NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	178.06
Volume:	186.148
LogP:	1.468
LogD:	1.416
LogS:	-0.877
# Rotatable Bonds:	2
TPSA:	57.53
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	1
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.535
Synthetic Accessibility Score:	2.159
Fsp3:	0.1
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.634
MDCK Permeability:	1.9578634237404913e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.223
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.006

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.111
Plasma Protein Binding (PPB):	93.27381134033203%
Volume Distribution (VD):	0.321
Pgp-substrate:	4.776515960693359%

ADMET: Metabolism

CYP1A2-inhibitor:	0.63
CYP1A2-substrate:	0.363
CYP2C19-inhibitor:	0.074
CYP2C19-substrate:	0.065
CYP2C9-inhibitor:	0.141
CYP2C9-substrate:	0.721
CYP2D6-inhibitor:	0.05
CYP2D6-substrate:	0.568
CYP3A4-inhibitor:	0.166
CYP3A4-substrate:	0.198

ADMET: Excretion

Clearance (CL):	14.757
Half-life (T1/2):	0.911

ADMET: Toxicity

hERG Blockers:	0.023
Human Hepatotoxicity (H-HT):	0.281
Drug-inuced Liver Injury (DILI):	0.229
AMES Toxicity:	0.589
Rat Oral Acute Toxicity:	0.907
Maximum Recommended Daily Dose:	0.631
Skin Sensitization:	0.953
Carcinogencity:	0.753
Eye Corrosion:	0.583
Eye Irritation:	0.973
Respiratory Toxicity:	0.808

Download Data

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

Natural Product: NPC79672

Natural Product ID:	NPC79672
*Common Name:**	3,4-Dihydroxybenzalacetone
IUPAC Name:	(E)-4-(3,4-dihydroxyphenyl)but-3-en-2-one
Synonyms:
Standard InCHIKey:	YIFZKRGUGKLILR-NSCUHMNNSA-N
Standard InCHI:	InChI=1S/C10H10O3/c1-7(11)2-3-8-4-5-9(12)10(13)6-8/h2-6,12-13H,1H3/b3-2+
SMILES:	CC(=O)/C=C/c1ccc(c(c1)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL75390
PubChem CID:	9942292
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000476] Cinnamic acids and derivatives [CHEMONTID:0001391] Hydroxycinnamic acids and derivatives

*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
NPO24588	Phellinus igniarius	Species	Hymenochaetaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15165144]
NPO24588	Phellinus igniarius	Species	Hymenochaetaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15844878]
NPO24588	Phellinus igniarius	Species	Hymenochaetaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16209522]
NPO16039	Scutellaria barbata	Species	Lamiaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[16755060]
NPO18766	Inonotus obliquus	Species	Hymenochaetaceae	Eukaryota	sclerotia	n.a.	n.a.	PMID[17049251]
NPO24588	Phellinus igniarius	Species	Hymenochaetaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17279797]
NPO16039	Scutellaria barbata	Species	Lamiaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[17666848]
NPO16039	Scutellaria barbata	Species	Lamiaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[18239311]
NPO18766	Inonotus obliquus	Species	Hymenochaetaceae	Eukaryota	sclerotia	n.a.	n.a.	PMID[18387711]
NPO16039	Scutellaria barbata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19785430]
NPO16039	Scutellaria barbata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19962306]
NPO16039	Scutellaria barbata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20078074]
NPO24588	Phellinus igniarius	Species	Hymenochaetaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20583752]
NPO18766	Inonotus obliquus	Species	Hymenochaetaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24359303]
NPO16039	Scutellaria barbata	Species	Lamiaceae	Eukaryota	whole plants	Nanning District, Guangxi Province, China	2012-Sep	PMID[25647077]
NPO16039	Scutellaria barbata	Species	Lamiaceae	Eukaryota	aerial parts	Seoul, Korea	n.a.	PMID[26331882]
NPO21355	Elsholtzia ciliata	Species	Lamiaceae	Eukaryota	Aerial Parts	n.a.	n.a.	PMID[32991171]
NPO16039	Scutellaria barbata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24588	Phellinus igniarius	Species	Hymenochaetaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21355	Elsholtzia ciliata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13213	Inonotus hispidus	Species	Hymenochaetaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24588	Phellinus igniarius	Species	Hymenochaetaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16039	Scutellaria barbata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13213	Inonotus hispidus	Species	Hymenochaetaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21355	Elsholtzia ciliata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21355	Elsholtzia ciliata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO24588	Phellinus igniarius	Species	Hymenochaetaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO16039	Scutellaria barbata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO21355	Elsholtzia ciliata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO16039	Scutellaria barbata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO18766	Inonotus obliquus	Species	Hymenochaetaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21355	Elsholtzia ciliata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24588	Phellinus igniarius	Species	Hymenochaetaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16039	Scutellaria barbata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13213	Inonotus hispidus	Species	Hymenochaetaceae	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
EC50	1
IC50	15
LD50	7
Others	23

Activity Type	# Activity
Cell Line	15
CELL-LINE	11
Individual Protein	1
NON-MOLECULAR	1
Organism	3
Others	15

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	IC50	>	280.0	nM	PMID[493141]
NPT547	Cell Line	BGC-823	Homo sapiens	IC50	=	243.0	nM	PMID[493141]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	141.0	nM	PMID[493141]
NPT181	Cell Line	Bel-7402	Homo sapiens	IC50	=	153.0	nM	PMID[493141]
NPT1085	Cell Line	KETR3	Homo sapiens	IC50	=	245.0	nM	PMID[493141]
NPT180	Cell Line	HCT-8	Homo sapiens	IC50	=	227.0	nM	PMID[493141]
NPT91	Cell Line	KB	Homo sapiens	IC50	>	10000.0	nM	PMID[493142]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	10000.0	nM	PMID[493142]
NPT30	Individual Protein	Cyclooxygenase-1	Homo sapiens	IC50	=	22200.0	nM	PMID[493143]
NPT941	Cell Line	HaCaT	Homo sapiens	LD50	=	3500.0	uM	PMID[493144]
NPT886	Cell Line	NIH3T3	Mus musculus	LD50	>	5000.0	uM	PMID[493144]
NPT113	Cell Line	RAW264.7	Mus musculus	LD50	=	500.0	uM	PMID[493144]
NPT196	Cell Line	AGS	Homo sapiens	LD50	=	60.0	uM	PMID[493144]
NPT306	Cell Line	PC-3	Homo sapiens	LD50	=	66.0	uM	PMID[493144]
NPT169	Cell Line	B16-F10	Mus musculus	LD50	=	65.0	uM	PMID[493144]
NPT804	Cell Line	HT-22	Mus musculus	EC50	=	1500.0	nM	PMID[493145]
NPT19	Organism	Escherichia coli	Escherichia coli	IC50	=	977237.22	nM	PMID[493139]
NPT419	Organism	Oryctolagus cuniculus	Oryctolagus cuniculus	IC50	=	27542287033381.75	nM	PMID[493140]
NPT419	Organism	Oryctolagus cuniculus	Oryctolagus cuniculus	IC50	=	2338.84	nM	PMID[493140]
NPT2	Others	Unspecified		IC50	=	7700.0	nM	PMID[493142]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	4700.0	nM	PMID[493142]
NPT2	Others	Unspecified		IC50	=	7800.0	nM	PMID[493144]
NPT2	Others	Unspecified		Inhibition	=	100.0	%	PMID[493144]
NPT2	Others	Unspecified		Activity	<=	59.0	%	PMID[493144]
NPT21334	CELL-LINE	MC3T3-E1	Mus musculus	Activity	=	100.0	%	PMID[493144]
NPT21334	CELL-LINE	MC3T3-E1	Mus musculus	Activity	=	110.0	%	PMID[493144]
NPT21334	CELL-LINE	MC3T3-E1	Mus musculus	Activity	=	120.0	%	PMID[493144]
NPT21334	CELL-LINE	MC3T3-E1	Mus musculus	Activity	=	280.0	%	PMID[493144]
NPT21334	CELL-LINE	MC3T3-E1	Mus musculus	FC	=	1.8	n.a.	PMID[493144]
NPT21334	CELL-LINE	MC3T3-E1	Mus musculus	FC	=	4.1	n.a.	PMID[493144]
NPT21334	CELL-LINE	MC3T3-E1	Mus musculus	FC	=	2.0	n.a.	PMID[493144]
NPT27	Others	Unspecified		T1/2	=	0.4	hr	PMID[493144]
NPT27	Others	Unspecified		T1/2	=	2.1	hr	PMID[493144]
NPT27	Others	Unspecified		T1/2	=	3.1	hr	PMID[493144]
NPT27	Others	Unspecified		Cmax	=	200.0	nM	PMID[493144]
NPT27	Others	Unspecified		Cmax	=	1100.0	nM	PMID[493144]
NPT27	Others	Unspecified		AUC	=	0.039	uM.hr	PMID[493144]
NPT27	Others	Unspecified		AUC	=	0.14	uM.hr	PMID[493144]
NPT27	Others	Unspecified		AUC	=	0.66	uM.hr	PMID[493144]
NPT27	Others	Unspecified		F	=	66.0	%	PMID[493144]
NPT27	Others	Unspecified		F	=	76.0	%	PMID[493144]
NPT21334	CELL-LINE	MC3T3-E1	Mus musculus	FC	=	1.7	n.a.	PMID[493144]
NPT21334	CELL-LINE	MC3T3-E1	Mus musculus	FC	=	1.4	n.a.	PMID[493144]
NPT21334	CELL-LINE	MC3T3-E1	Mus musculus	FC	=	3.2	n.a.	PMID[493144]
NPT2	Others	Unspecified		LD50	=	2800.0	uM	PMID[493144]

☑ 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 NPC79672 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	232
0.1-0.2	2108
0.2-0.3	6022
0.3-0.4	13229
0.4-0.5	4803
0.5-0.6	9159
0.6-0.7	5701
0.7-0.8	1251
0.8-0.85	139
0.85-0.9	41
0.9-0.95	10
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9794	High Similarity	NPC52087
0.94	High Similarity	NPC19149
0.94	High Similarity	NPC1075
0.94	High Similarity	NPC1786
0.94	High Similarity	NPC294902
0.9271	High Similarity	NPC107522
0.9135	High Similarity	NPC297657
0.9135	High Similarity	NPC226250
0.9082	High Similarity	NPC109955
0.9062	High Similarity	NPC181709
0.9048	High Similarity	NPC51698
0.899	High Similarity	NPC131587
0.8962	High Similarity	NPC95381
0.8911	High Similarity	NPC196479
0.89	High Similarity	NPC223393
0.8879	High Similarity	NPC33749
0.8879	High Similarity	NPC261453
0.8879	High Similarity	NPC328593
0.8824	High Similarity	NPC120719
0.8812	High Similarity	NPC110764
0.8807	High Similarity	NPC150919
0.8796	High Similarity	NPC233669
0.8796	High Similarity	NPC474967
0.8716	High Similarity	NPC281277
0.8716	High Similarity	NPC61062
0.8716	High Similarity	NPC277394
0.8716	High Similarity	NPC299252
0.8704	High Similarity	NPC217472
0.8692	High Similarity	NPC131530
0.8687	High Similarity	NPC257182
0.8654	High Similarity	NPC477814
0.8649	High Similarity	NPC117759
0.8641	High Similarity	NPC12278
0.8641	High Similarity	NPC471511
0.8636	High Similarity	NPC65791
0.8636	High Similarity	NPC39793
0.8586	High Similarity	NPC81010
0.8586	High Similarity	NPC32977
0.8559	High Similarity	NPC203124
0.8559	High Similarity	NPC70744
0.8559	High Similarity	NPC272471
0.8559	High Similarity	NPC107588
0.8559	High Similarity	NPC137537
0.8559	High Similarity	NPC164706
0.8559	High Similarity	NPC309434
0.8558	High Similarity	NPC239291
0.8544	High Similarity	NPC477801
0.8544	High Similarity	NPC477802
0.8515	High Similarity	NPC201967
0.8505	High Similarity	NPC222084
0.85	High Similarity	NPC286006
0.8496	Intermediate Similarity	NPC189844
0.8496	Intermediate Similarity	NPC109083
0.8496	Intermediate Similarity	NPC269843
0.8496	Intermediate Similarity	NPC60962
0.8496	Intermediate Similarity	NPC224814
0.8496	Intermediate Similarity	NPC14007
0.8468	Intermediate Similarity	NPC278652
0.8447	Intermediate Similarity	NPC94343
0.844	Intermediate Similarity	NPC148969
0.844	Intermediate Similarity	NPC264558
0.8431	Intermediate Similarity	NPC130193
0.8411	Intermediate Similarity	NPC7097
0.8411	Intermediate Similarity	NPC246358
0.8411	Intermediate Similarity	NPC254833
0.8411	Intermediate Similarity	NPC36108
0.8411	Intermediate Similarity	NPC233731
0.8411	Intermediate Similarity	NPC228343
0.8407	Intermediate Similarity	NPC202474
0.8396	Intermediate Similarity	NPC176527
0.8393	Intermediate Similarity	NPC275519
0.835	Intermediate Similarity	NPC253746
0.8348	Intermediate Similarity	NPC114298
0.8348	Intermediate Similarity	NPC286573
0.8333	Intermediate Similarity	NPC158949
0.8333	Intermediate Similarity	NPC470849
0.8333	Intermediate Similarity	NPC248817
0.8333	Intermediate Similarity	NPC470848
0.8333	Intermediate Similarity	NPC204466
0.8333	Intermediate Similarity	NPC150837
0.8319	Intermediate Similarity	NPC241634
0.8319	Intermediate Similarity	NPC263386
0.8319	Intermediate Similarity	NPC141791
0.8318	Intermediate Similarity	NPC58427
0.8318	Intermediate Similarity	NPC105727
0.8318	Intermediate Similarity	NPC114392
0.8318	Intermediate Similarity	NPC233835
0.8318	Intermediate Similarity	NPC34864
0.8288	Intermediate Similarity	NPC278102
0.8276	Intermediate Similarity	NPC160900
0.8276	Intermediate Similarity	NPC18984
0.8276	Intermediate Similarity	NPC257976
0.8276	Intermediate Similarity	NPC229084
0.8276	Intermediate Similarity	NPC164778
0.8276	Intermediate Similarity	NPC242372
0.8276	Intermediate Similarity	NPC106659
0.8276	Intermediate Similarity	NPC4181
0.8276	Intermediate Similarity	NPC238810
0.8269	Intermediate Similarity	NPC472585
0.8265	Intermediate Similarity	NPC27974
0.8261	Intermediate Similarity	NPC70752
0.8257	Intermediate Similarity	NPC257124
0.8257	Intermediate Similarity	NPC470355
0.8257	Intermediate Similarity	NPC78918
0.8257	Intermediate Similarity	NPC173746
0.8257	Intermediate Similarity	NPC8547
0.8257	Intermediate Similarity	NPC156840
0.8257	Intermediate Similarity	NPC139617
0.8247	Intermediate Similarity	NPC197783
0.8246	Intermediate Similarity	NPC2058
0.8241	Intermediate Similarity	NPC55617
0.8241	Intermediate Similarity	NPC62258
0.823	Intermediate Similarity	NPC212743
0.8229	Intermediate Similarity	NPC265146
0.8229	Intermediate Similarity	NPC124436
0.8224	Intermediate Similarity	NPC34715
0.8205	Intermediate Similarity	NPC312404
0.8205	Intermediate Similarity	NPC273686
0.8198	Intermediate Similarity	NPC294941
0.819	Intermediate Similarity	NPC304638
0.819	Intermediate Similarity	NPC68269
0.819	Intermediate Similarity	NPC135784
0.819	Intermediate Similarity	NPC86900
0.8182	Intermediate Similarity	NPC231717
0.8174	Intermediate Similarity	NPC236520
0.8174	Intermediate Similarity	NPC294361
0.8165	Intermediate Similarity	NPC226401
0.8165	Intermediate Similarity	NPC120982
0.8165	Intermediate Similarity	NPC79793
0.8165	Intermediate Similarity	NPC174096
0.8165	Intermediate Similarity	NPC147634
0.8163	Intermediate Similarity	NPC184169
0.8163	Intermediate Similarity	NPC23167
0.8158	Intermediate Similarity	NPC299406
0.8155	Intermediate Similarity	NPC260000
0.8144	Intermediate Similarity	NPC175313
0.8142	Intermediate Similarity	NPC175799
0.8142	Intermediate Similarity	NPC610
0.8142	Intermediate Similarity	NPC145023
0.8142	Intermediate Similarity	NPC200988
0.8142	Intermediate Similarity	NPC280001
0.8137	Intermediate Similarity	NPC274678
0.8137	Intermediate Similarity	NPC246679
0.8136	Intermediate Similarity	NPC142776
0.8136	Intermediate Similarity	NPC197832
0.8131	Intermediate Similarity	NPC6984
0.8125	Intermediate Similarity	NPC4665
0.812	Intermediate Similarity	NPC306100
0.8113	Intermediate Similarity	NPC93831
0.8103	Intermediate Similarity	NPC147654
0.8091	Intermediate Similarity	NPC268032
0.8091	Intermediate Similarity	NPC257430
0.8091	Intermediate Similarity	NPC187583
0.8091	Intermediate Similarity	NPC179002
0.8081	Intermediate Similarity	NPC104216
0.8081	Intermediate Similarity	NPC19680
0.8081	Intermediate Similarity	NPC25493
0.8081	Intermediate Similarity	NPC113460
0.8077	Intermediate Similarity	NPC280869
0.807	Intermediate Similarity	NPC86198
0.8067	Intermediate Similarity	NPC276014
0.8067	Intermediate Similarity	NPC179777
0.8058	Intermediate Similarity	NPC283711
0.8056	Intermediate Similarity	NPC226699
0.8051	Intermediate Similarity	NPC20443
0.8051	Intermediate Similarity	NPC146886
0.8051	Intermediate Similarity	NPC246704
0.8051	Intermediate Similarity	NPC60517
0.8037	Intermediate Similarity	NPC303141
0.8036	Intermediate Similarity	NPC142599
0.802	Intermediate Similarity	NPC270547
0.802	Intermediate Similarity	NPC231150
0.802	Intermediate Similarity	NPC155908
0.802	Intermediate Similarity	NPC304541
0.8019	Intermediate Similarity	NPC470202
0.8018	Intermediate Similarity	NPC146422
0.8017	Intermediate Similarity	NPC98305
0.8	Intermediate Similarity	NPC123228
0.8	Intermediate Similarity	NPC123273
0.8	Intermediate Similarity	NPC32163
0.8	Intermediate Similarity	NPC242240
0.8	Intermediate Similarity	NPC179309
0.8	Intermediate Similarity	NPC177420
0.8	Intermediate Similarity	NPC5018
0.8	Intermediate Similarity	NPC70084
0.8	Intermediate Similarity	NPC123722
0.8	Intermediate Similarity	NPC280347
0.8	Intermediate Similarity	NPC156654
0.8	Intermediate Similarity	NPC109371
0.8	Intermediate Similarity	NPC258219
0.8	Intermediate Similarity	NPC318325
0.8	Intermediate Similarity	NPC470214
0.8	Intermediate Similarity	NPC151167
0.8	Intermediate Similarity	NPC470215
0.8	Intermediate Similarity	NPC276466
0.8	Intermediate Similarity	NPC98772
0.8	Intermediate Similarity	NPC16651
0.7983	Intermediate Similarity	NPC300326
0.7983	Intermediate Similarity	NPC289459
0.7983	Intermediate Similarity	NPC58279

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 NPC79672 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	238
0.1-0.2	1126
0.2-0.3	1486
0.3-0.4	3097
0.4-0.5	1801
0.5-0.6	1054
0.6-0.7	286
0.7-0.8	58
0.8-0.85	2
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8411	Intermediate Similarity	NPD3022	Approved
0.8411	Intermediate Similarity	NPD3021	Approved
0.8276	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.8257	Intermediate Similarity	NPD228	Approved
0.8229	Intermediate Similarity	NPD111	Approved
0.8018	Intermediate Similarity	NPD9379	Approved
0.8018	Intermediate Similarity	NPD9377	Approved
0.7864	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.7864	Intermediate Similarity	NPD2933	Approved
0.7864	Intermediate Similarity	NPD2934	Approved
0.7851	Intermediate Similarity	NPD9494	Approved
0.7838	Intermediate Similarity	NPD9280	Clinical (unspecified phase)
0.783	Intermediate Similarity	NPD1242	Phase 1
0.7788	Intermediate Similarity	NPD2859	Approved
0.7788	Intermediate Similarity	NPD844	Approved
0.7788	Intermediate Similarity	NPD2860	Approved
0.7736	Intermediate Similarity	NPD3020	Approved
0.7714	Intermediate Similarity	NPD288	Approved
0.7672	Intermediate Similarity	NPD5536	Phase 2
0.7664	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.7583	Intermediate Similarity	NPD9269	Phase 2
0.754	Intermediate Similarity	NPD943	Approved
0.748	Intermediate Similarity	NPD257	Approved
0.748	Intermediate Similarity	NPD258	Approved
0.7479	Intermediate Similarity	NPD9384	Approved
0.7479	Intermediate Similarity	NPD9381	Approved
0.7431	Intermediate Similarity	NPD940	Approved
0.7431	Intermediate Similarity	NPD846	Approved
0.7411	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7377	Intermediate Similarity	NPD9622	Approved
0.7344	Intermediate Similarity	NPD230	Phase 1
0.7317	Intermediate Similarity	NPD9634	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7295	Intermediate Similarity	NPD2337	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD1809	Phase 2
0.7288	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7282	Intermediate Similarity	NPD9094	Approved
0.728	Intermediate Similarity	NPD9569	Approved
0.7264	Intermediate Similarity	NPD845	Approved
0.7258	Intermediate Similarity	NPD3055	Approved
0.7258	Intermediate Similarity	NPD3053	Approved
0.7257	Intermediate Similarity	NPD1358	Approved
0.725	Intermediate Similarity	NPD9268	Approved
0.725	Intermediate Similarity	NPD1357	Approved
0.7207	Intermediate Similarity	NPD9500	Approved
0.72	Intermediate Similarity	NPD9621	Approved
0.72	Intermediate Similarity	NPD9619	Approved
0.72	Intermediate Similarity	NPD9620	Approved
0.7197	Intermediate Similarity	NPD7266	Discontinued
0.7196	Intermediate Similarity	NPD9296	Approved
0.719	Intermediate Similarity	NPD2932	Approved
0.719	Intermediate Similarity	NPD3019	Approved
0.7188	Intermediate Similarity	NPD259	Phase 1
0.7177	Intermediate Similarity	NPD5310	Approved
0.7177	Intermediate Similarity	NPD5311	Approved
0.7168	Intermediate Similarity	NPD1445	Approved
0.7168	Intermediate Similarity	NPD1444	Approved
0.7168	Intermediate Similarity	NPD3134	Approved
0.7167	Intermediate Similarity	NPD9545	Approved
0.7164	Intermediate Similarity	NPD8166	Discontinued
0.7143	Intermediate Similarity	NPD9610	Approved
0.7143	Intermediate Similarity	NPD9608	Approved
0.7132	Intermediate Similarity	NPD826	Approved
0.7132	Intermediate Similarity	NPD825	Approved
0.7083	Intermediate Similarity	NPD9087	Approved
0.7077	Intermediate Similarity	NPD555	Phase 2
0.7077	Intermediate Similarity	NPD274	Approved
0.7077	Intermediate Similarity	NPD275	Approved
0.7049	Intermediate Similarity	NPD4626	Approved
0.7043	Intermediate Similarity	NPD74	Approved
0.7043	Intermediate Similarity	NPD9266	Approved
0.7034	Intermediate Similarity	NPD5283	Phase 1
0.7031	Intermediate Similarity	NPD3027	Phase 3
0.7031	Intermediate Similarity	NPD9537	Phase 1
0.7031	Intermediate Similarity	NPD9536	Phase 1
0.7	Intermediate Similarity	NPD9493	Approved
0.6983	Remote Similarity	NPD1792	Phase 2
0.6983	Remote Similarity	NPD4750	Phase 3
0.6977	Remote Similarity	NPD598	Approved
0.6977	Remote Similarity	NPD601	Approved
0.6977	Remote Similarity	NPD3145	Approved
0.6977	Remote Similarity	NPD597	Approved
0.6977	Remote Similarity	NPD3144	Approved
0.697	Remote Similarity	NPD9088	Approved
0.6967	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD9264	Approved
0.6957	Remote Similarity	NPD9263	Approved
0.6957	Remote Similarity	NPD9267	Approved
0.6953	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6935	Remote Similarity	NPD3092	Approved
0.6935	Remote Similarity	NPD1201	Approved
0.6923	Remote Similarity	NPD1136	Approved
0.6923	Remote Similarity	NPD1132	Approved
0.6923	Remote Similarity	NPD2674	Phase 3
0.6923	Remote Similarity	NPD1130	Approved
0.6917	Remote Similarity	NPD255	Approved
0.6917	Remote Similarity	NPD256	Approved
0.6897	Remote Similarity	NPD2684	Approved
0.6891	Remote Similarity	NPD2228	Approved
0.6891	Remote Similarity	NPD2234	Approved
0.6891	Remote Similarity	NPD2229	Approved
0.6891	Remote Similarity	NPD1241	Discontinued
0.6885	Remote Similarity	NPD3091	Approved
0.6875	Remote Similarity	NPD3028	Approved
0.6875	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.687	Remote Similarity	NPD1558	Phase 1
0.6861	Remote Similarity	NPD6190	Approved
0.685	Remote Similarity	NPD1470	Approved
0.6847	Remote Similarity	NPD9273	Approved
0.6846	Remote Similarity	NPD2028	Clinical (unspecified phase)
0.6838	Remote Similarity	NPD9380	Clinical (unspecified phase)
0.6833	Remote Similarity	NPD9614	Approved
0.6833	Remote Similarity	NPD9618	Approved
0.6818	Remote Similarity	NPD447	Suspended
0.681	Remote Similarity	NPD290	Approved
0.681	Remote Similarity	NPD2342	Discontinued
0.6807	Remote Similarity	NPD7635	Approved
0.68	Remote Similarity	NPD422	Phase 1
0.6777	Remote Similarity	NPD6671	Approved
0.6774	Remote Similarity	NPD4059	Approved
0.6763	Remote Similarity	NPD1511	Approved
0.6742	Remote Similarity	NPD1613	Approved
0.6742	Remote Similarity	NPD3061	Approved
0.6742	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6742	Remote Similarity	NPD3059	Approved
0.6742	Remote Similarity	NPD3062	Approved
0.6742	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6742	Remote Similarity	NPD3620	Phase 2
0.6741	Remote Similarity	NPD9570	Approved
0.6738	Remote Similarity	NPD711	Discontinued
0.6724	Remote Similarity	NPD968	Approved
0.6721	Remote Similarity	NPD9568	Approved
0.672	Remote Similarity	NPD3496	Discontinued
0.6719	Remote Similarity	NPD1164	Approved
0.6719	Remote Similarity	NPD3094	Phase 2
0.67	Remote Similarity	NPD9294	Approved
0.6699	Remote Similarity	NPD9089	Approved
0.6694	Remote Similarity	NPD1791	Approved
0.6694	Remote Similarity	NPD4093	Discontinued
0.6694	Remote Similarity	NPD5691	Approved
0.6694	Remote Similarity	NPD1793	Approved
0.6693	Remote Similarity	NPD1755	Approved
0.6667	Remote Similarity	NPD9616	Approved
0.6667	Remote Similarity	NPD9613	Approved
0.6667	Remote Similarity	NPD9258	Approved
0.6667	Remote Similarity	NPD9256	Approved
0.6667	Remote Similarity	NPD9615	Approved
0.6667	Remote Similarity	NPD1512	Approved
0.6667	Remote Similarity	NPD7843	Approved
0.6667	Remote Similarity	NPD9716	Approved
0.6643	Remote Similarity	NPD3455	Phase 2
0.6643	Remote Similarity	NPD824	Approved
0.6642	Remote Similarity	NPD817	Approved
0.6642	Remote Similarity	NPD823	Approved
0.6642	Remote Similarity	NPD5314	Approved
0.664	Remote Similarity	NPD2286	Discontinued
0.664	Remote Similarity	NPD1751	Approved
0.6639	Remote Similarity	NPD7157	Approved
0.6638	Remote Similarity	NPD9697	Approved
0.6617	Remote Similarity	NPD4060	Phase 1
0.6615	Remote Similarity	NPD5736	Approved
0.6613	Remote Similarity	NPD316	Approved
0.6609	Remote Similarity	NPD9261	Approved
0.6602	Remote Similarity	NPD9093	Approved
0.6587	Remote Similarity	NPD3026	Approved
0.6587	Remote Similarity	NPD3023	Approved
0.6583	Remote Similarity	NPD6124	Clinical (unspecified phase)
0.6574	Remote Similarity	NPD9295	Approved
0.6573	Remote Similarity	NPD1653	Approved
0.6562	Remote Similarity	NPD2983	Phase 2
0.6562	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD2982	Phase 2
0.656	Remote Similarity	NPD3025	Approved
0.656	Remote Similarity	NPD1651	Approved
0.656	Remote Similarity	NPD3024	Approved
0.6557	Remote Similarity	NPD475	Phase 2
0.6557	Remote Similarity	NPD9281	Approved
0.6552	Remote Similarity	NPD9244	Approved
0.6552	Remote Similarity	NPD1237	Approved
0.6549	Remote Similarity	NPD9495	Approved
0.6544	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6532	Remote Similarity	NPD317	Approved
0.6532	Remote Similarity	NPD318	Approved
0.6532	Remote Similarity	NPD856	Approved
0.6532	Remote Similarity	NPD16	Approved
0.6529	Remote Similarity	NPD821	Approved
0.6525	Remote Similarity	NPD4357	Discontinued
0.6522	Remote Similarity	NPD291	Approved
0.6515	Remote Similarity	NPD7095	Approved
0.6512	Remote Similarity	NPD1283	Approved
0.6508	Remote Similarity	NPD1778	Approved
0.6508	Remote Similarity	NPD3095	Discontinued
0.6507	Remote Similarity	NPD1934	Approved
0.6496	Remote Similarity	NPD2935	Discontinued
0.6496	Remote Similarity	NPD1632	Clinical (unspecified phase)
0.6493	Remote Similarity	NPD1240	Approved
0.6486	Remote Similarity	NPD3882	Suspended
0.6484	Remote Similarity	NPD9717	Approved
0.6484	Remote Similarity	NPD2981	Phase 2
0.648	Remote Similarity	NPD2226	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