Showing Compound Yessotoxin (FDB011347)

Record Information

Version

1.0

Creation date

2010-04-08 22:09:35 UTC

Update date

2019-11-26 03:04:50 UTC

Primary ID

FDB011347

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Yessotoxin

Description

Yessotoxin belongs to the class of organic compounds known as ciguatera toxins. These are lipid-soluble polyether compounds consisting of 13 to 14 rings fused by ether linkages into a most rigid ladder-like structure. Yessotoxin has been detected, but not quantified in, mollusks. This could make yessotoxin a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on Yessotoxin.

CAS Number

112514-54-2

Structure

MOL SDF PDB SMILES InChI

Synonyms

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Synonym	Source
Yessotoxin	MeSH
{34-hydroxy-40-[(3E)-2-hydroxy-5-methylideneocta-3,7-dien-2-yl]-13,25,27,30,35-pentamethyl-39-methylidene-13-[2-(sulfooxy)ethyl]-4,8,12,17,21,26,32,36,41,45,49-undecaoxaundecacyclo[25.22.0.0³,²⁵.0⁵,²².0⁷,²⁰.0⁹,¹⁸.0¹¹,¹⁶.0³¹,⁴⁸.0³³,⁴⁶.0³⁵,⁴⁴.0³⁷,⁴²]nonatetracontan-14-yl}oxidanesulfonate	HMDB
{34-hydroxy-40-[(3E)-2-hydroxy-5-methylideneocta-3,7-dien-2-yl]-13,25,27,30,35-pentamethyl-39-methylidene-13-[2-(sulphooxy)ethyl]-4,8,12,17,21,26,32,36,41,45,49-undecaoxaundecacyclo[25.22.0.0³,²⁵.0⁵,²².0⁷,²⁰.0⁹,¹⁸.0¹¹,¹⁶.0³¹,⁴⁸.0³³,⁴⁶.0³⁵,⁴⁴.0³⁷,⁴²]nonatetracontan-14-yl}oxidanesulphonate	HMDB
{34-hydroxy-40-[(3E)-2-hydroxy-5-methylideneocta-3,7-dien-2-yl]-13,25,27,30,35-pentamethyl-39-methylidene-13-[2-(sulphooxy)ethyl]-4,8,12,17,21,26,32,36,41,45,49-undecaoxaundecacyclo[25.22.0.0³,²⁵.0⁵,²².0⁷,²⁰.0⁹,¹⁸.0¹¹,¹⁶.0³¹,⁴⁸.0³³,⁴⁶.0³⁵,⁴⁴.0³⁷,⁴²]nonatetracontan-14-yl}oxidanesulphonic acid	HMDB

Showing 1 to 4 of 4 entries

Predicted Properties

Property	Value	Source
Water Solubility	0.036 g/L	ALOGPS
logP	0.48	ALOGPS
logP	-0.44	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Acidic)	-2.3	ChemAxon
pKa (Strongest Basic)	-3.4	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	19	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	269.19 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	275.59 m³·mol⁻¹	ChemAxon
Polarizability	121.45 Å³	ChemAxon
Number of Rings	11	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Chemical Formula

C55H82O21S2

IUPAC name

{34-hydroxy-40-[(3E)-2-hydroxy-5-methylideneocta-3,7-dien-2-yl]-13,25,27,30,35-pentamethyl-39-methylidene-13-[2-(sulfooxy)ethyl]-4,8,12,17,21,26,32,36,41,45,49-undecaoxaundecacyclo[25.22.0.0³,²⁵.0⁵,²².0⁷,²⁰.0⁹,¹⁸.0¹¹,¹⁶.0³¹,⁴⁸.0³³,⁴⁶.0³⁵,⁴⁴.0³⁷,⁴²]nonatetracontan-14-yl}oxidanesulfonic acid

InChI Identifier

InChI=1S/C55H82O21S2/c1-10-11-28(2)12-15-51(5,57)50-30(4)20-39-38(71-50)26-46-55(9,74-39)49(56)48-42(70-46)24-41-47(72-48)29(3)13-16-53(7)44(69-41)27-43-54(8,76-53)17-14-31-32(68-43)21-34-33(65-31)22-35-36(66-34)23-40-37(67-35)25-45(75-78(61,62)63)52(6,73-40)18-19-64-77(58,59)60/h10,12,15,29,31-50,56-57H,1-2,4,11,13-14,16-27H2,3,5-9H3,(H,58,59,60)(H,61,62,63)/b15-12+

InChI Key

HCYDZFJGUKMTQB-NTCAYCPXSA-N

Isomeric SMILES

CC1CCC2(C)OC3(C)CCC4OC5CC6OC7CC(OS(O)(=O)=O)C(C)(CCOS(O)(=O)=O)OC7CC6OC5CC4OC3CC2OC2CC3OC4CC5OC(C(=C)CC5OC4(C)C(O)C3OC12)C(C)(O)\C=C\C(=C)CC=C

Average Molecular Weight

1143.357

Monoisotopic Molecular Weight

1142.479001066

Classification

Description

Belongs to the class of organic compounds known as ciguatera toxins. These are lipid-soluble polyether compounds consisting of 13 to 14 rings fused by ether linkages into a most rigid ladder-like structure.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Ciguatera toxins

Sub Class

Not Available

Direct Parent

Ciguatera toxins

Alternative Parents

Substituents

Ciguatera toxin fragment
Oxepane
Monosaccharide
Oxane
Sulfuric acid monoester
Sulfate-ester
Alkyl sulfate
Sulfuric acid ester
Organic sulfuric acid or derivatives
Tertiary alcohol
Secondary alcohol
Dialkyl ether
Ether
Organoheterocyclic compound
Oxacycle
Organic oxygen compound
Organic oxide
Organooxygen compound
Alcohol
Hydrocarbon derivative
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Extracellular

Process

Naturally occurring process:

Biological process:

Cellular process:

Cell signaling

Role

Indirect biological role:

Marine biotoxin

Industrial application:

Biological role:

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

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Property	Value	Reference
Boiling Point	Not Available
Charge	Not Available
Density	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Experimental Water Solubility	Not Available
Isoelectric point	Not Available
Mass Composition	C 57.78%; H 7.23%; O 29.39%; S 5.61%	DFC
Melting Point	Not Available
Optical Rotation	[a]20D +3.01 (c, 0.45 in MeOH)	DFC

Showing 1 to 10 of 14 entries

Spectra

EI-MS/GC-MS

Not Available

MS/MS

Type	Description	Splash Key	View
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004l-7910000020-43d0a8f2e5d9bcd19e3b	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-002b-9300200002-15f8f8f67f419160fb10	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0zir-9312130110-67e4acdc4b7dd91a5ab4	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-2627022911-c31050147bcc2736e969	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-01r2-6714001290-0a311094868f3fe31712	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00m3-0875894320-4ed0a59a80a1aed5645f	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-0900000000-9fdcb2cc2665ea1510de	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0006-3900010000-5dc289d7a6dc488429ae	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-000b-9500110500-46667fd9fb40cbe5e310	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0006-9700000000-8b2ebd3ac62a2aef3c56	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-052f-9300000000-10099228f76be3b0e036	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-016u-9100000100-b7c28ab5f65fc4e8235e	2021-09-24	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

Not Available

ChEMBL ID

Not Available

KEGG Compound ID

Not Available

Pubchem Compound ID

13988278

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB33320

CRC / DFC (Dictionary of Food Compounds) ID

GND03-Q:GND03-Q

EAFUS ID

Not Available

Dr. Duke ID

Not Available

BIGG ID

Not Available

KNApSAcK ID

Not Available

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

Not Available

Wikipedia ID

Not Available

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

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Food	Content Range	Average	Reference

Processing...

Biological Effects and Interactions

Health Effects / Bioactivities

Not Available

Enzymes

Not Available

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Not Available

Files

MSDS

Not Available

References

Synthesis Reference

Not Available

General Reference

Not Available

Content Reference

Showing Compound Yessotoxin (FDB011347)

Structure for FDB011347 (Yessotoxin)