NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	275.15
Volume:	292.364
LogP:	3.352
LogD:	3.533
LogS:	-3.797
# Rotatable Bonds:	7
TPSA:	47.56
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.812
Synthetic Accessibility Score:	2.288
Fsp3:	0.438
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:	-4.615
MDCK Permeability:	2.77909839496715e-05
Pgp-inhibitor:	0.99
Pgp-substrate:	0.254
Human Intestinal Absorption (HIA):	0.002
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.021

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.416
Plasma Protein Binding (PPB):	96.43097686767578%
Volume Distribution (VD):	1.585
Pgp-substrate:	4.042787075042725%

ADMET: Metabolism

CYP1A2-inhibitor:	0.964
CYP1A2-substrate:	0.313
CYP2C19-inhibitor:	0.968
CYP2C19-substrate:	0.689
CYP2C9-inhibitor:	0.778
CYP2C9-substrate:	0.903
CYP2D6-inhibitor:	0.926
CYP2D6-substrate:	0.875
CYP3A4-inhibitor:	0.938
CYP3A4-substrate:	0.248

ADMET: Excretion

Clearance (CL):	13.697
Half-life (T1/2):	0.55

ADMET: Toxicity

hERG Blockers:	0.172
Human Hepatotoxicity (H-HT):	0.415
Drug-inuced Liver Injury (DILI):	0.032
AMES Toxicity:	0.014
Rat Oral Acute Toxicity:	0.02
Maximum Recommended Daily Dose:	0.652
Skin Sensitization:	0.926
Carcinogencity:	0.827
Eye Corrosion:	0.031
Eye Irritation:	0.532
Respiratory Toxicity:	0.912

Download Data

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

Natural Product: NPC157740

Natural Product ID:	NPC157740
*Common Name:**	4,5-Dihydropiperlonguminine
IUPAC Name:	(E)-5-(1,3-benzodioxol-5-yl)-N-(2-methylpropyl)pent-2-enamide
Synonyms:	5,6-Dihydropiperlonguminine
Standard InCHIKey:	CSGDXLXTJVRNEA-GQCTYLIASA-N
Standard InCHI:	InChI=1S/C16H21NO3/c1-12(2)10-17-16(18)6-4-3-5-13-7-8-14-15(9-13)20-11-19-14/h4,6-9,12H,3,5,10-11H2,1-2H3,(H,17,18)/b6-4+
SMILES:	CC(C)CN=C(/C=C/CCc1ccc2c(c1)OCO2)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL270619
PubChem CID:	12682184
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000296] Benzodioxoles

*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
NPO28928	Piper nigrum	Species	Piperaceae	Eukaryota	n.a.	fruit	n.a.	DOI[10.1016/S0040-4039(01)00209-X]
NPO28928	Piper nigrum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10575373]
NPO10274	Pothomorphe peltata	n.a.	n.a.	n.a.	n.a.	Dominican Republic	n.a.	PMID[11430019]
NPO6544	Carpesium longifolium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[14695795]
NPO28928	Piper nigrum	Species	Piperaceae	Eukaryota	n.a.	leaf	n.a.	PMID[15467205]
NPO28928	Piper nigrum	Species	Piperaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[16808005]
NPO26237	Piper longum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16872768]
NPO3968	Dracontium loretense	Species	Araceae	Eukaryota	corms	Iquitos, Peru	2005-MAY	PMID[19341262]
NPO3968	Dracontium loretense	Species	Araceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19341262]
NPO10666	Verbesina virginica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19485332]
NPO26237	Piper longum	Species	Piperaceae	Eukaryota	fruits	n.a.	n.a.	PMID[20839888]
NPO4251	Photorhabdus luminescens	Species	Morganellaceae	Bacteria	n.a.	n.a.	n.a.	PMID[22909174]
NPO28928	Piper nigrum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23102654]
NPO12125	Pseudomonas stutzeri	Species	Pseudomonadaceae	Bacteria	n.a.	n.a.	n.a.	PMID[23149469]
NPO26237	Piper longum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23434420]
NPO6648	Piper retrofractum	Species	Piperaceae	Eukaryota	Fruits	n.a.	n.a.	PMID[23506561]
NPO6648	Piper retrofractum	Species	Piperaceae	Eukaryota	leaves	n.a.	n.a.	PMID[25127165]
NPO4251	Photorhabdus luminescens	Species	Morganellaceae	Bacteria	n.a.	n.a.	n.a.	PMID[25988621]
NPO28928	Piper nigrum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31103896]
NPO28928	Piper nigrum	Species	Piperaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO28928	Piper nigrum	Species	Piperaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO28928	Piper nigrum	Species	Piperaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO26237	Piper longum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28928	Piper nigrum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7158	Schefflera venulosa	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO6544	Carpesium longifolium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28928	Piper nigrum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27487	Silene banksia	Species	Caryophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12383	Frullania brasiliensis	Species	Frullaniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7158	Schefflera venulosa	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26237	Piper longum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6648	Piper retrofractum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6544	Carpesium longifolium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26237	Piper longum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO28928	Piper nigrum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO26237	Piper longum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO12125	Pseudomonas stutzeri	Species	Pseudomonadaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO6648	Piper retrofractum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12383	Frullania brasiliensis	Species	Frullaniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13059	Abies webbiana	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6428	Euphorbia wangii	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10666	Verbesina virginica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8639	Agaricus xanthodermus	Species	Agaricaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28928	Piper nigrum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7536	Mycoplasma mycoides	Species	Mycoplasmataceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO27487	Silene banksia	Species	Caryophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2840	Podocarpus minor	Species	Podocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4251	Photorhabdus luminescens	Species	Morganellaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO10459	Brickellia longifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3968	Dracontium loretense	Species	Araceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11137	Dichotomanthes tristaniicarpa	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO964	Homalium laurifolium	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9950	Coelogyne nitida	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10274	Pothomorphe peltata	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO9166	Monascus rubropunctatus	Species	Fellodistomidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO230	Palisota barteri	Species	Commelinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO876	Didymosphaeria enalia	Species	Didymosphaeriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11511	Cochlearia officinalis	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7158	Schefflera venulosa	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO43	Leifsonia aquatica	Species	Microbacteriaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO12488	Bupleurum rigidum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23642	Penicillium tardum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6880	Crocus corsicus	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6544	Carpesium longifolium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26237	Piper longum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2393	Matsumurella chinensis	Species	Lamiaceae	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	1
LD50	1
Others	17

Activity Type	# Activity
Cell Line	13
Organism	2
Others	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT993	Cell Line	Hepatocyte	Mus musculus	Inhibition	=	34.0	%	PMID[450486]
NPT993	Cell Line	Hepatocyte	Mus musculus	Inhibition	=	43.0	%	PMID[450486]
NPT993	Cell Line	Hepatocyte	Mus musculus	Inhibition	=	66.0	%	PMID[450486]
NPT993	Cell Line	Hepatocyte	Mus musculus	Inhibition	=	-4.0	%	PMID[450487]
NPT993	Cell Line	Hepatocyte	Mus musculus	Inhibition	=	5.0	%	PMID[450487]
NPT993	Cell Line	Hepatocyte	Mus musculus	Inhibition	=	7.0	%	PMID[450487]
NPT993	Cell Line	Hepatocyte	Mus musculus	Inhibition	=	43.0	%	PMID[450487]
NPT993	Cell Line	Hepatocyte	Mus musculus	Inhibition	=	66.0	%	PMID[450487]
NPT993	Cell Line	Hepatocyte	Mus musculus	Inhibition	=	34.0	%	PMID[450487]
NPT993	Cell Line	Hepatocyte	Mus musculus	Inhibition	=	15.0	%	PMID[450487]
NPT993	Cell Line	Hepatocyte	Mus musculus	IC50	=	8200.0	nM	PMID[450487]
NPT2	Others	Unspecified		Inhibition	=	25.0	%	PMID[450487]
NPT2	Others	Unspecified		Inhibition	=	-1.0	%	PMID[450487]
NPT2	Others	Unspecified		Inhibition	=	-4.0	%	PMID[450487]
NPT2	Others	Unspecified		Inhibition	=	-13.0	%	PMID[450487]
NPT4776	Organism	Diatraea saccharalis	Diatraea saccharalis	LD90	=	176.5	ug	PMID[450489]
NPT4776	Organism	Diatraea saccharalis	Diatraea saccharalis	LD50	=	92.83	ug	PMID[450489]

☑ 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 NPC157740 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	161
0.1-0.2	1390
0.2-0.3	6199
0.3-0.4	12754
0.4-0.5	5410
0.5-0.6	10961
0.6-0.7	4684
0.7-0.8	1058
0.8-0.85	53
0.85-0.9	6
0.9-0.95	5
0.95-1	16

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC99798
0.9917	High Similarity	NPC156944
0.9917	High Similarity	NPC147247
0.9917	High Similarity	NPC246974
0.9835	High Similarity	NPC291449
0.9835	High Similarity	NPC41331
0.9833	High Similarity	NPC207541
0.9833	High Similarity	NPC152186
0.9833	High Similarity	NPC182147
0.9833	High Similarity	NPC246133
0.9833	High Similarity	NPC71105
0.9833	High Similarity	NPC170583
0.9752	High Similarity	NPC251466
0.975	High Similarity	NPC300955
0.9672	High Similarity	NPC191302
0.9206	High Similarity	NPC470706
0.9127	High Similarity	NPC469977
0.907	High Similarity	NPC282477
0.907	High Similarity	NPC473463
0.907	High Similarity	NPC284855
0.8819	High Similarity	NPC301713
0.8806	High Similarity	NPC275150
0.875	High Similarity	NPC153990
0.8722	High Similarity	NPC254610
0.8583	High Similarity	NPC166837
0.8583	High Similarity	NPC249788
0.8551	High Similarity	NPC327623
0.8538	High Similarity	NPC155838
0.85	High Similarity	NPC31279
0.8485	Intermediate Similarity	NPC214869
0.8473	Intermediate Similarity	NPC195749
0.8473	Intermediate Similarity	NPC52029
0.8473	Intermediate Similarity	NPC35961
0.8462	Intermediate Similarity	NPC186898
0.8451	Intermediate Similarity	NPC474560
0.8417	Intermediate Similarity	NPC127326
0.8413	Intermediate Similarity	NPC344161
0.8409	Intermediate Similarity	NPC114102
0.8385	Intermediate Similarity	NPC274356
0.8358	Intermediate Similarity	NPC218530
0.8346	Intermediate Similarity	NPC93882
0.8346	Intermediate Similarity	NPC130595
0.8321	Intermediate Similarity	NPC77572
0.8321	Intermediate Similarity	NPC251571
0.8284	Intermediate Similarity	NPC6854
0.8284	Intermediate Similarity	NPC313737
0.8284	Intermediate Similarity	NPC285078
0.8281	Intermediate Similarity	NPC80241
0.8281	Intermediate Similarity	NPC301641
0.8271	Intermediate Similarity	NPC255550
0.8271	Intermediate Similarity	NPC308885
0.8175	Intermediate Similarity	NPC14600
0.8175	Intermediate Similarity	NPC204848
0.8175	Intermediate Similarity	NPC160607
0.8175	Intermediate Similarity	NPC41473
0.8175	Intermediate Similarity	NPC312770
0.8134	Intermediate Similarity	NPC275950
0.8116	Intermediate Similarity	NPC299583
0.8106	Intermediate Similarity	NPC40352
0.8106	Intermediate Similarity	NPC213711
0.8074	Intermediate Similarity	NPC476345
0.8062	Intermediate Similarity	NPC183262
0.8049	Intermediate Similarity	NPC137685
0.8047	Intermediate Similarity	NPC57501
0.8047	Intermediate Similarity	NPC69670
0.8047	Intermediate Similarity	NPC119949
0.803	Intermediate Similarity	NPC17348
0.8016	Intermediate Similarity	NPC303370
0.8015	Intermediate Similarity	NPC471505
0.8015	Intermediate Similarity	NPC104077
0.8015	Intermediate Similarity	NPC219671
0.8015	Intermediate Similarity	NPC106739
0.8015	Intermediate Similarity	NPC147616
0.8015	Intermediate Similarity	NPC227002
0.8015	Intermediate Similarity	NPC259742
0.8	Intermediate Similarity	NPC173308
0.8	Intermediate Similarity	NPC292792
0.8	Intermediate Similarity	NPC114845
0.8	Intermediate Similarity	NPC63574
0.8	Intermediate Similarity	NPC181079
0.7986	Intermediate Similarity	NPC296898
0.7984	Intermediate Similarity	NPC173746
0.7984	Intermediate Similarity	NPC257124
0.7984	Intermediate Similarity	NPC156840
0.7984	Intermediate Similarity	NPC8547
0.7971	Intermediate Similarity	NPC145446
0.7971	Intermediate Similarity	NPC137172
0.7956	Intermediate Similarity	NPC169973
0.7951	Intermediate Similarity	NPC227894
0.7941	Intermediate Similarity	NPC318862
0.792	Intermediate Similarity	NPC165646
0.7914	Intermediate Similarity	NPC95366
0.7914	Intermediate Similarity	NPC252107
0.7914	Intermediate Similarity	NPC470707
0.7914	Intermediate Similarity	NPC248505
0.791	Intermediate Similarity	NPC64948
0.791	Intermediate Similarity	NPC177167
0.791	Intermediate Similarity	NPC158737
0.7907	Intermediate Similarity	NPC43275
0.7907	Intermediate Similarity	NPC310338
0.7907	Intermediate Similarity	NPC281298
0.7899	Intermediate Similarity	NPC96406
0.7891	Intermediate Similarity	NPC212643
0.7891	Intermediate Similarity	NPC164386
0.7891	Intermediate Similarity	NPC120075
0.7891	Intermediate Similarity	NPC33271
0.7891	Intermediate Similarity	NPC199209
0.7883	Intermediate Similarity	NPC97316
0.7879	Intermediate Similarity	NPC13020
0.7879	Intermediate Similarity	NPC140359
0.7879	Intermediate Similarity	NPC31344
0.7879	Intermediate Similarity	NPC317769
0.7868	Intermediate Similarity	NPC184814
0.7868	Intermediate Similarity	NPC171550
0.7868	Intermediate Similarity	NPC134764
0.7857	Intermediate Similarity	NPC165106
0.7852	Intermediate Similarity	NPC158471
0.7852	Intermediate Similarity	NPC165128
0.7852	Intermediate Similarity	NPC226862
0.7852	Intermediate Similarity	NPC57119
0.7846	Intermediate Similarity	NPC289330
0.7846	Intermediate Similarity	NPC242885
0.7846	Intermediate Similarity	NPC117780
0.7846	Intermediate Similarity	NPC227217
0.7846	Intermediate Similarity	NPC263835
0.7846	Intermediate Similarity	NPC471308
0.7846	Intermediate Similarity	NPC95614
0.7846	Intermediate Similarity	NPC56214
0.7846	Intermediate Similarity	NPC17388
0.7846	Intermediate Similarity	NPC53596
0.7846	Intermediate Similarity	NPC160120
0.7846	Intermediate Similarity	NPC165133
0.7846	Intermediate Similarity	NPC232316
0.7842	Intermediate Similarity	NPC99078
0.7842	Intermediate Similarity	NPC184938
0.7842	Intermediate Similarity	NPC101624
0.7842	Intermediate Similarity	NPC174191
0.7842	Intermediate Similarity	NPC142547
0.7842	Intermediate Similarity	NPC135777
0.784	Intermediate Similarity	NPC55300
0.7836	Intermediate Similarity	NPC473960
0.7833	Intermediate Similarity	NPC310905
0.7833	Intermediate Similarity	NPC12714
0.7829	Intermediate Similarity	NPC470626
0.7829	Intermediate Similarity	NPC474040
0.7826	Intermediate Similarity	NPC193673
0.7826	Intermediate Similarity	NPC103947
0.7826	Intermediate Similarity	NPC94280
0.7826	Intermediate Similarity	NPC471391
0.7826	Intermediate Similarity	NPC159150
0.7826	Intermediate Similarity	NPC471390
0.7826	Intermediate Similarity	NPC328419
0.7826	Intermediate Similarity	NPC196937
0.7826	Intermediate Similarity	NPC45783
0.7823	Intermediate Similarity	NPC246358
0.7823	Intermediate Similarity	NPC36108
0.7823	Intermediate Similarity	NPC7097
0.7823	Intermediate Similarity	NPC233731
0.7812	Intermediate Similarity	NPC111225
0.7803	Intermediate Similarity	NPC298486
0.7803	Intermediate Similarity	NPC256167
0.7794	Intermediate Similarity	NPC470633
0.7794	Intermediate Similarity	NPC476748
0.7794	Intermediate Similarity	NPC228769
0.7786	Intermediate Similarity	NPC194359
0.7786	Intermediate Similarity	NPC83279
0.7786	Intermediate Similarity	NPC28641
0.7786	Intermediate Similarity	NPC193528
0.7786	Intermediate Similarity	NPC225745
0.7786	Intermediate Similarity	NPC220923
0.7778	Intermediate Similarity	NPC5462
0.7778	Intermediate Similarity	NPC100129
0.777	Intermediate Similarity	NPC180647
0.777	Intermediate Similarity	NPC251454
0.777	Intermediate Similarity	NPC255817
0.777	Intermediate Similarity	NPC205178
0.777	Intermediate Similarity	NPC470881
0.777	Intermediate Similarity	NPC264956
0.777	Intermediate Similarity	NPC136330
0.777	Intermediate Similarity	NPC230698
0.777	Intermediate Similarity	NPC196609
0.777	Intermediate Similarity	NPC73883
0.777	Intermediate Similarity	NPC277042
0.7769	Intermediate Similarity	NPC24474
0.7769	Intermediate Similarity	NPC311595
0.7769	Intermediate Similarity	NPC256369
0.7761	Intermediate Similarity	NPC85830
0.7752	Intermediate Similarity	NPC293619
0.7746	Intermediate Similarity	NPC195814
0.7744	Intermediate Similarity	NPC211218
0.7737	Intermediate Similarity	NPC477694
0.7737	Intermediate Similarity	NPC233224
0.7737	Intermediate Similarity	NPC477705
0.7737	Intermediate Similarity	NPC271208
0.7734	Intermediate Similarity	NPC47194
0.7734	Intermediate Similarity	NPC473264
0.7734	Intermediate Similarity	NPC475815
0.7727	Intermediate Similarity	NPC38996
0.7727	Intermediate Similarity	NPC160380
0.7714	Intermediate Similarity	NPC7018

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 NPC157740 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	132
0.1-0.2	791
0.2-0.3	1305
0.3-0.4	2512
0.4-0.5	2362
0.5-0.6	1353
0.6-0.7	602
0.7-0.8	85
0.8-0.85	8
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8346	Intermediate Similarity	NPD2674	Phase 3
0.8333	Intermediate Similarity	NPD1357	Approved
0.8271	Intermediate Similarity	NPD3145	Approved
0.8271	Intermediate Similarity	NPD3144	Approved
0.8116	Intermediate Similarity	NPD2161	Phase 2
0.8074	Intermediate Similarity	NPD554	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD3705	Approved
0.7984	Intermediate Similarity	NPD228	Approved
0.7973	Intermediate Similarity	NPD5563	Clinical (unspecified phase)
0.7955	Intermediate Similarity	NPD2922	Phase 1
0.7941	Intermediate Similarity	NPD1726	Clinical (unspecified phase)
0.7929	Intermediate Similarity	NPD1375	Discontinued
0.7917	Intermediate Similarity	NPD4739	Approved
0.7914	Intermediate Similarity	NPD4108	Discontinued
0.7887	Intermediate Similarity	NPD6331	Phase 2
0.7857	Intermediate Similarity	NPD5283	Phase 1
0.7785	Intermediate Similarity	NPD7945	Clinical (unspecified phase)
0.777	Intermediate Similarity	NPD2492	Phase 1
0.7746	Intermediate Similarity	NPD7153	Discontinued
0.7744	Intermediate Similarity	NPD1669	Approved
0.7744	Intermediate Similarity	NPD3685	Discontinued
0.7744	Intermediate Similarity	NPD3676	Clinical (unspecified phase)
0.7737	Intermediate Similarity	NPD5110	Phase 2
0.7737	Intermediate Similarity	NPD5111	Phase 2
0.7737	Intermediate Similarity	NPD5109	Approved
0.7708	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD5604	Discontinued
0.7647	Intermediate Similarity	NPD1712	Approved
0.7643	Intermediate Similarity	NPD2157	Approved
0.7597	Intermediate Similarity	NPD709	Approved
0.7594	Intermediate Similarity	NPD776	Approved
0.7591	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7536	Intermediate Similarity	NPD2669	Clinical (unspecified phase)
0.7534	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.7517	Intermediate Similarity	NPD6658	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD2977	Approved
0.75	Intermediate Similarity	NPD2978	Approved
0.75	Intermediate Similarity	NPD7526	Approved
0.75	Intermediate Similarity	NPD7527	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD52	Approved
0.75	Intermediate Similarity	NPD821	Approved
0.7482	Intermediate Similarity	NPD5718	Phase 2
0.7466	Intermediate Similarity	NPD2219	Phase 1
0.7448	Intermediate Similarity	NPD4237	Approved
0.7448	Intermediate Similarity	NPD4236	Phase 3
0.7444	Intermediate Similarity	NPD2667	Approved
0.7444	Intermediate Similarity	NPD2668	Approved
0.7432	Intermediate Similarity	NPD4123	Phase 3
0.7407	Intermediate Similarity	NPD2233	Approved
0.7407	Intermediate Similarity	NPD2232	Approved
0.7407	Intermediate Similarity	NPD2230	Approved
0.7394	Intermediate Similarity	NPD2653	Approved
0.7386	Intermediate Similarity	NPD5773	Approved
0.7386	Intermediate Similarity	NPD5772	Approved
0.7383	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.7376	Intermediate Similarity	NPD1558	Phase 1
0.7355	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7343	Intermediate Similarity	NPD6896	Approved
0.7343	Intermediate Similarity	NPD6895	Approved
0.7333	Intermediate Similarity	NPD2122	Discontinued
0.7329	Intermediate Similarity	NPD3060	Approved
0.7323	Intermediate Similarity	NPD2684	Approved
0.7319	Intermediate Similarity	NPD6584	Phase 3
0.7292	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD1772	Clinical (unspecified phase)
0.726	Intermediate Similarity	NPD1044	Clinical (unspecified phase)
0.7254	Intermediate Similarity	NPD5837	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD4357	Discontinued
0.723	Intermediate Similarity	NPD5241	Discontinued
0.7226	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD6111	Discontinued
0.7218	Intermediate Similarity	NPD5536	Phase 2
0.7211	Intermediate Similarity	NPD5177	Phase 3
0.7211	Intermediate Similarity	NPD4162	Approved
0.72	Intermediate Similarity	NPD1771	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD4678	Approved
0.719	Intermediate Similarity	NPD4675	Approved
0.7183	Intermediate Similarity	NPD839	Approved
0.7183	Intermediate Similarity	NPD840	Approved
0.7163	Intermediate Similarity	NPD3027	Phase 3
0.7163	Intermediate Similarity	NPD1024	Discontinued
0.7162	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7162	Intermediate Similarity	NPD4110	Phase 3
0.7153	Intermediate Similarity	NPD2231	Phase 2
0.7153	Intermediate Similarity	NPD4097	Suspended
0.7153	Intermediate Similarity	NPD2235	Phase 2
0.7143	Intermediate Similarity	NPD1372	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD4993	Discontinued
0.7143	Intermediate Similarity	NPD2808	Discontinued
0.7143	Intermediate Similarity	NPD2040	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD3620	Phase 2
0.7124	Intermediate Similarity	NPD4005	Discontinued
0.7115	Intermediate Similarity	NPD2358	Clinical (unspecified phase)
0.7113	Intermediate Similarity	NPD1048	Approved
0.7101	Intermediate Similarity	NPD6582	Phase 2
0.7101	Intermediate Similarity	NPD6583	Phase 3
0.7099	Intermediate Similarity	NPD7843	Approved
0.7083	Intermediate Similarity	NPD7243	Clinical (unspecified phase)
0.7068	Intermediate Similarity	NPD7157	Approved
0.7063	Intermediate Similarity	NPD1423	Approved
0.7059	Intermediate Similarity	NPD4626	Approved
0.7059	Intermediate Similarity	NPD3686	Approved
0.7059	Intermediate Similarity	NPD4210	Discontinued
0.7059	Intermediate Similarity	NPD3687	Approved
0.7042	Intermediate Similarity	NPD3165	Approved
0.7042	Intermediate Similarity	NPD3164	Approved
0.7042	Intermediate Similarity	NPD3167	Approved
0.7042	Intermediate Similarity	NPD3166	Approved
0.7034	Intermediate Similarity	NPD4579	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD5089	Approved
0.7032	Intermediate Similarity	NPD5090	Approved
0.7027	Intermediate Similarity	NPD4664	Clinical (unspecified phase)
0.7015	Intermediate Similarity	NPD3596	Phase 2
0.7014	Intermediate Similarity	NPD2238	Phase 2
0.7013	Intermediate Similarity	NPD3111	Phase 1
0.7	Intermediate Similarity	NPD1819	Approved
0.7	Intermediate Similarity	NPD3021	Approved
0.7	Intermediate Similarity	NPD1818	Approved
0.7	Intermediate Similarity	NPD3022	Approved
0.7	Intermediate Similarity	NPD1820	Approved
0.7	Intermediate Similarity	NPD1817	Approved
0.6993	Remote Similarity	NPD1039	Discontinued
0.6978	Remote Similarity	NPD2983	Phase 2
0.6978	Remote Similarity	NPD2982	Phase 2
0.697	Remote Similarity	NPD9379	Approved
0.697	Remote Similarity	NPD9377	Approved
0.6968	Remote Similarity	NPD1642	Discontinued
0.6968	Remote Similarity	NPD7028	Phase 2
0.6959	Remote Similarity	NPD3656	Approved
0.6954	Remote Similarity	NPD7124	Phase 2
0.6944	Remote Similarity	NPD3058	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD4055	Discovery
0.6914	Remote Similarity	NPD4083	Discontinued
0.6913	Remote Similarity	NPD7037	Approved
0.6912	Remote Similarity	NPD6581	Approved
0.6912	Remote Similarity	NPD6580	Approved
0.6912	Remote Similarity	NPD1182	Approved
0.6906	Remote Similarity	NPD2337	Clinical (unspecified phase)
0.6906	Remote Similarity	NPD2981	Phase 2
0.6901	Remote Similarity	NPD3018	Phase 2
0.6899	Remote Similarity	NPD1444	Approved
0.6899	Remote Similarity	NPD2563	Approved
0.6899	Remote Similarity	NPD1445	Approved
0.6899	Remote Similarity	NPD3134	Approved
0.6899	Remote Similarity	NPD2560	Approved
0.6884	Remote Similarity	NPD3847	Discontinued
0.6879	Remote Similarity	NPD37	Approved
0.6879	Remote Similarity	NPD5722	Discontinued
0.6871	Remote Similarity	NPD7119	Phase 2
0.687	Remote Similarity	NPD556	Approved
0.6863	Remote Similarity	NPD3688	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD1754	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD3146	Approved
0.6861	Remote Similarity	NPD6830	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6849	Remote Similarity	NPD3657	Discovery
0.6846	Remote Similarity	NPD1358	Approved
0.6842	Remote Similarity	NPD3408	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD1138	Approved
0.6832	Remote Similarity	NPD2644	Approved
0.6832	Remote Similarity	NPD7201	Clinical (unspecified phase)
0.6831	Remote Similarity	NPD558	Phase 2
0.6829	Remote Similarity	NPD5602	Clinical (unspecified phase)
0.6828	Remote Similarity	NPD3162	Approved
0.6828	Remote Similarity	NPD3532	Approved
0.6828	Remote Similarity	NPD3531	Approved
0.6828	Remote Similarity	NPD3530	Approved
0.6828	Remote Similarity	NPD3163	Approved
0.6828	Remote Similarity	NPD7477	Discontinued
0.6818	Remote Similarity	NPD1349	Approved
0.6818	Remote Similarity	NPD1351	Approved
0.6818	Remote Similarity	NPD9280	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD1350	Approved
0.6818	Remote Similarity	NPD3647	Clinical (unspecified phase)
0.6815	Remote Similarity	NPD2557	Approved
0.6815	Remote Similarity	NPD6387	Discontinued
0.6815	Remote Similarity	NPD6671	Approved
0.6813	Remote Similarity	NPD7831	Phase 2
0.6813	Remote Similarity	NPD7832	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD7833	Phase 2
0.6812	Remote Similarity	NPD2423	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD7258	Clinical (unspecified phase)
0.6806	Remote Similarity	NPD3179	Approved
0.6806	Remote Similarity	NPD3180	Approved
0.6806	Remote Similarity	NPD5163	Phase 2
0.68	Remote Similarity	NPD4149	Clinical (unspecified phase)
0.68	Remote Similarity	NPD3655	Clinical (unspecified phase)
0.6797	Remote Similarity	NPD5297	Approved
0.6791	Remote Similarity	NPD2234	Approved
0.6791	Remote Similarity	NPD2228	Approved
0.6791	Remote Similarity	NPD2229	Approved
0.679	Remote Similarity	NPD2821	Approved
0.6786	Remote Similarity	NPD1840	Phase 2
0.6783	Remote Similarity	NPD2250	Discontinued
0.6783	Remote Similarity	NPD2237	Approved
0.6783	Remote Similarity	NPD9494	Approved
0.6781	Remote Similarity	NPD4060	Phase 1

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data