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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2021-09-10 22:45:30 UTC
Update Date2022-09-22 17:45:00 UTC
HMDB IDHMDB0245703
Secondary Accession NumbersNone
Metabolite Identification
Common Name1-Ethoxy-N-(3-morpholin-4-yloxadiazol-3-ium-5-yl)methanimidate
DescriptionMolsidomine, also known as molsidomin stada or corvaton, belongs to the class of organic compounds known as morpholines. These are organic compounds containing a morpholine moiety, which consists of a six-member aliphatic saturated ring with the formula C4H9NO, where the oxygen and nitrogen atoms lie at positions 1 and 4, respectively. Molsidomine is a prodrug that is hydrolysed to linsidomine (SIN-1) in the liver via first-pass effect, which subsequently releases NO. 44–59% of molsidomine reach the bloodstream in unchanged form, 3–11% of which are bound to plasma proteins. Molsidomine is an extremely weak basic (essentially neutral) compound (based on its pKa). Ergolines can antagonise the effects of molsidomine. It is also used to treat angina in the context of an acute myocardial infarction. The substance is sensitive to ultraviolet light at wavelengths shorter than 320 nm. This compound has been identified in human blood as reported by (PMID: 31557052 ). 1-ethoxy-n-(3-morpholin-4-yloxadiazol-3-ium-5-yl)methanimidate is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically 1-Ethoxy-N-(3-morpholin-4-yloxadiazol-3-ium-5-yl)methanimidate 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
CorvatonMeSH
MolsidainMeSH
MorsydomineMeSH
SIN 10MeSH
Molsidomin stadaMeSH
Von CT, molsidominMeSH
Molsi 1a pharmaMeSH
MolsibetaMeSH
SIN10MeSH
Molsi-azuMeSH
MolsicorMeSH
Fali corMeSH
MolsihexalMeSH
Molsi azuMeSH
MolsidominMeSH
Molsidomin ratiopharmMeSH
Fali-corMeSH
SIN-10MeSH
KorvatoneMeSH
Molsidomin heumannMeSH
Molsidomin-ratiopharmMeSH
Molsi purenMeSH
SydnopharmMeSH
DuracoronMeSH
MTW-MolsidominMeSH
Heumann, molsidominMeSH
MolsiketMeSH
MTW MolsidominMeSH
Molsidomin von CTMeSH
CorpeaMeSH
Molsi-purenMeSH
Alpharma brand OF molsidomineMeSH
Molsidomine normon brandMeSH
MolsidominratiopharmMeSH
Stadapharm brand OF molsidomineMeSH
CT Arzneimittel brand OF molsidomineMeSH
1a Brand OF molsidomineMeSH
Azupharma brand OF molsidomineMeSH
Molsidomine ratiopharm brandMeSH
Normon brand OF molsidomineMeSH
Schwarz brand OF molsidomineMeSH
MolsidomineMeSH
Molsidomine aventis brandMeSH
Molsidomine salutas brandMeSH
Molsidomine schwarz brandMeSH
Molsidomine CT-arzneimittel brandMeSH
Sanol brand OF molsidomineMeSH
CT-Arzneimittel brand OF molsidomineMeSH
Hexal brand OF molsidomineMeSH
Merck dura brand OF molsidomineMeSH
Molsidomine heumann brandMeSH
Molsidomine stadapharm brandMeSH
Salutas brand OF molsidomineMeSH
Heumann brand OF molsidomineMeSH
Molsidomine betapharm brandMeSH
Aventis brand OF molsidomineMeSH
Molsidomine azupharma brandMeSH
Molsidomine hexal brandMeSH
Molsidomine MTW brandMeSH
Betapharm brand OF molsidomineMeSH
Ratiopharm brand OF molsidomineMeSH
MTW Brand OF molsidomineMeSH
Molsidomine 1a brandMeSH
Molsidomine alpharma brandMeSH
Molsidomine sanol brandMeSH
Ethyl N-[3-(morpholin-4-yl)-5H-1,2,3λ⁵-oxadiazol-5-ylidene]carbamic acidGenerator
Chemical FormulaC9H14N4O4
Average Molecular Weight242.235
Monoisotopic Molecular Weight242.101504947
IUPAC Name5-[(ethoxycarbonyl)azanidyl]-3-(morpholin-4-yl)-1,2,3λ⁵-oxadiazol-3-ylium
Traditional Name5-[(ethoxycarbonyl)azanidyl]-3-(morpholin-4-yl)-1,2,3λ⁵-oxadiazol-3-ylium
CAS Registry NumberNot Available
SMILES
CCOC(=O)[N-]C1=C[N+](=NO1)N1CCOCC1
InChI Identifier
InChI=1S/C9H14N4O4/c1-2-16-9(14)10-8-7-13(11-17-8)12-3-5-15-6-4-12/h7H,2-6H2,1H3
InChI KeyXLFWDASMENKTKL-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as morpholines. These are organic compounds containing a morpholine moiety, which consists of a six-member aliphatic saturated ring with the formula C4H9NO, where the oxygen and nitrogen atoms lie at positions 1 and 4, respectively.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassOxazinanes
Sub ClassMorpholines
Direct ParentMorpholines
Alternative Parents
Substituents
  • Morpholine
  • Carbonic acid derivative
  • Dialkyl ether
  • Ether
  • Propargyl-type 1,3-dipolar organic compound
  • Organic 1,3-dipolar compound
  • Azacycle
  • Oxacycle
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Organic nitrogen compound
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • 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
logP-1ALOGPS
logP-1ChemAxon
logS-1.4ALOGPS
pKa (Strongest Acidic)7.99ChemAxon
pKa (Strongest Basic)-3.2ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area77.91 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity76.99 m³·mol⁻¹ChemAxon
Polarizability23.74 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+151.43630932474
DeepCCS[M-H]-149.04130932474
DeepCCS[M-2H]-181.92430932474
DeepCCS[M+Na]+157.34930932474
AllCCS[M+H]+153.532859911
AllCCS[M+H-H2O]+149.832859911
AllCCS[M+NH4]+157.032859911
AllCCS[M+Na]+158.032859911
AllCCS[M-H]-155.432859911
AllCCS[M+Na-2H]-155.632859911
AllCCS[M+HCOO]-155.832859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
1-Ethoxy-N-(3-morpholin-4-yloxadiazol-3-ium-5-yl)methanimidateCCOC(=O)[N-]C1=C[N+](=NO1)N1CCOCC12681.4Standard polar33892256
1-Ethoxy-N-(3-morpholin-4-yloxadiazol-3-ium-5-yl)methanimidateCCOC(=O)[N-]C1=C[N+](=NO1)N1CCOCC11971.4Standard non polar33892256
1-Ethoxy-N-(3-morpholin-4-yloxadiazol-3-ium-5-yl)methanimidateCCOC(=O)[N-]C1=C[N+](=NO1)N1CCOCC11948.8Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 1-Ethoxy-N-(3-morpholin-4-yloxadiazol-3-ium-5-yl)methanimidate GC-MS (Non-derivatized) - 70eV, Positivesplash10-01dj-7910000000-63f8ea7ee27b88f0912f2021-09-23Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 1-Ethoxy-N-(3-morpholin-4-yloxadiazol-3-ium-5-yl)methanimidate 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 - 1-Ethoxy-N-(3-morpholin-4-yloxadiazol-3-ium-5-yl)methanimidate 10V, Positive-QTOFsplash10-0006-6490000000-c5e4bc21cb85b4e60a702016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-Ethoxy-N-(3-morpholin-4-yloxadiazol-3-ium-5-yl)methanimidate 20V, Positive-QTOFsplash10-000j-9220000000-abafa3380cf8a5a4d0bd2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-Ethoxy-N-(3-morpholin-4-yloxadiazol-3-ium-5-yl)methanimidate 40V, Positive-QTOFsplash10-000l-9400000000-daea7c7e4e60434835062016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-Ethoxy-N-(3-morpholin-4-yloxadiazol-3-ium-5-yl)methanimidate 10V, Negative-QTOFsplash10-0006-5290000000-6d4f7dd885c9fb6c59ad2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-Ethoxy-N-(3-morpholin-4-yloxadiazol-3-ium-5-yl)methanimidate 20V, Negative-QTOFsplash10-002n-9560000000-93fecea706c4877048ad2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-Ethoxy-N-(3-morpholin-4-yloxadiazol-3-ium-5-yl)methanimidate 40V, Negative-QTOFsplash10-052v-9000000000-a53b47a7b42292d341b52016-08-03Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-10-13Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-10-13Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-10-13Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-10-13Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-10-13Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-10-13Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-10-13Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-10-13Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-10-13Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-10-13Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-10-13Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-10-13Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-10-13Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-10-13Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-10-13Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-10-13Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-10-13Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-10-13Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-10-13Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-10-13Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected 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 IDDB09282
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 LinkMolsidomine
METLIN IDNot Available
PubChem Compound4238
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 ]