NPASS Compound

Structure

CID319030 OpenBabel06191716142D 38 40 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 8.9839 -2.7436 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.5725 -6.6580 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 2.5000 -3.2321 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 5.0000 -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 5.5000 -4.9641 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 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 6.6045 -3.9696 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 7.5827 -3.7617 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 7.4135 -5.3708 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 6.5000 -4.9641 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.8614 -3.3004 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0000 -5.8301 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 7.9894 -2.8481 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.6215 -6.3490 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 8.0827 -4.6277 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 2.6217 -3.3307 0.0000 Na 0 3 0 0 0 15 0 0 0 0 0 0 1 24 1 0 0 0 0 2 24 1 0 0 0 0 5 33 1 0 0 0 0 6 34 1 0 0 0 0 7 12 1 0 0 0 0 7 13 1 0 0 0 0 8 9 1 0 0 0 0 8 17 1 0 0 0 0 9 20 1 0 0 0 0 10 15 1 0 0 0 0 10 18 1 0 0 0 0 11 14 1 0 0 0 0 11 19 1 0 0 0 0 12 24 1 0 0 0 0 13 26 1 0 0 0 0 14 25 1 0 0 0 0 15 27 1 0 0 0 0 16 17 2 0 0 0 0 16 35 1 0 0 0 0 17 18 1 0 0 0 0 18 25 1 6 0 0 0 19 24 1 0 0 0 0 19 26 1 1 0 0 0 20 25 1 1 0 0 0 20 26 1 0 0 0 0 21 22 1 0 0 0 0 21 27 1 1 0 0 0 21 28 1 0 0 0 0 22 33 1 6 0 0 0 22 36 1 0 0 0 0 23 27 1 6 0 0 0 23 34 1 0 0 0 0 23 36 1 0 0 0 0 25 3 1 6 0 0 0 26 4 1 1 0 0 0 27 29 1 1 0 0 0 30 37 1 0 0 0 0 31 37 2 0 0 0 0 32 37 2 0 0 0 0 35 37 1 0 0 0 0 M CHG 2 30 -1 38 1 M END $$$$

Physi-Chem Properties

Molecular Weight:	545.28
Volume:	534.989
LogP:	3.57
LogD:	2.435
LogS:	-4.205
# Rotatable Bonds:	7
TPSA:	134.58
# H-Bond Aceptor:	9
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.278
Synthetic Accessibility Score:	5.57
Fsp3:	0.926
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.92
MDCK Permeability:	1.1445675227150787e-05
Pgp-inhibitor:	0.987
Pgp-substrate:	0.004
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.01
30% Bioavailability (F30%):	0.744

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.091
Plasma Protein Binding (PPB):	96.93451690673828%
Volume Distribution (VD):	2.088
Pgp-substrate:	2.078587532043457%

ADMET: Metabolism

CYP1A2-inhibitor:	0.002
CYP1A2-substrate:	0.958
CYP2C19-inhibitor:	0.008
CYP2C19-substrate:	0.723
CYP2C9-inhibitor:	0.082
CYP2C9-substrate:	0.03
CYP2D6-inhibitor:	0.012
CYP2D6-substrate:	0.259
CYP3A4-inhibitor:	0.157
CYP3A4-substrate:	0.177

ADMET: Excretion

Clearance (CL):	2.327
Half-life (T1/2):	0.078

ADMET: Toxicity

hERG Blockers:	0.013
Human Hepatotoxicity (H-HT):	0.915
Drug-inuced Liver Injury (DILI):	0.026
AMES Toxicity:	0.135
Rat Oral Acute Toxicity:	0.51
Maximum Recommended Daily Dose:	0.949
Skin Sensitization:	0.403
Carcinogencity:	0.96
Eye Corrosion:	0.003
Eye Irritation:	0.013
Respiratory Toxicity:	0.972

Download Data

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

Natural Product: NPC319030

Natural Product ID:	NPC319030
*Common Name:**	Sodium(E)-((1R,4As,4Bs,8As,10As)-1-(2-((2S,3S,4R,5R)-3,4-Dihydroxy-2,5-Dimethoxytetrahydrofuran-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,3S,4R,5R)-3,4-dihydroxy-2,5-dimethoxyoxolan-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:	GFJVVNHKRRGZOW-PNSHEXGWSA-M
Standard InCHI:	InChI=1S/C27H46O9S.Na/c1-24(2)12-7-13-26(4)19(24)11-14-25(3)18(17(8-9-20(25)26)16-35-37(30,31)32)10-15-27(29)21(28)22(33-5)36-23(27)34-6;/h16,18-23,28-29H,7-15H2,1-6H3,(H,30,31,32);/q;+1/p-1/b17-16+;/t18-,19-,20-,21-,22+,23-,25+,26-,27-;/m0./s1
SMILES:	CC1(CCCC2(C1CCC3(C2CCC(=COS(=O)(=O)[O-])C3CCC4(C(C(OC4OC)OC)O)O)C)C)C.[Na+]
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1818094
PubChem CID:	53484121
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	=	15000.0	nM	PMID[489933]
NPT1821	Individual Protein	Sortase	Staphylococcus aureus	IC50	>	200000.0	nM	PMID[489933]
NPT1087	Individual Protein	Isocitrate lyase	Candida albicans	IC50	=	75000.0	nM	PMID[489933]
NPT2890	Protein Complex	Sodium/potassium-transporting ATPase	Homo sapiens	IC50	=	6000.0	nM	PMID[489933]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>	100.0	ug.mL-1	PMID[489933]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	>	100.0	ug.mL-1	PMID[489933]
NPT729	Organism	Micrococcus luteus	Micrococcus luteus	MIC	>	100.0	ug.mL-1	PMID[489933]
NPT566	Organism	Salmonella typhimurium	Salmonella enterica subsp. enterica serovar Typhimurium	MIC	>	100.0	ug.mL-1	PMID[489933]
NPT766	Organism	Proteus vulgaris	Proteus vulgaris	MIC	>	100.0	ug.mL-1	PMID[489933]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	100.0	ug.mL-1	PMID[489933]
NPT87	Organism	Aspergillus fumigatus	Aspergillus fumigatus	MIC	>	100.0	ug.mL-1	PMID[489933]
NPT329	Organism	Trichophyton rubrum	Trichophyton rubrum	MIC	>	100.0	ug.mL-1	PMID[489933]
NPT330	Organism	Trichophyton mentagrophytes	Trichophyton mentagrophytes	MIC	>	100.0	ug.mL-1	PMID[489933]
NPT20	Organism	Candida albicans	Candida albicans	MIC	>	100.0	ug.mL-1	PMID[489933]

☑ 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 NPC319030 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	199
0.1-0.2	2121
0.2-0.3	9250
0.3-0.4	13637
0.4-0.5	7433
0.5-0.6	5475
0.6-0.7	3904
0.7-0.8	672
0.8-0.85	5
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8333	Intermediate Similarity	NPC473058
0.8242	Intermediate Similarity	NPC159876
0.8191	Intermediate Similarity	NPC472989
0.7957	Intermediate Similarity	NPC48463
0.7921	Intermediate Similarity	NPC475634
0.7895	Intermediate Similarity	NPC275310
0.7895	Intermediate Similarity	NPC230347
0.7895	Intermediate Similarity	NPC286612
0.7879	Intermediate Similarity	NPC213190
0.7857	Intermediate Similarity	NPC4831
0.7857	Intermediate Similarity	NPC129372
0.7857	Intermediate Similarity	NPC309425
0.7857	Intermediate Similarity	NPC47566
0.7857	Intermediate Similarity	NPC88000
0.7857	Intermediate Similarity	NPC160734
0.7857	Intermediate Similarity	NPC472023
0.7843	Intermediate Similarity	NPC474573
0.7835	Intermediate Similarity	NPC5358
0.7835	Intermediate Similarity	NPC216260
0.7812	Intermediate Similarity	NPC90583
0.7778	Intermediate Similarity	NPC166279
0.7778	Intermediate Similarity	NPC319238
0.7778	Intermediate Similarity	NPC136816
0.7766	Intermediate Similarity	NPC302584
0.7755	Intermediate Similarity	NPC7341
0.7755	Intermediate Similarity	NPC473200
0.7732	Intermediate Similarity	NPC76486
0.77	Intermediate Similarity	NPC31907
0.77	Intermediate Similarity	NPC286969
0.77	Intermediate Similarity	NPC131479
0.77	Intermediate Similarity	NPC211879
0.77	Intermediate Similarity	NPC8039
0.77	Intermediate Similarity	NPC114874
0.77	Intermediate Similarity	NPC472252
0.77	Intermediate Similarity	NPC120123
0.77	Intermediate Similarity	NPC189852
0.77	Intermediate Similarity	NPC16520
0.77	Intermediate Similarity	NPC245280
0.77	Intermediate Similarity	NPC155010
0.77	Intermediate Similarity	NPC473020
0.77	Intermediate Similarity	NPC157659
0.7684	Intermediate Similarity	NPC474835
0.7684	Intermediate Similarity	NPC474792
0.7684	Intermediate Similarity	NPC67398
0.7684	Intermediate Similarity	NPC91654
0.7677	Intermediate Similarity	NPC31346
0.766	Intermediate Similarity	NPC261990
0.766	Intermediate Similarity	NPC474249
0.7653	Intermediate Similarity	NPC280825
0.7653	Intermediate Similarity	NPC157739
0.7653	Intermediate Similarity	NPC234287
0.7629	Intermediate Similarity	NPC207617
0.7624	Intermediate Similarity	NPC273879
0.7624	Intermediate Similarity	NPC165033
0.7624	Intermediate Similarity	NPC476361
0.7624	Intermediate Similarity	NPC476360
0.7624	Intermediate Similarity	NPC475521
0.7604	Intermediate Similarity	NPC72817
0.7604	Intermediate Similarity	NPC211238
0.7604	Intermediate Similarity	NPC477927
0.7604	Intermediate Similarity	NPC305160
0.76	Intermediate Similarity	NPC159036
0.76	Intermediate Similarity	NPC288694
0.76	Intermediate Similarity	NPC94919
0.76	Intermediate Similarity	NPC312553
0.7579	Intermediate Similarity	NPC120539
0.7579	Intermediate Similarity	NPC289361
0.7576	Intermediate Similarity	NPC471247
0.7576	Intermediate Similarity	NPC91497
0.7576	Intermediate Similarity	NPC324598
0.7576	Intermediate Similarity	NPC282669
0.7573	Intermediate Similarity	NPC220427
0.7573	Intermediate Similarity	NPC224414
0.7556	Intermediate Similarity	NPC477599
0.7551	Intermediate Similarity	NPC473555
0.7551	Intermediate Similarity	NPC473890
0.7551	Intermediate Similarity	NPC278939
0.7551	Intermediate Similarity	NPC243728
0.7551	Intermediate Similarity	NPC471770
0.7549	Intermediate Similarity	NPC472900
0.7549	Intermediate Similarity	NPC194842
0.7549	Intermediate Similarity	NPC472899
0.7549	Intermediate Similarity	NPC473199
0.7549	Intermediate Similarity	NPC69737
0.7549	Intermediate Similarity	NPC160816
0.7549	Intermediate Similarity	NPC208477
0.7549	Intermediate Similarity	NPC208594
0.7549	Intermediate Similarity	NPC152584
0.7549	Intermediate Similarity	NPC269627
0.7549	Intermediate Similarity	NPC127801
0.7549	Intermediate Similarity	NPC472898
0.7549	Intermediate Similarity	NPC26798
0.7547	Intermediate Similarity	NPC476671
0.7527	Intermediate Similarity	NPC477600
0.7525	Intermediate Similarity	NPC473198
0.7525	Intermediate Similarity	NPC16573
0.75	Intermediate Similarity	NPC246860
0.75	Intermediate Similarity	NPC177343
0.75	Intermediate Similarity	NPC117714
0.75	Intermediate Similarity	NPC263756
0.7476	Intermediate Similarity	NPC63368
0.7476	Intermediate Similarity	NPC54619
0.7476	Intermediate Similarity	NPC231340
0.7476	Intermediate Similarity	NPC226642
0.7476	Intermediate Similarity	NPC208650
0.7476	Intermediate Similarity	NPC181467
0.7476	Intermediate Similarity	NPC14946
0.7475	Intermediate Similarity	NPC309493
0.7475	Intermediate Similarity	NPC158088
0.7473	Intermediate Similarity	NPC324243
0.7471	Intermediate Similarity	NPC470766
0.7453	Intermediate Similarity	NPC475354
0.7453	Intermediate Similarity	NPC475312
0.7451	Intermediate Similarity	NPC470043
0.7451	Intermediate Similarity	NPC187400
0.7451	Intermediate Similarity	NPC470057
0.7451	Intermediate Similarity	NPC470062
0.7451	Intermediate Similarity	NPC470064
0.7451	Intermediate Similarity	NPC470061
0.7451	Intermediate Similarity	NPC470059
0.7451	Intermediate Similarity	NPC121566
0.7451	Intermediate Similarity	NPC470060
0.7451	Intermediate Similarity	NPC470058
0.7451	Intermediate Similarity	NPC31430
0.7451	Intermediate Similarity	NPC221562
0.7451	Intermediate Similarity	NPC470885
0.7451	Intermediate Similarity	NPC475365
0.7451	Intermediate Similarity	NPC100955
0.7451	Intermediate Similarity	NPC85593
0.7447	Intermediate Similarity	NPC473436
0.7447	Intermediate Similarity	NPC263079
0.7431	Intermediate Similarity	NPC476691
0.7431	Intermediate Similarity	NPC476692
0.7429	Intermediate Similarity	NPC106760
0.7426	Intermediate Similarity	NPC256133
0.7426	Intermediate Similarity	NPC30289
0.7426	Intermediate Similarity	NPC76497
0.7426	Intermediate Similarity	NPC213674
0.7426	Intermediate Similarity	NPC272015
0.7423	Intermediate Similarity	NPC473503
0.7419	Intermediate Similarity	NPC173917
0.7404	Intermediate Similarity	NPC159005
0.7404	Intermediate Similarity	NPC38376
0.7404	Intermediate Similarity	NPC80210
0.7404	Intermediate Similarity	NPC49032
0.7404	Intermediate Similarity	NPC180183
0.7404	Intermediate Similarity	NPC51172
0.7404	Intermediate Similarity	NPC6931
0.7404	Intermediate Similarity	NPC38217
0.7404	Intermediate Similarity	NPC125324
0.7404	Intermediate Similarity	NPC472988
0.7404	Intermediate Similarity	NPC246124
0.74	Intermediate Similarity	NPC473790
0.74	Intermediate Similarity	NPC469942
0.74	Intermediate Similarity	NPC317019
0.7396	Intermediate Similarity	NPC473637
0.7396	Intermediate Similarity	NPC476668
0.7379	Intermediate Similarity	NPC165405
0.7379	Intermediate Similarity	NPC474569
0.7379	Intermediate Similarity	NPC181845
0.7379	Intermediate Similarity	NPC95243
0.7379	Intermediate Similarity	NPC63023
0.7379	Intermediate Similarity	NPC309448
0.7374	Intermediate Similarity	NPC125551
0.7374	Intermediate Similarity	NPC309503
0.7374	Intermediate Similarity	NPC91197
0.7374	Intermediate Similarity	NPC96597
0.7374	Intermediate Similarity	NPC239547
0.7374	Intermediate Similarity	NPC155319
0.7374	Intermediate Similarity	NPC240372
0.7368	Intermediate Similarity	NPC82955
0.7358	Intermediate Similarity	NPC272242
0.7353	Intermediate Similarity	NPC473123
0.7353	Intermediate Similarity	NPC473124
0.7353	Intermediate Similarity	NPC162354
0.7353	Intermediate Similarity	NPC473129
0.7353	Intermediate Similarity	NPC123796
0.7353	Intermediate Similarity	NPC99627
0.7347	Intermediate Similarity	NPC469710
0.734	Intermediate Similarity	NPC43912
0.734	Intermediate Similarity	NPC140446
0.7333	Intermediate Similarity	NPC151134
0.7333	Intermediate Similarity	NPC40440
0.7333	Intermediate Similarity	NPC285253
0.7333	Intermediate Similarity	NPC296761
0.7333	Intermediate Similarity	NPC154085
0.7333	Intermediate Similarity	NPC472901
0.7333	Intermediate Similarity	NPC51925
0.7333	Intermediate Similarity	NPC195116
0.7333	Intermediate Similarity	NPC43976
0.7333	Intermediate Similarity	NPC221110
0.7333	Intermediate Similarity	NPC180459
0.7333	Intermediate Similarity	NPC8431
0.7333	Intermediate Similarity	NPC125361
0.7333	Intermediate Similarity	NPC42482
0.7327	Intermediate Similarity	NPC121072
0.7327	Intermediate Similarity	NPC285231
0.7327	Intermediate Similarity	NPC21064
0.7327	Intermediate Similarity	NPC21568
0.7327	Intermediate Similarity	NPC470168

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 NPC319030 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	165
0.1-0.2	2413
0.2-0.3	4374
0.3-0.4	1461
0.4-0.5	369
0.5-0.6	287
0.6-0.7	78
0.7-0.8	3
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
0.7064	Intermediate Similarity	NPD8133	Approved
0.6981	Remote Similarity	NPD6412	Phase 2
0.697	Remote Similarity	NPD8171	Discontinued
0.6957	Remote Similarity	NPD7525	Registered
0.6916	Remote Similarity	NPD6686	Approved
0.6814	Remote Similarity	NPD7328	Approved
0.6814	Remote Similarity	NPD7327	Approved
0.6754	Remote Similarity	NPD7516	Approved
0.6696	Remote Similarity	NPD8377	Approved
0.6696	Remote Similarity	NPD8294	Approved
0.6667	Remote Similarity	NPD7645	Phase 2
0.6638	Remote Similarity	NPD8378	Approved
0.6638	Remote Similarity	NPD8033	Approved
0.6638	Remote Similarity	NPD8296	Approved
0.6638	Remote Similarity	NPD7503	Approved
0.6638	Remote Similarity	NPD8335	Approved
0.6638	Remote Similarity	NPD8380	Approved
0.6638	Remote Similarity	NPD8379	Approved
0.6633	Remote Similarity	NPD7524	Approved
0.6627	Remote Similarity	NPD1145	Discontinued
0.6591	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6545	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD6933	Approved
0.6495	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6421	Remote Similarity	NPD6928	Phase 2
0.6417	Remote Similarity	NPD7507	Approved
0.6413	Remote Similarity	NPD6942	Approved
0.6413	Remote Similarity	NPD7339	Approved
0.6392	Remote Similarity	NPD6695	Phase 3
0.6392	Remote Similarity	NPD4788	Approved
0.6373	Remote Similarity	NPD8034	Phase 2
0.6373	Remote Similarity	NPD8035	Phase 2
0.6344	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.633	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6304	Remote Similarity	NPD1811	Approved
0.6304	Remote Similarity	NPD6926	Approved
0.6304	Remote Similarity	NPD6924	Approved
0.6304	Remote Similarity	NPD1810	Approved
0.6303	Remote Similarity	NPD6370	Approved
0.6293	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6263	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.626	Remote Similarity	NPD7319	Approved
0.625	Remote Similarity	NPD8328	Phase 3
0.6228	Remote Similarity	NPD6882	Approved
0.6179	Remote Similarity	NPD7736	Approved
0.6168	Remote Similarity	NPD4225	Approved
0.6154	Remote Similarity	NPD6399	Phase 3
0.6139	Remote Similarity	NPD7750	Discontinued
0.6134	Remote Similarity	NPD6059	Approved
0.6134	Remote Similarity	NPD6054	Approved
0.6116	Remote Similarity	NPD6067	Discontinued
0.6098	Remote Similarity	NPD8293	Discontinued
0.6087	Remote Similarity	NPD8297	Approved
0.6087	Remote Similarity	NPD4243	Approved
0.6082	Remote Similarity	NPD7509	Discontinued
0.6082	Remote Similarity	NPD6931	Approved
0.6082	Remote Similarity	NPD6930	Phase 2
0.6075	Remote Similarity	NPD6084	Phase 2
0.6075	Remote Similarity	NPD6083	Phase 2
0.6019	Remote Similarity	NPD7638	Approved
0.6	Remote Similarity	NPD3668	Phase 3
0.6	Remote Similarity	NPD4786	Approved
0.5984	Remote Similarity	NPD8449	Approved
0.5982	Remote Similarity	NPD6675	Approved
0.5982	Remote Similarity	NPD5739	Approved
0.5982	Remote Similarity	NPD7128	Approved
0.5982	Remote Similarity	NPD6402	Approved
0.5979	Remote Similarity	NPD6929	Approved
0.5978	Remote Similarity	NPD2686	Approved
0.5978	Remote Similarity	NPD2254	Approved
0.5978	Remote Similarity	NPD2687	Approved
0.5965	Remote Similarity	NPD6373	Approved
0.5965	Remote Similarity	NPD6372	Approved
0.5963	Remote Similarity	NPD7640	Approved
0.5963	Remote Similarity	NPD7639	Approved
0.596	Remote Similarity	NPD3667	Approved
0.5957	Remote Similarity	NPD4785	Approved
0.5957	Remote Similarity	NPD4784	Approved
0.595	Remote Similarity	NPD6015	Approved
0.595	Remote Similarity	NPD6016	Approved
0.5943	Remote Similarity	NPD7748	Approved
0.5938	Remote Similarity	NPD6932	Approved
0.5938	Remote Similarity	NPD8450	Suspended
0.5935	Remote Similarity	NPD7492	Approved
0.5926	Remote Similarity	NPD7902	Approved
0.5909	Remote Similarity	NPD4159	Approved
0.5905	Remote Similarity	NPD7087	Discontinued
0.5905	Remote Similarity	NPD7515	Phase 2
0.5902	Remote Similarity	NPD5988	Approved
0.59	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.59	Remote Similarity	NPD3669	Approved
0.5887	Remote Similarity	NPD6616	Approved
0.5877	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.5877	Remote Similarity	NPD6899	Approved
0.5877	Remote Similarity	NPD7320	Approved
0.5877	Remote Similarity	NPD6881	Approved
0.587	Remote Similarity	NPD6922	Approved
0.587	Remote Similarity	NPD6923	Approved
0.5865	Remote Similarity	NPD4753	Phase 2
0.5865	Remote Similarity	NPD6051	Approved
0.5862	Remote Similarity	NPD6650	Approved
0.5862	Remote Similarity	NPD6649	Approved
0.5842	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.5842	Remote Similarity	NPD3666	Approved
0.5842	Remote Similarity	NPD3133	Approved
0.5842	Remote Similarity	NPD3665	Phase 1
0.584	Remote Similarity	NPD7078	Approved
0.5826	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.5825	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.5816	Remote Similarity	NPD6683	Phase 2
0.5806	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.5806	Remote Similarity	NPD7144	Approved
0.5806	Remote Similarity	NPD4787	Phase 1
0.5806	Remote Similarity	NPD7143	Approved
0.5789	Remote Similarity	NPD5701	Approved
0.5789	Remote Similarity	NPD5697	Approved
0.5784	Remote Similarity	NPD6893	Approved
0.578	Remote Similarity	NPD4755	Approved
0.5776	Remote Similarity	NPD7102	Approved
0.5776	Remote Similarity	NPD7290	Approved
0.5776	Remote Similarity	NPD6883	Approved
0.5773	Remote Similarity	NPD5776	Phase 2
0.5773	Remote Similarity	NPD6116	Phase 1
0.5773	Remote Similarity	NPD6925	Approved
0.5769	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.5758	Remote Similarity	NPD7332	Phase 2
0.5758	Remote Similarity	NPD7514	Phase 3
0.5758	Remote Similarity	NPD4748	Discontinued
0.575	Remote Similarity	NPD6009	Approved
0.575	Remote Similarity	NPD7115	Discovery
0.5745	Remote Similarity	NPD7151	Approved
0.5745	Remote Similarity	NPD7150	Approved
0.5745	Remote Similarity	NPD7152	Approved
0.5741	Remote Similarity	NPD5695	Phase 3
0.5738	Remote Similarity	NPD6319	Approved
0.5729	Remote Similarity	NPD4190	Phase 3
0.5729	Remote Similarity	NPD5275	Approved
0.5728	Remote Similarity	NPD7334	Approved
0.5728	Remote Similarity	NPD6684	Approved
0.5728	Remote Similarity	NPD5330	Approved
0.5728	Remote Similarity	NPD6409	Approved
0.5728	Remote Similarity	NPD7146	Approved
0.5728	Remote Similarity	NPD3618	Phase 1
0.5728	Remote Similarity	NPD7521	Approved
0.5727	Remote Similarity	NPD5696	Approved
0.5726	Remote Similarity	NPD6617	Approved
0.5726	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5726	Remote Similarity	NPD8130	Phase 1
0.5726	Remote Similarity	NPD6869	Approved
0.5726	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.5726	Remote Similarity	NPD6847	Approved
0.5714	Remote Similarity	NPD5328	Approved
0.5714	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD7145	Approved
0.5701	Remote Similarity	NPD4202	Approved
0.57	Remote Similarity	NPD6898	Phase 1
0.5691	Remote Similarity	NPD8516	Approved
0.5691	Remote Similarity	NPD8517	Approved
0.5691	Remote Similarity	NPD8515	Approved
0.5691	Remote Similarity	NPD8513	Phase 3
0.569	Remote Similarity	NPD6014	Approved
0.569	Remote Similarity	NPD6013	Approved
0.569	Remote Similarity	NPD6012	Approved
0.5676	Remote Similarity	NPD5285	Approved
0.5676	Remote Similarity	NPD4700	Approved
0.5676	Remote Similarity	NPD5286	Approved
0.5676	Remote Similarity	NPD4696	Approved
0.567	Remote Similarity	NPD6117	Approved
0.5669	Remote Similarity	NPD6033	Approved
0.5667	Remote Similarity	NPD371	Approved
0.566	Remote Similarity	NPD3168	Discontinued
0.5657	Remote Similarity	NPD4195	Approved
0.5648	Remote Similarity	NPD7900	Approved
0.5648	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.5641	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.5638	Remote Similarity	NPD4244	Approved
0.5638	Remote Similarity	NPD4245	Approved
0.563	Remote Similarity	NPD4632	Approved
0.5625	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.5619	Remote Similarity	NPD6903	Approved
0.5619	Remote Similarity	NPD6672	Approved
0.5619	Remote Similarity	NPD5737	Approved
0.5607	Remote Similarity	NPD6079	Approved
0.5607	Remote Similarity	NPD7637	Suspended
0.5607	Remote Similarity	NPD6411	Approved
0.5603	Remote Similarity	NPD8174	Phase 2
0.5603	Remote Similarity	NPD6011	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