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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2013-07-22 19:51:28 UTC

Update Date

2023-02-21 17:30:20 UTC

HMDB ID

HMDB0061156

Secondary Accession Numbers

HMDB61156

Metabolite Identification

Common Name

N-(2-Carboxymethyl)-morpholine

Description

N-(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

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

C₆H₁₁NO₃

Average Molecular Weight

145.1564

Monoisotopic Molecular Weight

145.073893223

IUPAC Name

2-(morpholin-4-yl)acetic acid

Traditional Name

morpholin-4-ylacetic acid

CAS Registry Number

Not 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 Key

VIWZVFVJPXTXPA-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).

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Alpha 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 Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0061156)

Organ

Liver (HMDB: HMDB0061156)
Kidney (HMDB: HMDB0061156)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0061156)

Cellular substructure

Cytoplasm (HMDB: HMDB0061156)

Source

Endogenous

Endogenous (HMDB: HMDB0061156)

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	1040 g/L	ALOGPS
logP	-1.8	ALOGPS
logP	-2.7	ChemAxon
logS	0.85	ALOGPS
pKa (Strongest Acidic)	2.95	ChemAxon
pKa (Strongest Basic)	6.45	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	49.77 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	35.15 m³·mol⁻¹	ChemAxon
Polarizability	14.17 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]+	130.852	31661259
DarkChem	[M-H]-	125.877	31661259
DeepCCS	[M+H]+	131.594	30932474
DeepCCS	[M-H]-	128.378	30932474
DeepCCS	[M-2H]-	165.15	30932474
DeepCCS	[M+Na]+	140.344	30932474
AllCCS	[M+H]+	130.9	32859911
AllCCS	[M+H-H2O]+	126.5	32859911
AllCCS	[M+NH4]+	135.0	32859911
AllCCS	[M+Na]+	136.2	32859911
AllCCS	[M-H]-	129.6	32859911
AllCCS	[M+Na-2H]-	131.5	32859911
AllCCS	[M+HCOO]-	133.6	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.	1.2 minutes	32390414
Predicted by Siyang on May 30, 2022	8.7532 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	6.32 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	609.7 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	278.6 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	67.8 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	167.4 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	38.4 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	233.6 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	293.3 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	575.1 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	589.7 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	42.1 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	820.7 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	183.7 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	167.7 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	612.8 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	303.8 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	311.0 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
N-(2-Carboxymethyl)-morpholine	OC(=O)CN1CCOCC1	1918.7	Standard polar	33892256
N-(2-Carboxymethyl)-morpholine	OC(=O)CN1CCOCC1	1230.3	Standard non polar	33892256
N-(2-Carboxymethyl)-morpholine	OC(=O)CN1CCOCC1	1333.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
N-(2-Carboxymethyl)-morpholine,1TMS,isomer #1	C[Si](C)(C)OC(=O)CN1CCOCC1	1313.8	Semi standard non polar	33892256
N-(2-Carboxymethyl)-morpholine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CN1CCOCC1	1565.0	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-Carboxymethyl)-morpholine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0f6x-9300000000-f93563d3d3c0b79c6596	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-(2-Carboxymethyl)-morpholine GC-MS (1 TMS) - 70eV, Positive	splash10-0uk9-7900000000-6bc3cdc425e644b0801b	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-(2-Carboxymethyl)-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-Carboxymethyl)-morpholine 10V, Positive-QTOF	splash10-0udj-0900000000-09c0da4638317879a7cd	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-(2-Carboxymethyl)-morpholine 20V, Positive-QTOF	splash10-0udi-0900000000-c572fa66c2a7d7f26baa	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-(2-Carboxymethyl)-morpholine 40V, Positive-QTOF	splash10-0kfx-9100000000-6b84eedcb41995fbd2b6	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-(2-Carboxymethyl)-morpholine 10V, Negative-QTOF	splash10-0006-0900000000-c37c70455dd0f3ef9fdd	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-(2-Carboxymethyl)-morpholine 20V, Negative-QTOF	splash10-0f6x-0900000000-e6e119a3b2b58f2dda35	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-(2-Carboxymethyl)-morpholine 40V, Negative-QTOF	splash10-006x-9100000000-473c748012f7df687eae	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-(2-Carboxymethyl)-morpholine 10V, Positive-QTOF	splash10-0udi-0900000000-35b061a12fcfca3b0244	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-(2-Carboxymethyl)-morpholine 20V, Positive-QTOF	splash10-0udi-1900000000-4dbcc8a72d529d3fb16a	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-(2-Carboxymethyl)-morpholine 40V, Positive-QTOF	splash10-0a4i-9000000000-1f8c24d2abf9b963caf9	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-(2-Carboxymethyl)-morpholine 10V, Negative-QTOF	splash10-0006-0900000000-929838d02e588bff2e2c	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-(2-Carboxymethyl)-morpholine 20V, Negative-QTOF	splash10-0f6t-9700000000-0214e669f944d9f85e05	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-(2-Carboxymethyl)-morpholine 40V, Negative-QTOF	splash10-0006-9000000000-26cb7142e06fb32c8cbf	2021-09-24	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

438968

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-Carboxymethyl)-morpholine (HMDB0061156)

MOL for HMDB0061156 (N-(2-Carboxymethyl)-morpholine)

3D MOL for HMDB0061156 (N-(2-Carboxymethyl)-morpholine)

3D SDF for HMDB0061156 (N-(2-Carboxymethyl)-morpholine)

3D-SDF for HMDB0061156 (N-(2-Carboxymethyl)-morpholine)

PDB for HMDB0061156 (N-(2-Carboxymethyl)-morpholine)

3D PDB for HMDB0061156 (N-(2-Carboxymethyl)-morpholine)

SMILES for HMDB0061156 (N-(2-Carboxymethyl)-morpholine)

INCHI for HMDB0061156 (N-(2-Carboxymethyl)-morpholine)

Structure for HMDB0061156 (N-(2-Carboxymethyl)-morpholine)

3D Structure for HMDB0061156 (N-(2-Carboxymethyl)-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