Hmdb loader
Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2012-09-11 18:38:20 UTC
Update Date2022-09-22 18:34:58 UTC
HMDB IDHMDB0033865
Secondary Accession Numbers
  • HMDB33865
Metabolite Identification
Common NameLotaustralin
DescriptionLotaustralin belongs to the class of organic compounds known as cyanogenic glycosides. These are glycosides in which the aglycone moiety contains a cyanide group. Lotaustralin has been detected, but not quantified in, several different foods, such as pili nuts (Canarium ovatum), corn salads (Valerianella locusta), carrots (Daucus carota ssp. sativus), acorns (Quercus), and carobs (Ceratonia siliqua). This could make lotaustralin a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Lotaustralin.
Structure
Data?1563862472
Synonyms
ValueSource
2(R)-Hydroxy-2-methylbutyronitrile-beta-D-glucopyranosideHMDB
2-(beta-D-Glucopyranosyloxy)-2-methyl-(R)-butanenitrileHMDB
2(R)-Hydroxy-2-methylbutyronitrile-beta-D- glucopyranosideMeSH
Lotaustralin, (S)-isomerMeSH
Chemical FormulaC11H19NO6
Average Molecular Weight261.2717
Monoisotopic Molecular Weight261.121237345
IUPAC Name2-methyl-2-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}butanenitrile
Traditional Name2-methyl-2-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}butanenitrile
CAS Registry Number534-67-8
SMILES
CCC(C)(OC1OC(CO)C(O)C(O)C1O)C#N
InChI Identifier
InChI=1S/C11H19NO6/c1-3-11(2,5-12)18-10-9(16)8(15)7(14)6(4-13)17-10/h6-10,13-16H,3-4H2,1-2H3
InChI KeyWEWBWVMTOYUPHH-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as cyanogenic glycosides. These are glycosides in which the aglycone moiety contains a cyanide group.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentCyanogenic glycosides
Alternative Parents
Substituents
  • Cyanogenic glycoside
  • Hexose monosaccharide
  • O-glycosyl compound
  • Monosaccharide
  • Oxane
  • Secondary alcohol
  • Polyol
  • Organoheterocyclic compound
  • Oxacycle
  • Nitrile
  • Carbonitrile
  • Acetal
  • Primary alcohol
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Organic nitrogen compound
  • Alcohol
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Biological locationRoute of exposureSource
ProcessNot Available
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point139 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility62.3 g/LALOGPS
logP-0.88ALOGPS
logP-1.2ChemAxon
logS-0.62ALOGPS
pKa (Strongest Acidic)12.21ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area123.17 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity59.47 m³·mol⁻¹ChemAxon
Polarizability25.89 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]+161.49731661259
DarkChem[M-H]-155.78531661259
DeepCCS[M+H]+162.16530932474
DeepCCS[M-H]-159.80830932474
DeepCCS[M-2H]-193.32830932474
DeepCCS[M+Na]+168.77730932474
AllCCS[M+H]+160.932859911
AllCCS[M+H-H2O]+157.532859911
AllCCS[M+NH4]+164.132859911
AllCCS[M+Na]+165.032859911
AllCCS[M-H]-159.032859911
AllCCS[M+Na-2H]-159.332859911
AllCCS[M+HCOO]-159.832859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
LotaustralinCCC(C)(OC1OC(CO)C(O)C(O)C1O)C#N2345.0Standard polar33892256
LotaustralinCCC(C)(OC1OC(CO)C(O)C(O)C1O)C#N2087.8Standard non polar33892256
LotaustralinCCC(C)(OC1OC(CO)C(O)C(O)C1O)C#N2093.3Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Lotaustralin,1TMS,isomer #1CCC(C)(C#N)OC1OC(CO[Si](C)(C)C)C(O)C(O)C1O2124.5Semi standard non polar33892256
Lotaustralin,1TMS,isomer #2CCC(C)(C#N)OC1OC(CO)C(O[Si](C)(C)C)C(O)C1O2088.4Semi standard non polar33892256
Lotaustralin,1TMS,isomer #3CCC(C)(C#N)OC1OC(CO)C(O)C(O[Si](C)(C)C)C1O2087.8Semi standard non polar33892256
Lotaustralin,1TMS,isomer #4CCC(C)(C#N)OC1OC(CO)C(O)C(O)C1O[Si](C)(C)C2095.6Semi standard non polar33892256
Lotaustralin,2TMS,isomer #1CCC(C)(C#N)OC1OC(CO[Si](C)(C)C)C(O[Si](C)(C)C)C(O)C1O2136.0Semi standard non polar33892256
Lotaustralin,2TMS,isomer #2CCC(C)(C#N)OC1OC(CO[Si](C)(C)C)C(O)C(O[Si](C)(C)C)C1O2140.4Semi standard non polar33892256
Lotaustralin,2TMS,isomer #3CCC(C)(C#N)OC1OC(CO[Si](C)(C)C)C(O)C(O)C1O[Si](C)(C)C2133.5Semi standard non polar33892256
Lotaustralin,2TMS,isomer #4CCC(C)(C#N)OC1OC(CO)C(O[Si](C)(C)C)C(O[Si](C)(C)C)C1O2110.3Semi standard non polar33892256
Lotaustralin,2TMS,isomer #5CCC(C)(C#N)OC1OC(CO)C(O[Si](C)(C)C)C(O)C1O[Si](C)(C)C2117.2Semi standard non polar33892256
Lotaustralin,2TMS,isomer #6CCC(C)(C#N)OC1OC(CO)C(O)C(O[Si](C)(C)C)C1O[Si](C)(C)C2121.6Semi standard non polar33892256
Lotaustralin,3TMS,isomer #1CCC(C)(C#N)OC1OC(CO[Si](C)(C)C)C(O[Si](C)(C)C)C(O[Si](C)(C)C)C1O2123.3Semi standard non polar33892256
Lotaustralin,3TMS,isomer #2CCC(C)(C#N)OC1OC(CO[Si](C)(C)C)C(O[Si](C)(C)C)C(O)C1O[Si](C)(C)C2122.1Semi standard non polar33892256
Lotaustralin,3TMS,isomer #3CCC(C)(C#N)OC1OC(CO[Si](C)(C)C)C(O)C(O[Si](C)(C)C)C1O[Si](C)(C)C2119.2Semi standard non polar33892256
Lotaustralin,3TMS,isomer #4CCC(C)(C#N)OC1OC(CO)C(O[Si](C)(C)C)C(O[Si](C)(C)C)C1O[Si](C)(C)C2112.3Semi standard non polar33892256
Lotaustralin,4TMS,isomer #1CCC(C)(C#N)OC1OC(CO[Si](C)(C)C)C(O[Si](C)(C)C)C(O[Si](C)(C)C)C1O[Si](C)(C)C2102.1Semi standard non polar33892256
Lotaustralin,1TBDMS,isomer #1CCC(C)(C#N)OC1OC(CO[Si](C)(C)C(C)(C)C)C(O)C(O)C1O2349.6Semi standard non polar33892256
Lotaustralin,1TBDMS,isomer #2CCC(C)(C#N)OC1OC(CO)C(O[Si](C)(C)C(C)(C)C)C(O)C1O2317.2Semi standard non polar33892256
Lotaustralin,1TBDMS,isomer #3CCC(C)(C#N)OC1OC(CO)C(O)C(O[Si](C)(C)C(C)(C)C)C1O2318.6Semi standard non polar33892256
Lotaustralin,1TBDMS,isomer #4CCC(C)(C#N)OC1OC(CO)C(O)C(O)C1O[Si](C)(C)C(C)(C)C2329.1Semi standard non polar33892256
Lotaustralin,2TBDMS,isomer #1CCC(C)(C#N)OC1OC(CO[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C(O)C1O2565.5Semi standard non polar33892256
Lotaustralin,2TBDMS,isomer #2CCC(C)(C#N)OC1OC(CO[Si](C)(C)C(C)(C)C)C(O)C(O[Si](C)(C)C(C)(C)C)C1O2565.2Semi standard non polar33892256
Lotaustralin,2TBDMS,isomer #3CCC(C)(C#N)OC1OC(CO[Si](C)(C)C(C)(C)C)C(O)C(O)C1O[Si](C)(C)C(C)(C)C2567.1Semi standard non polar33892256
Lotaustralin,2TBDMS,isomer #4CCC(C)(C#N)OC1OC(CO)C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C1O2548.7Semi standard non polar33892256
Lotaustralin,2TBDMS,isomer #5CCC(C)(C#N)OC1OC(CO)C(O[Si](C)(C)C(C)(C)C)C(O)C1O[Si](C)(C)C(C)(C)C2551.2Semi standard non polar33892256
Lotaustralin,2TBDMS,isomer #6CCC(C)(C#N)OC1OC(CO)C(O)C(O[Si](C)(C)C(C)(C)C)C1O[Si](C)(C)C(C)(C)C2558.0Semi standard non polar33892256
Lotaustralin,3TBDMS,isomer #1CCC(C)(C#N)OC1OC(CO[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C1O2757.4Semi standard non polar33892256
Lotaustralin,3TBDMS,isomer #2CCC(C)(C#N)OC1OC(CO[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C(O)C1O[Si](C)(C)C(C)(C)C2759.2Semi standard non polar33892256
Lotaustralin,3TBDMS,isomer #3CCC(C)(C#N)OC1OC(CO[Si](C)(C)C(C)(C)C)C(O)C(O[Si](C)(C)C(C)(C)C)C1O[Si](C)(C)C(C)(C)C2757.9Semi standard non polar33892256
Lotaustralin,3TBDMS,isomer #4CCC(C)(C#N)OC1OC(CO)C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C1O[Si](C)(C)C(C)(C)C2738.2Semi standard non polar33892256
Lotaustralin,4TBDMS,isomer #1CCC(C)(C#N)OC1OC(CO[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C1O[Si](C)(C)C(C)(C)C2920.5Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Lotaustralin GC-MS (Non-derivatized) - 70eV, Positivesplash10-0fef-8790000000-d454286498bdc1d9e13f2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Lotaustralin GC-MS (4 TMS) - 70eV, Positivesplash10-001r-4001590000-5e0039f60e7278697d852017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Lotaustralin GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Lotaustralin GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lotaustralin 10V, Positive-QTOFsplash10-0w30-7980000000-3a978648b67dd80be4fb2015-05-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lotaustralin 20V, Positive-QTOFsplash10-0f89-9500000000-3e356cb2d2384f50f2ef2015-05-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lotaustralin 40V, Positive-QTOFsplash10-001i-9200000000-afb8c395ff62b7b822502015-05-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lotaustralin 10V, Negative-QTOFsplash10-03dj-9370000000-ada45f93e850699107ba2015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lotaustralin 20V, Negative-QTOFsplash10-0002-9210000000-8466a5626668275341b02015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lotaustralin 40V, Negative-QTOFsplash10-00sj-9000000000-0527104530bbf9ac9fd42015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lotaustralin 10V, Positive-QTOFsplash10-03di-2190000000-a92ee2fbaaa09afe368f2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lotaustralin 20V, Positive-QTOFsplash10-0a59-9100000000-3039433a4bbd413b84812021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lotaustralin 40V, Positive-QTOFsplash10-001i-9100000000-9382edde2cf9fde3c1732021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lotaustralin 10V, Negative-QTOFsplash10-03di-0090000000-a1ae1ea792d89a4c19742021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lotaustralin 20V, Negative-QTOFsplash10-03di-5950000000-1d766a073aad7b5c983d2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lotaustralin 40V, Negative-QTOFsplash10-05ai-9000000000-c6f23f2a0abdfb4311b82021-09-22Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal details
UrineDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB012049
KNApSAcK IDC00001448
Chemspider ID3817241
KEGG Compound IDC08334
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkLotaustralin
METLIN IDNot Available
PubChem Compound4626626
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.. .

Enzymes

General function:
Involved in hydrolase activity, hydrolyzing O-glycosyl compounds
Specific function:
Glycosidase probably involved in the intestinal absorption and metabolism of dietary flavonoid glycosides. Able to hydrolyze a broad variety of glycosides including phytoestrogens, flavonols, flavones, flavanones and cyanogens. Possesses beta-glycosylceramidase activity and may be involved in a nonlysosomal catabolic pathway of glycosylceramide.
Gene Name:
GBA3
Uniprot ID:
Q9H227
Molecular weight:
Not Available
Reactions
Lotaustralin + Water → (2R)-2-Hydroxy-2-methylbutanenitrile + D-Glucosedetails