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Record Information
Version3.6
Creation Date2013-07-22 19:51:31 UTC
Update Date2016-02-11 08:19:25 UTC
HMDB IDHMDB61157
Secondary Accession NumbersNone
Metabolite Identification
Common NameN-(2-Hydroxyethyl)-morpholine N-oxide
DescriptionN-(2-Hydroxyethyl)-morpholine N-oxide is a metabolite of mycophenolate mofetil. Mycophenolate mofetil (MMF) (brand names CellCept, Myfortic) is an immunosuppressant and prodrug of mycophenolic acid, used extensively in transplant medicine. It is a reversible inhibitor of inosine monophosphate dehydrogenase (IMPDH) in purine biosynthesis which is necessary for the growth of T cells and B cells. Other cells are able to recover purines via a separate, scavenger, pathway and are, thus, able to escape the effect. MMF is a less toxic alternative to azathioprine. (Wikipedia)
Structure
Thumb
SynonymsNot Available
Chemical FormulaC6H13NO3
Average Molecular Weight147.1723
Monoisotopic Molecular Weight147.089543287
IUPAC Name2-(morpholin-4-yloxy)ethan-1-ol
Traditional Name2-(morpholin-4-yloxy)ethanol
CAS Registry NumberNot Available
SMILES
OCCON1CCOCC1
InChI Identifier
InChI=1S/C6H13NO3/c8-3-6-10-7-1-4-9-5-2-7/h8H,1-6H2
InChI KeyInChIKey=WTPGFRPRHSDKNE-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound 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
  • Oxacycle
  • Azacycle
  • N-organohydroxylamine
  • Ether
  • Dialkyl ether
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Alcohol
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
StatusExpected but not Quantified
Origin
  • Drug metabolite
Biofunction
  • Waste products
ApplicationNot Available
Cellular locations
  • Cytoplasm
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility883.0 mg/mLALOGPS
logP-0.66ALOGPS
logP-1.1ChemAxon
logS0.78ALOGPS
pKa (Strongest Acidic)15.05ChemAxon
pKa (Strongest Basic)0.28ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area41.93 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity36.31 m3·mol-1ChemAxon
Polarizability15.36 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
Pathways
NameSMPDB LinkKEGG Link
Mycophenolic Acid Metabolism PathwaySMP00652Not Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableNormal
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableNormal
  • Not Applicable
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDDBMET00920
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB61157
Metagene LinkHMDB61157
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available