NPASS Compound

Structure

CID324078 OpenBabel06191716172D 34 36 0 0 1 0 0 0 0 0999 V2000 2.8660 -8.0622 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0000 -8.5622 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5000 -4.9641 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5000 -4.9641 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 -6.6962 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5000 -3.2321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5000 -3.2321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0000 -4.0981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0000 -4.0981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5000 -6.6962 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0000 -7.5622 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0000 -5.8301 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0000 -5.8301 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0878 -4.0411 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0000 -2.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5000 -3.2321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5000 -3.2321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0000 -4.0981 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5000 -6.6962 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5000 -4.9641 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 8.0388 -3.7321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0878 -2.4230 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.0000 -7.5622 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5000 -4.9641 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.0000 -5.8301 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 8.8479 -4.3198 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.7788 -1.4720 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5000 -2.5000 0.0000 O 0 5 0 0 0 0 0 0 0 0 0 0 1.5000 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5000 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5000 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 8.0388 -2.7321 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5000 -1.5000 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 1.9742 2.3810 0.0000 Na 0 3 0 0 0 15 0 0 0 0 0 0 1 23 1 0 0 0 0 2 23 1 0 0 0 0 5 11 1 0 0 0 0 5 12 1 0 0 0 0 6 8 1 0 0 0 0 6 16 1 0 0 0 0 7 9 1 0 0 0 0 7 17 1 0 0 0 0 8 18 1 0 0 0 0 9 20 1 0 0 0 0 10 13 1 0 0 0 0 10 19 1 0 0 0 0 11 23 1 0 0 0 0 12 25 1 0 0 0 0 13 24 1 0 0 0 0 14 16 2 0 0 0 0 14 21 1 0 0 0 0 15 17 2 0 0 0 0 15 31 1 0 0 0 0 16 22 1 0 0 0 0 17 18 1 0 0 0 0 18 24 1 6 0 0 0 19 23 1 0 0 0 0 19 25 1 1 0 0 0 20 24 1 1 0 0 0 20 25 1 0 0 0 0 21 26 2 0 0 0 0 21 32 1 0 0 0 0 22 27 1 1 0 0 0 22 32 1 0 0 0 0 24 3 1 6 0 0 0 25 4 1 1 0 0 0 28 33 1 0 0 0 0 29 33 2 0 0 0 0 30 33 2 0 0 0 0 31 33 1 0 0 0 0 M CHG 2 28 -1 34 1 M END $$$$

Physi-Chem Properties

Molecular Weight:	481.23
Volume:	477.543
LogP:	4.605
LogD:	3.689
LogS:	-3.634
# Rotatable Bonds:	5
TPSA:	120.03
# H-Bond Aceptor:	7
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.317
Synthetic Accessibility Score:	5.064
Fsp3:	0.76
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-5.392
MDCK Permeability:	1.695840182946995e-05
Pgp-inhibitor:	0.026
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.015
20% Bioavailability (F20%):	0.005
30% Bioavailability (F30%):	0.154

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.059
Plasma Protein Binding (PPB):	96.7732162475586%
Volume Distribution (VD):	1.096
Pgp-substrate:	1.7328890562057495%

ADMET: Metabolism

CYP1A2-inhibitor:	0.018
CYP1A2-substrate:	0.389
CYP2C19-inhibitor:	0.029
CYP2C19-substrate:	0.248
CYP2C9-inhibitor:	0.348
CYP2C9-substrate:	0.874
CYP2D6-inhibitor:	0.078
CYP2D6-substrate:	0.696
CYP3A4-inhibitor:	0.148
CYP3A4-substrate:	0.144

ADMET: Excretion

Clearance (CL):	1.954
Half-life (T1/2):	0.098

ADMET: Toxicity

hERG Blockers:	0.009
Human Hepatotoxicity (H-HT):	0.934
Drug-inuced Liver Injury (DILI):	0.033
AMES Toxicity:	0.007
Rat Oral Acute Toxicity:	0.548
Maximum Recommended Daily Dose:	0.967
Skin Sensitization:	0.741
Carcinogencity:	0.951
Eye Corrosion:	0.004
Eye Irritation:	0.188
Respiratory Toxicity:	0.964

Download Data

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

Natural Product: NPC324078

Natural Product ID:	NPC324078
*Common Name:**	Sodium(E)-((1R,4As,4Bs,8As,10As)-1-(2-((S)-2-Hydroxy-5-Oxo-2,5-Dihydrofuran-3-Yl)Ethyl)-4B,8,8,10A-Tetramethyldecahydrophenanthren-2(1H,3H,4Bh)-Ylidene)Methyl Sulfate
IUPAC Name:	sodium;[(E)-[(1R,4aR,4bS,8aS,10aS)-1-[2-[(2S)-2-hydroxy-5-oxo-2H-furan-3-yl]ethyl]-4b,8,8,10a-tetramethyl-1,3,4,4a,5,6,7,8a,9,10-decahydrophenanthren-2-ylidene]methyl] sulfate
Synonyms:
Standard InCHIKey:	MSWLPMNAMZJYJW-CGSXWFLESA-M
Standard InCHI:	InChI=1S/C25H38O7S.Na/c1-23(2)11-5-12-25(4)19(23)10-13-24(3)18(8-6-16-14-21(26)32-22(16)27)17(7-9-20(24)25)15-31-33(28,29)30;/h14-15,18-20,22,27H,5-13H2,1-4H3,(H,28,29,30);/q;+1/p-1/b17-15+;/t18-,19-,20-,22-,24+,25-;/m0./s1
SMILES:	CC1(CCCC2(C1CCC3(C2CCC(=COS(=O)(=O)[O-])C3CCC4=CC(=O)OC4O)C)C)C.[Na+]
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1818100
PubChem CID:	56666216
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001552] Sesterterpenoids [CHEMONTID:0002881] Cheilanthane sesterterpenoids

*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
NPO30318	Coscinoderma	Genus	Spongiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[21827183]

☑ 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	3
MIC	10
Others	1

Activity Type	# Activity
Cell Line	1
Individual Protein	2
Organism	10
Protein Complex	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT111	Cell Line	K562	Homo sapiens	LC50	=	59000.0	nM	PMID[506741]
NPT1821	Individual Protein	Sortase	Staphylococcus aureus	IC50	>	200000.0	nM	PMID[506741]
NPT1087	Individual Protein	Isocitrate lyase	Candida albicans	IC50	=	56000.0	nM	PMID[506741]
NPT2890	Protein Complex	Sodium/potassium-transporting ATPase	Homo sapiens	IC50	=	5000.0	nM	PMID[506741]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>	100.0	ug.mL-1	PMID[506741]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	>	100.0	ug.mL-1	PMID[506741]
NPT729	Organism	Micrococcus luteus	Micrococcus luteus	MIC	>	100.0	ug.mL-1	PMID[506741]
NPT566	Organism	Salmonella typhimurium	Salmonella enterica subsp. enterica serovar Typhimurium	MIC	>	100.0	ug.mL-1	PMID[506741]
NPT766	Organism	Proteus vulgaris	Proteus vulgaris	MIC	>	100.0	ug.mL-1	PMID[506741]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	100.0	ug.mL-1	PMID[506741]
NPT87	Organism	Aspergillus fumigatus	Aspergillus fumigatus	MIC	>	100.0	ug.mL-1	PMID[506741]
NPT329	Organism	Trichophyton rubrum	Trichophyton rubrum	MIC	>	100.0	ug.mL-1	PMID[506741]
NPT330	Organism	Trichophyton mentagrophytes	Trichophyton mentagrophytes	MIC	>	100.0	ug.mL-1	PMID[506741]
NPT20	Organism	Candida albicans	Candida albicans	MIC	>	100.0	ug.mL-1	PMID[506741]

☑ 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 NPC324078 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	183
0.1-0.2	1397
0.2-0.3	4881
0.3-0.4	14492
0.4-0.5	9905
0.5-0.6	6915
0.6-0.7	4358
0.7-0.8	524
0.8-0.85	27
0.85-0.9	12
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9326	High Similarity	NPC477122
0.8966	High Similarity	NPC318515
0.8913	High Similarity	NPC469697
0.8864	High Similarity	NPC473251
0.8864	High Similarity	NPC42586
0.883	High Similarity	NPC477719
0.883	High Similarity	NPC477718
0.8778	High Similarity	NPC472810
0.8778	High Similarity	NPC472809
0.8723	High Similarity	NPC162346
0.8723	High Similarity	NPC319692
0.8723	High Similarity	NPC325960
0.871	High Similarity	NPC104925
0.871	High Similarity	NPC298973
0.8696	High Similarity	NPC329842
0.8681	High Similarity	NPC470734
0.8646	High Similarity	NPC477721
0.8646	High Similarity	NPC477720
0.8646	High Similarity	NPC477716
0.8636	High Similarity	NPC324243
0.8587	High Similarity	NPC477782
0.8571	High Similarity	NPC474629
0.8557	High Similarity	NPC477717
0.8495	Intermediate Similarity	NPC477783
0.8495	Intermediate Similarity	NPC472811
0.8427	Intermediate Similarity	NPC472440
0.8427	Intermediate Similarity	NPC477124
0.8421	Intermediate Similarity	NPC472441
0.8404	Intermediate Similarity	NPC472812
0.8333	Intermediate Similarity	NPC471302
0.8316	Intermediate Similarity	NPC470255
0.828	Intermediate Similarity	NPC251528
0.8265	Intermediate Similarity	NPC324841
0.8242	Intermediate Similarity	NPC472442
0.8242	Intermediate Similarity	NPC329630
0.8222	Intermediate Similarity	NPC311070
0.8211	Intermediate Similarity	NPC472303
0.8191	Intermediate Similarity	NPC78973
0.8182	Intermediate Similarity	NPC63249
0.8132	Intermediate Similarity	NPC471301
0.8125	Intermediate Similarity	NPC477722
0.8111	Intermediate Similarity	NPC471298
0.8105	Intermediate Similarity	NPC289479
0.81	Intermediate Similarity	NPC134077
0.8085	Intermediate Similarity	NPC174342
0.8081	Intermediate Similarity	NPC472826
0.8081	Intermediate Similarity	NPC476767
0.8061	Intermediate Similarity	NPC475709
0.8043	Intermediate Similarity	NPC474013
0.8043	Intermediate Similarity	NPC30984
0.8022	Intermediate Similarity	NPC471297
0.8022	Intermediate Similarity	NPC42476
0.8	Intermediate Similarity	NPC471075
0.798	Intermediate Similarity	NPC325229
0.798	Intermediate Similarity	NPC275086
0.7959	Intermediate Similarity	NPC470801
0.7957	Intermediate Similarity	NPC131813
0.7957	Intermediate Similarity	NPC173917
0.7957	Intermediate Similarity	NPC474062
0.7955	Intermediate Similarity	NPC473756
0.7935	Intermediate Similarity	NPC470800
0.7921	Intermediate Similarity	NPC472815
0.79	Intermediate Similarity	NPC477968
0.79	Intermediate Similarity	NPC219285
0.79	Intermediate Similarity	NPC20113
0.79	Intermediate Similarity	NPC228251
0.79	Intermediate Similarity	NPC161527
0.79	Intermediate Similarity	NPC477971
0.79	Intermediate Similarity	NPC477972
0.7885	Intermediate Similarity	NPC476765
0.7879	Intermediate Similarity	NPC51499
0.7849	Intermediate Similarity	NPC65661
0.7849	Intermediate Similarity	NPC86316
0.7849	Intermediate Similarity	NPC106416
0.7843	Intermediate Similarity	NPC45897
0.7843	Intermediate Similarity	NPC281378
0.7835	Intermediate Similarity	NPC246860
0.7835	Intermediate Similarity	NPC53555
0.7826	Intermediate Similarity	NPC476927
0.7812	Intermediate Similarity	NPC281942
0.7812	Intermediate Similarity	NPC232426
0.781	Intermediate Similarity	NPC476759
0.78	Intermediate Similarity	NPC473154
0.78	Intermediate Similarity	NPC474440
0.7789	Intermediate Similarity	NPC472378
0.7788	Intermediate Similarity	NPC471205
0.7788	Intermediate Similarity	NPC475074
0.7778	Intermediate Similarity	NPC242767
0.7767	Intermediate Similarity	NPC472819
0.7766	Intermediate Similarity	NPC118266
0.7755	Intermediate Similarity	NPC474554
0.7755	Intermediate Similarity	NPC105490
0.7745	Intermediate Similarity	NPC476769
0.7742	Intermediate Similarity	NPC126518
0.7736	Intermediate Similarity	NPC476766
0.7732	Intermediate Similarity	NPC120539
0.7732	Intermediate Similarity	NPC179517
0.7732	Intermediate Similarity	NPC165904
0.7732	Intermediate Similarity	NPC141831
0.7723	Intermediate Similarity	NPC251680
0.7717	Intermediate Similarity	NPC2524
0.7717	Intermediate Similarity	NPC324170
0.7717	Intermediate Similarity	NPC323251
0.7714	Intermediate Similarity	NPC38948
0.7708	Intermediate Similarity	NPC5509
0.7708	Intermediate Similarity	NPC293044
0.77	Intermediate Similarity	NPC257726
0.77	Intermediate Similarity	NPC231751
0.77	Intermediate Similarity	NPC98112
0.77	Intermediate Similarity	NPC204054
0.7692	Intermediate Similarity	NPC10636
0.7692	Intermediate Similarity	NPC472818
0.7684	Intermediate Similarity	NPC166857
0.7677	Intermediate Similarity	NPC276110
0.767	Intermediate Similarity	NPC120009
0.766	Intermediate Similarity	NPC217394
0.766	Intermediate Similarity	NPC163606
0.766	Intermediate Similarity	NPC471795
0.7653	Intermediate Similarity	NPC166346
0.7653	Intermediate Similarity	NPC7349
0.7653	Intermediate Similarity	NPC470656
0.7647	Intermediate Similarity	NPC268829
0.7647	Intermediate Similarity	NPC295110
0.7647	Intermediate Similarity	NPC247701
0.7647	Intermediate Similarity	NPC222875
0.7647	Intermediate Similarity	NPC25177
0.7642	Intermediate Similarity	NPC206618
0.7629	Intermediate Similarity	NPC51486
0.7629	Intermediate Similarity	NPC469403
0.7629	Intermediate Similarity	NPC280149
0.7629	Intermediate Similarity	NPC182136
0.7629	Intermediate Similarity	NPC253186
0.7629	Intermediate Similarity	NPC221111
0.7624	Intermediate Similarity	NPC181147
0.7624	Intermediate Similarity	NPC218107
0.7624	Intermediate Similarity	NPC278673
0.7619	Intermediate Similarity	NPC472820
0.7609	Intermediate Similarity	NPC14203
0.7609	Intermediate Similarity	NPC40228
0.7609	Intermediate Similarity	NPC170303
0.7609	Intermediate Similarity	NPC229584
0.76	Intermediate Similarity	NPC16967
0.76	Intermediate Similarity	NPC17578
0.76	Intermediate Similarity	NPC240673
0.7582	Intermediate Similarity	NPC17550
0.7579	Intermediate Similarity	NPC471219
0.7576	Intermediate Similarity	NPC201725
0.7576	Intermediate Similarity	NPC474555
0.7553	Intermediate Similarity	NPC71626
0.7551	Intermediate Similarity	NPC234335
0.7551	Intermediate Similarity	NPC472814
0.7551	Intermediate Similarity	NPC177037
0.7549	Intermediate Similarity	NPC38855
0.7549	Intermediate Similarity	NPC201406
0.7549	Intermediate Similarity	NPC117685
0.7547	Intermediate Similarity	NPC300614
0.7547	Intermediate Similarity	NPC177524
0.7547	Intermediate Similarity	NPC325054
0.7547	Intermediate Similarity	NPC90946
0.7547	Intermediate Similarity	NPC392
0.7547	Intermediate Similarity	NPC219900
0.7527	Intermediate Similarity	NPC471218
0.7527	Intermediate Similarity	NPC200513
0.7527	Intermediate Similarity	NPC256112
0.7526	Intermediate Similarity	NPC50488
0.7526	Intermediate Similarity	NPC474396
0.7525	Intermediate Similarity	NPC476768
0.7525	Intermediate Similarity	NPC97867
0.7525	Intermediate Similarity	NPC476253
0.7525	Intermediate Similarity	NPC76266
0.7525	Intermediate Similarity	NPC208094
0.7524	Intermediate Similarity	NPC218158
0.7524	Intermediate Similarity	NPC51719
0.75	Intermediate Similarity	NPC160583
0.75	Intermediate Similarity	NPC135224
0.75	Intermediate Similarity	NPC112009
0.75	Intermediate Similarity	NPC471796
0.75	Intermediate Similarity	NPC471208
0.75	Intermediate Similarity	NPC477969
0.75	Intermediate Similarity	NPC97487
0.75	Intermediate Similarity	NPC281880
0.75	Intermediate Similarity	NPC196471
0.75	Intermediate Similarity	NPC293052
0.75	Intermediate Similarity	NPC10232
0.75	Intermediate Similarity	NPC187302
0.75	Intermediate Similarity	NPC189588
0.75	Intermediate Similarity	NPC312561
0.7477	Intermediate Similarity	NPC31522
0.7477	Intermediate Similarity	NPC475030
0.7476	Intermediate Similarity	NPC11974
0.7475	Intermediate Similarity	NPC267266
0.7475	Intermediate Similarity	NPC472641
0.7475	Intermediate Similarity	NPC476304
0.7475	Intermediate Similarity	NPC139692
0.7475	Intermediate Similarity	NPC115021
0.7475	Intermediate Similarity	NPC162615
0.7475	Intermediate Similarity	NPC205034
0.7475	Intermediate Similarity	NPC38232
0.7475	Intermediate Similarity	NPC277721
0.7475	Intermediate Similarity	NPC151722

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 NPC324078 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	145
0.1-0.2	1490
0.2-0.3	4030
0.3-0.4	2501
0.4-0.5	592
0.5-0.6	299
0.6-0.7	87
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
0.7742	Intermediate Similarity	NPD6400	Clinical (unspecified phase)
0.7723	Intermediate Similarity	NPD7639	Approved
0.7723	Intermediate Similarity	NPD7640	Approved
0.7624	Intermediate Similarity	NPD7638	Approved
0.7547	Intermediate Similarity	NPD6686	Approved
0.7527	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7257	Intermediate Similarity	NPD7327	Approved
0.7257	Intermediate Similarity	NPD7328	Approved
0.7193	Intermediate Similarity	NPD7516	Approved
0.713	Intermediate Similarity	NPD8294	Approved
0.713	Intermediate Similarity	NPD8377	Approved
0.7115	Intermediate Similarity	NPD4225	Approved
0.7075	Intermediate Similarity	NPD7632	Discontinued
0.7069	Intermediate Similarity	NPD8379	Approved
0.7069	Intermediate Similarity	NPD8380	Approved
0.7069	Intermediate Similarity	NPD8378	Approved
0.7069	Intermediate Similarity	NPD8296	Approved
0.7069	Intermediate Similarity	NPD8335	Approved
0.7069	Intermediate Similarity	NPD8033	Approved
0.7	Intermediate Similarity	NPD6051	Approved
0.6923	Remote Similarity	NPD7503	Approved
0.6893	Remote Similarity	NPD7748	Approved
0.6863	Remote Similarity	NPD7515	Phase 2
0.6857	Remote Similarity	NPD6083	Phase 2
0.6857	Remote Similarity	NPD6084	Phase 2
0.6833	Remote Similarity	NPD7507	Approved
0.6733	Remote Similarity	NPD5737	Approved
0.6733	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6733	Remote Similarity	NPD6672	Approved
0.67	Remote Similarity	NPD7146	Approved
0.67	Remote Similarity	NPD6409	Approved
0.67	Remote Similarity	NPD7334	Approved
0.67	Remote Similarity	NPD6684	Approved
0.67	Remote Similarity	NPD7521	Approved
0.67	Remote Similarity	NPD5330	Approved
0.6698	Remote Similarity	NPD7902	Approved
0.6667	Remote Similarity	NPD7319	Approved
0.6667	Remote Similarity	NPD6412	Phase 2
0.6635	Remote Similarity	NPD6399	Phase 3
0.6598	Remote Similarity	NPD7525	Registered
0.6581	Remote Similarity	NPD7115	Discovery
0.6569	Remote Similarity	NPD6903	Approved
0.6538	Remote Similarity	NPD7637	Suspended
0.6538	Remote Similarity	NPD5693	Phase 1
0.6509	Remote Similarity	NPD5695	Phase 3
0.6505	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.65	Remote Similarity	NPD3666	Approved
0.65	Remote Similarity	NPD3665	Phase 1
0.65	Remote Similarity	NPD3133	Approved
0.6495	Remote Similarity	NPD7645	Phase 2
0.6481	Remote Similarity	NPD5696	Approved
0.6429	Remote Similarity	NPD6675	Approved
0.6429	Remote Similarity	NPD6402	Approved
0.6429	Remote Similarity	NPD5739	Approved
0.6429	Remote Similarity	NPD7128	Approved
0.6421	Remote Similarity	NPD6942	Approved
0.6421	Remote Similarity	NPD7339	Approved
0.6415	Remote Similarity	NPD7900	Approved
0.6415	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6404	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.64	Remote Similarity	NPD6695	Phase 3
0.6379	Remote Similarity	NPD6882	Approved
0.6373	Remote Similarity	NPD3618	Phase 1
0.6373	Remote Similarity	NPD4519	Discontinued
0.6373	Remote Similarity	NPD4623	Approved
0.6354	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6346	Remote Similarity	NPD6904	Approved
0.6346	Remote Similarity	NPD5328	Approved
0.6346	Remote Similarity	NPD6080	Approved
0.6346	Remote Similarity	NPD4753	Phase 2
0.6346	Remote Similarity	NPD6673	Approved
0.6337	Remote Similarity	NPD3668	Phase 3
0.6337	Remote Similarity	NPD4786	Approved
0.6337	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6327	Remote Similarity	NPD4195	Approved
0.6325	Remote Similarity	NPD8133	Approved
0.6316	Remote Similarity	NPD6881	Approved
0.6316	Remote Similarity	NPD7320	Approved
0.6316	Remote Similarity	NPD6899	Approved
0.63	Remote Similarity	NPD3667	Approved
0.6293	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6286	Remote Similarity	NPD5785	Approved
0.6275	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6275	Remote Similarity	NPD1694	Approved
0.6263	Remote Similarity	NPD4695	Discontinued
0.6261	Remote Similarity	NPD6372	Approved
0.6261	Remote Similarity	NPD6373	Approved
0.6239	Remote Similarity	NPD6053	Discontinued
0.6238	Remote Similarity	NPD4788	Approved
0.6228	Remote Similarity	NPD5701	Approved
0.6228	Remote Similarity	NPD5697	Approved
0.6226	Remote Similarity	NPD8035	Phase 2
0.6226	Remote Similarity	NPD6079	Approved
0.6226	Remote Similarity	NPD8034	Phase 2
0.6216	Remote Similarity	NPD5344	Discontinued
0.6207	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6207	Remote Similarity	NPD6883	Approved
0.6207	Remote Similarity	NPD7290	Approved
0.6207	Remote Similarity	NPD7102	Approved
0.6204	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6182	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6174	Remote Similarity	NPD6011	Approved
0.6162	Remote Similarity	NPD6929	Approved
0.6154	Remote Similarity	NPD6650	Approved
0.6154	Remote Similarity	NPD6847	Approved
0.6154	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD8130	Phase 1
0.6154	Remote Similarity	NPD6649	Approved
0.6154	Remote Similarity	NPD7524	Approved
0.6154	Remote Similarity	NPD6869	Approved
0.6154	Remote Similarity	NPD6617	Approved
0.6154	Remote Similarity	NPD7750	Discontinued
0.6146	Remote Similarity	NPD6926	Approved
0.6146	Remote Similarity	NPD6924	Approved
0.6139	Remote Similarity	NPD4221	Approved
0.6139	Remote Similarity	NPD4223	Phase 3
0.6129	Remote Similarity	NPD8328	Phase 3
0.6126	Remote Similarity	NPD6404	Discontinued
0.6121	Remote Similarity	NPD6012	Approved
0.6121	Remote Similarity	NPD6014	Approved
0.6121	Remote Similarity	NPD6013	Approved
0.6117	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6117	Remote Similarity	NPD5329	Approved
0.6105	Remote Similarity	NPD4243	Approved
0.6102	Remote Similarity	NPD8297	Approved
0.61	Remote Similarity	NPD6930	Phase 2
0.61	Remote Similarity	NPD6931	Approved
0.6095	Remote Similarity	NPD5208	Approved
0.6082	Remote Similarity	NPD8039	Approved
0.6078	Remote Similarity	NPD7154	Phase 3
0.6075	Remote Similarity	NPD5284	Approved
0.6075	Remote Similarity	NPD6411	Approved
0.6075	Remote Similarity	NPD5281	Approved
0.6075	Remote Similarity	NPD6050	Approved
0.6063	Remote Similarity	NPD7736	Approved
0.6061	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6061	Remote Similarity	NPD3617	Approved
0.6061	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6058	Remote Similarity	NPD6098	Approved
0.6058	Remote Similarity	NPD5279	Phase 3
0.6055	Remote Similarity	NPD5210	Approved
0.6055	Remote Similarity	NPD4629	Approved
0.6044	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.602	Remote Similarity	NPD6933	Approved
0.6019	Remote Similarity	NPD4202	Approved
0.6019	Remote Similarity	NPD5779	Approved
0.6019	Remote Similarity	NPD5778	Approved
0.6019	Remote Similarity	NPD4197	Approved
0.6018	Remote Similarity	NPD5211	Phase 2
0.6014	Remote Similarity	NPD7625	Phase 1
0.6	Remote Similarity	NPD6067	Discontinued
0.6	Remote Similarity	NPD5222	Approved
0.6	Remote Similarity	NPD3573	Approved
0.6	Remote Similarity	NPD4697	Phase 3
0.6	Remote Similarity	NPD7614	Phase 1
0.6	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6	Remote Similarity	NPD5221	Approved
0.5984	Remote Similarity	NPD8293	Discontinued
0.5983	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.5982	Remote Similarity	NPD6648	Approved
0.5981	Remote Similarity	NPD46	Approved
0.5981	Remote Similarity	NPD7838	Discovery
0.5981	Remote Similarity	NPD6698	Approved
0.5981	Remote Similarity	NPD5692	Phase 3
0.5979	Remote Similarity	NPD4784	Approved
0.5979	Remote Similarity	NPD4785	Approved
0.5978	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.5969	Remote Similarity	NPD6914	Discontinued
0.596	Remote Similarity	NPD5776	Phase 2
0.596	Remote Similarity	NPD6925	Approved
0.595	Remote Similarity	NPD6868	Approved
0.5948	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.5946	Remote Similarity	NPD4755	Approved
0.5946	Remote Similarity	NPD5173	Approved
0.5941	Remote Similarity	NPD7514	Phase 3
0.5941	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.5941	Remote Similarity	NPD7332	Phase 2
0.5926	Remote Similarity	NPD7087	Discontinued
0.5926	Remote Similarity	NPD5694	Approved
0.5922	Remote Similarity	NPD5362	Discontinued
0.592	Remote Similarity	NPD6370	Approved
0.5918	Remote Similarity	NPD8264	Approved
0.5913	Remote Similarity	NPD5141	Approved
0.5909	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.5905	Remote Similarity	NPD5205	Approved
0.5905	Remote Similarity	NPD4138	Approved
0.5905	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.5905	Remote Similarity	NPD4689	Approved
0.5905	Remote Similarity	NPD4688	Approved
0.5905	Remote Similarity	NPD4693	Phase 3
0.5905	Remote Similarity	NPD4690	Approved
0.5902	Remote Similarity	NPD6009	Approved
0.5902	Remote Similarity	NPD6317	Approved
0.59	Remote Similarity	NPD7145	Approved
0.5895	Remote Similarity	NPD6922	Approved
0.5895	Remote Similarity	NPD6923	Approved
0.5893	Remote Similarity	NPD5290	Discontinued
0.5888	Remote Similarity	NPD6101	Approved
0.5888	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.5882	Remote Similarity	NPD6902	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