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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:32:36 UTC
Update Date2022-03-07 02:52:17 UTC
HMDB IDHMDB0029781
Secondary Accession Numbers
  • HMDB29781
Metabolite Identification
Common Name54-Deoxyciguatoxin
Description54-Deoxyciguatoxin, also known as ciguatoxin CTX 3 or 52-epiciguatoxin 3, 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. 54-Deoxyciguatoxin is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, 54-deoxyciguatoxin has been detected, but not quantified in, fishes. This could make 54-deoxyciguatoxin a potential biomarker for the consumption of these foods.
Structure
Data?1582753463
Synonyms
ValueSource
52-Epiciguatoxin 3HMDB
Ciguatoxin CTX 3HMDB
CTX 3HMDB
p-CTX 3HMDB
Pacific ciguatoxin 3HMDB
Chemical FormulaC60H86O18
Average Molecular Weight1095.314
Monoisotopic Molecular Weight1094.581415948
IUPAC Name(29Z)-16-[(1Z)-3,4-dihydroxybut-1-en-1-yl]-43,44,49,54,58-pentamethyl-2,7,11,17,21,26,33,37,41,46,51,57-dodecaoxaspiro[dodecacyclo[30.28.0.0³,²⁷.0⁶,²⁵.0⁸,²².0¹⁰,²⁰.0¹²,¹⁸.0³⁴,⁵⁸.0³⁶,⁵⁶.0³⁸,⁵².0⁴⁰,⁵⁰.0⁴²,⁴⁷]hexacontane-45,2'-oxolane]-4,14,23,29-tetraene-19,48,59-triol
Traditional Name(29Z)-16-[(1Z)-3,4-dihydroxybut-1-en-1-yl]-43,44,49,54,58-pentamethyl-2,7,11,17,21,26,33,37,41,46,51,57-dodecaoxaspiro[dodecacyclo[30.28.0.0³,²⁷.0⁶,²⁵.0⁸,²².0¹⁰,²⁰.0¹²,¹⁸.0³⁴,⁵⁸.0³⁶,⁵⁶.0³⁸,⁵².0⁴⁰,⁵⁰.0⁴²,⁴⁷]hexacontane-45,2'-oxolane]-4,14,23,29-tetraene-19,48,59-triol
CAS Registry Number139341-09-6
SMILES
CC1C(C)C2(CCCO2)OC2C1OC1CC3OC4CC5OC6C\C=C/CC7OC8C=CC9OC%10C(CC9OC8C=CC7OC6CC(O)C5(C)OC4CC(C)CC3OC1C(C)C2O)OC1CC=CC(OC1C%10O)\C=C/C(O)CO
InChI Identifier
InChI=1S/C60H86O18/c1-29-22-42-44(25-48-54(75-42)31(3)52(64)58-55(76-48)30(2)32(4)60(78-58)20-9-21-66-60)72-46-27-51-59(5,77-47(46)23-29)50(63)26-45-36(73-51)12-7-6-11-35-37(70-45)16-17-39-38(68-35)18-19-40-43(69-39)24-49-57(74-40)53(65)56-41(71-49)13-8-10-34(67-56)15-14-33(62)28-61/h6-8,10,14-19,29-58,61-65H,9,11-13,20-28H2,1-5H3/b7-6-,15-14-
InChI KeyRWSYPPRKMNWNII-HXDWTSBLSA-N
Chemical Taxonomy
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.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassCiguatera toxins
Sub ClassNot Available
Direct ParentCiguatera toxins
Alternative Parents
Substituents
  • Ciguatera toxin fragment
  • Ketal
  • Oxepane
  • Monosaccharide
  • Oxane
  • Tetrahydrofuran
  • Secondary alcohol
  • Polyol
  • Organoheterocyclic compound
  • Oxacycle
  • Ether
  • Dialkyl ether
  • Acetal
  • Primary alcohol
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Alcohol
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Not AvailableNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.011 g/LALOGPS
logP2.38ALOGPS
logP3.47ChemAxon
logS-5ALOGPS
pKa (Strongest Acidic)12.88ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count18ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area221.14 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity283.37 m³·mol⁻¹ChemAxon
Polarizability119.99 ųChemAxon
Number of Rings13ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
AllCCS[M+H]+310.932859911
AllCCS[M+H-H2O]+310.632859911
AllCCS[M+NH4]+311.332859911
AllCCS[M+Na]+311.432859911
AllCCS[M-H]-253.432859911
AllCCS[M+Na-2H]-258.632859911
AllCCS[M+HCOO]-264.232859911

Predicted Kovats Retention Indices

Not Available
Spectra

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 54-Deoxyciguatoxin 10V, Positive-QTOFsplash10-056s-9000000000-ec8c7c96b66ebb9e84102017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 54-Deoxyciguatoxin 20V, Positive-QTOFsplash10-0aor-9100020012-dff49f08b0ce1298cc3b2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 54-Deoxyciguatoxin 40V, Positive-QTOFsplash10-052r-9000000100-3906f5414255bb05cc482017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 54-Deoxyciguatoxin 10V, Negative-QTOFsplash10-0006-9200000021-dbdd7ba95dd6b8217de32017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 54-Deoxyciguatoxin 20V, Negative-QTOFsplash10-0udl-6092004032-4a7b01f397ede554c5a02017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 54-Deoxyciguatoxin 40V, Negative-QTOFsplash10-00dr-4697371110-07e54fca633a1a496c402017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 54-Deoxyciguatoxin 10V, Positive-QTOFsplash10-002b-9000000000-f2a630b42db8798edee02021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 54-Deoxyciguatoxin 20V, Positive-QTOFsplash10-004j-9100000000-f85c7b21ff23bfa66a222021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 54-Deoxyciguatoxin 40V, Positive-QTOFsplash10-00c1-9600000002-160fa68e795161e8550b2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 54-Deoxyciguatoxin 10V, Negative-QTOFsplash10-0006-9000000000-dc2f9613a0ce5a7d6aa42021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 54-Deoxyciguatoxin 20V, Negative-QTOFsplash10-0006-9000000000-5a527d2975e8d2722e2d2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 54-Deoxyciguatoxin 40V, Negative-QTOFsplash10-004i-9200012042-1e6acb92f7e52b31ca392021-09-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB000988
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound131750902
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .