPC66384
0.9	High Similarity	NPC65060
0.9	High Similarity	NPC189106
0.9	High Similarity	NPC309717

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 NPC230818 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	309
0.1-0.2	1045
0.2-0.3	1768
0.3-0.4	2751
0.4-0.5	1715
0.5-0.6	1085
0.6-0.7	332
0.7-0.8	116
0.8-0.85	20
0.85-0.9	7
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9297	High Similarity	NPD1240	Approved
0.9154	High Similarity	NPD1607	Approved
0.9015	High Similarity	NPD1510	Phase 2
0.8881	High Similarity	NPD1552	Clinical (unspecified phase)
0.8881	High Similarity	NPD1550	Clinical (unspecified phase)
0.8864	High Similarity	NPD6651	Approved
0.8841	High Similarity	NPD4378	Clinical (unspecified phase)
0.8815	High Similarity	NPD1549	Phase 2
0.8676	High Similarity	NPD970	Clinical (unspecified phase)
0.8613	High Similarity	NPD2800	Approved
0.8571	High Similarity	NPD7410	Clinical (unspecified phase)
0.8403	Intermediate Similarity	NPD4380	Phase 2
0.8356	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8345	Intermediate Similarity	NPD7411	Suspended
0.831	Intermediate Similarity	NPD2532	Approved
0.831	Intermediate Similarity	NPD2533	Approved
0.831	Intermediate Similarity	NPD2534	Approved
0.8299	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8261	Intermediate Similarity	NPD2796	Approved
0.8239	Intermediate Similarity	NPD1511	Approved
0.8214	Intermediate Similarity	NPD1243	Approved
0.8188	Intermediate Similarity	NPD7075	Discontinued
0.8163	Intermediate Similarity	NPD6801	Discontinued
0.8163	Intermediate Similarity	NPD1934	Approved
0.8156	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.8129	Intermediate Similarity	NPD2935	Discontinued
0.8125	Intermediate Similarity	NPD1512	Approved
0.8112	Intermediate Similarity	NPD6799	Approved
0.8108	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8108	Intermediate Similarity	NPD7819	Suspended
0.8085	Intermediate Similarity	NPD2654	Approved
0.8069	Intermediate Similarity	NPD920	Approved
0.8058	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.8026	Intermediate Similarity	NPD6959	Discontinued
0.8	Intermediate Similarity	NPD1551	Phase 2
0.7987	Intermediate Similarity	NPD2801	Approved
0.7969	Intermediate Similarity	NPD9493	Approved
0.7958	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7955	Intermediate Similarity	NPD9717	Approved
0.7917	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7905	Intermediate Similarity	NPD6599	Discontinued
0.7902	Intermediate Similarity	NPD3750	Approved
0.7899	Intermediate Similarity	NPD943	Approved
0.7883	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7881	Intermediate Similarity	NPD3882	Suspended
0.7881	Intermediate Similarity	NPD7768	Phase 2
0.7871	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD6232	Discontinued
0.7846	Intermediate Similarity	NPD9545	Approved
0.7829	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7821	Intermediate Similarity	NPD7473	Discontinued
0.7808	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD1203	Approved
0.7744	Intermediate Similarity	NPD422	Phase 1
0.7722	Intermediate Similarity	NPD7286	Phase 2
0.7722	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7714	Intermediate Similarity	NPD230	Phase 1
0.7712	Intermediate Similarity	NPD3749	Approved
0.7692	Intermediate Similarity	NPD2344	Approved
0.7676	Intermediate Similarity	NPD2799	Discontinued
0.7643	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7643	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7643	Intermediate Similarity	NPD6166	Phase 2
0.7625	Intermediate Similarity	NPD5953	Discontinued
0.7619	Intermediate Similarity	NPD7390	Discontinued
0.7582	Intermediate Similarity	NPD3817	Phase 2
0.7562	Intermediate Similarity	NPD1729	Discontinued
0.7552	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7552	Intermediate Similarity	NPD3748	Approved
0.7548	Intermediate Similarity	NPD919	Approved
0.7531	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7519	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD5711	Approved
0.7516	Intermediate Similarity	NPD5710	Approved
0.75	Intermediate Similarity	NPD2313	Discontinued
0.75	Intermediate Similarity	NPD5494	Approved
0.75	Intermediate Similarity	NPD6100	Approved
0.75	Intermediate Similarity	NPD6099	Approved
0.7483	Intermediate Similarity	NPD2309	Approved
0.7481	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7467	Intermediate Similarity	NPD5403	Approved
0.7464	Intermediate Similarity	NPD2798	Approved
0.7453	Intermediate Similarity	NPD7074	Phase 3
0.7452	Intermediate Similarity	NPD1247	Approved
0.745	Intermediate Similarity	NPD5401	Approved
0.7444	Intermediate Similarity	NPD1548	Phase 1
0.7438	Intermediate Similarity	NPD3818	Discontinued
0.7426	Intermediate Similarity	NPD3972	Approved
0.7419	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7415	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD1164	Approved
0.7391	Intermediate Similarity	NPD7054	Approved
0.7376	Intermediate Similarity	NPD1296	Phase 2
0.7376	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7376	Intermediate Similarity	NPD411	Approved
0.7368	Intermediate Similarity	NPD3226	Approved
0.7362	Intermediate Similarity	NPD6559	Discontinued
0.7357	Intermediate Similarity	NPD6832	Phase 2
0.7353	Intermediate Similarity	NPD1610	Phase 2
0.7353	Intermediate Similarity	NPD1201	Approved
0.7346	Intermediate Similarity	NPD7472	Approved
0.7344	Intermediate Similarity	NPD74	Approved
0.7344	Intermediate Similarity	NPD9266	Approved
0.7343	Intermediate Similarity	NPD447	Suspended
0.7338	Intermediate Similarity	NPD1019	Discontinued
0.7328	Intermediate Similarity	NPD1241	Discontinued
0.7301	Intermediate Similarity	NPD6797	Phase 2
0.7297	Intermediate Similarity	NPD4628	Phase 3
0.729	Intermediate Similarity	NPD1465	Phase 2
0.7286	Intermediate Similarity	NPD9494	Approved
0.728	Intermediate Similarity	NPD846	Approved
0.728	Intermediate Similarity	NPD940	Approved
0.7266	Intermediate Similarity	NPD9264	Approved
0.7266	Intermediate Similarity	NPD9267	Approved
0.7266	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7266	Intermediate Similarity	NPD1470	Approved
0.7266	Intermediate Similarity	NPD9263	Approved
0.7256	Intermediate Similarity	NPD7251	Discontinued
0.7254	Intermediate Similarity	NPD3268	Approved
0.7237	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7234	Intermediate Similarity	NPD4908	Phase 1
0.7222	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD5124	Phase 1
0.7212	Intermediate Similarity	NPD7808	Phase 3
0.7211	Intermediate Similarity	NPD2346	Discontinued
0.7192	Intermediate Similarity	NPD7033	Discontinued
0.7178	Intermediate Similarity	NPD5844	Phase 1
0.7174	Intermediate Similarity	NPD1608	Approved
0.7174	Intermediate Similarity	NPD9269	Phase 2
0.7152	Intermediate Similarity	NPD6104	Discontinued
0.7143	Intermediate Similarity	NPD3926	Phase 2
0.7143	Intermediate Similarity	NPD2797	Approved
0.7143	Intermediate Similarity	NPD7458	Discontinued
0.7134	Intermediate Similarity	NPD5402	Approved
0.7132	Intermediate Similarity	NPD9268	Approved
0.7108	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD2403	Approved
0.7093	Intermediate Similarity	NPD4360	Phase 2
0.7093	Intermediate Similarity	NPD4363	Phase 3
0.708	Intermediate Similarity	NPD4626	Approved
0.7075	Intermediate Similarity	NPD4308	Phase 3
0.7071	Intermediate Similarity	NPD3225	Approved
0.7071	Intermediate Similarity	NPD1876	Approved
0.7071	Intermediate Similarity	NPD1283	Approved
0.7067	Intermediate Similarity	NPD7003	Approved
0.7052	Intermediate Similarity	NPD4361	Phase 2
0.7052	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7042	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD5405	Approved
0.7027	Intermediate Similarity	NPD5408	Approved
0.7027	Intermediate Similarity	NPD5404	Approved
0.7027	Intermediate Similarity	NPD5406	Approved
0.7021	Intermediate Similarity	NPD3267	Approved
0.7021	Intermediate Similarity	NPD3266	Approved
0.7015	Intermediate Similarity	NPD9281	Approved
0.7014	Intermediate Similarity	NPD3764	Approved
0.7011	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD1651	Approved
0.7	Intermediate Similarity	NPD4749	Approved
0.6993	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD1008	Clinical (unspecified phase)
0.6988	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6986	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6986	Remote Similarity	NPD1933	Approved
0.698	Remote Similarity	NPD1471	Phase 3
0.6972	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD17	Approved
0.6953	Remote Similarity	NPD9261	Approved
0.6944	Remote Similarity	NPD3027	Phase 3
0.6944	Remote Similarity	NPD4625	Phase 3
0.6929	Remote Similarity	NPD1481	Phase 2
0.6928	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD2296	Approved
0.6918	Remote Similarity	NPD1613	Approved
0.6918	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD4288	Approved
0.6897	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD6005	Phase 3
0.6867	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD6004	Phase 3
0.6867	Remote Similarity	NPD6002	Phase 3
0.6867	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD1281	Approved
0.6857	Remote Similarity	NPD1535	Discovery
0.6835	Remote Similarity	NPD1778	Approved
0.6821	Remote Similarity	NPD2424	Discontinued
0.6803	Remote Similarity	NPD3142	Approved
0.6803	Remote Similarity	NPD4307	Phase 2
0.6803	Remote Similarity	NPD3140	Approved
0.6798	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6797	Remote Similarity	NPD2354	Approved
0.6792	Remote Similarity	NPD37	Approved
0.6786	Remote Similarity	NPD3847	Discontinued
0.6781	Remote Similarity	NPD6798	Discontinued
0.6776	Remote Similarity	NPD1652	Phase 2

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data