Showing Compound Carboxyhomoyessotoxin (FDB019823)

Record Information

Version

1.0

Creation date

2010-04-08 22:14:36 UTC

Update date

2019-11-26 03:17:54 UTC

Primary ID

FDB019823

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Carboxyhomoyessotoxin

Description

Carboxyhomoyessotoxin 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. Carboxyhomoyessotoxin has been detected, but not quantified in, mollusks. This could make carboxyhomoyessotoxin a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Carboxyhomoyessotoxin.

CAS Number

292850-13-6

Structure

MOL SDF PDB SMILES InChI

Synonyms

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Synonym	Source
(3E)-5-Hydroxy-5-[34-hydroxy-13,25,27,30,35-pentamethyl-39-methylidene-14-(sulfooxy)-13-[3-(sulfooxy)propyl]-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-40-yl]-2-(prop-2-en-1-yl)hex-3-enoate	HMDB
(3E)-5-Hydroxy-5-[34-hydroxy-13,25,27,30,35-pentamethyl-39-methylidene-14-(sulphooxy)-13-[3-(sulphooxy)propyl]-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-40-yl]-2-(prop-2-en-1-yl)hex-3-enoate	HMDB
(3E)-5-Hydroxy-5-[34-hydroxy-13,25,27,30,35-pentamethyl-39-methylidene-14-(sulphooxy)-13-[3-(sulphooxy)propyl]-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-40-yl]-2-(prop-2-en-1-yl)hex-3-enoic acid	HMDB
Carboxyhomoyessotoxin	MeSH

Showing 1 to 4 of 4 entries

Predicted Properties

Property	Value	Source
Water Solubility	0.043 g/L	ALOGPS
logP	0.4	ALOGPS
logP	-0.57	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Acidic)	-2.3	ChemAxon
pKa (Strongest Basic)	-3.4	ChemAxon
Physiological Charge	-3	ChemAxon
Hydrogen Acceptor Count	21	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	306.49 Å²	ChemAxon
Rotatable Bond Count	13	ChemAxon
Refractivity	282.15 m³·mol⁻¹	ChemAxon
Polarizability	125.1 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

C56H84O23S2

IUPAC name

(3E)-5-hydroxy-5-[34-hydroxy-13,25,27,30,35-pentamethyl-39-methylidene-14-(sulfooxy)-13-[3-(sulfooxy)propyl]-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-40-yl]-2-(prop-2-en-1-yl)hex-3-enoic acid

InChI Identifier

InChI=1S/C56H84O23S2/c1-9-11-30(51(58)59)13-16-52(4,60)50-29(3)20-39-38(74-50)26-46-56(8,77-39)49(57)48-42(73-46)24-41-47(75-48)28(2)12-17-54(6)44(72-41)27-43-55(7,79-54)18-14-31-32(71-43)21-34-33(68-31)22-35-36(69-34)23-40-37(70-35)25-45(78-81(64,65)66)53(5,76-40)15-10-19-67-80(61,62)63/h9,13,16,28,30-50,57,60H,1,3,10-12,14-15,17-27H2,2,4-8H3,(H,58,59)(H,61,62,63)(H,64,65,66)/b16-13+

InChI Key

NWJHPOGGOSFSPA-DTQAZKPQSA-N

Isomeric SMILES

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

Average Molecular Weight

1189.382

Monoisotopic Molecular Weight

1188.484480374

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
Sulfated fatty acid
Medium-chain fatty acid
Branched fatty acid
Heterocyclic fatty acid
Hydroxy fatty acid
Oxepane
Monosaccharide
Oxane
Fatty acyl
Fatty acid
Sulfuric acid monoester
Sulfate-ester
Unsaturated fatty acid
Alkyl sulfate
Sulfuric acid ester
Tertiary alcohol
Organic sulfuric acid or derivatives
Secondary alcohol
Monocarboxylic acid or derivatives
Oxacycle
Ether
Carboxylic acid derivative
Carboxylic acid
Organoheterocyclic compound
Dialkyl ether
Alcohol
Hydrocarbon derivative
Carbonyl group
Organic oxygen compound
Organic oxide
Organooxygen compound
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

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 56.55%; H 7.12%; O 30.94%; S 5.39%	DFC
Melting Point	Not Available
Optical Rotation	Not Available

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	splash10-00di-3900000000-b3ba1c7c1d163123cff4	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0006-9300010001-5f91ba99647528fea7c4	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-014i-9200020001-c176c7a8962d51e3bf78	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-052r-0938020281-30efb0c65d4e88b6afea	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0bvi-3902401053-fd086786b6088d9012cb	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0159-0351492211-d824942563379c1fd898	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-009i-4900000000-ecf562625aca27c3e6dc	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00n0-9500000001-49e8f1b46c88af87283a	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000x-9100000000-7eb676b006b3af215cde	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0900000000-d1422100cdd55974513b	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000j-4900000000-f98bb6ccf7f00879f080	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0012-9600000300-fb1153e062f3d29af5d4	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

Not Available

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB40130

CRC / DFC (Dictionary of Food Compounds) ID

GND03-Q:MCV75-O

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

No data available in table

Showing 0 to 0 of 0 entries

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 Carboxyhomoyessotoxin (FDB019823)

Structure for FDB019823 (Carboxyhomoyessotoxin)