NPASS Compound

Structure

NPC470233 OpenBabel07101718282D 25 28 0 0 0 0 0 0 0 0999 V2000 4.3776 1.5933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2514 -1.4476 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0704 0.2749 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2460 -1.3431 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0649 0.3795 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0119 -3.3317 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5704 -2.6272 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7796 1.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6456 -0.4067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3948 -4.2453 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9771 -3.5408 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6456 1.5933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5116 0.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8090 -1.4013 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5759 -2.5227 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7796 0.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6637 -0.6386 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6527 -0.4296 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1691 -1.6092 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9135 -0.4067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6691 -0.7431 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6472 -0.3250 0.0000 F 0 0 0 0 0 0 0 0 0 0 0 0 -1.3893 -4.3498 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 3.5116 1.0933 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1 25 1 0 0 0 0 2 4 1 0 0 0 0 2 17 2 0 0 0 0 3 5 2 0 0 0 0 3 17 1 0 0 0 0 4 18 2 0 0 0 0 5 18 1 0 0 0 0 6 10 1 0 0 0 0 6 15 2 0 0 0 0 7 11 2 0 0 0 0 7 15 1 0 0 0 0 8 12 1 0 0 0 0 8 16 1 0 0 0 0 9 13 1 0 0 0 0 9 16 1 0 0 0 0 10 23 2 0 0 0 0 11 23 1 0 0 0 0 12 25 1 0 0 0 0 13 25 1 0 0 0 0 14 19 1 0 0 0 0 14 20 2 0 0 0 0 15 19 1 0 0 0 0 16 20 1 0 0 0 0 17 21 1 0 0 0 0 18 22 1 0 0 0 0 19 21 2 0 0 0 0 20 24 1 0 0 0 0 21 24 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	335.18
Volume:	355.512
LogP:	4.049
LogD:	3.484
LogS:	-3.021
# Rotatable Bonds:	3
TPSA:	31.92
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.753
Synthetic Accessibility Score:	2.406
Fsp3:	0.286
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.799
MDCK Permeability:	1.389020872011315e-05
Pgp-inhibitor:	0.956
Pgp-substrate:	0.991
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.002

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.983
Plasma Protein Binding (PPB):	77.36504364013672%
Volume Distribution (VD):	2.853
Pgp-substrate:	17.404590606689453%

ADMET: Metabolism

CYP1A2-inhibitor:	0.917
CYP1A2-substrate:	0.929
CYP2C19-inhibitor:	0.646
CYP2C19-substrate:	0.615
CYP2C9-inhibitor:	0.511
CYP2C9-substrate:	0.467
CYP2D6-inhibitor:	0.973
CYP2D6-substrate:	0.923
CYP3A4-inhibitor:	0.953
CYP3A4-substrate:	0.538

ADMET: Excretion

Clearance (CL):	8.612
Half-life (T1/2):	0.079

ADMET: Toxicity

hERG Blockers:	0.975
Human Hepatotoxicity (H-HT):	0.376
Drug-inuced Liver Injury (DILI):	0.688
AMES Toxicity:	0.164
Rat Oral Acute Toxicity:	0.868
Maximum Recommended Daily Dose:	0.933
Skin Sensitization:	0.639
Carcinogencity:	0.045
Eye Corrosion:	0.003
Eye Irritation:	0.011
Respiratory Toxicity:	0.975

Download Data

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

Natural Product: NPC470233

Natural Product ID:	NPC470233
*Common Name:**
IUPAC Name:	4-[2-(4-fluorophenyl)-5-(1-methylpiperidin-4-yl)-1H-pyrrol-3-yl]pyridine
Synonyms:
Standard InCHIKey:	RBWNFHXBUDPAIO-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C21H22FN3/c1-25-12-8-16(9-13-25)20-14-19(15-6-10-23-11-7-15)21(24-20)17-2-4-18(22)5-3-17/h2-7,10-11,14,16,24H,8-9,12-13H2,1H3
SMILES:	CN1CCC(CC1)c1[nH]c(c(c1)c1ccncc1)c1ccc(cc1)F
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL190228
PubChem CID:	500899
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000090] Pyrroles [CHEMONTID:0002257] Substituted pyrroles [CHEMONTID:0002334] Phenylpyrroles

*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
NPO33124	Diaporthe	Genus	Diaporthaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15844962]
NPO32661	Phoma sp.	Species	Didymellaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16562839]
NPO32661	Phoma sp.	Species	Didymellaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16643061]
NPO32661	Phoma sp.	Species	Didymellaceae	Eukaryota	giant jellyfish Nemopilema nomurai	n.a.	n.a.	PMID[22483395]
NPO32661	Phoma sp.	Species	Didymellaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26651221]
NPO32661	Phoma sp.	Species	Didymellaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[30785282]
NPO32661	Phoma sp.	Species	Didymellaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31120749]
NPO32661	Phoma sp.	Species	Didymellaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7561907]

☑ 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	1
IC50	12
Others	24

Activity Type	# Activity
Individual Protein	4
NON-MOLECULAR	1
Organism	29
Others	2
SINGLE PROTEIN	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT6488	Individual Protein	cGMP-dependent protein kinase	Eimeria tenella	IC50	=	0.7	nM	PMID[548233]
NPT6488	Individual Protein	cGMP-dependent protein kinase	Eimeria tenella	IC50	<	1.0	nM	PMID[548234]
NPT6433	Individual Protein	CGMP-dependent protein kinase	Plasmodium falciparum	IC50	=	8.0	nM	PMID[548237]
NPT6433	Individual Protein	CGMP-dependent protein kinase	Plasmodium falciparum	IC50	=	6.0	nM	PMID[548242]
NPT3129	Organism	Eimeria tenella	Eimeria tenella	Activity	>=	80.0	%	PMID[548233]
NPT3128	Organism	Eimeria acervulina	Eimeria acervulina	Activity	>=	80.0	%	PMID[548233]
NPT486	Organism	Toxoplasma gondii	Toxoplasma gondii	IC50	=	210000.0	nM	PMID[548234]
NPT2	Others	Unspecified		IC50	<	1.0	nM	PMID[548235]
NPT486	Organism	Toxoplasma gondii	Toxoplasma gondii	IC50	=	210.0	nM	PMID[548235]
NPT474	Organism	Plasmodium berghei	Plasmodium berghei	INH	>	1.0	uM	PMID[548236]
NPT474	Organism	Plasmodium berghei	Plasmodium berghei	Activity	=	50.0	%	PMID[548236]
NPT474	Organism	Plasmodium berghei	Plasmodium berghei	FC	>	1000.0	n.a.	PMID[548236]
NPT475	Organism	Plasmodium yoelii	Plasmodium yoelii	FC	>	1000.0	n.a.	PMID[548236]
NPT475	Organism	Plasmodium yoelii	Plasmodium yoelii	TIME	=	127.92	hr	PMID[548236]
NPT474	Organism	Plasmodium berghei	Plasmodium berghei	Inhibition	>	90.0	%	PMID[548238]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	CC50	>	50000.0	nM	PMID[548239]
NPT486	Organism	Toxoplasma gondii	Toxoplasma gondii	Inhibition	=	100.0	%	PMID[548239]
NPT486	Organism	Toxoplasma gondii	Toxoplasma gondii	Inhibition	=	99.3	%	PMID[548239]
NPT486	Organism	Toxoplasma gondii	Toxoplasma gondii	Inhibition	=	100.0	uM	PMID[548239]
NPT486	Organism	Toxoplasma gondii	Toxoplasma gondii	Inhibition	=	97.86	uM	PMID[548239]
NPT486	Organism	Toxoplasma gondii	Toxoplasma gondii	IC50	=	1210.0	nM	PMID[548239]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	1300.0	nM	PMID[548241]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	490.0	nM	PMID[548241]
NPT2	Others	Unspecified		IC50	=	3.5	nM	PMID[548241]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	EC50	=	450.0	nM	PMID[548242]
NPT20556	SINGLE PROTEIN	Replicase polyprotein 1ab	Severe acute respiratory syndrome coronavirus 2	Inhibition	=	9.51	%	PMID[548243]
NPT20555	ORGANISM	SARS-CoV-2	Severe acute respiratory syndrome coronavirus 2	Inhibition	=	0.11	%	PMID[548244]
NPT22194	ORGANISM	Naegleria gruberi	Naegleria gruberi	Inhibition	n.a.	0.0	%	PMID[548245]
NPT20	Organism	Candida albicans	Candida albicans	Inhibition	=	0.45	%	PMID[548246]
NPT85	Organism	Filobasidiella neoformans	Cryptococcus neoformans	Inhibition	=	8.69	%	PMID[548246]
NPT19	Organism	Escherichia coli	Escherichia coli	Inhibition	=	-2.15	%	PMID[548246]
NPT173	Organism	Klebsiella pneumoniae	Klebsiella pneumoniae	Inhibition	=	5.43	%	PMID[548246]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	Inhibition	=	4.09	%	PMID[548246]
NPT747	Organism	Acinetobacter baumannii	Acinetobacter baumannii	Inhibition	=	12.09	%	PMID[548246]
NPT2922	Organism	Staphylococcus aureus subsp. aureus	Staphylococcus aureus subsp. aureus	Inhibition	=	-0.65	%	PMID[548246]

☑ 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 NPC470233 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	951
0.1-0.2	9789
0.2-0.3	20853
0.3-0.4	5682
0.4-0.5	2110
0.5-0.6	1859
0.6-0.7	1051
0.7-0.8	332
0.8-0.85	65
0.85-0.9	4
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8889	High Similarity	NPC73767
0.8859	High Similarity	NPC53947
0.8851	High Similarity	NPC201380
0.8851	High Similarity	NPC179787
0.8828	High Similarity	NPC469768
0.8828	High Similarity	NPC469779
0.8828	High Similarity	NPC469767
0.8828	High Similarity	NPC469780
0.8828	High Similarity	NPC469784
0.8828	High Similarity	NPC469761
0.8828	High Similarity	NPC469783
0.8792	High Similarity	NPC321911
0.8784	High Similarity	NPC63545
0.8767	High Similarity	NPC469766
0.8759	High Similarity	NPC110126
0.8758	High Similarity	NPC56765
0.875	High Similarity	NPC84911
0.8742	High Similarity	NPC325903
0.8725	High Similarity	NPC469811
0.8681	High Similarity	NPC29886
0.8681	High Similarity	NPC96102
0.8681	High Similarity	NPC261195
0.8658	High Similarity	NPC288838
0.863	High Similarity	NPC88097
0.8625	High Similarity	NPC280852
0.8621	High Similarity	NPC105127
0.8609	High Similarity	NPC40070
0.86	High Similarity	NPC21605
0.8581	High Similarity	NPC215584
0.8581	High Similarity	NPC44773
0.8571	High Similarity	NPC216643
0.8571	High Similarity	NPC59084
0.8516	High Similarity	NPC206819
0.8516	High Similarity	NPC318065
0.8514	High Similarity	NPC63157
0.8514	High Similarity	NPC473868
0.8493	Intermediate Similarity	NPC251722
0.8493	Intermediate Similarity	NPC314102
0.8483	Intermediate Similarity	NPC198988
0.8471	Intermediate Similarity	NPC90723
0.8467	Intermediate Similarity	NPC314372
0.8456	Intermediate Similarity	NPC190296
0.8452	Intermediate Similarity	NPC286427
0.8452	Intermediate Similarity	NPC236711
0.8446	Intermediate Similarity	NPC279081
0.8446	Intermediate Similarity	NPC2949
0.8408	Intermediate Similarity	NPC470203
0.8403	Intermediate Similarity	NPC82295
0.8397	Intermediate Similarity	NPC41257
0.8366	Intermediate Similarity	NPC105818
0.8366	Intermediate Similarity	NPC24678
0.8354	Intermediate Similarity	NPC317105
0.8344	Intermediate Similarity	NPC470204
0.8344	Intermediate Similarity	NPC122141
0.8344	Intermediate Similarity	NPC229173
0.8322	Intermediate Similarity	NPC230002
0.8299	Intermediate Similarity	NPC325252
0.8289	Intermediate Similarity	NPC143872
0.828	Intermediate Similarity	NPC474880
0.828	Intermediate Similarity	NPC475990
0.828	Intermediate Similarity	NPC221786
0.828	Intermediate Similarity	NPC92796
0.828	Intermediate Similarity	NPC135141
0.8258	Intermediate Similarity	NPC469765
0.8258	Intermediate Similarity	NPC259644
0.8258	Intermediate Similarity	NPC73952
0.8258	Intermediate Similarity	NPC25008
0.8258	Intermediate Similarity	NPC200214
0.8258	Intermediate Similarity	NPC469760
0.8258	Intermediate Similarity	NPC469763
0.8258	Intermediate Similarity	NPC469786
0.8247	Intermediate Similarity	NPC33421
0.8243	Intermediate Similarity	NPC150259
0.8235	Intermediate Similarity	NPC470111
0.8235	Intermediate Similarity	NPC471957
0.8224	Intermediate Similarity	NPC159856
0.821	Intermediate Similarity	NPC82331
0.8207	Intermediate Similarity	NPC22079
0.8205	Intermediate Similarity	NPC211572
0.8205	Intermediate Similarity	NPC476219
0.8205	Intermediate Similarity	NPC70922
0.8205	Intermediate Similarity	NPC80597
0.8205	Intermediate Similarity	NPC212376
0.8205	Intermediate Similarity	NPC75540
0.82	Intermediate Similarity	NPC115611
0.8171	Intermediate Similarity	NPC474958
0.8151	Intermediate Similarity	NPC475450
0.8148	Intermediate Similarity	NPC194411
0.8105	Intermediate Similarity	NPC86288
0.8092	Intermediate Similarity	NPC20144
0.8089	Intermediate Similarity	NPC34844
0.8082	Intermediate Similarity	NPC475428
0.8077	Intermediate Similarity	NPC470823
0.8075	Intermediate Similarity	NPC274229
0.8056	Intermediate Similarity	NPC250361
0.8038	Intermediate Similarity	NPC469785
0.8037	Intermediate Similarity	NPC474897
0.8025	Intermediate Similarity	NPC141926
0.8025	Intermediate Similarity	NPC474561
0.8025	Intermediate Similarity	NPC49954
0.8014	Intermediate Similarity	NPC473587
0.8012	Intermediate Similarity	NPC271797
0.8012	Intermediate Similarity	NPC21174
0.8	Intermediate Similarity	NPC275305
0.8	Intermediate Similarity	NPC37423
0.7987	Intermediate Similarity	NPC469762
0.7987	Intermediate Similarity	NPC470440
0.7986	Intermediate Similarity	NPC146373
0.7986	Intermediate Similarity	NPC245244
0.7986	Intermediate Similarity	NPC166424
0.7975	Intermediate Similarity	NPC63751
0.7973	Intermediate Similarity	NPC473930
0.7972	Intermediate Similarity	NPC46358
0.7965	Intermediate Similarity	NPC231536
0.7962	Intermediate Similarity	NPC216713
0.7959	Intermediate Similarity	NPC69914
0.7959	Intermediate Similarity	NPC282398
0.7945	Intermediate Similarity	NPC473762
0.7939	Intermediate Similarity	NPC477611
0.7933	Intermediate Similarity	NPC218268
0.7927	Intermediate Similarity	NPC97343
0.7917	Intermediate Similarity	NPC476322
0.7917	Intermediate Similarity	NPC27740
0.7914	Intermediate Similarity	NPC160105
0.7905	Intermediate Similarity	NPC179365
0.7904	Intermediate Similarity	NPC68354
0.7902	Intermediate Similarity	NPC41174
0.7901	Intermediate Similarity	NPC478182
0.7901	Intermediate Similarity	NPC311276
0.7895	Intermediate Similarity	NPC316811
0.7895	Intermediate Similarity	NPC315348
0.7895	Intermediate Similarity	NPC32002
0.7892	Intermediate Similarity	NPC471579
0.7891	Intermediate Similarity	NPC476131
0.7879	Intermediate Similarity	NPC201634
0.7872	Intermediate Similarity	NPC91958
0.7871	Intermediate Similarity	NPC204141
0.7866	Intermediate Similarity	NPC201700
0.7862	Intermediate Similarity	NPC476297
0.7857	Intermediate Similarity	NPC215795
0.7857	Intermediate Similarity	NPC176199
0.7843	Intermediate Similarity	NPC284635
0.784	Intermediate Similarity	NPC478185
0.784	Intermediate Similarity	NPC282231
0.784	Intermediate Similarity	NPC225018
0.7832	Intermediate Similarity	NPC182570
0.7832	Intermediate Similarity	NPC265605
0.7832	Intermediate Similarity	NPC48564
0.7829	Intermediate Similarity	NPC169433
0.7812	Intermediate Similarity	NPC51054
0.7811	Intermediate Similarity	NPC314919
0.7799	Intermediate Similarity	NPC138842
0.7798	Intermediate Similarity	NPC59269
0.7791	Intermediate Similarity	NPC478184
0.7791	Intermediate Similarity	NPC40779
0.7778	Intermediate Similarity	NPC329825
0.7778	Intermediate Similarity	NPC279918
0.7778	Intermediate Similarity	NPC104483
0.7765	Intermediate Similarity	NPC307191
0.7763	Intermediate Similarity	NPC125746
0.7758	Intermediate Similarity	NPC317430
0.7725	Intermediate Similarity	NPC314603
0.7725	Intermediate Similarity	NPC472123
0.7716	Intermediate Similarity	NPC293487
0.7716	Intermediate Similarity	NPC477591
0.7707	Intermediate Similarity	NPC316069
0.7702	Intermediate Similarity	NPC476464
0.7697	Intermediate Similarity	NPC56233
0.7697	Intermediate Similarity	NPC49217
0.7692	Intermediate Similarity	NPC151939
0.7683	Intermediate Similarity	NPC149265
0.7683	Intermediate Similarity	NPC194640
0.7676	Intermediate Similarity	NPC240136
0.7676	Intermediate Similarity	NPC297486
0.7676	Intermediate Similarity	NPC471402
0.7669	Intermediate Similarity	NPC131718
0.7667	Intermediate Similarity	NPC101165
0.7662	Intermediate Similarity	NPC312092
0.7661	Intermediate Similarity	NPC191415
0.7658	Intermediate Similarity	NPC477134
0.7657	Intermediate Similarity	NPC95783
0.7654	Intermediate Similarity	NPC265576
0.7654	Intermediate Similarity	NPC129721
0.7651	Intermediate Similarity	NPC329896
0.7651	Intermediate Similarity	NPC475090
0.7651	Intermediate Similarity	NPC475105
0.7636	Intermediate Similarity	NPC17751
0.7636	Intermediate Similarity	NPC280864
0.7622	Intermediate Similarity	NPC143603
0.7619	Intermediate Similarity	NPC161861
0.761	Intermediate Similarity	NPC2272
0.761	Intermediate Similarity	NPC37548
0.7607	Intermediate Similarity	NPC230869
0.7602	Intermediate Similarity	NPC300688
0.759	Intermediate Similarity	NPC478183
0.759	Intermediate Similarity	NPC54988
0.7588	Intermediate Similarity	NPC248454
0.7586	Intermediate Similarity	NPC94752
0.7584	Intermediate Similarity	NPC89490
0.758	Intermediate Similarity	NPC242556

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 NPC470233 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	426
0.1-0.2	686
0.2-0.3	1088
0.3-0.4	1991
0.4-0.5	2203
0.5-0.6	1725
0.6-0.7	799
0.7-0.8	204
0.8-0.85	25
0.85-0.9	2
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9653	High Similarity	NPD2837	Discontinued
0.9028	High Similarity	NPD1722	Approved
0.9013	High Similarity	NPD1853	Clinical (unspecified phase)
0.8759	High Similarity	NPD786	Approved
0.8725	High Similarity	NPD4547	Phase 3
0.871	High Similarity	NPD3323	Discontinued
0.8681	High Similarity	NPD198	Clinical (unspecified phase)
0.8667	High Similarity	NPD4374	Clinical (unspecified phase)
0.8667	High Similarity	NPD3100	Discontinued
0.858	High Similarity	NPD6277	Clinical (unspecified phase)
0.8543	High Similarity	NPD2430	Phase 2
0.8511	High Similarity	NPD2119	Approved
0.8511	High Similarity	NPD2118	Approved
0.8462	Intermediate Similarity	NPD3476	Approved
0.8462	Intermediate Similarity	NPD3475	Approved
0.8414	Intermediate Similarity	NPD3944	Approved
0.8414	Intermediate Similarity	NPD3942	Approved
0.8366	Intermediate Similarity	NPD2172	Phase 1
0.8333	Intermediate Similarity	NPD1192	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD4637	Clinical (unspecified phase)
0.8323	Intermediate Similarity	NPD3610	Approved
0.8323	Intermediate Similarity	NPD3609	Approved
0.8322	Intermediate Similarity	NPD3943	Clinical (unspecified phase)
0.8313	Intermediate Similarity	NPD2640	Approved
0.8313	Intermediate Similarity	NPD2641	Approved
0.8291	Intermediate Similarity	NPD2385	Clinical (unspecified phase)
0.8288	Intermediate Similarity	NPD4030	Approved
0.8288	Intermediate Similarity	NPD3385	Approved
0.8288	Intermediate Similarity	NPD4028	Approved
0.8288	Intermediate Similarity	NPD4029	Approved
0.8214	Intermediate Similarity	NPD4426	Clinical (unspecified phase)
0.8212	Intermediate Similarity	NPD2006	Phase 2
0.8182	Intermediate Similarity	NPD3341	Clinical (unspecified phase)
0.8158	Intermediate Similarity	NPD5254	Discontinued
0.8125	Intermediate Similarity	NPD991	Phase 2
0.8125	Intermediate Similarity	NPD992	Clinical (unspecified phase)
0.8121	Intermediate Similarity	NPD4181	Approved
0.811	Intermediate Similarity	NPD5065	Approved
0.8092	Intermediate Similarity	NPD2007	Clinical (unspecified phase)
0.8082	Intermediate Similarity	NPD715	Phase 3
0.8059	Intermediate Similarity	NPD5590	Clinical (unspecified phase)
0.8037	Intermediate Similarity	NPD5436	Phase 1
0.8	Intermediate Similarity	NPD1403	Approved
0.8	Intermediate Similarity	NPD1404	Approved
0.7987	Intermediate Similarity	NPD4880	Discontinued
0.7975	Intermediate Similarity	NPD976	Approved
0.7975	Intermediate Similarity	NPD975	Approved
0.7975	Intermediate Similarity	NPD977	Approved
0.7975	Intermediate Similarity	NPD5069	Clinical (unspecified phase)
0.7975	Intermediate Similarity	NPD4779	Clinical (unspecified phase)
0.7952	Intermediate Similarity	NPD4075	Phase 2
0.7941	Intermediate Similarity	NPD6610	Clinical (unspecified phase)
0.7935	Intermediate Similarity	NPD1683	Approved
0.7914	Intermediate Similarity	NPD2642	Approved
0.7914	Intermediate Similarity	NPD2639	Approved
0.7904	Intermediate Similarity	NPD3505	Approved
0.7904	Intermediate Similarity	NPD3506	Approved
0.7895	Intermediate Similarity	NPD2069	Approved
0.7895	Intermediate Similarity	NPD2074	Approved
0.7895	Intermediate Similarity	NPD768	Clinical (unspecified phase)
0.7895	Intermediate Similarity	NPD2073	Approved
0.7895	Intermediate Similarity	NPD2068	Approved
0.7895	Intermediate Similarity	NPD2072	Approved
0.7895	Intermediate Similarity	NPD2075	Approved
0.7895	Intermediate Similarity	NPD2071	Approved
0.7895	Intermediate Similarity	NPD2070	Approved
0.7895	Intermediate Similarity	NPD3378	Clinical (unspecified phase)
0.7892	Intermediate Similarity	NPD4128	Approved
0.7891	Intermediate Similarity	NPD3654	Approved
0.7881	Intermediate Similarity	NPD45	Approved
0.7881	Intermediate Similarity	NPD6554	Approved
0.7866	Intermediate Similarity	NPD2185	Clinical (unspecified phase)
0.7861	Intermediate Similarity	NPD5145	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD4076	Approved
0.7857	Intermediate Similarity	NPD4079	Approved
0.784	Intermediate Similarity	NPD5315	Discontinued
0.7832	Intermediate Similarity	NPD270	Clinical (unspecified phase)
0.7832	Intermediate Similarity	NPD268	Approved
0.7832	Intermediate Similarity	NPD271	Approved
0.7821	Intermediate Similarity	NPD7469	Discontinued
0.7818	Intermediate Similarity	NPD4184	Clinical (unspecified phase)
0.7812	Intermediate Similarity	NPD2580	Discontinued
0.7808	Intermediate Similarity	NPD9583	Approved
0.7806	Intermediate Similarity	NPD1918	Clinical (unspecified phase)
0.7799	Intermediate Similarity	NPD3339	Approved
0.7798	Intermediate Similarity	NPD7111	Discontinued
0.7798	Intermediate Similarity	NPD6203	Clinical (unspecified phase)
0.7785	Intermediate Similarity	NPD4463	Approved
0.7785	Intermediate Similarity	NPD4462	Approved
0.7771	Intermediate Similarity	NPD5934	Clinical (unspecified phase)
0.7765	Intermediate Similarity	NPD5806	Clinical (unspecified phase)
0.7764	Intermediate Similarity	NPD2865	Clinical (unspecified phase)
0.7764	Intermediate Similarity	NPD4326	Phase 2
0.7751	Intermediate Similarity	NPD2930	Clinical (unspecified phase)
0.775	Intermediate Similarity	NPD2165	Phase 1
0.7746	Intermediate Similarity	NPD3486	Clinical (unspecified phase)
0.7744	Intermediate Similarity	NPD5744	Clinical (unspecified phase)
0.774	Intermediate Similarity	NPD6278	Clinical (unspecified phase)
0.7706	Intermediate Similarity	NPD6595	Phase 3
0.7702	Intermediate Similarity	NPD3112	Approved
0.7702	Intermediate Similarity	NPD3115	Approved
0.7702	Intermediate Similarity	NPD3113	Approved
0.7702	Intermediate Similarity	NPD3114	Approved
0.7702	Intermediate Similarity	NPD473	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD1253	Approved
0.7697	Intermediate Similarity	NPD1255	Approved
0.7697	Intermediate Similarity	NPD1254	Approved
0.7697	Intermediate Similarity	NPD1256	Approved
0.7688	Intermediate Similarity	NPD6217	Discontinued
0.7674	Intermediate Similarity	NPD6178	Phase 3
0.7671	Intermediate Similarity	NPD9357	Approved
0.767	Intermediate Similarity	NPD4615	Phase 2
0.7669	Intermediate Similarity	NPD6454	Clinical (unspecified phase)
0.7661	Intermediate Similarity	NPD4649	Clinical (unspecified phase)
0.7658	Intermediate Similarity	NPD4702	Approved
0.7658	Intermediate Similarity	NPD4703	Approved
0.7654	Intermediate Similarity	NPD6497	Approved
0.7651	Intermediate Similarity	NPD2333	Discontinued
0.7651	Intermediate Similarity	NPD5862	Discovery
0.765	Intermediate Similarity	NPD4023	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD1262	Discovery
0.764	Intermediate Similarity	NPD2960	Clinical (unspecified phase)
0.7622	Intermediate Similarity	NPD6771	Discontinued
0.7616	Intermediate Similarity	NPD5105	Approved
0.7616	Intermediate Similarity	NPD5106	Approved
0.7616	Intermediate Similarity	NPD5728	Clinical (unspecified phase)
0.7614	Intermediate Similarity	NPD6180	Clinical (unspecified phase)
0.7614	Intermediate Similarity	NPD3419	Clinical (unspecified phase)
0.7607	Intermediate Similarity	NPD5418	Discontinued
0.7605	Intermediate Similarity	NPD4024	Phase 3
0.7602	Intermediate Similarity	NPD5473	Discontinued
0.7593	Intermediate Similarity	NPD2748	Clinical (unspecified phase)
0.7588	Intermediate Similarity	NPD2144	Approved
0.756	Intermediate Similarity	NPD6827	Clinical (unspecified phase)
0.756	Intermediate Similarity	NPD1567	Clinical (unspecified phase)
0.756	Intermediate Similarity	NPD6828	Phase 2
0.7558	Intermediate Similarity	NPD1708	Approved
0.7558	Intermediate Similarity	NPD3038	Discontinued
0.7558	Intermediate Similarity	NPD1707	Approved
0.7552	Intermediate Similarity	NPD9392	Approved
0.7552	Intermediate Similarity	NPD9396	Approved
0.755	Intermediate Similarity	NPD1251	Discontinued
0.755	Intermediate Similarity	NPD803	Phase 1
0.7545	Intermediate Similarity	NPD2390	Clinical (unspecified phase)
0.7543	Intermediate Similarity	NPD3961	Discontinued
0.7535	Intermediate Similarity	NPD269	Clinical (unspecified phase)
0.753	Intermediate Similarity	NPD2719	Clinical (unspecified phase)
0.753	Intermediate Similarity	NPD2720	Phase 1
0.7529	Intermediate Similarity	NPD2406	Clinical (unspecified phase)
0.7517	Intermediate Similarity	NPD1598	Discontinued
0.7515	Intermediate Similarity	NPD4112	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD1332	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD5962	Phase 2
0.75	Intermediate Similarity	NPD1993	Approved
0.75	Intermediate Similarity	NPD2875	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1995	Approved
0.75	Intermediate Similarity	NPD1994	Approved
0.75	Intermediate Similarity	NPD6288	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD3830	Phase 1
0.7486	Intermediate Similarity	NPD7619	Phase 3
0.7486	Intermediate Similarity	NPD7618	Phase 3
0.7485	Intermediate Similarity	NPD2150	Discontinued
0.7485	Intermediate Similarity	NPD2478	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD6148	Clinical (unspecified phase)
0.7471	Intermediate Similarity	NPD3607	Clinical (unspecified phase)
0.7471	Intermediate Similarity	NPD7564	Discontinued
0.7471	Intermediate Similarity	NPD5892	Approved
0.7468	Intermediate Similarity	NPD5671	Approved
0.7457	Intermediate Similarity	NPD1895	Discontinued
0.7443	Intermediate Similarity	NPD8431	Approved
0.744	Intermediate Similarity	NPD4640	Approved
0.744	Intermediate Similarity	NPD4638	Approved
0.744	Intermediate Similarity	NPD4639	Approved
0.7429	Intermediate Similarity	NPD4298	Clinical (unspecified phase)
0.7427	Intermediate Similarity	NPD6375	Clinical (unspecified phase)
0.7417	Intermediate Similarity	NPD947	Approved
0.7415	Intermediate Similarity	NPD748	Clinical (unspecified phase)
0.7403	Intermediate Similarity	NPD6664	Approved
0.7401	Intermediate Similarity	NPD8110	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD5255	Approved
0.7391	Intermediate Similarity	NPD5538	Clinical (unspecified phase)
0.7377	Intermediate Similarity	NPD6816	Phase 3
0.7375	Intermediate Similarity	NPD1528	Clinical (unspecified phase)
0.7374	Intermediate Similarity	NPD4922	Phase 2
0.7368	Intermediate Similarity	NPD3859	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD3583	Phase 2
0.7362	Intermediate Similarity	NPD1917	Discontinued
0.7358	Intermediate Similarity	NPD3401	Clinical (unspecified phase)
0.7346	Intermediate Similarity	NPD2466	Phase 3
0.7346	Intermediate Similarity	NPD2462	Phase 3
0.7346	Intermediate Similarity	NPD2465	Approved
0.7345	Intermediate Similarity	NPD7394	Phase 2
0.7337	Intermediate Similarity	NPD4318	Clinical (unspecified phase)
0.733	Intermediate Similarity	NPD7424	Clinical (unspecified phase)
0.733	Intermediate Similarity	NPD2868	Clinical (unspecified phase)
0.7326	Intermediate Similarity	NPD749	Clinical (unspecified phase)
0.7326	Intermediate Similarity	NPD3348	Phase 2
0.7326	Intermediate Similarity	NPD6044	Discontinued
0.7326	Intermediate Similarity	NPD2751	Phase 1
0.7325	Intermediate Similarity	NPD680	Discontinued

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