Isosorbide mononitrate (CED0005326)

Record Information
Version1.0
Creation Date2016-05-22 03:42:07 UTC
Update Date2026-08-23 16:27:39 UTC
Accession NumberCHEM016743
Identification
Common NameIsosorbide mononitrate
ClassSmall Molecule
Description
Isosorbide mononitrate is an organic compound with the formula C6H9NO6 and an average molecular weight of 191.14 g/mol. Isosorbide mononitrate belongs to the isosorbides, a subclass of furofurans within the organic compounds. It is categorized as an organoheterocyclic compound. The compound is found in or released from 37 recorded sources across several sectors. In healthcare, pharmaceuticals, and veterinary products, it is used as a vasodilator for the treatment of cardiac diseases. Other recorded sources include household cleaning and consumer products, such as bleaching agents, cigar cigarettes, non electric simulated smoking devices, other smoking requisites, and pipe accessories. It is also associated with electrical and electronic equipment, including amplifiers, antennas, auxiliary devices, coils, and communication cables or conductors. Building and construction sources include fencing, floors, stairs and ramps, and sunshades awnings or outside screens. Additionally, it is linked to food, food processing, and cookware, specifically the preparation of vinegar and fermentation processes for beer, as well as household items such as credit card holders. The recorded exposure route for isosorbide mononitrate is oral. Regarding its biological activity, the compound has one recorded protein target, acting as an activator of Guanylate cyclase soluble subunit alpha-2 (GUCY1A2).
Contaminant TypeNot Available
Chemical Structure
Synonyms
ValueSource
CoranginChEBI
DurideChEBI
ElantanChEBI
ImdurChEBI
ImtrateChEBI
IsmexinChEBI
IsmoChEBI
IsmoxChEBI
Isosorbidi mononitrasChEBI
MedocorChEBI
MonicorChEBI
mono CoraxChEBI
MonocedocardChEBI
MonocordChEBI
Monodur durulesChEBI
MonoketChEBI
MonolongChEBI
MonomaxChEBI
MononitChEBI
Mononitrate d'isosorbideChEBI
Mononitrato de isosorbidaChEBI
MonoprontChEBI
Monosorb XL 60ChEBI
MonosorbitrateChEBI
MonosordilChEBI
NitraminChEBI
OlicardChEBI
OrasorbilChEBI
PertilChEBI
PromocardChEBI
SigacoraChEBI
SorbimonChEBI
TurimonitChEBI
UniketChEBI
VasdilatChEBI
Imtric acidGenerator
Mononitric acid d'isosorbideGenerator
Monosorbitric acidGenerator
Isosorbide mononitric acidGenerator
IHDHMDB
ISMNHMDB
5-ISMNHMDB
MonizidHMDB
Isosorbide-5-mononitrateHMDB
MonocinqueHMDB
5-ISMN durulesHMDB
Olicard-retardHMDB
mono Mac 50DHMDB
Olicard 40HMDB
Isosorbide-5-nitrateHMDB
Chemical FormulaC6H9NO6
Average Molecular Mass191.139 g/mol
Monoisotopic Mass191.043 g/mol
CAS Registry Number16051-77-7
IUPAC Name(3R,3aS,6S,6aR)-6-hydroxy-hexahydrofuro[3,2-b]furan-3-yl nitrate
Traditional Namemonit
SMILES[H][C@]12OC[C@@H](O[N+]([O-])=O)[C@@]1([H])OC[C@@H]2O
InChI IdentifierInChI=1S/C6H9NO6/c8-3-1-11-6-4(13-7(9)10)2-12-5(3)6/h3-6,8H,1-2H2/t3-,4+,5+,6+/m0/s1
InChI KeyYWXYYJSYQOXTPL-SLPGGIOYSA-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
  • Organic nitrate
  • Tetrahydrofuran
  • Alkyl nitrate
  • Organic nitric acid or derivatives
  • Secondary alcohol
  • Organic nitro compound
  • Dialkyl ether
  • Ether
  • Oxacycle
  • Allyl-type 1,3-dipolar organic compound
  • Organic 1,3-dipolar compound
  • Organooxygen compound
  • Organic oxide
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Alcohol
  • Organic zwitterion
  • Organic nitrogen compound
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Organoleptic EffectsNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility57 g/LALOGPS
logP-0.74ALOGPS
logP-0.48ChemAxon
logS-0.53ALOGPS
pKa (Strongest Acidic)13.34ChemAxon
pKa (Strongest Basic)-3.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area93.74 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity38.08 m³·mol⁻¹ChemAxon
Polarizability15.85 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrumsplash10-000f-9300000000-b4ec727e72efe8ad217bNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS Spectrumsplash10-0083-9640000000-0ad29341e87830c45375Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-004l-0900000000-278e799da1d244cf28efNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-004i-0900000000-c756580de33aee3c9b29Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-03di-5900000000-4c71f011ae5de1efcfc3Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-006y-1900000000-2590c61a57ba7239bfe7Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00fs-1900000000-685189efcbfd15fe619fNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-9300000000-36bfdd3cceae7c035378Not AvailableView Spectrum
1D NMR1H NMR Spectrum (1D, D2O, predicted)Not AvailableNot AvailableView Spectrum
1D NMR13C NMR Spectrum (1D, D2O, predicted)Not AvailableNot AvailableView Spectrum
Toxicity Profile
Mechanism of ToxicityNot Available
Carcinogenicity (IARC Classification)Not Available
Minimum Risk LevelNot Available
SymptomsNot Available
TreatmentNot Available
Toxicity Values
Toxicity ValueUnitValue RangeOrganismDose DescriptorRoute of ExposurePredicted or ExperimentalReference
2422.0Log mg/kg[1400:4300]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
Exposure Sources
Source IDSourceSectorReference
233BrushesPersonal care & cosmeticsNot Available
287Vasodilators used in cardiac diseasesHealthcare, pharmaceuticals & veterinary productsNot Available
496FencingBuilding & ConstructionNot Available
497FloorsBuilding & ConstructionNot Available
500Stairs And RampsBuilding & ConstructionNot Available
501Sunshades Awnings Or Outside ScreensBuilding & ConstructionNot Available
502Sunshades Awnings Or Outside ScreensBuilding & ConstructionNot Available
503Tents Or CanopiesBuilding & ConstructionNot Available
505AmplifiersElectrical & Electronic EquipmentNot Available
506AntennasElectrical & Electronic EquipmentNot Available
507Auxiliary DevicesElectrical & Electronic EquipmentNot Available
508CoilsElectrical & Electronic EquipmentNot Available
510Communication Cables Or ConductorsElectrical & Electronic EquipmentNot Available
513Cores Yokes Or ArmaturesElectrical & Electronic EquipmentNot Available
514Discharge LampsElectrical & Electronic EquipmentNot Available
516Electric Hearing AidsElectrical & Electronic EquipmentNot Available
517Electric SwitchesElectrical & Electronic EquipmentNot Available
518Electrically Stimulated Smoking DevicesElectrical & Electronic EquipmentNot Available
520Emergency Protective DevicesElectrical & Electronic EquipmentNot Available
521Fixed Capacitors And Their ManufactureElectrical & Electronic EquipmentNot Available
525Line Transmission SystemsElectrical & Electronic EquipmentNot Available
527MagnetsElectrical & Electronic EquipmentNot Available
529Power CablesElectrical & Electronic EquipmentNot Available
530Radio Transmission SystemsElectrical & Electronic EquipmentNot Available
532SelectorsElectrical & Electronic EquipmentNot Available
534Still Video CamerasElectrical & Electronic EquipmentNot Available
537Television SystemsElectrical & Electronic EquipmentNot Available
539Video GamesElectrical & Electronic EquipmentNot Available
544Fermentation Processes For BeerFood, food processing & cookwareNot Available
548Preparation Of VinegarFood, food processing & cookwareNot Available
555Bleaching AgentsHousehold cleaning & consumer productsNot Available
556Cigar CigarettesHousehold cleaning & consumer productsNot Available
559Non Electric Simulated Smoking DevicesHousehold cleaning & consumer productsNot Available
560Other Smoking RequisitesHousehold cleaning & consumer productsNot Available
562Pipe AccessoriesHousehold cleaning & consumer productsNot Available
564Soap DispensersHousehold cleaning & consumer productsNot Available
569Tobacco Smoke FiltersHousehold cleaning & consumer productsNot Available
572Credit Card HoldersHousehold itemsNot Available
578Making CigarsIndustrial manufacturing & chemical processingNot Available
579Manufacture Of Iron Or SteelIndustrial manufacturing & chemical processingNot Available
581Paper Making MachinesIndustrial manufacturing & chemical processingNot Available
583Anchoring EquipmentMarine, shipping & aquacultureNot Available
594Ship HullsMarine, shipping & aquacultureNot Available
598Fertiliser DistributorsAgriculture & land managementNot Available
601Lawn MowersAgriculture & land managementNot Available
602MolluscicidesAgriculture & land managementNot Available
603NematocidesAgriculture & land managementNot Available
604Pest AttractantsAgriculture & land managementNot Available
605Pest RepellantsAgriculture & land managementNot Available
607Rodenticides(1)Agriculture & land managementNot Available
608RodenticidesAgriculture & land managementNot Available
609AftershavePersonal care & cosmeticsNot Available
613DepilatoriesPersonal care & cosmeticsNot Available
617Lip Care ProductsPersonal care & cosmeticsNot Available
620Card GamesRecreation & sports surfacesNot Available
621Chutes And SlidesRecreation & sports surfacesNot Available
624Merry Go RoundsRecreation & sports surfacesNot Available
630ToysRecreation & sports surfacesNot Available
640Embroidering And TuftingTextiles, leather & furnishingsNot Available
643HeadwearTextiles, leather & furnishingsNot Available
647Multicolour DyeingTextiles, leather & furnishingsNot Available
649Pins ClothesTextiles, leather & furnishingsNot Available
650Purses Luggage Hand BagsTextiles, leather & furnishingsNot Available
651Purses Money Bags WalletsTextiles, leather & furnishingsNot Available
652RopesTextiles, leather & furnishingsNot Available
653SewingTextiles, leather & furnishingsNot Available
658Touch FastenersTextiles, leather & furnishingsNot Available
661UmbrellasTextiles, leather & furnishingsNot Available
662Yarns Or ThreadsTextiles, leather & furnishingsNot Available
Pathways
2 pathways
Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Cholinesterase structureClick to view 3D structureCholinesteraseP06276HumansPredicted (SEA)5967.38
Click to view 3D structureBeta-galactosidaseP29853Aspergillus nigerPredicted (SEA)5.29375
Click to view 3D structureMultifunctional protein ADE2P38024Gallus gallusPredicted (SEA)154.064
Lysosomal alpha-glucosidase structureClick to view 3D structureLysosomal alpha-glucosidaseP10253HumansPredicted (SEA)163.561
Maltase-glucoamylase structureClick to view 3D structureMaltase-glucoamylaseO43451HumansPredicted (SEA)706.404
Click to view 3D structureSucrase-isomaltase, intestinalP23739Rattus norvegicusPredicted (SEA)93.4191
Endolysin structureClick to view 3D structureEndolysinP00720Enterobacteria phage T4Predicted (SEA)156.243
Sucrase-isomaltase, intestinal structureClick to view 3D structureSucrase-isomaltase, intestinalP14410HumansPredicted (SEA)195.402
Click to view 3D structureAlpha-galactosidase CQ9UUZ4Aspergillus nigerPredicted (SEA)10.821
Click to view 3D structureBeta-mannosidaseO00462HumansPredicted (SEA)248.573
Click to view 3D structureNon-lysosomal glucosylceramidaseQ69ZF3Mus musculusPredicted (SEA)85.0114
Click to view 3D structureLysosomal alpha-glucosidaseQ6P7A9Rattus norvegicusPredicted (SEA)89.4488
Click to view 3D structureInositol monophosphatase 1P20456Bos taurusPredicted (SEA)1016.87
Click to view 3D structureMuscarinic acetylcholine receptor M1P08482Rattus norvegicusPredicted (SEA)7122.89
Lysosomal acid glucosylceramidase structureClick to view 3D structureLysosomal acid glucosylceramidaseP04062HumansPredicted (SEA)3952.25
Autotaxin structureClick to view 3D structureAutotaxinQ13822HumansPredicted (SEA)5499.27
Click to view 3D structureGlycogen debranching enzymeP35573HumansPredicted (SEA)23.3548
Click to view 3D structureEstrogen sulfotransferaseQ95MF8Sus scrofaPredicted (SEA)368.149
Click to view 3D structureNon-lysosomal glucosylceramidaseQ9HCG7HumansPredicted (SEA)725.944
Muscarinic acetylcholine receptor M1 structureClick to view 3D structureMuscarinic acetylcholine receptor M1P11229HumansPredicted (SEA)7732.37
Click to view 3D structureP2Y purinoceptor 6Q15077HumansPredicted (SEA)3331.17
Click to view 3D structureSH3 and multiple ankyrin repeat domains protein 3Q4ACU6Mus musculusPredicted (SEA)176.484
Fatty acid synthase structureClick to view 3D structureFatty acid synthaseP49327HumansPredicted (SEA)7535.18
Click to view 3D structureLong-chain fatty acid transport protein 4Q6P1M0HumansPredicted (SEA)858.132
Click to view 3D structureMuscarinic acetylcholine receptor M2P10980Rattus norvegicusPredicted (SEA)7083.5
Concentrations
Not Available
External Links
DrugBank IDDB01020
HMDB IDHMDB0015155
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkIsosorbide mononitrate
Chemspider ID25736
ChEBI ID6062
PubChem Compound ID27661
Kegg Compound IDC07714
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Authors unspecified: Organic Nitrates. 2012.
2. Abshagen UW: Pharmacokinetics of isosorbide mononitrate. Am J Cardiol. 1992 Nov 27;70(17):61G-66G. doi: 10.1016/0002-9149(92)90028-w.
3. Yazdizadeh H, Abedi P, Najar S, Angali KA: The impact of isosorbide mononitrate on cervical ripening and labor induction in primiparous women with term pregnancy: A double-blind, randomized, controlled trial. Iran J Nurs Midwifery Res. 2013 May;18(3):246-50.