NPASS Compound

Structure

CID252107 OpenBabel06191716052D 21 23 0 0 0 0 0 0 0 0999 V2000 7.0132 -3.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4152 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2812 -0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1472 -2.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8793 -2.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 -0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1472 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1472 -1.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8793 -1.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 -0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5878 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0132 -0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0132 -1.1910 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 7.8793 0.3090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.6180 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 4 1 0 0 0 0 1 5 1 0 0 0 0 2 3 1 0 0 0 0 2 6 1 0 0 0 0 3 7 2 0 0 0 0 4 10 1 0 0 0 0 5 11 1 0 0 0 0 6 14 1 0 0 0 0 7 17 1 0 0 0 0 8 9 2 0 0 0 0 8 14 1 0 0 0 0 9 15 1 0 0 0 0 10 18 1 0 0 0 0 11 18 1 0 0 0 0 12 14 2 0 0 0 0 12 16 1 0 0 0 0 13 20 1 0 0 0 0 13 21 1 0 0 0 0 15 16 2 0 0 0 0 15 20 1 0 0 0 0 16 21 1 0 0 0 0 17 18 1 0 0 0 0 17 19 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	287.15
Volume:	301.104
LogP:	3.419
LogD:	2.931
LogS:	-4.294
# Rotatable Bonds:	5
TPSA:	38.77
# H-Bond Aceptor:	4
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.799
Synthetic Accessibility Score:	2.237
Fsp3:	0.471
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:	-4.69
MDCK Permeability:	3.0008539397385903e-05
Pgp-inhibitor:	0.984
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.001
20% Bioavailability (F20%):	0.439
30% Bioavailability (F30%):	0.036

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.425
Plasma Protein Binding (PPB):	96.03308868408203%
Volume Distribution (VD):	0.592
Pgp-substrate:	4.273948669433594%

ADMET: Metabolism

CYP1A2-inhibitor:	0.974
CYP1A2-substrate:	0.502
CYP2C19-inhibitor:	0.932
CYP2C19-substrate:	0.513
CYP2C9-inhibitor:	0.532
CYP2C9-substrate:	0.727
CYP2D6-inhibitor:	0.956
CYP2D6-substrate:	0.891
CYP3A4-inhibitor:	0.953
CYP3A4-substrate:	0.295

ADMET: Excretion

Clearance (CL):	10.28
Half-life (T1/2):	0.603

ADMET: Toxicity

hERG Blockers:	0.463
Human Hepatotoxicity (H-HT):	0.254
Drug-inuced Liver Injury (DILI):	0.049
AMES Toxicity:	0.004
Rat Oral Acute Toxicity:	0.038
Maximum Recommended Daily Dose:	0.548
Skin Sensitization:	0.959
Carcinogencity:	0.801
Eye Corrosion:	0.149
Eye Irritation:	0.441
Respiratory Toxicity:	0.968

Download Data

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

Natural Product: NPC252107

Natural Product ID:	NPC252107
*Common Name:**	Piperanine
IUPAC Name:	(E)-5-(1,3-benzodioxol-5-yl)-1-piperidin-1-ylpent-2-en-1-one
Synonyms:	Dalpha,Beta-Dihydropiperine; Delata-Alpha,Beta-Dihydropiperine; Piperanine
Standard InCHIKey:	QHWOFMXDKFORMO-XVNBXDOJSA-N
Standard InCHI:	InChI=1S/C17H21NO3/c19-17(18-10-4-1-5-11-18)7-3-2-6-14-8-9-15-16(12-14)21-13-20-15/h3,7-9,12H,1-2,4-6,10-11,13H2/b7-3+
SMILES:	O=C(N1CCCCC1)/C=C/CCc1ccc2c(c1)OCO2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL256218
PubChem CID:	5320618
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]
NPO10906	Pinus koraiensis	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21953622]
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]
NPO10906	Pinus koraiensis	Species	Pinaceae	Eukaryota	Twigs	n.a.	n.a.	PMID[32520551]
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]
NPO28928	Piper nigrum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO6544	Carpesium longifolium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO10906	Pinus koraiensis	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26237	Piper longum	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]
NPO20606	Piper tuberculatum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28928	Piper nigrum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26237	Piper longum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12383	Frullania brasiliensis	Species	Frullaniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10906	Pinus koraiensis	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27487	Silene banksia	Species	Caryophyllaceae	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]
NPO20606	Piper tuberculatum	Species	Piperaceae	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[TCM_Taiwan]
NPO28928	Piper nigrum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO10906	Pinus koraiensis	Species	Pinaceae	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]
NPO10459	Brickellia longifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10666	Verbesina virginica	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]
NPO27487	Silene banksia	Species	Caryophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10906	Pinus koraiensis	Species	Pinaceae	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]
NPO11137	Dichotomanthes tristaniicarpa	Species	Rosaceae	Eukaryota	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]
NPO20606	Piper tuberculatum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7158	Schefflera venulosa	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26237	Piper longum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO43	Leifsonia aquatica	Species	Microbacteriaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO28928	Piper nigrum	Species	Piperaceae	Eukaryota	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]
NPO6544	Carpesium longifolium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6880	Crocus corsicus	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2393	Matsumurella chinensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12125	Pseudomonas stutzeri	Species	Pseudomonadaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO12383	Frullania brasiliensis	Species	Frullaniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6428	Euphorbia wangii	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7536	Mycoplasma mycoides	Species	Mycoplasmataceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO6648	Piper retrofractum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8639	Agaricus xanthodermus	Species	Agaricaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4251	Photorhabdus luminescens	Species	Morganellaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO13059	Abies webbiana	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2840	Podocarpus minor	Species	Podocarpaceae	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
EC50	2
IC50	1
Others	25
Potency	2

Activity Type	# Activity
Cell Line	19
Individual Protein	4
Others	7

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT993	Cell Line	Hepatocyte	Mus musculus	Inhibition	=	31.0	%	PMID[458813]
NPT993	Cell Line	Hepatocyte	Mus musculus	Inhibition	=	50.0	%	PMID[458813]
NPT993	Cell Line	Hepatocyte	Mus musculus	Inhibition	=	53.0	%	PMID[458813]
NPT520	Cell Line	3T3-L1	Mus musculus	Activity	=	20.4	%	PMID[458814]
NPT520	Cell Line	3T3-L1	Mus musculus	Activity	=	19.1	%	PMID[458814]
NPT520	Cell Line	3T3-L1	Mus musculus	Activity	=	13.1	%	PMID[458814]
NPT520	Cell Line	3T3-L1	Mus musculus	Activity	=	8.3	%	PMID[458814]
NPT1460	Cell Line	L929	Mus musculus	Inhibition	=	2.0	%	PMID[458815]
NPT1460	Cell Line	L929	Mus musculus	Inhibition	=	-1.0	%	PMID[458815]
NPT993	Cell Line	Hepatocyte	Mus musculus	Inhibition	=	5.0	%	PMID[458815]
NPT993	Cell Line	Hepatocyte	Mus musculus	Inhibition	=	11.0	%	PMID[458815]
NPT1460	Cell Line	L929	Mus musculus	Inhibition	=	11.0	%	PMID[458815]
NPT993	Cell Line	Hepatocyte	Mus musculus	Inhibition	=	14.0	%	PMID[458815]
NPT993	Cell Line	Hepatocyte	Mus musculus	Inhibition	=	50.0	%	PMID[458815]
NPT993	Cell Line	Hepatocyte	Mus musculus	Inhibition	=	53.0	%	PMID[458815]
NPT1460	Cell Line	L929	Mus musculus	Inhibition	=	12.0	%	PMID[458815]
NPT993	Cell Line	Hepatocyte	Mus musculus	Inhibition	=	31.0	%	PMID[458815]
NPT993	Cell Line	Hepatocyte	Mus musculus	IC50	=	17000.0	nM	PMID[458815]
NPT472	Individual Protein	Vanilloid receptor	Homo sapiens	EC50	=	3981.07	nM	PMID[458817]
NPT472	Individual Protein	Vanilloid receptor	Homo sapiens	Emax	=	88.0	%	PMID[458817]
NPT64	Individual Protein	ATPase family AAA domain-containing protein 5	Homo sapiens	Potency	n.a.	20587.8	nM	PMID[458818]
NPT160	Individual Protein	TAR DNA-binding protein 43	Homo sapiens	Potency	n.a.	3548.1	nM	PMID[458818]
NPT2	Others	Unspecified		Inhibition	=	2.0	%	PMID[458815]
NPT2	Others	Unspecified		Inhibition	=	20.0	%	PMID[458815]
NPT2	Others	Unspecified		Inhibition	=	7.0	%	PMID[458815]
NPT2	Others	Unspecified		Inhibition	=	3.0	%	PMID[458815]
NPT2	Others	Unspecified		Activity	=	138.0	%	PMID[458816]
NPT2	Others	Unspecified		Activity	=	187.0	%	PMID[458816]
NPT2	Others	Unspecified		EC50	=	56000.0	nM	PMID[458816]

☑ 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 NPC252107 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	254
0.1-0.2	1462
0.2-0.3	6319
0.3-0.4	12092
0.4-0.5	5552
0.5-0.6	12495
0.6-0.7	3999
0.7-0.8	477
0.8-0.85	9
0.85-0.9	10
0.9-0.95	15
0.95-1	13

Similarity Score	Similarity Level	Natural Product ID
0.9922	High Similarity	NPC99078
0.9846	High Similarity	NPC220923
0.9845	High Similarity	NPC255817
0.9845	High Similarity	NPC230698
0.9845	High Similarity	NPC73883
0.9845	High Similarity	NPC251454
0.9845	High Similarity	NPC196609
0.9845	High Similarity	NPC277042
0.9845	High Similarity	NPC136330
0.9845	High Similarity	NPC205178
0.9767	High Similarity	NPC167096
0.9695	High Similarity	NPC470707
0.947	High Similarity	NPC145446
0.947	High Similarity	NPC137172
0.9398	High Similarity	NPC95366
0.9398	High Similarity	NPC248505
0.9394	High Similarity	NPC96406
0.9318	High Similarity	NPC94280
0.9318	High Similarity	NPC103947
0.9318	High Similarity	NPC45783
0.9318	High Similarity	NPC159150
0.9318	High Similarity	NPC193673
0.9318	High Similarity	NPC328419
0.9254	High Similarity	NPC225745
0.9248	High Similarity	NPC180647
0.9167	High Similarity	NPC217574
0.9037	High Similarity	NPC469808
0.9021	High Similarity	NPC471073
0.9021	High Similarity	NPC270811
0.8905	High Similarity	NPC231572
0.8881	High Similarity	NPC318862
0.8832	High Similarity	NPC28641
0.8832	High Similarity	NPC194359
0.8662	High Similarity	NPC469978
0.8639	High Similarity	NPC169742
0.8592	High Similarity	NPC244338
0.8425	Intermediate Similarity	NPC470088
0.8366	Intermediate Similarity	NPC231198
0.8357	Intermediate Similarity	NPC7018
0.8243	Intermediate Similarity	NPC223125
0.8227	Intermediate Similarity	NPC416184
0.82	Intermediate Similarity	NPC470708
0.8169	Intermediate Similarity	NPC214036
0.8169	Intermediate Similarity	NPC113236
0.8133	Intermediate Similarity	NPC223124
0.8108	Intermediate Similarity	NPC475959
0.8105	Intermediate Similarity	NPC106786
0.8071	Intermediate Similarity	NPC118419
0.8065	Intermediate Similarity	NPC59567
0.8045	Intermediate Similarity	NPC69670
0.7975	Intermediate Similarity	NPC241055
0.7971	Intermediate Similarity	NPC218323
0.7955	Intermediate Similarity	NPC111225
0.7941	Intermediate Similarity	NPC256167
0.7929	Intermediate Similarity	NPC470706
0.7929	Intermediate Similarity	NPC160193
0.7914	Intermediate Similarity	NPC99798
0.7914	Intermediate Similarity	NPC172403
0.7914	Intermediate Similarity	NPC191302
0.7914	Intermediate Similarity	NPC64948
0.7914	Intermediate Similarity	NPC157740
0.7907	Intermediate Similarity	NPC31279
0.7902	Intermediate Similarity	NPC11147
0.7895	Intermediate Similarity	NPC212643
0.7895	Intermediate Similarity	NPC148898
0.7895	Intermediate Similarity	NPC199209
0.7868	Intermediate Similarity	NPC114845
0.7857	Intermediate Similarity	NPC147247
0.7857	Intermediate Similarity	NPC246974
0.7842	Intermediate Similarity	NPC156944
0.7842	Intermediate Similarity	NPC251466
0.7829	Intermediate Similarity	NPC119669
0.7793	Intermediate Similarity	NPC193528
0.7792	Intermediate Similarity	NPC76079
0.7792	Intermediate Similarity	NPC216459
0.7792	Intermediate Similarity	NPC41178
0.7792	Intermediate Similarity	NPC93593
0.7792	Intermediate Similarity	NPC138487
0.7792	Intermediate Similarity	NPC78733
0.7786	Intermediate Similarity	NPC291449
0.7786	Intermediate Similarity	NPC41331
0.7785	Intermediate Similarity	NPC145304
0.7785	Intermediate Similarity	NPC168409
0.7785	Intermediate Similarity	NPC306669
0.7778	Intermediate Similarity	NPC233029
0.7778	Intermediate Similarity	NPC57501
0.7778	Intermediate Similarity	NPC210148
0.777	Intermediate Similarity	NPC207541
0.777	Intermediate Similarity	NPC85830
0.777	Intermediate Similarity	NPC170583
0.777	Intermediate Similarity	NPC71105
0.777	Intermediate Similarity	NPC152186
0.777	Intermediate Similarity	NPC246133
0.777	Intermediate Similarity	NPC182147
0.7748	Intermediate Similarity	NPC37144
0.7748	Intermediate Similarity	NPC59907
0.7742	Intermediate Similarity	NPC146288
0.7742	Intermediate Similarity	NPC31311
0.7742	Intermediate Similarity	NPC234392
0.773	Intermediate Similarity	NPC469977
0.7721	Intermediate Similarity	NPC344161
0.7712	Intermediate Similarity	NPC476579
0.7711	Intermediate Similarity	NPC116007
0.7708	Intermediate Similarity	NPC473463
0.7698	Intermediate Similarity	NPC300955
0.7692	Intermediate Similarity	NPC127326
0.7687	Intermediate Similarity	NPC314682
0.7681	Intermediate Similarity	NPC298486
0.7671	Intermediate Similarity	NPC254610
0.7655	Intermediate Similarity	NPC475828
0.7639	Intermediate Similarity	NPC266425
0.7635	Intermediate Similarity	NPC328750
0.7635	Intermediate Similarity	NPC188163
0.7635	Intermediate Similarity	NPC213206
0.7635	Intermediate Similarity	NPC474915
0.7622	Intermediate Similarity	NPC477694
0.7622	Intermediate Similarity	NPC477705
0.7619	Intermediate Similarity	NPC477259
0.7619	Intermediate Similarity	NPC169387
0.7609	Intermediate Similarity	NPC193484
0.7609	Intermediate Similarity	NPC80241
0.7609	Intermediate Similarity	NPC301641
0.7607	Intermediate Similarity	NPC4669
0.7605	Intermediate Similarity	NPC83511
0.7597	Intermediate Similarity	NPC85747
0.7597	Intermediate Similarity	NPC8337
0.7595	Intermediate Similarity	NPC215829
0.7595	Intermediate Similarity	NPC232924
0.7595	Intermediate Similarity	NPC160298
0.7595	Intermediate Similarity	NPC97072
0.7595	Intermediate Similarity	NPC306902
0.7595	Intermediate Similarity	NPC266753
0.7595	Intermediate Similarity	NPC477559
0.7586	Intermediate Similarity	NPC282477
0.7586	Intermediate Similarity	NPC284855
0.7582	Intermediate Similarity	NPC211296
0.7569	Intermediate Similarity	NPC477706
0.7566	Intermediate Similarity	NPC90844
0.7566	Intermediate Similarity	NPC95075
0.7566	Intermediate Similarity	NPC253883
0.755	Intermediate Similarity	NPC130926
0.7548	Intermediate Similarity	NPC476580
0.7546	Intermediate Similarity	NPC303581
0.7546	Intermediate Similarity	NPC67978
0.7545	Intermediate Similarity	NPC102760
0.7535	Intermediate Similarity	NPC286683
0.7532	Intermediate Similarity	NPC329640
0.7532	Intermediate Similarity	NPC477080
0.7532	Intermediate Similarity	NPC111485
0.7532	Intermediate Similarity	NPC118804
0.7531	Intermediate Similarity	NPC86469
0.7517	Intermediate Similarity	NPC160692
0.7515	Intermediate Similarity	NPC471650
0.75	Intermediate Similarity	NPC120075
0.75	Intermediate Similarity	NPC249788
0.7484	Intermediate Similarity	NPC135006
0.7484	Intermediate Similarity	NPC474852
0.7483	Intermediate Similarity	NPC301050
0.7483	Intermediate Similarity	NPC167944
0.7483	Intermediate Similarity	NPC231884
0.7483	Intermediate Similarity	NPC131204
0.7483	Intermediate Similarity	NPC42793
0.7469	Intermediate Similarity	NPC57812
0.7469	Intermediate Similarity	NPC474324
0.7468	Intermediate Similarity	NPC469539
0.7468	Intermediate Similarity	NPC469540
0.7468	Intermediate Similarity	NPC219162
0.7467	Intermediate Similarity	NPC908
0.7467	Intermediate Similarity	NPC138438
0.7465	Intermediate Similarity	NPC301713
0.7455	Intermediate Similarity	NPC308267
0.7455	Intermediate Similarity	NPC181905
0.7453	Intermediate Similarity	NPC238530
0.7453	Intermediate Similarity	NPC225774
0.7453	Intermediate Similarity	NPC232514
0.7453	Intermediate Similarity	NPC276944
0.7445	Intermediate Similarity	NPC277460
0.7434	Intermediate Similarity	NPC185838
0.7432	Intermediate Similarity	NPC102260
0.7432	Intermediate Similarity	NPC253429
0.7432	Intermediate Similarity	NPC230968
0.7431	Intermediate Similarity	NPC476748
0.7426	Intermediate Similarity	NPC268317
0.7425	Intermediate Similarity	NPC27887
0.7423	Intermediate Similarity	NPC475845
0.7417	Intermediate Similarity	NPC136860
0.7417	Intermediate Similarity	NPC128019
0.7417	Intermediate Similarity	NPC476567
0.7407	Intermediate Similarity	NPC219341
0.7407	Intermediate Similarity	NPC476432
0.7407	Intermediate Similarity	NPC24264
0.7407	Intermediate Similarity	NPC474858
0.7405	Intermediate Similarity	NPC57512
0.74	Intermediate Similarity	NPC275150
0.7394	Intermediate Similarity	NPC17348
0.7391	Intermediate Similarity	NPC320104
0.7391	Intermediate Similarity	NPC119949
0.7383	Intermediate Similarity	NPC166184
0.7378	Intermediate Similarity	NPC474708
0.7375	Intermediate Similarity	NPC26353

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 NPC252107 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	175
0.1-0.2	724
0.2-0.3	1019
0.3-0.4	2219
0.4-0.5	2648
0.5-0.6	1636
0.6-0.7	634
0.7-0.8	91
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9845	High Similarity	NPD2492	Phase 1
0.8345	Intermediate Similarity	NPD5297	Approved
0.8151	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD5718	Phase 2
0.7959	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7943	Intermediate Similarity	NPD554	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD1337	Clinical (unspecified phase)
0.7676	Intermediate Similarity	NPD2669	Clinical (unspecified phase)
0.7671	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7671	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7635	Intermediate Similarity	NPD4664	Clinical (unspecified phase)
0.7613	Intermediate Similarity	NPD7110	Phase 1
0.7613	Intermediate Similarity	NPD7109	Clinical (unspecified phase)
0.7582	Intermediate Similarity	NPD6662	Clinical (unspecified phase)
0.758	Intermediate Similarity	NPD5977	Approved
0.758	Intermediate Similarity	NPD5978	Approved
0.7561	Intermediate Similarity	NPD3885	Approved
0.7532	Intermediate Similarity	NPD4210	Discontinued
0.7484	Intermediate Similarity	NPD5604	Discontinued
0.7484	Intermediate Similarity	NPD824	Approved
0.7483	Intermediate Similarity	NPD6895	Approved
0.7483	Intermediate Similarity	NPD6896	Approved
0.7467	Intermediate Similarity	NPD4236	Phase 3
0.7467	Intermediate Similarity	NPD4237	Approved
0.7452	Intermediate Similarity	NPD7945	Clinical (unspecified phase)
0.7415	Intermediate Similarity	NPD2653	Approved
0.7407	Intermediate Similarity	NPD4166	Phase 2
0.7397	Intermediate Similarity	NPD3140	Approved
0.7397	Intermediate Similarity	NPD3142	Approved
0.7389	Intermediate Similarity	NPD6386	Approved
0.7389	Intermediate Similarity	NPD6873	Phase 2
0.7389	Intermediate Similarity	NPD6385	Approved
0.7381	Intermediate Similarity	NPD7280	Phase 3
0.7381	Intermediate Similarity	NPD7281	Phase 3
0.7376	Intermediate Similarity	NPD1420	Approved
0.7376	Intermediate Similarity	NPD1421	Approved
0.7372	Intermediate Similarity	NPD5536	Phase 2
0.7357	Intermediate Similarity	NPD3705	Approved
0.7355	Intermediate Similarity	NPD3640	Phase 3
0.7355	Intermediate Similarity	NPD3641	Approved
0.7355	Intermediate Similarity	NPD3639	Approved
0.7338	Intermediate Similarity	NPD3146	Approved
0.7338	Intermediate Similarity	NPD4584	Approved
0.7338	Intermediate Similarity	NPD3688	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD2423	Clinical (unspecified phase)
0.7325	Intermediate Similarity	NPD6875	Approved
0.7325	Intermediate Similarity	NPD6876	Approved
0.7296	Intermediate Similarity	NPD2978	Approved
0.7296	Intermediate Similarity	NPD2977	Approved
0.7288	Intermediate Similarity	NPD5457	Discontinued
0.7266	Intermediate Similarity	NPD1357	Approved
0.7248	Intermediate Similarity	NPD743	Approved
0.7248	Intermediate Similarity	NPD6111	Discontinued
0.7237	Intermediate Similarity	NPD5177	Phase 3
0.7214	Intermediate Similarity	NPD2667	Approved
0.7214	Intermediate Similarity	NPD2668	Approved
0.7212	Intermediate Similarity	NPD2898	Approved
0.7211	Intermediate Similarity	NPD3530	Approved
0.7211	Intermediate Similarity	NPD3532	Approved
0.7211	Intermediate Similarity	NPD2245	Discovery
0.7211	Intermediate Similarity	NPD2674	Phase 3
0.7211	Intermediate Similarity	NPD3531	Approved
0.7206	Intermediate Similarity	NPD5283	Phase 1
0.7203	Intermediate Similarity	NPD7258	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD4579	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD4017	Approved
0.7143	Intermediate Similarity	NPD2219	Phase 1
0.7143	Intermediate Similarity	NPD5241	Discontinued
0.7143	Intermediate Similarity	NPD6382	Discontinued
0.7135	Intermediate Similarity	NPD6618	Phase 2
0.7134	Intermediate Similarity	NPD6030	Approved
0.7134	Intermediate Similarity	NPD6031	Approved
0.7124	Intermediate Similarity	NPD4162	Approved
0.7124	Intermediate Similarity	NPD3060	Approved
0.7115	Intermediate Similarity	NPD1424	Approved
0.711	Intermediate Similarity	NPD3349	Phase 2
0.7105	Intermediate Similarity	NPD3656	Approved
0.7105	Intermediate Similarity	NPD1375	Discontinued
0.7101	Intermediate Similarity	NPD6297	Approved
0.7097	Intermediate Similarity	NPD7124	Phase 2
0.7088	Intermediate Similarity	NPD7607	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD5312	Approved
0.7083	Intermediate Similarity	NPD5313	Approved
0.7063	Intermediate Similarity	NPD2232	Approved
0.7063	Intermediate Similarity	NPD2233	Approved
0.7063	Intermediate Similarity	NPD2230	Approved
0.7059	Intermediate Similarity	NPD1044	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD1372	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD4357	Discontinued
0.7047	Intermediate Similarity	NPD3110	Approved
0.7047	Intermediate Similarity	NPD3109	Approved
0.7039	Intermediate Similarity	NPD1725	Approved
0.7037	Intermediate Similarity	NPD5353	Approved
0.7032	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD3144	Approved
0.7027	Intermediate Similarity	NPD3145	Approved
0.7027	Intermediate Similarity	NPD3374	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD1670	Discontinued
0.7025	Intermediate Similarity	NPD4727	Phase 1
0.7025	Intermediate Similarity	NPD2122	Discontinued
0.702	Intermediate Similarity	NPD7119	Phase 2
0.7019	Intermediate Similarity	NPD3383	Approved
0.7019	Intermediate Similarity	NPD3382	Approved
0.7019	Intermediate Similarity	NPD3384	Approved
0.7014	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD7291	Discontinued
0.7006	Intermediate Similarity	NPD4481	Phase 3
0.7006	Intermediate Similarity	NPD4739	Approved
0.6987	Remote Similarity	NPD2120	Phase 2
0.6986	Remote Similarity	NPD7905	Discontinued
0.6975	Remote Similarity	NPD5773	Approved
0.6975	Remote Similarity	NPD6818	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD5772	Approved
0.6975	Remote Similarity	NPD5563	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD5481	Discontinued
0.6966	Remote Similarity	NPD2922	Phase 1
0.6966	Remote Similarity	NPD5582	Discontinued
0.6962	Remote Similarity	NPD3647	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD5746	Approved
0.6957	Remote Similarity	NPD4773	Phase 2
0.6957	Remote Similarity	NPD4772	Phase 2
0.6943	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6936	Remote Similarity	NPD6853	Approved
0.6936	Remote Similarity	NPD6851	Approved
0.6934	Remote Similarity	NPD228	Approved
0.6933	Remote Similarity	NPD2560	Approved
0.6933	Remote Similarity	NPD2563	Approved
0.6932	Remote Similarity	NPD5525	Clinical (unspecified phase)
0.6929	Remote Similarity	NPD3596	Phase 2
0.6928	Remote Similarity	NPD2161	Phase 2
0.6928	Remote Similarity	NPD6107	Approved
0.6923	Remote Similarity	NPD3447	Discontinued
0.6918	Remote Similarity	NPD5976	Discontinued
0.6918	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD4098	Discontinued
0.6914	Remote Similarity	NPD7298	Approved
0.6913	Remote Similarity	NPD1336	Approved
0.691	Remote Similarity	NPD6493	Phase 3
0.6899	Remote Similarity	NPD1754	Clinical (unspecified phase)
0.689	Remote Similarity	NPD6788	Approved
0.6889	Remote Similarity	NPD1358	Approved
0.6889	Remote Similarity	NPD4420	Approved
0.6886	Remote Similarity	NPD6071	Discontinued
0.6879	Remote Similarity	NPD160	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD5295	Discontinued
0.6875	Remote Similarity	NPD3686	Approved
0.6875	Remote Similarity	NPD3687	Approved
0.6875	Remote Similarity	NPD4124	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD7018	Phase 2
0.6871	Remote Similarity	NPD4585	Approved
0.6867	Remote Similarity	NPD2041	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD5677	Discontinued
0.6867	Remote Similarity	NPD5745	Approved
0.6867	Remote Similarity	NPD2042	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD4108	Discontinued
0.6859	Remote Similarity	NPD6331	Phase 2
0.6859	Remote Similarity	NPD5754	Discontinued
0.6855	Remote Similarity	NPD1975	Clinical (unspecified phase)
0.6846	Remote Similarity	NPD5163	Phase 2
0.6845	Remote Similarity	NPD5242	Approved
0.6845	Remote Similarity	NPD2388	Discontinued
0.6839	Remote Similarity	NPD7153	Discontinued
0.6832	Remote Similarity	NPD7261	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD3866	Clinical (unspecified phase)
0.6831	Remote Similarity	NPD2486	Discontinued
0.6829	Remote Similarity	NPD5967	Approved
0.6824	Remote Similarity	NPD2040	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD7549	Discontinued
0.6821	Remote Similarity	NPD7132	Clinical (unspecified phase)
0.6815	Remote Similarity	NPD3134	Approved
0.6806	Remote Similarity	NPD3294	Phase 2
0.68	Remote Similarity	NPD1039	Discontinued
0.68	Remote Similarity	NPD6812	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD2335	Discontinued
0.6792	Remote Similarity	NPD4123	Phase 3
0.6788	Remote Similarity	NPD5019	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD3051	Approved
0.6783	Remote Similarity	NPD2594	Approved
0.6783	Remote Similarity	NPD2595	Approved
0.6781	Remote Similarity	NPD1669	Approved
0.678	Remote Similarity	NPD7235	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD5865	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD3281	Clinical (unspecified phase)
0.6766	Remote Similarity	NPD7201	Clinical (unspecified phase)
0.6766	Remote Similarity	NPD2904	Discontinued
0.6761	Remote Similarity	NPD4084	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD6584	Phase 3
0.6752	Remote Similarity	NPD6658	Clinical (unspecified phase)
0.675	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6748	Remote Similarity	NPD5090	Approved
0.6748	Remote Similarity	NPD5089	Approved
0.6747	Remote Similarity	NPD1309	Phase 2
0.6747	Remote Similarity	NPD7831	Phase 2
0.6747	Remote Similarity	NPD7832	Clinical (unspecified phase)
0.6747	Remote Similarity	NPD7833	Phase 2
0.6747	Remote Similarity	NPD1307	Phase 2
0.6747	Remote Similarity	NPD8031	Discontinued
0.6746	Remote Similarity	NPD2970	Approved
0.6746	Remote Similarity	NPD2969	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