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CHEBI ONTOLOGY - ANNOTATIONS

The Chemical Entities of Biological Interest (ChEBI) ontology is downloaded weekly from EMBL-EBI at http://www.ebi.ac.uk/chebi/. The data is made available under the Creative Commons License (CC BY 3.0, http://creativecommons.org/licenses/by/3.0/). For more information see: Degtyarenko et al. (2008) ChEBI: a database and ontology for chemical entities of biological interest. Nucleic Acids Res. 36, D344–D350.

Term:tetrodotoxin
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Accession:CHEBI:9506 term browser browse the term
Definition:A quinazoline alkaloid that is a marine toxin isolated from fish such as puffer fish. It has been shown to exhibit potential neutotoxicity due to its ability to block voltage-gated sodium channels.
Synonyms:exact_synonym: (1R,5R,6R,7R,9S,11R,12R,13S,14S)-14-(hydroxymethyl)-3-imino-8,10-dioxa-2,4-diazatetracyclo[7.3.1.1(7,11).0(1,6)]tetradecane-5,9,12,13,14-pentol
 related_synonym: BJT 1;   Babylonia japonica toxin 1;   Formula=C11H17N3O8;   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;   InChIKey=CFMYXEVWODSLAX-QYIGHCJRSA-N;   SMILES=OC[C@@]1(O)[C@H]2O[C@@]3(O)O[C@@H]1[C@@H]1[C@@H](O)NC(=N)N[C@]1([C@H]2O)[C@@H]3O;   TTX;   fugu poison;   maculotoxin;   octahydro-12-(hydroxymethyl)-2-imino-5,9:7,10a-dimethano-10aH-[1,3]dioxocino[6,5-d]pyrimidine-4,7,10,11,12-pentol;   spheroidine;   tarichatoxin;   tetrodontoxin;   tetrodotoxine
 xref: AGR:IND607175662;   Beilstein:4156319;   CAS:4368-28-9;   DrugBank:DB05232;   HMDB:HMDB0258938;   KEGG:C11692;   KNApSAcK:C00055525
 xref_mesh: MESH:D013779
 xref: MetaCyc:CPD-19561;   PMID:11024497;   PMID:22163187;   PMID:22412801;   PMID:22798951;   PMID:23261990;   PMID:23661608;   PMID:23866757;   PMID:23980434;   PMID:24121556;   PMID:24295175;   PMID:24566728;   PMID:28648727;   PMID:28817087;   PMID:31029635;   PMID:31833474;   PMID:31985136;   PMID:32210160;   PMID:32415408;   PMID:32625458;   PMID:32849450;   PMID:33276679;   PMID:33450969;   PMID:33540777;   PMID:33651884;   PMID:33805908;   PMID:33807311;   PMID:33830775;   PMID:33913398;   PMID:33955768;   PMID:34067828;   PMID:34207879;   PMID:34209313;   PMID:34273772;   PMID:34357955;   PMID:34357968;   PMID:34437388;   PMID:34454925;   PMID:9559733;   Reaxys:6072946;   Wikipedia:Tetrodotoxin
 cyclic_relationship: is_conjugate_base_of CHEBI:180459



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tetrodotoxin term browser
Symbol Object Name Qualifiers Evidence Notes Source PubMed Reference(s) RGD Reference(s) Position
G Ahr aryl hydrocarbon receptor multiple interactions EXP Tetrodotoxin inhibits the reaction [Tetrachlorodibenzodioxin promotes the reaction [AHR protein binds to CYP1A1 promoter]] CTD PMID:17973980 NCBI chr 6:52,234,089...52,271,568
Ensembl chr 6:52,234,089...52,271,568
JBrowse link
G App amyloid beta precursor protein multiple interactions ISO Tetrodotoxin inhibits the reaction [DDT results in increased expression of APP mRNA]
Tetrodotoxin inhibits the reaction [DDT results in increased expression of APP mRNA]; Tetrodotoxin inhibits the reaction [DDT results in increased expression of APP protein]
CTD PMID:35946953 NCBI chr11:24,019,774...24,236,584
Ensembl chr11:24,019,778...24,236,561
JBrowse link
G Arc activity-regulated cytoskeleton-associated protein multiple interactions ISO Tetrodotoxin inhibits the reaction [ciguatoxin 3C results in increased expression of ARC mRNA] CTD PMID:25945544 NCBI chr 7:106,555,968...106,559,697
Ensembl chr 7:106,555,785...106,559,378
JBrowse link
G Bdnf brain-derived neurotrophic factor multiple interactions ISO
EXP
Tetrodotoxin inhibits the reaction [Azacitidine results in decreased methylation of BDNF promoter]; Tetrodotoxin inhibits the reaction [Azacitidine results in increased expression of BDNF mRNA]
Tetrodotoxin inhibits the reaction [decamethrin results in increased expression of BDNF mRNA]; Tetrodotoxin inhibits the reaction [Veratridine results in increased expression of BDNF mRNA]
3,5-dichloro-N-(1-(2,2-dimethyltetrahydropyran-4-ylmethyl)-4-fluoropiperidin-4-ylmethyl)benzamide promotes the reaction [Tetrodotoxin inhibits the reaction [Oxygen deficiency promotes the reaction [BDNF protein results in increased transport of Calcium]]]; Tetrodotoxin inhibits the reaction [Oxygen deficiency promotes the reaction [BDNF protein results in increased transport of Calcium]]
CTD PMID:16166269 PMID:18184782 PMID:26095976 NCBI chr 3:96,165,042...96,215,621
Ensembl chr 3:96,165,042...96,215,615
JBrowse link
G Camk4 calcium/calmodulin-dependent protein kinase IV multiple interactions EXP Tetrodotoxin inhibits the reaction [Tetrachlorodibenzodioxin affects the localization of CAMK4 protein] CTD PMID:17973980 NCBI chr18:24,582,988...24,811,918
Ensembl chr18:24,585,269...24,802,487
JBrowse link
G Chrna7 cholinergic receptor nicotinic alpha 7 subunit multiple interactions EXP Tetrodotoxin inhibits the reaction [[3-(4-hydroxy-2-methoxybenzylidene)anabaseine co-treated with 5-hydroxyindole] results in increased activity of CHRNA7 protein] CTD PMID:18321476 NCBI chr 1:116,711,559...116,837,269
Ensembl chr 1:116,714,711...116,837,240
JBrowse link
G Creb1 cAMP responsive element binding protein 1 multiple interactions EXP Tetrodotoxin inhibits the reaction [Tetrachlorodibenzodioxin promotes the reaction [CREB1 protein binds to CYP1A1 promoter]] CTD PMID:17973980 NCBI chr 9:65,903,511...65,972,562
Ensembl chr 9:65,903,547...65,970,816
JBrowse link
G Crh corticotropin releasing hormone decreases activity ISO Tetrodotoxin results in decreased activity of CRH protein CTD PMID:12906840 NCBI chr 2:102,143,055...102,144,919
Ensembl chr 2:102,143,055...102,144,919
JBrowse link
G Cybb cytochrome b-245 beta chain multiple interactions ISO [Tetrodotoxin co-treated with cariporide] inhibits the reaction [lipopolysaccharide, Escherichia coli O111 B4 results in increased expression of CYBB mRNA]; [Tetrodotoxin co-treated with cariporide] inhibits the reaction [lipopolysaccharide, Escherichia coli O111 B4 results in increased expression of CYBB protein]; Tetrodotoxin inhibits the reaction [lipopolysaccharide, Escherichia coli O111 B4 results in increased expression of CYBB mRNA]; Tetrodotoxin inhibits the reaction [lipopolysaccharide, Escherichia coli O111 B4 results in increased expression of CYBB protein] CTD PMID:24070585 NCBI chr  X:13,358,101...13,392,570
Ensembl chr  X:13,359,430...13,392,586
JBrowse link
G Cyp1a1 cytochrome P450, family 1, subfamily a, polypeptide 1 multiple interactions EXP Tetrodotoxin inhibits the reaction [Tetrachlorodibenzodioxin promotes the reaction [AHR protein binds to CYP1A1 promoter]]; Tetrodotoxin inhibits the reaction [Tetrachlorodibenzodioxin promotes the reaction [CREB1 protein binds to CYP1A1 promoter]] CTD PMID:17973980 NCBI chr 8:58,096,021...58,102,130
Ensembl chr 8:58,096,077...58,102,125
JBrowse link
G Cyp3a9 cytochrome P450, family 3, subfamily a, polypeptide 9 multiple interactions EXP [Bupivacaine co-treated with Tetrodotoxin co-treated with Dexamethasone] results in decreased expression of CYP3A9 mRNA CTD PMID:22341215 NCBI chr12:16,806,222...16,846,428
Ensembl chr12:16,806,207...16,846,422
JBrowse link
G Egr1 early growth response 1 multiple interactions ISO Tetrodotoxin inhibits the reaction [ciguatoxin 3C results in increased expression of EGR1 mRNA] CTD PMID:25945544 NCBI chr18:26,462,967...26,466,766
Ensembl chr18:26,462,981...26,466,766
JBrowse link
G Entpd4 ectonucleoside triphosphate diphosphohydrolase 4 multiple interactions EXP [Bupivacaine co-treated with Tetrodotoxin co-treated with Dexamethasone] results in decreased expression of ENTPD4 mRNA CTD PMID:22341215 NCBI chr15:44,630,878...44,658,654
Ensembl chr15:44,630,873...44,658,706
JBrowse link
G Erich5 glutamate-rich 5 increases expression ISO Tetrodotoxin results in increased expression of ERICH5 mRNA CTD PMID:26436198 NCBI chr 7:65,655,829...65,682,221
Ensembl chr 7:65,657,204...65,680,207
JBrowse link
G Fos Fos proto-oncogene, AP-1 transcription factor subunit decreases expression EXP Tetrodotoxin results in decreased expression of FOS mRNA; Tetrodotoxin results in decreased expression of FOS protein CTD PMID:7534335 NCBI chr 6:105,121,170...105,124,036
Ensembl chr 6:105,121,170...105,124,036
JBrowse link
G Gnrh1 gonadotropin releasing hormone 1 decreases secretion ISO Tetrodotoxin results in decreased secretion of GNRH1 protein CTD PMID:28731686 NCBI chr15:41,972,482...41,976,690
Ensembl chr15:41,972,905...41,973,581
Ensembl chr15:41,972,905...41,973,581
JBrowse link
G Gria1 glutamate ionotropic receptor AMPA type subunit 1 increases localization
multiple interactions
EXP Tetrodotoxin results in increased localization of GRIA1 protein
[Lead co-treated with Tetrodotoxin] results in increased expression of [GRIA1 protein binds to GRIA2 protein]
CTD PMID:19674091 PMID:29939358 NCBI chr10:41,210,713...41,527,283
Ensembl chr10:41,210,713...41,527,283
JBrowse link
G Gria2 glutamate ionotropic receptor AMPA type subunit 2 increases localization
multiple interactions
increases expression
EXP
ISO
Tetrodotoxin results in increased localization of GRIA2 protein
Tetrodotoxin inhibits the reaction [ciguatoxin 3C results in decreased expression of GRIA2 protein]
Tetrodotoxin results in increased expression of GRIA2 protein
[Lead co-treated with Tetrodotoxin] results in increased expression of [GRIA1 protein binds to GRIA2 protein]
CTD PMID:19674091 PMID:25945544 PMID:29939358 NCBI chr 2:165,949,379...166,069,510
Ensembl chr 2:165,947,521...166,069,510
JBrowse link
G Grin2a glutamate ionotropic receptor NMDA type subunit 2A multiple interactions ISO Tetrodotoxin inhibits the reaction [ciguatoxin 3C results in decreased expression of GRIN2A protein] CTD PMID:25945544 NCBI chr10:5,629,683...6,053,262
Ensembl chr10:5,631,369...6,044,637
JBrowse link
G Grin2b glutamate ionotropic receptor NMDA type subunit 2B multiple interactions ISO Tetrodotoxin inhibits the reaction [ciguatoxin 3C results in decreased expression of GRIN2B protein] CTD PMID:25945544 NCBI chr 4:168,580,824...169,044,110
Ensembl chr 4:168,599,546...169,042,279
JBrowse link
G Jun Jun proto-oncogene, AP-1 transcription factor subunit multiple interactions EXP Tetrodotoxin inhibits the reaction [4-OH-2',3,3',4',5'-pentachlorobiphenyl results in increased expression of JUN protein] CTD PMID:16300829 NCBI chr 5:109,894,175...109,897,268
Ensembl chr 5:109,893,145...109,897,656
JBrowse link
G Kcnc1 potassium voltage-gated channel subfamily C member 1 decreases expression EXP Tetrodotoxin results in decreased expression of KCNC1 mRNA CTD PMID:18775767 NCBI chr 1:96,902,953...96,944,744
Ensembl chr 1:96,902,953...96,944,744
JBrowse link
G Kcnc2 potassium voltage-gated channel subfamily C member 2 decreases expression EXP Tetrodotoxin results in decreased expression of KCNC2 mRNA; Tetrodotoxin results in decreased expression of KCNC2 protein CTD PMID:18775767 NCBI chr 7:47,700,035...47,883,979
Ensembl chr 7:47,700,288...47,883,968
JBrowse link
G Kiss1 KiSS-1 metastasis-suppressor multiple interactions ISO Tetrodotoxin inhibits the reaction [[KISS1 protein results in increased activity of KISS1R protein] which results in increased abundance of Calcium]; Tetrodotoxin promotes the reaction [2-aminoethyl diphenylborinate inhibits the reaction [[KISS1 protein results in increased activity of KISS1R protein] which results in increased abundance of Calcium]] CTD PMID:18948403 NCBI chr13:44,775,106...44,780,707
Ensembl chr13:44,774,823...44,780,612
JBrowse link
G Kiss1r KISS1 receptor multiple interactions ISO Tetrodotoxin inhibits the reaction [[KISS1 protein results in increased activity of KISS1R protein] which results in increased abundance of Calcium]; Tetrodotoxin promotes the reaction [2-aminoethyl diphenylborinate inhibits the reaction [[KISS1 protein results in increased activity of KISS1R protein] which results in increased abundance of Calcium]] CTD PMID:18948403 NCBI chr 7:9,785,135...9,790,283
Ensembl chr 7:9,785,135...9,788,793
JBrowse link
G Mapk1 mitogen activated protein kinase 1 multiple interactions
decreases phosphorylation
ISO
EXP
Tetrodotoxin inhibits the reaction [Permethrin results in increased phosphorylation of MAPK1 protein]
Tetrodotoxin results in decreased phosphorylation of MAPK1 protein
Tetrodotoxin inhibits the reaction [Bmk NT1 toxin, Buthus martensii Karsch results in increased phosphorylation of MAPK1 protein]
CTD PMID:15086530 PMID:30205134 PMID:30940546 NCBI chr11:83,957,813...84,023,629
Ensembl chr11:83,957,813...84,023,616
JBrowse link
G Mapk3 mitogen activated protein kinase 3 decreases phosphorylation
multiple interactions
ISO
EXP
Tetrodotoxin results in decreased phosphorylation of MAPK3 protein
Tetrodotoxin inhibits the reaction [Permethrin results in increased phosphorylation of MAPK3 protein]
Tetrodotoxin inhibits the reaction [Bmk NT1 toxin, Buthus martensii Karsch results in increased phosphorylation of MAPK3 protein]
CTD PMID:15086530 PMID:30205134 PMID:30940546 NCBI chr 1:181,366,646...181,372,863
Ensembl chr 1:181,366,637...181,372,863
JBrowse link
G Masp2 MBL associated serine protease 2 increases expression ISO Tetrodotoxin results in increased expression of MASP2 mRNA CTD PMID:26436198 NCBI chr 5:159,035,892...159,049,561
Ensembl chr 5:159,035,911...159,049,580
JBrowse link
G Npy neuropeptide Y multiple interactions EXP Tetrodotoxin inhibits the reaction [Veratridine results in increased expression of NPY mRNA] CTD PMID:2233698 NCBI chr 4:78,881,294...78,888,495
Ensembl chr 4:78,881,264...78,888,495
JBrowse link
G Prkcb protein kinase C, beta multiple interactions EXP [Bupivacaine co-treated with Tetrodotoxin co-treated with Dexamethasone] results in decreased expression of PRKCB mRNA CTD PMID:22341215 NCBI chr 1:176,832,173...177,163,539
Ensembl chr 1:176,832,226...177,163,536
JBrowse link
G Pvalb parvalbumin decreases expression EXP Tetrodotoxin results in decreased expression of PVALB mRNA CTD PMID:18775767 NCBI chr 7:109,772,939...109,787,954
Ensembl chr 7:109,772,593...109,784,561
JBrowse link
G Rhbdl2 rhomboid like 2 increases expression ISO Tetrodotoxin results in increased expression of RHBDL2 mRNA CTD PMID:26436198 NCBI chr 5:136,037,560...136,081,970
Ensembl chr 5:136,037,305...136,081,969
JBrowse link
G Scn1b sodium voltage-gated channel beta subunit 1 multiple interactions EXP Tetrodotoxin results in decreased activity of [SCN2A protein binds to SCN1B protein]; Tetrodotoxin results in decreased activity of [SCN8A protein binds to SCN1B protein binds to SCN2B protein] CTD PMID:9236205 PMID:21983428 NCBI chr 1:86,353,917...86,363,820
Ensembl chr 1:86,353,917...86,363,739
JBrowse link
G Scn2a sodium voltage-gated channel alpha subunit 2 multiple interactions
decreases activity
EXP
ISO
Tetrodotoxin results in decreased activity of [SCN2A protein binds to SCN1B protein]
Tetrodotoxin inhibits the reaction [decamethrin results in decreased expression of SCN2A mRNA]
Tetrodotoxin results in decreased activity of SCN2A protein
CTD PMID:9236205 PMID:22972919 PMID:25358543 NCBI chr 3:50,302,781...50,437,504
Ensembl chr 3:50,302,877...50,437,214
JBrowse link
G Scn2b sodium voltage-gated channel beta subunit 2 multiple interactions EXP Tetrodotoxin results in decreased activity of [SCN8A protein binds to SCN1B protein binds to SCN2B protein] CTD PMID:21983428 NCBI chr 8:45,425,629...45,437,765
Ensembl chr 8:45,425,629...45,437,765
JBrowse link
G Scn3a sodium voltage-gated channel alpha subunit 3 multiple interactions ISO Tetrodotoxin inhibits the reaction [decamethrin results in decreased expression of SCN3A mRNA] CTD PMID:25358543 NCBI chr 3:50,146,411...50,258,119
Ensembl chr 3:50,148,139...50,258,119
JBrowse link
G Scn5a sodium voltage-gated channel alpha subunit 5 decreases activity EXP Tetrodotoxin results in decreased activity of SCN5A protein CTD PMID:17978865 NCBI chr 8:119,220,905...119,318,816
Ensembl chr 8:119,220,905...119,318,769
JBrowse link
G Scn8a sodium voltage-gated channel alpha subunit 8 multiple interactions
decreases activity
ISO
EXP
[Tetrodotoxin results in decreased activity of [SCN8A protein co-treated with SCN9A protein]] which affects the transport of Sodium; Tetrodotoxin affects the reaction [lipopolysaccharide, Escherichia coli O111 B4 results in decreased expression of SCN8A protein]; Tetrodotoxin inhibits the reaction [SCN8A protein results in increased transport of Sodium]
Tetrodotoxin results in decreased activity of SCN8A protein
Tetrodotoxin results in decreased activity of [SCN8A protein binds to SCN1B protein binds to SCN2B protein]
CTD PMID:16020462 PMID:17522141 PMID:21983428 PMID:23382806 PMID:24070585 NCBI chr 7:131,982,152...132,156,075
Ensembl chr 7:131,982,480...132,151,292
JBrowse link
G Scn9a sodium voltage-gated channel alpha subunit 9 decreases activity
multiple interactions
ISO Tetrodotoxin results in decreased activity of SCN9A protein
[Tetrodotoxin results in decreased activity of [SCN8A protein co-treated with SCN9A protein]] which affects the transport of Sodium; Tetrodotoxin inhibits the reaction [SCN9A protein results in increased transport of Sodium]
CTD PMID:16020462 PMID:17522141 PMID:23382806 NCBI chr 3:51,145,148...51,293,342
Ensembl chr 3:51,145,146...51,293,516
JBrowse link
G Sct secretin multiple interactions EXP Tetrodotoxin inhibits the reaction [Potassium Chloride results in increased secretion of SCT protein] CTD PMID:15963647 PMID:16888165 NCBI chr 1:196,382,857...196,383,668
Ensembl chr 1:196,382,856...196,383,658
JBrowse link
G Slc9a1 solute carrier family 9 member A1 multiple interactions ISO [cariporide co-treated with Tetrodotoxin] inhibits the reaction [lipopolysaccharide, Escherichia coli O111 B4 results in increased expression of SLC9A1 protein]; Tetrodotoxin inhibits the reaction [lipopolysaccharide, Escherichia coli O111 B4 results in increased expression of SLC9A1 protein] CTD PMID:24070585 NCBI chr 5:145,576,341...145,629,630
Ensembl chr 5:145,576,334...145,629,624
JBrowse link
G Tcf25 transcription factor 25 increases expression ISO Tetrodotoxin results in increased expression of TCF25 mRNA CTD PMID:26436198 NCBI chr19:51,415,341...51,449,725
Ensembl chr19:51,415,543...51,449,723
JBrowse link
G Tnf tumor necrosis factor multiple interactions ISO cariporide promotes the reaction [Tetrodotoxin inhibits the reaction [lipopolysaccharide, Escherichia coli O111 B4 results in increased secretion of TNF protein]]; Tetrodotoxin inhibits the reaction [decamethrin results in increased secretion of TNF protein]; Tetrodotoxin inhibits the reaction [lipopolysaccharide, Escherichia coli O111 B4 results in increased secretion of TNF protein]; Tetrodotoxin inhibits the reaction [Permethrin results in increased secretion of TNF protein]; Tetrodotoxin promotes the reaction [cariporide inhibits the reaction [lipopolysaccharide, Escherichia coli O111 B4 results in increased secretion of TNF protein]] CTD PMID:24070585 PMID:27655349 NCBI chr20:3,622,011...3,624,629
Ensembl chr20:3,622,011...3,624,629
JBrowse link
Anhydrotetrodotoxin term browser
Symbol Object Name Qualifiers Evidence Notes Source PubMed Reference(s) RGD Reference(s) Position
G Scn8a sodium voltage-gated channel alpha subunit 8 decreases activity ISO anhydrotetrodotoxin results in decreased activity of SCN8A protein CTD PMID:17522141 NCBI chr 7:131,982,152...132,156,075
Ensembl chr 7:131,982,480...132,151,292
JBrowse link

Term paths to the root
Path 1
Term Annotations click to browse term
  CHEBI ontology 19811
    role 19818
      biological role 19785
        aetiopathogenetic role 19163
          neurotoxin 18154
            tetrodotoxin 43
              (+/-)-tetrodotoxin 0
              (11S,13S)-3-Amino-5,12,13,14-tetrahydroxy-14-(hydroxymethyl)-8,10-dioxa-2-aza-4-azoniatetracyclo[7.3.1.17,11.01,6]tetradec-3-en-9-olate 0
              (11s,13s)-3-amino-14-(hydroxymethyl)-8,10-dioxa-2,4-diazatetracyclo[7.3.1.1~7,11~.0~1,6~]tetradec-3-ene-5,9,12,13,14-pentol 0
              Anhydrotetrodotoxin 1
Path 2
Term Annotations click to browse term
  CHEBI ontology 19811
    subatomic particle 19809
      composite particle 19809
        hadron 19840
          baryon 19809
            nucleon 19809
              atomic nucleus 19809
                atom 19809
                  main group element atom 19759
                    p-block element atom 19759
                      carbon group element atom 19708
                        carbon atom 19734
                          organic molecular entity 19705
                            organic molecule 19658
                              organic cyclic compound 19471
                                organic heterocyclic compound 18862
                                  organic heteropolycyclic compound 18301
                                    organic heterobicyclic compound 17233
                                      quinazolines 540
                                        quinazoline alkaloid 43
                                          tetrodotoxin 43
                                            (+/-)-tetrodotoxin 0
                                            (11S,13S)-3-Amino-5,12,13,14-tetrahydroxy-14-(hydroxymethyl)-8,10-dioxa-2-aza-4-azoniatetracyclo[7.3.1.17,11.01,6]tetradec-3-en-9-olate 0
                                            (11s,13s)-3-amino-14-(hydroxymethyl)-8,10-dioxa-2,4-diazatetracyclo[7.3.1.1~7,11~.0~1,6~]tetradec-3-ene-5,9,12,13,14-pentol 0
                                            Anhydrotetrodotoxin 1
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