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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2013-07-22 19:51:28 UTC
Update Date2023-02-21 17:30:20 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; which is mediated 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; 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. Mycophenolate mofetil (MMF) (brand names CellCept, Myfortic) is an immunosuppressant and prodrug of mycophenolic acid, used extensively in transplant medicine. MMF is a less toxic alternative to azathioprine. 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.
Structure
Data?1677000620
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
Physiological effectNot Available
Disposition
Process
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
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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+130.85231661259
DarkChem[M-H]-125.87731661259
DeepCCS[M+H]+131.59430932474
DeepCCS[M-H]-128.37830932474
DeepCCS[M-2H]-165.1530932474
DeepCCS[M+Na]+140.34430932474
AllCCS[M+H]+130.932859911
AllCCS[M+H-H2O]+126.532859911
AllCCS[M+NH4]+135.032859911
AllCCS[M+Na]+136.232859911
AllCCS[M-H]-129.632859911
AllCCS[M+Na-2H]-131.532859911
AllCCS[M+HCOO]-133.632859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
N-(2-Carboxymethyl)-morpholineOC(=O)CN1CCOCC11918.7Standard polar33892256
N-(2-Carboxymethyl)-morpholineOC(=O)CN1CCOCC11230.3Standard non polar33892256
N-(2-Carboxymethyl)-morpholineOC(=O)CN1CCOCC11333.6Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
N-(2-Carboxymethyl)-morpholine,1TMS,isomer #1C[Si](C)(C)OC(=O)CN1CCOCC11313.8Semi standard non polar33892256
N-(2-Carboxymethyl)-morpholine,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)CN1CCOCC11565.0Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - N-(2-Carboxymethyl)-morpholine GC-MS (Non-derivatized) - 70eV, Positivesplash10-0f6x-9300000000-f93563d3d3c0b79c65962017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - N-(2-Carboxymethyl)-morpholine GC-MS (1 TMS) - 70eV, Positivesplash10-0uk9-7900000000-6bc3cdc425e644b0801b2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - N-(2-Carboxymethyl)-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-Carboxymethyl)-morpholine 10V, Positive-QTOFsplash10-0udj-0900000000-09c0da4638317879a7cd2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-(2-Carboxymethyl)-morpholine 20V, Positive-QTOFsplash10-0udi-0900000000-c572fa66c2a7d7f26baa2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-(2-Carboxymethyl)-morpholine 40V, Positive-QTOFsplash10-0kfx-9100000000-6b84eedcb41995fbd2b62017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-(2-Carboxymethyl)-morpholine 10V, Negative-QTOFsplash10-0006-0900000000-c37c70455dd0f3ef9fdd2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-(2-Carboxymethyl)-morpholine 20V, Negative-QTOFsplash10-0f6x-0900000000-e6e119a3b2b58f2dda352017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-(2-Carboxymethyl)-morpholine 40V, Negative-QTOFsplash10-006x-9100000000-473c748012f7df687eae2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-(2-Carboxymethyl)-morpholine 10V, Positive-QTOFsplash10-0udi-0900000000-35b061a12fcfca3b02442021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-(2-Carboxymethyl)-morpholine 20V, Positive-QTOFsplash10-0udi-1900000000-4dbcc8a72d529d3fb16a2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-(2-Carboxymethyl)-morpholine 40V, Positive-QTOFsplash10-0a4i-9000000000-1f8c24d2abf9b963caf92021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-(2-Carboxymethyl)-morpholine 10V, Negative-QTOFsplash10-0006-0900000000-929838d02e588bff2e2c2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-(2-Carboxymethyl)-morpholine 20V, Negative-QTOFsplash10-0f6t-9700000000-0214e669f944d9f85e052021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-(2-Carboxymethyl)-morpholine 40V, Negative-QTOFsplash10-0006-9000000000-26cb7142e06fb32c8cbf2021-09-24Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 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, 1000 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, 200 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, 300 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, 400 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, 500 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, 600 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, 700 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, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)2023-02-04FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-04FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-04FELIX 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 Compound438968
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 ReferencesNot Available