NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	178.06
Volume:	186.148
LogP:	2.132
LogD:	1.816
LogS:	-2.128
# Rotatable Bonds:	2
TPSA:	54.37
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	1
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.551
Synthetic Accessibility Score:	2.084
Fsp3:	0.2
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.487
MDCK Permeability:	1.9728086044779047e-05
Pgp-inhibitor:	0.002
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.006
30% Bioavailability (F30%):	0.234

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.287
Plasma Protein Binding (PPB):	92.03302764892578%
Volume Distribution (VD):	0.399
Pgp-substrate:	3.776176929473877%

ADMET: Metabolism

CYP1A2-inhibitor:	0.953
CYP1A2-substrate:	0.871
CYP2C19-inhibitor:	0.56
CYP2C19-substrate:	0.083
CYP2C9-inhibitor:	0.397
CYP2C9-substrate:	0.659
CYP2D6-inhibitor:	0.359
CYP2D6-substrate:	0.482
CYP3A4-inhibitor:	0.113
CYP3A4-substrate:	0.261

ADMET: Excretion

Clearance (CL):	5.206
Half-life (T1/2):	0.685

ADMET: Toxicity

hERG Blockers:	0.028
Human Hepatotoxicity (H-HT):	0.041
Drug-inuced Liver Injury (DILI):	0.597
AMES Toxicity:	0.628
Rat Oral Acute Toxicity:	0.223
Maximum Recommended Daily Dose:	0.509
Skin Sensitization:	0.642
Carcinogencity:	0.523
Eye Corrosion:	0.747
Eye Irritation:	0.99
Respiratory Toxicity:	0.53

Download Data

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

Natural Product: NPC161304

Natural Product ID:	NPC161304
*Common Name:**	1-(2-Hydroxy-4-Methylphenyl)Propan-1,2-Dione
IUPAC Name:	1-(2-hydroxy-4-methylphenyl)propane-1,2-dione
Synonyms:
Standard InCHIKey:	OXDKWKNIBKTRLQ-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C10H10O3/c1-6-3-4-8(9(12)5-6)10(13)7(2)11/h3-5,12H,1-2H3
SMILES:	Cc1ccc(c(c1)O)C(=O)C(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1795989
PubChem CID:	53355239
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0002811] Phenylpropanes

*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
NPO6414	Eupatorium cannabinum	Species	Asteraceae	Eukaryota	n.a.	aerial part	n.a.	PMID[21391659]
NPO6414	Eupatorium cannabinum	Species	Asteraceae	Eukaryota	Aerial Parts	n.a.	n.a.	PMID[30653318]
NPO6414	Eupatorium cannabinum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO6414	Eupatorium cannabinum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6414	Eupatorium cannabinum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO6414	Eupatorium cannabinum	Species	Asteraceae	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
Others	2

Activity Type	# Activity
NON-MOLECULAR	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	10.1	%	PMID[525993]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	37.3	%	PMID[525993]

☑ 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 NPC161304 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	272
0.1-0.2	1690
0.2-0.3	4319
0.3-0.4	11619
0.4-0.5	7418
0.5-0.6	6793
0.6-0.7	7918
0.7-0.8	2298
0.8-0.85	263
0.85-0.9	94
0.9-0.95	12
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.955	High Similarity	NPC41567
0.9455	High Similarity	NPC240163
0.9346	High Similarity	NPC224584
0.9304	High Similarity	NPC307174
0.9286	High Similarity	NPC269414
0.9252	High Similarity	NPC34715
0.9211	High Similarity	NPC285829
0.9211	High Similarity	NPC206778
0.9196	High Similarity	NPC477453
0.9115	High Similarity	NPC160199
0.9027	High Similarity	NPC108288
0.8983	High Similarity	NPC142956
0.8974	High Similarity	NPC300274
0.8908	High Similarity	NPC287473
0.8898	High Similarity	NPC375356
0.8898	High Similarity	NPC477153
0.8843	High Similarity	NPC282923
0.8843	High Similarity	NPC48248
0.8833	High Similarity	NPC3224
0.8833	High Similarity	NPC306765
0.8833	High Similarity	NPC231774
0.8824	High Similarity	NPC74507
0.8824	High Similarity	NPC68756
0.8824	High Similarity	NPC173978
0.8824	High Similarity	NPC234890
0.8824	High Similarity	NPC310540
0.8824	High Similarity	NPC152525
0.8803	High Similarity	NPC165197
0.8783	High Similarity	NPC125252
0.877	High Similarity	NPC146647
0.877	High Similarity	NPC34414
0.875	High Similarity	NPC103540
0.8729	High Similarity	NPC25168
0.8727	High Similarity	NPC141523
0.8718	High Similarity	NPC216297
0.8718	High Similarity	NPC473662
0.8718	High Similarity	NPC7151
0.8707	High Similarity	NPC171023
0.8684	High Similarity	NPC276111
0.8684	High Similarity	NPC163154
0.8684	High Similarity	NPC118288
0.8678	High Similarity	NPC227741
0.8678	High Similarity	NPC49647
0.8678	High Similarity	NPC160499
0.8678	High Similarity	NPC96915
0.8678	High Similarity	NPC136342
0.8678	High Similarity	NPC295202
0.8655	High Similarity	NPC297193
0.8644	High Similarity	NPC115188
0.8644	High Similarity	NPC159760
0.8644	High Similarity	NPC272454
0.8644	High Similarity	NPC179092
0.8644	High Similarity	NPC222876
0.8644	High Similarity	NPC244994
0.8644	High Similarity	NPC301987
0.8644	High Similarity	NPC292665
0.8644	High Similarity	NPC26433
0.8644	High Similarity	NPC35856
0.8644	High Similarity	NPC178395
0.8632	High Similarity	NPC232178
0.8632	High Similarity	NPC233165
0.8632	High Similarity	NPC184579
0.8629	High Similarity	NPC205992
0.8621	High Similarity	NPC121259
0.8618	High Similarity	NPC109123
0.8618	High Similarity	NPC99731
0.8596	High Similarity	NPC242136
0.8596	High Similarity	NPC211421
0.8595	High Similarity	NPC131799
0.8571	High Similarity	NPC95172
0.8559	High Similarity	NPC303264
0.8559	High Similarity	NPC226699
0.8559	High Similarity	NPC294964
0.8548	High Similarity	NPC199253
0.8548	High Similarity	NPC55949
0.8548	High Similarity	NPC198305
0.8548	High Similarity	NPC136588
0.8537	High Similarity	NPC237225
0.8534	High Similarity	NPC312800
0.8525	High Similarity	NPC8745
0.8525	High Similarity	NPC51037
0.8512	High Similarity	NPC236189
0.8512	High Similarity	NPC117794
0.8509	High Similarity	NPC231717
0.85	High Similarity	NPC282577
0.8492	Intermediate Similarity	NPC115458
0.8492	Intermediate Similarity	NPC53896
0.8492	Intermediate Similarity	NPC225051
0.8487	Intermediate Similarity	NPC190971
0.8482	Intermediate Similarity	NPC100551
0.848	Intermediate Similarity	NPC244699
0.8475	Intermediate Similarity	NPC161617
0.8468	Intermediate Similarity	NPC6984
0.8468	Intermediate Similarity	NPC187913
0.8468	Intermediate Similarity	NPC278928
0.8462	Intermediate Similarity	NPC150919
0.8462	Intermediate Similarity	NPC28169
0.8455	Intermediate Similarity	NPC471530
0.8443	Intermediate Similarity	NPC472592
0.8443	Intermediate Similarity	NPC10926
0.843	Intermediate Similarity	NPC275145
0.8425	Intermediate Similarity	NPC50924
0.8421	Intermediate Similarity	NPC114682
0.8413	Intermediate Similarity	NPC309430
0.8413	Intermediate Similarity	NPC110609
0.8413	Intermediate Similarity	NPC242358
0.8413	Intermediate Similarity	NPC246693
0.8413	Intermediate Similarity	NPC58685
0.8413	Intermediate Similarity	NPC70622
0.84	Intermediate Similarity	NPC475741
0.84	Intermediate Similarity	NPC117609
0.84	Intermediate Similarity	NPC31799
0.84	Intermediate Similarity	NPC31539
0.839	Intermediate Similarity	NPC184527
0.8387	Intermediate Similarity	NPC165257
0.8378	Intermediate Similarity	NPC163734
0.8376	Intermediate Similarity	NPC128825
0.8374	Intermediate Similarity	NPC1991
0.8362	Intermediate Similarity	NPC81808
0.8361	Intermediate Similarity	NPC4012
0.8361	Intermediate Similarity	NPC13238
0.8359	Intermediate Similarity	NPC161632
0.8359	Intermediate Similarity	NPC80035
0.8359	Intermediate Similarity	NPC283088
0.8347	Intermediate Similarity	NPC217756
0.8347	Intermediate Similarity	NPC283514
0.8347	Intermediate Similarity	NPC309765
0.8347	Intermediate Similarity	NPC244351
0.8346	Intermediate Similarity	NPC52407
0.8346	Intermediate Similarity	NPC171968
0.8333	Intermediate Similarity	NPC72669
0.8333	Intermediate Similarity	NPC146642
0.8333	Intermediate Similarity	NPC474517
0.8319	Intermediate Similarity	NPC188814
0.8319	Intermediate Similarity	NPC473767
0.8319	Intermediate Similarity	NPC195262
0.8295	Intermediate Similarity	NPC155211
0.8295	Intermediate Similarity	NPC474813
0.8295	Intermediate Similarity	NPC272268
0.8293	Intermediate Similarity	NPC477454
0.8293	Intermediate Similarity	NPC167055
0.8293	Intermediate Similarity	NPC123506
0.8293	Intermediate Similarity	NPC240744
0.8281	Intermediate Similarity	NPC288089
0.8279	Intermediate Similarity	NPC135062
0.8273	Intermediate Similarity	NPC25458
0.8268	Intermediate Similarity	NPC477406
0.8264	Intermediate Similarity	NPC156139
0.8264	Intermediate Similarity	NPC198336
0.8264	Intermediate Similarity	NPC120545
0.8264	Intermediate Similarity	NPC303737
0.8257	Intermediate Similarity	NPC280869
0.8254	Intermediate Similarity	NPC278787
0.825	Intermediate Similarity	NPC260837
0.825	Intermediate Similarity	NPC294037
0.824	Intermediate Similarity	NPC95537
0.824	Intermediate Similarity	NPC96024
0.8235	Intermediate Similarity	NPC40649
0.8235	Intermediate Similarity	NPC94637
0.8235	Intermediate Similarity	NPC209486
0.8231	Intermediate Similarity	NPC53414
0.8231	Intermediate Similarity	NPC53206
0.8231	Intermediate Similarity	NPC245923
0.8226	Intermediate Similarity	NPC254492
0.8226	Intermediate Similarity	NPC473751
0.8226	Intermediate Similarity	NPC473691
0.8217	Intermediate Similarity	NPC258502
0.8217	Intermediate Similarity	NPC281513
0.8217	Intermediate Similarity	NPC22222
0.8211	Intermediate Similarity	NPC56332
0.8211	Intermediate Similarity	NPC199273
0.8211	Intermediate Similarity	NPC91475
0.8211	Intermediate Similarity	NPC265910
0.8203	Intermediate Similarity	NPC254603
0.8203	Intermediate Similarity	NPC294226
0.8203	Intermediate Similarity	NPC314048
0.8198	Intermediate Similarity	NPC13426
0.8197	Intermediate Similarity	NPC91478
0.8197	Intermediate Similarity	NPC32032
0.8197	Intermediate Similarity	NPC133909
0.8197	Intermediate Similarity	NPC46634
0.8189	Intermediate Similarity	NPC141549
0.8189	Intermediate Similarity	NPC17083
0.8189	Intermediate Similarity	NPC85342
0.8189	Intermediate Similarity	NPC324488
0.8182	Intermediate Similarity	NPC472046
0.8182	Intermediate Similarity	NPC149246
0.8182	Intermediate Similarity	NPC297186
0.8175	Intermediate Similarity	NPC92624
0.8175	Intermediate Similarity	NPC25736
0.8168	Intermediate Similarity	NPC4214
0.8168	Intermediate Similarity	NPC13715
0.8168	Intermediate Similarity	NPC61398
0.8168	Intermediate Similarity	NPC416
0.8167	Intermediate Similarity	NPC328459
0.8167	Intermediate Similarity	NPC90522
0.8165	Intermediate Similarity	NPC260000
0.816	Intermediate Similarity	NPC470841
0.816	Intermediate Similarity	NPC71525
0.816	Intermediate Similarity	NPC72667

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 NPC161304 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	301
0.1-0.2	988
0.2-0.3	1370
0.3-0.4	2706
0.4-0.5	2148
0.5-0.6	1141
0.6-0.7	405
0.7-0.8	79
0.8-0.85	9
0.85-0.9	2
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9027	High Similarity	NPD405	Clinical (unspecified phase)
0.875	High Similarity	NPD1470	Approved
0.8729	High Similarity	NPD1201	Approved
0.8482	Intermediate Similarity	NPD9266	Approved
0.8482	Intermediate Similarity	NPD74	Approved
0.8393	Intermediate Similarity	NPD9264	Approved
0.8393	Intermediate Similarity	NPD9267	Approved
0.8393	Intermediate Similarity	NPD9263	Approved
0.8376	Intermediate Similarity	NPD9493	Approved
0.8154	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.8148	Intermediate Similarity	NPD844	Approved
0.8125	Intermediate Similarity	NPD943	Approved
0.8073	Intermediate Similarity	NPD288	Approved
0.8036	Intermediate Similarity	NPD9261	Approved
0.8	Intermediate Similarity	NPD1164	Approved
0.7899	Intermediate Similarity	NPD9281	Approved
0.7869	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7863	Intermediate Similarity	NPD1607	Approved
0.7829	Intermediate Similarity	NPD411	Approved
0.7795	Intermediate Similarity	NPD2798	Approved
0.7761	Intermediate Similarity	NPD2346	Discontinued
0.776	Intermediate Similarity	NPD9717	Approved
0.7759	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7744	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.771	Intermediate Similarity	NPD1240	Approved
0.7699	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.7687	Intermediate Similarity	NPD5408	Approved
0.7687	Intermediate Similarity	NPD2935	Discontinued
0.7687	Intermediate Similarity	NPD5406	Approved
0.7687	Intermediate Similarity	NPD5404	Approved
0.7687	Intermediate Similarity	NPD5405	Approved
0.7652	Intermediate Similarity	NPD447	Suspended
0.763	Intermediate Similarity	NPD2344	Approved
0.7578	Intermediate Similarity	NPD1203	Approved
0.7557	Intermediate Similarity	NPD2313	Discontinued
0.754	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.752	Intermediate Similarity	NPD2932	Approved
0.752	Intermediate Similarity	NPD3019	Approved
0.75	Intermediate Similarity	NPD9545	Approved
0.75	Intermediate Similarity	NPD1237	Approved
0.7481	Intermediate Similarity	NPD1510	Phase 2
0.7481	Intermediate Similarity	NPD2799	Discontinued
0.7429	Intermediate Similarity	NPD7390	Discontinued
0.7413	Intermediate Similarity	NPD3226	Approved
0.741	Intermediate Similarity	NPD2309	Approved
0.7364	Intermediate Similarity	NPD9258	Approved
0.7364	Intermediate Similarity	NPD9256	Approved
0.7357	Intermediate Similarity	NPD3300	Phase 2
0.7338	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD4750	Phase 3
0.7328	Intermediate Similarity	NPD9494	Approved
0.7321	Intermediate Similarity	NPD845	Approved
0.7299	Intermediate Similarity	NPD1551	Phase 2
0.7287	Intermediate Similarity	NPD1755	Approved
0.7257	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.7254	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD520	Approved
0.7226	Intermediate Similarity	NPD4308	Phase 3
0.7209	Intermediate Similarity	NPD3972	Approved
0.7209	Intermediate Similarity	NPD9269	Phase 2
0.7194	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7194	Intermediate Similarity	NPD1549	Phase 2
0.7193	Intermediate Similarity	NPD2859	Approved
0.7193	Intermediate Similarity	NPD2860	Approved
0.7179	Intermediate Similarity	NPD940	Approved
0.7179	Intermediate Similarity	NPD1932	Approved
0.7179	Intermediate Similarity	NPD846	Approved
0.7177	Intermediate Similarity	NPD5951	Approved
0.7167	Intermediate Similarity	NPD2342	Discontinued
0.7165	Intermediate Similarity	NPD9268	Approved
0.7164	Intermediate Similarity	NPD3764	Approved
0.7155	Intermediate Similarity	NPD3020	Approved
0.7155	Intermediate Similarity	NPD2066	Phase 3
0.7154	Intermediate Similarity	NPD7635	Approved
0.7122	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7122	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.712	Intermediate Similarity	NPD256	Approved
0.712	Intermediate Similarity	NPD255	Approved
0.7119	Intermediate Similarity	NPD1929	Approved
0.7119	Intermediate Similarity	NPD1930	Approved
0.7119	Intermediate Similarity	NPD1931	Clinical (unspecified phase)
0.7109	Intermediate Similarity	NPD4626	Approved
0.7107	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD2934	Approved
0.7105	Intermediate Similarity	NPD2933	Approved
0.7101	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD1283	Approved
0.7097	Intermediate Similarity	NPD1241	Discontinued
0.7073	Intermediate Similarity	NPD1609	Clinical (unspecified phase)
0.7064	Intermediate Similarity	NPD111	Approved
0.7063	Intermediate Similarity	NPD1511	Approved
0.7043	Intermediate Similarity	NPD1809	Phase 2
0.7031	Intermediate Similarity	NPD1651	Approved
0.7015	Intermediate Similarity	NPD6832	Phase 2
0.7014	Intermediate Similarity	NPD2532	Approved
0.7014	Intermediate Similarity	NPD2534	Approved
0.7014	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7014	Intermediate Similarity	NPD2533	Approved
0.7007	Intermediate Similarity	NPD230	Phase 1
0.7007	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD9259	Approved
0.7	Intermediate Similarity	NPD1471	Phase 3
0.7	Intermediate Similarity	NPD9257	Approved
0.6993	Remote Similarity	NPD6884	Clinical (unspecified phase)
0.6992	Remote Similarity	NPD1019	Discontinued
0.6977	Remote Similarity	NPD1778	Approved
0.6972	Remote Similarity	NPD7003	Approved
0.697	Remote Similarity	NPD1876	Approved
0.6967	Remote Similarity	NPD2329	Discontinued
0.6966	Remote Similarity	NPD1512	Approved
0.6964	Remote Similarity	NPD800	Approved
0.6957	Remote Similarity	NPD1693	Approved
0.6953	Remote Similarity	NPD1759	Phase 1
0.6947	Remote Similarity	NPD1608	Approved
0.6942	Remote Similarity	NPD1444	Approved
0.6942	Remote Similarity	NPD1445	Approved
0.6935	Remote Similarity	NPD9508	Approved
0.6934	Remote Similarity	NPD4307	Phase 2
0.6929	Remote Similarity	NPD2796	Approved
0.6923	Remote Similarity	NPD3023	Approved
0.6923	Remote Similarity	NPD3026	Approved
0.6917	Remote Similarity	NPD2797	Approved
0.6913	Remote Similarity	NPD1934	Approved
0.6911	Remote Similarity	NPD3022	Approved
0.6911	Remote Similarity	NPD1317	Discontinued
0.6911	Remote Similarity	NPD3021	Approved
0.6903	Remote Similarity	NPD1089	Approved
0.6903	Remote Similarity	NPD1086	Approved
0.6903	Remote Similarity	NPD1090	Approved
0.6899	Remote Similarity	NPD3024	Approved
0.6899	Remote Similarity	NPD3025	Approved
0.6897	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD3882	Suspended
0.6879	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD1758	Phase 1
0.687	Remote Similarity	NPD1202	Approved
0.687	Remote Similarity	NPD1281	Approved
0.6867	Remote Similarity	NPD2801	Approved
0.6867	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6866	Remote Similarity	NPD258	Approved
0.6866	Remote Similarity	NPD257	Approved
0.6853	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6853	Remote Similarity	NPD3750	Approved
0.685	Remote Similarity	NPD6671	Approved
0.6846	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD2296	Approved
0.6818	Remote Similarity	NPD4878	Approved
0.6809	Remote Similarity	NPD6099	Approved
0.6809	Remote Similarity	NPD6100	Approved
0.6807	Remote Similarity	NPD1242	Phase 1
0.68	Remote Similarity	NPD6844	Discontinued
0.6797	Remote Similarity	NPD9568	Approved
0.6788	Remote Similarity	NPD3268	Approved
0.6786	Remote Similarity	NPD9279	Approved
0.6783	Remote Similarity	NPD2800	Approved
0.6783	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6783	Remote Similarity	NPD1088	Approved
0.678	Remote Similarity	NPD9495	Approved
0.6779	Remote Similarity	NPD4380	Phase 2
0.6777	Remote Similarity	NPD164	Approved
0.6774	Remote Similarity	NPD6232	Discontinued
0.6774	Remote Similarity	NPD1792	Phase 2
0.6772	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6769	Remote Similarity	NPD5691	Approved
0.6767	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6755	Remote Similarity	NPD7819	Suspended
0.6752	Remote Similarity	NPD7473	Discontinued
0.6739	Remote Similarity	NPD6663	Approved
0.6736	Remote Similarity	NPD8166	Discontinued
0.6736	Remote Similarity	NPD4628	Phase 3
0.6736	Remote Similarity	NPD1196	Approved
0.6727	Remote Similarity	NPD9491	Approved
0.672	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.672	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6718	Remote Similarity	NPD17	Approved
0.6712	Remote Similarity	NPD1543	Discontinued
0.6711	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6711	Remote Similarity	NPD7458	Discontinued
0.6696	Remote Similarity	NPD1239	Approved
0.6694	Remote Similarity	NPD9500	Approved
0.6691	Remote Similarity	NPD5736	Approved
0.6667	Remote Similarity	NPD1195	Approved
0.6667	Remote Similarity	NPD4661	Approved
0.6667	Remote Similarity	NPD3496	Discontinued
0.6667	Remote Similarity	NPD6599	Discontinued
0.6667	Remote Similarity	NPD4662	Approved
0.6667	Remote Similarity	NPD228	Approved
0.6667	Remote Similarity	NPD1243	Approved
0.6643	Remote Similarity	NPD1933	Approved
0.6642	Remote Similarity	NPD182	Clinical (unspecified phase)
0.6641	Remote Similarity	NPD497	Approved
0.6639	Remote Similarity	NPD9273	Approved
0.6637	Remote Similarity	NPD1087	Approved
0.6623	Remote Similarity	NPD3749	Approved
0.6623	Remote Similarity	NPD7411	Suspended
0.6623	Remote Similarity	NPD7075	Discontinued
0.6614	Remote Similarity	NPD5277	Phase 2
0.6603	Remote Similarity	NPD6959	Discontinued
0.6601	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6601	Remote Similarity	NPD5402	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