NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	146.08
Volume:	158.555
LogP:	2.285
LogD:	2.374
LogS:	-2.28
# Rotatable Bonds:	1
TPSA:	28.68
# H-Bond Aceptor:	2
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.656
Synthetic Accessibility Score:	1.809
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:	-4.627
MDCK Permeability:	3.003692108904943e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.094
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.864
30% Bioavailability (F30%):	0.063

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.866
Plasma Protein Binding (PPB):	83.48023223876953%
Volume Distribution (VD):	1.062
Pgp-substrate:	13.016623497009277%

ADMET: Metabolism

CYP1A2-inhibitor:	0.987
CYP1A2-substrate:	0.909
CYP2C19-inhibitor:	0.468
CYP2C19-substrate:	0.064
CYP2C9-inhibitor:	0.042
CYP2C9-substrate:	0.073
CYP2D6-inhibitor:	0.655
CYP2D6-substrate:	0.143
CYP3A4-inhibitor:	0.093
CYP3A4-substrate:	0.316

ADMET: Excretion

Clearance (CL):	5.476
Half-life (T1/2):	0.829

ADMET: Toxicity

hERG Blockers:	0.075
Human Hepatotoxicity (H-HT):	0.304
Drug-inuced Liver Injury (DILI):	0.291
AMES Toxicity:	0.034
Rat Oral Acute Toxicity:	0.967
Maximum Recommended Daily Dose:	0.887
Skin Sensitization:	0.197
Carcinogencity:	0.449
Eye Corrosion:	0.014
Eye Irritation:	0.939
Respiratory Toxicity:	0.97

Download Data

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

Natural Product: NPC216159

Natural Product ID:	NPC216159
*Common Name:**	2-Ethyl-1H-Benzimidazole
IUPAC Name:	2-ethyl-1H-benzimidazole
Synonyms:	2-Ethyl-Benzimidazole
Standard InCHIKey:	QHCCOYAKYCWDOJ-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C9H10N2/c1-2-9-10-7-5-3-4-6-8(7)11-9/h3-6H,2H2,1H3,(H,10,11)
SMILES:	CCc1nc2c([nH]1)cccc2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL351569
PubChem CID:	15807
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000294] Benzimidazoles

*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
NPO21355	Elsholtzia ciliata	Species	Lamiaceae	Eukaryota	Aerial Parts	n.a.	n.a.	PMID[32991171]
NPO18046	Mosla chinensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21355	Elsholtzia ciliata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18046	Mosla chinensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21355	Elsholtzia ciliata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18046	Mosla chinensis	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[TCM_Taiwan]
NPO18046	Mosla chinensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO21355	Elsholtzia ciliata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO18046	Mosla chinensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21355	Elsholtzia ciliata	Species	Lamiaceae	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	10
IC50	5
Ki	1
Others	10
Potency	2

Activity Type	# Activity
Cell Line	1
Individual Protein	11
NON-MOLECULAR	1
Organism	10
Others	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1775	Individual Protein	Cytochrome P450 2B1	Rattus norvegicus	IC50	=	676082.98	nM	PMID[482994]
NPT3895	Individual Protein	Cytochrome P450 1A1	Rattus norvegicus	IC50	=	630000.0	nM	PMID[482995]
NPT1775	Individual Protein	Cytochrome P450 2B1	Rattus norvegicus	IC50	=	670000.0	nM	PMID[482995]
NPT3895	Individual Protein	Cytochrome P450 1A1	Rattus norvegicus	IC50	=	630957.34	nM	PMID[482995]
NPT152	Individual Protein	Nuclear factor erythroid 2-related factor 2	Homo sapiens	Potency	n.a.	7307.8	nM	PMID[482996]
NPT3078	Individual Protein	N(G),N(G)-dimethylarginine dimethylaminohydrolase 1	Homo sapiens	Inhibition	=	4.0	%	PMID[482997]
NPT3078	Individual Protein	N(G),N(G)-dimethylarginine dimethylaminohydrolase 1	Homo sapiens	Inhibition	=	36.0	%	PMID[482997]
NPT3078	Individual Protein	N(G),N(G)-dimethylarginine dimethylaminohydrolase 1	Homo sapiens	Inhibition	=	25.0	%	PMID[482997]
NPT3078	Individual Protein	N(G),N(G)-dimethylarginine dimethylaminohydrolase 1	Homo sapiens	IC50	=	1400000.0	nM	PMID[482997]
NPT3078	Individual Protein	N(G),N(G)-dimethylarginine dimethylaminohydrolase 1	Homo sapiens	Ki	=	800000.0	nM	PMID[482997]
NPT25	Cell Line	MT4	Homo sapiens	CC50	>	100000.0	nM	PMID[482998]
NPT35	Others	n.a.		LogP	=	1.93	n.a.	PMID[482994]
NPT35	Others	n.a.		LogP	=	2.35	n.a.	PMID[482995]
NPT8	Individual Protein	DNA polymerase iota	Homo sapiens	Potency	n.a.	100000.0	nM	PMID[482996]
NPT2	Others	Unspecified		Inhibition	=	1.0	%	PMID[482997]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	EC50	>	100000.0	nM	PMID[482998]
NPT27	Others	Unspecified		CC50	>	100000.0	nM	PMID[482998]
NPT3573	Organism	Bovine viral diarrhea virus	Bovine viral diarrhea virus 1	EC50	>	100000.0	nM	PMID[482998]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	CC50	>	100000.0	nM	PMID[482998]
NPT4327	Organism	Yellow fever virus	Yellow fever virus	EC50	>	100000.0	nM	PMID[482998]
NPT337	Organism	Reovirus sp.	Reovirus sp.	EC50	>	100000.0	nM	PMID[482998]
NPT1539	Organism	Human coxsackievirus B5	Human coxsackievirus B5	EC50	>	100000.0	nM	PMID[482998]
NPT4691	Organism	Human poliovirus 1 strain Sabin	Human poliovirus 1 strain Sabin	EC50	>	100000.0	nM	PMID[482998]
NPT70	Organism	Respiratory syncytial virus	Respiratory syncytial virus	EC50	>	100000.0	nM	PMID[482998]
NPT195	Organism	Vesicular stomatitis virus	Vesicular stomatitis virus	EC50	>	100000.0	nM	PMID[482998]
NPT334	Organism	Vaccinia virus	Vaccinia virus	EC50	>	100000.0	nM	PMID[482998]
NPT190	Organism	Human herpesvirus 1	Human herpesvirus 1	EC50	>	100000.0	nM	PMID[482998]

☑ 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 NPC216159 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	4252
0.1-0.2	21323
0.2-0.3	10932
0.3-0.4	2687
0.4-0.5	2073
0.5-0.6	1171
0.6-0.7	226
0.7-0.8	26
0.8-0.85	3
0.85-0.9	0
0.9-0.95	2
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9137	High Similarity	NPC114209
0.9124	High Similarity	NPC42483
0.8267	Intermediate Similarity	NPC300238
0.7911	Intermediate Similarity	NPC314557
0.7812	Intermediate Similarity	NPC315715
0.7518	Intermediate Similarity	NPC75999
0.7484	Intermediate Similarity	NPC120070
0.7407	Intermediate Similarity	NPC143156
0.7368	Intermediate Similarity	NPC204141
0.7357	Intermediate Similarity	NPC41174
0.7317	Intermediate Similarity	NPC317054
0.7248	Intermediate Similarity	NPC125746
0.7226	Intermediate Similarity	NPC282531
0.7219	Intermediate Similarity	NPC115611
0.7188	Intermediate Similarity	NPC470204
0.7143	Intermediate Similarity	NPC470203
0.7114	Intermediate Similarity	NPC198988
0.7109	Intermediate Similarity	NPC317642
0.7105	Intermediate Similarity	NPC284635
0.7075	Intermediate Similarity	NPC22079
0.7067	Intermediate Similarity	NPC325252
0.7037	Intermediate Similarity	NPC253687
0.7034	Intermediate Similarity	NPC250361
0.7007	Intermediate Similarity	NPC473587
0.6975	Remote Similarity	NPC122141
0.6959	Remote Similarity	NPC475428
0.6954	Remote Similarity	NPC218268
0.6943	Remote Similarity	NPC201380
0.6943	Remote Similarity	NPC179787
0.6939	Remote Similarity	NPC473762
0.6937	Remote Similarity	NPC476219
0.6937	Remote Similarity	NPC476297
0.6913	Remote Similarity	NPC475450
0.6913	Remote Similarity	NPC179365
0.6906	Remote Similarity	NPC469308
0.6899	Remote Similarity	NPC321911
0.6879	Remote Similarity	NPC143872
0.6879	Remote Similarity	NPC63545
0.6866	Remote Similarity	NPC24060
0.6835	Remote Similarity	NPC469811
0.6818	Remote Similarity	NPC88097
0.6797	Remote Similarity	NPC84911
0.6788	Remote Similarity	NPC247987
0.6782	Remote Similarity	NPC476341
0.6763	Remote Similarity	NPC471609
0.6755	Remote Similarity	NPC473930
0.6732	Remote Similarity	NPC96102
0.6732	Remote Similarity	NPC261195
0.6732	Remote Similarity	NPC29886
0.671	Remote Similarity	NPC110126
0.671	Remote Similarity	NPC73767
0.6709	Remote Similarity	NPC470440
0.6689	Remote Similarity	NPC82295
0.6688	Remote Similarity	NPC105127
0.6667	Remote Similarity	NPC325903
0.6667	Remote Similarity	NPC59084
0.6667	Remote Similarity	NPC469779
0.6667	Remote Similarity	NPC2949
0.6667	Remote Similarity	NPC469761
0.6667	Remote Similarity	NPC232798
0.6667	Remote Similarity	NPC469780
0.6667	Remote Similarity	NPC469767
0.6667	Remote Similarity	NPC213774
0.6667	Remote Similarity	NPC469783
0.6667	Remote Similarity	NPC469768
0.6667	Remote Similarity	NPC469784
0.6646	Remote Similarity	NPC236711
0.6628	Remote Similarity	NPC473380
0.6628	Remote Similarity	NPC240088
0.6624	Remote Similarity	NPC63157
0.6624	Remote Similarity	NPC469766
0.6624	Remote Similarity	NPC197068
0.6624	Remote Similarity	NPC473868
0.662	Remote Similarity	NPC84268
0.6609	Remote Similarity	NPC307191
0.6607	Remote Similarity	NPC49217
0.659	Remote Similarity	NPC265710
0.6582	Remote Similarity	NPC190296
0.6561	Remote Similarity	NPC279081
0.6552	Remote Similarity	NPC16659
0.6541	Remote Similarity	NPC242556
0.6527	Remote Similarity	NPC225018
0.6525	Remote Similarity	NPC314141
0.6508	Remote Similarity	NPC116555
0.65	Remote Similarity	NPC314372
0.6497	Remote Similarity	NPC312092
0.6471	Remote Similarity	NPC278874
0.6458	Remote Similarity	NPC471603
0.6458	Remote Similarity	NPC148140
0.6456	Remote Similarity	NPC230002
0.642	Remote Similarity	NPC471957
0.642	Remote Similarity	NPC47596
0.642	Remote Similarity	NPC21605
0.642	Remote Similarity	NPC477134
0.6415	Remote Similarity	NPC88121
0.6414	Remote Similarity	NPC81561
0.641	Remote Similarity	NPC267811
0.6402	Remote Similarity	NPC469975
0.6398	Remote Similarity	NPC159856
0.6395	Remote Similarity	NPC476686
0.6395	Remote Similarity	NPC105758
0.6395	Remote Similarity	NPC476688
0.6391	Remote Similarity	NPC317105
0.638	Remote Similarity	NPC37548
0.638	Remote Similarity	NPC124005
0.638	Remote Similarity	NPC2272
0.6368	Remote Similarity	NPC187145
0.6358	Remote Similarity	NPC288838
0.6353	Remote Similarity	NPC280864
0.6353	Remote Similarity	NPC274229
0.6353	Remote Similarity	NPC17751
0.6347	Remote Similarity	NPC299594
0.6341	Remote Similarity	NPC105818
0.6341	Remote Similarity	NPC33421
0.6341	Remote Similarity	NPC53947
0.6341	Remote Similarity	NPC24678
0.6341	Remote Similarity	NPC148592
0.634	Remote Similarity	NPC282247
0.6335	Remote Similarity	NPC71238
0.631	Remote Similarity	NPC475990
0.631	Remote Similarity	NPC221786
0.631	Remote Similarity	NPC474880
0.6303	Remote Similarity	NPC470823
0.6303	Remote Similarity	NPC470233
0.6301	Remote Similarity	NPC82331
0.6291	Remote Similarity	NPC273714
0.6284	Remote Similarity	NPC215519
0.6272	Remote Similarity	NPC229173
0.6271	Remote Similarity	NPC88110
0.6265	Remote Similarity	NPC469763
0.6265	Remote Similarity	NPC469765
0.6265	Remote Similarity	NPC259644
0.6265	Remote Similarity	NPC469786
0.6265	Remote Similarity	NPC73952
0.6265	Remote Similarity	NPC200214
0.6265	Remote Similarity	NPC141926
0.6265	Remote Similarity	NPC469760
0.6265	Remote Similarity	NPC25008
0.6264	Remote Similarity	NPC208060
0.6259	Remote Similarity	NPC162689
0.6259	Remote Similarity	NPC54102
0.6258	Remote Similarity	NPC478186
0.6257	Remote Similarity	NPC108011
0.6243	Remote Similarity	NPC97343
0.6237	Remote Similarity	NPC54981
0.6228	Remote Similarity	NPC470507
0.6228	Remote Similarity	NPC211572
0.6228	Remote Similarity	NPC34844
0.6228	Remote Similarity	NPC471458
0.6228	Remote Similarity	NPC212376
0.6228	Remote Similarity	NPC80597
0.6228	Remote Similarity	NPC75540
0.6228	Remote Similarity	NPC70922
0.6228	Remote Similarity	NPC38736
0.622	Remote Similarity	NPC470111
0.6205	Remote Similarity	NPC216713
0.6199	Remote Similarity	NPC206148
0.6199	Remote Similarity	NPC271797
0.6199	Remote Similarity	NPC21174
0.6199	Remote Similarity	NPC271734
0.6193	Remote Similarity	NPC474958
0.6193	Remote Similarity	NPC151635
0.6193	Remote Similarity	NPC280852
0.619	Remote Similarity	NPC184476
0.619	Remote Similarity	NPC285469
0.6182	Remote Similarity	NPC288445
0.6182	Remote Similarity	NPC187951
0.617	Remote Similarity	NPC231655
0.6167	Remote Similarity	NPC21429
0.6162	Remote Similarity	NPC188821
0.6162	Remote Similarity	NPC474180
0.6159	Remote Similarity	NPC316069
0.6159	Remote Similarity	NPC129042
0.6154	Remote Similarity	NPC286427
0.6145	Remote Similarity	NPC477891
0.614	Remote Similarity	NPC224632
0.6127	Remote Similarity	NPC470509
0.6125	Remote Similarity	NPC104049
0.6125	Remote Similarity	NPC8590
0.6118	Remote Similarity	NPC318065
0.6118	Remote Similarity	NPC56765
0.6118	Remote Similarity	NPC206819
0.6118	Remote Similarity	NPC41257
0.6118	Remote Similarity	NPC122718
0.6118	Remote Similarity	NPC27740
0.6114	Remote Similarity	NPC54214
0.6101	Remote Similarity	NPC14448
0.6101	Remote Similarity	NPC98156
0.6101	Remote Similarity	NPC195704
0.6101	Remote Similarity	NPC200397
0.6101	Remote Similarity	NPC292434
0.6101	Remote Similarity	NPC167200
0.6101	Remote Similarity	NPC64661
0.6101	Remote Similarity	NPC138596
0.6099	Remote Similarity	NPC17273
0.6099	Remote Similarity	NPC141612
0.6099	Remote Similarity	NPC135601
0.6095	Remote Similarity	NPC469785
0.6095	Remote Similarity	NPC141353
0.6082	Remote Similarity	NPC473320

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 NPC216159 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	661
0.1-0.2	1124
0.2-0.3	1796
0.3-0.4	2130
0.4-0.5	2052
0.5-0.6	1009
0.6-0.7	314
0.7-0.8	59
0.8-0.85	4
0.85-0.9	0
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9124	High Similarity	NPD9724	Phase 1
0.8355	Intermediate Similarity	NPD2478	Clinical (unspecified phase)
0.8355	Intermediate Similarity	NPD2392	Clinical (unspecified phase)
0.8065	Intermediate Similarity	NPD773	Approved
0.8013	Intermediate Similarity	NPD2927	Phase 3
0.7986	Intermediate Similarity	NPD174	Discontinued
0.7962	Intermediate Similarity	NPD1567	Clinical (unspecified phase)
0.7901	Intermediate Similarity	NPD4441	Phase 2
0.7862	Intermediate Similarity	NPD1569	Phase 2
0.784	Intermediate Similarity	NPD4649	Clinical (unspecified phase)
0.7826	Intermediate Similarity	NPD5730	Phase 2
0.7826	Intermediate Similarity	NPD40	Phase 2
0.7821	Intermediate Similarity	NPD1333	Phase 3
0.7821	Intermediate Similarity	NPD509	Phase 3
0.7815	Intermediate Similarity	NPD2662	Approved
0.7815	Intermediate Similarity	NPD2128	Phase 1
0.7815	Intermediate Similarity	NPD2660	Approved
0.7806	Intermediate Similarity	NPD1016	Phase 2
0.7806	Intermediate Similarity	NPD1015	Phase 2
0.7778	Intermediate Similarity	NPD5962	Phase 2
0.7758	Intermediate Similarity	NPD2793	Discontinued
0.773	Intermediate Similarity	NPD412	Approved
0.7716	Intermediate Similarity	NPD676	Discontinued
0.7707	Intermediate Similarity	NPD1313	Approved
0.7683	Intermediate Similarity	NPD3512	Clinical (unspecified phase)
0.7669	Intermediate Similarity	NPD702	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD1043	Phase 3
0.7574	Intermediate Similarity	NPD3419	Clinical (unspecified phase)
0.7547	Intermediate Similarity	NPD4213	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD2930	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD2149	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD418	Approved
0.7467	Intermediate Similarity	NPD9254	Phase 3
0.7438	Intermediate Similarity	NPD3361	Phase 1
0.741	Intermediate Similarity	NPD1895	Discontinued
0.7383	Intermediate Similarity	NPD680	Discontinued
0.7368	Intermediate Similarity	NPD2892	Phase 1
0.7362	Intermediate Similarity	NPD5996	Clinical (unspecified phase)
0.7355	Intermediate Similarity	NPD2524	Discontinued
0.7346	Intermediate Similarity	NPD2875	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD1215	Discontinued
0.7301	Intermediate Similarity	NPD3418	Clinical (unspecified phase)
0.7301	Intermediate Similarity	NPD6828	Phase 2
0.7301	Intermediate Similarity	NPD6827	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD1029	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD1027	Approved
0.729	Intermediate Similarity	NPD1030	Approved
0.7267	Intermediate Similarity	NPD7709	Discontinued
0.7267	Intermediate Similarity	NPD3889	Approved
0.7235	Intermediate Similarity	NPD2591	Phase 2
0.7225	Intermediate Similarity	NPD1896	Approved
0.7222	Intermediate Similarity	NPD6794	Approved
0.7195	Intermediate Similarity	NPD3347	Clinical (unspecified phase)
0.7191	Intermediate Similarity	NPD6145	Phase 1
0.7178	Intermediate Similarity	NPD2333	Discontinued
0.717	Intermediate Similarity	NPD1869	Phase 2
0.7169	Intermediate Similarity	NPD5943	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD758	Approved
0.7143	Intermediate Similarity	NPD809	Discontinued
0.7135	Intermediate Similarity	NPD2963	Phase 1
0.7133	Intermediate Similarity	NPD1262	Discovery
0.7102	Intermediate Similarity	NPD2316	Clinical (unspecified phase)
0.7102	Intermediate Similarity	NPD774	Phase 3
0.7102	Intermediate Similarity	NPD1871	Approved
0.7089	Intermediate Similarity	NPD1303	Phase 1
0.7083	Intermediate Similarity	NPD3341	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD2137	Approved
0.7059	Intermediate Similarity	NPD2138	Approved
0.7052	Intermediate Similarity	NPD7884	Discontinued
0.7033	Intermediate Similarity	NPD6403	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD2731	Phase 2
0.7019	Intermediate Similarity	NPD1042	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD7006	Approved
0.7	Intermediate Similarity	NPD1290	Phase 2
0.6989	Remote Similarity	NPD6265	Discontinued
0.6982	Remote Similarity	NPD1327	Discontinued
0.6981	Remote Similarity	NPD695	Discontinued
0.6966	Remote Similarity	NPD2880	Discontinued
0.6937	Remote Similarity	NPD3405	Phase 3
0.6936	Remote Similarity	NPD3378	Clinical (unspecified phase)
0.6936	Remote Similarity	NPD5757	Discontinued
0.6923	Remote Similarity	NPD5013	Approved
0.6919	Remote Similarity	NPD5463	Clinical (unspecified phase)
0.6906	Remote Similarity	NPD4318	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD2009	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD2150	Discontinued
0.6864	Remote Similarity	NPD2406	Clinical (unspecified phase)
0.6855	Remote Similarity	NPD9709	Approved
0.6855	Remote Similarity	NPD9708	Approved
0.6851	Remote Similarity	NPD6816	Phase 3
0.6845	Remote Similarity	NPD966	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD645	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD3913	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD1272	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD1257	Approved
0.6809	Remote Similarity	NPD2794	Discontinued
0.6807	Remote Similarity	NPD438	Approved
0.6807	Remote Similarity	NPD439	Approved
0.6802	Remote Similarity	NPD1708	Approved
0.6802	Remote Similarity	NPD1707	Approved
0.6798	Remote Similarity	NPD3485	Clinical (unspecified phase)
0.6797	Remote Similarity	NPD544	Clinical (unspecified phase)
0.6796	Remote Similarity	NPD6264	Discontinued
0.6795	Remote Similarity	NPD4047	Discontinued
0.6782	Remote Similarity	NPD2868	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD7277	Approved
0.6772	Remote Similarity	NPD7276	Approved
0.677	Remote Similarity	NPD491	Approved
0.6766	Remote Similarity	NPD9582	Phase 3
0.6765	Remote Similarity	NPD2864	Phase 1
0.6763	Remote Similarity	NPD1332	Clinical (unspecified phase)
0.6763	Remote Similarity	NPD2111	Clinical (unspecified phase)
0.6761	Remote Similarity	NPD1250	Clinical (unspecified phase)
0.6759	Remote Similarity	NPD1561	Phase 2
0.6759	Remote Similarity	NPD5787	Discontinued
0.6748	Remote Similarity	NPD5300	Clinical (unspecified phase)
0.6746	Remote Similarity	NPD1037	Clinical (unspecified phase)
0.6743	Remote Similarity	NPD4902	Discontinued
0.6742	Remote Similarity	NPD6577	Clinical (unspecified phase)
0.674	Remote Similarity	NPD6468	Clinical (unspecified phase)
0.674	Remote Similarity	NPD6469	Phase 3
0.6739	Remote Similarity	NPD2364	Suspended
0.6736	Remote Similarity	NPD4811	Discontinued
0.6732	Remote Similarity	NPD198	Clinical (unspecified phase)
0.672	Remote Similarity	NPD6328	Clinical (unspecified phase)
0.671	Remote Similarity	NPD786	Approved
0.6704	Remote Similarity	NPD3403	Clinical (unspecified phase)
0.6704	Remote Similarity	NPD460	Discontinued
0.669	Remote Similarity	NPD9598	Discontinued
0.6687	Remote Similarity	NPD939	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD404	Discontinued
0.6685	Remote Similarity	NPD5462	Discontinued
0.6685	Remote Similarity	NPD6761	Discontinued
0.6667	Remote Similarity	NPD6074	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2729	Approved
0.6667	Remote Similarity	NPD2141	Approved
0.6667	Remote Similarity	NPD3943	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2728	Approved
0.6667	Remote Similarity	NPD2142	Approved
0.6667	Remote Similarity	NPD2140	Approved
0.6667	Remote Similarity	NPD2730	Approved
0.6667	Remote Similarity	NPD2008	Discontinued
0.6648	Remote Similarity	NPD7722	Suspended
0.6648	Remote Similarity	NPD6721	Phase 1
0.6648	Remote Similarity	NPD4940	Approved
0.6647	Remote Similarity	NPD1873	Clinical (unspecified phase)
0.6647	Remote Similarity	NPD1002	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD5671	Approved
0.6632	Remote Similarity	NPD7657	Approved
0.6632	Remote Similarity	NPD7656	Approved
0.6629	Remote Similarity	NPD2818	Discontinued
0.6628	Remote Similarity	NPD2315	Approved
0.6623	Remote Similarity	NPD264	Clinical (unspecified phase)
0.6608	Remote Similarity	NPD3799	Suspended
0.6607	Remote Similarity	NPD1248	Discontinued
0.6596	Remote Similarity	NPD2443	Approved
0.6596	Remote Similarity	NPD2442	Approved
0.6593	Remote Similarity	NPD1174	Phase 2
0.6592	Remote Similarity	NPD2774	Clinical (unspecified phase)
0.659	Remote Similarity	NPD1892	Phase 2
0.659	Remote Similarity	NPD1893	Phase 2
0.6584	Remote Similarity	NPD427	Approved
0.6584	Remote Similarity	NPD426	Approved
0.6584	Remote Similarity	NPD428	Approved
0.6584	Remote Similarity	NPD162	Approved
0.6582	Remote Similarity	NPD2007	Clinical (unspecified phase)
0.6579	Remote Similarity	NPD4863	Approved
0.6573	Remote Similarity	NPD5016	Approved
0.6573	Remote Similarity	NPD207	Discontinued
0.6562	Remote Similarity	NPD4568	Phase 2
0.6556	Remote Similarity	NPD6619	Phase 3
0.6556	Remote Similarity	NPD3431	Approved
0.6556	Remote Similarity	NPD3430	Approved
0.6556	Remote Similarity	NPD9305	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD3310	Approved
0.6548	Remote Similarity	NPD5269	Clinical (unspecified phase)
0.6546	Remote Similarity	NPD3521	Phase 2
0.6545	Remote Similarity	NPD2411	Approved
0.6543	Remote Similarity	NPD1506	Discontinued
0.6543	Remote Similarity	NPD971	Clinical (unspecified phase)
0.6541	Remote Similarity	NPD5254	Discontinued
0.6534	Remote Similarity	NPD2456	Phase 2
0.6534	Remote Similarity	NPD2457	Phase 2
0.6532	Remote Similarity	NPD2931	Phase 1
0.6531	Remote Similarity	NPD4414	Discontinued
0.6528	Remote Similarity	NPD9396	Approved
0.6528	Remote Similarity	NPD9392	Approved
0.6527	Remote Similarity	NPD2480	Clinical (unspecified phase)
0.6519	Remote Similarity	NPD2445	Approved
0.6519	Remote Similarity	NPD1592	Phase 3
0.6519	Remote Similarity	NPD1722	Approved
0.6519	Remote Similarity	NPD3834	Clinical (unspecified phase)
0.6519	Remote Similarity	NPD2446	Approved
0.6514	Remote Similarity	NPD2301	Approved
0.65	Remote Similarity	NPD3630	Approved
0.65	Remote Similarity	NPD1690	Clinical (unspecified phase)
0.65	Remote Similarity	NPD3629	Approved
0.6497	Remote Similarity	NPD5001	Clinical (unspecified phase)
0.6495	Remote Similarity	NPD8256	Approved
0.6495	Remote Similarity	NPD8258	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