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Showing Compound Cycloalliin (FDB000512)

Record Information
Version1.0
Creation date2010-04-08 22:04:36 UTC
Update date2020-02-24 19:10:08 UTC
Primary IDFDB000512
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameCycloalliin
Description2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-6,8-bis[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-4H-chromen-4-one belongs to the class of organic compounds known as flavonoid 8-c-glycosides. Flavonoid 8-C-glycosides are compounds containing a carbohydrate moiety which is C-glycosidically linked to 8-position of a 2-phenylchromen-4-one flavonoid backbone. 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-6,8-bis[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-4H-chromen-4-one is an extremely weak basic (essentially neutral) compound (based on its pKa). 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-6,8-bis[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-4H-chromen-4-one has been detected, but not quantified in, flaxseeds. This could make 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-6,8-bis[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-4H-chromen-4-one a potential biomarker for the consumption of these foods.
CAS Number455-41-4
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
3-Methyl-1,4-thiazane-5-carboxylic acid-1-oxideHMDB
5-Methyl-3-thiomorpholinecarboxylic acid 1-oxide, 9ciHMDB
CycloallinHMDB
5-Methyl-1-oxo-1λ⁴-thiomorpholine-3-carboxylateGenerator
CycloalliinMeSH
5-Methyl-3-thiomorpholinecarboxylic acid 1-oxide, 9CIdb_source
Predicted Properties
PropertyValueSource
Water Solubility52.3 g/LALOGPS
logP-1.9ALOGPS
logP-4ChemAxon
logS-0.53ALOGPS
pKa (Strongest Acidic)1.26ChemAxon
pKa (Strongest Basic)7.79ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area66.4 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity41.89 m³·mol⁻¹ChemAxon
Polarizability17.07 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC6H11NO3S
IUPAC name5-methyl-1-oxo-1λ⁴-thiomorpholine-3-carboxylic acid
InChI IdentifierInChI=1S/C6H11NO3S/c1-4-2-11(10)3-5(7-4)6(8)9/h4-5,7H,2-3H2,1H3,(H,8,9)
InChI KeyJYMHODZXTIGVPA-UHFFFAOYSA-N
Isomeric SMILESCC1CS(=O)CC(N1)C(O)=O
Average Molecular Weight177.221
Monoisotopic Molecular Weight177.045963913
Classification
Description Belongs to the class of organic compounds known as flavonoid 8-c-glycosides. Flavonoid 8-C-glycosides are compounds containing a carbohydrate moiety which is C-glycosidically linked to 8-position of a 2-phenylchromen-4-one flavonoid backbone.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassFlavonoid glycosides
Direct ParentFlavonoid 8-C-glycosides
Alternative Parents
Substituents
  • Flavonoid-8-c-glycoside
  • Hydroxyflavonoid
  • 3'-hydroxyflavonoid
  • 4'-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • 7-hydroxyflavonoid
  • Flavone
  • Phenolic glycoside
  • Hexose monosaccharide
  • Glycosyl compound
  • C-glycosyl compound
  • Chromone
  • 1-benzopyran
  • Benzopyran
  • Catechol
  • Phenol
  • Pyranone
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Monocyclic benzene moiety
  • Benzenoid
  • Pyran
  • Monosaccharide
  • Oxane
  • Vinylogous acid
  • Heteroaromatic compound
  • Secondary alcohol
  • Ether
  • Dialkyl ether
  • Organoheterocyclic compound
  • Oxacycle
  • Polyol
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Primary alcohol
  • Organooxygen compound
  • Alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 40.66%; H 6.26%; N 7.90%; O 27.08%; S 18.09%DFC
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]20D -17.4 (H2O)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-0006-9300000000-c19fb58b8de9b4610c82Spectrum
Predicted GC-MSCycloalliin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0006-9300000000-c19fb58b8de9b4610c82Spectrum
Predicted GC-MSCycloalliin, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00el-9300000000-5b90c0be83f8decf8a0bSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0900000000-da896183c9bf8df450dfSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01sl-8900000000-682ada8684b8090f3276Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9200000000-1b42ba22c9af8fcd4eb4Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-01t9-2900000000-fe357d631947ab91f41fSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-9200000000-efc045a11871e7c316e9Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0002-9300000000-7515b0068f427240f60fSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0900000000-cb152457ebfe3e0f4d46Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03n9-4900000000-f23b089a2c4aef2574ddSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03kc-9200000000-bdeea7b8047cc9c02662Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0900000000-74647462bbc23f49b635Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-9500000000-2bb2019b64d2851923a6Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03el-9000000000-f4d852c7a488a1d50b37Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
ChemSpider ID19100864
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID12305351
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB29417
CRC / DFC (Dictionary of Food Compounds) IDBDB27-V:BDB27-V
EAFUS IDNot Available
Dr. Duke IDCYCLOALLIIN
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
anti aggregantDUKE
fibrinolyticDUKE
lachrymatoryDUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).