NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	152.05
Volume:	154.193
LogP:	1.896
LogD:	1.397
LogS:	-1.966
# Rotatable Bonds:	1
TPSA:	57.53
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	1
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.596
Synthetic Accessibility Score:	2.057
Fsp3:	0.125
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:	-4.607
MDCK Permeability:	1.7311194824287668e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.326
30% Bioavailability (F30%):	0.149

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.187
Plasma Protein Binding (PPB):	87.57827758789062%
Volume Distribution (VD):	0.775
Pgp-substrate:	17.567638397216797%

ADMET: Metabolism

CYP1A2-inhibitor:	0.92
CYP1A2-substrate:	0.549
CYP2C19-inhibitor:	0.227
CYP2C19-substrate:	0.066
CYP2C9-inhibitor:	0.314
CYP2C9-substrate:	0.842
CYP2D6-inhibitor:	0.569
CYP2D6-substrate:	0.415
CYP3A4-inhibitor:	0.428
CYP3A4-substrate:	0.194

ADMET: Excretion

Clearance (CL):	10.327
Half-life (T1/2):	0.846

ADMET: Toxicity

hERG Blockers:	0.014
Human Hepatotoxicity (H-HT):	0.045
Drug-inuced Liver Injury (DILI):	0.599
AMES Toxicity:	0.579
Rat Oral Acute Toxicity:	0.566
Maximum Recommended Daily Dose:	0.03
Skin Sensitization:	0.84
Carcinogencity:	0.667
Eye Corrosion:	0.912
Eye Irritation:	0.992
Respiratory Toxicity:	0.878

Download Data

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

Natural Product: NPC118288

Natural Product ID:	NPC118288
*Common Name:**	1-(2,6-Dihydroxyphenyl)Ethanone
IUPAC Name:	1-(2,6-dihydroxyphenyl)ethanone
Synonyms:	2',6'-Dihydroxyacetophenone; 2,6-Dihydroxy Acetophenone; 2,6-Dihydroxyacetophenone
Standard InCHIKey:	YPTJKHVBDCRKNF-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C8H8O3/c1-5(9)8-6(10)3-2-4-7(8)11/h2-4,10-11H,1H3
SMILES:	CC(=O)c1c(O)cccc1O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL454739
PubChem CID:	69687
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
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota	seeds	n.a.	n.a.	PMID[17998162]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1955885]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota	n.a.	fruit	n.a.	PMID[20879744]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27419473]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota	Aril	n.a.	n.a.	Database[FooDB]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota	Bark	n.a.	n.a.	Database[FooDB]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota	Leaf Essent. Oil	n.a.	n.a.	Database[FooDB]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[Title]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO5241	Myristica fragrans	Species	Myristicaceae	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	3
Ki	3
MIC	6
Others	6
Potency	3

Activity Type	# Activity
Individual Protein	5
Organism	8
Others	8

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2875	Individual Protein	Solute carrier family 28 member 3	Homo sapiens	Ki	>	100000.0	nM	PMID[499808]
NPT46	Individual Protein	Thyroid hormone receptor beta-1	Homo sapiens	Potency	=	446683.6	nM	PMID[499809]
NPT53	Individual Protein	4'-phosphopantetheinyl transferase ffp	Bacillus subtilis	Potency	=	25118.9	nM	PMID[499809]
NPT531	Individual Protein	Nuclear receptor ROR-gamma	Mus musculus	Potency	=	15848.9	nM	PMID[499809]
NPT43	Individual Protein	Tyrosinase	Agaricus bisporus	IC50	>	300000.0	nM	PMID[499811]
NPT2	Others	Unspecified		Vmax	=	17.97	nmol/min	PMID[499806]
NPT2	Others	Unspecified		Km	=	4250000.0	nM	PMID[499806]
NPT2	Others	Unspecified		Vmax	=	18.19	nmol/min	PMID[499806]
NPT2	Others	Unspecified		Km	=	7780000.0	nM	PMID[499806]
NPT2	Others	Unspecified		Ki	=	30.11	nM	PMID[499806]
NPT2	Others	Unspecified		Ki	=	31.2	nM	PMID[499806]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	<	32.0	ug.mL-1	PMID[499807]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	<	32.0	ug.mL-1	PMID[499807]
NPT3730	Organism	Enterococcus durans	Enterococcus durans	MIC	<	32.0	ug.mL-1	PMID[499807]
NPT20	Organism	Candida albicans	Candida albicans	MIC	<	32.0	ug.mL-1	PMID[499807]
NPT2	Others	Unspecified		IC50	=	210000.0	nM	PMID[499810]
NPT2	Others	Unspecified		IC50	=	140000.0	nM	PMID[499810]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Activity	=	190.0	%	PMID[499810]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Activity	=	164.0	%	PMID[499810]

☑ 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 NPC118288 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	314
0.1-0.2	1955
0.2-0.3	4909
0.3-0.4	13125
0.4-0.5	5540
0.5-0.6	6457
0.6-0.7	7016
0.7-0.8	2995
0.8-0.85	277
0.85-0.9	77
0.9-0.95	27
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC276111
0.9725	High Similarity	NPC121259
0.955	High Similarity	NPC161617
0.9459	High Similarity	NPC209486
0.9459	High Similarity	NPC40649
0.9375	High Similarity	NPC188814
0.9375	High Similarity	NPC195262
0.9292	High Similarity	NPC294037
0.9252	High Similarity	NPC224584
0.9217	High Similarity	NPC309765
0.9211	High Similarity	NPC146642
0.9211	High Similarity	NPC149246
0.9211	High Similarity	NPC297186
0.9182	High Similarity	NPC223004
0.913	High Similarity	NPC196976
0.913	High Similarity	NPC143427
0.913	High Similarity	NPC115159
0.913	High Similarity	NPC45438
0.913	High Similarity	NPC73532
0.913	High Similarity	NPC242895
0.913	High Similarity	NPC156139
0.913	High Similarity	NPC215392
0.913	High Similarity	NPC303737
0.913	High Similarity	NPC224273
0.913	High Similarity	NPC19174
0.913	High Similarity	NPC267552
0.9052	High Similarity	NPC133909
0.9052	High Similarity	NPC91105
0.9052	High Similarity	NPC32032
0.8974	High Similarity	NPC65761
0.8974	High Similarity	NPC472029
0.8966	High Similarity	NPC226275
0.8957	High Similarity	NPC294964
0.8908	High Similarity	NPC62952
0.8908	High Similarity	NPC267846
0.8898	High Similarity	NPC13238
0.887	High Similarity	NPC158222
0.8833	High Similarity	NPC116513
0.8833	High Similarity	NPC100067
0.8833	High Similarity	NPC98254
0.8833	High Similarity	NPC105157
0.8833	High Similarity	NPC266689
0.8833	High Similarity	NPC30501
0.8833	High Similarity	NPC23126
0.8833	High Similarity	NPC72158
0.8833	High Similarity	NPC162612
0.8833	High Similarity	NPC103356
0.8833	High Similarity	NPC190043
0.8833	High Similarity	NPC169250
0.8824	High Similarity	NPC477454
0.8824	High Similarity	NPC475733
0.8793	High Similarity	NPC159525
0.8783	High Similarity	NPC283844
0.8783	High Similarity	NPC241089
0.876	High Similarity	NPC21305
0.876	High Similarity	NPC186098
0.876	High Similarity	NPC80694
0.876	High Similarity	NPC473017
0.876	High Similarity	NPC221777
0.875	High Similarity	NPC8745
0.875	High Similarity	NPC473691
0.8727	High Similarity	NPC100551
0.8696	High Similarity	NPC230349
0.8696	High Similarity	NPC125252
0.8689	High Similarity	NPC109123
0.8689	High Similarity	NPC92624
0.8689	High Similarity	NPC474998
0.8689	High Similarity	NPC187907
0.8684	High Similarity	NPC240163
0.8684	High Similarity	NPC161304
0.8678	High Similarity	NPC305518
0.8678	High Similarity	NPC128428
0.8673	High Similarity	NPC211421
0.8667	High Similarity	NPC201728
0.8667	High Similarity	NPC262671
0.8667	High Similarity	NPC10926
0.8636	High Similarity	NPC141523
0.8618	High Similarity	NPC259942
0.8609	High Similarity	NPC477453
0.8609	High Similarity	NPC128825
0.8607	High Similarity	NPC41263
0.8595	High Similarity	NPC95309
0.8583	High Similarity	NPC6888
0.8548	High Similarity	NPC475042
0.8548	High Similarity	NPC198249
0.8537	High Similarity	NPC120488
0.8537	High Similarity	NPC197425
0.8537	High Similarity	NPC476119
0.8537	High Similarity	NPC102829
0.8537	High Similarity	NPC212379
0.8537	High Similarity	NPC69235
0.8534	High Similarity	NPC269414
0.848	Intermediate Similarity	NPC262359
0.848	Intermediate Similarity	NPC175738
0.848	Intermediate Similarity	NPC64359
0.848	Intermediate Similarity	NPC475008
0.848	Intermediate Similarity	NPC308037
0.848	Intermediate Similarity	NPC186097
0.848	Intermediate Similarity	NPC475009
0.848	Intermediate Similarity	NPC313618
0.8468	Intermediate Similarity	NPC303264
0.8468	Intermediate Similarity	NPC17840
0.8468	Intermediate Similarity	NPC233056
0.8468	Intermediate Similarity	NPC226699
0.8468	Intermediate Similarity	NPC39753
0.8468	Intermediate Similarity	NPC26697
0.8468	Intermediate Similarity	NPC34715
0.8468	Intermediate Similarity	NPC244441
0.8468	Intermediate Similarity	NPC247477
0.8468	Intermediate Similarity	NPC115998
0.8462	Intermediate Similarity	NPC94637
0.8462	Intermediate Similarity	NPC41567
0.8413	Intermediate Similarity	NPC40524
0.8413	Intermediate Similarity	NPC205468
0.8413	Intermediate Similarity	NPC87231
0.8413	Intermediate Similarity	NPC129132
0.8413	Intermediate Similarity	NPC257756
0.8413	Intermediate Similarity	NPC212631
0.8413	Intermediate Similarity	NPC213485
0.8413	Intermediate Similarity	NPC139074
0.8403	Intermediate Similarity	NPC178395
0.8403	Intermediate Similarity	NPC179092
0.8403	Intermediate Similarity	NPC301987
0.8403	Intermediate Similarity	NPC292665
0.8403	Intermediate Similarity	NPC35856
0.8403	Intermediate Similarity	NPC272454
0.8403	Intermediate Similarity	NPC115188
0.8403	Intermediate Similarity	NPC244994
0.8403	Intermediate Similarity	NPC222876
0.8403	Intermediate Similarity	NPC26433
0.8403	Intermediate Similarity	NPC248363
0.8403	Intermediate Similarity	NPC159760
0.84	Intermediate Similarity	NPC5515
0.84	Intermediate Similarity	NPC137264
0.84	Intermediate Similarity	NPC34070
0.84	Intermediate Similarity	NPC469526
0.84	Intermediate Similarity	NPC270369
0.84	Intermediate Similarity	NPC275504
0.839	Intermediate Similarity	NPC233165
0.839	Intermediate Similarity	NPC328459
0.839	Intermediate Similarity	NPC90522
0.839	Intermediate Similarity	NPC184579
0.8387	Intermediate Similarity	NPC230818
0.8387	Intermediate Similarity	NPC78662
0.8387	Intermediate Similarity	NPC60558
0.8387	Intermediate Similarity	NPC8005
0.8378	Intermediate Similarity	NPC6984
0.8348	Intermediate Similarity	NPC242136
0.8348	Intermediate Similarity	NPC162113
0.8348	Intermediate Similarity	NPC62546
0.8346	Intermediate Similarity	NPC175098
0.8346	Intermediate Similarity	NPC294593
0.8346	Intermediate Similarity	NPC204960
0.8346	Intermediate Similarity	NPC166480
0.8346	Intermediate Similarity	NPC188646
0.8346	Intermediate Similarity	NPC337373
0.8346	Intermediate Similarity	NPC20560
0.8346	Intermediate Similarity	NPC82225
0.8346	Intermediate Similarity	NPC472365
0.8346	Intermediate Similarity	NPC192304
0.8346	Intermediate Similarity	NPC242294
0.8346	Intermediate Similarity	NPC312318
0.8346	Intermediate Similarity	NPC56031
0.8346	Intermediate Similarity	NPC28753
0.8346	Intermediate Similarity	NPC18877
0.8346	Intermediate Similarity	NPC144051
0.8346	Intermediate Similarity	NPC139813
0.8346	Intermediate Similarity	NPC159623
0.8346	Intermediate Similarity	NPC263670
0.8346	Intermediate Similarity	NPC282780
0.8333	Intermediate Similarity	NPC80027
0.8333	Intermediate Similarity	NPC114682
0.8333	Intermediate Similarity	NPC135801
0.8333	Intermediate Similarity	NPC475589
0.8333	Intermediate Similarity	NPC31872
0.8333	Intermediate Similarity	NPC113006
0.8333	Intermediate Similarity	NPC473584
0.8333	Intermediate Similarity	NPC280869
0.832	Intermediate Similarity	NPC84772
0.832	Intermediate Similarity	NPC62219
0.832	Intermediate Similarity	NPC147757
0.832	Intermediate Similarity	NPC42292
0.832	Intermediate Similarity	NPC307732
0.832	Intermediate Similarity	NPC185497
0.832	Intermediate Similarity	NPC12694
0.8319	Intermediate Similarity	NPC285829
0.8319	Intermediate Similarity	NPC206778
0.8319	Intermediate Similarity	NPC95172
0.8319	Intermediate Similarity	NPC72977
0.8306	Intermediate Similarity	NPC179898
0.8306	Intermediate Similarity	NPC293453
0.8293	Intermediate Similarity	NPC160499
0.8293	Intermediate Similarity	NPC328983
0.8291	Intermediate Similarity	NPC108288
0.8281	Intermediate Similarity	NPC283590
0.8281	Intermediate Similarity	NPC470210
0.8281	Intermediate Similarity	NPC164136
0.8281	Intermediate Similarity	NPC70859
0.8281	Intermediate Similarity	NPC61153
0.8281	Intermediate Similarity	NPC161632

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 NPC118288 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	336
0.1-0.2	1001
0.2-0.3	1510
0.3-0.4	2957
0.4-0.5	1950
0.5-0.6	1015
0.6-0.7	295
0.7-0.8	69
0.8-0.85	12
0.85-0.9	5
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8727	High Similarity	NPD9266	Approved
0.8727	High Similarity	NPD74	Approved
0.8636	High Similarity	NPD9267	Approved
0.8636	High Similarity	NPD9264	Approved
0.8636	High Similarity	NPD9263	Approved
0.8609	High Similarity	NPD9493	Approved
0.848	Intermediate Similarity	NPD1240	Approved
0.8346	Intermediate Similarity	NPD1607	Approved
0.8333	Intermediate Similarity	NPD1201	Approved
0.8333	Intermediate Similarity	NPD943	Approved
0.8291	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.8273	Intermediate Similarity	NPD9261	Approved
0.8182	Intermediate Similarity	NPD846	Approved
0.8182	Intermediate Similarity	NPD940	Approved
0.812	Intermediate Similarity	NPD9281	Approved
0.8077	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.8077	Intermediate Similarity	NPD1510	Phase 2
0.8077	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.8065	Intermediate Similarity	NPD1470	Approved
0.7982	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7967	Intermediate Similarity	NPD9717	Approved
0.7955	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7955	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.792	Intermediate Similarity	NPD1164	Approved
0.791	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7895	Intermediate Similarity	NPD1549	Phase 2
0.7778	Intermediate Similarity	NPD1203	Approved
0.7761	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7744	Intermediate Similarity	NPD1551	Phase 2
0.7705	Intermediate Similarity	NPD9545	Approved
0.7681	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7642	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7609	Intermediate Similarity	NPD1511	Approved
0.7609	Intermediate Similarity	NPD7390	Discontinued
0.7554	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7542	Intermediate Similarity	NPD4750	Phase 3
0.754	Intermediate Similarity	NPD9269	Phase 2
0.75	Intermediate Similarity	NPD9268	Approved
0.75	Intermediate Similarity	NPD1512	Approved
0.7481	Intermediate Similarity	NPD2796	Approved
0.746	Intermediate Similarity	NPD422	Phase 1
0.7456	Intermediate Similarity	NPD1242	Phase 1
0.7442	Intermediate Similarity	NPD2798	Approved
0.7424	Intermediate Similarity	NPD520	Approved
0.7391	Intermediate Similarity	NPD3750	Approved
0.7388	Intermediate Similarity	NPD6651	Approved
0.7357	Intermediate Similarity	NPD6799	Approved
0.7353	Intermediate Similarity	NPD5408	Approved
0.7353	Intermediate Similarity	NPD5404	Approved
0.7353	Intermediate Similarity	NPD2935	Discontinued
0.7353	Intermediate Similarity	NPD5406	Approved
0.7353	Intermediate Similarity	NPD5405	Approved
0.7348	Intermediate Similarity	NPD411	Approved
0.7323	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7319	Intermediate Similarity	NPD2800	Approved
0.7313	Intermediate Similarity	NPD447	Suspended
0.7313	Intermediate Similarity	NPD230	Phase 1
0.731	Intermediate Similarity	NPD1934	Approved
0.7292	Intermediate Similarity	NPD4380	Phase 2
0.728	Intermediate Similarity	NPD1759	Phase 1
0.7273	Intermediate Similarity	NPD9256	Approved
0.7273	Intermediate Similarity	NPD9258	Approved
0.7265	Intermediate Similarity	NPD1237	Approved
0.726	Intermediate Similarity	NPD2801	Approved
0.726	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7257	Intermediate Similarity	NPD844	Approved
0.7241	Intermediate Similarity	NPD7411	Suspended
0.7232	Intermediate Similarity	NPD845	Approved
0.7211	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7203	Intermediate Similarity	NPD5403	Approved
0.72	Intermediate Similarity	NPD1758	Phase 1
0.7197	Intermediate Similarity	NPD6832	Phase 2
0.7194	Intermediate Similarity	NPD1243	Approved
0.7194	Intermediate Similarity	NPD2654	Approved
0.7193	Intermediate Similarity	NPD288	Approved
0.7183	Intermediate Similarity	NPD5401	Approved
0.7176	Intermediate Similarity	NPD1019	Discontinued
0.7174	Intermediate Similarity	NPD2344	Approved
0.717	Intermediate Similarity	NPD9089	Approved
0.7168	Intermediate Similarity	NPD2934	Approved
0.7168	Intermediate Similarity	NPD2933	Approved
0.7162	Intermediate Similarity	NPD3882	Suspended
0.7155	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.713	Intermediate Similarity	NPD111	Approved
0.7114	Intermediate Similarity	NPD7075	Discontinued
0.7105	Intermediate Similarity	NPD2859	Approved
0.7105	Intermediate Similarity	NPD2860	Approved
0.7099	Intermediate Similarity	NPD2797	Approved
0.709	Intermediate Similarity	NPD2313	Discontinued
0.709	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD9093	Approved
0.7063	Intermediate Similarity	NPD2533	Approved
0.7063	Intermediate Similarity	NPD2532	Approved
0.7063	Intermediate Similarity	NPD2534	Approved
0.7055	Intermediate Similarity	NPD6599	Discontinued
0.7047	Intermediate Similarity	NPD7768	Phase 2
0.704	Intermediate Similarity	NPD255	Approved
0.704	Intermediate Similarity	NPD256	Approved
0.7029	Intermediate Similarity	NPD2799	Discontinued
0.7029	Intermediate Similarity	NPD3748	Approved
0.7027	Intermediate Similarity	NPD7819	Suspended
0.7027	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.7016	Intermediate Similarity	NPD1241	Discontinued
0.7008	Intermediate Similarity	NPD1548	Phase 1
0.7	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD3749	Approved
0.6983	Remote Similarity	NPD9273	Approved
0.6978	Remote Similarity	NPD6100	Approved
0.6978	Remote Similarity	NPD6099	Approved
0.6972	Remote Similarity	NPD2309	Approved
0.6963	Remote Similarity	NPD3268	Approved
0.6963	Remote Similarity	NPD3764	Approved
0.6959	Remote Similarity	NPD6801	Discontinued
0.6957	Remote Similarity	NPD9279	Approved
0.6957	Remote Similarity	NPD1809	Phase 2
0.6923	Remote Similarity	NPD3020	Approved
0.6923	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD3300	Phase 2
0.6909	Remote Similarity	NPD9259	Approved
0.6909	Remote Similarity	NPD9257	Approved
0.6906	Remote Similarity	NPD4308	Phase 3
0.6901	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD1196	Approved
0.6899	Remote Similarity	NPD3019	Approved
0.6899	Remote Similarity	NPD2932	Approved
0.6885	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD1543	Discontinued
0.6867	Remote Similarity	NPD3817	Phase 2
0.6867	Remote Similarity	NPD5402	Approved
0.685	Remote Similarity	NPD9568	Approved
0.6849	Remote Similarity	NPD920	Approved
0.6839	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD6166	Phase 2
0.6839	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6838	Remote Similarity	NPD1296	Phase 2
0.6838	Remote Similarity	NPD9495	Approved
0.6831	Remote Similarity	NPD1195	Approved
0.6831	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6828	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD6232	Discontinued
0.6818	Remote Similarity	NPD1755	Approved
0.6812	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6812	Remote Similarity	NPD1933	Approved
0.6809	Remote Similarity	NPD2346	Discontinued
0.6795	Remote Similarity	NPD7473	Discontinued
0.6794	Remote Similarity	NPD1610	Phase 2
0.6789	Remote Similarity	NPD9491	Approved
0.6786	Remote Similarity	NPD9094	Approved
0.6783	Remote Similarity	NPD1202	Approved
0.6767	Remote Similarity	NPD3225	Approved
0.6761	Remote Similarity	NPD9277	Approved
0.6761	Remote Similarity	NPD75	Approved
0.6757	Remote Similarity	NPD3226	Approved
0.6753	Remote Similarity	NPD6959	Discontinued
0.675	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.675	Remote Similarity	NPD1929	Approved
0.675	Remote Similarity	NPD1930	Approved
0.6742	Remote Similarity	NPD3972	Approved
0.6742	Remote Similarity	NPD1608	Approved
0.6741	Remote Similarity	NPD9494	Approved
0.6716	Remote Similarity	NPD3266	Approved
0.6716	Remote Similarity	NPD3267	Approved
0.6712	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6709	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6709	Remote Similarity	NPD7054	Approved
0.6692	Remote Similarity	NPD4749	Approved
0.669	Remote Similarity	NPD9278	Suspended
0.669	Remote Similarity	NPD9275	Approved
0.669	Remote Similarity	NPD9274	Approved
0.669	Remote Similarity	NPD9276	Approved
0.6667	Remote Similarity	NPD7074	Phase 3
0.6667	Remote Similarity	NPD7472	Approved
0.6667	Remote Similarity	NPD3299	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD3818	Discontinued
0.6642	Remote Similarity	NPD1876	Approved
0.6639	Remote Similarity	NPD2066	Phase 3
0.6625	Remote Similarity	NPD5953	Discontinued
0.6625	Remote Similarity	NPD6797	Phase 2
0.6619	Remote Similarity	NPD468	Phase 1
0.6619	Remote Similarity	NPD4307	Phase 2
0.6617	Remote Similarity	NPD1481	Phase 2
0.6604	Remote Similarity	NPD7286	Phase 2
0.6604	Remote Similarity	NPD6020	Phase 2
0.6587	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6584	Remote Similarity	NPD7251	Discontinued
0.6584	Remote Similarity	NPD6559	Discontinued
0.6581	Remote Similarity	NPD1693	Approved
0.6579	Remote Similarity	NPD800	Approved
0.6569	Remote Similarity	NPD1008	Clinical (unspecified phase)
0.6569	Remote Similarity	NPD4908	Phase 1
0.6562	Remote Similarity	NPD5951	Approved
0.6562	Remote Similarity	NPD1729	Discontinued
0.6562	Remote Similarity	NPD1476	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD690	Clinical (unspecified phase)
0.656	Remote Similarity	NPD9380	Clinical (unspecified phase)
0.6557	Remote Similarity	NPD164	Approved
0.6557	Remote Similarity	NPD9610	Approved
0.6557	Remote Similarity	NPD9608	Approved

Bioactivity similarity: Similar Natural Products in NPASS

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

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

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data