NPASS Compound

Structure

NPC42586 OpenBabel07101718202D 23 25 0 0 1 0 0 0 0 0999 V2000 -5.9868 -3.2742 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1208 1.2258 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9868 -2.2742 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3853 0.7173 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3887 -2.7742 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2548 -3.2742 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3887 -1.7742 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9868 -0.2742 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5817 0.1741 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9868 -1.2742 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2888 -0.5330 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2574 -1.0183 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1208 -2.7742 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1208 0.2258 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6158 -0.0847 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2548 -1.2742 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.2588 -0.9659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8387 0.5446 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.1208 -1.7742 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.2548 -0.2742 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.3705 -1.7431 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8910 1.5433 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 13 1 0 0 0 0 2 14 1 0 0 0 0 5 6 1 0 0 0 0 5 7 1 0 0 0 0 6 13 2 0 0 0 0 7 16 1 0 0 0 0 8 10 1 0 0 0 0 8 14 1 0 0 0 0 9 11 1 0 0 0 0 9 15 1 0 0 0 0 10 19 1 0 0 0 0 11 20 1 0 0 0 0 12 15 2 0 0 0 0 12 17 1 0 0 0 0 13 19 1 0 0 0 0 14 20 1 1 0 0 0 15 18 1 0 0 0 0 16 19 1 1 0 0 0 16 20 1 0 0 0 0 17 21 2 0 0 0 0 17 23 1 0 0 0 0 18 22 1 1 0 0 0 18 23 1 0 0 0 0 19 3 1 1 0 0 0 20 4 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	318.22
Volume:	347.268
LogP:	4.643
LogD:	4.079
LogS:	-4.177
# Rotatable Bonds:	3
TPSA:	53.6
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.731
Synthetic Accessibility Score:	4.548
Fsp3:	0.7
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.969
MDCK Permeability:	1.973566941160243e-05
Pgp-inhibitor:	0.003
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.101
30% Bioavailability (F30%):	0.111

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.065
Plasma Protein Binding (PPB):	98.24524688720703%
Volume Distribution (VD):	2.891
Pgp-substrate:	3.1305453777313232%

ADMET: Metabolism

CYP1A2-inhibitor:	0.122
CYP1A2-substrate:	0.696
CYP2C19-inhibitor:	0.056
CYP2C19-substrate:	0.65
CYP2C9-inhibitor:	0.236
CYP2C9-substrate:	0.9
CYP2D6-inhibitor:	0.154
CYP2D6-substrate:	0.785
CYP3A4-inhibitor:	0.186
CYP3A4-substrate:	0.145

ADMET: Excretion

Clearance (CL):	8.283
Half-life (T1/2):	0.565

ADMET: Toxicity

hERG Blockers:	0.008
Human Hepatotoxicity (H-HT):	0.109
Drug-inuced Liver Injury (DILI):	0.019
AMES Toxicity:	0.004
Rat Oral Acute Toxicity:	0.089
Maximum Recommended Daily Dose:	0.114
Skin Sensitization:	0.478
Carcinogencity:	0.108
Eye Corrosion:	0.47
Eye Irritation:	0.859
Respiratory Toxicity:	0.894

Download Data

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

Natural Product: NPC42586

Natural Product ID:	NPC42586
*Common Name:**	16Alpha-Hydroxycleroda-3,13-Dien-15-16-Olide
IUPAC Name:	(2S)-3-[2-[(1S,2R,4aR,8aR)-1,2,4a,5-tetramethyl-2,3,4,7,8,8a-hexahydronaphthalen-1-yl]ethyl]-2-hydroxy-2H-furan-5-one
Synonyms:
Standard InCHIKey:	LVSCWEDTMWAASP-KXAOQFNBSA-N
Standard InCHI:	InChI=1S/C20H30O3/c1-13-6-5-7-16-19(13,3)10-8-14(2)20(16,4)11-9-15-12-17(21)23-18(15)22/h6,12,14,16,18,22H,5,7-11H2,1-4H3/t14-,16+,18+,19+,20+/m1/s1
SMILES:	CC1=CCC[C@H]2[C@@]1(C)CC[C@@H](C)[C@]2(C)CCC1=CC(=O)O[C@@H]1O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL486985
PubChem CID:	44224156
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones [CHEMONTID:0001538] Diterpene lactones

*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
NPO30067.1	Polyalthia longifolia var. pendula	Varieties	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11087586]
NPO30067.1	Polyalthia longifolia var. pendula	Varieties	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19860383]
NPO30067	Polyalthia longifolia	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21872367]
NPO30067	Polyalthia longifolia	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[2292689]
NPO30067.1	Polyalthia longifolia var. pendula	Varieties	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25747495]
NPO30067.1	Polyalthia longifolia var. pendula	Varieties	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO30067	Polyalthia longifolia	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]

☑ 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	5
Others	42

Activity Type	# Activity
Cell Line	3
Individual Protein	7
NON-MOLECULAR	1
Organism	35
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT196	Cell Line	AGS	Homo sapiens	IC50	=	26900.0	nM	PMID[509847]
NPT579	Cell Line	DLD-1	Homo sapiens	IC50	>	30000.0	nM	PMID[509847]
NPT65	Cell Line	HepG2	Homo sapiens	IC50	>	30000.0	nM	PMID[509847]
NPT253	Individual Protein	HMG-CoA reductase	Homo sapiens	IC50	=	30200.0	nM	PMID[509848]
NPT253	Individual Protein	HMG-CoA reductase	Homo sapiens	Inhibition	=	-78.03	%	PMID[509848]
NPT253	Individual Protein	HMG-CoA reductase	Homo sapiens	Inhibition	=	-66.09	%	PMID[509848]
NPT253	Individual Protein	HMG-CoA reductase	Homo sapiens	Inhibition	=	-62.65	%	PMID[509848]
NPT253	Individual Protein	HMG-CoA reductase	Homo sapiens	Inhibition	=	-41.11	%	PMID[509848]
NPT253	Individual Protein	HMG-CoA reductase	Homo sapiens	Inhibition	=	-28.68	%	PMID[509848]
NPT253	Individual Protein	HMG-CoA reductase	Homo sapiens	Inhibition	=	-22.65	%	PMID[509848]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	23600.0	nM	PMID[509847]
NPT2632	Organism	Syrian golden hamster	Mesocricetus auratus	MRT	=	4.52	hr	PMID[509848]
NPT2632	Organism	Syrian golden hamster	Mesocricetus auratus	CL/F	=	72.5	mL.min-1.kg-1	PMID[509848]
NPT2632	Organism	Syrian golden hamster	Mesocricetus auratus	Vd	=	17.78	L.kg-1	PMID[509848]
NPT2632	Organism	Syrian golden hamster	Mesocricetus auratus	AUC	=	5743.0	ng.hr.mL-1	PMID[509848]
NPT2632	Organism	Syrian golden hamster	Mesocricetus auratus	Cmax	=	2.487	ug.mL-1	PMID[509848]
NPT2632	Organism	Syrian golden hamster	Mesocricetus auratus	Tmax	=	0.5	hr	PMID[509848]
NPT2632	Organism	Syrian golden hamster	Mesocricetus auratus	Ratio	=	46.0	n.a.	PMID[509848]
NPT2632	Organism	Syrian golden hamster	Mesocricetus auratus	Ratio	=	54.0	n.a.	PMID[509848]
NPT2632	Organism	Syrian golden hamster	Mesocricetus auratus	Ratio	=	48.0	n.a.	PMID[509848]
NPT2632	Organism	Syrian golden hamster	Mesocricetus auratus	Ratio	=	12.0	n.a.	PMID[509848]
NPT2632	Organism	Syrian golden hamster	Mesocricetus auratus	Activity	=	43.0	%	PMID[509848]
NPT2632	Organism	Syrian golden hamster	Mesocricetus auratus	Activity	=	48.0	%	PMID[509848]
NPT2632	Organism	Syrian golden hamster	Mesocricetus auratus	Activity	=	37.0	%	PMID[509848]
NPT2632	Organism	Syrian golden hamster	Mesocricetus auratus	Activity	=	5.0	%	PMID[509848]
NPT2632	Organism	Syrian golden hamster	Mesocricetus auratus	Activity	=	10.0	%	PMID[509848]
NPT2632	Organism	Syrian golden hamster	Mesocricetus auratus	Activity	=	54.0	%	PMID[509848]
NPT2632	Organism	Syrian golden hamster	Mesocricetus auratus	Activity	=	55.0	%	PMID[509848]
NPT2632	Organism	Syrian golden hamster	Mesocricetus auratus	Activity	=	41.0	%	PMID[509848]
NPT2632	Organism	Syrian golden hamster	Mesocricetus auratus	Activity	=	23.0	%	PMID[509848]
NPT2632	Organism	Syrian golden hamster	Mesocricetus auratus	Activity	=	27.0	%	PMID[509848]
NPT2632	Organism	Syrian golden hamster	Mesocricetus auratus	Activity	=	46.0	%	PMID[509848]
NPT2632	Organism	Syrian golden hamster	Mesocricetus auratus	Activity	=	45.0	%	PMID[509848]
NPT2632	Organism	Syrian golden hamster	Mesocricetus auratus	Activity	=	26.0	%	PMID[509848]
NPT2632	Organism	Syrian golden hamster	Mesocricetus auratus	Activity	=	19.0	%	PMID[509848]
NPT20	Organism	Candida albicans	Candida albicans	Activity	=	25.14	uM	PMID[509849]
NPT27	Others	Unspecified		Activity	<	15.0	%	PMID[509849]
NPT3644	Organism	Neurospora crassa	Neurospora crassa	MIC90	=	201200.0	nM	PMID[509849]
NPT637	Organism	Fusarium oxysporum	Fusarium oxysporum	MIC90	=	805000.0	nM	PMID[509849]
NPT21	Organism	Aspergillus niger	Aspergillus niger	MIC90	=	805000.0	nM	PMID[509849]
NPT87	Organism	Aspergillus fumigatus	Aspergillus fumigatus	MIC90	=	805000.0	nM	PMID[509849]
NPT85	Organism	Filobasidiella neoformans	Cryptococcus neoformans	MIC90	=	100600.0	nM	PMID[509849]
NPT554	Organism	Candida glabrata	Candida glabrata	MIC90	=	805000.0	nM	PMID[509849]
NPT20	Organism	Candida albicans	Candida albicans	MIC90	=	805000.0	nM	PMID[509849]
NPT20	Organism	Candida albicans	Candida albicans	MIC90	=	50300.0	nM	PMID[509849]

☑ 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 NPC42586 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	160
0.1-0.2	1199
0.2-0.3	4969
0.3-0.4	14232
0.4-0.5	9832
0.5-0.6	7063
0.6-0.7	4314
0.7-0.8	827
0.8-0.85	71
0.85-0.9	23
0.9-0.95	3
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC473251
0.9518	High Similarity	NPC470734
0.9294	High Similarity	NPC477122
0.9167	High Similarity	NPC472810
0.9167	High Similarity	NPC472809
0.908	High Similarity	NPC298973
0.908	High Similarity	NPC104925
0.9024	High Similarity	NPC472440
0.8953	High Similarity	NPC477782
0.8929	High Similarity	NPC474062
0.8916	High Similarity	NPC470800
0.8864	High Similarity	NPC469697
0.8864	High Similarity	NPC324078
0.8851	High Similarity	NPC472811
0.8851	High Similarity	NPC477783
0.8837	High Similarity	NPC251528
0.881	High Similarity	NPC472442
0.8795	High Similarity	NPC311070
0.8764	High Similarity	NPC472441
0.875	High Similarity	NPC472812
0.875	High Similarity	NPC473756
0.8721	High Similarity	NPC474629
0.869	High Similarity	NPC471302
0.869	High Similarity	NPC471301
0.8675	High Similarity	NPC471298
0.8667	High Similarity	NPC162346
0.8652	High Similarity	NPC470255
0.8588	High Similarity	NPC329630
0.8571	High Similarity	NPC477718
0.8571	High Similarity	NPC471297
0.8571	High Similarity	NPC477719
0.8539	High Similarity	NPC166346
0.8537	High Similarity	NPC17550
0.8537	High Similarity	NPC242767
0.8523	High Similarity	NPC232426
0.8523	High Similarity	NPC281942
0.8506	High Similarity	NPC472378
0.8488	Intermediate Similarity	NPC471219
0.8462	Intermediate Similarity	NPC470801
0.8444	Intermediate Similarity	NPC474554
0.8427	Intermediate Similarity	NPC329842
0.8427	Intermediate Similarity	NPC141831
0.8409	Intermediate Similarity	NPC5509
0.8391	Intermediate Similarity	NPC312561
0.8387	Intermediate Similarity	NPC324841
0.8387	Intermediate Similarity	NPC477716
0.8387	Intermediate Similarity	NPC477721
0.8387	Intermediate Similarity	NPC477720
0.8372	Intermediate Similarity	NPC471795
0.8372	Intermediate Similarity	NPC86316
0.8372	Intermediate Similarity	NPC106416
0.837	Intermediate Similarity	NPC475709
0.8353	Intermediate Similarity	NPC477124
0.8353	Intermediate Similarity	NPC472377
0.8353	Intermediate Similarity	NPC42476
0.8333	Intermediate Similarity	NPC115021
0.8315	Intermediate Similarity	NPC78973
0.8298	Intermediate Similarity	NPC477717
0.8276	Intermediate Similarity	NPC131813
0.8261	Intermediate Similarity	NPC17578
0.8261	Intermediate Similarity	NPC240673
0.8256	Intermediate Similarity	NPC71626
0.8256	Intermediate Similarity	NPC126518
0.8242	Intermediate Similarity	NPC474555
0.8235	Intermediate Similarity	NPC323251
0.8235	Intermediate Similarity	NPC324170
0.8222	Intermediate Similarity	NPC165904
0.8222	Intermediate Similarity	NPC179517
0.8214	Intermediate Similarity	NPC10636
0.8211	Intermediate Similarity	NPC472815
0.8202	Intermediate Similarity	NPC174342
0.8182	Intermediate Similarity	NPC475678
0.8182	Intermediate Similarity	NPC471796
0.8172	Intermediate Similarity	NPC98112
0.8161	Intermediate Similarity	NPC30984
0.8161	Intermediate Similarity	NPC65661
0.8161	Intermediate Similarity	NPC217394
0.8161	Intermediate Similarity	NPC163606
0.8161	Intermediate Similarity	NPC119001
0.8132	Intermediate Similarity	NPC472303
0.8132	Intermediate Similarity	NPC242069
0.8111	Intermediate Similarity	NPC221111
0.8111	Intermediate Similarity	NPC280149
0.8111	Intermediate Similarity	NPC469403
0.8111	Intermediate Similarity	NPC182136
0.8105	Intermediate Similarity	NPC63249
0.8085	Intermediate Similarity	NPC474440
0.8068	Intermediate Similarity	NPC173917
0.8068	Intermediate Similarity	NPC118266
0.8065	Intermediate Similarity	NPC165632
0.8046	Intermediate Similarity	NPC474693
0.8025	Intermediate Similarity	NPC476490
0.8025	Intermediate Similarity	NPC476489
0.8023	Intermediate Similarity	NPC122945
0.8023	Intermediate Similarity	NPC256112
0.8023	Intermediate Similarity	NPC471218
0.8023	Intermediate Similarity	NPC109938
0.8022	Intermediate Similarity	NPC65513
0.8022	Intermediate Similarity	NPC177037
0.8022	Intermediate Similarity	NPC289479
0.8022	Intermediate Similarity	NPC472814
0.8021	Intermediate Similarity	NPC134077
0.8	Intermediate Similarity	NPC474396
0.8	Intermediate Similarity	NPC50488
0.8	Intermediate Similarity	NPC476767
0.8	Intermediate Similarity	NPC472826
0.8	Intermediate Similarity	NPC168131
0.8	Intermediate Similarity	NPC206062
0.7979	Intermediate Similarity	NPC208094
0.7955	Intermediate Similarity	NPC471300
0.7955	Intermediate Similarity	NPC475860
0.7955	Intermediate Similarity	NPC474860
0.7955	Intermediate Similarity	NPC473659
0.7955	Intermediate Similarity	NPC474694
0.7955	Intermediate Similarity	NPC189311
0.7935	Intermediate Similarity	NPC53555
0.7935	Intermediate Similarity	NPC469939
0.7931	Intermediate Similarity	NPC476927
0.7931	Intermediate Similarity	NPC474809
0.7917	Intermediate Similarity	NPC471075
0.7912	Intermediate Similarity	NPC253186
0.7912	Intermediate Similarity	NPC51486
0.7912	Intermediate Similarity	NPC470817
0.7912	Intermediate Similarity	NPC310479
0.7907	Intermediate Similarity	NPC475944
0.7895	Intermediate Similarity	NPC473154
0.7865	Intermediate Similarity	NPC329692
0.7857	Intermediate Similarity	NPC316500
0.7857	Intermediate Similarity	NPC262747
0.7849	Intermediate Similarity	NPC105490
0.7849	Intermediate Similarity	NPC477722
0.7849	Intermediate Similarity	NPC475572
0.7841	Intermediate Similarity	NPC318515
0.7816	Intermediate Similarity	NPC200513
0.7816	Intermediate Similarity	NPC2524
0.7812	Intermediate Similarity	NPC20113
0.7812	Intermediate Similarity	NPC477968
0.7812	Intermediate Similarity	NPC161527
0.7812	Intermediate Similarity	NPC477972
0.7812	Intermediate Similarity	NPC472644
0.7812	Intermediate Similarity	NPC219285
0.7812	Intermediate Similarity	NPC477971
0.7812	Intermediate Similarity	NPC228251
0.7802	Intermediate Similarity	NPC293044
0.7802	Intermediate Similarity	NPC470819
0.78	Intermediate Similarity	NPC470024
0.78	Intermediate Similarity	NPC476765
0.78	Intermediate Similarity	NPC38948
0.7791	Intermediate Similarity	NPC281880
0.7789	Intermediate Similarity	NPC476253
0.7778	Intermediate Similarity	NPC166857
0.7778	Intermediate Similarity	NPC172867
0.7766	Intermediate Similarity	NPC276110
0.7766	Intermediate Similarity	NPC295347
0.7765	Intermediate Similarity	NPC209135
0.7765	Intermediate Similarity	NPC474816
0.7755	Intermediate Similarity	NPC120009
0.7753	Intermediate Similarity	NPC35933
0.7753	Intermediate Similarity	NPC109528
0.7753	Intermediate Similarity	NPC474013
0.775	Intermediate Similarity	NPC476945
0.7742	Intermediate Similarity	NPC205034
0.7742	Intermediate Similarity	NPC7349
0.7742	Intermediate Similarity	NPC162615
0.7742	Intermediate Similarity	NPC472641
0.7742	Intermediate Similarity	NPC472640
0.7742	Intermediate Similarity	NPC139692
0.7742	Intermediate Similarity	NPC152778
0.7732	Intermediate Similarity	NPC472643
0.7732	Intermediate Similarity	NPC198992
0.7727	Intermediate Similarity	NPC193198
0.7727	Intermediate Similarity	NPC22611
0.7727	Intermediate Similarity	NPC23748
0.7723	Intermediate Similarity	NPC206618
0.7717	Intermediate Similarity	NPC472642
0.7708	Intermediate Similarity	NPC325229
0.7708	Intermediate Similarity	NPC275086
0.7708	Intermediate Similarity	NPC181147
0.7701	Intermediate Similarity	NPC229584
0.7701	Intermediate Similarity	NPC40228
0.7701	Intermediate Similarity	NPC14203
0.7701	Intermediate Similarity	NPC170303
0.7701	Intermediate Similarity	NPC159148
0.77	Intermediate Similarity	NPC475074
0.77	Intermediate Similarity	NPC109376
0.7692	Intermediate Similarity	NPC226863
0.7684	Intermediate Similarity	NPC242848
0.7684	Intermediate Similarity	NPC112654
0.7684	Intermediate Similarity	NPC325960
0.7684	Intermediate Similarity	NPC134072
0.7684	Intermediate Similarity	NPC319692
0.7684	Intermediate Similarity	NPC190713
0.7684	Intermediate Similarity	NPC234993
0.7684	Intermediate Similarity	NPC473153
0.7677	Intermediate Similarity	NPC472819
0.766	Intermediate Similarity	NPC53685
0.766	Intermediate Similarity	NPC57117
0.7653	Intermediate Similarity	NPC471363
0.7653	Intermediate Similarity	NPC238397
0.7647	Intermediate Similarity	NPC54996

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 NPC42586 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	142
0.1-0.2	1519
0.2-0.3	4034
0.3-0.4	2423
0.4-0.5	621
0.5-0.6	276
0.6-0.7	129
0.7-0.8	6
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
0.8256	Intermediate Similarity	NPD6400	Clinical (unspecified phase)
0.7816	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7451	Intermediate Similarity	NPD6686	Approved
0.7449	Intermediate Similarity	NPD7640	Approved
0.7449	Intermediate Similarity	NPD7639	Approved
0.7347	Intermediate Similarity	NPD4225	Approved
0.7347	Intermediate Similarity	NPD7638	Approved
0.7053	Intermediate Similarity	NPD6051	Approved
0.7	Intermediate Similarity	NPD7327	Approved
0.7	Intermediate Similarity	NPD7328	Approved
0.6989	Remote Similarity	NPD1694	Approved
0.6937	Remote Similarity	NPD7516	Approved
0.6915	Remote Similarity	NPD7334	Approved
0.6915	Remote Similarity	NPD5330	Approved
0.6915	Remote Similarity	NPD6409	Approved
0.6915	Remote Similarity	NPD7146	Approved
0.6915	Remote Similarity	NPD6684	Approved
0.6915	Remote Similarity	NPD7521	Approved
0.69	Remote Similarity	NPD6084	Phase 2
0.69	Remote Similarity	NPD6083	Phase 2
0.6882	Remote Similarity	NPD3133	Approved
0.6882	Remote Similarity	NPD3665	Phase 1
0.6882	Remote Similarity	NPD3666	Approved
0.6875	Remote Similarity	NPD8377	Approved
0.6875	Remote Similarity	NPD8294	Approved
0.6869	Remote Similarity	NPD5695	Phase 3
0.6814	Remote Similarity	NPD8380	Approved
0.6814	Remote Similarity	NPD8296	Approved
0.6814	Remote Similarity	NPD8379	Approved
0.6814	Remote Similarity	NPD7503	Approved
0.6814	Remote Similarity	NPD8335	Approved
0.6814	Remote Similarity	NPD8378	Approved
0.6814	Remote Similarity	NPD8033	Approved
0.6796	Remote Similarity	NPD7632	Discontinued
0.6771	Remote Similarity	NPD6672	Approved
0.6771	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6771	Remote Similarity	NPD5737	Approved
0.6771	Remote Similarity	NPD6903	Approved
0.6768	Remote Similarity	NPD7748	Approved
0.6742	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6737	Remote Similarity	NPD3618	Phase 1
0.6737	Remote Similarity	NPD4519	Discontinued
0.6737	Remote Similarity	NPD4623	Approved
0.6735	Remote Similarity	NPD7515	Phase 2
0.6735	Remote Similarity	NPD5693	Phase 1
0.6703	Remote Similarity	NPD4195	Approved
0.6698	Remote Similarity	NPD6412	Phase 2
0.6667	Remote Similarity	NPD6399	Phase 3
0.6667	Remote Similarity	NPD3667	Approved
0.6667	Remote Similarity	NPD5696	Approved
0.6629	Remote Similarity	NPD6942	Approved
0.6629	Remote Similarity	NPD7339	Approved
0.6629	Remote Similarity	NPD8039	Approved
0.6627	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.6607	Remote Similarity	NPD7115	Discovery
0.6585	Remote Similarity	NPD4191	Approved
0.6585	Remote Similarity	NPD4193	Approved
0.6585	Remote Similarity	NPD4194	Approved
0.6585	Remote Similarity	NPD4192	Approved
0.6581	Remote Similarity	NPD7507	Approved
0.6574	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6569	Remote Similarity	NPD7902	Approved
0.6566	Remote Similarity	NPD7637	Suspended
0.6562	Remote Similarity	NPD5279	Phase 3
0.6548	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6531	Remote Similarity	NPD4753	Phase 2
0.6531	Remote Similarity	NPD5328	Approved
0.6526	Remote Similarity	NPD4786	Approved
0.6522	Remote Similarity	NPD7645	Phase 2
0.6495	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6489	Remote Similarity	NPD4221	Approved
0.6489	Remote Similarity	NPD4223	Phase 3
0.6465	Remote Similarity	NPD5785	Approved
0.6456	Remote Similarity	NPD342	Phase 1
0.6449	Remote Similarity	NPD7128	Approved
0.6449	Remote Similarity	NPD6402	Approved
0.6449	Remote Similarity	NPD6675	Approved
0.6449	Remote Similarity	NPD5739	Approved
0.6444	Remote Similarity	NPD8264	Approved
0.6442	Remote Similarity	NPD6404	Discontinued
0.6429	Remote Similarity	NPD5208	Approved
0.6421	Remote Similarity	NPD6695	Phase 3
0.6417	Remote Similarity	NPD7319	Approved
0.64	Remote Similarity	NPD5281	Approved
0.64	Remote Similarity	NPD5284	Approved
0.64	Remote Similarity	NPD6079	Approved
0.6396	Remote Similarity	NPD6882	Approved
0.6389	Remote Similarity	NPD5701	Approved
0.6389	Remote Similarity	NPD5697	Approved
0.6381	Remote Similarity	NPD5344	Discontinued
0.6364	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD6080	Approved
0.6364	Remote Similarity	NPD6904	Approved
0.6364	Remote Similarity	NPD6673	Approved
0.6354	Remote Similarity	NPD4197	Approved
0.6354	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6346	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6344	Remote Similarity	NPD6929	Approved
0.6337	Remote Similarity	NPD5779	Approved
0.6337	Remote Similarity	NPD4202	Approved
0.6337	Remote Similarity	NPD5778	Approved
0.6333	Remote Similarity	NPD6924	Approved
0.6333	Remote Similarity	NPD6926	Approved
0.633	Remote Similarity	NPD7320	Approved
0.633	Remote Similarity	NPD6899	Approved
0.633	Remote Similarity	NPD6881	Approved
0.633	Remote Similarity	NPD6011	Approved
0.6327	Remote Similarity	NPD3573	Approved
0.63	Remote Similarity	NPD5207	Approved
0.63	Remote Similarity	NPD5692	Phase 3
0.6292	Remote Similarity	NPD4243	Approved
0.6289	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6289	Remote Similarity	NPD5329	Approved
0.6289	Remote Similarity	NPD1696	Phase 3
0.6277	Remote Similarity	NPD4695	Discontinued
0.6277	Remote Similarity	NPD7525	Registered
0.6277	Remote Similarity	NPD6931	Approved
0.6277	Remote Similarity	NPD6930	Phase 2
0.6275	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6275	Remote Similarity	NPD7900	Approved
0.6273	Remote Similarity	NPD6013	Approved
0.6273	Remote Similarity	NPD6014	Approved
0.6273	Remote Similarity	NPD6012	Approved
0.6273	Remote Similarity	NPD6373	Approved
0.6273	Remote Similarity	NPD6372	Approved
0.625	Remote Similarity	NPD6053	Discontinued
0.6238	Remote Similarity	NPD6050	Approved
0.6238	Remote Similarity	NPD5694	Approved
0.6238	Remote Similarity	NPD6411	Approved
0.6237	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6237	Remote Similarity	NPD3617	Approved
0.6237	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6224	Remote Similarity	NPD4694	Approved
0.6224	Remote Similarity	NPD5205	Approved
0.6224	Remote Similarity	NPD4138	Approved
0.6224	Remote Similarity	NPD5280	Approved
0.6224	Remote Similarity	NPD4693	Phase 3
0.6224	Remote Similarity	NPD5690	Phase 2
0.6224	Remote Similarity	NPD6098	Approved
0.6224	Remote Similarity	NPD4690	Approved
0.6224	Remote Similarity	NPD4688	Approved
0.6224	Remote Similarity	NPD4689	Approved
0.6216	Remote Similarity	NPD7290	Approved
0.6216	Remote Similarity	NPD6883	Approved
0.6216	Remote Similarity	NPD7102	Approved
0.6214	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6214	Remote Similarity	NPD5210	Approved
0.6214	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6214	Remote Similarity	NPD4629	Approved
0.62	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6196	Remote Similarity	NPD6933	Approved
0.619	Remote Similarity	NPD368	Approved
0.6168	Remote Similarity	NPD5211	Phase 2
0.6162	Remote Similarity	NPD7524	Approved
0.6162	Remote Similarity	NPD7750	Discontinued
0.6161	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6161	Remote Similarity	NPD6650	Approved
0.6161	Remote Similarity	NPD6617	Approved
0.6161	Remote Similarity	NPD8130	Phase 1
0.6161	Remote Similarity	NPD6649	Approved
0.6161	Remote Similarity	NPD6869	Approved
0.6161	Remote Similarity	NPD6847	Approved
0.6154	Remote Similarity	NPD5222	Approved
0.6154	Remote Similarity	NPD5221	Approved
0.6154	Remote Similarity	NPD4785	Approved
0.6154	Remote Similarity	NPD4784	Approved
0.6154	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD4697	Phase 3
0.6146	Remote Similarity	NPD5209	Approved
0.6139	Remote Similarity	NPD46	Approved
0.6139	Remote Similarity	NPD6698	Approved
0.6139	Remote Similarity	NPD7838	Discovery
0.6132	Remote Similarity	NPD6648	Approved
0.6129	Remote Similarity	NPD6925	Approved
0.6129	Remote Similarity	NPD5776	Phase 2
0.6122	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6117	Remote Similarity	NPD6001	Approved
0.6106	Remote Similarity	NPD8297	Approved
0.6105	Remote Similarity	NPD7332	Phase 2
0.6105	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6105	Remote Similarity	NPD7514	Phase 3
0.6095	Remote Similarity	NPD5173	Approved
0.6095	Remote Similarity	NPD4755	Approved
0.6091	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6087	Remote Similarity	NPD5275	Approved
0.6087	Remote Similarity	NPD4190	Phase 3
0.6082	Remote Similarity	NPD7154	Phase 3
0.6082	Remote Similarity	NPD5362	Discontinued
0.6067	Remote Similarity	NPD6922	Approved
0.6067	Remote Similarity	NPD6923	Approved
0.6064	Remote Similarity	NPD7145	Approved
0.6061	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6055	Remote Similarity	NPD5141	Approved
0.6053	Remote Similarity	NPD8133	Approved
0.6042	Remote Similarity	NPD6902	Approved
0.604	Remote Similarity	NPD6101	Approved
0.604	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6038	Remote Similarity	NPD5290	Discontinued
0.6034	Remote Similarity	NPD6009	Approved
0.602	Remote Similarity	NPD3668	Phase 3

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