NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	244.12
Volume:	251.423
LogP:	1.335
LogD:	1.316
LogS:	-1.831
# Rotatable Bonds:	2
TPSA:	49.41
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.833
Synthetic Accessibility Score:	2.72
Fsp3:	0.429
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-4.694
MDCK Permeability:	5.26965523022227e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.018
20% Bioavailability (F20%):	0.065
30% Bioavailability (F30%):	0.05

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.701
Plasma Protein Binding (PPB):	47.9635009765625%
Volume Distribution (VD):	0.577
Pgp-substrate:	44.414371490478516%

ADMET: Metabolism

CYP1A2-inhibitor:	0.037
CYP1A2-substrate:	0.121
CYP2C19-inhibitor:	0.338
CYP2C19-substrate:	0.496
CYP2C9-inhibitor:	0.086
CYP2C9-substrate:	0.75
CYP2D6-inhibitor:	0.011
CYP2D6-substrate:	0.446
CYP3A4-inhibitor:	0.174
CYP3A4-substrate:	0.283

ADMET: Excretion

Clearance (CL):	6.155
Half-life (T1/2):	0.74

ADMET: Toxicity

hERG Blockers:	0.019
Human Hepatotoxicity (H-HT):	0.751
Drug-inuced Liver Injury (DILI):	0.187
AMES Toxicity:	0.016
Rat Oral Acute Toxicity:	0.726
Maximum Recommended Daily Dose:	0.316
Skin Sensitization:	0.214
Carcinogencity:	0.133
Eye Corrosion:	0.003
Eye Irritation:	0.018
Respiratory Toxicity:	0.041

Download Data

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

Natural Product: NPC285926

Natural Product ID:	NPC285926
*Common Name:**	(3S,8As)-3-Benzyl-2,3,6,7,8,8A-Hexahydropyrrolo[1,2-A]Pyrazine-1,4-Dione
IUPAC Name:	(3S,8aS)-3-benzyl-2,3,6,7,8,8a-hexahydropyrrolo[1,2-a]pyrazine-1,4-dione
Synonyms:
Standard InCHIKey:	QZBUWPVZSXDWSB-RYUDHWBXSA-N
Standard InCHI:	InChI=1S/C14H16N2O2/c17-13-12-7-4-8-16(12)14(18)11(15-13)9-10-5-2-1-3-6-10/h1-3,5-6,11-12H,4,7-9H2,(H,15,17)/t11-,12-/m0/s1
SMILES:	c1ccc(cc1)C[C@H]1C(=O)N2CCC[C@H]2C(=N1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL512845
PubChem CID:	443440
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:0000347] Amino acids and derivatives [CHEMONTID:0000060] Alpha amino acids and derivatives

*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
NPO30270	Cordyceps sinensis	Species	Cordycipitaceae	Eukaryota	n.a.	mycelium	n.a.	PMID[10423860]
NPO21926	Pseudomonas aeruginosa	Species	Pseudomonadaceae	Bacteria	n.a.	n.a.	n.a.	PMID[10556916]
NPO33070	Callyspongia sp.	Species	n.a.	n.a.	n.a.	red sea	n.a.	PMID[12762806]
NPO1520	Callyspongia pseudoreticulata	Species	Callyspongiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[12828480]
NPO24252	Uvaria hamiltonii	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[14552774]
NPO11713	Hypericum scabrum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15568778]
NPO11713	Hypericum scabrum	Species	Hypericaceae	Eukaryota	n.a.	Uzbekistan	n.a.	PMID[15568778]
NPO30270	Cordyceps sinensis	Species	Cordycipitaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15863936]
NPO33070	Callyspongia sp.	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[18027906]
NPO21926	Pseudomonas aeruginosa	Species	Pseudomonadaceae	Bacteria	n.a.	n.a.	n.a.	PMID[19406895]
NPO21926	Pseudomonas aeruginosa	Species	Pseudomonadaceae	Bacteria	n.a.	n.a.	n.a.	PMID[19917748]
NPO21926	Pseudomonas aeruginosa	Species	Pseudomonadaceae	Bacteria	n.a.	n.a.	n.a.	PMID[20932054]
NPO11171	Stelletta clavosa	Species	Ancorinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[21280591]
NPO30270	Cordyceps sinensis	Species	Cordycipitaceae	Eukaryota	n.a.	mycelium	n.a.	PMID[21848266]
NPO30270	Cordyceps sinensis	Species	Cordycipitaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21848266]
NPO16259	Syringa reticulata	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21955940]
NPO33070	Callyspongia sp.	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[22469701]
NPO33070	Callyspongia sp.	Species	n.a.	n.a.	n.a.	collected by hand at a depth of 10 m off the shore of Iriomote Island, Okinawa Prefecture, Japan	2009-JUN	PMID[23855338]
NPO33070	Callyspongia sp.	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[24948562]
NPO21926	Pseudomonas aeruginosa	Species	Pseudomonadaceae	Bacteria	n.a.	n.a.	n.a.	PMID[25043228]
NPO21926	Pseudomonas aeruginosa	Species	Pseudomonadaceae	Bacteria	n.a.	n.a.	n.a.	PMID[25960261]
NPO33070	Callyspongia sp.	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[27015002]
NPO11713	Hypericum scabrum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27280968]
NPO21926	Pseudomonas aeruginosa	Species	Pseudomonadaceae	Bacteria	n.a.	n.a.	n.a.	PMID[32603106]
NPO33070	Callyspongia sp.	Species	n.a.	n.a.	n.a.	New Guinea	n.a.	PMID[8158156]
NPO21926	Pseudomonas aeruginosa	Species	Pseudomonadaceae	Bacteria	n.a.	Antarctic	n.a.	PMID[8882433]
NPO24252	Uvaria hamiltonii	Species	Annonaceae	Eukaryota	leaf and stem	n.a.	n.a.	PMID[9584399]
NPO30270	Cordyceps sinensis	Species	Cordycipitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18739	Exallage chrysotricha	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO30270	Cordyceps sinensis	Species	Cordycipitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO24585	Ocotea macropoda	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6855	Chaenostoma foetidum	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25737	Solanum pimpinellifolium	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7014	Retaster insignis	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO28694	Sanguisorba tenuifolia	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16259	Syringa reticulata	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12904	Nauclea coadunata	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13207	Leptoclinides durus	Species	Didemnidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18739	Exallage chrysotricha	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9400	Mutisia homoeantha	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11713	Hypericum scabrum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11025	Cryptocarya leucophylla	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23819	Baccharis peruviana	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1520	Callyspongia pseudoreticulata	Species	Callyspongiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21926	Pseudomonas aeruginosa	Species	Pseudomonadaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO14193	Pleiococca wilcoxiana	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO6693	Streptomyces triangulatus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO11171	Stelletta clavosa	Species	Ancorinidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24252	Uvaria hamiltonii	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11879	Polistes rothneyi	Species	Vespidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1444	Thalictrum amurense	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23277	Lobophora papenfussii	Species	Dictyotaceae	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
MIC	3
Others	6
Potency	3

Activity Type	# Activity
Cell Line	6
Individual Protein	3
NON-MOLECULAR	2
Organism	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT56	Individual Protein	Beta-lactamase AmpC	Escherichia coli K-12	Potency	=	112201.8	nM	PMID[529879]
NPT71	Cell Line	HEK293	Homo sapiens	Potency	n.a.	35481.3	nM	PMID[529879]
NPT1182	Cell Line	J774.A1	Mus musculus	FC	=	1.54	n.a.	PMID[529881]
NPT1182	Cell Line	J774.A1	Mus musculus	FC	=	1.62	n.a.	PMID[529881]
NPT1182	Cell Line	J774.A1	Mus musculus	FC	=	2.05	n.a.	PMID[529881]
NPT5716	Individual Protein	C-C motif chemokine 2	Homo sapiens	Inhibition	=	50.0	%	PMID[529882]
NPT113	Cell Line	RAW264.7	Mus musculus	Inhibition	=	45.0	%	PMID[529884]
NPT113	Cell Line	RAW264.7	Mus musculus	Inhibition	=	3.0	%	PMID[529884]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	12.83	ug.mL-1	PMID[529880]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	10.37	ug.mL-1	PMID[529880]
NPT8	Individual Protein	DNA polymerase iota	Homo sapiens	Potency	n.a.	89125.1	nM	PMID[529879]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	15.1	ug.mL-1	PMID[529883]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	=	17.2	ug.mL-1	PMID[529883]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	20.0	ug.mL-1	PMID[529883]

☑ 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 NPC285926 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	146
0.1-0.2	1294
0.2-0.3	8785
0.3-0.4	20407
0.4-0.5	9282
0.5-0.6	2036
0.6-0.7	489
0.7-0.8	211
0.8-0.85	34
0.85-0.9	7
0.9-0.95	3
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC315276
1.0	High Similarity	NPC14672
0.9391	High Similarity	NPC474082
0.9391	High Similarity	NPC175726
0.913	High Similarity	NPC200964
0.8938	High Similarity	NPC33742
0.8618	High Similarity	NPC200589
0.8583	High Similarity	NPC6975
0.8548	High Similarity	NPC255447
0.8438	Intermediate Similarity	NPC313694
0.8438	Intermediate Similarity	NPC242159
0.8417	Intermediate Similarity	NPC202521
0.839	Intermediate Similarity	NPC470545
0.8387	Intermediate Similarity	NPC473322
0.8362	Intermediate Similarity	NPC35850
0.8362	Intermediate Similarity	NPC276949
0.8333	Intermediate Similarity	NPC476990
0.8319	Intermediate Similarity	NPC470546
0.8305	Intermediate Similarity	NPC470544
0.824	Intermediate Similarity	NPC111428
0.8203	Intermediate Similarity	NPC248283
0.8197	Intermediate Similarity	NPC252878
0.8167	Intermediate Similarity	NPC220698
0.813	Intermediate Similarity	NPC46427
0.8115	Intermediate Similarity	NPC71684
0.811	Intermediate Similarity	NPC130309
0.8031	Intermediate Similarity	NPC300315
0.8015	Intermediate Similarity	NPC178662
0.8015	Intermediate Similarity	NPC476133
0.8015	Intermediate Similarity	NPC470884
0.8015	Intermediate Similarity	NPC92784
0.8015	Intermediate Similarity	NPC98424
0.8	Intermediate Similarity	NPC101719
0.8	Intermediate Similarity	NPC239357
0.7985	Intermediate Similarity	NPC471680
0.792	Intermediate Similarity	NPC222466
0.7852	Intermediate Similarity	NPC209509
0.7846	Intermediate Similarity	NPC287401
0.7803	Intermediate Similarity	NPC471265
0.7803	Intermediate Similarity	NPC471264
0.7794	Intermediate Similarity	NPC262077
0.7778	Intermediate Similarity	NPC52748
0.7778	Intermediate Similarity	NPC476978
0.7744	Intermediate Similarity	NPC89489
0.7737	Intermediate Similarity	NPC16188
0.7721	Intermediate Similarity	NPC5620
0.7704	Intermediate Similarity	NPC161069
0.7679	Intermediate Similarity	NPC472258
0.7672	Intermediate Similarity	NPC473418
0.7652	Intermediate Similarity	NPC141050
0.763	Intermediate Similarity	NPC269398
0.763	Intermediate Similarity	NPC263493
0.7607	Intermediate Similarity	NPC45033
0.76	Intermediate Similarity	NPC27833
0.7554	Intermediate Similarity	NPC471820
0.7554	Intermediate Similarity	NPC471821
0.7545	Intermediate Similarity	NPC226438
0.7544	Intermediate Similarity	NPC12730
0.7538	Intermediate Similarity	NPC469666
0.7518	Intermediate Similarity	NPC314388
0.7518	Intermediate Similarity	NPC315283
0.75	Intermediate Similarity	NPC303045
0.75	Intermediate Similarity	NPC164859
0.75	Intermediate Similarity	NPC129666
0.75	Intermediate Similarity	NPC22746
0.75	Intermediate Similarity	NPC161972
0.75	Intermediate Similarity	NPC319579
0.75	Intermediate Similarity	NPC283783
0.75	Intermediate Similarity	NPC2501
0.7482	Intermediate Similarity	NPC138775
0.7481	Intermediate Similarity	NPC132636
0.7465	Intermediate Similarity	NPC122590
0.7465	Intermediate Similarity	NPC202198
0.7464	Intermediate Similarity	NPC322878
0.7464	Intermediate Similarity	NPC315266
0.7464	Intermediate Similarity	NPC313867
0.7464	Intermediate Similarity	NPC316008
0.7462	Intermediate Similarity	NPC319766
0.7429	Intermediate Similarity	NPC240848
0.7426	Intermediate Similarity	NPC163392
0.7426	Intermediate Similarity	NPC239762
0.7413	Intermediate Similarity	NPC473002
0.741	Intermediate Similarity	NPC314358
0.7372	Intermediate Similarity	NPC476989
0.7368	Intermediate Similarity	NPC311242
0.7368	Intermediate Similarity	NPC325479
0.7361	Intermediate Similarity	NPC469903
0.7353	Intermediate Similarity	NPC122553
0.7345	Intermediate Similarity	NPC256452
0.7319	Intermediate Similarity	NPC77905
0.7311	Intermediate Similarity	NPC474804
0.7311	Intermediate Similarity	NPC130898
0.7311	Intermediate Similarity	NPC474973
0.7311	Intermediate Similarity	NPC327481
0.7304	Intermediate Similarity	NPC322598
0.7299	Intermediate Similarity	NPC268841
0.7299	Intermediate Similarity	NPC46098
0.7299	Intermediate Similarity	NPC307357
0.7295	Intermediate Similarity	NPC329011
0.7273	Intermediate Similarity	NPC233702
0.7273	Intermediate Similarity	NPC162104
0.7265	Intermediate Similarity	NPC329375
0.7236	Intermediate Similarity	NPC474584
0.7234	Intermediate Similarity	NPC225648
0.7234	Intermediate Similarity	NPC145113
0.7234	Intermediate Similarity	NPC311658
0.7234	Intermediate Similarity	NPC329761
0.7227	Intermediate Similarity	NPC143516
0.7194	Intermediate Similarity	NPC468984
0.7194	Intermediate Similarity	NPC139326
0.7188	Intermediate Similarity	NPC302169
0.7167	Intermediate Similarity	NPC473498
0.7162	Intermediate Similarity	NPC469902
0.7162	Intermediate Similarity	NPC473003
0.7153	Intermediate Similarity	NPC127741
0.7153	Intermediate Similarity	NPC68865
0.7143	Intermediate Similarity	NPC275467
0.7143	Intermediate Similarity	NPC197743
0.7143	Intermediate Similarity	NPC297145
0.7114	Intermediate Similarity	NPC241794
0.7103	Intermediate Similarity	NPC56685
0.7103	Intermediate Similarity	NPC5194
0.7103	Intermediate Similarity	NPC261934
0.7103	Intermediate Similarity	NPC262166
0.7095	Intermediate Similarity	NPC104345
0.7092	Intermediate Similarity	NPC201244
0.7092	Intermediate Similarity	NPC477217
0.7083	Intermediate Similarity	NPC67043
0.7083	Intermediate Similarity	NPC475168
0.7083	Intermediate Similarity	NPC473491
0.7083	Intermediate Similarity	NPC7817
0.708	Intermediate Similarity	NPC79465
0.708	Intermediate Similarity	NPC273907
0.708	Intermediate Similarity	NPC474787
0.708	Intermediate Similarity	NPC474811
0.708	Intermediate Similarity	NPC151706
0.708	Intermediate Similarity	NPC76785
0.708	Intermediate Similarity	NPC260045
0.708	Intermediate Similarity	NPC475598
0.708	Intermediate Similarity	NPC293377
0.708	Intermediate Similarity	NPC9687
0.708	Intermediate Similarity	NPC118099
0.708	Intermediate Similarity	NPC475318
0.708	Intermediate Similarity	NPC476102
0.708	Intermediate Similarity	NPC474855
0.708	Intermediate Similarity	NPC49577
0.708	Intermediate Similarity	NPC90194
0.7071	Intermediate Similarity	NPC197682
0.7063	Intermediate Similarity	NPC197470
0.7063	Intermediate Similarity	NPC105717
0.7059	Intermediate Similarity	NPC471317
0.705	Intermediate Similarity	NPC476259
0.7047	Intermediate Similarity	NPC469901
0.7027	Intermediate Similarity	NPC324850
0.7027	Intermediate Similarity	NPC471638
0.7007	Intermediate Similarity	NPC476268
0.7	Intermediate Similarity	NPC168113
0.7	Intermediate Similarity	NPC68650
0.6993	Remote Similarity	NPC135121
0.6992	Remote Similarity	NPC477937
0.6985	Remote Similarity	NPC246079
0.6983	Remote Similarity	NPC25565
0.6953	Remote Similarity	NPC169328
0.695	Remote Similarity	NPC176226
0.6944	Remote Similarity	NPC9373
0.6939	Remote Similarity	NPC470902
0.6928	Remote Similarity	NPC328649
0.6928	Remote Similarity	NPC141957
0.6923	Remote Similarity	NPC122493
0.6923	Remote Similarity	NPC10781
0.6923	Remote Similarity	NPC473501
0.6923	Remote Similarity	NPC475439
0.6923	Remote Similarity	NPC293628
0.6911	Remote Similarity	NPC473676
0.6899	Remote Similarity	NPC310467
0.6883	Remote Similarity	NPC469904
0.6879	Remote Similarity	NPC469426
0.6879	Remote Similarity	NPC469427
0.6871	Remote Similarity	NPC286551
0.6871	Remote Similarity	NPC473341
0.6867	Remote Similarity	NPC469898
0.6861	Remote Similarity	NPC257390
0.6842	Remote Similarity	NPC316108
0.6814	Remote Similarity	NPC325441
0.681	Remote Similarity	NPC71140
0.6803	Remote Similarity	NPC476198
0.6795	Remote Similarity	NPC89831
0.6791	Remote Similarity	NPC474479
0.6781	Remote Similarity	NPC13470
0.6781	Remote Similarity	NPC254798
0.678	Remote Similarity	NPC324569
0.6779	Remote Similarity	NPC244509
0.6777	Remote Similarity	NPC202613
0.6776	Remote Similarity	NPC73655
0.6774	Remote Similarity	NPC280022
0.6767	Remote Similarity	NPC35996
0.6755	Remote Similarity	NPC244336
0.6753	Remote Similarity	NPC61004
0.6752	Remote Similarity	NPC137627
0.675	Remote Similarity	NPC39822

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 NPC285926 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	127
0.1-0.2	372
0.2-0.3	756
0.3-0.4	2228
0.4-0.5	3640
0.5-0.6	1567
0.6-0.7	364
0.7-0.8	83
0.8-0.85	11
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.876	High Similarity	NPD5339	Clinical (unspecified phase)
0.8583	High Similarity	NPD2584	Suspended
0.8226	Intermediate Similarity	NPD2585	Clinical (unspecified phase)
0.8203	Intermediate Similarity	NPD4791	Clinical (unspecified phase)
0.8175	Intermediate Similarity	NPD4125	Approved
0.814	Intermediate Similarity	NPD7113	Clinical (unspecified phase)
0.8125	Intermediate Similarity	NPD941	Approved
0.8077	Intermediate Similarity	NPD4782	Clinical (unspecified phase)
0.8077	Intermediate Similarity	NPD8173	Phase 2
0.8077	Intermediate Similarity	NPD8172	Phase 2
0.8049	Intermediate Similarity	NPD4761	Approved
0.8049	Intermediate Similarity	NPD4762	Approved
0.8047	Intermediate Similarity	NPD3632	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD2031	Discontinued
0.7984	Intermediate Similarity	NPD3073	Approved
0.7984	Intermediate Similarity	NPD3071	Approved
0.7984	Intermediate Similarity	NPD3072	Approved
0.7982	Intermediate Similarity	NPD999	Phase 2
0.791	Intermediate Similarity	NPD5341	Clinical (unspecified phase)
0.7903	Intermediate Similarity	NPD4706	Clinical (unspecified phase)
0.7852	Intermediate Similarity	NPD6860	Clinical (unspecified phase)
0.7752	Intermediate Similarity	NPD5263	Approved
0.7734	Intermediate Similarity	NPD3604	Clinical (unspecified phase)
0.7734	Intermediate Similarity	NPD3608	Clinical (unspecified phase)
0.7687	Intermediate Similarity	NPD7728	Clinical (unspecified phase)
0.7674	Intermediate Similarity	NPD4175	Approved
0.7674	Intermediate Similarity	NPD4177	Approved
0.7667	Intermediate Similarity	NPD480	Approved
0.7634	Intermediate Similarity	NPD2078	Clinical (unspecified phase)
0.7634	Intermediate Similarity	NPD1330	Phase 2
0.7634	Intermediate Similarity	NPD1329	Clinical (unspecified phase)
0.7615	Intermediate Similarity	NPD4676	Approved
0.7615	Intermediate Similarity	NPD7979	Clinical (unspecified phase)
0.7612	Intermediate Similarity	NPD6901	Phase 3
0.7563	Intermediate Similarity	NPD3581	Discontinued
0.7538	Intermediate Similarity	NPD3626	Phase 3
0.752	Intermediate Similarity	NPD4504	Clinical (unspecified phase)
0.7463	Intermediate Similarity	NPD8643	Discontinued
0.7463	Intermediate Similarity	NPD3908	Approved
0.7444	Intermediate Similarity	NPD3561	Clinical (unspecified phase)
0.7442	Intermediate Similarity	NPD6792	Phase 3
0.7407	Intermediate Similarity	NPD6073	Approved
0.7405	Intermediate Similarity	NPD3040	Approved
0.7405	Intermediate Similarity	NPD5759	Approved
0.7388	Intermediate Similarity	NPD8416	Discontinued
0.7376	Intermediate Similarity	NPD6631	Clinical (unspecified phase)
0.7373	Intermediate Similarity	NPD1018	Approved
0.7364	Intermediate Similarity	NPD4677	Discontinued
0.7355	Intermediate Similarity	NPD3642	Approved
0.7355	Intermediate Similarity	NPD3644	Approved
0.7355	Intermediate Similarity	NPD3643	Approved
0.7328	Intermediate Similarity	NPD4151	Approved
0.7324	Intermediate Similarity	NPD979	Approved
0.7319	Intermediate Similarity	NPD7720	Phase 2
0.7317	Intermediate Similarity	NPD3598	Phase 3
0.7311	Intermediate Similarity	NPD7130	Phase 3
0.7308	Intermediate Similarity	NPD5577	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD5578	Approved
0.7308	Intermediate Similarity	NPD3125	Approved
0.7302	Intermediate Similarity	NPD998	Approved
0.7299	Intermediate Similarity	NPD5301	Clinical (unspecified phase)
0.7293	Intermediate Similarity	NPD2046	Approved
0.7293	Intermediate Similarity	NPD6919	Clinical (unspecified phase)
0.7293	Intermediate Similarity	NPD2044	Approved
0.7293	Intermediate Similarity	NPD2049	Clinical (unspecified phase)
0.7293	Intermediate Similarity	NPD2045	Approved
0.7293	Intermediate Similarity	NPD2050	Clinical (unspecified phase)
0.7293	Intermediate Similarity	NPD2048	Approved
0.7293	Intermediate Similarity	NPD2043	Approved
0.7293	Intermediate Similarity	NPD2051	Approved
0.7293	Intermediate Similarity	NPD21	Approved
0.7293	Intermediate Similarity	NPD2047	Approved
0.7286	Intermediate Similarity	NPD1967	Approved
0.7286	Intermediate Similarity	NPD1968	Approved
0.728	Intermediate Similarity	NPD1344	Phase 2
0.7279	Intermediate Similarity	NPD5725	Approved
0.7234	Intermediate Similarity	NPD8323	Discontinued
0.7226	Intermediate Similarity	NPD4126	Approved
0.7222	Intermediate Similarity	NPD3806	Clinical (unspecified phase)
0.7206	Intermediate Similarity	NPD4757	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD3588	Discontinued
0.7194	Intermediate Similarity	NPD2087	Approved
0.7194	Intermediate Similarity	NPD2088	Approved
0.7194	Intermediate Similarity	NPD8076	Discontinued
0.7194	Intermediate Similarity	NPD2022	Approved
0.7192	Intermediate Similarity	NPD7267	Clinical (unspecified phase)
0.7183	Intermediate Similarity	NPD8290	Clinical (unspecified phase)
0.7165	Intermediate Similarity	NPD6345	Approved
0.7165	Intermediate Similarity	NPD6343	Approved
0.7164	Intermediate Similarity	NPD4794	Discontinued
0.7155	Intermediate Similarity	NPD466	Approved
0.7154	Intermediate Similarity	NPD753	Approved
0.7153	Intermediate Similarity	NPD7613	Discontinued
0.7143	Intermediate Similarity	NPD7118	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD2437	Approved
0.7143	Intermediate Similarity	NPD2436	Approved
0.7132	Intermediate Similarity	NPD4153	Approved
0.712	Intermediate Similarity	NPD3551	Approved
0.712	Intermediate Similarity	NPD747	Discontinued
0.7113	Intermediate Similarity	NPD6552	Clinical (unspecified phase)
0.7113	Intermediate Similarity	NPD7602	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD5581	Approved
0.7111	Intermediate Similarity	NPD5299	Approved
0.7094	Intermediate Similarity	NPD742	Approved
0.7063	Intermediate Similarity	NPD1348	Approved
0.7059	Intermediate Similarity	NPD7634	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD5747	Discontinued
0.7027	Intermediate Similarity	NPD951	Approved
0.7018	Intermediate Similarity	NPD1812	Approved
0.7018	Intermediate Similarity	NPD1814	Approved
0.7014	Intermediate Similarity	NPD5614	Approved
0.7014	Intermediate Similarity	NPD5613	Approved
0.7008	Intermediate Similarity	NPD3123	Discovery
0.7007	Intermediate Similarity	NPD5296	Approved
0.7007	Intermediate Similarity	NPD6623	Phase 3
0.7007	Intermediate Similarity	NPD5323	Approved
0.7	Intermediate Similarity	NPD5187	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD4803	Discontinued
0.6972	Remote Similarity	NPD5265	Approved
0.6972	Remote Similarity	NPD5264	Approved
0.6966	Remote Similarity	NPD4432	Discontinued
0.6957	Remote Similarity	NPD3577	Discontinued
0.6953	Remote Similarity	NPD5991	Approved
0.6953	Remote Similarity	NPD5990	Approved
0.6942	Remote Similarity	NPD1040	Phase 2
0.6935	Remote Similarity	NPD2583	Phase 2
0.6929	Remote Similarity	NPD3480	Approved
0.6923	Remote Similarity	NPD3064	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD9566	Approved
0.6917	Remote Similarity	NPD5367	Discontinued
0.6912	Remote Similarity	NPD4497	Clinical (unspecified phase)
0.6906	Remote Similarity	NPD5004	Approved
0.6897	Remote Similarity	NPD3988	Approved
0.6897	Remote Similarity	NPD3987	Approved
0.6897	Remote Similarity	NPD6088	Approved
0.6897	Remote Similarity	NPD7892	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD6408	Phase 1
0.6879	Remote Similarity	NPD7511	Approved
0.6879	Remote Similarity	NPD6897	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD7512	Approved
0.6867	Remote Similarity	NPD7011	Discontinued
0.6866	Remote Similarity	NPD3029	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD6294	Approved
0.6857	Remote Similarity	NPD6852	Discontinued
0.6857	Remote Similarity	NPD6295	Approved
0.6833	Remote Similarity	NPD6588	Clinical (unspecified phase)
0.6831	Remote Similarity	NPD4152	Approved
0.6824	Remote Similarity	NPD8315	Phase 1
0.6807	Remote Similarity	NPD787	Suspended
0.6803	Remote Similarity	NPD5230	Approved
0.6803	Remote Similarity	NPD6144	Discontinued
0.6803	Remote Similarity	NPD2197	Approved
0.6803	Remote Similarity	NPD5229	Approved
0.6803	Remote Similarity	NPD2192	Approved
0.6794	Remote Similarity	NPD4733	Approved
0.6791	Remote Similarity	NPD6325	Discontinued
0.6781	Remote Similarity	NPD2016	Approved
0.6781	Remote Similarity	NPD2014	Approved
0.6781	Remote Similarity	NPD2013	Approved
0.678	Remote Similarity	NPD1100	Approved
0.678	Remote Similarity	NPD1099	Approved
0.6767	Remote Similarity	NPD5108	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD7131	Phase 3
0.675	Remote Similarity	NPD4760	Clinical (unspecified phase)
0.6744	Remote Similarity	NPD7679	Phase 2
0.6739	Remote Similarity	NPD2846	Clinical (unspecified phase)
0.6724	Remote Similarity	NPD6690	Approved
0.6711	Remote Similarity	NPD4647	Approved
0.6711	Remote Similarity	NPD4646	Approved
0.6711	Remote Similarity	NPD4648	Approved
0.6694	Remote Similarity	NPD6038	Clinical (unspecified phase)
0.6693	Remote Similarity	NPD1764	Approved
0.6693	Remote Similarity	NPD1762	Approved
0.6692	Remote Similarity	NPD2117	Pre-registration
0.6692	Remote Similarity	NPD1948	Approved
0.6692	Remote Similarity	NPD3624	Phase 2
0.6692	Remote Similarity	NPD2116	Approved
0.6692	Remote Similarity	NPD1713	Approved
0.6692	Remote Similarity	NPD2115	Approved
0.6691	Remote Similarity	NPD3578	Clinical (unspecified phase)
0.6691	Remote Similarity	NPD7086	Phase 2
0.6667	Remote Similarity	NPD3282	Phase 1
0.6667	Remote Similarity	NPD1763	Approved
0.6667	Remote Similarity	NPD7510	Approved
0.6667	Remote Similarity	NPD1767	Approved
0.6667	Remote Similarity	NPD1761	Approved
0.6667	Remote Similarity	NPD2634	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1080	Approved
0.6667	Remote Similarity	NPD1766	Approved
0.6667	Remote Similarity	NPD1765	Approved
0.6667	Remote Similarity	NPD1036	Approved
0.6667	Remote Similarity	NPD1581	Approved
0.6667	Remote Similarity	NPD1582	Approved
0.6667	Remote Similarity	NPD3283	Phase 3
0.6667	Remote Similarity	NPD6806	Phase 1
0.6646	Remote Similarity	NPD7965	Phase 2
0.6646	Remote Similarity	NPD7964	Clinical (unspecified phase)
0.6645	Remote Similarity	NPD8303	Discontinued
0.6642	Remote Similarity	NPD1781	Discontinued
0.6641	Remote Similarity	NPD3149	Approved

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