NPASS Compound

Structure

CID297945 OpenBabel06191716102D 58 64 0 0 1 0 0 0 0 0999 V2000 1.7634 -2.4271 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8135 1.8271 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.0249 -3.9183 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.6229 -2.4183 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.4890 -3.9183 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.8909 0.5817 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0183 -3.5375 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 13.3550 -6.4183 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 13.3550 -5.4183 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3958 1.1226 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9836 0.3136 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3958 -1.1226 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9890 -0.2091 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.8909 -5.4183 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4781 1.2841 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4268 -1.4183 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4562 1.0762 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5608 -0.9183 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.7569 -5.9183 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.4890 -6.9183 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5823 -0.7045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.8909 -2.4183 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1810 -1.7226 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2147 -2.8452 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1756 -1.6180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4013 1.0181 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 9.8909 -4.4183 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 10.7569 -2.9183 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 12.4890 -4.9183 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 9.0249 0.0817 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9781 0.4181 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.8080 -1.9316 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 9.8909 -1.4183 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 7.2928 -0.9183 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9945 0.1045 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9945 -0.1045 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 8.1588 0.5817 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 10.7569 -3.9183 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 9.0249 -0.9183 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 7.2928 0.0817 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.7970 -2.1407 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2093 -2.9497 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.5608 0.0817 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 11.6229 -5.4183 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.4067 -0.9135 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 10.7569 -0.9183 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5878 0.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 8.1588 1.5817 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3903 -1.2271 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.7916 -2.2452 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.1047 -3.9442 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 11.6229 -6.4183 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 8.1588 -1.4183 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.6472 -0.3250 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8135 -1.8271 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 6.4268 0.5817 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 11.6229 -4.4183 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 25 1 0 0 0 0 5 29 1 0 0 0 0 6 30 2 0 0 0 0 8 9 1 0 0 0 0 8 20 1 0 0 0 0 9 29 1 0 0 0 0 10 11 2 0 0 0 0 10 26 1 0 0 0 0 12 13 1 0 0 0 0 12 32 1 0 0 0 0 13 36 1 0 0 0 0 14 19 1 0 0 0 0 14 27 1 0 0 0 0 15 17 1 0 0 0 0 15 31 1 0 0 0 0 16 18 1 0 0 0 0 18 43 1 0 0 0 0 20 52 1 0 0 0 0 21 25 1 0 0 0 0 21 35 1 0 0 0 0 22 28 1 0 0 0 0 22 33 1 0 0 0 0 23 25 2 0 0 0 0 24 42 1 0 0 0 0 26 2 1 6 0 0 0 27 3 1 1 0 0 0 27 38 1 0 0 0 0 28 4 1 6 0 0 0 29 44 1 6 0 0 0 30 37 1 0 0 0 0 30 39 1 0 0 0 0 31 11 1 1 0 0 0 31 54 1 0 0 0 0 32 24 1 6 0 0 0 32 55 1 0 0 0 0 33 46 1 1 0 0 0 34 16 1 6 0 0 0 34 40 1 0 0 0 0 34 53 1 0 0 0 0 35 26 1 6 0 0 0 35 56 1 0 0 0 0 36 45 1 1 0 0 0 36 47 1 0 0 0 0 37 40 1 0 0 0 0 37 48 1 6 0 0 0 38 28 1 1 0 0 0 38 58 1 0 0 0 0 39 33 1 1 0 0 0 39 53 1 0 0 0 0 40 57 1 1 0 0 0 41 42 1 0 0 0 0 41 49 2 0 0 0 0 41 50 1 0 0 0 0 42 7 1 6 0 0 0 42 51 1 0 0 0 0 43 17 1 1 0 0 0 43 54 1 0 0 0 0 43 57 1 0 0 0 0 44 19 1 1 0 0 0 44 52 1 0 0 0 0 44 58 1 0 0 0 0 45 23 1 6 0 0 0 45 55 1 0 0 0 0 45 56 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	818.48
Volume:	830.708
LogP:	4.772
LogD:	3.662
LogS:	-3.88
# Rotatable Bonds:	10
TPSA:	182.83
# H-Bond Aceptor:	13
# H-Bond Donor:	5
# Rings:	7
# Heavy Atoms:	13

MedChem Properties

QED Drug-Likeness Score:	0.176
Synthetic Accessibility Score:	7.426
Fsp3:	0.844
Lipinski Rule-of-5:	Rejected
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:	-5.627
MDCK Permeability:	6.304783892119303e-05
Pgp-inhibitor:	0.952
Pgp-substrate:	0.998
Human Intestinal Absorption (HIA):	0.913
20% Bioavailability (F20%):	0.899
30% Bioavailability (F30%):	0.792

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.002
Plasma Protein Binding (PPB):	85.15943145751953%
Volume Distribution (VD):	0.352
Pgp-substrate:	2.367311477661133%

ADMET: Metabolism

CYP1A2-inhibitor:	0.0
CYP1A2-substrate:	0.941
CYP2C19-inhibitor:	0.014
CYP2C19-substrate:	0.78
CYP2C9-inhibitor:	0.017
CYP2C9-substrate:	0.021
CYP2D6-inhibitor:	0.002
CYP2D6-substrate:	0.074
CYP3A4-inhibitor:	0.132
CYP3A4-substrate:	0.319

ADMET: Excretion

Clearance (CL):	2.27
Half-life (T1/2):	0.063

ADMET: Toxicity

hERG Blockers:	0.597
Human Hepatotoxicity (H-HT):	0.959
Drug-inuced Liver Injury (DILI):	0.951
AMES Toxicity:	0.494
Rat Oral Acute Toxicity:	0.989
Maximum Recommended Daily Dose:	0.987
Skin Sensitization:	0.597
Carcinogencity:	0.137
Eye Corrosion:	0.003
Eye Irritation:	0.008
Respiratory Toxicity:	0.971

Download Data

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

Natural Product: NPC297945

Natural Product ID:	NPC297945
*Common Name:**	Dinophysistoxin 1
IUPAC Name:	(2R)-3-[(2S,6R,8S,11R)-2-[(E,2R)-4-[(2S,2'R,4R,4aS,6R,8aR)-2-[(1S,3S)-3-[(2S,3R,6R,11R)-3,11-dimethyl-1,7-dioxaspiro[5.5]undecan-2-yl]-1-hydroxybutyl]-4-hydroxy-3-methylidenespiro[4a,7,8,8a-tetrahydro-4H-pyrano[3,2-b]pyran-6,5'-oxolane]-2'-yl]but-3-en-2-yl]-11-hydroxy-4-methyl-1,7-dioxaspiro[5.5]undec-4-en-8-yl]-2-hydroxy-2-methylpropanoic acid
Synonyms:	Dinophysistoxin 1
Standard InCHIKey:	CLBIEZBAENPDFY-HNXGFDTJSA-N
Standard InCHI:	InChI=1S/C45H70O13/c1-25-21-35(56-45(23-25)36(47)13-12-32(55-45)24-42(7,51)41(49)50)26(2)10-11-31-15-17-43(54-31)18-16-34-40(57-43)37(48)30(6)39(53-34)33(46)22-28(4)38-27(3)14-19-44(58-38)29(5)9-8-20-52-44/h10-11,23,26-29,31-40,46-48,51H,6,8-9,12-22,24H2,1-5,7H3,(H,49,50)/b11-10+/t26-,27-,28+,29-,31+,32+,33+,34-,35+,36-,37-,38+,39+,40-,42-,43-,44-,45-/m1/s1
SMILES:	CC1=C[C@]2([C@@H](CC[C@@H](C[C@](C)(C(=O)O)O)O2)O)O[C@@H](C1)[C@H](C)/C=C/[C@H]1CC[C@@]2(CC[C@@H]3[C@H]([C@@H](C(=C)[C@@H]([C@H](C[C@H](C)[C@@H]4[C@H](C)CC[C@]5([C@H](C)CCCO5)O4)O)O3)O)O2)O1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL443145
PubChem CID:	20055920
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0000254] Ethers [CHEMONTID:0001656] Acetals [CHEMONTID:0004472] Ketals

*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
NPO40765	Phakellia species	Species	Axinellidae	Eukaryota	n.a.	n.a.	n.a.	PMID[7623052]
NPO11764	Artemisia tanacetifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10674	Pancovia laurentii	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	1
Others	1

Activity Type	# Activity
Cell Line	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT137	Cell Line	L1210	Mus musculus	IC50	=	0.002	ug.mL-1	PMID[545979]
NPT27	Others	Unspecified		IZ	=	0.0	mm	PMID[545979]

☑ 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 NPC297945 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	235
0.1-0.2	1357
0.2-0.3	4251
0.3-0.4	9912
0.4-0.5	12104
0.5-0.6	8130
0.6-0.7	4850
0.7-0.8	1791
0.8-0.85	57
0.85-0.9	7
0.9-0.95	0
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC126897
0.8879	High Similarity	NPC313668
0.8879	High Similarity	NPC315836
0.8857	High Similarity	NPC231271
0.8857	High Similarity	NPC470519
0.8584	High Similarity	NPC93688
0.8584	High Similarity	NPC109603
0.8362	Intermediate Similarity	NPC170880
0.8362	Intermediate Similarity	NPC183353
0.8362	Intermediate Similarity	NPC469812
0.8091	Intermediate Similarity	NPC472749
0.8091	Intermediate Similarity	NPC315070
0.8091	Intermediate Similarity	NPC472751
0.8	Intermediate Similarity	NPC472748
0.8	Intermediate Similarity	NPC220964
0.8	Intermediate Similarity	NPC475676
0.7982	Intermediate Similarity	NPC473596
0.7981	Intermediate Similarity	NPC472197
0.7951	Intermediate Similarity	NPC220838
0.7951	Intermediate Similarity	NPC45606
0.7928	Intermediate Similarity	NPC476740
0.7928	Intermediate Similarity	NPC476738
0.7925	Intermediate Similarity	NPC36954
0.7909	Intermediate Similarity	NPC472747
0.7909	Intermediate Similarity	NPC472750
0.7909	Intermediate Similarity	NPC309398
0.7909	Intermediate Similarity	NPC4620
0.7905	Intermediate Similarity	NPC320089
0.7903	Intermediate Similarity	NPC475177
0.7903	Intermediate Similarity	NPC324933
0.7903	Intermediate Similarity	NPC196874
0.7903	Intermediate Similarity	NPC183816
0.7903	Intermediate Similarity	NPC473679
0.7903	Intermediate Similarity	NPC319719
0.7903	Intermediate Similarity	NPC475444
0.7903	Intermediate Similarity	NPC322904
0.7903	Intermediate Similarity	NPC233223
0.7876	Intermediate Similarity	NPC15218
0.787	Intermediate Similarity	NPC203627
0.785	Intermediate Similarity	NPC54731
0.7845	Intermediate Similarity	NPC308858
0.7845	Intermediate Similarity	NPC475537
0.783	Intermediate Similarity	NPC71589
0.783	Intermediate Similarity	NPC256368
0.7826	Intermediate Similarity	NPC312498
0.7826	Intermediate Similarity	NPC473849
0.7823	Intermediate Similarity	NPC311178
0.7823	Intermediate Similarity	NPC222951
0.7823	Intermediate Similarity	NPC300655
0.7823	Intermediate Similarity	NPC43589
0.7815	Intermediate Similarity	NPC268184
0.7805	Intermediate Similarity	NPC470476
0.7788	Intermediate Similarity	NPC169888
0.7788	Intermediate Similarity	NPC474664
0.7788	Intermediate Similarity	NPC55972
0.7788	Intermediate Similarity	NPC233379
0.7788	Intermediate Similarity	NPC14862
0.7788	Intermediate Similarity	NPC327286
0.7787	Intermediate Similarity	NPC297950
0.7768	Intermediate Similarity	NPC478038
0.7748	Intermediate Similarity	NPC474581
0.7748	Intermediate Similarity	NPC475367
0.7748	Intermediate Similarity	NPC473816
0.7736	Intermediate Similarity	NPC475912
0.7736	Intermediate Similarity	NPC476300
0.7731	Intermediate Similarity	NPC122971
0.7727	Intermediate Similarity	NPC475157
0.7727	Intermediate Similarity	NPC471637
0.7727	Intermediate Similarity	NPC475655
0.7727	Intermediate Similarity	NPC2313
0.7727	Intermediate Similarity	NPC154132
0.7727	Intermediate Similarity	NPC57586
0.7724	Intermediate Similarity	NPC470780
0.7706	Intermediate Similarity	NPC308567
0.7706	Intermediate Similarity	NPC83895
0.7706	Intermediate Similarity	NPC187761
0.7706	Intermediate Similarity	NPC261377
0.7706	Intermediate Similarity	NPC187268
0.7706	Intermediate Similarity	NPC255592
0.7706	Intermediate Similarity	NPC475653
0.7699	Intermediate Similarity	NPC72813
0.7699	Intermediate Similarity	NPC474421
0.7699	Intermediate Similarity	NPC326994
0.7699	Intermediate Similarity	NPC324327
0.7699	Intermediate Similarity	NPC194620
0.7686	Intermediate Similarity	NPC473231
0.7685	Intermediate Similarity	NPC476315
0.7685	Intermediate Similarity	NPC306041
0.7664	Intermediate Similarity	NPC472198
0.7661	Intermediate Similarity	NPC112492
0.7661	Intermediate Similarity	NPC472269
0.7661	Intermediate Similarity	NPC470475
0.7661	Intermediate Similarity	NPC472270
0.7661	Intermediate Similarity	NPC23020
0.7661	Intermediate Similarity	NPC472268
0.7658	Intermediate Similarity	NPC313569
0.7647	Intermediate Similarity	NPC36831
0.7642	Intermediate Similarity	NPC470379
0.7642	Intermediate Similarity	NPC470373
0.7642	Intermediate Similarity	NPC30515
0.7642	Intermediate Similarity	NPC184463
0.7642	Intermediate Similarity	NPC472199
0.7632	Intermediate Similarity	NPC193765
0.7632	Intermediate Similarity	NPC473807
0.7627	Intermediate Similarity	NPC259306
0.7627	Intermediate Similarity	NPC470628
0.7627	Intermediate Similarity	NPC474046
0.7615	Intermediate Similarity	NPC120299
0.7615	Intermediate Similarity	NPC40812
0.7615	Intermediate Similarity	NPC475332
0.7615	Intermediate Similarity	NPC266842
0.7611	Intermediate Similarity	NPC16313
0.7611	Intermediate Similarity	NPC9303
0.7611	Intermediate Similarity	NPC475802
0.7607	Intermediate Similarity	NPC474410
0.7607	Intermediate Similarity	NPC293658
0.7603	Intermediate Similarity	NPC170084
0.7603	Intermediate Similarity	NPC473250
0.7603	Intermediate Similarity	NPC476204
0.7593	Intermediate Similarity	NPC270013
0.7593	Intermediate Similarity	NPC14961
0.7589	Intermediate Similarity	NPC197736
0.7583	Intermediate Similarity	NPC477464
0.7583	Intermediate Similarity	NPC477071
0.757	Intermediate Similarity	NPC472196
0.757	Intermediate Similarity	NPC478036
0.757	Intermediate Similarity	NPC238090
0.757	Intermediate Similarity	NPC472195
0.757	Intermediate Similarity	NPC478037
0.7563	Intermediate Similarity	NPC148417
0.7563	Intermediate Similarity	NPC136768
0.7563	Intermediate Similarity	NPC110633
0.7563	Intermediate Similarity	NPC68175
0.7563	Intermediate Similarity	NPC473590
0.7559	Intermediate Similarity	NPC316915
0.7547	Intermediate Similarity	NPC474761
0.7547	Intermediate Similarity	NPC51004
0.7547	Intermediate Similarity	NPC476004
0.7547	Intermediate Similarity	NPC177668
0.7542	Intermediate Similarity	NPC469877
0.7542	Intermediate Similarity	NPC470919
0.7542	Intermediate Similarity	NPC181145
0.7523	Intermediate Similarity	NPC279621
0.7523	Intermediate Similarity	NPC255410
0.7522	Intermediate Similarity	NPC472756
0.7522	Intermediate Similarity	NPC258532
0.7521	Intermediate Similarity	NPC302146
0.7521	Intermediate Similarity	NPC48692
0.7521	Intermediate Similarity	NPC473130
0.7521	Intermediate Similarity	NPC476150
0.7521	Intermediate Similarity	NPC476127
0.75	Intermediate Similarity	NPC159698
0.75	Intermediate Similarity	NPC83005
0.75	Intermediate Similarity	NPC472754
0.75	Intermediate Similarity	NPC238264
0.75	Intermediate Similarity	NPC477345
0.75	Intermediate Similarity	NPC44682
0.75	Intermediate Similarity	NPC470218
0.75	Intermediate Similarity	NPC149371
0.75	Intermediate Similarity	NPC115257
0.75	Intermediate Similarity	NPC161816
0.75	Intermediate Similarity	NPC471548
0.75	Intermediate Similarity	NPC5103
0.75	Intermediate Similarity	NPC81386
0.75	Intermediate Similarity	NPC475899
0.75	Intermediate Similarity	NPC474035
0.75	Intermediate Similarity	NPC477348
0.75	Intermediate Similarity	NPC195510
0.75	Intermediate Similarity	NPC311163
0.75	Intermediate Similarity	NPC13171
0.75	Intermediate Similarity	NPC163409
0.75	Intermediate Similarity	NPC45475
0.748	Intermediate Similarity	NPC41129
0.748	Intermediate Similarity	NPC256983
0.748	Intermediate Similarity	NPC231240
0.7479	Intermediate Similarity	NPC471384
0.7479	Intermediate Similarity	NPC474734
0.7479	Intermediate Similarity	NPC58448
0.7479	Intermediate Similarity	NPC189126
0.7479	Intermediate Similarity	NPC161674
0.7479	Intermediate Similarity	NPC160415
0.7478	Intermediate Similarity	NPC392
0.7478	Intermediate Similarity	NPC177524
0.7478	Intermediate Similarity	NPC475275
0.7478	Intermediate Similarity	NPC219900
0.7478	Intermediate Similarity	NPC473771
0.746	Intermediate Similarity	NPC476966
0.746	Intermediate Similarity	NPC471407
0.746	Intermediate Similarity	NPC477235
0.7459	Intermediate Similarity	NPC477463
0.7459	Intermediate Similarity	NPC473228
0.7459	Intermediate Similarity	NPC293031
0.7459	Intermediate Similarity	NPC275225
0.7459	Intermediate Similarity	NPC68767
0.7459	Intermediate Similarity	NPC51099
0.7459	Intermediate Similarity	NPC470829
0.7458	Intermediate Similarity	NPC311592
0.7458	Intermediate Similarity	NPC204458
0.7458	Intermediate Similarity	NPC469454
0.7458	Intermediate Similarity	NPC189884

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 NPC297945 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	194
0.1-0.2	1505
0.2-0.3	3803
0.3-0.4	2475
0.4-0.5	710
0.5-0.6	346
0.6-0.7	93
0.7-0.8	19
0.8-0.85	3
0.85-0.9	1
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
1.0	High Similarity	NPD8413	Clinical (unspecified phase)
0.8362	Intermediate Similarity	NPD8516	Approved
0.8362	Intermediate Similarity	NPD8515	Approved
0.8362	Intermediate Similarity	NPD8517	Approved
0.8362	Intermediate Similarity	NPD8513	Phase 3
0.787	Intermediate Similarity	NPD8029	Clinical (unspecified phase)
0.7547	Intermediate Similarity	NPD6698	Approved
0.7547	Intermediate Similarity	NPD46	Approved
0.7478	Intermediate Similarity	NPD6686	Approved
0.744	Intermediate Similarity	NPD8074	Phase 3
0.7391	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD7983	Approved
0.7311	Intermediate Similarity	NPD8133	Approved
0.7064	Intermediate Similarity	NPD7838	Discovery
0.7	Intermediate Similarity	NPD8392	Approved
0.7	Intermediate Similarity	NPD8391	Approved
0.7	Intermediate Similarity	NPD8390	Approved
0.6992	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.696	Remote Similarity	NPD8294	Approved
0.696	Remote Similarity	NPD8377	Approved
0.6953	Remote Similarity	NPD8451	Approved
0.6929	Remote Similarity	NPD8328	Phase 3
0.6905	Remote Similarity	NPD8296	Approved
0.6905	Remote Similarity	NPD8378	Approved
0.6905	Remote Similarity	NPD8379	Approved
0.6905	Remote Similarity	NPD8335	Approved
0.6905	Remote Similarity	NPD8380	Approved
0.6905	Remote Similarity	NPD8033	Approved
0.6903	Remote Similarity	NPD7839	Suspended
0.6899	Remote Similarity	NPD8448	Approved
0.6875	Remote Similarity	NPD8299	Approved
0.6875	Remote Similarity	NPD8340	Approved
0.6875	Remote Similarity	NPD8342	Approved
0.6875	Remote Similarity	NPD8341	Approved
0.6833	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6822	Remote Similarity	NPD7507	Approved
0.6815	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6777	Remote Similarity	NPD6371	Approved
0.6772	Remote Similarity	NPD7503	Approved
0.672	Remote Similarity	NPD7115	Discovery
0.6667	Remote Similarity	NPD7830	Approved
0.6667	Remote Similarity	NPD7829	Approved
0.6667	Remote Similarity	NPD7319	Approved
0.6667	Remote Similarity	NPD6412	Phase 2
0.6637	Remote Similarity	NPD5778	Approved
0.6637	Remote Similarity	NPD5779	Approved
0.6612	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6579	Remote Similarity	NPD5282	Discontinued
0.6574	Remote Similarity	NPD7154	Phase 3
0.6535	Remote Similarity	NPD7327	Approved
0.6535	Remote Similarity	NPD7328	Approved
0.6532	Remote Similarity	NPD6053	Discontinued
0.6525	Remote Similarity	NPD5344	Discontinued
0.6512	Remote Similarity	NPD8444	Approved
0.6512	Remote Similarity	NPD8269	Approved
0.6512	Remote Similarity	NPD8268	Approved
0.6512	Remote Similarity	NPD8267	Approved
0.6512	Remote Similarity	NPD8266	Approved
0.6512	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.6496	Remote Similarity	NPD8387	Clinical (unspecified phase)
0.6496	Remote Similarity	NPD4225	Approved
0.6486	Remote Similarity	NPD4250	Approved
0.6486	Remote Similarity	NPD4251	Approved
0.6484	Remote Similarity	NPD7516	Approved
0.6466	Remote Similarity	NPD7736	Approved
0.6462	Remote Similarity	NPD8080	Discontinued
0.6457	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.6455	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6439	Remote Similarity	NPD8273	Phase 1
0.6423	Remote Similarity	NPD8415	Approved
0.6412	Remote Similarity	NPD7642	Approved
0.6396	Remote Similarity	NPD4249	Approved
0.6372	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6372	Remote Similarity	NPD6101	Approved
0.6364	Remote Similarity	NPD7492	Approved
0.6316	Remote Similarity	NPD6616	Approved
0.6308	Remote Similarity	NPD6054	Approved
0.6303	Remote Similarity	NPD7639	Approved
0.6303	Remote Similarity	NPD7640	Approved
0.6296	Remote Similarity	NPD4819	Approved
0.6296	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD4822	Approved
0.6296	Remote Similarity	NPD4821	Approved
0.6296	Remote Similarity	NPD4820	Approved
0.629	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6279	Remote Similarity	NPD7641	Discontinued
0.6273	Remote Similarity	NPD5362	Discontinued
0.627	Remote Similarity	NPD6882	Approved
0.627	Remote Similarity	NPD8297	Approved
0.6269	Remote Similarity	NPD8293	Discontinued
0.6269	Remote Similarity	NPD7078	Approved
0.6261	Remote Similarity	NPD6411	Approved
0.624	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6239	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6228	Remote Similarity	NPD1695	Approved
0.6218	Remote Similarity	NPD7638	Approved
0.6216	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6212	Remote Similarity	NPD6370	Approved
0.6204	Remote Similarity	NPD7260	Phase 2
0.6202	Remote Similarity	NPD6009	Approved
0.6183	Remote Similarity	NPD6319	Approved
0.6183	Remote Similarity	NPD6059	Approved
0.6182	Remote Similarity	NPD4269	Approved
0.6182	Remote Similarity	NPD4270	Approved
0.6174	Remote Similarity	NPD5785	Approved
0.6167	Remote Similarity	NPD6648	Approved
0.6136	Remote Similarity	NPD6015	Approved
0.6136	Remote Similarity	NPD6921	Approved
0.6136	Remote Similarity	NPD6016	Approved
0.6121	Remote Similarity	NPD7637	Suspended
0.6111	Remote Similarity	NPD4268	Approved
0.6111	Remote Similarity	NPD4271	Approved
0.6106	Remote Similarity	NPD5786	Approved
0.6094	Remote Similarity	NPD4632	Approved
0.6091	Remote Similarity	NPD5369	Approved
0.609	Remote Similarity	NPD5988	Approved
0.6068	Remote Similarity	NPD6399	Phase 3
0.6063	Remote Similarity	NPD6650	Approved
0.6063	Remote Similarity	NPD6649	Approved
0.6036	Remote Similarity	NPD6435	Approved
0.6032	Remote Similarity	NPD6372	Approved
0.6032	Remote Similarity	NPD6373	Approved
0.6018	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6018	Remote Similarity	NPD5363	Approved
0.6	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.6	Remote Similarity	NPD6083	Phase 2
0.6	Remote Similarity	NPD7902	Approved
0.6	Remote Similarity	NPD6084	Phase 2
0.6	Remote Similarity	NPD4252	Approved
0.5984	Remote Similarity	NPD6421	Discontinued
0.5982	Remote Similarity	NPD6110	Phase 1
0.5968	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.5963	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.5952	Remote Similarity	NPD6881	Approved
0.5952	Remote Similarity	NPD6899	Approved
0.5938	Remote Similarity	NPD8130	Phase 1
0.5931	Remote Similarity	NPD8384	Approved
0.5929	Remote Similarity	NPD6845	Suspended
0.592	Remote Similarity	NPD7128	Approved
0.592	Remote Similarity	NPD6402	Approved
0.592	Remote Similarity	NPD5739	Approved
0.592	Remote Similarity	NPD6675	Approved
0.5917	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.5913	Remote Similarity	NPD7524	Approved
0.5909	Remote Similarity	NPD7329	Approved
0.5882	Remote Similarity	NPD7748	Approved
0.5877	Remote Similarity	NPD1694	Approved
0.5873	Remote Similarity	NPD5697	Approved
0.5859	Remote Similarity	NPD6883	Approved
0.5859	Remote Similarity	NPD7102	Approved
0.5859	Remote Similarity	NPD7290	Approved
0.5856	Remote Similarity	NPD5368	Approved
0.5841	Remote Similarity	NPD5332	Approved
0.5841	Remote Similarity	NPD5331	Approved
0.5833	Remote Similarity	NPD8039	Approved
0.5833	Remote Similarity	NPD5695	Phase 3
0.5833	Remote Similarity	NPD7500	Approved
0.5827	Remote Similarity	NPD7320	Approved
0.582	Remote Similarity	NPD5696	Approved
0.5814	Remote Similarity	NPD6617	Approved
0.5814	Remote Similarity	NPD6847	Approved
0.5814	Remote Similarity	NPD6869	Approved
0.5814	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.5809	Remote Similarity	NPD7604	Phase 2
0.5806	Remote Similarity	NPD8138	Approved
0.5806	Remote Similarity	NPD7632	Discontinued
0.5806	Remote Similarity	NPD8086	Approved
0.5806	Remote Similarity	NPD8139	Approved
0.5806	Remote Similarity	NPD8084	Approved
0.5806	Remote Similarity	NPD8085	Approved
0.5806	Remote Similarity	NPD8082	Approved
0.5806	Remote Similarity	NPD8083	Approved
0.5804	Remote Similarity	NPD4790	Discontinued
0.5789	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.5786	Remote Similarity	NPD5956	Approved
0.5784	Remote Similarity	NPD3197	Phase 1
0.5781	Remote Similarity	NPD6013	Approved
0.5781	Remote Similarity	NPD6014	Approved
0.5781	Remote Similarity	NPD6012	Approved
0.5778	Remote Similarity	NPD5983	Phase 2
0.576	Remote Similarity	NPD8275	Approved
0.576	Remote Similarity	NPD8276	Approved
0.5755	Remote Similarity	NPD6033	Approved
0.5752	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.575	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.575	Remote Similarity	NPD7900	Approved
0.5748	Remote Similarity	NPD5701	Approved
0.5725	Remote Similarity	NPD6336	Discontinued
0.5714	Remote Similarity	NPD7505	Discontinued
0.5714	Remote Similarity	NPD8034	Phase 2
0.5714	Remote Similarity	NPD8035	Phase 2
0.5714	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD8081	Approved
0.5714	Remote Similarity	NPD7515	Phase 2
0.5704	Remote Similarity	NPD8449	Approved
0.5703	Remote Similarity	NPD6011	Approved
0.5702	Remote Similarity	NPD6695	Phase 3
0.5692	Remote Similarity	NPD2204	Approved
0.568	Remote Similarity	NPD5211	Phase 2

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