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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2021-09-11 00:09:32 UTC
Update Date2021-09-26 22:56:38 UTC
HMDB IDHMDB0247146
Secondary Accession NumbersNone
Metabolite Identification
Common Name2,3,4-Tri-O-acetylarabinopyranosyl isothiocyanate
Description2,3,4-Tri-O-acetylarabinopyranosyl isothiocyanate belongs to the class of organic compounds known as glycosylamines. Glycosylamines are compounds consisting of an amine with a beta-N-glycosidic bond to a carbohydrate, thus forming a cyclic hemiaminal ether bond (alpha-amino ether). Based on a literature review very few articles have been published on 2,3,4-Tri-O-acetylarabinopyranosyl isothiocyanate. This compound has been identified in human blood as reported by (PMID: 31557052 ). 2,3,4-tri-o-acetylarabinopyranosyl isothiocyanate is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically 2,3,4-Tri-O-acetylarabinopyranosyl isothiocyanate is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.
Structure
Thumb
Synonyms
ValueSource
2,3,4-Tri-O-acetylarabinopyranosyl isothiocyanic acidGenerator
Chemical FormulaC12H15NO7S
Average Molecular Weight317.31
Monoisotopic Molecular Weight317.056923001
IUPAC Name4,5-bis(acetyloxy)-2-isothiocyanatooxan-3-yl acetate
Traditional Name4,5-bis(acetyloxy)-2-isothiocyanatooxan-3-yl acetate
CAS Registry NumberNot Available
SMILES
CC(=O)OC1COC(N=C=S)C(OC(C)=O)C1OC(C)=O
InChI Identifier
InChI=1S/C12H15NO7S/c1-6(14)18-9-4-17-12(13-5-21)11(20-8(3)16)10(9)19-7(2)15/h9-12H,4H2,1-3H3
InChI KeyRCHZRAFPHKCWRI-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as glycosylamines. Glycosylamines are compounds consisting of an amine with a beta-N-glycosidic bond to a carbohydrate, thus forming a cyclic hemiaminal ether bond (alpha-amino ether).
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentGlycosylamines
Alternative Parents
Substituents
  • N-glycosyl compound
  • Tricarboxylic acid or derivatives
  • Oxane
  • Isothiocyanate
  • Carboxylic acid ester
  • Oxacycle
  • Organoheterocyclic compound
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Carboxylic acid derivative
  • Organic oxide
  • Hydrocarbon derivative
  • Organosulfur compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Carbonyl group
  • Organopnictogen compound
  • 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
logP1.45ALOGPS
logP0.61ChemAxon
logS-3ALOGPS
pKa (Strongest Acidic)15.06ChemAxon
pKa (Strongest Basic)-4.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area100.49 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity70.48 m³·mol⁻¹ChemAxon
Polarizability30.05 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+161.68330932474
DeepCCS[M-H]-159.32530932474
DeepCCS[M-2H]-192.38630932474
DeepCCS[M+Na]+167.77630932474
AllCCS[M+H]+169.132859911
AllCCS[M+H-H2O]+166.032859911
AllCCS[M+NH4]+171.932859911
AllCCS[M+Na]+172.732859911
AllCCS[M-H]-168.832859911
AllCCS[M+Na-2H]-169.132859911
AllCCS[M+HCOO]-169.632859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
2,3,4-Tri-O-acetylarabinopyranosyl isothiocyanateCC(=O)OC1COC(N=C=S)C(OC(C)=O)C1OC(C)=O3445.9Standard polar33892256
2,3,4-Tri-O-acetylarabinopyranosyl isothiocyanateCC(=O)OC1COC(N=C=S)C(OC(C)=O)C1OC(C)=O1993.7Standard non polar33892256
2,3,4-Tri-O-acetylarabinopyranosyl isothiocyanateCC(=O)OC1COC(N=C=S)C(OC(C)=O)C1OC(C)=O1935.8Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 2,3,4-Tri-O-acetylarabinopyranosyl isothiocyanate GC-MS (Non-derivatized) - 70eV, Positivesplash10-0aov-5490000000-0bafe2592a3b4e5da3372021-09-24Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2,3,4-Tri-O-acetylarabinopyranosyl isothiocyanate 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 - 2,3,4-Tri-O-acetylarabinopyranosyl isothiocyanate 10V, Positive-QTOFsplash10-014i-0039000000-3bdb586ad93b540b6eee2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,3,4-Tri-O-acetylarabinopyranosyl isothiocyanate 20V, Positive-QTOFsplash10-014i-0249000000-005a7499e3243c6042b62021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,3,4-Tri-O-acetylarabinopyranosyl isothiocyanate 40V, Positive-QTOFsplash10-01p2-9430000000-0308d5a43e28d50ae1bb2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,3,4-Tri-O-acetylarabinopyranosyl isothiocyanate 10V, Negative-QTOFsplash10-014i-0096000000-7fb9810901657122e7342021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,3,4-Tri-O-acetylarabinopyranosyl isothiocyanate 20V, Negative-QTOFsplash10-0a4i-9341000000-0680aa31397330427ce22021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,3,4-Tri-O-acetylarabinopyranosyl isothiocyanate 40V, Negative-QTOFsplash10-0bu0-9180000000-63e8646a348670246d022021-10-12Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected 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 IDNot Available
KNApSAcK IDNot Available
Chemspider ID3108815
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound3884507
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. Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]