NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	244.11
Volume:	255.515
LogP:	3.79
LogD:	3.532
LogS:	-4.863
# Rotatable Bonds:	0
TPSA:	46.51
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.713
Synthetic Accessibility Score:	4.716
Fsp3:	0.333
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:	-4.676
MDCK Permeability:	2.3027283532428555e-05
Pgp-inhibitor:	0.009
Pgp-substrate:	0.033
Human Intestinal Absorption (HIA):	0.014
20% Bioavailability (F20%):	0.008
30% Bioavailability (F30%):	0.003

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.043
Plasma Protein Binding (PPB):	95.67440795898438%
Volume Distribution (VD):	0.779
Pgp-substrate:	1.5932148694992065%

ADMET: Metabolism

CYP1A2-inhibitor:	0.845
CYP1A2-substrate:	0.677
CYP2C19-inhibitor:	0.23
CYP2C19-substrate:	0.084
CYP2C9-inhibitor:	0.54
CYP2C9-substrate:	0.643
CYP2D6-inhibitor:	0.191
CYP2D6-substrate:	0.85
CYP3A4-inhibitor:	0.34
CYP3A4-substrate:	0.159

ADMET: Excretion

Clearance (CL):	6.07
Half-life (T1/2):	0.432

ADMET: Toxicity

hERG Blockers:	0.008
Human Hepatotoxicity (H-HT):	0.583
Drug-inuced Liver Injury (DILI):	0.717
AMES Toxicity:	0.008
Rat Oral Acute Toxicity:	0.72
Maximum Recommended Daily Dose:	0.461
Skin Sensitization:	0.191
Carcinogencity:	0.612
Eye Corrosion:	0.003
Eye Irritation:	0.015
Respiratory Toxicity:	0.802

Download Data

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

Natural Product: NPC216810

Natural Product ID:	NPC216810
*Common Name:**	Linderalactone
IUPAC Name:	n.a.
Synonyms:	Linderalactone
Standard InCHIKey:	LWCKQMHMTSRRAA-QGQQYVBWSA-N
Standard InCHI:	InChI=1S/C15H16O3/c1-9-4-3-5-11-7-13(18-15(11)16)14-10(2)8-17-12(14)6-9/h4,7-8,13H,3,5-6H2,1-2H3/b9-4+/t13-/m1/s1
SMILES:	C/C/1=CCCC2=C[C@H](c3c(C)coc3C1)OC2=O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1080239
PubChem CID:	6450191
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001983] Dihydrofurans [CHEMONTID:0001982] Furanones [CHEMONTID:0002223] Butenolides

*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
NPO15351	Streptomyces prunicolor	Species	Streptomycetaceae	Bacteria	n.a.	mycelium	n.a.	DOI[10.1021/np50098a008]
NPO12553	Lindera chunii	Species	Lauraceae	Eukaryota	n.a.	root	n.a.	PMID[12237535]
NPO6541	Scrophularia buergeriana	Species	Scrophulariaceae	Eukaryota	roots	n.a.	n.a.	PMID[12444706]
NPO11093	Pseudobersama mossambicensis	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1479381]
NPO4682	Lindera aggregata	Species	Lauraceae	Eukaryota	n.a.	leaf	n.a.	PMID[17999353]
NPO4682	Lindera aggregata	Species	Lauraceae	Eukaryota	Roots; Tubers	n.a.	n.a.	PMID[19639966]
NPO23270	Neolitsea daibuensis	Species	Lauraceae	Eukaryota	n.a.	root	n.a.	PMID[22148193]
NPO11898	Lobophora variegata	Species	Dictyotaceae	Eukaryota	n.a.	at depths of 630 m at El Mdano (Tenerife, Canary Islands)	n.a.	PMID[26126835]
NPO5247	Elaphoglossum lindbergii	Species	Dryopteridaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26689830]
NPO12553	Lindera chunii	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12633	Rapanea neurophylla	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO31274	Lindera strychnifolia	Species	Tineidae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO10530	Aconitum subcuneatum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12853	Leucocarpus perfoliatus	Species	Phrymaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO6541	Scrophularia buergeriana	Species	Scrophulariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO10530	Aconitum subcuneatum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12633	Rapanea neurophylla	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6696	Chukrasia tabularis	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4682	Lindera aggregata	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6541	Scrophularia buergeriana	Species	Scrophulariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12553	Lindera chunii	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11206	Trifolium hybridum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12853	Leucocarpus perfoliatus	Species	Phrymaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO31274	Lindera strychnifolia	Species	Tineidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO6541	Scrophularia buergeriana	Species	Scrophulariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO10530	Aconitum subcuneatum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO6541	Scrophularia buergeriana	Species	Scrophulariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO4682	Lindera aggregata	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO5247	Elaphoglossum lindbergii	Species	Dryopteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11206	Trifolium hybridum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12146	Stemodia maritima	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9363	Ferula ammoniacum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23883	Penicillium abidjanum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6541	Scrophularia buergeriana	Species	Scrophulariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2207	Sphaerella rubella	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO12853	Leucocarpus perfoliatus	Species	Phrymaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1116	Periconia atropurpurea	Species	Periconiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11093	Pseudobersama mossambicensis	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11527	Ibacus peronii	Species	Scyllaridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1044	Caiman crocodilus	Species	Alligatoridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4682	Lindera aggregata	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10530	Aconitum subcuneatum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15351	Streptomyces prunicolor	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO11898	Lobophora variegata	Species	Dictyotaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12633	Rapanea neurophylla	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4228	Wickerhamomyces anomalus	Species	Phaffomycetaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2996	Pistacia atlantica	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12553	Lindera chunii	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6696	Chukrasia tabularis	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7560	Tachardia acaciae	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO23270	Neolitsea daibuensis	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5714	Rogeria adenophylla	Species	Pedaliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9606	Castanea dentata	Species	Fagaceae	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	1
IC50	2

Activity Type	# Activity
Cell Line	1
NON-MOLECULAR	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT65	Cell Line	HepG2	Homo sapiens	EC50	=	98000.0	nM	PMID[489514]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	8.48	ug.mL-1	PMID[489515]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	3.21	ug.mL-1	PMID[489515]

☑ 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 NPC216810 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	311
0.1-0.2	1542
0.2-0.3	4820
0.3-0.4	10419
0.4-0.5	9391
0.5-0.6	8083
0.6-0.7	7409
0.7-0.8	669
0.8-0.85	46
0.85-0.9	4
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9147	High Similarity	NPC286130
0.9076	High Similarity	NPC227660
0.8828	High Similarity	NPC136340
0.8814	High Similarity	NPC22678
0.8593	High Similarity	NPC248795
0.8561	High Similarity	NPC159786
0.8516	High Similarity	NPC184391
0.848	Intermediate Similarity	NPC1848
0.8444	Intermediate Similarity	NPC474615
0.8372	Intermediate Similarity	NPC319140
0.8372	Intermediate Similarity	NPC95567
0.832	Intermediate Similarity	NPC67345
0.832	Intermediate Similarity	NPC244862
0.8293	Intermediate Similarity	NPC205523
0.8273	Intermediate Similarity	NPC84479
0.8209	Intermediate Similarity	NPC200718
0.8209	Intermediate Similarity	NPC106247
0.8182	Intermediate Similarity	NPC21460
0.8182	Intermediate Similarity	NPC45947
0.8175	Intermediate Similarity	NPC473969
0.816	Intermediate Similarity	NPC217180
0.816	Intermediate Similarity	NPC312525
0.816	Intermediate Similarity	NPC131801
0.814	Intermediate Similarity	NPC188377
0.814	Intermediate Similarity	NPC65735
0.8125	Intermediate Similarity	NPC270807
0.8125	Intermediate Similarity	NPC323118
0.8125	Intermediate Similarity	NPC174915
0.8115	Intermediate Similarity	NPC105249
0.8102	Intermediate Similarity	NPC472376
0.8095	Intermediate Similarity	NPC187547
0.8095	Intermediate Similarity	NPC21831
0.8085	Intermediate Similarity	NPC195920
0.8071	Intermediate Similarity	NPC254198
0.8071	Intermediate Similarity	NPC205071
0.8065	Intermediate Similarity	NPC292036
0.8031	Intermediate Similarity	NPC4898
0.8029	Intermediate Similarity	NPC473268
0.8028	Intermediate Similarity	NPC62799
0.8015	Intermediate Similarity	NPC92941
0.8	Intermediate Similarity	NPC118853
0.7986	Intermediate Similarity	NPC282973
0.7985	Intermediate Similarity	NPC475092
0.7984	Intermediate Similarity	NPC263870
0.7958	Intermediate Similarity	NPC37488
0.7943	Intermediate Similarity	NPC110305
0.7937	Intermediate Similarity	NPC79202
0.7937	Intermediate Similarity	NPC45536
0.7937	Intermediate Similarity	NPC59035
0.7917	Intermediate Similarity	NPC19747
0.7914	Intermediate Similarity	NPC107571
0.7907	Intermediate Similarity	NPC97566
0.7902	Intermediate Similarity	NPC475864
0.7902	Intermediate Similarity	NPC104924
0.7899	Intermediate Similarity	NPC470742
0.7879	Intermediate Similarity	NPC474260
0.7879	Intermediate Similarity	NPC81912
0.7879	Intermediate Similarity	NPC329922
0.7879	Intermediate Similarity	NPC329694
0.7863	Intermediate Similarity	NPC243269
0.7862	Intermediate Similarity	NPC474270
0.7862	Intermediate Similarity	NPC475904
0.7862	Intermediate Similarity	NPC211625
0.7857	Intermediate Similarity	NPC28054
0.7847	Intermediate Similarity	NPC308799
0.7842	Intermediate Similarity	NPC220094
0.7842	Intermediate Similarity	NPC476943
0.782	Intermediate Similarity	NPC141059
0.7803	Intermediate Similarity	NPC473885
0.7803	Intermediate Similarity	NPC471074
0.7803	Intermediate Similarity	NPC75557
0.7803	Intermediate Similarity	NPC71274
0.7795	Intermediate Similarity	NPC476014
0.7795	Intermediate Similarity	NPC476031
0.7793	Intermediate Similarity	NPC113428
0.7793	Intermediate Similarity	NPC474255
0.7793	Intermediate Similarity	NPC474220
0.7793	Intermediate Similarity	NPC61284
0.7793	Intermediate Similarity	NPC471618
0.7786	Intermediate Similarity	NPC475818
0.7786	Intermediate Similarity	NPC476351
0.777	Intermediate Similarity	NPC310830
0.777	Intermediate Similarity	NPC186626
0.777	Intermediate Similarity	NPC215109
0.777	Intermediate Similarity	NPC170604
0.7769	Intermediate Similarity	NPC79557
0.7761	Intermediate Similarity	NPC329707
0.7752	Intermediate Similarity	NPC137710
0.7744	Intermediate Similarity	NPC83301
0.7737	Intermediate Similarity	NPC474425
0.7737	Intermediate Similarity	NPC474426
0.7737	Intermediate Similarity	NPC474407
0.7737	Intermediate Similarity	NPC470740
0.7737	Intermediate Similarity	NPC293253
0.7734	Intermediate Similarity	NPC144745
0.7734	Intermediate Similarity	NPC217423
0.7734	Intermediate Similarity	NPC208906
0.7724	Intermediate Similarity	NPC471521
0.7724	Intermediate Similarity	NPC474317
0.7724	Intermediate Similarity	NPC473356
0.7717	Intermediate Similarity	NPC11821
0.771	Intermediate Similarity	NPC283284
0.771	Intermediate Similarity	NPC289911
0.7705	Intermediate Similarity	NPC42471
0.7698	Intermediate Similarity	NPC146872
0.7698	Intermediate Similarity	NPC303217
0.7692	Intermediate Similarity	NPC230951
0.7692	Intermediate Similarity	NPC22248
0.7692	Intermediate Similarity	NPC267632
0.7692	Intermediate Similarity	NPC223415
0.7687	Intermediate Similarity	NPC476016
0.7687	Intermediate Similarity	NPC137570
0.7669	Intermediate Similarity	NPC474829
0.7656	Intermediate Similarity	NPC76844
0.7651	Intermediate Similarity	NPC114880
0.7647	Intermediate Similarity	NPC66246
0.7647	Intermediate Similarity	NPC170546
0.7643	Intermediate Similarity	NPC307401
0.7639	Intermediate Similarity	NPC307346
0.7639	Intermediate Similarity	NPC261733
0.7639	Intermediate Similarity	NPC267004
0.7639	Intermediate Similarity	NPC218712
0.7634	Intermediate Similarity	NPC474136
0.763	Intermediate Similarity	NPC474438
0.763	Intermediate Similarity	NPC474279
0.7606	Intermediate Similarity	NPC218204
0.7606	Intermediate Similarity	NPC473681
0.7606	Intermediate Similarity	NPC61157
0.7603	Intermediate Similarity	NPC224418
0.76	Intermediate Similarity	NPC75310
0.7594	Intermediate Similarity	NPC178382
0.7591	Intermediate Similarity	NPC282230
0.7591	Intermediate Similarity	NPC183348
0.7591	Intermediate Similarity	NPC298190
0.7591	Intermediate Similarity	NPC477645
0.7589	Intermediate Similarity	NPC236532
0.7586	Intermediate Similarity	NPC56731
0.7584	Intermediate Similarity	NPC474219
0.7584	Intermediate Similarity	NPC474378
0.7578	Intermediate Similarity	NPC188907
0.7574	Intermediate Similarity	NPC59502
0.7569	Intermediate Similarity	NPC64568
0.7569	Intermediate Similarity	NPC470741
0.7557	Intermediate Similarity	NPC474817
0.7556	Intermediate Similarity	NPC474830
0.7552	Intermediate Similarity	NPC20500
0.7538	Intermediate Similarity	NPC243704
0.7538	Intermediate Similarity	NPC206007
0.7538	Intermediate Similarity	NPC291619
0.7538	Intermediate Similarity	NPC254958
0.7537	Intermediate Similarity	NPC471559
0.7536	Intermediate Similarity	NPC470977
0.7536	Intermediate Similarity	NPC196979
0.7536	Intermediate Similarity	NPC15083
0.7536	Intermediate Similarity	NPC470976
0.7536	Intermediate Similarity	NPC471817
0.7536	Intermediate Similarity	NPC473982
0.7535	Intermediate Similarity	NPC202260
0.7535	Intermediate Similarity	NPC474722
0.7519	Intermediate Similarity	NPC16922
0.7517	Intermediate Similarity	NPC191104
0.7517	Intermediate Similarity	NPC142113
0.75	Intermediate Similarity	NPC329180
0.75	Intermediate Similarity	NPC115859
0.75	Intermediate Similarity	NPC470856
0.7483	Intermediate Similarity	NPC18904
0.7482	Intermediate Similarity	NPC214097
0.748	Intermediate Similarity	NPC1811
0.748	Intermediate Similarity	NPC26157
0.7467	Intermediate Similarity	NPC475777
0.7465	Intermediate Similarity	NPC177262
0.7464	Intermediate Similarity	NPC17681
0.7462	Intermediate Similarity	NPC45104
0.7451	Intermediate Similarity	NPC474611
0.745	Intermediate Similarity	NPC88445
0.7442	Intermediate Similarity	NPC150895
0.7438	Intermediate Similarity	NPC156768
0.7434	Intermediate Similarity	NPC474542
0.7432	Intermediate Similarity	NPC74539
0.7432	Intermediate Similarity	NPC93666
0.7432	Intermediate Similarity	NPC304443
0.7426	Intermediate Similarity	NPC471554
0.7426	Intermediate Similarity	NPC473355
0.7426	Intermediate Similarity	NPC471573
0.7426	Intermediate Similarity	NPC471501
0.7422	Intermediate Similarity	NPC53953
0.7417	Intermediate Similarity	NPC24232
0.7415	Intermediate Similarity	NPC246903
0.7415	Intermediate Similarity	NPC208584
0.7415	Intermediate Similarity	NPC262198
0.7415	Intermediate Similarity	NPC346
0.7415	Intermediate Similarity	NPC97904
0.7415	Intermediate Similarity	NPC233763
0.741	Intermediate Similarity	NPC97740
0.741	Intermediate Similarity	NPC45358
0.7407	Intermediate Similarity	NPC179354
0.7405	Intermediate Similarity	NPC293424
0.7397	Intermediate Similarity	NPC476944
0.7397	Intermediate Similarity	NPC86935
0.7394	Intermediate Similarity	NPC42400

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 NPC216810 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	276
0.1-0.2	1023
0.2-0.3	1941
0.3-0.4	2860
0.4-0.5	1879
0.5-0.6	911
0.6-0.7	239
0.7-0.8	21
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.766	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7556	Intermediate Similarity	NPD1019	Discontinued
0.7445	Intermediate Similarity	NPD6832	Phase 2
0.7432	Intermediate Similarity	NPD920	Approved
0.7415	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7388	Intermediate Similarity	NPD9717	Approved
0.7323	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.7313	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7279	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7192	Intermediate Similarity	NPD1243	Approved
0.7183	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7154	Intermediate Similarity	NPD1241	Discontinued
0.7101	Intermediate Similarity	NPD1203	Approved
0.7092	Intermediate Similarity	NPD2313	Discontinued
0.7063	Intermediate Similarity	NPD447	Suspended
0.7034	Intermediate Similarity	NPD2799	Discontinued
0.6992	Remote Similarity	NPD9493	Approved
0.6986	Remote Similarity	NPD1551	Phase 2
0.6986	Remote Similarity	NPD2796	Approved
0.6944	Remote Similarity	NPD1933	Approved
0.6939	Remote Similarity	NPD2346	Discontinued
0.6939	Remote Similarity	NPD2344	Approved
0.6939	Remote Similarity	NPD1471	Phase 3
0.6899	Remote Similarity	NPD2182	Approved
0.6857	Remote Similarity	NPD2797	Approved
0.6857	Remote Similarity	NPD3267	Approved
0.6857	Remote Similarity	NPD1049	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD3266	Approved
0.6855	Remote Similarity	NPD919	Approved
0.6853	Remote Similarity	NPD411	Approved
0.6842	Remote Similarity	NPD2532	Approved
0.6842	Remote Similarity	NPD2534	Approved
0.6842	Remote Similarity	NPD2533	Approved
0.6832	Remote Similarity	NPD6808	Phase 2
0.6809	Remote Similarity	NPD2798	Approved
0.6809	Remote Similarity	NPD5647	Approved
0.6776	Remote Similarity	NPD6799	Approved
0.6763	Remote Similarity	NPD3972	Approved
0.6759	Remote Similarity	NPD4307	Phase 2
0.6757	Remote Similarity	NPD2935	Discontinued
0.6755	Remote Similarity	NPD2309	Approved
0.6744	Remote Similarity	NPD3134	Approved
0.6736	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6736	Remote Similarity	NPD3268	Approved
0.6731	Remote Similarity	NPD6599	Discontinued
0.6719	Remote Similarity	NPD164	Approved
0.6718	Remote Similarity	NPD2067	Discontinued
0.6715	Remote Similarity	NPD5585	Approved
0.6711	Remote Similarity	NPD6002	Phase 3
0.6711	Remote Similarity	NPD6005	Phase 3
0.6711	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6711	Remote Similarity	NPD6004	Phase 3
0.6711	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6709	Remote Similarity	NPD5761	Phase 2
0.6709	Remote Similarity	NPD5760	Phase 2
0.6692	Remote Similarity	NPD1358	Approved
0.6689	Remote Similarity	NPD3748	Approved
0.6689	Remote Similarity	NPD4628	Phase 3
0.6667	Remote Similarity	NPD1238	Approved
0.6667	Remote Similarity	NPD1549	Phase 2
0.6667	Remote Similarity	NPD1247	Approved
0.6667	Remote Similarity	NPD1876	Approved
0.6667	Remote Similarity	NPD17	Approved
0.6646	Remote Similarity	NPD6279	Approved
0.6646	Remote Similarity	NPD6280	Approved
0.6645	Remote Similarity	NPD5403	Approved
0.6645	Remote Similarity	NPD3887	Approved
0.6642	Remote Similarity	NPD9545	Approved
0.6641	Remote Similarity	NPD9261	Approved
0.6623	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6623	Remote Similarity	NPD5401	Approved
0.6623	Remote Similarity	NPD2800	Approved
0.6608	Remote Similarity	NPD8434	Phase 2
0.6607	Remote Similarity	NPD6559	Discontinued
0.6605	Remote Similarity	NPD5494	Approved
0.6604	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6604	Remote Similarity	NPD7819	Suspended
0.66	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.66	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6599	Remote Similarity	NPD4618	Approved
0.6599	Remote Similarity	NPD4622	Approved
0.6593	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6584	Remote Similarity	NPD3749	Approved
0.6582	Remote Similarity	NPD5890	Approved
0.6582	Remote Similarity	NPD7411	Suspended
0.6582	Remote Similarity	NPD5889	Approved
0.6581	Remote Similarity	NPD6273	Approved
0.6579	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6577	Remote Similarity	NPD4308	Phase 3
0.6566	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD5402	Approved
0.6541	Remote Similarity	NPD6801	Discontinued
0.6538	Remote Similarity	NPD9697	Approved
0.6531	Remote Similarity	NPD3140	Approved
0.6531	Remote Similarity	NPD3142	Approved
0.6531	Remote Similarity	NPD1240	Approved
0.6525	Remote Similarity	NPD1608	Approved
0.6522	Remote Similarity	NPD1894	Discontinued
0.651	Remote Similarity	NPD5689	Approved
0.651	Remote Similarity	NPD5688	Approved
0.6503	Remote Similarity	NPD6362	Approved
0.6493	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6486	Remote Similarity	NPD6355	Discontinued
0.6481	Remote Similarity	NPD7075	Discontinued
0.6479	Remote Similarity	NPD4359	Approved
0.6471	Remote Similarity	NPD3750	Approved
0.6467	Remote Similarity	NPD7033	Discontinued
0.6463	Remote Similarity	NPD6233	Phase 2
0.646	Remote Similarity	NPD5616	Clinical (unspecified phase)
0.6458	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6456	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6456	Remote Similarity	NPD3226	Approved
0.6449	Remote Similarity	NPD9092	Discovery
0.6447	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6443	Remote Similarity	NPD1607	Approved
0.6439	Remote Similarity	NPD9267	Approved
0.6439	Remote Similarity	NPD9263	Approved
0.6439	Remote Similarity	NPD9264	Approved
0.6429	Remote Similarity	NPD1778	Approved
0.6429	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6424	Remote Similarity	NPD5668	Clinical (unspecified phase)
0.642	Remote Similarity	NPD7768	Phase 2
0.6415	Remote Similarity	NPD6585	Discontinued
0.6414	Remote Similarity	NPD9494	Approved
0.6412	Remote Similarity	NPD6764	Approved
0.6412	Remote Similarity	NPD6765	Approved
0.641	Remote Similarity	NPD4662	Approved
0.641	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.641	Remote Similarity	NPD4661	Approved
0.6395	Remote Similarity	NPD6798	Discontinued
0.6395	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6391	Remote Similarity	NPD74	Approved
0.6391	Remote Similarity	NPD9266	Approved
0.6386	Remote Similarity	NPD3926	Phase 2
0.6383	Remote Similarity	NPD3496	Discontinued
0.6382	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6382	Remote Similarity	NPD2353	Approved
0.6376	Remote Similarity	NPD230	Phase 1
0.6358	Remote Similarity	NPD1510	Phase 2
0.6358	Remote Similarity	NPD3817	Phase 2
0.6357	Remote Similarity	NPD5691	Approved
0.6351	Remote Similarity	NPD8032	Phase 2
0.6338	Remote Similarity	NPD1281	Approved
0.6333	Remote Similarity	NPD6653	Approved
0.6329	Remote Similarity	NPD3873	Phase 3
0.6329	Remote Similarity	NPD3869	Phase 3
0.6329	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6327	Remote Similarity	NPD2598	Clinical (unspecified phase)
0.6324	Remote Similarity	NPD5535	Approved
0.6319	Remote Similarity	NPD3882	Suspended
0.6319	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6309	Remote Similarity	NPD2979	Phase 3
0.6306	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6299	Remote Similarity	NPD2654	Approved
0.6296	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6294	Remote Similarity	NPD1481	Phase 2
0.6284	Remote Similarity	NPD3764	Approved
0.6284	Remote Similarity	NPD1296	Phase 2
0.6282	Remote Similarity	NPD7440	Discontinued
0.628	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6272	Remote Similarity	NPD3818	Discontinued
0.6264	Remote Similarity	NPD6785	Approved
0.6264	Remote Similarity	NPD6784	Approved
0.6258	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6258	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6258	Remote Similarity	NPD2296	Approved
0.625	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6242	Remote Similarity	NPD4870	Approved
0.6242	Remote Similarity	NPD4062	Phase 3
0.6241	Remote Similarity	NPD1651	Approved
0.6235	Remote Similarity	NPD6844	Discontinued
0.6235	Remote Similarity	NPD1934	Approved
0.6234	Remote Similarity	NPD2897	Discontinued
0.6234	Remote Similarity	NPD2424	Discontinued
0.6228	Remote Similarity	NPD5711	Approved
0.6228	Remote Similarity	NPD5710	Approved
0.6224	Remote Similarity	NPD1535	Discovery
0.6218	Remote Similarity	NPD3295	Clinical (unspecified phase)
0.6218	Remote Similarity	NPD2354	Approved
0.6211	Remote Similarity	NPD4380	Phase 2
0.6209	Remote Similarity	NPD4476	Approved
0.6209	Remote Similarity	NPD4477	Approved
0.6209	Remote Similarity	NPD2438	Suspended
0.6207	Remote Similarity	NPD3225	Approved
0.6207	Remote Similarity	NPD1283	Approved
0.6203	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6194	Remote Similarity	NPD290	Approved
0.619	Remote Similarity	NPD454	Approved
0.6184	Remote Similarity	NPD2569	Approved
0.6184	Remote Similarity	NPD2567	Approved
0.6164	Remote Similarity	NPD5049	Phase 3
0.6164	Remote Similarity	NPD2186	Approved
0.6159	Remote Similarity	NPD5353	Approved
0.6154	Remote Similarity	NPD7003	Approved
0.6154	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD7784	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD4110	Phase 3
0.6149	Remote Similarity	NPD2651	Approved
0.6149	Remote Similarity	NPD2649	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