NPASS Compound

Structure

CID191774 OpenBabel06191715572D 30 29 0 0 1 0 0 0 0 0999 V2000 -9.5263 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.3923 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6603 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.5263 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.7942 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.0622 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.1962 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 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 -7.7942 2.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -0.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 4.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 12 1 0 0 0 0 2 12 1 0 0 0 0 3 13 1 0 0 0 0 4 13 1 0 0 0 0 5 14 1 0 0 0 0 6 7 1 0 0 0 0 6 8 1 0 0 0 0 8 23 1 0 0 0 0 9 12 1 0 0 0 0 10 13 1 0 0 0 0 11 15 1 0 0 0 0 11 27 2 0 0 0 0 14 24 2 3 0 0 0 14 28 1 0 0 0 0 15 7 1 6 0 0 0 15 25 1 0 0 0 0 16 9 1 6 0 0 0 16 19 1 0 0 0 0 16 24 1 0 0 0 0 17 10 1 6 0 0 0 17 18 1 0 0 0 0 17 26 1 0 0 0 0 18 25 2 3 0 0 0 18 29 1 0 0 0 0 19 26 2 3 0 0 0 19 30 1 0 0 0 0 20 21 2 0 0 0 0 20 22 1 0 0 0 0 20 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	426.3
Volume:	442.435
LogP:	0.277
LogD:	-0.126
LogS:	-2.063
# Rotatable Bonds:	18
TPSA:	166.27
# H-Bond Aceptor:	10
# H-Bond Donor:	7
# Rings:	0
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.099
Synthetic Accessibility Score:	3.544
Fsp3:	0.75
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.275
MDCK Permeability:	0.00010194296919507906
Pgp-inhibitor:	0.003
Pgp-substrate:	0.994
Human Intestinal Absorption (HIA):	0.355
20% Bioavailability (F20%):	0.028
30% Bioavailability (F30%):	0.005

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.09
Plasma Protein Binding (PPB):	13.724603652954102%
Volume Distribution (VD):	0.891
Pgp-substrate:	79.23194885253906%

ADMET: Metabolism

CYP1A2-inhibitor:	0.003
CYP1A2-substrate:	0.046
CYP2C19-inhibitor:	0.051
CYP2C19-substrate:	0.053
CYP2C9-inhibitor:	0.045
CYP2C9-substrate:	0.068
CYP2D6-inhibitor:	0.008
CYP2D6-substrate:	0.142
CYP3A4-inhibitor:	0.043
CYP3A4-substrate:	0.114

ADMET: Excretion

Clearance (CL):	2.97
Half-life (T1/2):	0.689

ADMET: Toxicity

hERG Blockers:	0.035
Human Hepatotoxicity (H-HT):	0.096
Drug-inuced Liver Injury (DILI):	0.018
AMES Toxicity:	0.084
Rat Oral Acute Toxicity:	0.062
Maximum Recommended Daily Dose:	0.025
Skin Sensitization:	0.335
Carcinogencity:	0.024
Eye Corrosion:	0.003
Eye Irritation:	0.01
Respiratory Toxicity:	0.044

Download Data

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

Natural Product: NPC191774

Natural Product ID:	NPC191774
*Common Name:**	Leupeptin
IUPAC Name:	(2S)-2-acetamido-N-[(2S)-1-[[(2S)-5-(diaminomethylideneamino)-1-oxopentan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]-4-methylpentanamide
Synonyms:	Leupeptin
Standard InCHIKey:	GDBQQVLCIARPGH-ULQDDVLXSA-N
Standard InCHI:	InChI=1S/C20H38N6O4/c1-12(2)9-16(24-14(5)28)19(30)26-17(10-13(3)4)18(29)25-15(11-27)7-6-8-23-20(21)22/h11-13,15-17H,6-10H2,1-5H3,(H,24,28)(H,25,29)(H,26,30)(H4,21,22,23)/t15-,16-,17-/m0/s1
SMILES:	O=C[C@@H](N=C([C@@H](N=C([C@@H](N=C(O)C)CC(C)C)O)CC(C)C)O)CCCNC(=N)N
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL191881
PubChem CID:	72429
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0000265] Carboxylic acids and derivatives [CHEMONTID:0000013] Amino acids, peptides, and analogues [CHEMONTID:0000348] Peptides

*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
NPO21559	Blumea balsamifera	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15787457]
NPO21559	Blumea balsamifera	Species	Asteraceae	Eukaryota	n.a.	leaf	n.a.	PMID[21319848]
NPO40969	0stoc sp. FSN	Strain	0stocaceae	Bacteria	n.a.	n.a.	n.a.	PMID[25069058]
NPO14826	Streptomyces mobaraensis	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[32998509]
NPO21559	Blumea balsamifera	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21559	Blumea balsamifera	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21559	Blumea balsamifera	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO21559	Blumea balsamifera	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14826	Streptomyces mobaraensis	Species	Streptomycetaceae	Bacteria	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	30
Ki	14
Others	36
Potency	2

Activity Type	# Activity
Cell Line	1
Individual Protein	59
Organism	9
Others	11
Protein-Protein Interaction	1
SINGLE PROTEIN	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT3579	Individual Protein	Calpain 1	Homo sapiens	IC50	=	300.0	nM	PMID[532829]
NPT165	Cell Line	HeLa	Homo sapiens	TC50	>	224.0	uM	PMID[532830]
NPT214	Individual Protein	Cathepsin B	Homo sapiens	IC50	=	117.0	nM	PMID[532831]
NPT214	Individual Protein	Cathepsin B	Homo sapiens	Ratio	=	1.66	n.a.	PMID[532831]
NPT469	Individual Protein	Cathepsin L	Homo sapiens	IC50	=	6.6	nM	PMID[532832]
NPT214	Individual Protein	Cathepsin B	Homo sapiens	IC50	=	9.4	nM	PMID[532832]
NPT469	Individual Protein	Cathepsin L	Homo sapiens	IC50	=	2.5	nM	PMID[532832]
NPT1568	Individual Protein	Trypsin I	Bos taurus	IC50	=	8100.0	nM	PMID[532833]
NPT5075	Individual Protein	Plasma kallikrein	Homo sapiens	IC50	=	40000.0	nM	PMID[532833]
NPT2534	Individual Protein	Thrombin	Bos taurus	IC50	=	12000.0	nM	PMID[532833]
NPT5076	Individual Protein	Plasminogen	Bos taurus	IC50	=	3700.0	nM	PMID[532833]
NPT5077	Individual Protein	Cathepsin B	Bos taurus	IC50	=	310.0	nM	PMID[532833]
NPT214	Individual Protein	Cathepsin B	Homo sapiens	Inhibition	~	15.0	%	PMID[532834]
NPT214	Individual Protein	Cathepsin B	Homo sapiens	Inhibition	~	25.0	%	PMID[532834]
NPT214	Individual Protein	Cathepsin B	Homo sapiens	Inhibition	~	35.0	%	PMID[532834]
NPT214	Individual Protein	Cathepsin B	Homo sapiens	Inhibition	~	55.0	%	PMID[532834]
NPT214	Individual Protein	Cathepsin B	Homo sapiens	Inhibition	~	75.0	%	PMID[532834]
NPT214	Individual Protein	Cathepsin B	Homo sapiens	Inhibition	~	82.0	%	PMID[532834]
NPT214	Individual Protein	Cathepsin B	Homo sapiens	Inhibition	~	95.0	%	PMID[532834]
NPT214	Individual Protein	Cathepsin B	Homo sapiens	Inhibition	~	100.0	%	PMID[532834]
NPT214	Individual Protein	Cathepsin B	Homo sapiens	IC50	=	0.0092	ug.mL-1	PMID[532834]
NPT3939	Individual Protein	Falcipain 2	Plasmodium falciparum	IC50	=	5.8	nM	PMID[532835]
NPT5078	Individual Protein	Cysteine protease	Leishmania donovani	IC50	=	10.0	nM	PMID[532837]
NPT3595	Individual Protein	Cathepsin K	Homo sapiens	IC50	=	0.018	ug.mL-1	PMID[532838]
NPT4312	Individual Protein	Human rhinovirus A protease	Human rhinovirus sp.	Inhibition	=	57.0	%	PMID[532840]
NPT214	Individual Protein	Cathepsin B	Homo sapiens	IC50	=	47.0	nM	PMID[532845]
NPT1720	Individual Protein	Plasminogen	Homo sapiens	IC50	=	1200.0	nM	PMID[532846]
NPT5079	Individual Protein	Transmembrane protease serine 6	Homo sapiens	Ki	=	2400.0	nM	PMID[532847]
NPT5079	Individual Protein	Transmembrane protease serine 6	Homo sapiens	Ki	=	4100.0	nM	PMID[532847]
NPT5080	Individual Protein	Matriptase	Homo sapiens	Ki	=	1900.0	nM	PMID[532847]
NPT3939	Individual Protein	Falcipain 2	Plasmodium falciparum	IC50	=	87.0	nM	PMID[532849]
NPT3939	Individual Protein	Falcipain 2	Plasmodium falciparum	IC50	=	98.0	nM	PMID[532849]
NPT5082	Individual Protein	Cysteine protease falcipain-3	Plasmodium falciparum	IC50	=	87.0	nM	PMID[532849]
NPT5082	Individual Protein	Cysteine protease falcipain-3	Plasmodium falciparum	IC50	=	98.0	nM	PMID[532849]
NPT214	Individual Protein	Cathepsin B	Homo sapiens	Ki	=	5.0	nM	PMID[532852]
NPT5083	Individual Protein	Cathepsin B	Capra hircus	Activity	=	0.0	%	PMID[532853]
NPT5083	Individual Protein	Cathepsin B	Capra hircus	Activity	=	1.2	%	PMID[532853]
NPT5084	Individual Protein	Cathepsin H	Capra hircus	Activity	=	0.0	%	PMID[532853]
NPT5084	Individual Protein	Cathepsin H	Capra hircus	Activity	=	48.2	%	PMID[532853]
NPT5083	Individual Protein	Cathepsin B	Capra hircus	Ki	=	0.02	nM	PMID[532853]
NPT214	Individual Protein	Cathepsin B	Homo sapiens	Ki	=	7.0	nM	PMID[532853]
NPT5085	Individual Protein	Cathepsin H	Homo sapiens	Ki	=	9200.0	nM	PMID[532853]
NPT5083	Individual Protein	Cathepsin B	Capra hircus	Inhibition	=	98.8	%	PMID[532853]
NPT5084	Individual Protein	Cathepsin H	Capra hircus	Inhibition	=	51.8	%	PMID[532853]
NPT5083	Individual Protein	Cathepsin B	Capra hircus	Ki	=	12.5	nM	PMID[532855]
NPT214	Individual Protein	Cathepsin B	Homo sapiens	Ki	=	7.0	nM	PMID[532855]
NPT5085	Individual Protein	Cathepsin H	Homo sapiens	Ki	=	9200.0	nM	PMID[532855]
NPT5083	Individual Protein	Cathepsin B	Capra hircus	Activity	=	0.067	nmol/min/ml	PMID[532855]
NPT5084	Individual Protein	Cathepsin H	Capra hircus	Activity	=	0.241	nmol/min/ml	PMID[532855]
NPT5080	Individual Protein	Matriptase	Homo sapiens	Ki	=	696.0	nM	PMID[532856]
NPT5086	Individual Protein	Hepatocyte growth factor activator	Homo sapiens	Ki	=	188.0	nM	PMID[532856]
NPT5087	Individual Protein	Serine protease hepsin	Homo sapiens	Ki	=	61.0	nM	PMID[532856]
NPT3595	Individual Protein	Cathepsin K	Homo sapiens	Ki	=	24.0	nM	PMID[532857]
NPT201	Individual Protein	Papain	Carica papaya	IC50	=	2.2	nM	PMID[532859]
NPT201	Individual Protein	Papain	Carica papaya	Delta Tm	=	1.0	degrees C	PMID[532859]
NPT1538	Organism	Human rhinovirus sp.	Human rhinovirus sp.	IC50	>	224000.0	nM	PMID[532830]
NPT2	Others	Unspecified		IC50	=	70.3	nM	PMID[532831]
NPT2	Others	Unspecified		Ratio	=	1.4	n.a.	PMID[532832]
NPT485	Organism	Plasmodium falciparum (isolate K1 / Thailand)	Plasmodium falciparum K1	IC50	=	6260.0	nM	PMID[532835]
NPT32	Organism	Mus musculus	Mus musculus	Inhibition	=	87.02	%	PMID[532835]
NPT2	Others	Unspecified		Inhibition	=	0.0	%	PMID[532836]
NPT25048	SINGLE PROTEIN	Calpain 1	Sus scrofa	IC50	=	80.0	nM	PMID[532836]
NPT27	Others	Unspecified		Inhibition	=	87.02	%	PMID[532839]
NPT474	Organism	Plasmodium berghei	Plasmodium berghei	Inhibition	=	89.06	%	PMID[532842]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Activity	=	89.75	%	PMID[532843]
NPT474	Organism	Plasmodium berghei	Plasmodium berghei	Inhibition	=	89.06	%	PMID[532844]
NPT474	Organism	Plasmodium berghei	Plasmodium berghei	Inhibition	=	91.62	%	PMID[532848]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	18000.0	nM	PMID[532849]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	74000.0	nM	PMID[532849]
NPT533	Protein-Protein Interaction	Runt-related transcription factor 1/Core-binding factor subunit beta	Homo sapiens	Potency	n.a.	31622.8	nM	PMID[532850]
NPT2	Others	Unspecified		Potency	n.a.	112.2	nM	PMID[532850]
NPT863	Individual Protein	Trypsin	Sus scrofa	IC50	=	500.0	nM	PMID[532854]
NPT863	Individual Protein	Trypsin	Sus scrofa	IC50	>	200.0	nM	PMID[532854]
NPT2	Others	Unspecified		Ratio Ki	=	3.0	n.a.	PMID[532856]
NPT35	Others	n.a.		T1/2	=	0.125	hr	PMID[532858]
NPT35	Others	n.a.		T1/2	=	0.01667	hr	PMID[532858]
NPT2	Others	Unspecified		IC50	>	30000.0	nM	PMID[532859]
NPT2	Others	Unspecified		Delta Tm	=	0.2	degrees C	PMID[532859]

☑ 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 NPC191774 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	224
0.1-0.2	20294
0.2-0.3	18699
0.3-0.4	2457
0.4-0.5	689
0.5-0.6	273
0.6-0.7	52
0.7-0.8	8
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.7662	Intermediate Similarity	NPC328457
0.7179	Intermediate Similarity	NPC133183
0.6974	Remote Similarity	NPC103130
0.6974	Remote Similarity	NPC226453
0.6892	Remote Similarity	NPC327748
0.6892	Remote Similarity	NPC321468
0.6883	Remote Similarity	NPC278881
0.68	Remote Similarity	NPC329564
0.68	Remote Similarity	NPC327170
0.6795	Remote Similarity	NPC327985
0.675	Remote Similarity	NPC472579
0.6667	Remote Similarity	NPC316826
0.6667	Remote Similarity	NPC317143
0.6622	Remote Similarity	NPC317147
0.6494	Remote Similarity	NPC118429
0.6494	Remote Similarity	NPC314510
0.64	Remote Similarity	NPC318260
0.6338	Remote Similarity	NPC80350
0.6292	Remote Similarity	NPC314466
0.6265	Remote Similarity	NPC478256
0.6235	Remote Similarity	NPC476248
0.6234	Remote Similarity	NPC254541
0.6234	Remote Similarity	NPC321536
0.6234	Remote Similarity	NPC320598
0.6222	Remote Similarity	NPC84128
0.6222	Remote Similarity	NPC53858
0.622	Remote Similarity	NPC250953
0.6216	Remote Similarity	NPC316889
0.6216	Remote Similarity	NPC321118
0.6136	Remote Similarity	NPC37681
0.6118	Remote Similarity	NPC315897
0.6104	Remote Similarity	NPC176164
0.6104	Remote Similarity	NPC472578
0.6104	Remote Similarity	NPC189301
0.6087	Remote Similarity	NPC472351
0.6049	Remote Similarity	NPC41429
0.6024	Remote Similarity	NPC470110
0.602	Remote Similarity	NPC301010
0.5976	Remote Similarity	NPC325534
0.596	Remote Similarity	NPC280066
0.5952	Remote Similarity	NPC126779
0.5949	Remote Similarity	NPC143722
0.5946	Remote Similarity	NPC322946
0.5938	Remote Similarity	NPC320057
0.5934	Remote Similarity	NPC23984
0.5904	Remote Similarity	NPC470109
0.5889	Remote Similarity	NPC31756
0.5882	Remote Similarity	NPC476285
0.5862	Remote Similarity	NPC43219
0.5862	Remote Similarity	NPC138435
0.5854	Remote Similarity	NPC262615
0.5844	Remote Similarity	NPC38463
0.5844	Remote Similarity	NPC325985
0.5833	Remote Similarity	NPC304454
0.5824	Remote Similarity	NPC476117
0.5824	Remote Similarity	NPC476156
0.5824	Remote Similarity	NPC476137
0.5824	Remote Similarity	NPC476243
0.5823	Remote Similarity	NPC476537
0.5823	Remote Similarity	NPC216415
0.5795	Remote Similarity	NPC86064
0.5784	Remote Similarity	NPC472736
0.5783	Remote Similarity	NPC470108
0.5778	Remote Similarity	NPC316242
0.5773	Remote Similarity	NPC155230
0.5769	Remote Similarity	NPC278209
0.5761	Remote Similarity	NPC476302
0.5755	Remote Similarity	NPC128303
0.5747	Remote Similarity	NPC141325
0.5732	Remote Similarity	NPC313420
0.573	Remote Similarity	NPC476324
0.573	Remote Similarity	NPC476130
0.5714	Remote Similarity	NPC478017
0.5714	Remote Similarity	NPC471258
0.5714	Remote Similarity	NPC304455
0.5714	Remote Similarity	NPC475801
0.5714	Remote Similarity	NPC315535
0.5714	Remote Similarity	NPC322573
0.5714	Remote Similarity	NPC312315
0.5714	Remote Similarity	NPC474593
0.5714	Remote Similarity	NPC315131
0.5714	Remote Similarity	NPC259586
0.5701	Remote Similarity	NPC241394
0.57	Remote Similarity	NPC216278
0.5699	Remote Similarity	NPC6902
0.5698	Remote Similarity	NPC476291
0.5686	Remote Similarity	NPC471257
0.5682	Remote Similarity	NPC161774
0.5682	Remote Similarity	NPC266888
0.5682	Remote Similarity	NPC256312
0.5676	Remote Similarity	NPC328378
0.5676	Remote Similarity	NPC245027
0.5676	Remote Similarity	NPC162620
0.5676	Remote Similarity	NPC62045
0.5667	Remote Similarity	NPC472594
0.5664	Remote Similarity	NPC470621
0.5664	Remote Similarity	NPC222481
0.5663	Remote Similarity	NPC174304
0.5663	Remote Similarity	NPC325597
0.5658	Remote Similarity	NPC245768
0.5658	Remote Similarity	NPC137327
0.5657	Remote Similarity	NPC474576
0.5647	Remote Similarity	NPC319046
0.5647	Remote Similarity	NPC81647
0.5638	Remote Similarity	NPC235078
0.5635	Remote Similarity	NPC314835
0.5625	Remote Similarity	NPC477539
0.5618	Remote Similarity	NPC327272
0.5612	Remote Similarity	NPC275715
0.56	Remote Similarity	NPC173763
0.56	Remote Similarity	NPC471098
0.56	Remote Similarity	NPC62263

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 NPC191774 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	77
0.1-0.2	2184
0.2-0.3	5505
0.3-0.4	986
0.4-0.5	289
0.5-0.6	84
0.6-0.7	18
0.7-0.8	6
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
1.0	High Similarity	NPD4278	Clinical (unspecified phase)
0.7711	Intermediate Similarity	NPD4829	Discontinued
0.7692	Intermediate Similarity	NPD366	Approved
0.7143	Intermediate Similarity	NPD9233	Phase 3
0.7143	Intermediate Similarity	NPD9232	Phase 2
0.7143	Intermediate Similarity	NPD9231	Phase 3
0.6974	Remote Similarity	NPD9045	Approved
0.6974	Remote Similarity	NPD9046	Phase 3
0.6974	Remote Similarity	NPD9047	Approved
0.6974	Remote Similarity	NPD9048	Approved
0.6835	Remote Similarity	NPD9451	Clinical (unspecified phase)
0.68	Remote Similarity	NPD1155	Discontinued
0.6701	Remote Similarity	NPD4825	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2702	Phase 1
0.6667	Remote Similarity	NPD2704	Phase 3
0.6629	Remote Similarity	NPD3733	Clinical (unspecified phase)
0.6585	Remote Similarity	NPD5386	Phase 2
0.6494	Remote Similarity	NPD9014	Approved
0.6341	Remote Similarity	NPD3213	Discontinued
0.63	Remote Similarity	NPD6120	Clinical (unspecified phase)
0.6275	Remote Similarity	NPD6122	Discontinued
0.6146	Remote Similarity	NPD5792	Clinical (unspecified phase)
0.6129	Remote Similarity	NPD7759	Phase 2
0.6129	Remote Similarity	NPD7760	Phase 2
0.6118	Remote Similarity	NPD6944	Clinical (unspecified phase)
0.6118	Remote Similarity	NPD1825	Clinical (unspecified phase)
0.6104	Remote Similarity	NPD9433	Approved
0.6095	Remote Similarity	NPD1827	Clinical (unspecified phase)
0.6095	Remote Similarity	NPD1828	Approved
0.6095	Remote Similarity	NPD1829	Clinical (unspecified phase)
0.6092	Remote Similarity	NPD9224	Clinical (unspecified phase)
0.6061	Remote Similarity	NPD7841	Clinical (unspecified phase)
0.6044	Remote Similarity	NPD2683	Discontinued
0.5976	Remote Similarity	NPD2703	Discontinued
0.5976	Remote Similarity	NPD8952	Approved
0.5952	Remote Similarity	NPD3724	Clinical (unspecified phase)
0.5952	Remote Similarity	NPD4242	Approved
0.5946	Remote Similarity	NPD9441	Phase 2
0.5934	Remote Similarity	NPD7762	Phase 2
0.5934	Remote Similarity	NPD7763	Phase 2
0.5918	Remote Similarity	NPD6699	Clinical (unspecified phase)
0.5904	Remote Similarity	NPD1429	Clinical (unspecified phase)
0.5904	Remote Similarity	NPD2263	Discontinued
0.5854	Remote Similarity	NPD6438	Approved
0.5854	Remote Similarity	NPD6437	Approved
0.5833	Remote Similarity	NPD4241	Registered
0.5833	Remote Similarity	NPD3177	Phase 3
0.5816	Remote Similarity	NPD4261	Phase 1
0.5816	Remote Similarity	NPD6431	Approved
0.5816	Remote Similarity	NPD6432	Approved
0.5816	Remote Similarity	NPD6433	Approved
0.5816	Remote Similarity	NPD6434	Clinical (unspecified phase)
0.5814	Remote Similarity	NPD5382	Phase 2
0.5806	Remote Similarity	NPD7643	Phase 1
0.5794	Remote Similarity	NPD6937	Approved
0.5794	Remote Similarity	NPD8175	Discontinued
0.5784	Remote Similarity	NPD8038	Phase 2
0.5765	Remote Similarity	NPD620	Approved
0.5747	Remote Similarity	NPD1147	Phase 2
0.5729	Remote Similarity	NPD3176	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD7917	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD7918	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD886	Clinical (unspecified phase)
0.57	Remote Similarity	NPD6426	Approved
0.57	Remote Similarity	NPD6423	Approved
0.57	Remote Similarity	NPD6427	Approved
0.57	Remote Similarity	NPD6425	Approved
0.5676	Remote Similarity	NPD9018	Approved
0.5663	Remote Similarity	NPD348	Approved
0.5647	Remote Similarity	NPD337	Discontinued
0.5647	Remote Similarity	NPD9452	Clinical (unspecified phase)
0.5644	Remote Similarity	NPD6424	Approved
0.5632	Remote Similarity	NPD2262	Clinical (unspecified phase)
0.5625	Remote Similarity	NPD3723	Clinical (unspecified phase)
0.5625	Remote Similarity	NPD5791	Phase 2

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