NPASS Natural Product

Natural Product: NPC68327

Natural Product ID:	NPC68327
Common Name:	Tetrodotoxin
IUPAC Name:
Synonyms:	Tetrodotoxin; tettrodotoxin
Molecular Formula:	C11H17N3O8
Standard InCHIKey:	CFMYXEVWODSLAX-QOZOJKKESA-N
Standard InCHI:	InChI=1S/C11H17N3O8/c12-8-13-6(17)2-4-9(19,1-15)5-3(16)10(2,14-8)7(18)11(20,21-4)22-5/h2-7,15-20H,1H2,(H3,12,13,14)/t2-,3-,4-,5+,6-,7+,9+,10-,11+/m1/s1
Canonical SMILES:	OC[C@@]1(O)[C@H]2O[C@]3(O[C@@H]1[C@H]1[C@@]([C@@H]2O)([C@@H]3O)NC(=N)N[C@@H]1O)O
First Find Year:
Max Developmental Stage:
Synthetic Gene Cluster:	;

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Reference
NPO7687	Bistorta affinis	Species	Polygonaceae	Eukaryota	UNPD*
NPO9186	Cestrum euanthes	Species	Solanaceae	Eukaryota	UNPD*
NPO9521	Viguiera schultzii	Species	Asteraceae	Eukaryota	UNPD*
NPO15493	Streptomyces sannurensis	Species	Streptomycetaceae	Bacteria	UNPD*
NPO19150	Swertia hookeri	Species	Gentianaceae	Eukaryota	UNPD*
NPO14598	Alternaria eichhorniae	Species	Pleosporaceae	Eukaryota	UNPD*
NPO23719	Senecio cachinalensis	Species	Asteraceae	Eukaryota	UNPD*
NPO23947	Boehmeria excelsa	Species	Urticaceae	Eukaryota	UNPD*
NPO19353	Tadehagi triquetrum	Species	Fabaceae	Eukaryota	UNPD*
NPO14720	Neopicrorhiza scrophulariiflora	Species	Plantaginaceae	Eukaryota	UNPD*
NPO19685	Streptomyces cyanogenus	Species	Streptomycetaceae	Bacteria	UNPD*
NPO17877	Knema austrosiamensis	Species	Myristicaceae	Eukaryota	UNPD*
NPO16257	Andromeda japonica	Species	Ericaceae	Eukaryota	UNPD*
NPO18990	Plagiorhegma dubium	Species	Berberidaceae	Eukaryota	UNPD*
NPO4175	Eremostachys loasifolia	Species	Lamiaceae	Eukaryota	UNPD*
NPO24161	Acremonium loliae	Species	NA	Eukaryota	UNPD*
NPO16383	Androstachys johnsonii	Species	Picrodendraceae	Eukaryota	UNPD*
NPO19892	Geranium onoei	Species	Geraniaceae	Eukaryota	UNPD*

Biological Activity

Activity Type	# Activity
EC50	1
IC50	12
Others	8

Activity Type	# Activity
Individual Protein	16
Organism	1
Others	2
Tissue	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT482	Individual Protein	Sodium channel protein type II alpha subunit	Rattus norvegicus	IC50	=	14	nM	8295214
NPT482	Individual Protein	Sodium channel protein type II alpha subunit	Rattus norvegicus	IC50	=	4	nM	9685245
NPT3706	Tissue	Atrium	Rattus norvegicus	Inhibition	=	64	%	18529044
NPT2856	Individual Protein	Sodium channel protein type V alpha subunit	Homo sapiens	Inhibition	=	79	%	18529044
NPT2856	Individual Protein	Sodium channel protein type V alpha subunit	Homo sapiens	Inhibition	=	87	%	18529044
NPT2856	Individual Protein	Sodium channel protein type V alpha subunit	Homo sapiens	Inhibition	=	79	%	19514733
NPT2856	Individual Protein	Sodium channel protein type V alpha subunit	Homo sapiens	Inhibition	=	87	%	19514733
NPT3706	Tissue	Atrium	Rattus norvegicus	Inhibition	=	64	%	19514733
NPT3708	Individual Protein	Sodium channel protein type IX alpha subunit	Homo sapiens	IC50	=	6	nM	21570288
NPT3710	Individual Protein	Sodium channel protein type X alpha subunit	Homo sapiens	IC50	>	30	nM	23121096
NPT2856	Individual Protein	Sodium channel protein type V alpha subunit	Homo sapiens	IC50	>	30	nM	23121096
NPT3711	Individual Protein	Sodium channel protein type XI alpha subunit	Homo sapiens	IC50	<	30	nM	23121096
NPT3708	Individual Protein	Sodium channel protein type IX alpha subunit	Homo sapiens	IC50	<	30	nM	23121096
NPT3712	Individual Protein	Sodium channel protein type VIII alpha subunit	Homo sapiens	IC50	<	30	nM	23121096
NPT3713	Individual Protein	Sodium channel protein type IV alpha subunit	Homo sapiens	IC50	<	30	nM	23121096
NPT3714	Individual Protein	Sodium channel protein type III alpha subunit	Homo sapiens	IC50	<	30	nM	23121096
NPT3715	Individual Protein	Sodium channel protein type II alpha subunit	Homo sapiens	IC50	<	30	nM	23121096
NPT3716	Individual Protein	Sodium channel protein type I alpha subunit	Homo sapiens	IC50	<	30	nM	23121096
NPT2	Others	Unspecified		EC50	=	2.1	nM	24654947
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Inhibition	=	100	%	24601592
NPT2	Others	Unspecified		Activity	=	88	%	26774037

Similar Natural Products 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 NPC68327 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	173
0.1-0.2	2400
0.2-0.3	14226
0.3-0.4	10628
0.4-0.5	3115
0.5-0.6	326
0.6-0.7	17
0.7-0.8	2
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9655	High Similarity	NPC75839
0.9652	High Similarity	NPC139857
0.72	Intermediate Similarity	NPC57436
0.72	Intermediate Similarity	NPC121479
0.6748	Remote Similarity	NPC56298
0.6748	Remote Similarity	NPC471628
0.6748	Remote Similarity	NPC315036
0.6618	Remote Similarity	NPC94319
0.6434	Remote Similarity	NPC262050
0.6338	Remote Similarity	NPC476967
0.6324	Remote Similarity	NPC475887
0.6268	Remote Similarity	NPC476497
0.6259	Remote Similarity	NPC20035
0.6232	Remote Similarity	NPC99905
0.6232	Remote Similarity	NPC208118
0.6232	Remote Similarity	NPC96080
0.6197	Remote Similarity	NPC476501
0.6111	Remote Similarity	NPC309249
0.6077	Remote Similarity	NPC221148
0.6061	Remote Similarity	NPC317534
0.6	Remote Similarity	NPC315334
0.5984	Remote Similarity	NPC314408
0.5984	Remote Similarity	NPC123746
0.5984	Remote Similarity	NPC314007
0.5984	Remote Similarity	NPC477060
0.5984	Remote Similarity	NPC43850
0.5984	Remote Similarity	NPC470282
0.5942	Remote Similarity	NPC476502
0.5906	Remote Similarity	NPC330590
0.5887	Remote Similarity	NPC176381
0.5887	Remote Similarity	NPC195969
0.5882	Remote Similarity	NPC271772
0.5882	Remote Similarity	NPC315969
0.5882	Remote Similarity	NPC36927
0.5862	Remote Similarity	NPC313762
0.5833	Remote Similarity	NPC263058
0.5811	Remote Similarity	NPC25455
0.5811	Remote Similarity	NPC15249
0.5809	Remote Similarity	NPC139778
0.5797	Remote Similarity	NPC241597
0.5776	Remote Similarity	NPC244539
0.5772	Remote Similarity	NPC122819
0.5772	Remote Similarity	NPC313552
0.5763	Remote Similarity	NPC98750
0.5762	Remote Similarity	NPC297058
0.5733	Remote Similarity	NPC150057
0.5733	Remote Similarity	NPC147753
0.5726	Remote Similarity	NPC214376
0.5714	Remote Similarity	NPC314398
0.5714	Remote Similarity	NPC314413
0.5714	Remote Similarity	NPC239705
0.5714	Remote Similarity	NPC313813
0.5714	Remote Similarity	NPC476955
0.5714	Remote Similarity	NPC70574
0.5704	Remote Similarity	NPC48127
0.5704	Remote Similarity	NPC8009
0.5704	Remote Similarity	NPC313272
0.5704	Remote Similarity	NPC267217
0.5704	Remote Similarity	NPC319537
0.5704	Remote Similarity	NPC83047
0.568	Remote Similarity	NPC470284
0.5672	Remote Similarity	NPC92874
0.5672	Remote Similarity	NPC62845
0.5672	Remote Similarity	NPC189854
0.5672	Remote Similarity	NPC166242
0.5672	Remote Similarity	NPC322449
0.5656	Remote Similarity	NPC241959
0.5645	Remote Similarity	NPC306838
0.563	Remote Similarity	NPC325900
0.563	Remote Similarity	NPC10897
0.5616	Remote Similarity	NPC296686

Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

● The left chart: Distribution of similarity level between NPC68327 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	97
0.1-0.2	1137
0.2-0.3	5372
0.3-0.4	2157
0.4-0.5	313
0.5-0.6	63
0.6-0.7	18
0.7-0.8	2
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9826	High Similarity	NPD591	Approved
0.9826	High Similarity	NPD577	Phase 3
0.72	Intermediate Similarity	NPD4833	Approved
0.72	Intermediate Similarity	NPD35	Approved
0.6748	Remote Similarity	NPD4838	Approved
0.6748	Remote Similarity	NPD4837	Approved
0.6748	Remote Similarity	NPD4836	Approved
0.6748	Remote Similarity	NPD4835	Approved
0.6618	Remote Similarity	NPD4827	Approved
0.6618	Remote Similarity	NPD4826	Approved
0.6618	Remote Similarity	NPD4828	Approved
0.6585	Remote Similarity	NPD4282	Approved
0.6496	Remote Similarity	NPD394	Phase 3
0.6484	Remote Similarity	NPD5376	Approved
0.6232	Remote Similarity	NPD8347	Approved
0.6232	Remote Similarity	NPD8345	Approved
0.6232	Remote Similarity	NPD8346	Approved
0.6119	Remote Similarity	NPD2690	Discontinued
0.6103	Remote Similarity	NPD3204	Clinical (unspecified phase)
0.6077	Remote Similarity	NPD1450	Approved
0.6077	Remote Similarity	NPD1449	Approved
0.6033	Remote Similarity	NPD3200	Clinical (unspecified phase)
0.5984	Remote Similarity	NPD3201	Approved
0.5984	Remote Similarity	NPD3202	Approved
0.5984	Remote Similarity	NPD3207	Approved
0.5984	Remote Similarity	NPD3208	Approved
0.5984	Remote Similarity	NPD3203	Approved
0.5984	Remote Similarity	NPD3209	Approved
0.5926	Remote Similarity	NPD8087	Discontinued
0.5906	Remote Similarity	NPD5381	Approved
0.5906	Remote Similarity	NPD5378	Approved
0.5906	Remote Similarity	NPD5377	Approved
0.5896	Remote Similarity	NPD8174	Phase 2
0.5887	Remote Similarity	NPD5795	Approved
0.5887	Remote Similarity	NPD5797	Approved
0.5887	Remote Similarity	NPD5796	Clinical (unspecified phase)
0.5887	Remote Similarity	NPD5794	Approved
0.5887	Remote Similarity	NPD5798	Approved
0.5827	Remote Similarity	NPD4830	Approved
0.5827	Remote Similarity	NPD4831	Approved
0.5827	Remote Similarity	NPD4832	Approved
0.5797	Remote Similarity	NPD3731	Phase 3
0.5772	Remote Similarity	NPD8449	Approved
0.5733	Remote Similarity	NPD8450	Suspended
0.5726	Remote Similarity	NPD2698	Approved
0.5704	Remote Similarity	NPD8307	Discontinued
0.5694	Remote Similarity	NPD6436	Phase 3
0.5672	Remote Similarity	NPD2700	Approved

Structure

CID68327 OpenBabel06191715402D 22 25 0 0 1 0 0 0 0 0999 V2000 -0.7994 3.2661 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0795 0.1553 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.5825 0.0222 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.1606 0.6857 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.6349 0.5691 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.9410 0.6528 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.2182 -1.3369 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.8027 -0.8394 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8740 1.5142 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.0795 -0.8396 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.3574 -0.8400 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.6431 -1.3245 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -3.8026 0.1554 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.9411 -1.3369 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.1973 4.0473 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2733 0.7128 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.9409 1.6231 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2182 -2.3046 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5578 2.4288 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0974 -1.7722 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3016 -0.1393 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 9 1 0 0 0 0 1 15 1 0 0 0 0 2 4 1 0 0 0 0 2 6 1 0 0 0 0 2 10 1 1 0 0 0 3 5 1 0 0 0 0 3 10 1 6 0 0 0 3 16 1 0 0 0 0 4 9 1 6 0 0 0 4 21 1 0 0 0 0 5 9 1 1 0 0 0 5 22 1 0 0 0 0 6 13 1 0 0 0 0 6 17 1 6 0 0 0 7 10 1 1 0 0 0 7 11 1 0 0 0 0 7 18 1 0 0 0 0 8 12 2 0 0 0 0 8 13 1 0 0 0 0 8 14 1 0 0 0 0 9 19 1 6 0 0 0 10 14 1 6 0 0 0 11 20 1 1 0 0 0 11 21 1 0 0 0 0 11 22 1 0 0 0 0 M END $$$$

External Identifiers

PubChem CID	11174599
ChEMBL	CHEMBL507974
ZINC

Physicochemical Properties

Molecular Weight:	319.10
ALogP:	-3.6838
MLogP:	1.46
XLogP:	-2.986
# Rotatable Bonds:	7
Polar Surface Area:	187.75
# H-Bond Aceptor:	11
# H-Bond Donor:	9
# Rings:	1
# Heavy Atoms:	22

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