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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2021-09-11 12:50:06 UTC
Update Date2021-09-26 23:07:31 UTC
HMDB IDHMDB0253931
Secondary Accession NumbersNone
Metabolite Identification
Common Name[(3S,3Ar,6R,6aS)-6-nitrooxy-2,3,3a,5,6,6a-hexahydrofuro[3,2-b]furan-3-yl] 2-ethylsulfanyl-1,2-dihydropyridine-3-carboxylate
Description6-(nitrooxy)-hexahydrofuro[3,2-b]furan-3-yl 2-(ethylsulfanyl)-1,2-dihydropyridine-3-carboxylate belongs to the class of organic compounds known as isosorbides. These are organic polycyclic compounds containing an isosorbide(1,4-Dianhydrosorbitol) moiety, which consists of two -oxolan-3-ol rings. Based on a literature review very few articles have been published on 6-(nitrooxy)-hexahydrofuro[3,2-b]furan-3-yl 2-(ethylsulfanyl)-1,2-dihydropyridine-3-carboxylate. This compound has been identified in human blood as reported by (PMID: 31557052 ). [(3s,3ar,6r,6as)-6-nitrooxy-2,3,3a,5,6,6a-hexahydrofuro[3,2-b]furan-3-yl] 2-ethylsulfanyl-1,2-dihydropyridine-3-carboxylate is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically [(3S,3Ar,6R,6aS)-6-nitrooxy-2,3,3a,5,6,6a-hexahydrofuro[3,2-b]furan-3-yl] 2-ethylsulfanyl-1,2-dihydropyridine-3-carboxylate 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
6-(Nitrooxy)-hexahydrofuro[3,2-b]furan-3-yl 2-(ethylsulfanyl)-1,2-dihydropyridine-3-carboxylic acidGenerator
6-(Nitrooxy)-hexahydrofuro[3,2-b]furan-3-yl 2-(ethylsulphanyl)-1,2-dihydropyridine-3-carboxylateGenerator
6-(Nitrooxy)-hexahydrofuro[3,2-b]furan-3-yl 2-(ethylsulphanyl)-1,2-dihydropyridine-3-carboxylic acidGenerator
[(3S,3Ar,6R,6as)-6-nitrooxy-2,3,3a,5,6,6a-hexahydrofuro[3,2-b]furan-3-yl] 2-ethylsulfanyl-1,2-dihydropyridine-3-carboxylic acidGenerator
[(3S,3Ar,6R,6as)-6-nitrooxy-2,3,3a,5,6,6a-hexahydrofuro[3,2-b]furan-3-yl] 2-ethylsulphanyl-1,2-dihydropyridine-3-carboxylateGenerator
[(3S,3Ar,6R,6as)-6-nitrooxy-2,3,3a,5,6,6a-hexahydrofuro[3,2-b]furan-3-yl] 2-ethylsulphanyl-1,2-dihydropyridine-3-carboxylic acidGenerator
Chemical FormulaC14H18N2O7S
Average Molecular Weight358.37
Monoisotopic Molecular Weight358.083472102
IUPAC Name6-(nitrooxy)-hexahydrofuro[3,2-b]furan-3-yl 2-(ethylsulfanyl)-1,2-dihydropyridine-3-carboxylate
Traditional Name6-(nitrooxy)-hexahydrofuro[3,2-b]furan-3-yl 2-(ethylsulfanyl)-1,2-dihydropyridine-3-carboxylate
CAS Registry NumberNot Available
SMILES
CCSC1NC=CC=C1C(=O)OC1COC2C(COC12)O[N+]([O-])=O
InChI Identifier
InChI=1S/C14H18N2O7S/c1-2-24-13-8(4-3-5-15-13)14(17)22-9-6-20-12-10(23-16(18)19)7-21-11(9)12/h3-5,9-13,15H,2,6-7H2,1H3
InChI KeyISKSFVDWBALXEP-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as isosorbides. These are organic polycyclic compounds containing an isosorbide(1,4-Dianhydrosorbitol) moiety, which consists of two -oxolan-3-ol rings.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassFurofurans
Sub ClassIsosorbides
Direct ParentIsosorbides
Alternative Parents
Substituents
  • Isosorbide
  • Dihydropyridinecarboxylic acid derivative
  • Dihydropyridine
  • Hydropyridine
  • Organic nitrate
  • Alkyl nitrate
  • Oxolane
  • Enoate ester
  • Alpha,beta-unsaturated carboxylic ester
  • Carboxylic acid ester
  • Organic nitro compound
  • Organic nitric acid or derivatives
  • Carboxylic acid derivative
  • Dialkyl ether
  • Ether
  • Oxacycle
  • Monocarboxylic acid or derivatives
  • Azacycle
  • Dialkylthioether
  • Thioether
  • Hemithioaminal
  • Sulfenyl compound
  • Organic 1,3-dipolar compound
  • Allyl-type 1,3-dipolar organic compound
  • Organic salt
  • Organonitrogen compound
  • Organooxygen compound
  • Organosulfur compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Carbonyl group
  • Organic oxygen compound
  • Organic cation
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic 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
logP1.17ALOGPS
logP1.33ChemAxon
logS-3.2ALOGPS
pKa (Strongest Basic)7.27ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area109.16 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity84.17 m³·mol⁻¹ChemAxon
Polarizability33.52 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M-2H]-205.62830932474
DeepCCS[M+Na]+181.91830932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
[(3S,3Ar,6R,6aS)-6-nitrooxy-2,3,3a,5,6,6a-hexahydrofuro[3,2-b]furan-3-yl] 2-ethylsulfanyl-1,2-dihydropyridine-3-carboxylateCCSC1NC=CC=C1C(=O)OC1COC2C(COC12)O[N+]([O-])=O4353.9Standard polar33892256
[(3S,3Ar,6R,6aS)-6-nitrooxy-2,3,3a,5,6,6a-hexahydrofuro[3,2-b]furan-3-yl] 2-ethylsulfanyl-1,2-dihydropyridine-3-carboxylateCCSC1NC=CC=C1C(=O)OC1COC2C(COC12)O[N+]([O-])=O2638.1Standard non polar33892256
[(3S,3Ar,6R,6aS)-6-nitrooxy-2,3,3a,5,6,6a-hexahydrofuro[3,2-b]furan-3-yl] 2-ethylsulfanyl-1,2-dihydropyridine-3-carboxylateCCSC1NC=CC=C1C(=O)OC1COC2C(COC12)O[N+]([O-])=O2671.4Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
[(3S,3Ar,6R,6aS)-6-nitrooxy-2,3,3a,5,6,6a-hexahydrofuro[3,2-b]furan-3-yl] 2-ethylsulfanyl-1,2-dihydropyridine-3-carboxylate,1TMS,isomer #1CCSC1C(C(=O)OC2COC3C(O[N+](=O)[O-])COC23)=CC=CN1[Si](C)(C)C2810.8Semi standard non polar33892256
[(3S,3Ar,6R,6aS)-6-nitrooxy-2,3,3a,5,6,6a-hexahydrofuro[3,2-b]furan-3-yl] 2-ethylsulfanyl-1,2-dihydropyridine-3-carboxylate,1TMS,isomer #1CCSC1C(C(=O)OC2COC3C(O[N+](=O)[O-])COC23)=CC=CN1[Si](C)(C)C2604.5Standard non polar33892256
[(3S,3Ar,6R,6aS)-6-nitrooxy-2,3,3a,5,6,6a-hexahydrofuro[3,2-b]furan-3-yl] 2-ethylsulfanyl-1,2-dihydropyridine-3-carboxylate,1TMS,isomer #1CCSC1C(C(=O)OC2COC3C(O[N+](=O)[O-])COC23)=CC=CN1[Si](C)(C)C3994.0Standard polar33892256
[(3S,3Ar,6R,6aS)-6-nitrooxy-2,3,3a,5,6,6a-hexahydrofuro[3,2-b]furan-3-yl] 2-ethylsulfanyl-1,2-dihydropyridine-3-carboxylate,1TBDMS,isomer #1CCSC1C(C(=O)OC2COC3C(O[N+](=O)[O-])COC23)=CC=CN1[Si](C)(C)C(C)(C)C3031.5Semi standard non polar33892256
[(3S,3Ar,6R,6aS)-6-nitrooxy-2,3,3a,5,6,6a-hexahydrofuro[3,2-b]furan-3-yl] 2-ethylsulfanyl-1,2-dihydropyridine-3-carboxylate,1TBDMS,isomer #1CCSC1C(C(=O)OC2COC3C(O[N+](=O)[O-])COC23)=CC=CN1[Si](C)(C)C(C)(C)C2790.2Standard non polar33892256
[(3S,3Ar,6R,6aS)-6-nitrooxy-2,3,3a,5,6,6a-hexahydrofuro[3,2-b]furan-3-yl] 2-ethylsulfanyl-1,2-dihydropyridine-3-carboxylate,1TBDMS,isomer #1CCSC1C(C(=O)OC2COC3C(O[N+](=O)[O-])COC23)=CC=CN1[Si](C)(C)C(C)(C)C4122.5Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - [(3S,3Ar,6R,6aS)-6-nitrooxy-2,3,3a,5,6,6a-hexahydrofuro[3,2-b]furan-3-yl] 2-ethylsulfanyl-1,2-dihydropyridine-3-carboxylate GC-MS (Non-derivatized) - 70eV, Positivesplash10-000l-4952000000-e3e48f4942398219b50b2021-09-23Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - [(3S,3Ar,6R,6aS)-6-nitrooxy-2,3,3a,5,6,6a-hexahydrofuro[3,2-b]furan-3-yl] 2-ethylsulfanyl-1,2-dihydropyridine-3-carboxylate GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart 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 IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
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 ]