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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2013-06-15 18:25:46 UTC
Update Date2019-07-23 07:14:47 UTC
HMDB IDHMDB0060650
Secondary Accession Numbers
  • HMDB60650
Metabolite Identification
Common NameN-(2-Hydroxyethyl)-morpholine
DescriptionN-(2-Hydroxyethyl)-morpholine, also known as 2-(4-morpholinyl)ethanol, 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. Other cells are able to recover purines via a separate, scavenger, pathway and are, thus, able to escape the effect. N-(2-Hydroxyethyl)-morpholine is a very strong basic compound (based on its pKa). Within humans, N-(2-hydroxyethyl)-morpholine participates in a number of enzymatic reactions. In particular, N-(2-carboxymethyl)-morpholine, N-(2-hydroxyethyl)-morpholine, and N-(2-hydroxyethyl)-morpholine N-oxide can be biosynthesized from mycophenolate mofetil; which is catalyzed by the enzyme cocaine esterase. In addition, N-(2-carboxymethyl)-morpholine, N-(2-hydroxyethyl)-morpholine, and N-(2-hydroxyethyl)-morpholine N-oxide can be biosynthesized from mycophenolate mofetil through the action of the enzymes liver carboxylesterase 1 and cocaine esterase. Mycophenolate mofetil (MMF) (brand names CellCept, Myfortic) is an immunosuppressant and prodrug of mycophenolic acid, used extensively in transplant medicine. In humans, N-(2-hydroxyethyl)-morpholine is involved in mycophenolic acid metabolism pathway. N-(2-Hydroxyethyl)-morpholine is a metabolite of mycophenolate mofetil. 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. MMF is a less toxic alternative to azathioprine.
Structure
Data?1563866087
Synonyms
ValueSource
2-(4-Morpholinyl)ethanolChEBI
4-(2-Hydroxyethyl)morpholineChEBI
4-MorpholineethanolChEBI
HydroxyethylmorpholineChEBI
Morpholine ethanolChEBI
N(2-Hydroxyethyl)morpholineChEBI
N-beta-HydroxyethylmorpholineChEBI
N-b-HydroxyethylmorpholineGenerator
N-Β-hydroxyethylmorpholineGenerator
Chemical FormulaC6H13NO2
Average Molecular Weight131.1729
Monoisotopic Molecular Weight131.094628665
IUPAC Name2-(morpholin-4-yl)ethan-1-ol
Traditional Name4-morpholineethanol
CAS Registry NumberNot Available
SMILES
OCCN1CCOCC1
InChI Identifier
InChI=1S/C6H13NO2/c8-4-1-7-2-5-9-6-3-7/h8H,1-6H2
InChI KeyKKFDCBRMNNSAAW-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
  • 1,2-aminoalcohol
  • Tertiary aliphatic amine
  • Tertiary amine
  • Alkanolamine
  • Dialkyl ether
  • Ether
  • Oxacycle
  • Azacycle
  • Organic nitrogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Primary alcohol
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Amine
  • Organic oxygen compound
  • Alcohol
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Source

Route of exposure

Process

Naturally occurring process

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
Water Solubility1110 g/LALOGPS
logP10(-0.58) g/LALOGPS
logP10(-0.72) g/LChemAxon
logS10(0.93) g/LALOGPS
pKa (Strongest Acidic)15.59ChemAxon
pKa (Strongest Basic)7.19ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area32.7 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity35.35 m³·mol⁻¹ChemAxon
Polarizability14.4 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+126.23131661259
DarkChem[M-H]-120.83531661259

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
N-(2-Hydroxyethyl)-morpholineOCCN1CCOCC11840.1Standard polar33892256
N-(2-Hydroxyethyl)-morpholineOCCN1CCOCC11113.8Standard non polar33892256
N-(2-Hydroxyethyl)-morpholineOCCN1CCOCC11118.2Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
N-(2-Hydroxyethyl)-morpholine,1TMS,isomer #1C[Si](C)(C)OCCN1CCOCC11250.0Semi standard non polar33892256
N-(2-Hydroxyethyl)-morpholine,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OCCN1CCOCC11474.6Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - N-(2-Hydroxyethyl)-morpholine GC-MS (Non-derivatized) - 70eV, Positivesplash10-0udr-9300000000-a428bf4121b4d2205aeb2017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - N-(2-Hydroxyethyl)-morpholine GC-MS (1 TMS) - 70eV, Positivesplash10-0udr-7900000000-76434aaf20aeff698ca62017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - N-(2-Hydroxyethyl)-morpholine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - N-(2-Hydroxyethyl)-morpholine 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 - N-(2-Hydroxyethyl)-morpholine 10V, Positive-QTOFsplash10-001i-0900000000-f187a9992ab2eee6260c2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-(2-Hydroxyethyl)-morpholine 20V, Positive-QTOFsplash10-03e9-2900000000-a0b8a40fe23c332b36992016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-(2-Hydroxyethyl)-morpholine 40V, Positive-QTOFsplash10-052v-9100000000-ba9841aa75800c9c54cd2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-(2-Hydroxyethyl)-morpholine 10V, Negative-QTOFsplash10-001i-1900000000-44fbfc21ff1e48a3d6f12016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-(2-Hydroxyethyl)-morpholine 20V, Negative-QTOFsplash10-001i-3900000000-07561feaf57473965bc62016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-(2-Hydroxyethyl)-morpholine 40V, Negative-QTOFsplash10-052f-9000000000-2032f99671dad68f2d8a2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-(2-Hydroxyethyl)-morpholine 10V, Positive-QTOFsplash10-03e9-0900000000-79beccd31ed773887abc2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-(2-Hydroxyethyl)-morpholine 20V, Positive-QTOFsplash10-0ik9-1900000000-53c62a4955a59f5d57072021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-(2-Hydroxyethyl)-morpholine 40V, Positive-QTOFsplash10-01vk-9300000000-8a1d8096462abddc74da2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-(2-Hydroxyethyl)-morpholine 10V, Negative-QTOFsplash10-001i-1900000000-2df8658716f49b191fca2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-(2-Hydroxyethyl)-morpholine 20V, Negative-QTOFsplash10-0gvp-9600000000-d8b093f22240665ef4932021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-(2-Hydroxyethyl)-morpholine 40V, Negative-QTOFsplash10-0006-9000000000-a93051099d4f052862fa2021-10-12Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Blood
  • Urine
Tissue Locations
  • Kidney
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableNormal
      Not Available
details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableNormal
      Not Available
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 Compound61163
PDB IDNot Available
ChEBI ID67144
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 ReferencesNot Available