NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	196.07
Volume:	197.575
LogP:	2.319
LogD:	2.068
LogS:	-2.252
# Rotatable Bonds:	2
TPSA:	77.76
# H-Bond Aceptor:	4
# H-Bond Donor:	3
# Rings:	1
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.628
Synthetic Accessibility Score:	2.402
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:	-4.71
MDCK Permeability:	1.2951197277288884e-05
Pgp-inhibitor:	0.002
Pgp-substrate:	0.008
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.87
30% Bioavailability (F30%):	0.703

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.067
Plasma Protein Binding (PPB):	94.84020233154297%
Volume Distribution (VD):	0.651
Pgp-substrate:	4.312237739562988%

ADMET: Metabolism

CYP1A2-inhibitor:	0.943
CYP1A2-substrate:	0.705
CYP2C19-inhibitor:	0.127
CYP2C19-substrate:	0.062
CYP2C9-inhibitor:	0.435
CYP2C9-substrate:	0.855
CYP2D6-inhibitor:	0.744
CYP2D6-substrate:	0.333
CYP3A4-inhibitor:	0.762
CYP3A4-substrate:	0.185

ADMET: Excretion

Clearance (CL):	12.054
Half-life (T1/2):	0.815

ADMET: Toxicity

hERG Blockers:	0.023
Human Hepatotoxicity (H-HT):	0.046
Drug-inuced Liver Injury (DILI):	0.779
AMES Toxicity:	0.607
Rat Oral Acute Toxicity:	0.065
Maximum Recommended Daily Dose:	0.278
Skin Sensitization:	0.889
Carcinogencity:	0.058
Eye Corrosion:	0.039
Eye Irritation:	0.938
Respiratory Toxicity:	0.605

Download Data

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

Natural Product: NPC294037

Natural Product ID:	NPC294037
*Common Name:**	Phloroisobutyrophenone
IUPAC Name:	2-methyl-1-(2,4,6-trihydroxyphenyl)propan-1-one
Synonyms:	phloroisobutyrophenone
Standard InCHIKey:	BNEBXEZRBLYBCZ-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C10H12O4/c1-5(2)10(14)9-7(12)3-6(11)4-8(9)13/h3-5,11-13H,1-2H3
SMILES:	Oc1cc(O)c(c(c1)O)C(=O)C(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL20038
PubChem CID:	5326317
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
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1007/s11746-997-0093-1]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	n.a.	Wrocław, Poland	2004–2005	DOI[10.1016/J.FOODCHEM.2006.08.014]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	n.a.	retail stores, supermarkets and market stalls in Forssa and in the Helsinki area	2003–2005	DOI[10.1016/j.jfca.2006.05.007]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1021/jf950732o]
NPO13879	Humulus lupulus	Species	Cannabaceae	Eukaryota	n.a.	cone	n.a.	PMID[10336650]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10775096]
NPO26880	Mallotus japonicus	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11520216]
NPO15976	Hypericum calycinum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15649510]
NPO13879	Humulus lupulus	Species	Cannabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15679315]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	n.a.	root	n.a.	PMID[1622242]
NPO13879	Humulus lupulus	Species	Cannabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16252923]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16659156]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16668466]
NPO13879	Humulus lupulus	Species	Cannabaceae	Eukaryota	n.a.	cone	n.a.	PMID[17624889]
NPO26880	Mallotus japonicus	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1800639]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18460139]
NPO13879	Humulus lupulus	Species	Cannabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18611049]
NPO13879	Humulus lupulus	Species	Cannabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18768384]
NPO13879	Humulus lupulus	Species	Cannabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19476340]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20963508]
NPO13879	Humulus lupulus	Species	Cannabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21912858]
NPO13879	Humulus lupulus	Species	Cannabaceae	Eukaryota	n.a.	cone	n.a.	PMID[22111577]
NPO13879	Humulus lupulus	Species	Cannabaceae	Eukaryota	n.a.	flower	n.a.	PMID[22166201]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22537213]
NPO26880	Mallotus japonicus	Species	Euphorbiaceae	Eukaryota	n.a.	pericarp	n.a.	PMID[2347013]
NPO31247	Hypericum gentianoides	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23600727]
NPO13879	Humulus lupulus	Species	Cannabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23790907]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	Seeds	Tekirdag, Turkey		PMID[24499198]
NPO13879	Humulus lupulus	Species	Cannabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24948953]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25053043]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25070365]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	n.a.	seed	n.a.	PMID[25369450]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25369450]
NPO13879	Humulus lupulus	Species	Cannabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25564559]
NPO1795	Fragaria vesca	Species	Rosaceae	Eukaryota	n.a.	fruit	n.a.	PMID[26169681]
NPO13879	Humulus lupulus	Species	Cannabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[29154541]
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]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	Cotyledon	n.a.	n.a.	Database[FooDB]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	Hypocotyl	n.a.	n.a.	Database[FooDB]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	Oil	n.a.	n.a.	Database[FooDB]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	Pericarp	n.a.	n.a.	Database[FooDB]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	Root	n.a.	n.a.	Database[FooDB]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	Sprout Seedling	n.a.	n.a.	Database[FooDB]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	Stem	n.a.	n.a.	Database[FooDB]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	Testa	n.a.	n.a.	Database[FooDB]
NPO1795	Fragaria vesca	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15976	Hypericum calycinum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26880	Mallotus japonicus	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13879	Humulus lupulus	Species	Cannabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[MetaboLights]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	n.a.	seed	n.a.	Database[MetaboLights]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	Seeds	n.a.		Database[Phenol-Explorer]
NPO15976	Hypericum calycinum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26880	Mallotus japonicus	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1795	Fragaria vesca	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13879	Humulus lupulus	Species	Cannabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO13879	Humulus lupulus	Species	Cannabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO13879	Humulus lupulus	Species	Cannabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO26880	Mallotus japonicus	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15976	Hypericum calycinum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13879	Humulus lupulus	Species	Cannabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1795	Fragaria vesca	Species	Rosaceae	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	2
Others	4

Activity Type	# Activity
Individual Protein	1
Organism	4
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT324	Individual Protein	Cyclooxygenase-1	Ovis aries	IC50	=	3800.0	nM	PMID[532818]
NPT938	Organism	Cavia porcellus	Cavia porcellus	Inhibition	=	11.0	%	PMID[532817]
NPT938	Organism	Cavia porcellus	Cavia porcellus	Inhibition	=	70.4	%	PMID[532817]
NPT938	Organism	Cavia porcellus	Cavia porcellus	IC50	=	6600.0	nM	PMID[532817]
NPT938	Organism	Cavia porcellus	Cavia porcellus	Inhibition	=	32.0	%	PMID[532817]
NPT610	Others	Molecular identity unknown		GI	<	50.0	%	PMID[532819]

☑ 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 NPC294037 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	306
0.1-0.2	1537
0.2-0.3	4266
0.3-0.4	11914
0.4-0.5	7304
0.5-0.6	5588
0.6-0.7	6762
0.7-0.8	4126
0.8-0.85	611
0.85-0.9	202
0.9-0.95	67
0.95-1	14

Similarity Score	Similarity Level	Natural Product ID
0.9912	High Similarity	NPC146642
0.9821	High Similarity	NPC209486
0.9821	High Similarity	NPC40649
0.9737	High Similarity	NPC149246
0.9655	High Similarity	NPC472029
0.9655	High Similarity	NPC65761
0.9652	High Similarity	NPC215392
0.9569	High Similarity	NPC91105
0.9561	High Similarity	NPC161617
0.9492	High Similarity	NPC475733
0.9483	High Similarity	NPC242895
0.9483	High Similarity	NPC226275
0.9402	High Similarity	NPC32032
0.9402	High Similarity	NPC133909
0.9402	High Similarity	NPC309765
0.9316	High Similarity	NPC115159
0.9316	High Similarity	NPC19174
0.9316	High Similarity	NPC143427
0.9316	High Similarity	NPC73532
0.9316	High Similarity	NPC45438
0.9316	High Similarity	NPC156139
0.9316	High Similarity	NPC267552
0.9316	High Similarity	NPC224273
0.9316	High Similarity	NPC303737
0.9292	High Similarity	NPC118288
0.9292	High Similarity	NPC276111
0.9256	High Similarity	NPC473017
0.925	High Similarity	NPC267846
0.9231	High Similarity	NPC297186
0.9217	High Similarity	NPC121259
0.918	High Similarity	NPC212379
0.918	High Similarity	NPC69235
0.9174	High Similarity	NPC23126
0.9174	High Similarity	NPC72158
0.9174	High Similarity	NPC162612
0.9174	High Similarity	NPC169250
0.9174	High Similarity	NPC103356
0.9174	High Similarity	NPC116513
0.9174	High Similarity	NPC190043
0.9174	High Similarity	NPC100067
0.9174	High Similarity	NPC266689
0.9174	High Similarity	NPC105157
0.9174	High Similarity	NPC30501
0.9174	High Similarity	NPC98254
0.9167	High Similarity	NPC477454
0.9167	High Similarity	NPC10926
0.9153	High Similarity	NPC196976
0.9145	High Similarity	NPC159525
0.9098	High Similarity	NPC21305
0.9098	High Similarity	NPC221777
0.9091	High Similarity	NPC62952
0.9091	High Similarity	NPC473691
0.9091	High Similarity	NPC8745
0.9083	High Similarity	NPC13238
0.906	High Similarity	NPC158222
0.9052	High Similarity	NPC230349
0.9024	High Similarity	NPC474998
0.9016	High Similarity	NPC305518
0.9016	High Similarity	NPC128428
0.9008	High Similarity	NPC201728
0.9008	High Similarity	NPC262671
0.8974	High Similarity	NPC241089
0.896	High Similarity	NPC175738
0.8943	High Similarity	NPC41263
0.8898	High Similarity	NPC195262
0.8898	High Similarity	NPC188814
0.888	High Similarity	NPC475042
0.888	High Similarity	NPC324482
0.8871	High Similarity	NPC102829
0.8871	High Similarity	NPC476119
0.8871	High Similarity	NPC230818
0.8871	High Similarity	NPC92624
0.8871	High Similarity	NPC120488
0.8871	High Similarity	NPC109123
0.8814	High Similarity	NPC283844
0.881	High Similarity	NPC27490
0.88	High Similarity	NPC84772
0.88	High Similarity	NPC247477
0.88	High Similarity	NPC233056
0.88	High Similarity	NPC17840
0.88	High Similarity	NPC259942
0.879	High Similarity	NPC80694
0.879	High Similarity	NPC186098
0.878	High Similarity	NPC328983
0.878	High Similarity	NPC95309
0.876	High Similarity	NPC218333
0.875	High Similarity	NPC229649
0.875	High Similarity	NPC236974
0.875	High Similarity	NPC248363
0.875	High Similarity	NPC144027
0.874	High Similarity	NPC139074
0.874	High Similarity	NPC25937
0.874	High Similarity	NPC40524
0.874	High Similarity	NPC213485
0.874	High Similarity	NPC48036
0.874	High Similarity	NPC267205
0.873	High Similarity	NPC270369
0.873	High Similarity	NPC275504
0.873	High Similarity	NPC5515
0.873	High Similarity	NPC198249
0.871	High Similarity	NPC329205
0.871	High Similarity	NPC316625
0.8707	High Similarity	NPC223004
0.8689	High Similarity	NPC306288
0.8682	High Similarity	NPC475955
0.8682	High Similarity	NPC474726
0.8672	High Similarity	NPC159623
0.8672	High Similarity	NPC108113
0.8672	High Similarity	NPC294593
0.8672	High Similarity	NPC204960
0.8672	High Similarity	NPC82225
0.8672	High Similarity	NPC166480
0.8672	High Similarity	NPC20560
0.8672	High Similarity	NPC474519
0.8672	High Similarity	NPC144051
0.8672	High Similarity	NPC18877
0.8672	High Similarity	NPC28753
0.8672	High Similarity	NPC93756
0.8672	High Similarity	NPC475088
0.8672	High Similarity	NPC282780
0.8661	High Similarity	NPC262359
0.8661	High Similarity	NPC31872
0.8661	High Similarity	NPC473584
0.8661	High Similarity	NPC135801
0.8661	High Similarity	NPC475589
0.8661	High Similarity	NPC313618
0.8651	High Similarity	NPC62219
0.8651	High Similarity	NPC26697
0.8651	High Similarity	NPC147757
0.864	High Similarity	NPC293453
0.864	High Similarity	NPC179898
0.864	High Similarity	NPC470981
0.8615	High Similarity	NPC156910
0.8615	High Similarity	NPC213603
0.8615	High Similarity	NPC470398
0.8615	High Similarity	NPC470397
0.8615	High Similarity	NPC187826
0.8607	High Similarity	NPC66252
0.8607	High Similarity	NPC232708
0.8605	High Similarity	NPC286336
0.8605	High Similarity	NPC70859
0.8605	High Similarity	NPC290803
0.8605	High Similarity	NPC61153
0.8605	High Similarity	NPC125920
0.8605	High Similarity	NPC470210
0.8605	High Similarity	NPC164136
0.8605	High Similarity	NPC283590
0.8605	High Similarity	NPC130899
0.8596	High Similarity	NPC224584
0.8594	High Similarity	NPC87231
0.8594	High Similarity	NPC257756
0.8594	High Similarity	NPC180261
0.8594	High Similarity	NPC205468
0.8594	High Similarity	NPC37299
0.8594	High Similarity	NPC203817
0.8594	High Similarity	NPC10971
0.8594	High Similarity	NPC212631
0.8594	High Similarity	NPC129132
0.8583	High Similarity	NPC469526
0.8583	High Similarity	NPC219892
0.8583	High Similarity	NPC189823
0.8583	High Similarity	NPC34070
0.855	High Similarity	NPC153979
0.8547	High Similarity	NPC242136
0.8538	High Similarity	NPC13575
0.8538	High Similarity	NPC84699
0.8538	High Similarity	NPC65005
0.8538	High Similarity	NPC131039
0.8538	High Similarity	NPC191976
0.8538	High Similarity	NPC264112
0.8538	High Similarity	NPC254847
0.8538	High Similarity	NPC194764
0.8538	High Similarity	NPC60667
0.8527	High Similarity	NPC192304
0.8527	High Similarity	NPC175098
0.8527	High Similarity	NPC472365
0.8527	High Similarity	NPC337373
0.8527	High Similarity	NPC242294
0.8527	High Similarity	NPC188646
0.8527	High Similarity	NPC223457
0.8527	High Similarity	NPC139813
0.8527	High Similarity	NPC312318
0.8527	High Similarity	NPC263670
0.8527	High Similarity	NPC56031
0.8527	High Similarity	NPC44437
0.8522	High Similarity	NPC95172
0.8516	High Similarity	NPC475008
0.8516	High Similarity	NPC64359
0.8516	High Similarity	NPC478190
0.8516	High Similarity	NPC185624
0.8516	High Similarity	NPC186097
0.8516	High Similarity	NPC475009
0.8516	High Similarity	NPC308037
0.8512	High Similarity	NPC294964
0.8509	High Similarity	NPC226699
0.8504	High Similarity	NPC21378
0.8504	High Similarity	NPC42292
0.8504	High Similarity	NPC470987
0.8504	High Similarity	NPC185497
0.8504	High Similarity	NPC307732

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 NPC294037 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	299
0.1-0.2	974
0.2-0.3	1630
0.3-0.4	2933
0.4-0.5	1886
0.5-0.6	1029
0.6-0.7	298
0.7-0.8	89
0.8-0.85	11
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8661	High Similarity	NPD943	Approved
0.8661	High Similarity	NPD1240	Approved
0.8538	High Similarity	NPD1509	Clinical (unspecified phase)
0.8527	High Similarity	NPD1607	Approved
0.8397	Intermediate Similarity	NPD1510	Phase 2
0.8271	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8271	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8258	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.8209	Intermediate Similarity	NPD1549	Phase 2
0.8209	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.812	Intermediate Similarity	NPD9266	Approved
0.812	Intermediate Similarity	NPD74	Approved
0.807	Intermediate Similarity	NPD846	Approved
0.807	Intermediate Similarity	NPD940	Approved
0.8043	Intermediate Similarity	NPD7390	Discontinued
0.8034	Intermediate Similarity	NPD9267	Approved
0.8034	Intermediate Similarity	NPD9263	Approved
0.8034	Intermediate Similarity	NPD9264	Approved
0.8034	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.8033	Intermediate Similarity	NPD9493	Approved
0.7986	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7984	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.797	Intermediate Similarity	NPD6651	Approved
0.7937	Intermediate Similarity	NPD1201	Approved
0.7874	Intermediate Similarity	NPD9269	Phase 2
0.7857	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.784	Intermediate Similarity	NPD9268	Approved
0.7829	Intermediate Similarity	NPD1470	Approved
0.7829	Intermediate Similarity	NPD1164	Approved
0.7786	Intermediate Similarity	NPD1511	Approved
0.776	Intermediate Similarity	NPD9545	Approved
0.7754	Intermediate Similarity	NPD2800	Approved
0.7742	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7724	Intermediate Similarity	NPD9281	Approved
0.7692	Intermediate Similarity	NPD9261	Approved
0.7676	Intermediate Similarity	NPD1512	Approved
0.7664	Intermediate Similarity	NPD2796	Approved
0.763	Intermediate Similarity	NPD230	Phase 1
0.7619	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7603	Intermediate Similarity	NPD1934	Approved
0.7597	Intermediate Similarity	NPD9717	Approved
0.7586	Intermediate Similarity	NPD4380	Phase 2
0.7571	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7551	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7535	Intermediate Similarity	NPD6799	Approved
0.7534	Intermediate Similarity	NPD7411	Suspended
0.75	Intermediate Similarity	NPD1243	Approved
0.75	Intermediate Similarity	NPD2654	Approved
0.7483	Intermediate Similarity	NPD2532	Approved
0.7483	Intermediate Similarity	NPD2533	Approved
0.7483	Intermediate Similarity	NPD2534	Approved
0.7459	Intermediate Similarity	NPD4750	Phase 3
0.7447	Intermediate Similarity	NPD3750	Approved
0.7432	Intermediate Similarity	NPD2801	Approved
0.7424	Intermediate Similarity	NPD1203	Approved
0.741	Intermediate Similarity	NPD2935	Discontinued
0.741	Intermediate Similarity	NPD5405	Approved
0.741	Intermediate Similarity	NPD5404	Approved
0.741	Intermediate Similarity	NPD1551	Phase 2
0.741	Intermediate Similarity	NPD5406	Approved
0.741	Intermediate Similarity	NPD5408	Approved
0.74	Intermediate Similarity	NPD7075	Discontinued
0.7357	Intermediate Similarity	NPD2344	Approved
0.7347	Intermediate Similarity	NPD6599	Discontinued
0.7333	Intermediate Similarity	NPD3882	Suspended
0.7315	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD7819	Suspended
0.7285	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7285	Intermediate Similarity	NPD3749	Approved
0.7279	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7252	Intermediate Similarity	NPD422	Phase 1
0.7248	Intermediate Similarity	NPD6801	Discontinued
0.7239	Intermediate Similarity	NPD2798	Approved
0.7227	Intermediate Similarity	NPD1242	Phase 1
0.7214	Intermediate Similarity	NPD2799	Discontinued
0.7179	Intermediate Similarity	NPD7473	Discontinued
0.7163	Intermediate Similarity	NPD6099	Approved
0.7163	Intermediate Similarity	NPD6100	Approved
0.7153	Intermediate Similarity	NPD2309	Approved
0.7143	Intermediate Similarity	NPD6959	Discontinued
0.7143	Intermediate Similarity	NPD920	Approved
0.7133	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD6166	Phase 2
0.7105	Intermediate Similarity	NPD7768	Phase 2
0.7103	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD520	Approved
0.7097	Intermediate Similarity	NPD6232	Discontinued
0.7092	Intermediate Similarity	NPD3748	Approved
0.7039	Intermediate Similarity	NPD3817	Phase 2
0.7034	Intermediate Similarity	NPD2860	Approved
0.7034	Intermediate Similarity	NPD1809	Phase 2
0.7034	Intermediate Similarity	NPD2859	Approved
0.7029	Intermediate Similarity	NPD411	Approved
0.7029	Intermediate Similarity	NPD3764	Approved
0.7029	Intermediate Similarity	NPD3268	Approved
0.7009	Intermediate Similarity	NPD845	Approved
0.7007	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD447	Suspended
0.7	Intermediate Similarity	NPD3020	Approved
0.6992	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6986	Remote Similarity	NPD3300	Phase 2
0.6981	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD256	Approved
0.6977	Remote Similarity	NPD255	Approved
0.6975	Remote Similarity	NPD288	Approved
0.697	Remote Similarity	NPD3019	Approved
0.697	Remote Similarity	NPD2932	Approved
0.6966	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6949	Remote Similarity	NPD2934	Approved
0.6949	Remote Similarity	NPD1432	Clinical (unspecified phase)
0.6949	Remote Similarity	NPD2933	Approved
0.6947	Remote Similarity	NPD1759	Phase 1
0.694	Remote Similarity	NPD3972	Approved
0.6937	Remote Similarity	NPD7074	Phase 3
0.6918	Remote Similarity	NPD3818	Discontinued
0.6914	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6913	Remote Similarity	NPD5403	Approved
0.6912	Remote Similarity	NPD2797	Approved
0.6911	Remote Similarity	NPD1237	Approved
0.6906	Remote Similarity	NPD1296	Phase 2
0.6906	Remote Similarity	NPD2313	Discontinued
0.6903	Remote Similarity	NPD111	Approved
0.6894	Remote Similarity	NPD5953	Discontinued
0.6892	Remote Similarity	NPD5401	Approved
0.6891	Remote Similarity	NPD844	Approved
0.6884	Remote Similarity	NPD6832	Phase 2
0.6883	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD7054	Approved
0.6875	Remote Similarity	NPD7286	Phase 2
0.6875	Remote Similarity	NPD6020	Phase 2
0.687	Remote Similarity	NPD1758	Phase 1
0.6866	Remote Similarity	NPD1610	Phase 2
0.6861	Remote Similarity	NPD1019	Discontinued
0.6859	Remote Similarity	NPD5494	Approved
0.6832	Remote Similarity	NPD7472	Approved
0.6822	Remote Similarity	NPD1241	Discontinued
0.6818	Remote Similarity	NPD1548	Phase 1
0.6815	Remote Similarity	NPD1608	Approved
0.6812	Remote Similarity	NPD9494	Approved
0.6803	Remote Similarity	NPD289	Clinical (unspecified phase)
0.6795	Remote Similarity	NPD919	Approved
0.679	Remote Similarity	NPD6797	Phase 2
0.6788	Remote Similarity	NPD3266	Approved
0.6788	Remote Similarity	NPD3267	Approved
0.6772	Remote Similarity	NPD5710	Approved
0.6772	Remote Similarity	NPD5711	Approved
0.6765	Remote Similarity	NPD1755	Approved
0.6763	Remote Similarity	NPD4908	Phase 1
0.6753	Remote Similarity	NPD1465	Phase 2
0.6752	Remote Similarity	NPD9256	Approved
0.6752	Remote Similarity	NPD9258	Approved
0.6748	Remote Similarity	NPD7251	Discontinued
0.6736	Remote Similarity	NPD3299	Clinical (unspecified phase)
0.6736	Remote Similarity	NPD4308	Phase 3
0.6735	Remote Similarity	NPD4628	Phase 3
0.6728	Remote Similarity	NPD1729	Discontinued
0.6715	Remote Similarity	NPD1876	Approved
0.6711	Remote Similarity	NPD3226	Approved
0.6709	Remote Similarity	NPD1247	Approved
0.6707	Remote Similarity	NPD7808	Phase 3
0.6696	Remote Similarity	NPD9093	Approved
0.6693	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6689	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD9568	Approved
0.6667	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD6559	Discontinued
0.6644	Remote Similarity	NPD2346	Discontinued
0.6642	Remote Similarity	NPD4749	Approved
0.6641	Remote Similarity	NPD3022	Approved
0.6641	Remote Similarity	NPD3021	Approved
0.6637	Remote Similarity	NPD9089	Approved
0.6625	Remote Similarity	NPD3926	Phase 2
0.6622	Remote Similarity	NPD1196	Approved
0.6621	Remote Similarity	NPD7033	Discontinued
0.6606	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6603	Remote Similarity	NPD2296	Approved
0.6603	Remote Similarity	NPD8438	Clinical (unspecified phase)
0.6603	Remote Similarity	NPD5402	Approved
0.6601	Remote Similarity	NPD7458	Discontinued
0.66	Remote Similarity	NPD1543	Discontinued
0.6594	Remote Similarity	NPD3225	Approved
0.6593	Remote Similarity	NPD17	Approved
0.6584	Remote Similarity	NPD2403	Approved
0.6573	Remote Similarity	NPD468	Phase 1
0.6571	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6569	Remote Similarity	NPD1481	Phase 2
0.656	Remote Similarity	NPD1930	Approved
0.656	Remote Similarity	NPD1929	Approved
0.656	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.6554	Remote Similarity	NPD1195	Approved
0.6552	Remote Similarity	NPD9279	Approved
0.6545	Remote Similarity	NPD6104	Discontinued
0.6544	Remote Similarity	NPD3026	Approved
0.6544	Remote Similarity	NPD3023	Approved
0.6538	Remote Similarity	NPD6124	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD1609	Clinical (unspecified phase)

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