NPASS Compound

Structure

NPC63249 OpenBabel07101718222D 32 36 0 0 1 0 0 0 0 0999 V2000 3.2709 -5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7350 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2350 -1.6340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1369 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5388 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8690 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4049 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2709 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8690 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2709 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7350 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0029 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0029 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4049 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1369 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2709 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5388 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8690 -2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.2709 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.1369 -2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.5388 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.5878 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5878 -0.8090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 6.7350 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1369 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.4049 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.0029 -2.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.4049 -4.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2788 1.7601 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2788 -1.7601 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.1369 -4.0000 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 16 1 0 0 0 0 2 24 1 0 0 0 0 3 24 1 0 0 0 0 6 11 1 0 0 0 0 6 12 1 0 0 0 0 7 8 1 0 0 0 0 7 17 2 0 0 0 0 8 19 1 0 0 0 0 9 13 1 0 0 0 0 9 18 1 0 0 0 0 10 14 1 0 0 0 0 10 20 1 0 0 0 0 11 24 1 0 0 0 0 12 27 1 0 0 0 0 13 25 1 0 0 0 0 14 26 1 0 0 0 0 15 31 1 0 0 0 0 16 28 2 0 0 0 0 16 31 1 0 0 0 0 17 21 1 0 0 0 0 17 22 1 0 0 0 0 18 24 1 0 0 0 0 18 27 1 1 0 0 0 19 25 1 1 0 0 0 19 26 1 0 0 0 0 20 25 1 1 0 0 0 20 27 1 0 0 0 0 21 23 1 0 0 0 0 21 26 1 1 0 0 0 22 29 2 0 0 0 0 22 32 1 0 0 0 0 23 30 1 6 0 0 0 23 32 1 0 0 0 0 25 4 1 1 0 0 0 26 5 1 1 0 0 0 27 15 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	444.29
Volume:	468.808
LogP:	4.871
LogD:	4.071
LogS:	-5.068
# Rotatable Bonds:	3
TPSA:	72.83
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.486
Synthetic Accessibility Score:	5.142
Fsp3:	0.852
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:	-4.758
MDCK Permeability:	1.803754457796458e-05
Pgp-inhibitor:	0.981
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.972
30% Bioavailability (F30%):	0.97

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.553
Plasma Protein Binding (PPB):	70.31543731689453%
Volume Distribution (VD):	1.333
Pgp-substrate:	28.136762619018555%

ADMET: Metabolism

CYP1A2-inhibitor:	0.056
CYP1A2-substrate:	0.153
CYP2C19-inhibitor:	0.054
CYP2C19-substrate:	0.371
CYP2C9-inhibitor:	0.137
CYP2C9-substrate:	0.043
CYP2D6-inhibitor:	0.017
CYP2D6-substrate:	0.093
CYP3A4-inhibitor:	0.831
CYP3A4-substrate:	0.184

ADMET: Excretion

Clearance (CL):	4.76
Half-life (T1/2):	0.075

ADMET: Toxicity

hERG Blockers:	0.036
Human Hepatotoxicity (H-HT):	0.077
Drug-inuced Liver Injury (DILI):	0.158
AMES Toxicity:	0.043
Rat Oral Acute Toxicity:	0.328
Maximum Recommended Daily Dose:	0.878
Skin Sensitization:	0.631
Carcinogencity:	0.257
Eye Corrosion:	0.142
Eye Irritation:	0.112
Respiratory Toxicity:	0.961

Download Data

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

Natural Product: NPC63249

Natural Product ID:	NPC63249
*Common Name:**	12-Deacetoxy-23-Acetoxy-19-O-Acetylscalarin
IUPAC Name:	[(1R,5aS,5bS,7aS,11aR,11bS,13aS,13bR)-1-hydroxy-5b,8,8,13a-tetramethyl-3-oxo-5,5a,6,7,7a,9,10,11,11b,12,13,13b-dodecahydro-1H-phenanthro[2,1-e][2]benzofuran-11a-yl]methyl acetate
Synonyms:
Standard InCHIKey:	NQUDADRZXBXFOV-JMJANOEMSA-N
Standard InCHI:	InChI=1S/C27H40O5/c1-16(28)31-15-27-12-6-11-24(2,3)18(27)9-13-25(4)19-8-7-17-21(23(30)32-22(17)29)26(19,5)14-10-20(25)27/h7,18-21,23,30H,6,8-15H2,1-5H3/t18-,19-,20-,21+,23+,25-,26-,27+/m0/s1
SMILES:	CC(=O)OC[C@]12CCCC(C)(C)[C@@H]1CC[C@@]1(C)[C@@H]3CC=C4[C@H]([C@H](O)OC4=O)[C@@]3(C)CC[C@H]21
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL576346
PubChem CID:	11166698
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001552] Sesterterpenoids [CHEMONTID:0002883] Scalarane 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
NPO33102	psammocinia sp.	Species	Irciniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[15270579]
NPO32965	smenospongia sp.	Species	Thorectidae	Eukaryota	n.a.	n.a.	n.a.	PMID[15497955]
NPO32965	smenospongia sp.	Species	Thorectidae	Eukaryota	n.a.	n.a.	n.a.	PMID[16252912]
NPO32965	smenospongia sp.	Species	Thorectidae	Eukaryota	n.a.	n.a.	n.a.	PMID[18973387]
NPO33102	psammocinia sp.	Species	Irciniidae	Eukaryota	n.a.	Korean	n.a.	PMID[23489626]
NPO33102	psammocinia sp.	Species	Irciniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[28621941]

☑ 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	6
MIC	6
Others	2

Activity Type	# Activity
Cell Line	6
Individual Protein	1
NON-MOLECULAR	1
Organism	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT111	Cell Line	K562	Homo sapiens	LC50	=	4.9	ug.mL-1	PMID[571181]
NPT111	Cell Line	K562	Homo sapiens	LC50	=	7.2	ug.mL-1	PMID[571182]
NPT4391	Individual Protein	Isocitrate lyase	Magnaporthe oryzae (strain 70-15 / FGSC 8958) (Rice blast fungus)(Pyricularia oryzae)	IC50	=	67.2	ug.mL-1	PMID[571182]
NPT3885	Cell Line	CV-1	Chlorocebus aethiops	IC50	=	2100.0	nM	PMID[571183]
NPT461	Cell Line	PANC-1	Homo sapiens	IC50	=	1300.0	nM	PMID[571183]
NPT369	Cell Line	ACHN	Homo sapiens	IC50	=	1300.0	nM	PMID[571183]
NPT376	Cell Line	A498	Homo sapiens	IC50	=	1300.0	nM	PMID[571183]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>	100.0	ug.mL-1	PMID[571182]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	>	100.0	ug.mL-1	PMID[571182]
NPT729	Organism	Micrococcus luteus	Micrococcus luteus	MIC	>	100.0	ug.mL-1	PMID[571182]
NPT766	Organism	Proteus vulgaris	Proteus vulgaris	MIC	>	100.0	ug.mL-1	PMID[571182]
NPT566	Organism	Salmonella typhimurium	Salmonella enterica subsp. enterica serovar Typhimurium	MIC	>	100.0	ug.mL-1	PMID[571182]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	100.0	ug.mL-1	PMID[571182]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	1200.0	nM	PMID[571183]

☑ 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 NPC63249 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	197
0.1-0.2	1194
0.2-0.3	4226
0.3-0.4	10722
0.4-0.5	10925
0.5-0.6	6254
0.6-0.7	6053
0.7-0.8	2997
0.8-0.85	110
0.85-0.9	12
0.9-0.95	5
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9894	High Similarity	NPC134077
0.9468	High Similarity	NPC257726
0.9468	High Similarity	NPC204054
0.9247	High Similarity	NPC166346
0.9062	High Similarity	NPC76266
0.9029	High Similarity	NPC194951
0.9029	High Similarity	NPC12046
0.8942	High Similarity	NPC157441
0.8936	High Similarity	NPC65513
0.8878	High Similarity	NPC477720
0.8737	High Similarity	NPC165904
0.8737	High Similarity	NPC179517
0.8737	High Similarity	NPC477783
0.8723	High Similarity	NPC168131
0.8646	High Similarity	NPC470656
0.8641	High Similarity	NPC275539
0.8641	High Similarity	NPC189075
0.8632	High Similarity	NPC477782
0.8586	High Similarity	NPC473154
0.8558	High Similarity	NPC112457
0.8544	High Similarity	NPC110496
0.8529	High Similarity	NPC222161
0.8526	High Similarity	NPC251528
0.8526	High Similarity	NPC174342
0.8495	Intermediate Similarity	NPC217394
0.8485	Intermediate Similarity	NPC175351
0.8485	Intermediate Similarity	NPC132753
0.8485	Intermediate Similarity	NPC151681
0.8485	Intermediate Similarity	NPC121402
0.8485	Intermediate Similarity	NPC224356
0.8462	Intermediate Similarity	NPC325054
0.8454	Intermediate Similarity	NPC151722
0.8454	Intermediate Similarity	NPC267266
0.8454	Intermediate Similarity	NPC277721
0.8438	Intermediate Similarity	NPC101651
0.8438	Intermediate Similarity	NPC159748
0.8431	Intermediate Similarity	NPC471208
0.8416	Intermediate Similarity	NPC471075
0.8404	Intermediate Similarity	NPC173917
0.8384	Intermediate Similarity	NPC319692
0.8384	Intermediate Similarity	NPC472363
0.8384	Intermediate Similarity	NPC154526
0.8384	Intermediate Similarity	NPC472362
0.8384	Intermediate Similarity	NPC112654
0.8384	Intermediate Similarity	NPC325960
0.8367	Intermediate Similarity	NPC476415
0.8333	Intermediate Similarity	NPC477973
0.8333	Intermediate Similarity	NPC5509
0.8317	Intermediate Similarity	NPC228251
0.8317	Intermediate Similarity	NPC477971
0.8317	Intermediate Similarity	NPC477972
0.8317	Intermediate Similarity	NPC20113
0.8317	Intermediate Similarity	NPC477968
0.8317	Intermediate Similarity	NPC161527
0.8317	Intermediate Similarity	NPC219285
0.83	Intermediate Similarity	NPC475709
0.8298	Intermediate Similarity	NPC106416
0.8298	Intermediate Similarity	NPC65661
0.8298	Intermediate Similarity	NPC86316
0.8286	Intermediate Similarity	NPC90946
0.8286	Intermediate Similarity	NPC300614
0.8283	Intermediate Similarity	NPC183012
0.828	Intermediate Similarity	NPC22611
0.8273	Intermediate Similarity	NPC475913
0.8265	Intermediate Similarity	NPC472303
0.8252	Intermediate Similarity	NPC254202
0.8247	Intermediate Similarity	NPC232426
0.8247	Intermediate Similarity	NPC281942
0.8218	Intermediate Similarity	NPC478056
0.8211	Intermediate Similarity	NPC474062
0.8211	Intermediate Similarity	NPC118266
0.8208	Intermediate Similarity	NPC31522
0.8208	Intermediate Similarity	NPC476759
0.8198	Intermediate Similarity	NPC475834
0.8198	Intermediate Similarity	NPC474179
0.8182	Intermediate Similarity	NPC469697
0.8182	Intermediate Similarity	NPC324078
0.8182	Intermediate Similarity	NPC104925
0.8182	Intermediate Similarity	NPC298973
0.8163	Intermediate Similarity	NPC233345
0.8163	Intermediate Similarity	NPC289479
0.8163	Intermediate Similarity	NPC141831
0.8163	Intermediate Similarity	NPC186363
0.8155	Intermediate Similarity	NPC31058
0.8155	Intermediate Similarity	NPC469606
0.8155	Intermediate Similarity	NPC165250
0.8155	Intermediate Similarity	NPC273005
0.8144	Intermediate Similarity	NPC293044
0.8137	Intermediate Similarity	NPC476767
0.8131	Intermediate Similarity	NPC235014
0.8119	Intermediate Similarity	NPC477718
0.8119	Intermediate Similarity	NPC170131
0.8119	Intermediate Similarity	NPC474343
0.8119	Intermediate Similarity	NPC477719
0.8113	Intermediate Similarity	NPC476765
0.8113	Intermediate Similarity	NPC392
0.8113	Intermediate Similarity	NPC469844
0.8113	Intermediate Similarity	NPC219900
0.8113	Intermediate Similarity	NPC177524
0.8105	Intermediate Similarity	NPC42586
0.8105	Intermediate Similarity	NPC30984
0.8105	Intermediate Similarity	NPC473251
0.8095	Intermediate Similarity	NPC127790
0.8085	Intermediate Similarity	NPC469
0.8081	Intermediate Similarity	NPC169343
0.8081	Intermediate Similarity	NPC476416
0.8077	Intermediate Similarity	NPC476889
0.8065	Intermediate Similarity	NPC14203
0.8065	Intermediate Similarity	NPC40228
0.8065	Intermediate Similarity	NPC229584
0.8061	Intermediate Similarity	NPC51486
0.8061	Intermediate Similarity	NPC253186
0.8061	Intermediate Similarity	NPC198818
0.8061	Intermediate Similarity	NPC220454
0.8061	Intermediate Similarity	NPC212679
0.8061	Intermediate Similarity	NPC469595
0.8058	Intermediate Similarity	NPC235142
0.8041	Intermediate Similarity	NPC226863
0.8039	Intermediate Similarity	NPC124703
0.8039	Intermediate Similarity	NPC234617
0.8039	Intermediate Similarity	NPC98868
0.8039	Intermediate Similarity	NPC194196
0.8039	Intermediate Similarity	NPC23364
0.802	Intermediate Similarity	NPC470801
0.802	Intermediate Similarity	NPC162346
0.802	Intermediate Similarity	NPC235053
0.8019	Intermediate Similarity	NPC91034
0.8019	Intermediate Similarity	NPC301666
0.8018	Intermediate Similarity	NPC473968
0.8	Intermediate Similarity	NPC71626
0.8	Intermediate Similarity	NPC474554
0.8	Intermediate Similarity	NPC91010
0.8	Intermediate Similarity	NPC477129
0.8	Intermediate Similarity	NPC477130
0.7981	Intermediate Similarity	NPC476081
0.7981	Intermediate Similarity	NPC476769
0.7981	Intermediate Similarity	NPC40918
0.7981	Intermediate Similarity	NPC476890
0.7981	Intermediate Similarity	NPC136289
0.798	Intermediate Similarity	NPC477122
0.798	Intermediate Similarity	NPC72845
0.7979	Intermediate Similarity	NPC186276
0.7979	Intermediate Similarity	NPC200513
0.7963	Intermediate Similarity	NPC476766
0.7961	Intermediate Similarity	NPC201406
0.7961	Intermediate Similarity	NPC476299
0.7961	Intermediate Similarity	NPC474012
0.7961	Intermediate Similarity	NPC477721
0.7961	Intermediate Similarity	NPC477716
0.7961	Intermediate Similarity	NPC47024
0.7959	Intermediate Similarity	NPC470734
0.7959	Intermediate Similarity	NPC50488
0.7959	Intermediate Similarity	NPC474396
0.7957	Intermediate Similarity	NPC104545
0.7957	Intermediate Similarity	NPC195424
0.7944	Intermediate Similarity	NPC473483
0.7941	Intermediate Similarity	NPC253826
0.7941	Intermediate Similarity	NPC476253
0.7938	Intermediate Similarity	NPC477228
0.7938	Intermediate Similarity	NPC312561
0.7928	Intermediate Similarity	NPC268954
0.7928	Intermediate Similarity	NPC44170
0.7925	Intermediate Similarity	NPC252296
0.7925	Intermediate Similarity	NPC469607
0.7921	Intermediate Similarity	NPC293052
0.7921	Intermediate Similarity	NPC477969
0.7921	Intermediate Similarity	NPC209355
0.7921	Intermediate Similarity	NPC135224
0.7921	Intermediate Similarity	NPC473369
0.7917	Intermediate Similarity	NPC189311
0.7917	Intermediate Similarity	NPC329738
0.7909	Intermediate Similarity	NPC25909
0.7905	Intermediate Similarity	NPC95899
0.7905	Intermediate Similarity	NPC471364
0.7905	Intermediate Similarity	NPC478057
0.7905	Intermediate Similarity	NPC132395
0.7905	Intermediate Similarity	NPC476237
0.7905	Intermediate Similarity	NPC471365
0.7905	Intermediate Similarity	NPC112009
0.79	Intermediate Similarity	NPC475657
0.79	Intermediate Similarity	NPC469939
0.79	Intermediate Similarity	NPC63118
0.79	Intermediate Similarity	NPC49776
0.79	Intermediate Similarity	NPC115021
0.79	Intermediate Similarity	NPC242069
0.79	Intermediate Similarity	NPC139692
0.79	Intermediate Similarity	NPC474436
0.7895	Intermediate Similarity	NPC472440
0.789	Intermediate Similarity	NPC474315
0.7885	Intermediate Similarity	NPC469657
0.7885	Intermediate Similarity	NPC81530
0.7885	Intermediate Similarity	NPC477717
0.7885	Intermediate Similarity	NPC476888
0.7885	Intermediate Similarity	NPC474327
0.7885	Intermediate Similarity	NPC93744
0.7885	Intermediate Similarity	NPC244456
0.7879	Intermediate Similarity	NPC476369
0.7879	Intermediate Similarity	NPC476437
0.7876	Intermediate Similarity	NPC475775
0.7876	Intermediate Similarity	NPC476529

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 NPC63249 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	164
0.1-0.2	1362
0.2-0.3	3676
0.3-0.4	2640
0.4-0.5	802
0.5-0.6	227
0.6-0.7	196
0.7-0.8	82
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8113	Intermediate Similarity	NPD6686	Approved
0.7979	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7767	Intermediate Similarity	NPD7902	Approved
0.7723	Intermediate Similarity	NPD6399	Phase 3
0.7692	Intermediate Similarity	NPD7638	Approved
0.7647	Intermediate Similarity	NPD7748	Approved
0.7624	Intermediate Similarity	NPD7515	Phase 2
0.7619	Intermediate Similarity	NPD7640	Approved
0.7619	Intermediate Similarity	NPD7639	Approved
0.7544	Intermediate Similarity	NPD7115	Discovery
0.7524	Intermediate Similarity	NPD4225	Approved
0.7523	Intermediate Similarity	NPD6412	Phase 2
0.75	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7476	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7476	Intermediate Similarity	NPD7900	Approved
0.7429	Intermediate Similarity	NPD6083	Phase 2
0.7429	Intermediate Similarity	NPD6084	Phase 2
0.7374	Intermediate Similarity	NPD1694	Approved
0.7333	Intermediate Similarity	NPD7507	Approved
0.7327	Intermediate Similarity	NPD6672	Approved
0.7327	Intermediate Similarity	NPD5737	Approved
0.73	Intermediate Similarity	NPD6684	Approved
0.73	Intermediate Similarity	NPD7334	Approved
0.73	Intermediate Similarity	NPD7146	Approved
0.73	Intermediate Similarity	NPD7521	Approved
0.73	Intermediate Similarity	NPD6409	Approved
0.73	Intermediate Similarity	NPD5330	Approved
0.7273	Intermediate Similarity	NPD6400	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7196	Intermediate Similarity	NPD5696	Approved
0.7193	Intermediate Similarity	NPD6882	Approved
0.7157	Intermediate Similarity	NPD6903	Approved
0.7154	Intermediate Similarity	NPD7319	Approved
0.7143	Intermediate Similarity	NPD6899	Approved
0.7143	Intermediate Similarity	NPD6881	Approved
0.7129	Intermediate Similarity	NPD3618	Phase 1
0.7117	Intermediate Similarity	NPD5739	Approved
0.7117	Intermediate Similarity	NPD6675	Approved
0.7117	Intermediate Similarity	NPD6402	Approved
0.7117	Intermediate Similarity	NPD7128	Approved
0.7115	Intermediate Similarity	NPD5693	Phase 1
0.7115	Intermediate Similarity	NPD8035	Phase 2
0.7115	Intermediate Similarity	NPD8034	Phase 2
0.7105	Intermediate Similarity	NPD6649	Approved
0.7105	Intermediate Similarity	NPD6650	Approved
0.71	Intermediate Similarity	NPD3665	Phase 1
0.71	Intermediate Similarity	NPD3133	Approved
0.71	Intermediate Similarity	NPD3666	Approved
0.71	Intermediate Similarity	NPD4786	Approved
0.708	Intermediate Similarity	NPD6373	Approved
0.708	Intermediate Similarity	NPD6372	Approved
0.7075	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD5695	Phase 3
0.7075	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD7736	Approved
0.7071	Intermediate Similarity	NPD3667	Approved
0.7054	Intermediate Similarity	NPD5697	Approved
0.7041	Intermediate Similarity	NPD4695	Discontinued
0.7034	Intermediate Similarity	NPD7327	Approved
0.7034	Intermediate Similarity	NPD7328	Approved
0.7025	Intermediate Similarity	NPD8328	Phase 3
0.7019	Intermediate Similarity	NPD5785	Approved
0.7018	Intermediate Similarity	NPD7102	Approved
0.7018	Intermediate Similarity	NPD6883	Approved
0.7018	Intermediate Similarity	NPD7290	Approved
0.7	Intermediate Similarity	NPD8033	Approved
0.7	Intermediate Similarity	NPD7503	Approved
0.7	Intermediate Similarity	NPD7632	Discontinued
0.6991	Remote Similarity	NPD6011	Approved
0.6991	Remote Similarity	NPD7320	Approved
0.6983	Remote Similarity	NPD8133	Approved
0.6975	Remote Similarity	NPD7516	Approved
0.6957	Remote Similarity	NPD8130	Phase 1
0.6957	Remote Similarity	NPD6617	Approved
0.6957	Remote Similarity	NPD6869	Approved
0.6957	Remote Similarity	NPD6847	Approved
0.6952	Remote Similarity	NPD5281	Approved
0.6952	Remote Similarity	NPD6079	Approved
0.6952	Remote Similarity	NPD5284	Approved
0.693	Remote Similarity	NPD6012	Approved
0.693	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.693	Remote Similarity	NPD6014	Approved
0.693	Remote Similarity	NPD6013	Approved
0.693	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD6080	Approved
0.6923	Remote Similarity	NPD4753	Phase 2
0.6923	Remote Similarity	NPD6904	Approved
0.6923	Remote Similarity	NPD6673	Approved
0.6923	Remote Similarity	NPD5328	Approved
0.6917	Remote Similarity	NPD8294	Approved
0.6917	Remote Similarity	NPD8377	Approved
0.6916	Remote Similarity	NPD4629	Approved
0.6916	Remote Similarity	NPD5210	Approved
0.6903	Remote Similarity	NPD5701	Approved
0.6897	Remote Similarity	NPD8297	Approved
0.6897	Remote Similarity	NPD6053	Discontinued
0.6893	Remote Similarity	NPD3573	Approved
0.687	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.686	Remote Similarity	NPD8379	Approved
0.686	Remote Similarity	NPD8296	Approved
0.686	Remote Similarity	NPD8380	Approved
0.686	Remote Similarity	NPD8378	Approved
0.686	Remote Similarity	NPD8335	Approved
0.6852	Remote Similarity	NPD7614	Phase 1
0.6814	Remote Similarity	NPD6008	Approved
0.681	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6807	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6803	Remote Similarity	NPD6370	Approved
0.6796	Remote Similarity	NPD4519	Discontinued
0.6796	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6796	Remote Similarity	NPD4623	Approved
0.6792	Remote Similarity	NPD6411	Approved
0.6762	Remote Similarity	NPD6051	Approved
0.6733	Remote Similarity	NPD4221	Approved
0.6733	Remote Similarity	NPD4223	Phase 3
0.6729	Remote Similarity	NPD4202	Approved
0.6721	Remote Similarity	NPD8517	Approved
0.6721	Remote Similarity	NPD8515	Approved
0.6721	Remote Similarity	NPD8516	Approved
0.6721	Remote Similarity	NPD8513	Phase 3
0.672	Remote Similarity	NPD8293	Discontinued
0.6701	Remote Similarity	NPD8039	Approved
0.6699	Remote Similarity	NPD5329	Approved
0.6698	Remote Similarity	NPD46	Approved
0.6698	Remote Similarity	NPD6698	Approved
0.6698	Remote Similarity	NPD5207	Approved
0.6697	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6697	Remote Similarity	NPD7732	Phase 3
0.6697	Remote Similarity	NPD4697	Phase 3
0.6697	Remote Similarity	NPD5222	Approved
0.6697	Remote Similarity	NPD5221	Approved
0.6696	Remote Similarity	NPD5211	Phase 2
0.6694	Remote Similarity	NPD7492	Approved
0.6667	Remote Similarity	NPD5208	Approved
0.6667	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6404	Discontinued
0.6667	Remote Similarity	NPD4788	Approved
0.6667	Remote Similarity	NPD6009	Approved
0.6667	Remote Similarity	NPD5286	Approved
0.6667	Remote Similarity	NPD4696	Approved
0.6667	Remote Similarity	NPD6001	Approved
0.6667	Remote Similarity	NPD5285	Approved
0.664	Remote Similarity	NPD6616	Approved
0.6639	Remote Similarity	NPD6054	Approved
0.6636	Remote Similarity	NPD5173	Approved
0.6636	Remote Similarity	NPD4755	Approved
0.6636	Remote Similarity	NPD6050	Approved
0.6635	Remote Similarity	NPD6098	Approved
0.6635	Remote Similarity	NPD5279	Phase 3
0.6613	Remote Similarity	NPD6067	Discontinued
0.6612	Remote Similarity	NPD6335	Approved
0.6609	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6607	Remote Similarity	NPD5223	Approved
0.6604	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6604	Remote Similarity	NPD6101	Approved
0.6602	Remote Similarity	NPD3668	Phase 3
0.6602	Remote Similarity	NPD4197	Approved
0.6587	Remote Similarity	NPD7078	Approved
0.6585	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6583	Remote Similarity	NPD6274	Approved
0.6583	Remote Similarity	NPD6868	Approved
0.6581	Remote Similarity	NPD6371	Approved
0.6579	Remote Similarity	NPD5141	Approved
0.6577	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6574	Remote Similarity	NPD5779	Approved
0.6574	Remote Similarity	NPD5778	Approved
0.6557	Remote Similarity	NPD7101	Approved
0.6557	Remote Similarity	NPD7100	Approved
0.6555	Remote Similarity	NPD4632	Approved
0.6549	Remote Similarity	NPD5226	Approved
0.6549	Remote Similarity	NPD5225	Approved
0.6549	Remote Similarity	NPD5224	Approved
0.6549	Remote Similarity	NPD4633	Approved
0.6542	Remote Similarity	NPD5692	Phase 3
0.6538	Remote Similarity	NPD5363	Approved
0.6529	Remote Similarity	NPD6317	Approved
0.6518	Remote Similarity	NPD4700	Approved
0.6504	Remote Similarity	NPD6059	Approved
0.65	Remote Similarity	NPD3617	Approved
0.6491	Remote Similarity	NPD5175	Approved
0.6491	Remote Similarity	NPD6052	Approved
0.6491	Remote Similarity	NPD5174	Approved
0.6481	Remote Similarity	NPD7637	Suspended
0.6481	Remote Similarity	NPD5694	Approved
0.6476	Remote Similarity	NPD5690	Phase 2
0.6476	Remote Similarity	NPD4138	Approved
0.6476	Remote Similarity	NPD4690	Approved
0.6476	Remote Similarity	NPD5205	Approved
0.6476	Remote Similarity	NPD4689	Approved
0.6476	Remote Similarity	NPD4688	Approved
0.6476	Remote Similarity	NPD4693	Phase 3
0.6475	Remote Similarity	NPD6314	Approved
0.6475	Remote Similarity	NPD6313	Approved
0.6466	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD6015	Approved
0.6452	Remote Similarity	NPD6016	Approved
0.6436	Remote Similarity	NPD7645	Phase 2
0.6412	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.64	Remote Similarity	NPD5988	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