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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2013-07-22 19:51:31 UTC

Update Date

2023-02-21 17:30:21 UTC

HMDB ID

HMDB0061157

Secondary Accession Numbers

HMDB61157

Metabolite Identification

Common Name

N-(2-Hydroxyethyl)-morpholine N-oxide

Description

N-(2-Hydroxyethyl)-morpholine N-oxide 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 N-oxide is a metabolite of mycophenolate mofetil. N-(2-Hydroxyethyl)-morpholine N-oxide is an extremely weak basic (essentially neutral) compound (based on its pKa). Within humans, N-(2-hydroxyethyl)-morpholine N-oxide 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 catalyzed by the enzymes liver carboxylesterase 1 and cocaine esterase. In humans, N-(2-hydroxyethyl)-morpholine N-oxide is involved in mycophenolic acid metabolism pathway. 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. 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.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₆H₁₃NO₃

Average Molecular Weight

147.1723

Monoisotopic Molecular Weight

147.089543287

IUPAC Name

2-(morpholin-4-yloxy)ethan-1-ol

Traditional Name

2-(morpholin-4-yloxy)ethanol

CAS Registry Number

Not Available

SMILES

OCCON1CCOCC1

InChI Identifier

InChI=1S/C6H13NO3/c8-3-6-10-7-1-4-9-5-2-7/h8H,1-6H2

InChI Key

WTPGFRPRHSDKNE-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.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Oxazinanes

Sub Class

Morpholines

Direct Parent

Morpholines

Alternative Parents

Substituents

Morpholine
Oxacycle
Azacycle
N-organohydroxylamine
Ether
Dialkyl ether
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Organonitrogen compound
Alcohol
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Cytoplasm (HMDB: HMDB0061157)

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0061157)

Organ

Liver (HMDB: HMDB0061157)
Kidney (HMDB: HMDB0061157)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0061157)

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Mycophenolic Acid Metabolism Pathway (PathBank: SMP0000652)

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	883 g/L	ALOGPS
logP	-0.66	ALOGPS
logP	-1.1	ChemAxon
logS	0.78	ALOGPS
pKa (Strongest Acidic)	15.05	ChemAxon
pKa (Strongest Basic)	0.28	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	41.93 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	36.31 m³·mol⁻¹	ChemAxon
Polarizability	15.36 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	130.272	31661259
DarkChem	[M-H]-	124.772	31661259
DeepCCS	[M+H]+	131.714	30932474
DeepCCS	[M-H]-	129.003	30932474
DeepCCS	[M-2H]-	165.47	30932474
DeepCCS	[M+Na]+	140.422	30932474
AllCCS	[M+H]+	132.1	32859911
AllCCS	[M+H-H2O]+	127.7	32859911
AllCCS	[M+NH4]+	136.2	32859911
AllCCS	[M+Na]+	137.4	32859911
AllCCS	[M-H]-	132.0	32859911
AllCCS	[M+Na-2H]-	133.9	32859911
AllCCS	[M+HCOO]-	136.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
N-(2-Hydroxyethyl)-morpholine N-oxide	OCCON1CCOCC1	1726.3	Standard polar	33892256
N-(2-Hydroxyethyl)-morpholine N-oxide	OCCON1CCOCC1	1184.8	Standard non polar	33892256
N-(2-Hydroxyethyl)-morpholine N-oxide	OCCON1CCOCC1	1201.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
N-(2-Hydroxyethyl)-morpholine N-oxide,1TMS,isomer #1	C[Si](C)(C)OCCON1CCOCC1	1348.9	Semi standard non polar	33892256
N-(2-Hydroxyethyl)-morpholine N-oxide,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OCCON1CCOCC1	1592.7	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - N-(2-Hydroxyethyl)-morpholine N-oxide GC-MS (Non-derivatized) - 70eV, Positive	splash10-0v0d-9400000000-9aa2d0c0587c2d2a8589	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-(2-Hydroxyethyl)-morpholine N-oxide GC-MS (1 TMS) - 70eV, Positive	splash10-00y0-9400000000-1232d9adaa8d939b8765	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-(2-Hydroxyethyl)-morpholine N-oxide GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-(2-Hydroxyethyl)-morpholine N-oxide 10V, Negative-QTOF	splash10-0002-0900000000-b5d658e0c27937ce102e	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-(2-Hydroxyethyl)-morpholine N-oxide 20V, Negative-QTOF	splash10-001r-9300000000-fd8a8858f4828a642271	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-(2-Hydroxyethyl)-morpholine N-oxide 40V, Negative-QTOF	splash10-0lxx-9000000000-4fafb29a2fafb19e6fdd	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-(2-Hydroxyethyl)-morpholine N-oxide 10V, Negative-QTOF	splash10-0536-9100000000-df6e89da756ee70edf1c	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-(2-Hydroxyethyl)-morpholine N-oxide 20V, Negative-QTOF	splash10-0kal-9200000000-7480bc90daff07d93f12	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-(2-Hydroxyethyl)-morpholine N-oxide 40V, Negative-QTOF	splash10-0006-9000000000-1ec5c673573a565076bc	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-(2-Hydroxyethyl)-morpholine N-oxide 10V, Positive-QTOF	splash10-0002-4900000000-32c50caccc3690ac873f	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-(2-Hydroxyethyl)-morpholine N-oxide 20V, Positive-QTOF	splash10-0002-9400000000-b41c87503429dc9b3439	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-(2-Hydroxyethyl)-morpholine N-oxide 40V, Positive-QTOF	splash10-0002-9000000000-b31b60e8e610b7c072bf	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-(2-Hydroxyethyl)-morpholine N-oxide 10V, Positive-QTOF	splash10-0f6t-2900000000-2602f24afbf6ed64633c	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-(2-Hydroxyethyl)-morpholine N-oxide 20V, Positive-QTOF	splash10-0f81-7900000000-11ff07b71daeb1e47e06	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-(2-Hydroxyethyl)-morpholine N-oxide 40V, Positive-QTOF	splash10-06r2-9100000000-0528e0a8fbedcbceaefd	2021-09-22	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-04	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm

Biospecimen Locations

Blood
Urine

Tissue Locations

Kidney
Liver

Pathways

Name	SMPDB/PathBank	KEGG
Mycophenolic Acid Metabolism Pathway		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Normal	Not Available	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Normal	Not Available	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

130392110

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Showing metabocard for N-(2-Hydroxyethyl)-morpholine N-oxide (HMDB0061157)

MOL for HMDB0061157 (N-(2-Hydroxyethyl)-morpholine N-oxide)

3D MOL for HMDB0061157 (N-(2-Hydroxyethyl)-morpholine N-oxide)

3D SDF for HMDB0061157 (N-(2-Hydroxyethyl)-morpholine N-oxide)

3D-SDF for HMDB0061157 (N-(2-Hydroxyethyl)-morpholine N-oxide)

PDB for HMDB0061157 (N-(2-Hydroxyethyl)-morpholine N-oxide)

3D PDB for HMDB0061157 (N-(2-Hydroxyethyl)-morpholine N-oxide)

SMILES for HMDB0061157 (N-(2-Hydroxyethyl)-morpholine N-oxide)

INCHI for HMDB0061157 (N-(2-Hydroxyethyl)-morpholine N-oxide)

Structure for HMDB0061157 (N-(2-Hydroxyethyl)-morpholine N-oxide)

3D Structure for HMDB0061157 (N-(2-Hydroxyethyl)-morpholine N-oxide)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra