NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	150.07
Volume:	162.698
LogP:	1.738
LogD:	1.597
LogS:	-1.904
# Rotatable Bonds:	2
TPSA:	26.3
# H-Bond Aceptor:	2
# H-Bond Donor:	0
# Rings:	1
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.602
Synthetic Accessibility Score:	1.206
Fsp3:	0.222
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:	-4.437
MDCK Permeability:	2.5896206352626905e-05
Pgp-inhibitor:	0.003
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.822

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.655
Plasma Protein Binding (PPB):	78.54509735107422%
Volume Distribution (VD):	0.683
Pgp-substrate:	19.052814483642578%

ADMET: Metabolism

CYP1A2-inhibitor:	0.976
CYP1A2-substrate:	0.956
CYP2C19-inhibitor:	0.887
CYP2C19-substrate:	0.509
CYP2C9-inhibitor:	0.242
CYP2C9-substrate:	0.903
CYP2D6-inhibitor:	0.165
CYP2D6-substrate:	0.88
CYP3A4-inhibitor:	0.086
CYP3A4-substrate:	0.41

ADMET: Excretion

Clearance (CL):	7.911
Half-life (T1/2):	0.792

ADMET: Toxicity

hERG Blockers:	0.118
Human Hepatotoxicity (H-HT):	0.05
Drug-inuced Liver Injury (DILI):	0.695
AMES Toxicity:	0.065
Rat Oral Acute Toxicity:	0.097
Maximum Recommended Daily Dose:	0.024
Skin Sensitization:	0.39
Carcinogencity:	0.75
Eye Corrosion:	0.709
Eye Irritation:	0.993
Respiratory Toxicity:	0.067

Download Data

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

Natural Product: NPC183648

Natural Product ID:	NPC183648
*Common Name:**	P-Methoxy-Acetophenone
IUPAC Name:	1-(4-methoxyphenyl)ethanone
Synonyms:	1-(4-Methoxyphenyl)Ethanone
Standard InCHIKey:	NTPLXRHDUXRPNE-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C9H10O2/c1-7(10)8-3-5-9(11-2)6-4-8/h3-6H,1-2H3
SMILES:	COc1ccc(cc1)C(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL401912
PubChem CID:	7476
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
NPO28295	Foeniculum vulgare	Species	Apiaceae	Eukaryota	n.a.	leaf	n.a.	DOI[10.1016/S0031-9422(00)94055-X]
NPO28295	Foeniculum vulgare	Species	Apiaceae	Eukaryota	n.a.	flower	n.a.	DOI[10.3390/70200245]
NPO11391	Polygonum cuspidatum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11076555]
NPO11391	Polygonum cuspidatum	Species	Polygonaceae	Eukaryota	Roots	n.a.	n.a.	PMID[11459643]
NPO32889	baccharis sp.	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11929285]
NPO11391	Polygonum cuspidatum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1517743]
NPO22273	Angelica pubescens	Species	Apiaceae	Eukaryota	n.a.	root	n.a.	PMID[17238120]
NPO22273	Angelica pubescens	Species	Apiaceae	Eukaryota	n.a.	root	n.a.	PMID[18405608]
NPO22273	Angelica pubescens	Species	Apiaceae	Eukaryota	n.a.	root	n.a.	PMID[18661821]
NPO22273	Angelica pubescens	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21417376]
NPO22273	Angelica pubescens	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21627108]
NPO28295	Foeniculum vulgare	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24617303]
NPO22273	Angelica pubescens	Species	Apiaceae	Eukaryota	n.a.	root	n.a.	PMID[7700984]
NPO11391	Polygonum cuspidatum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8277318]
NPO22273	Angelica pubescens	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[Article]
NPO17752	Mentha X piperita	Strain	Lamiaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO17752	Mentha X piperita	Strain	Lamiaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO17752	Mentha X piperita	Strain	Lamiaceae	Eukaryota	Shoot	n.a.	n.a.	Database[FooDB]
NPO17752	Mentha X piperita	Strain	Lamiaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO17752	Mentha X piperita	Strain	Lamiaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO22273	Angelica pubescens	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11391	Polygonum cuspidatum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28295	Foeniculum vulgare	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17752	Mentha X piperita	Strain	Lamiaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO11391	Polygonum cuspidatum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28295	Foeniculum vulgare	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22273	Angelica pubescens	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17752	Mentha X piperita	Strain	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22273	Angelica pubescens	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO11391	Polygonum cuspidatum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO28295	Foeniculum vulgare	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO11391	Polygonum cuspidatum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO22273	Angelica pubescens	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO28295	Foeniculum vulgare	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO11391	Polygonum cuspidatum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17752	Mentha X piperita	Strain	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22273	Angelica pubescens	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28295	Foeniculum vulgare	Species	Apiaceae	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
NPO17752	NPC183648	Other	Leaf	0.0055	0.001	0.01	mg/100g	Database [DUKE]

☑ 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
GI50	4
IC50	15
Others	4
Potency	6

Activity Type	# Activity
Individual Protein	5
Organism	18
Others	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT590	Individual Protein	3-alpha-hydroxysteroid dehydrogenase	Rattus norvegicus	Km	=	5590000.0	nM	PMID[545811]
NPT590	Individual Protein	3-alpha-hydroxysteroid dehydrogenase	Rattus norvegicus	Ratio	=	0.97	uL/min	PMID[545811]
NPT590	Individual Protein	3-alpha-hydroxysteroid dehydrogenase	Rattus norvegicus	Vmax	=	0.005	micromol/min	PMID[545811]
NPT43	Individual Protein	Tyrosinase	Agaricus bisporus	IC50	=	2000000.0	nM	PMID[545812]
NPT43	Individual Protein	Tyrosinase	Agaricus bisporus	Inhibition	=	47.2	%	PMID[545812]
NPT597	Organism	Spinacia oleracea	Spinacia oleracea	IC50	=	65700.0	nM	PMID[545813]
NPT355	Organism	Phaseolus vulgaris	Phaseolus vulgaris	IC50	=	151800.0	nM	PMID[545813]
NPT594	Organism	Trifolium pratense	Trifolium pratense	IC50	=	57600.0	nM	PMID[545813]
NPT595	Organism	Physalis ixocarpa	Physalis ixocarpa	IC50	=	54600.0	nM	PMID[545813]
NPT364	Organism	Lactuca sativa	Lactuca sativa	IC50	=	55900.0	nM	PMID[545813]
NPT596	Organism	Lolium multiflorum	Lolium multiflorum	IC50	=	40000.0	nM	PMID[545813]
NPT594	Organism	Trifolium pratense	Trifolium pratense	IC50	=	126200.0	nM	PMID[545813]
NPT594	Organism	Trifolium pratense	Trifolium pratense	IC50	=	120000.0	nM	PMID[545813]
NPT595	Organism	Physalis ixocarpa	Physalis ixocarpa	IC50	=	20500.0	nM	PMID[545813]
NPT595	Organism	Physalis ixocarpa	Physalis ixocarpa	IC50	=	20100.0	nM	PMID[545813]
NPT364	Organism	Lactuca sativa	Lactuca sativa	IC50	=	44300.0	nM	PMID[545813]
NPT364	Organism	Lactuca sativa	Lactuca sativa	IC50	=	49500.0	nM	PMID[545813]
NPT596	Organism	Lolium multiflorum	Lolium multiflorum	IC50	=	18900.0	nM	PMID[545813]
NPT596	Organism	Lolium multiflorum	Lolium multiflorum	IC50	=	17900.0	nM	PMID[545813]
NPT596	Organism	Lolium multiflorum	Lolium multiflorum	GI50	=	18100.0	nM	PMID[545813]
NPT364	Organism	Lactuca sativa	Lactuca sativa	GI50	=	51200.0	nM	PMID[545813]
NPT595	Organism	Physalis ixocarpa	Physalis ixocarpa	GI50	=	23500.0	nM	PMID[545813]
NPT594	Organism	Trifolium pratense	Trifolium pratense	GI50	=	125900.0	nM	PMID[545813]
NPT2	Others	Unspecified		Potency	n.a.	22548.5	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	44600.8	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	28141.2	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	566.4	nM	PubChem BioAssay data set

☑ 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 NPC183648 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	369
0.1-0.2	2488
0.2-0.3	6032
0.3-0.4	11368
0.4-0.5	5065
0.5-0.6	6989
0.6-0.7	8068
0.7-0.8	2137
0.8-0.85	151
0.85-0.9	21
0.9-0.95	6
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9903	High Similarity	NPC23332
0.9524	High Similarity	NPC57879
0.9358	High Similarity	NPC469954
0.9266	High Similarity	NPC470860
0.9259	High Similarity	NPC252004
0.9223	High Similarity	NPC38209
0.9174	High Similarity	NPC220540
0.9126	High Similarity	NPC298224
0.9027	High Similarity	NPC225245
0.8922	High Similarity	NPC175298
0.8868	High Similarity	NPC1065
0.885	High Similarity	NPC61779
0.8807	High Similarity	NPC54626
0.8793	High Similarity	NPC474691
0.8793	High Similarity	NPC11799
0.8793	High Similarity	NPC141252
0.8696	High Similarity	NPC295317
0.8692	High Similarity	NPC6984
0.8649	High Similarity	NPC279916
0.8649	High Similarity	NPC53953
0.8644	High Similarity	NPC65041
0.8644	High Similarity	NPC470858
0.8624	High Similarity	NPC234639
0.8611	High Similarity	NPC226699
0.8596	High Similarity	NPC171023
0.8584	High Similarity	NPC19290
0.8571	High Similarity	NPC177925
0.8571	High Similarity	NPC13755
0.8559	High Similarity	NPC30216
0.8547	High Similarity	NPC69403
0.8547	High Similarity	NPC291189
0.85	High Similarity	NPC293387
0.85	High Similarity	NPC32163
0.85	High Similarity	NPC16651
0.85	High Similarity	NPC286683
0.8496	Intermediate Similarity	NPC188907
0.8482	Intermediate Similarity	NPC11824
0.8455	Intermediate Similarity	NPC95172
0.8455	Intermediate Similarity	NPC259554
0.8435	Intermediate Similarity	NPC166591
0.843	Intermediate Similarity	NPC80694
0.843	Intermediate Similarity	NPC186098
0.8421	Intermediate Similarity	NPC131192
0.8417	Intermediate Similarity	NPC474737
0.8417	Intermediate Similarity	NPC237868
0.8411	Intermediate Similarity	NPC179686
0.8403	Intermediate Similarity	NPC221798
0.8403	Intermediate Similarity	NPC255073
0.8364	Intermediate Similarity	NPC17525
0.8362	Intermediate Similarity	NPC201284
0.8361	Intermediate Similarity	NPC939
0.8361	Intermediate Similarity	NPC211120
0.8361	Intermediate Similarity	NPC170546
0.8361	Intermediate Similarity	NPC66246
0.8348	Intermediate Similarity	NPC45104
0.8348	Intermediate Similarity	NPC217423
0.8348	Intermediate Similarity	NPC240664
0.8333	Intermediate Similarity	NPC473626
0.8333	Intermediate Similarity	NPC165556
0.8333	Intermediate Similarity	NPC2518
0.8333	Intermediate Similarity	NPC2771
0.8333	Intermediate Similarity	NPC71853
0.8319	Intermediate Similarity	NPC109241
0.8304	Intermediate Similarity	NPC212718
0.8304	Intermediate Similarity	NPC114682
0.8293	Intermediate Similarity	NPC282230
0.8293	Intermediate Similarity	NPC66905
0.8293	Intermediate Similarity	NPC183348
0.8293	Intermediate Similarity	NPC247779
0.8291	Intermediate Similarity	NPC470092
0.8279	Intermediate Similarity	NPC2596
0.8276	Intermediate Similarity	NPC27633
0.8276	Intermediate Similarity	NPC94298
0.8276	Intermediate Similarity	NPC32298
0.8276	Intermediate Similarity	NPC293424
0.8264	Intermediate Similarity	NPC154275
0.8264	Intermediate Similarity	NPC475236
0.8264	Intermediate Similarity	NPC474264
0.8261	Intermediate Similarity	NPC316062
0.8257	Intermediate Similarity	NPC128730
0.8252	Intermediate Similarity	NPC321956
0.8235	Intermediate Similarity	NPC8002
0.8235	Intermediate Similarity	NPC99886
0.8235	Intermediate Similarity	NPC177844
0.8235	Intermediate Similarity	NPC259134
0.823	Intermediate Similarity	NPC231717
0.8226	Intermediate Similarity	NPC196979
0.8226	Intermediate Similarity	NPC470976
0.8226	Intermediate Similarity	NPC15083
0.8226	Intermediate Similarity	NPC470977
0.8226	Intermediate Similarity	NPC125153
0.8214	Intermediate Similarity	NPC116842
0.8205	Intermediate Similarity	NPC54243
0.8205	Intermediate Similarity	NPC35744
0.8197	Intermediate Similarity	NPC428300
0.8197	Intermediate Similarity	NPC475496
0.8197	Intermediate Similarity	NPC37512
0.8197	Intermediate Similarity	NPC128428
0.8197	Intermediate Similarity	NPC49852
0.8197	Intermediate Similarity	NPC203719
0.8197	Intermediate Similarity	NPC117237
0.8197	Intermediate Similarity	NPC121104
0.8197	Intermediate Similarity	NPC305518
0.8182	Intermediate Similarity	NPC176971
0.8182	Intermediate Similarity	NPC326447
0.8174	Intermediate Similarity	NPC322358
0.8167	Intermediate Similarity	NPC182646
0.8165	Intermediate Similarity	NPC109637
0.816	Intermediate Similarity	NPC308037
0.816	Intermediate Similarity	NPC470859
0.816	Intermediate Similarity	NPC183103
0.816	Intermediate Similarity	NPC153453
0.816	Intermediate Similarity	NPC112192
0.816	Intermediate Similarity	NPC313618
0.816	Intermediate Similarity	NPC262359
0.816	Intermediate Similarity	NPC128348
0.816	Intermediate Similarity	NPC189106
0.816	Intermediate Similarity	NPC50763
0.816	Intermediate Similarity	NPC309717
0.816	Intermediate Similarity	NPC66384
0.816	Intermediate Similarity	NPC164236
0.816	Intermediate Similarity	NPC64359
0.816	Intermediate Similarity	NPC284424
0.8158	Intermediate Similarity	NPC242136
0.8151	Intermediate Similarity	NPC314329
0.8148	Intermediate Similarity	NPC84325
0.8145	Intermediate Similarity	NPC245395
0.8142	Intermediate Similarity	NPC268388
0.8136	Intermediate Similarity	NPC230951
0.813	Intermediate Similarity	NPC50583
0.813	Intermediate Similarity	NPC473907
0.813	Intermediate Similarity	NPC125887
0.812	Intermediate Similarity	NPC152159
0.812	Intermediate Similarity	NPC206007
0.8108	Intermediate Similarity	NPC151530
0.8108	Intermediate Similarity	NPC157473
0.8099	Intermediate Similarity	NPC56332
0.8095	Intermediate Similarity	NPC182428
0.8095	Intermediate Similarity	NPC212631
0.8095	Intermediate Similarity	NPC205468
0.8095	Intermediate Similarity	NPC129132
0.8095	Intermediate Similarity	NPC229646
0.8095	Intermediate Similarity	NPC87231
0.8095	Intermediate Similarity	NPC257756
0.8091	Intermediate Similarity	NPC219913
0.8087	Intermediate Similarity	NPC114144
0.8083	Intermediate Similarity	NPC114298
0.8083	Intermediate Similarity	NPC67300
0.808	Intermediate Similarity	NPC239134
0.808	Intermediate Similarity	NPC279596
0.808	Intermediate Similarity	NPC164295
0.8065	Intermediate Similarity	NPC78662
0.8065	Intermediate Similarity	NPC8005
0.8065	Intermediate Similarity	NPC60558
0.8065	Intermediate Similarity	NPC212379
0.8065	Intermediate Similarity	NPC473894
0.8065	Intermediate Similarity	NPC69235
0.8053	Intermediate Similarity	NPC473809
0.8033	Intermediate Similarity	NPC120066
0.8033	Intermediate Similarity	NPC224657
0.8031	Intermediate Similarity	NPC263670
0.8031	Intermediate Similarity	NPC188646
0.8031	Intermediate Similarity	NPC312318
0.8031	Intermediate Similarity	NPC175098
0.8031	Intermediate Similarity	NPC472365
0.8031	Intermediate Similarity	NPC292998
0.8031	Intermediate Similarity	NPC56031
0.8031	Intermediate Similarity	NPC223354
0.8031	Intermediate Similarity	NPC192304
0.8031	Intermediate Similarity	NPC337373
0.8031	Intermediate Similarity	NPC139813
0.8031	Intermediate Similarity	NPC27643
0.8031	Intermediate Similarity	NPC242294
0.8017	Intermediate Similarity	NPC257976
0.8017	Intermediate Similarity	NPC242372
0.8017	Intermediate Similarity	NPC164778
0.8017	Intermediate Similarity	NPC472888
0.8017	Intermediate Similarity	NPC473942
0.8017	Intermediate Similarity	NPC4181
0.8016	Intermediate Similarity	NPC278556
0.8	Intermediate Similarity	NPC307732
0.8	Intermediate Similarity	NPC42292
0.8	Intermediate Similarity	NPC285776
0.8	Intermediate Similarity	NPC298268
0.8	Intermediate Similarity	NPC185497
0.8	Intermediate Similarity	NPC109778
0.7984	Intermediate Similarity	NPC2401
0.7984	Intermediate Similarity	NPC475017
0.7984	Intermediate Similarity	NPC304747
0.7983	Intermediate Similarity	NPC246214
0.7982	Intermediate Similarity	NPC307425
0.7982	Intermediate Similarity	NPC233238
0.7969	Intermediate Similarity	NPC286336
0.7969	Intermediate Similarity	NPC139519
0.7969	Intermediate Similarity	NPC89504
0.7969	Intermediate Similarity	NPC95485
0.7969	Intermediate Similarity	NPC164136
0.7969	Intermediate Similarity	NPC125269
0.7969	Intermediate Similarity	NPC88065
0.7963	Intermediate Similarity	NPC280869

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 NPC183648 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	374
0.1-0.2	1064
0.2-0.3	1389
0.3-0.4	2671
0.4-0.5	1948
0.5-0.6	1163
0.6-0.7	443
0.7-0.8	89
0.8-0.85	7
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8991	High Similarity	NPD1241	Discontinued
0.887	High Similarity	NPD3972	Approved
0.8403	Intermediate Similarity	NPD1876	Approved
0.8276	Intermediate Similarity	NPD9545	Approved
0.8197	Intermediate Similarity	NPD9494	Approved
0.8182	Intermediate Similarity	NPD3134	Approved
0.816	Intermediate Similarity	NPD1240	Approved
0.816	Intermediate Similarity	NPD3142	Approved
0.816	Intermediate Similarity	NPD3140	Approved
0.8151	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.8108	Intermediate Similarity	NPD1358	Approved
0.8031	Intermediate Similarity	NPD1607	Approved
0.7899	Intermediate Similarity	NPD1651	Approved
0.7881	Intermediate Similarity	NPD5536	Phase 2
0.7846	Intermediate Similarity	NPD2796	Approved
0.7826	Intermediate Similarity	NPD1609	Clinical (unspecified phase)
0.7823	Intermediate Similarity	NPD2798	Approved
0.7797	Intermediate Similarity	NPD9493	Approved
0.7788	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7787	Intermediate Similarity	NPD9717	Approved
0.7769	Intermediate Similarity	NPD1510	Phase 2
0.7705	Intermediate Similarity	NPD1281	Approved
0.7698	Intermediate Similarity	NPD6832	Phase 2
0.7692	Intermediate Similarity	NPD743	Approved
0.7686	Intermediate Similarity	NPD17	Approved
0.768	Intermediate Similarity	NPD1019	Discontinued
0.7669	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7652	Intermediate Similarity	NPD2353	Approved
0.7652	Intermediate Similarity	NPD2344	Approved
0.7652	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.7594	Intermediate Similarity	NPD1549	Phase 2
0.7556	Intermediate Similarity	NPD3887	Approved
0.7522	Intermediate Similarity	NPD164	Approved
0.7521	Intermediate Similarity	NPD1894	Discontinued
0.752	Intermediate Similarity	NPD1283	Approved
0.7519	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7519	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1608	Approved
0.75	Intermediate Similarity	NPD2799	Discontinued
0.7481	Intermediate Similarity	NPD4628	Phase 3
0.7477	Intermediate Similarity	NPD1238	Approved
0.746	Intermediate Similarity	NPD3267	Approved
0.746	Intermediate Similarity	NPD3266	Approved
0.746	Intermediate Similarity	NPD1203	Approved
0.7459	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7456	Intermediate Similarity	NPD9697	Approved
0.7445	Intermediate Similarity	NPD6799	Approved
0.7444	Intermediate Similarity	NPD2935	Discontinued
0.744	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7434	Intermediate Similarity	NPD9261	Approved
0.7426	Intermediate Similarity	NPD2309	Approved
0.7426	Intermediate Similarity	NPD2354	Approved
0.7414	Intermediate Similarity	NPD2684	Approved
0.7407	Intermediate Similarity	NPD2654	Approved
0.7407	Intermediate Similarity	NPD1243	Approved
0.7388	Intermediate Similarity	NPD1471	Phase 3
0.7368	Intermediate Similarity	NPD3748	Approved
0.736	Intermediate Similarity	NPD1481	Phase 2
0.735	Intermediate Similarity	NPD5451	Approved
0.7339	Intermediate Similarity	NPD3847	Discontinued
0.7333	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7328	Intermediate Similarity	NPD4307	Phase 2
0.7317	Intermediate Similarity	NPD5691	Approved
0.7311	Intermediate Similarity	NPD5535	Approved
0.7308	Intermediate Similarity	NPD2313	Discontinued
0.7308	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7288	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.7286	Intermediate Similarity	NPD5586	Clinical (unspecified phase)
0.7286	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.728	Intermediate Similarity	NPD1535	Discovery
0.7273	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD1933	Approved
0.7266	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7265	Intermediate Similarity	NPD2182	Approved
0.7258	Intermediate Similarity	NPD4626	Approved
0.7246	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD196	Phase 1
0.7234	Intermediate Similarity	NPD957	Approved
0.7227	Intermediate Similarity	NPD228	Approved
0.7226	Intermediate Similarity	NPD7003	Approved
0.7209	Intermediate Similarity	NPD454	Approved
0.7188	Intermediate Similarity	NPD2797	Approved
0.7183	Intermediate Similarity	NPD7458	Discontinued
0.7179	Intermediate Similarity	NPD9267	Approved
0.7179	Intermediate Similarity	NPD9264	Approved
0.7179	Intermediate Similarity	NPD9263	Approved
0.7176	Intermediate Similarity	NPD3268	Approved
0.7176	Intermediate Similarity	NPD411	Approved
0.717	Intermediate Similarity	NPD9259	Approved
0.717	Intermediate Similarity	NPD9257	Approved
0.7167	Intermediate Similarity	NPD821	Approved
0.7167	Intermediate Similarity	NPD7843	Approved
0.7163	Intermediate Similarity	NPD920	Approved
0.7143	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD447	Suspended
0.7143	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD230	Phase 1
0.7133	Intermediate Similarity	NPD6599	Discontinued
0.7132	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.712	Intermediate Similarity	NPD1778	Approved
0.7119	Intermediate Similarity	NPD9266	Approved
0.7119	Intermediate Similarity	NPD74	Approved
0.7111	Intermediate Similarity	NPD4308	Phase 3
0.7107	Intermediate Similarity	NPD5283	Phase 1
0.7101	Intermediate Similarity	NPD3750	Approved
0.7101	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7092	Intermediate Similarity	NPD2186	Approved
0.7083	Intermediate Similarity	NPD958	Approved
0.7083	Intermediate Similarity	NPD7411	Suspended
0.7073	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD1511	Approved
0.7069	Intermediate Similarity	NPD1237	Approved
0.7068	Intermediate Similarity	NPD2979	Phase 3
0.7049	Intermediate Similarity	NPD690	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD6798	Discontinued
0.7045	Intermediate Similarity	NPD1296	Phase 2
0.7045	Intermediate Similarity	NPD3764	Approved
0.7042	Intermediate Similarity	NPD1670	Discontinued
0.704	Intermediate Similarity	NPD5585	Approved
0.7034	Intermediate Similarity	NPD6279	Approved
0.7034	Intermediate Similarity	NPD290	Approved
0.7034	Intermediate Similarity	NPD7577	Discontinued
0.7034	Intermediate Similarity	NPD6280	Approved
0.7027	Intermediate Similarity	NPD1202	Approved
0.7014	Intermediate Similarity	NPD4380	Phase 2
0.7008	Intermediate Similarity	NPD422	Phase 1
0.7007	Intermediate Similarity	NPD2346	Discontinued
0.7	Intermediate Similarity	NPD7440	Discontinued
0.6992	Remote Similarity	NPD6233	Phase 2
0.6992	Remote Similarity	NPD4062	Phase 3
0.6992	Remote Similarity	NPD8032	Phase 2
0.6992	Remote Similarity	NPD7157	Approved
0.6986	Remote Similarity	NPD7819	Suspended
0.6986	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6984	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6972	Remote Similarity	NPD6273	Approved
0.6972	Remote Similarity	NPD1512	Approved
0.6966	Remote Similarity	NPD6386	Approved
0.6966	Remote Similarity	NPD6385	Approved
0.6963	Remote Similarity	NPD6651	Approved
0.695	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6949	Remote Similarity	NPD968	Approved
0.6944	Remote Similarity	NPD824	Approved
0.6939	Remote Similarity	NPD5977	Approved
0.6939	Remote Similarity	NPD5978	Approved
0.6934	Remote Similarity	NPD1551	Phase 2
0.6929	Remote Similarity	NPD3496	Discontinued
0.6918	Remote Similarity	NPD1934	Approved
0.6918	Remote Similarity	NPD6801	Discontinued
0.6916	Remote Similarity	NPD111	Approved
0.6909	Remote Similarity	NPD9256	Approved
0.6909	Remote Similarity	NPD9258	Approved
0.6901	Remote Similarity	NPD4661	Approved
0.6901	Remote Similarity	NPD4662	Approved
0.6897	Remote Similarity	NPD2592	Discontinued
0.6894	Remote Similarity	NPD2614	Approved
0.6892	Remote Similarity	NPD3882	Suspended
0.6889	Remote Similarity	NPD6355	Discontinued
0.6871	Remote Similarity	NPD2801	Approved
0.6871	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.687	Remote Similarity	NPD5647	Approved
0.6853	Remote Similarity	NPD5049	Phase 3
0.6846	Remote Similarity	NPD7075	Discontinued
0.6846	Remote Similarity	NPD3225	Approved
0.6824	Remote Similarity	NPD2296	Approved
0.6824	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD3817	Phase 2
0.6818	Remote Similarity	NPD9295	Approved
0.6815	Remote Similarity	NPD943	Approved
0.6814	Remote Similarity	NPD2934	Approved
0.6814	Remote Similarity	NPD2933	Approved
0.6812	Remote Similarity	NPD4476	Approved
0.6812	Remote Similarity	NPD2531	Phase 2
0.6812	Remote Similarity	NPD4477	Approved
0.6812	Remote Similarity	NPD2438	Suspended
0.6809	Remote Similarity	NPD3295	Clinical (unspecified phase)
0.6806	Remote Similarity	NPD3869	Phase 3
0.6806	Remote Similarity	NPD3873	Phase 3
0.6803	Remote Similarity	NPD1139	Approved
0.6803	Remote Similarity	NPD1137	Approved
0.68	Remote Similarity	NPD6862	Phase 2
0.68	Remote Similarity	NPD919	Approved
0.68	Remote Similarity	NPD3596	Phase 2
0.6794	Remote Similarity	NPD1164	Approved
0.6786	Remote Similarity	NPD2800	Approved
0.6783	Remote Similarity	NPD5401	Approved
0.6781	Remote Similarity	NPD1337	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD9281	Approved
0.6772	Remote Similarity	NPD9268	Approved
0.6769	Remote Similarity	NPD4359	Approved
0.6767	Remote Similarity	NPD1008	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD4618	Approved
0.6765	Remote Similarity	NPD4622	Approved
0.6755	Remote Similarity	NPD5494	Approved
0.6754	Remote Similarity	NPD2859	Approved
0.6754	Remote Similarity	NPD2860	Approved
0.6748	Remote Similarity	NPD1138	Approved
0.6744	Remote Similarity	NPD6287	Discontinued
0.6744	Remote Similarity	NPD1201	Approved
0.6735	Remote Similarity	NPD6873	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