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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2013-06-15 18:25:46 UTC

Update Date

2023-02-21 17:30:07 UTC

HMDB ID

HMDB0060650

Secondary Accession Numbers

HMDB60650

Metabolite Identification

Common Name

N-(2-Hydroxyethyl)-morpholine

Description

N-(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

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
2-(4-Morpholinyl)ethanol	ChEBI
4-(2-Hydroxyethyl)morpholine	ChEBI
4-Morpholineethanol	ChEBI
Hydroxyethylmorpholine	ChEBI
Morpholine ethanol	ChEBI
N(2-Hydroxyethyl)morpholine	ChEBI
N-beta-Hydroxyethylmorpholine	ChEBI
N-b-Hydroxyethylmorpholine	Generator
N-Β-hydroxyethylmorpholine	Generator

Chemical Formula

C₆H₁₃NO₂

Average Molecular Weight

131.1729

Monoisotopic Molecular Weight

131.094628665

IUPAC Name

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

Traditional Name

4-morpholineethanol

CAS Registry Number

Not Available

SMILES

OCCN1CCOCC1

InChI Identifier

InChI=1S/C6H13NO2/c8-4-1-7-2-5-9-6-3-7/h8H,1-6H2

InChI Key

KKFDCBRMNNSAAW-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
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 Framework

Aliphatic heteromonocyclic compounds

External Descriptors

tertiary amino compound (CHEBI:67144 )
primary alcohol (CHEBI:67144 )
morpholines (CHEBI:67144 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0060650)

Organ

Kidney (HMDB: HMDB0060650)
Liver (HMDB: HMDB0060650)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0060650)

Cellular substructure

Cytoplasm (HMDB: HMDB0060650)

Source

Endogenous

Endogenous (HMDB: HMDB0060650)

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	1110 g/L	ALOGPS
logP	-0.58	ALOGPS
logP	-0.72	ChemAxon
logS	0.93	ALOGPS
pKa (Strongest Acidic)	15.59	ChemAxon
pKa (Strongest Basic)	7.19	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	32.7 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	35.35 m³·mol⁻¹	ChemAxon
Polarizability	14.4 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	126.231	31661259
DarkChem	[M-H]-	120.835	31661259
DeepCCS	[M+H]+	130.888	30932474
DeepCCS	[M-H]-	128.203	30932474
DeepCCS	[M-2H]-	164.626	30932474
DeepCCS	[M+Na]+	139.464	30932474
AllCCS	[M+H]+	128.6	32859911
AllCCS	[M+H-H2O]+	124.0	32859911
AllCCS	[M+NH4]+	132.8	32859911
AllCCS	[M+Na]+	134.0	32859911
AllCCS	[M-H]-	128.7	32859911
AllCCS	[M+Na-2H]-	131.0	32859911
AllCCS	[M+HCOO]-	133.7	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	1.22 minutes	32390414
Predicted by Siyang on May 30, 2022	8.2456 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	5.67 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	395.2 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	265.3 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	71.1 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	171.9 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	45.5 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	256.1 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	235.4 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	728.7 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	556.6 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	39.5 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	605.5 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	177.6 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	203.0 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	676.9 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	481.5 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	300.0 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
N-(2-Hydroxyethyl)-morpholine	OCCN1CCOCC1	1840.1	Standard polar	33892256
N-(2-Hydroxyethyl)-morpholine	OCCN1CCOCC1	1113.8	Standard non polar	33892256
N-(2-Hydroxyethyl)-morpholine	OCCN1CCOCC1	1118.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
N-(2-Hydroxyethyl)-morpholine,1TMS,isomer #1	C[Si](C)(C)OCCN1CCOCC1	1250.0	Semi standard non polar	33892256
N-(2-Hydroxyethyl)-morpholine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OCCN1CCOCC1	1474.6	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 GC-MS (Non-derivatized) - 70eV, Positive	splash10-0udr-9300000000-a428bf4121b4d2205aeb	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-(2-Hydroxyethyl)-morpholine GC-MS (1 TMS) - 70eV, Positive	splash10-0udr-7900000000-76434aaf20aeff698ca6	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-(2-Hydroxyethyl)-morpholine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-(2-Hydroxyethyl)-morpholine 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 10V, Positive-QTOF	splash10-001i-0900000000-f187a9992ab2eee6260c	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-(2-Hydroxyethyl)-morpholine 20V, Positive-QTOF	splash10-03e9-2900000000-a0b8a40fe23c332b3699	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-(2-Hydroxyethyl)-morpholine 40V, Positive-QTOF	splash10-052v-9100000000-ba9841aa75800c9c54cd	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-(2-Hydroxyethyl)-morpholine 10V, Negative-QTOF	splash10-001i-1900000000-44fbfc21ff1e48a3d6f1	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-(2-Hydroxyethyl)-morpholine 20V, Negative-QTOF	splash10-001i-3900000000-07561feaf57473965bc6	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-(2-Hydroxyethyl)-morpholine 40V, Negative-QTOF	splash10-052f-9000000000-2032f99671dad68f2d8a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-(2-Hydroxyethyl)-morpholine 10V, Positive-QTOF	splash10-03e9-0900000000-79beccd31ed773887abc	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-(2-Hydroxyethyl)-morpholine 20V, Positive-QTOF	splash10-0ik9-1900000000-53c62a4955a59f5d5707	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-(2-Hydroxyethyl)-morpholine 40V, Positive-QTOF	splash10-01vk-9300000000-8a1d8096462abddc74da	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-(2-Hydroxyethyl)-morpholine 10V, Negative-QTOF	splash10-001i-1900000000-2df8658716f49b191fca	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-(2-Hydroxyethyl)-morpholine 20V, Negative-QTOF	splash10-0gvp-9600000000-d8b093f22240665ef493	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-(2-Hydroxyethyl)-morpholine 40V, Negative-QTOF	splash10-0006-9000000000-a93051099d4f052862fa	2021-10-12	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
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, 100 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, 1000 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, 200 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, 300 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, 400 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, 500 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, 600 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, 700 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, 800 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
Predicted 1D NMR	¹H 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

61163

PDB ID

Not Available

ChEBI ID

67144

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 (HMDB0060650)

MOL for HMDB0060650 (N-(2-Hydroxyethyl)-morpholine)

3D MOL for HMDB0060650 (N-(2-Hydroxyethyl)-morpholine)

3D SDF for HMDB0060650 (N-(2-Hydroxyethyl)-morpholine)

3D-SDF for HMDB0060650 (N-(2-Hydroxyethyl)-morpholine)

PDB for HMDB0060650 (N-(2-Hydroxyethyl)-morpholine)

3D PDB for HMDB0060650 (N-(2-Hydroxyethyl)-morpholine)

SMILES for HMDB0060650 (N-(2-Hydroxyethyl)-morpholine)

INCHI for HMDB0060650 (N-(2-Hydroxyethyl)-morpholine)

Structure for HMDB0060650 (N-(2-Hydroxyethyl)-morpholine)

3D Structure for HMDB0060650 (N-(2-Hydroxyethyl)-morpholine)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra