NPASS Compound

Structure

CID191310 OpenBabel06191715572D 24 25 0 0 0 0 0 0 0 0999 V2000 2.5981 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 2.5000 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 1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 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 -1.5000 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 -0.8660 1.5000 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 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 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 -0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 5 1 0 0 0 0 2 6 1 0 0 0 0 3 12 1 0 0 0 0 4 13 1 0 0 0 0 5 23 1 0 0 0 0 6 24 1 0 0 0 0 7 8 2 0 0 0 0 7 9 1 0 0 0 0 8 10 1 0 0 0 0 9 11 2 0 0 0 0 10 14 2 0 0 0 0 11 14 1 0 0 0 0 12 15 1 0 0 0 0 12 20 2 0 0 0 0 13 16 2 0 0 0 0 13 20 1 0 0 0 0 14 17 1 0 0 0 0 15 17 2 0 0 0 0 15 18 1 0 0 0 0 16 17 1 0 0 0 0 16 19 1 0 0 0 0 18 21 2 0 0 0 0 18 23 1 0 0 0 0 19 22 2 0 0 0 0 19 24 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	327.15
Volume:	345.133
LogP:	3.298
LogD:	2.666
LogS:	-4.258
# Rotatable Bonds:	7
TPSA:	65.49
# H-Bond Aceptor:	5
# H-Bond Donor:	0
# Rings:	2
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.783
Synthetic Accessibility Score:	2.039
Fsp3:	0.316
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:	-4.639
MDCK Permeability:	3.688268407131545e-05
Pgp-inhibitor:	0.08
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.002
20% Bioavailability (F20%):	0.86
30% Bioavailability (F30%):	0.798

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.16
Plasma Protein Binding (PPB):	94.3472671508789%
Volume Distribution (VD):	1.684
Pgp-substrate:	1.590042233467102%

ADMET: Metabolism

CYP1A2-inhibitor:	0.939
CYP1A2-substrate:	0.827
CYP2C19-inhibitor:	0.844
CYP2C19-substrate:	0.134
CYP2C9-inhibitor:	0.866
CYP2C9-substrate:	0.552
CYP2D6-inhibitor:	0.792
CYP2D6-substrate:	0.46
CYP3A4-inhibitor:	0.498
CYP3A4-substrate:	0.235

ADMET: Excretion

Clearance (CL):	7.586
Half-life (T1/2):	0.096

ADMET: Toxicity

hERG Blockers:	0.772
Human Hepatotoxicity (H-HT):	0.112
Drug-inuced Liver Injury (DILI):	0.919
AMES Toxicity:	0.013
Rat Oral Acute Toxicity:	0.011
Maximum Recommended Daily Dose:	0.012
Skin Sensitization:	0.226
Carcinogencity:	0.12
Eye Corrosion:	0.003
Eye Irritation:	0.401
Respiratory Toxicity:	0.754

Download Data

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

Natural Product: NPC191310

Natural Product ID:	NPC191310
*Common Name:**	Diethyl 2,6-Dimethyl-4-Phenylpyridine-3,5-Dicarboxylate
IUPAC Name:	diethyl 2,6-dimethyl-4-phenylpyridine-3,5-dicarboxylate
Synonyms:
Standard InCHIKey:	VQDKSJMDSZZJER-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C19H21NO4/c1-5-23-18(21)15-12(3)20-13(4)16(19(22)24-6-2)17(15)14-10-8-7-9-11-14/h7-11H,5-6H2,1-4H3
SMILES:	CCOC(=O)c1c(C)nc(C)c(c1c1ccccc1)C(=O)OCC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1583690
PubChem CID:	629929
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000089] Pyridines and derivatives [CHEMONTID:0002317] Phenylpyridines

*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
NPO912	Kadsura coccinea	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18027905]
NPO912	Kadsura coccinea	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18271558]
NPO912	Kadsura coccinea	Species	Schisandraceae	Eukaryota	roots	n.a.	n.a.	PMID[18491866]
NPO912	Kadsura coccinea	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18590312]
NPO4186	Haliclona tulearensis	Species	Chalinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[19894692]
NPO912	Kadsura coccinea	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24299567]
NPO912	Kadsura coccinea	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26214125]
NPO912	Kadsura coccinea	Species	Schisandraceae	Eukaryota	Stems	n.a.	n.a.	PMID[27704807]
NPO912	Kadsura coccinea	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12905	Holcus mollis	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1364	Styrax macranthus	Species	Styracaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO912	Kadsura coccinea	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4532	Rubia sikkimensis	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8114	Vernonia sublutea	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4186	Haliclona tulearensis	Species	Chalinidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO79	Jatropha elliptica	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO462	Rhamnus prinoides	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1510	Meehania fargesii	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2104	Callicarpa pentandra	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO630	Piptothrix sinaloae	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO20280	Cassia abbreviata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8411	Alphonsea mollis	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10371	Lesquerella angustifolia	n.a.	n.a.	n.a.	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
Potency	21

Activity Type	# Activity
Individual Protein	17
Organism	2
Uncleic Acid	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT483	Individual Protein	Prelamin-A/C	Homo sapiens	Potency	=	6309.6	nM	PMID[521154]
NPT48	Individual Protein	Lysine-specific demethylase 4D-like	Homo sapiens	Potency	=	28183.8	nM	PMID[521154]
NPT537	Individual Protein	Ras-related protein Rab-9A	Homo sapiens	Potency	=	2238.7	nM	PMID[521154]
NPT53	Individual Protein	4'-phosphopantetheinyl transferase ffp	Bacillus subtilis	Potency	=	44668.4	nM	PMID[521154]
NPT51	Individual Protein	Microtubule-associated protein tau	Homo sapiens	Potency	=	5623.4	nM	PMID[521154]
NPT538	Individual Protein	Niemann-Pick C1 protein	Homo sapiens	Potency	=	3981.1	nM	PMID[521154]
NPT151	Individual Protein	15-hydroxyprostaglandin dehydrogenase [NAD+]	Homo sapiens	Potency	=	31622.8	nM	PMID[521154]
NPT1416	Individual Protein	Neuropeptide S receptor	Homo sapiens	Potency	=	25118.9	nM	PMID[521154]
NPT60	Individual Protein	Lysosomal alpha-glucosidase	Homo sapiens	Potency	=	31622.8	nM	PMID[521154]
NPT539	Individual Protein	Cellular tumor antigen p53	Homo sapiens	Potency	n.a.	28183.8	nM	PMID[521154]
NPT64	Individual Protein	ATPase family AAA domain-containing protein 5	Homo sapiens	Potency	n.a.	7307.8	nM	PMID[521154]
NPT135	Individual Protein	Chromobox protein homolog 1	Homo sapiens	Potency	n.a.	89125.1	nM	PMID[521154]
NPT484	Individual Protein	Luciferin 4-monooxygenase	Photinus pyralis	Potency	n.a.	6012.0	nM	PMID[521154]
NPT11	Individual Protein	Guanine nucleotide-binding protein G(s), subunit alpha	Homo sapiens	Potency	n.a.	1584.9	nM	PMID[521154]
NPT536	Uncleic Acid	microRNA 21	Homo sapiens	Potency	=	3689.8	nM	PMID[521154]
NPT93	Individual Protein	Survival motor neuron protein	Homo sapiens	Potency	=	15848.9	nM	PMID[521154]
NPT94	Individual Protein	Aldehyde dehydrogenase 1A1	Homo sapiens	Potency	=	19952.6	nM	PMID[521154]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Potency	n.a.	293.6	nM	PMID[521154]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Potency	n.a.	928.5	nM	PMID[521154]

☑ 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 NPC191310 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	298
0.1-0.2	1748
0.2-0.3	6420
0.3-0.4	11540
0.4-0.5	16370
0.5-0.6	4601
0.6-0.7	1492
0.7-0.8	224
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8353	Intermediate Similarity	NPC84347
0.8284	Intermediate Similarity	NPC249614
0.8011	Intermediate Similarity	NPC317572
0.7953	Intermediate Similarity	NPC470894
0.7926	Intermediate Similarity	NPC313345
0.7926	Intermediate Similarity	NPC315638
0.7926	Intermediate Similarity	NPC313796
0.7926	Intermediate Similarity	NPC314855
0.7889	Intermediate Similarity	NPC44354
0.7884	Intermediate Similarity	NPC315545
0.7884	Intermediate Similarity	NPC314297
0.7877	Intermediate Similarity	NPC194040
0.7853	Intermediate Similarity	NPC314834
0.7778	Intermediate Similarity	NPC160381
0.7684	Intermediate Similarity	NPC314648
0.7676	Intermediate Similarity	NPC135950
0.7624	Intermediate Similarity	NPC282103
0.7606	Intermediate Similarity	NPC123395
0.7606	Intermediate Similarity	NPC280714
0.7606	Intermediate Similarity	NPC103361
0.76	Intermediate Similarity	NPC477788
0.7592	Intermediate Similarity	NPC132539
0.7574	Intermediate Similarity	NPC107287
0.7486	Intermediate Similarity	NPC90415
0.7475	Intermediate Similarity	NPC250807
0.7475	Intermediate Similarity	NPC57797
0.7473	Intermediate Similarity	NPC55493
0.7459	Intermediate Similarity	NPC469489
0.7451	Intermediate Similarity	NPC477787
0.7451	Intermediate Similarity	NPC122968
0.7451	Intermediate Similarity	NPC228377
0.7451	Intermediate Similarity	NPC328186
0.7447	Intermediate Similarity	NPC245916
0.7447	Intermediate Similarity	NPC109922
0.7444	Intermediate Similarity	NPC164340
0.7438	Intermediate Similarity	NPC473850
0.7437	Intermediate Similarity	NPC312645
0.7419	Intermediate Similarity	NPC138370
0.7418	Intermediate Similarity	NPC243058
0.7411	Intermediate Similarity	NPC476467
0.7411	Intermediate Similarity	NPC280473
0.7411	Intermediate Similarity	NPC323551
0.7394	Intermediate Similarity	NPC220151
0.7394	Intermediate Similarity	NPC19692
0.7385	Intermediate Similarity	NPC470190
0.738	Intermediate Similarity	NPC471546
0.7377	Intermediate Similarity	NPC207851
0.7377	Intermediate Similarity	NPC320394
0.7374	Intermediate Similarity	NPC51008
0.7374	Intermediate Similarity	NPC303225
0.7374	Intermediate Similarity	NPC41724
0.7366	Intermediate Similarity	NPC146824
0.7356	Intermediate Similarity	NPC322644
0.7351	Intermediate Similarity	NPC206186
0.7343	Intermediate Similarity	NPC292416
0.7343	Intermediate Similarity	NPC473689
0.7343	Intermediate Similarity	NPC316841
0.734	Intermediate Similarity	NPC81802
0.734	Intermediate Similarity	NPC472295
0.734	Intermediate Similarity	NPC269886
0.734	Intermediate Similarity	NPC247735
0.734	Intermediate Similarity	NPC472210
0.7337	Intermediate Similarity	NPC477979
0.7337	Intermediate Similarity	NPC112741
0.7337	Intermediate Similarity	NPC4421
0.733	Intermediate Similarity	NPC475362
0.7323	Intermediate Similarity	NPC473493
0.732	Intermediate Similarity	NPC289086
0.7317	Intermediate Similarity	NPC473506
0.7313	Intermediate Similarity	NPC187494
0.7308	Intermediate Similarity	NPC319880
0.7308	Intermediate Similarity	NPC244839
0.7308	Intermediate Similarity	NPC320324
0.7304	Intermediate Similarity	NPC76565
0.73	Intermediate Similarity	NPC42678
0.73	Intermediate Similarity	NPC207531
0.73	Intermediate Similarity	NPC477907
0.73	Intermediate Similarity	NPC477909
0.7286	Intermediate Similarity	NPC89508
0.7283	Intermediate Similarity	NPC203635
0.7282	Intermediate Similarity	NPC475631
0.7282	Intermediate Similarity	NPC475600
0.7282	Intermediate Similarity	NPC87152
0.7282	Intermediate Similarity	NPC476110
0.7273	Intermediate Similarity	NPC40919
0.7273	Intermediate Similarity	NPC470189
0.7273	Intermediate Similarity	NPC237702
0.7268	Intermediate Similarity	NPC475137
0.7268	Intermediate Similarity	NPC475498
0.7263	Intermediate Similarity	NPC472116
0.7259	Intermediate Similarity	NPC48042
0.7259	Intermediate Similarity	NPC472752
0.7259	Intermediate Similarity	NPC472550
0.7259	Intermediate Similarity	NPC304179
0.7253	Intermediate Similarity	NPC67659
0.7253	Intermediate Similarity	NPC256268
0.725	Intermediate Similarity	NPC264674
0.7246	Intermediate Similarity	NPC471190
0.7246	Intermediate Similarity	NPC470486
0.7246	Intermediate Similarity	NPC471977
0.7246	Intermediate Similarity	NPC475644
0.7245	Intermediate Similarity	NPC243850
0.7238	Intermediate Similarity	NPC475406
0.7236	Intermediate Similarity	NPC118940
0.7236	Intermediate Similarity	NPC244856
0.7228	Intermediate Similarity	NPC212768
0.7228	Intermediate Similarity	NPC319556
0.7228	Intermediate Similarity	NPC75600
0.7228	Intermediate Similarity	NPC473115
0.7228	Intermediate Similarity	NPC158020
0.7228	Intermediate Similarity	NPC6576
0.7228	Intermediate Similarity	NPC62367
0.7228	Intermediate Similarity	NPC473089
0.7222	Intermediate Similarity	NPC123839
0.7219	Intermediate Similarity	NPC63199
0.7219	Intermediate Similarity	NPC102338
0.7219	Intermediate Similarity	NPC111602
0.7219	Intermediate Similarity	NPC196251
0.7214	Intermediate Similarity	NPC85702
0.7214	Intermediate Similarity	NPC193361
0.7214	Intermediate Similarity	NPC62844
0.7208	Intermediate Similarity	NPC470280
0.7208	Intermediate Similarity	NPC63041
0.7204	Intermediate Similarity	NPC38959
0.7204	Intermediate Similarity	NPC327904
0.7202	Intermediate Similarity	NPC254240
0.7202	Intermediate Similarity	NPC128265
0.7202	Intermediate Similarity	NPC312870
0.7202	Intermediate Similarity	NPC294909
0.7202	Intermediate Similarity	NPC199851
0.72	Intermediate Similarity	NPC306644
0.72	Intermediate Similarity	NPC236424
0.72	Intermediate Similarity	NPC472291
0.7198	Intermediate Similarity	NPC234987
0.7198	Intermediate Similarity	NPC219848
0.7194	Intermediate Similarity	NPC309498
0.7192	Intermediate Similarity	NPC301368
0.7192	Intermediate Similarity	NPC216428
0.7192	Intermediate Similarity	NPC84815
0.7189	Intermediate Similarity	NPC472119
0.7186	Intermediate Similarity	NPC220337
0.7183	Intermediate Similarity	NPC253482
0.7179	Intermediate Similarity	NPC165599
0.7178	Intermediate Similarity	NPC471016
0.7177	Intermediate Similarity	NPC475596
0.7177	Intermediate Similarity	NPC475303
0.7164	Intermediate Similarity	NPC274842
0.7158	Intermediate Similarity	NPC192306
0.7157	Intermediate Similarity	NPC4687
0.7157	Intermediate Similarity	NPC477901
0.7156	Intermediate Similarity	NPC475426
0.715	Intermediate Similarity	NPC472553
0.715	Intermediate Similarity	NPC241024
0.715	Intermediate Similarity	NPC318299
0.7143	Intermediate Similarity	NPC30456
0.7135	Intermediate Similarity	NPC159125
0.7135	Intermediate Similarity	NPC141454
0.7129	Intermediate Similarity	NPC470306
0.7122	Intermediate Similarity	NPC477903
0.7122	Intermediate Similarity	NPC477912
0.7121	Intermediate Similarity	NPC266249
0.7121	Intermediate Similarity	NPC39679
0.712	Intermediate Similarity	NPC474121
0.7114	Intermediate Similarity	NPC317752
0.7114	Intermediate Similarity	NPC165837
0.7113	Intermediate Similarity	NPC214428
0.7112	Intermediate Similarity	NPC66210
0.7107	Intermediate Similarity	NPC300156
0.7101	Intermediate Similarity	NPC26881
0.7101	Intermediate Similarity	NPC233727
0.7101	Intermediate Similarity	NPC328154
0.7098	Intermediate Similarity	NPC324245
0.7098	Intermediate Similarity	NPC320748
0.7094	Intermediate Similarity	NPC477908
0.7094	Intermediate Similarity	NPC471014
0.7094	Intermediate Similarity	NPC6981
0.7094	Intermediate Similarity	NPC206343
0.7094	Intermediate Similarity	NPC475408
0.7087	Intermediate Similarity	NPC127720
0.7087	Intermediate Similarity	NPC127026
0.7087	Intermediate Similarity	NPC235364
0.7083	Intermediate Similarity	NPC475648
0.7083	Intermediate Similarity	NPC472293
0.7079	Intermediate Similarity	NPC319128
0.7079	Intermediate Similarity	NPC228331
0.7075	Intermediate Similarity	NPC327769
0.7075	Intermediate Similarity	NPC35208
0.7074	Intermediate Similarity	NPC472323
0.7073	Intermediate Similarity	NPC472099
0.7071	Intermediate Similarity	NPC193238
0.7071	Intermediate Similarity	NPC244741
0.7068	Intermediate Similarity	NPC230403
0.7065	Intermediate Similarity	NPC264176
0.7065	Intermediate Similarity	NPC111732
0.7065	Intermediate Similarity	NPC472098
0.7062	Intermediate Similarity	NPC472296
0.7062	Intermediate Similarity	NPC472297
0.7059	Intermediate Similarity	NPC294579
0.7059	Intermediate Similarity	NPC144779
0.7053	Intermediate Similarity	NPC471980

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 NPC191310 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	210
0.1-0.2	598
0.2-0.3	756
0.3-0.4	1173
0.4-0.5	3308
0.5-0.6	2498
0.6-0.7	553
0.7-0.8	52
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8378	Intermediate Similarity	NPD4506	Discontinued
0.8198	Intermediate Similarity	NPD6641	Approved
0.8198	Intermediate Similarity	NPD6642	Approved
0.8148	Intermediate Similarity	NPD6657	Clinical (unspecified phase)
0.799	Intermediate Similarity	NPD6770	Approved
0.7935	Intermediate Similarity	NPD4987	Clinical (unspecified phase)
0.7841	Intermediate Similarity	NPD8304	Clinical (unspecified phase)
0.7759	Intermediate Similarity	NPD485	Clinical (unspecified phase)
0.7676	Intermediate Similarity	NPD5975	Clinical (unspecified phase)
0.7592	Intermediate Similarity	NPD3947	Discontinued
0.7544	Intermediate Similarity	NPD820	Phase 3
0.7539	Intermediate Similarity	NPD2121	Clinical (unspecified phase)
0.7538	Intermediate Similarity	NPD4417	Approved
0.7487	Intermediate Similarity	NPD648	Clinical (unspecified phase)
0.7474	Intermediate Similarity	NPD2509	Approved
0.7474	Intermediate Similarity	NPD2510	Approved
0.7446	Intermediate Similarity	NPD4948	Discontinued
0.7366	Intermediate Similarity	NPD2564	Approved
0.7366	Intermediate Similarity	NPD2565	Phase 2
0.7348	Intermediate Similarity	NPD5398	Clinical (unspecified phase)
0.7337	Intermediate Similarity	NPD9271	Approved
0.7326	Intermediate Similarity	NPD5257	Clinical (unspecified phase)
0.7299	Intermediate Similarity	NPD1630	Approved
0.7268	Intermediate Similarity	NPD3925	Approved
0.7263	Intermediate Similarity	NPD6739	Clinical (unspecified phase)
0.7259	Intermediate Similarity	NPD6529	Discontinued
0.725	Intermediate Similarity	NPD5417	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD5003	Discontinued
0.7212	Intermediate Similarity	NPD4952	Phase 3
0.7202	Intermediate Similarity	NPD4500	Approved
0.7202	Intermediate Similarity	NPD4501	Approved
0.72	Intermediate Similarity	NPD3795	Approved
0.72	Intermediate Similarity	NPD3794	Approved
0.7191	Intermediate Similarity	NPD4554	Clinical (unspecified phase)
0.7186	Intermediate Similarity	NPD5475	Discontinued
0.7175	Intermediate Similarity	NPD1631	Approved
0.7157	Intermediate Similarity	NPD1996	Discontinued
0.7152	Intermediate Similarity	NPD2670	Approved
0.7143	Intermediate Similarity	NPD3946	Clinical (unspecified phase)
0.7129	Intermediate Similarity	NPD3394	Approved
0.7129	Intermediate Similarity	NPD3389	Approved
0.7129	Intermediate Similarity	NPD3393	Approved
0.7129	Intermediate Similarity	NPD8160	Phase 2
0.7109	Intermediate Similarity	NPD4373	Phase 2
0.7107	Intermediate Similarity	NPD7010	Phase 3
0.71	Intermediate Similarity	NPD5416	Discontinued
0.7085	Intermediate Similarity	NPD5583	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD5512	Phase 3
0.7059	Intermediate Similarity	NPD7878	Phase 2
0.7059	Intermediate Similarity	NPD1926	Approved
0.7056	Intermediate Similarity	NPD2844	Phase 3
0.7053	Intermediate Similarity	NPD2336	Approved
0.7045	Intermediate Similarity	NPD2582	Approved
0.7045	Intermediate Similarity	NPD2581	Approved
0.702	Intermediate Similarity	NPD4901	Clinical (unspecified phase)
0.7015	Intermediate Similarity	NPD6567	Clinical (unspecified phase)
0.7014	Intermediate Similarity	NPD6962	Phase 2
0.7005	Intermediate Similarity	NPD6160	Clinical (unspecified phase)
0.7005	Intermediate Similarity	NPD6176	Phase 1
0.7	Intermediate Similarity	NPD4499	Approved
0.6995	Remote Similarity	NPD3257	Approved
0.6995	Remote Similarity	NPD5293	Phase 2
0.6994	Remote Similarity	NPD2737	Clinical (unspecified phase)
0.6982	Remote Similarity	NPD107	Approved
0.6965	Remote Similarity	NPD4900	Clinical (unspecified phase)
0.6942	Remote Similarity	NPD6955	Clinical (unspecified phase)
0.6942	Remote Similarity	NPD7404	Approved
0.6942	Remote Similarity	NPD3258	Approved
0.694	Remote Similarity	NPD43	Approved
0.694	Remote Similarity	NPD6183	Clinical (unspecified phase)
0.694	Remote Similarity	NPD6182	Approved
0.6936	Remote Similarity	NPD7528	Approved
0.6935	Remote Similarity	NPD1643	Phase 3
0.6935	Remote Similarity	NPD3507	Phase 2
0.6931	Remote Similarity	NPD7703	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD7777	Approved
0.6923	Remote Similarity	NPD1573	Approved
0.6923	Remote Similarity	NPD53	Approved
0.6923	Remote Similarity	NPD1575	Approved
0.6923	Remote Similarity	NPD7778	Approved
0.6919	Remote Similarity	NPD2920	Discontinued
0.6908	Remote Similarity	NPD3280	Approved
0.6907	Remote Similarity	NPD6550	Discontinued
0.6907	Remote Similarity	NPD2307	Discontinued
0.6907	Remote Similarity	NPD7061	Clinical (unspecified phase)
0.6902	Remote Similarity	NPD4736	Clinical (unspecified phase)
0.6902	Remote Similarity	NPD1586	Approved
0.6901	Remote Similarity	NPD3525	Discontinued
0.6897	Remote Similarity	NPD5866	Approved
0.6885	Remote Similarity	NPD5472	Clinical (unspecified phase)
0.6884	Remote Similarity	NPD3006	Discontinued
0.6878	Remote Similarity	NPD2433	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD4301	Approved
0.6872	Remote Similarity	NPD4328	Approved
0.6872	Remote Similarity	NPD3259	Approved
0.6859	Remote Similarity	NPD4334	Discontinued
0.6854	Remote Similarity	NPD7688	Phase 1
0.685	Remote Similarity	NPD4862	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD4524	Discontinued
0.6839	Remote Similarity	NPD4376	Phase 3
0.6831	Remote Similarity	NPD4724	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD4667	Clinical (unspecified phase)
0.6825	Remote Similarity	NPD721	Approved
0.6821	Remote Similarity	NPD9075	Approved
0.6821	Remote Similarity	NPD9074	Approved
0.6816	Remote Similarity	NPD5429	Discontinued
0.6816	Remote Similarity	NPD3371	Approved
0.6812	Remote Similarity	NPD5632	Approved
0.6812	Remote Similarity	NPD7395	Discontinued
0.6809	Remote Similarity	NPD3435	Discontinued
0.6809	Remote Similarity	NPD4203	Approved
0.6809	Remote Similarity	NPD4204	Approved
0.6806	Remote Similarity	NPD5891	Approved
0.6805	Remote Similarity	NPD3170	Approved
0.6802	Remote Similarity	NPD6661	Clinical (unspecified phase)
0.68	Remote Similarity	NPD2831	Approved
0.68	Remote Similarity	NPD6987	Phase 1
0.68	Remote Similarity	NPD7396	Approved
0.68	Remote Similarity	NPD6323	Clinical (unspecified phase)
0.68	Remote Similarity	NPD5901	Discontinued
0.6798	Remote Similarity	NPD2836	Approved
0.6796	Remote Similarity	NPD5088	Discontinued
0.6791	Remote Similarity	NPD6741	Clinical (unspecified phase)
0.6791	Remote Similarity	NPD3920	Phase 2
0.6791	Remote Similarity	NPD1587	Approved
0.6789	Remote Similarity	NPD4889	Approved
0.6784	Remote Similarity	NPD6414	Clinical (unspecified phase)
0.6782	Remote Similarity	NPD1801	Approved
0.6782	Remote Similarity	NPD1802	Approved
0.678	Remote Similarity	NPD7571	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD5471	Phase 3
0.6762	Remote Similarity	NPD6995	Phase 1
0.676	Remote Similarity	NPD4670	Clinical (unspecified phase)
0.676	Remote Similarity	NPD4671	Clinical (unspecified phase)
0.676	Remote Similarity	NPD4669	Clinical (unspecified phase)
0.6754	Remote Similarity	NPD5256	Discontinued
0.6754	Remote Similarity	NPD5444	Phase 1
0.6753	Remote Similarity	NPD4950	Approved
0.6751	Remote Similarity	NPD7946	Pre-registration
0.6744	Remote Similarity	NPD5020	Approved
0.6737	Remote Similarity	NPD3436	Approved
0.6732	Remote Similarity	NPD7069	Discontinued
0.6732	Remote Similarity	NPD8096	Phase 3
0.6732	Remote Similarity	NPD8097	Phase 3
0.6729	Remote Similarity	NPD5801	Clinical (unspecified phase)
0.6727	Remote Similarity	NPD6716	Phase 1
0.6722	Remote Similarity	NPD2214	Approved
0.6722	Remote Similarity	NPD2213	Approved
0.672	Remote Similarity	NPD1783	Clinical (unspecified phase)
0.6718	Remote Similarity	NPD4529	Approved
0.6718	Remote Similarity	NPD4528	Approved
0.6718	Remote Similarity	NPD4526	Approved
0.6717	Remote Similarity	NPD2778	Approved
0.6714	Remote Similarity	NPD6292	Clinical (unspecified phase)
0.6712	Remote Similarity	NPD2921	Clinical (unspecified phase)
0.6706	Remote Similarity	NPD1626	Approved
0.6702	Remote Similarity	NPD6227	Discontinued
0.67	Remote Similarity	NPD5721	Clinical (unspecified phase)
0.6699	Remote Similarity	NPD6974	Phase 3
0.6697	Remote Similarity	NPD5805	Approved
0.6696	Remote Similarity	NPD5482	Discontinued
0.6685	Remote Similarity	NPD2511	Approved
0.6684	Remote Similarity	NPD4418	Discontinued
0.6683	Remote Similarity	NPD4396	Clinical (unspecified phase)
0.6683	Remote Similarity	NPD2715	Clinical (unspecified phase)
0.6683	Remote Similarity	NPD6732	Clinical (unspecified phase)
0.6683	Remote Similarity	NPD7470	Discontinued
0.6683	Remote Similarity	NPD7001	Phase 3
0.6667	Remote Similarity	NPD7418	Discontinued
0.6667	Remote Similarity	NPD6665	Discontinued
0.6667	Remote Similarity	NPD4315	Phase 2
0.6667	Remote Similarity	NPD5483	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5513	Phase 2
0.6667	Remote Similarity	NPD2915	Discontinued
0.6667	Remote Similarity	NPD2896	Discontinued
0.6667	Remote Similarity	NPD5898	Approved
0.6667	Remote Similarity	NPD4397	Phase 1
0.6667	Remote Similarity	NPD3263	Phase 3
0.6667	Remote Similarity	NPD7180	Phase 3
0.6667	Remote Similarity	NPD7538	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5897	Approved
0.6667	Remote Similarity	NPD3315	Phase 3
0.6667	Remote Similarity	NPD5899	Approved
0.6652	Remote Similarity	NPD1483	Discontinued
0.6651	Remote Similarity	NPD4429	Discontinued
0.665	Remote Similarity	NPD6722	Clinical (unspecified phase)
0.6649	Remote Similarity	NPD7869	Discontinued
0.6649	Remote Similarity	NPD7474	Suspended
0.6647	Remote Similarity	NPD2569	Approved
0.6647	Remote Similarity	NPD2567	Approved
0.6646	Remote Similarity	NPD9567	Approved
0.6646	Remote Similarity	NPD552	Approved
0.6646	Remote Similarity	NPD553	Approved
0.6636	Remote Similarity	NPD7994	Phase 2
0.6634	Remote Similarity	NPD2721	Clinical (unspecified phase)
0.6634	Remote Similarity	NPD5072	Discontinued
0.6633	Remote Similarity	NPD7000	Clinical (unspecified phase)
0.6633	Remote Similarity	NPD6999	Discontinued
0.6632	Remote Similarity	NPD3178	Discontinued
0.6629	Remote Similarity	NPD6476	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