NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	208.1
Volume:	228.569
LogP:	3.393
LogD:	3.381
LogS:	-3.876
# Rotatable Bonds:	2
TPSA:	28.68
# H-Bond Aceptor:	2
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.688
Synthetic Accessibility Score:	1.624
Fsp3:	0.071
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.822
MDCK Permeability:	3.1559822673443705e-05
Pgp-inhibitor:	0.012
Pgp-substrate:	0.04
Human Intestinal Absorption (HIA):	0.01
20% Bioavailability (F20%):	0.994
30% Bioavailability (F30%):	0.091

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.542
Plasma Protein Binding (PPB):	96.09648132324219%
Volume Distribution (VD):	1.334
Pgp-substrate:	2.9135499000549316%

ADMET: Metabolism

CYP1A2-inhibitor:	0.973
CYP1A2-substrate:	0.68
CYP2C19-inhibitor:	0.964
CYP2C19-substrate:	0.062
CYP2C9-inhibitor:	0.846
CYP2C9-substrate:	0.068
CYP2D6-inhibitor:	0.966
CYP2D6-substrate:	0.125
CYP3A4-inhibitor:	0.7
CYP3A4-substrate:	0.702

ADMET: Excretion

Clearance (CL):	5.499
Half-life (T1/2):	0.798

ADMET: Toxicity

hERG Blockers:	0.2
Human Hepatotoxicity (H-HT):	0.298
Drug-inuced Liver Injury (DILI):	0.686
AMES Toxicity:	0.348
Rat Oral Acute Toxicity:	0.45
Maximum Recommended Daily Dose:	0.881
Skin Sensitization:	0.108
Carcinogencity:	0.153
Eye Corrosion:	0.004
Eye Irritation:	0.434
Respiratory Toxicity:	0.968

Download Data

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

Natural Product: NPC114209

Natural Product ID:	NPC114209
*Common Name:**	Bendazol
IUPAC Name:	2-benzyl-1H-benzimidazole
Synonyms:	Bendazol; Dibasol; Dibazol
Standard InCHIKey:	YTLQFZVCLXFFRK-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C14H12N2/c1-2-6-11(7-3-1)10-14-15-12-8-4-5-9-13(12)16-14/h1-9H,10H2,(H,15,16)
SMILES:	c1ccc(cc1)Cc1nc2c([nH]1)cccc2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL355063
PubChem CID:	12132
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
NPO13274	Illicium verum	Species	Schisandraceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO13274	Illicium verum	Species	Schisandraceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO13274	Illicium verum	Species	Schisandraceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO13274	Illicium verum	Species	Schisandraceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO13274	Illicium verum	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13274	Illicium verum	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13274	Illicium verum	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO13274	Illicium verum	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO13274	Illicium verum	Species	Schisandraceae	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	2
Others	2
Potency	5

Activity Type	# Activity
Cell Line	1
Individual Protein	4
Organism	1
Others	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1775	Individual Protein	Cytochrome P450 2B1	Rattus norvegicus	IC50	=	91201.08	nM	PMID[504539]
NPT56	Individual Protein	Beta-lactamase AmpC	Escherichia coli K-12	Potency	=	39810.7	nM	PMID[504540]
NPT60	Individual Protein	Lysosomal alpha-glucosidase	Homo sapiens	Potency	=	50118.7	nM	PMID[504540]
NPT65	Cell Line	HepG2	Homo sapiens	Potency	n.a.	35481.3	nM	PMID[504540]
NPT10	Individual Protein	Geminin	Homo sapiens	Potency	n.a.	4466.8	nM	PMID[504540]
NPT35	Others	n.a.		LogP	=	3.46	n.a.	PMID[504539]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Potency	n.a.	1651.1	nM	PMID[504540]
NPT2	Others	Unspecified		Inhibition	=	43.0	%	PMID[504541]
NPT2	Others	Unspecified		IC50	=	18400.0	nM	PMID[504541]

☑ 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 NPC114209 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	2573
0.1-0.2	15220
0.2-0.3	17115
0.3-0.4	3617
0.4-0.5	2101
0.5-0.6	1601
0.6-0.7	382
0.7-0.8	80
0.8-0.85	5
0.85-0.9	1
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9137	High Similarity	NPC216159
0.8562	High Similarity	NPC300238
0.8378	Intermediate Similarity	NPC42483
0.7908	Intermediate Similarity	NPC204141
0.7881	Intermediate Similarity	NPC284635
0.7847	Intermediate Similarity	NPC250361
0.7818	Intermediate Similarity	NPC317054
0.7812	Intermediate Similarity	NPC470204
0.78	Intermediate Similarity	NPC125746
0.7764	Intermediate Similarity	NPC470203
0.7763	Intermediate Similarity	NPC115611
0.774	Intermediate Similarity	NPC473762
0.7692	Intermediate Similarity	NPC41174
0.7687	Intermediate Similarity	NPC473587
0.7635	Intermediate Similarity	NPC475428
0.7593	Intermediate Similarity	NPC122141
0.7584	Intermediate Similarity	NPC475450
0.7584	Intermediate Similarity	NPC179365
0.755	Intermediate Similarity	NPC198988
0.7533	Intermediate Similarity	NPC473930
0.7532	Intermediate Similarity	NPC282531
0.7517	Intermediate Similarity	NPC22079
0.7516	Intermediate Similarity	NPC63545
0.75	Intermediate Similarity	NPC325252
0.7468	Intermediate Similarity	NPC469811
0.7468	Intermediate Similarity	NPC201380
0.7468	Intermediate Similarity	NPC179787
0.7459	Intermediate Similarity	NPC469308
0.7453	Intermediate Similarity	NPC476297
0.7453	Intermediate Similarity	NPC476219
0.7421	Intermediate Similarity	NPC321911
0.7405	Intermediate Similarity	NPC143872
0.7391	Intermediate Similarity	NPC325903
0.7386	Intermediate Similarity	NPC218268
0.7355	Intermediate Similarity	NPC88097
0.7337	Intermediate Similarity	NPC314557
0.7289	Intermediate Similarity	NPC247987
0.7254	Intermediate Similarity	NPC143156
0.7251	Intermediate Similarity	NPC315715
0.7244	Intermediate Similarity	NPC312092
0.7184	Intermediate Similarity	NPC307191
0.7178	Intermediate Similarity	NPC232798
0.7161	Intermediate Similarity	NPC96102
0.7159	Intermediate Similarity	NPC476341
0.7152	Intermediate Similarity	NPC236711
0.7126	Intermediate Similarity	NPC225018
0.7125	Intermediate Similarity	NPC470440
0.7124	Intermediate Similarity	NPC82295
0.7115	Intermediate Similarity	NPC105127
0.7115	Intermediate Similarity	NPC84911
0.7089	Intermediate Similarity	NPC59084
0.7089	Intermediate Similarity	NPC2949
0.7083	Intermediate Similarity	NPC317105
0.7081	Intermediate Similarity	NPC288838
0.7068	Intermediate Similarity	NPC471603
0.7055	Intermediate Similarity	NPC54102
0.7055	Intermediate Similarity	NPC162689
0.7051	Intermediate Similarity	NPC29886
0.7051	Intermediate Similarity	NPC261195
0.7044	Intermediate Similarity	NPC63157
0.7044	Intermediate Similarity	NPC473868
0.7037	Intermediate Similarity	NPC116555
0.703	Intermediate Similarity	NPC120070
0.7025	Intermediate Similarity	NPC110126
0.7025	Intermediate Similarity	NPC73767
0.702	Intermediate Similarity	NPC75999
0.701	Intermediate Similarity	NPC267811
0.6993	Remote Similarity	NPC314141
0.6981	Remote Similarity	NPC469784
0.6981	Remote Similarity	NPC279081
0.6981	Remote Similarity	NPC469761
0.6981	Remote Similarity	NPC469767
0.6981	Remote Similarity	NPC469768
0.6981	Remote Similarity	NPC469779
0.6981	Remote Similarity	NPC469783
0.6981	Remote Similarity	NPC469780
0.6957	Remote Similarity	NPC242556
0.6951	Remote Similarity	NPC53947
0.6949	Remote Similarity	NPC471609
0.6941	Remote Similarity	NPC274229
0.6937	Remote Similarity	NPC469766
0.6936	Remote Similarity	NPC208060
0.6933	Remote Similarity	NPC477134
0.6932	Remote Similarity	NPC88110
0.6918	Remote Similarity	NPC148140
0.6914	Remote Similarity	NPC240088
0.6914	Remote Similarity	NPC473380
0.6905	Remote Similarity	NPC221786
0.6905	Remote Similarity	NPC474880
0.6905	Remote Similarity	NPC475990
0.6901	Remote Similarity	NPC49217
0.6894	Remote Similarity	NPC190296
0.6875	Remote Similarity	NPC230002
0.6875	Remote Similarity	NPC265710
0.6871	Remote Similarity	NPC81561
0.6864	Remote Similarity	NPC229173
0.6848	Remote Similarity	NPC33421
0.6842	Remote Similarity	NPC280864
0.6842	Remote Similarity	NPC17751
0.6836	Remote Similarity	NPC16659
0.6829	Remote Similarity	NPC21605
0.6824	Remote Similarity	NPC253687
0.6821	Remote Similarity	NPC97343
0.6816	Remote Similarity	NPC21429
0.6816	Remote Similarity	NPC108011
0.681	Remote Similarity	NPC159856
0.681	Remote Similarity	NPC314372
0.6807	Remote Similarity	NPC470233
0.6798	Remote Similarity	NPC477891
0.6788	Remote Similarity	NPC124005
0.6788	Remote Similarity	NPC37548
0.6788	Remote Similarity	NPC288445
0.6782	Remote Similarity	NPC82331
0.6782	Remote Similarity	NPC187145
0.6781	Remote Similarity	NPC317031
0.6776	Remote Similarity	NPC122718
0.6769	Remote Similarity	NPC282247
0.6768	Remote Similarity	NPC478186
0.6763	Remote Similarity	NPC278874
0.6761	Remote Similarity	NPC280852
0.6747	Remote Similarity	NPC148592
0.6746	Remote Similarity	NPC216643
0.6746	Remote Similarity	NPC299594
0.6743	Remote Similarity	NPC252572
0.6733	Remote Similarity	NPC215519
0.6728	Remote Similarity	NPC88121
0.6727	Remote Similarity	NPC470111
0.6727	Remote Similarity	NPC471957
0.6707	Remote Similarity	NPC469975
0.6706	Remote Similarity	NPC135141
0.6706	Remote Similarity	NPC92796
0.6704	Remote Similarity	NPC144114
0.6687	Remote Similarity	NPC2272
0.6686	Remote Similarity	NPC476688
0.6686	Remote Similarity	NPC476686
0.6686	Remote Similarity	NPC105758
0.6684	Remote Similarity	NPC71238
0.6667	Remote Similarity	NPC44773
0.6667	Remote Similarity	NPC151635
0.6667	Remote Similarity	NPC474958
0.6667	Remote Similarity	NPC215584
0.6648	Remote Similarity	NPC17273
0.6648	Remote Similarity	NPC135601
0.6648	Remote Similarity	NPC141612
0.6647	Remote Similarity	NPC24678
0.6647	Remote Similarity	NPC76982
0.6647	Remote Similarity	NPC286427
0.6647	Remote Similarity	NPC105818
0.6629	Remote Similarity	NPC474897
0.6627	Remote Similarity	NPC471458
0.6627	Remote Similarity	NPC470507
0.6627	Remote Similarity	NPC38736
0.6608	Remote Similarity	NPC56765
0.6608	Remote Similarity	NPC206819
0.6608	Remote Similarity	NPC41257
0.6608	Remote Similarity	NPC474791
0.6608	Remote Similarity	NPC318065
0.6607	Remote Similarity	NPC216713
0.6607	Remote Similarity	NPC470823
0.6594	Remote Similarity	NPC317642
0.659	Remote Similarity	NPC8104
0.659	Remote Similarity	NPC21174
0.659	Remote Similarity	NPC271734
0.659	Remote Similarity	NPC271797
0.6588	Remote Similarity	NPC141353
0.6588	Remote Similarity	NPC184476
0.6588	Remote Similarity	NPC285469
0.6587	Remote Similarity	NPC187951
0.6582	Remote Similarity	NPC54981
0.6582	Remote Similarity	NPC101165
0.657	Remote Similarity	NPC935
0.657	Remote Similarity	NPC267078
0.6568	Remote Similarity	NPC141926
0.6568	Remote Similarity	NPC25008
0.6568	Remote Similarity	NPC73952
0.6568	Remote Similarity	NPC200214
0.6568	Remote Similarity	NPC259644
0.6568	Remote Similarity	NPC469786
0.6568	Remote Similarity	NPC469765
0.6568	Remote Similarity	NPC469763
0.6568	Remote Similarity	NPC469760
0.6566	Remote Similarity	NPC316069
0.6566	Remote Similarity	NPC129042
0.6558	Remote Similarity	NPC27740
0.6552	Remote Similarity	NPC195507
0.6552	Remote Similarity	NPC2165
0.6538	Remote Similarity	NPC474357
0.6532	Remote Similarity	NPC224632
0.6529	Remote Similarity	NPC80597
0.6529	Remote Similarity	NPC211572
0.6529	Remote Similarity	NPC70922
0.6529	Remote Similarity	NPC34844
0.6529	Remote Similarity	NPC75540
0.6529	Remote Similarity	NPC212376
0.6522	Remote Similarity	NPC470323
0.6519	Remote Similarity	NPC314394
0.6519	Remote Similarity	NPC191415
0.6517	Remote Similarity	NPC280297
0.6494	Remote Similarity	NPC478184
0.6494	Remote Similarity	NPC46358

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 NPC114209 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	652
0.1-0.2	967
0.2-0.3	1231
0.3-0.4	2278
0.4-0.5	2085
0.5-0.6	1356
0.6-0.7	464
0.7-0.8	102
0.8-0.85	14
0.85-0.9	0
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9013	High Similarity	NPD2392	Clinical (unspecified phase)
0.8675	High Similarity	NPD2927	Phase 3
0.8571	High Similarity	NPD4649	Clinical (unspecified phase)
0.8405	Intermediate Similarity	NPD4441	Phase 2
0.8378	Intermediate Similarity	NPD9724	Phase 1
0.8365	Intermediate Similarity	NPD1567	Clinical (unspecified phase)
0.8364	Intermediate Similarity	NPD2793	Discontinued
0.8282	Intermediate Similarity	NPD5962	Phase 2
0.8228	Intermediate Similarity	NPD509	Phase 3
0.8182	Intermediate Similarity	NPD3512	Clinical (unspecified phase)
0.8171	Intermediate Similarity	NPD702	Clinical (unspecified phase)
0.8121	Intermediate Similarity	NPD1895	Discontinued
0.8113	Intermediate Similarity	NPD1313	Approved
0.811	Intermediate Similarity	NPD40	Phase 2
0.811	Intermediate Similarity	NPD5730	Phase 2
0.8063	Intermediate Similarity	NPD3361	Phase 1
0.8063	Intermediate Similarity	NPD2478	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD2930	Clinical (unspecified phase)
0.7975	Intermediate Similarity	NPD5996	Clinical (unspecified phase)
0.7953	Intermediate Similarity	NPD3419	Clinical (unspecified phase)
0.795	Intermediate Similarity	NPD6794	Approved
0.7919	Intermediate Similarity	NPD1262	Discovery
0.7914	Intermediate Similarity	NPD6827	Clinical (unspecified phase)
0.7914	Intermediate Similarity	NPD6828	Phase 2
0.7888	Intermediate Similarity	NPD3889	Approved
0.7879	Intermediate Similarity	NPD5943	Clinical (unspecified phase)
0.7853	Intermediate Similarity	NPD2875	Clinical (unspecified phase)
0.7849	Intermediate Similarity	NPD7709	Discontinued
0.784	Intermediate Similarity	NPD1215	Discontinued
0.7803	Intermediate Similarity	NPD1896	Approved
0.7791	Intermediate Similarity	NPD1043	Phase 3
0.7791	Intermediate Similarity	NPD2333	Discontinued
0.7771	Intermediate Similarity	NPD2524	Discontinued
0.7771	Intermediate Similarity	NPD2316	Clinical (unspecified phase)
0.7753	Intermediate Similarity	NPD6145	Phase 1
0.773	Intermediate Similarity	NPD4213	Clinical (unspecified phase)
0.7711	Intermediate Similarity	NPD7006	Approved
0.7697	Intermediate Similarity	NPD680	Discontinued
0.7679	Intermediate Similarity	NPD3341	Clinical (unspecified phase)
0.7679	Intermediate Similarity	NPD676	Discontinued
0.767	Intermediate Similarity	NPD1871	Approved
0.7669	Intermediate Similarity	NPD1333	Phase 3
0.7654	Intermediate Similarity	NPD1016	Phase 2
0.7654	Intermediate Similarity	NPD1015	Phase 2
0.7654	Intermediate Similarity	NPD2149	Clinical (unspecified phase)
0.763	Intermediate Similarity	NPD7884	Discontinued
0.7616	Intermediate Similarity	NPD2591	Phase 2
0.7605	Intermediate Similarity	NPD1569	Phase 2
0.7595	Intermediate Similarity	NPD1027	Approved
0.7595	Intermediate Similarity	NPD1030	Approved
0.7595	Intermediate Similarity	NPD1029	Clinical (unspecified phase)
0.7557	Intermediate Similarity	NPD6265	Discontinued
0.75	Intermediate Similarity	NPD5463	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD3347	Clinical (unspecified phase)
0.7471	Intermediate Similarity	NPD2009	Clinical (unspecified phase)
0.7471	Intermediate Similarity	NPD1327	Discontinued
0.747	Intermediate Similarity	NPD773	Approved
0.7459	Intermediate Similarity	NPD4318	Clinical (unspecified phase)
0.7438	Intermediate Similarity	NPD2128	Phase 1
0.743	Intermediate Similarity	NPD2880	Discontinued
0.7414	Intermediate Similarity	NPD3378	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD1303	Phase 1
0.7391	Intermediate Similarity	NPD695	Discontinued
0.7384	Intermediate Similarity	NPD412	Approved
0.7355	Intermediate Similarity	NPD174	Discontinued
0.7348	Intermediate Similarity	NPD6264	Discontinued
0.734	Intermediate Similarity	NPD2794	Discontinued
0.7337	Intermediate Similarity	NPD966	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD1257	Approved
0.7317	Intermediate Similarity	NPD1042	Clinical (unspecified phase)
0.7314	Intermediate Similarity	NPD4902	Discontinued
0.7314	Intermediate Similarity	NPD6721	Phase 1
0.7314	Intermediate Similarity	NPD4940	Approved
0.7308	Intermediate Similarity	NPD3943	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD6816	Phase 3
0.7303	Intermediate Similarity	NPD6577	Clinical (unspecified phase)
0.7302	Intermediate Similarity	NPD7276	Approved
0.7302	Intermediate Similarity	NPD7277	Approved
0.7301	Intermediate Similarity	NPD2150	Discontinued
0.7301	Intermediate Similarity	NPD1290	Phase 2
0.7297	Intermediate Similarity	NPD6403	Clinical (unspecified phase)
0.7293	Intermediate Similarity	NPD6469	Phase 3
0.7293	Intermediate Similarity	NPD6468	Clinical (unspecified phase)
0.7289	Intermediate Similarity	NPD404	Discontinued
0.7263	Intermediate Similarity	NPD3485	Clinical (unspecified phase)
0.7258	Intermediate Similarity	NPD6328	Clinical (unspecified phase)
0.7251	Intermediate Similarity	NPD2406	Clinical (unspecified phase)
0.7247	Intermediate Similarity	NPD6761	Discontinued
0.7239	Intermediate Similarity	NPD3405	Phase 3
0.7232	Intermediate Similarity	NPD2728	Approved
0.7232	Intermediate Similarity	NPD2729	Approved
0.7232	Intermediate Similarity	NPD5016	Approved
0.7232	Intermediate Similarity	NPD2730	Approved
0.7225	Intermediate Similarity	NPD1873	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD2660	Approved
0.7222	Intermediate Similarity	NPD2662	Approved
0.7215	Intermediate Similarity	NPD4047	Discontinued
0.7209	Intermediate Similarity	NPD1272	Clinical (unspecified phase)
0.7209	Intermediate Similarity	NPD2315	Approved
0.7209	Intermediate Similarity	NPD2731	Phase 2
0.7207	Intermediate Similarity	NPD7722	Suspended
0.7193	Intermediate Similarity	NPD3799	Suspended
0.7189	Intermediate Similarity	NPD2364	Suspended
0.7184	Intermediate Similarity	NPD1707	Approved
0.7184	Intermediate Similarity	NPD1708	Approved
0.717	Intermediate Similarity	NPD5254	Discontinued
0.7167	Intermediate Similarity	NPD3403	Clinical (unspecified phase)
0.7161	Intermediate Similarity	NPD198	Clinical (unspecified phase)
0.7159	Intermediate Similarity	NPD2868	Clinical (unspecified phase)
0.7158	Intermediate Similarity	NPD7657	Approved
0.7158	Intermediate Similarity	NPD7656	Approved
0.7152	Intermediate Similarity	NPD5300	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD2774	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD2892	Phase 1
0.7143	Intermediate Similarity	NPD1002	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD5462	Discontinued
0.7143	Intermediate Similarity	NPD1332	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD3310	Approved
0.7107	Intermediate Similarity	NPD9254	Phase 3
0.7107	Intermediate Similarity	NPD4637	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD2007	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD1561	Phase 2
0.7095	Intermediate Similarity	NPD2818	Discontinued
0.7091	Intermediate Similarity	NPD939	Clinical (unspecified phase)
0.7088	Intermediate Similarity	NPD6278	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD2301	Approved
0.7076	Intermediate Similarity	NPD3418	Clinical (unspecified phase)
0.7069	Intermediate Similarity	NPD1892	Phase 2
0.7069	Intermediate Similarity	NPD1893	Phase 2
0.7068	Intermediate Similarity	NPD2411	Approved
0.7066	Intermediate Similarity	NPD6074	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD5671	Approved
0.7044	Intermediate Similarity	NPD1722	Approved
0.7037	Intermediate Similarity	NPD2443	Approved
0.7037	Intermediate Similarity	NPD2442	Approved
0.7025	Intermediate Similarity	NPD786	Approved
0.7021	Intermediate Similarity	NPD2008	Discontinued
0.7017	Intermediate Similarity	NPD3430	Approved
0.7017	Intermediate Similarity	NPD3431	Approved
0.7016	Intermediate Similarity	NPD4863	Approved
0.701	Intermediate Similarity	NPD8257	Approved
0.701	Intermediate Similarity	NPD8258	Clinical (unspecified phase)
0.701	Intermediate Similarity	NPD8256	Approved
0.7006	Intermediate Similarity	NPD1860	Approved
0.7006	Intermediate Similarity	NPD544	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6545	Clinical (unspecified phase)
0.6995	Remote Similarity	NPD7023	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD4374	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD947	Approved
0.6987	Remote Similarity	NPD2140	Approved
0.6987	Remote Similarity	NPD2141	Approved
0.6987	Remote Similarity	NPD2142	Approved
0.6987	Remote Similarity	NPD4880	Discontinued
0.6984	Remote Similarity	NPD1506	Discontinued
0.6984	Remote Similarity	NPD8410	Clinical (unspecified phase)
0.6983	Remote Similarity	NPD3002	Clinical (unspecified phase)
0.6979	Remote Similarity	NPD8458	Clinical (unspecified phase)
0.6978	Remote Similarity	NPD460	Discontinued
0.6978	Remote Similarity	NPD2445	Approved
0.6978	Remote Similarity	NPD2446	Approved
0.6975	Remote Similarity	NPD1683	Approved
0.6975	Remote Similarity	NPD1528	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD3521	Phase 2
0.6964	Remote Similarity	NPD1288	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD4414	Discontinued
0.6951	Remote Similarity	NPD4463	Approved
0.6951	Remote Similarity	NPD4462	Approved
0.6949	Remote Similarity	NPD2111	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD1869	Phase 2
0.6943	Remote Similarity	NPD8488	Clinical (unspecified phase)
0.694	Remote Similarity	NPD4294	Phase 2
0.6935	Remote Similarity	NPD4403	Phase 3
0.6935	Remote Similarity	NPD4401	Phase 2
0.6932	Remote Similarity	NPD5508	Phase 1
0.6923	Remote Similarity	NPD6619	Phase 3
0.6923	Remote Similarity	NPD418	Approved
0.6923	Remote Similarity	NPD2480	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD5001	Clinical (unspecified phase)
0.691	Remote Similarity	NPD1887	Clinical (unspecified phase)
0.6902	Remote Similarity	NPD3362	Clinical (unspecified phase)
0.6902	Remote Similarity	NPD2960	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD1248	Discontinued
0.6897	Remote Similarity	NPD4128	Approved
0.6895	Remote Similarity	NPD7445	Phase 1
0.6894	Remote Similarity	NPD4864	Approved
0.6893	Remote Similarity	NPD5806	Clinical (unspecified phase)
0.6878	Remote Similarity	NPD7103	Approved
0.6878	Remote Similarity	NPD5012	Phase 2
0.6875	Remote Similarity	NPD1167	Phase 3
0.6872	Remote Similarity	NPD4298	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD4568	Phase 2
0.686	Remote Similarity	NPD4320	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD5843	Discontinued
0.6852	Remote Similarity	NPD1918	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD4849	Approved
0.6842	Remote Similarity	NPD6271	Approved
0.6842	Remote Similarity	NPD4023	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD5269	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD3224	Phase 2
0.6833	Remote Similarity	NPD2963	Phase 1

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