Jump To Section:

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

Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-10 23:41:45 UTC

Update Date

2022-09-22 17:45:00 UTC

HMDB ID

HMDB0246678

Secondary Accession Numbers

None

Metabolite Identification

Common Name

2-(N-Morpholino)-ethanesulfonic acid

Description

2-(N-Morpholino)-ethanesulfonic acid, also known as 2-(N-morpholino)aethansulfonsaeure or 4-morpholineethanesulphonate, 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. Based on a literature review a significant number of articles have been published on 2-(N-Morpholino)-ethanesulfonic acid. This compound has been identified in human blood as reported by (PMID: 31557052 ). 2-(n-morpholino)-ethanesulfonic acid is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically 2-(N-Morpholino)-ethanesulfonic acid is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

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

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0       0.000   7.700   0.000  0.00  0.00           O-1
HETATM    2  S   UNK     0       0.000   6.160   0.000  0.00  0.00           S+0
HETATM    3  O   UNK     0      -1.540   6.160   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       1.540   6.160   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0       1.334   2.310   0.000  0.00  0.00           N+1
HETATM    8  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4    5                                             
CONECT    3    2                                                            
CONECT    4    2                                                            
CONECT    5    2    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   12                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11    7                                                       
MASTER        0    0    0    0    0    0    0    0   12    0   24    0
END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
2-(4-Morpholinyl)ethanesulfonic acid	ChEBI
2-(Morpholin-4-yl)ethanesulfonic acid	ChEBI
2-(N-Morpholino)aethansulfonsaeure	ChEBI
2-(N-Morpholino)ethansulfonsaeure	ChEBI
2-Morpholinoethanesulphonic acid	ChEBI
4-Morpholineethanesulfonic acid	ChEBI
4-Morpholinethanesulfonic acid	ChEBI
MES	ChEBI
2-(4-Morpholinyl)ethanesulfonate	Generator
2-(4-Morpholinyl)ethanesulphonate	Generator
2-(4-Morpholinyl)ethanesulphonic acid	Generator
2-(Morpholin-4-yl)ethanesulfonate	Generator
2-(Morpholin-4-yl)ethanesulphonate	Generator
2-(Morpholin-4-yl)ethanesulphonic acid	Generator
2-(N-Morpholino)aethansulphonsaeure	Generator
2-(N-Morpholino)ethansulphonsaeure	Generator
2-Morpholinoethanesulfonate	Generator
2-Morpholinoethanesulfonic acid	Generator
2-Morpholinoethanesulphonate	Generator
4-Morpholineethanesulfonate	Generator
4-Morpholineethanesulphonate	Generator
4-Morpholineethanesulphonic acid	Generator
4-Morpholinethanesulfonate	Generator
4-Morpholinethanesulphonate	Generator
4-Morpholinethanesulphonic acid	Generator
2-(N-Morpholino)-ethanesulfonate	Generator
2-(N-Morpholino)-ethanesulphonate	Generator
2-(N-Morpholino)-ethanesulphonic acid	Generator
2-(N-Morpholino)ethanesulfonate	HMDB
2-(N-Morpholino)ethanesulphonate	HMDB
2-(N-Morpholino)ethanesulphonic acid	HMDB
2-(N-Morpholino)ethanesulfonic acid, sodium salt	HMDB
2-(N-Morpholino)ethanesulfonic acid	HMDB
MES compound	HMDB

Chemical Formula

C₆H₁₃NO₄S

Average Molecular Weight

195.237

Monoisotopic Molecular Weight

195.056528599

IUPAC Name

4-(2-sulfonatoethyl)morpholin-4-ium

Traditional Name

4-(2-sulfonatoethyl)morpholin-4-ium

CAS Registry Number

Not Available

SMILES

[O-]S(=O)(=O)CC[NH+]1CCOCC1

InChI Identifier

InChI=1S/C6H13NO4S/c8-12(9,10)6-3-7-1-4-11-5-2-7/h1-6H2,(H,8,9,10)

InChI Key

SXGZJKUKBWWHRA-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
Organic sulfonic acid or derivatives
Organosulfonic acid or derivatives
Organosulfonic acid
Sulfonyl
Alkanesulfonic acid
Tertiary amine
Tertiary aliphatic amine
Dialkyl ether
Ether
Oxacycle
Azacycle
Organopnictogen compound
Organic oxygen compound
Organosulfur compound
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Organic oxide
Hydrocarbon derivative
Amine
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

organosulfonic acid (CHEBI:39005 )
MES (CHEBI:39005 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (PMID: 31557052)

Process

Not Available

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
logP	-0.87	ALOGPS
logP	-2.5	ChemAxon
logS	-1.7	ALOGPS
pKa (Strongest Acidic)	-1.5	ChemAxon
pKa (Strongest Basic)	6.51	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	70.87 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	53.64 m³·mol⁻¹	ChemAxon
Polarizability	18.67 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
DeepCCS	[M+H]+	131.625	30932474
DeepCCS	[M-H]-	129.228	30932474
DeepCCS	[M-2H]-	164.083	30932474
DeepCCS	[M+Na]+	138.542	30932474
AllCCS	[M+H]+	138.3	32859911
AllCCS	[M+H-H2O]+	134.4	32859911
AllCCS	[M+NH4]+	142.0	32859911
AllCCS	[M+Na]+	143.1	32859911
AllCCS	[M-H]-	135.7	32859911
AllCCS	[M+Na-2H]-	136.8	32859911
AllCCS	[M+HCOO]-	138.1	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Predicted by Siyang on May 30, 2022	8.8195 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	6.98 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	699.4 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	262.3 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	93.0 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	168.0 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	52.1 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	217.3 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	255.3 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	650.6 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	609.0 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	74.0 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	898.1 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	182.9 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	173.6 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	526.6 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	302.7 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	203.5 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
2-(N-Morpholino)-ethanesulfonic acid	[O-]S(=O)(=O)CC[NH+]1CCOCC1	2620.9	Standard polar	33892256
2-(N-Morpholino)-ethanesulfonic acid	[O-]S(=O)(=O)CC[NH+]1CCOCC1	1462.9	Standard non polar	33892256
2-(N-Morpholino)-ethanesulfonic acid	[O-]S(=O)(=O)CC[NH+]1CCOCC1	1613.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
2-(N-Morpholino)-ethanesulfonic acid,1TMS,isomer #1	C[Si](C)(C)[N+]1(CCS(=O)(=O)[O-])CCOCC1	1759.1	Semi standard non polar	33892256
2-(N-Morpholino)-ethanesulfonic acid,1TMS,isomer #1	C[Si](C)(C)[N+]1(CCS(=O)(=O)[O-])CCOCC1	1782.7	Standard non polar	33892256
2-(N-Morpholino)-ethanesulfonic acid,1TMS,isomer #1	C[Si](C)(C)[N+]1(CCS(=O)(=O)[O-])CCOCC1	2554.0	Standard polar	33892256
2-(N-Morpholino)-ethanesulfonic acid,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)[N+]1(CCS(=O)(=O)[O-])CCOCC1	1988.4	Semi standard non polar	33892256
2-(N-Morpholino)-ethanesulfonic acid,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)[N+]1(CCS(=O)(=O)[O-])CCOCC1	2077.3	Standard non polar	33892256
2-(N-Morpholino)-ethanesulfonic acid,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)[N+]1(CCS(=O)(=O)[O-])CCOCC1	2785.1	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 2-(N-Morpholino)-ethanesulfonic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-0nvl-9400000000-28f4e362c9075f85012c	2017-08-28	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-(N-Morpholino)-ethanesulfonic acid 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 - 2-(N-Morpholino)-ethanesulfonic acid 10V, Positive-QTOF	splash10-0002-0900000000-7cc87e0205c077ce542a	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-(N-Morpholino)-ethanesulfonic acid 20V, Positive-QTOF	splash10-0m02-1900000000-89153a2145972e7467bf	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-(N-Morpholino)-ethanesulfonic acid 40V, Positive-QTOF	splash10-052u-9200000000-183d2f383e64c67c8960	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-(N-Morpholino)-ethanesulfonic acid 10V, Negative-QTOF	splash10-0006-2900000000-efa87cbabd9646414d4a	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-(N-Morpholino)-ethanesulfonic acid 20V, Negative-QTOF	splash10-000x-8900000000-9316e4235b5d691b3622	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-(N-Morpholino)-ethanesulfonic acid 40V, Negative-QTOF	splash10-001i-9200000000-1fe336286663608bd7fe	2017-07-26	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	details
Urine	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	34436864	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB03814

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

70541

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

MES_(buffer)

METLIN ID

Not Available

PubChem Compound

78165

PDB ID

Not Available

ChEBI ID

39005

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

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for 2-(N-Morpholino)-ethanesulfonic acid (HMDB0246678)

MOL for HMDB0246678 (2-(N-Morpholino)-ethanesulfonic acid)

3D MOL for HMDB0246678 (2-(N-Morpholino)-ethanesulfonic acid)

3D SDF for HMDB0246678 (2-(N-Morpholino)-ethanesulfonic acid)

3D-SDF for HMDB0246678 (2-(N-Morpholino)-ethanesulfonic acid)

PDB for HMDB0246678 (2-(N-Morpholino)-ethanesulfonic acid)

3D PDB for HMDB0246678 (2-(N-Morpholino)-ethanesulfonic acid)

SMILES for HMDB0246678 (2-(N-Morpholino)-ethanesulfonic acid)

INCHI for HMDB0246678 (2-(N-Morpholino)-ethanesulfonic acid)

Structure for HMDB0246678 (2-(N-Morpholino)-ethanesulfonic acid)

3D Structure for HMDB0246678 (2-(N-Morpholino)-ethanesulfonic acid)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra