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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2013-07-22 19:51:28 UTC
Update Date2019-07-23 07:15:52 UTC
HMDB IDHMDB0061156
Secondary Accession Numbers
  • HMDB61156
Metabolite Identification
Common NameN-(2-Carboxymethyl)-morpholine
DescriptionN-(2-Carboxymethyl)-morpholine belongs to the class of organic compounds known as alpha amino acids. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon). N-(2-Carboxymethyl)-morpholine is a very strong basic compound (based on its pKa). Within humans, N-(2-carboxymethyl)-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 through the action of 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; which is mediated by the enzymes liver carboxylesterase 1 and cocaine esterase. In humans, N-(2-carboxymethyl)-morpholine is involved in mycophenolic acid metabolism pathway. N-(2-Carboxymethyl)-morpholine is a metabolite of mycophenolate mofetil. Other cells are able to recover purines via a separate, scavenger, pathway and are, thus, able to escape the effect. 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. Mycophenolate mofetil (MMF) (brand names CellCept, Myfortic) is an immunosuppressant and prodrug of mycophenolic acid, used extensively in transplant medicine.
Structure
Data?1563866152
SynonymsNot Available
Chemical FormulaC6H11NO3
Average Molecular Weight145.1564
Monoisotopic Molecular Weight145.073893223
IUPAC Name2-(morpholin-4-yl)acetic acid
Traditional Namemorpholin-4-ylacetic acid
CAS Registry NumberNot Available
SMILES
OC(=O)CN1CCOCC1
InChI Identifier
InChI=1S/C6H11NO3/c8-6(9)5-7-1-3-10-4-2-7/h1-5H2,(H,8,9)
InChI KeyVIWZVFVJPXTXPA-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as alpha amino acids. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon).
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentAlpha amino acids
Alternative Parents
Substituents
  • Alpha-amino acid
  • Morpholine
  • Oxazinane
  • Tertiary amine
  • Amino acid
  • Tertiary aliphatic amine
  • Carboxylic acid
  • Dialkyl ether
  • Ether
  • Monocarboxylic acid or derivatives
  • Organoheterocyclic compound
  • Azacycle
  • Oxacycle
  • Organonitrogen compound
  • Organic oxygen compound
  • Carbonyl group
  • Organooxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Amine
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Source:

Biological location:

Process

Naturally occurring process:

Role

Biological role:

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 Solubility1040 g/LALOGPS
logP-1.8ALOGPS
logP-2.7ChemAxon
logS0.85ALOGPS
pKa (Strongest Acidic)2.95ChemAxon
pKa (Strongest Basic)6.45ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area49.77 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity35.15 m³·mol⁻¹ChemAxon
Polarizability14.17 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0f6x-9300000000-f93563d3d3c0b79c6596Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0uk9-7900000000-6bc3cdc425e644b0801bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udj-0900000000-09c0da4638317879a7cdSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0900000000-c572fa66c2a7d7f26baaSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0kfx-9100000000-6b84eedcb41995fbd2b6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0900000000-c37c70455dd0f3ef9fddSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0f6x-0900000000-e6e119a3b2b58f2dda35Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-006x-9100000000-473c748012f7df687eaeSpectrum
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Blood
  • Urine
Tissue Locations
  • Kidney
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableNormal
    details
    UrineExpected but not Quantified Not AvailableNot AvailableNormal
      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 Compound438968
      PDB IDNot Available
      ChEBI IDNot Available
      Food Biomarker OntologyNot Available
      VMH IDNot Available
      References
      Synthesis ReferenceNot Available
      Material Safety Data Sheet (MSDS)Not Available
      General ReferencesNot Available