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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:30:18 UTC
Update Date2022-03-07 02:52:09 UTC
HMDB IDHMDB0029417
Secondary Accession Numbers
  • HMDB29417
Metabolite Identification
Common NameCycloalliin
DescriptionCycloalliin belongs to the class of organic compounds known as alpha amino acids. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon). Cycloalliin has been detected, but not quantified in, several different foods, such as green onion, onion-family vegetables, garden onions (Allium cepa), red onion, and garden onion (var.). This could make cycloalliin a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on Cycloalliin.
Structure
Data?1582753415
Synonyms
ValueSource
CycloallinMeSH
3-Methyl-1,4-thiazane-5-carboxylic acid-1-oxideMeSH
5-Methyl-3-thiomorpholinecarboxylic acid 1-oxide, 9ciHMDB
5-Methyl-1-oxo-1λ⁴-thiomorpholine-3-carboxylateGenerator
CycloalliinMeSH
Chemical FormulaC6H11NO3S
Average Molecular Weight177.221
Monoisotopic Molecular Weight177.045963913
IUPAC Name5-methyl-1-oxo-1λ⁴-thiomorpholine-3-carboxylic acid
Traditional Name5-methyl-1-oxo-1λ⁴-thiomorpholine-3-carboxylic acid
CAS Registry Number455-41-4
SMILES
CC1CS(=O)CC(N1)C(O)=O
InChI Identifier
InChI=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
Chemical Taxonomy
Description Belongs to the class of organic compounds known as alpha amino acids. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon).
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentAlpha amino acids
Alternative Parents
Substituents
  • Alpha-amino acid
  • Thiomorpholine-3-carboxylic acid
  • 1,4-thiazinane
  • Sulfoxide
  • Amino acid
  • Carboxylic acid
  • Secondary aliphatic amine
  • Monocarboxylic acid or derivatives
  • Secondary amine
  • Sulfinyl compound
  • Organoheterocyclic compound
  • Azacycle
  • Carbonyl group
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Organic nitrogen compound
  • Amine
  • Hydrocarbon derivative
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot 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 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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+137.99931661259
DarkChem[M-H]-133.23331661259
DeepCCS[M+H]+131.30630932474
DeepCCS[M-H]-127.47530932474
DeepCCS[M-2H]-164.7430932474
DeepCCS[M+Na]+139.99330932474
AllCCS[M+H]+138.132859911
AllCCS[M+H-H2O]+133.932859911
AllCCS[M+NH4]+142.032859911
AllCCS[M+Na]+143.132859911
AllCCS[M-H]-133.332859911
AllCCS[M+Na-2H]-134.832859911
AllCCS[M+HCOO]-136.532859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
CycloalliinCC1CS(=O)CC(N1)C(O)=O3058.4Standard polar33892256
CycloalliinCC1CS(=O)CC(N1)C(O)=O1418.8Standard non polar33892256
CycloalliinCC1CS(=O)CC(N1)C(O)=O1558.1Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Cycloalliin,1TMS,isomer #1CC1CS(=O)CC(C(=O)O[Si](C)(C)C)N11658.9Semi standard non polar33892256
Cycloalliin,1TMS,isomer #2CC1CS(=O)CC(C(=O)O)N1[Si](C)(C)C1700.9Semi standard non polar33892256
Cycloalliin,2TMS,isomer #1CC1CS(=O)CC(C(=O)O[Si](C)(C)C)N1[Si](C)(C)C1713.4Semi standard non polar33892256
Cycloalliin,2TMS,isomer #1CC1CS(=O)CC(C(=O)O[Si](C)(C)C)N1[Si](C)(C)C1789.8Standard non polar33892256
Cycloalliin,1TBDMS,isomer #1CC1CS(=O)CC(C(=O)O[Si](C)(C)C(C)(C)C)N11914.4Semi standard non polar33892256
Cycloalliin,1TBDMS,isomer #2CC1CS(=O)CC(C(=O)O)N1[Si](C)(C)C(C)(C)C2001.4Semi standard non polar33892256
Cycloalliin,2TBDMS,isomer #1CC1CS(=O)CC(C(=O)O[Si](C)(C)C(C)(C)C)N1[Si](C)(C)C(C)(C)C2219.5Semi standard non polar33892256
Cycloalliin,2TBDMS,isomer #1CC1CS(=O)CC(C(=O)O[Si](C)(C)C(C)(C)C)N1[Si](C)(C)C(C)(C)C2341.6Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Cycloalliin GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9300000000-c19fb58b8de9b4610c822017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Cycloalliin GC-MS (1 TMS) - 70eV, Positivesplash10-00el-9300000000-5b90c0be83f8decf8a0b2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Cycloalliin GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Cycloalliin GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Cycloalliin GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-11-03Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Cycloalliin GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-11-03Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Cycloalliin GC-MS (TBDMS_1_2) - 70eV, PositiveNot Available2021-11-03Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cycloalliin 10V, Positive-QTOFsplash10-004i-0900000000-da896183c9bf8df450df2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cycloalliin 20V, Positive-QTOFsplash10-01sl-8900000000-682ada8684b8090f32762016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cycloalliin 40V, Positive-QTOFsplash10-0006-9200000000-1b42ba22c9af8fcd4eb42016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cycloalliin 10V, Negative-QTOFsplash10-01t9-2900000000-fe357d631947ab91f41f2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cycloalliin 20V, Negative-QTOFsplash10-0a4i-9200000000-efc045a11871e7c316e92016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cycloalliin 40V, Negative-QTOFsplash10-0002-9300000000-7515b0068f427240f60f2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cycloalliin 10V, Positive-QTOFsplash10-004i-0900000000-cb152457ebfe3e0f4d462021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cycloalliin 20V, Positive-QTOFsplash10-03n9-4900000000-f23b089a2c4aef2574dd2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cycloalliin 40V, Positive-QTOFsplash10-03kc-9200000000-bdeea7b8047cc9c026622021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cycloalliin 10V, Negative-QTOFsplash10-004i-0900000000-74647462bbc23f49b6352021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cycloalliin 20V, Negative-QTOFsplash10-03di-9500000000-2bb2019b64d2851923a62021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cycloalliin 40V, Negative-QTOFsplash10-03el-9000000000-f4d852c7a488a1d50b372021-09-25Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-16Wishart 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 IDFDB000512
KNApSAcK IDC00055438
Chemspider ID19100864
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound3549960
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.. .