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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2013-04-09 21:19:41 UTC

Update Date

2023-02-21 17:29:40 UTC

HMDB ID

HMDB0060013

Secondary Accession Numbers

HMDB60013

Metabolite Identification

Common Name

O-methoxycatechol-O-sulphate

Description

O-methoxycatechol-O-sulphate, also known as 2-methoxyphenyl sulfate or O-methylcatechol sulfuric acid, belongs to the class of organic compounds known as phenylsulfates. Phenylsulfates are compounds containing a sulfuric acid group conjugated to a phenyl group. O-methoxycatechol-O-sulphate is an extremely weak basic (essentially neutral) compound (based on its pKa). An aryl sulfate that is catechol in which the two phenolic hydrogens are replaced by methyl and sulfo groups.

Structure

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

HEADER    PROTEIN                                 12-SEP-17   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-SEP-17         0                                  
HETATM    1  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
HETATM   10  S   UNK     0      -2.667   1.540   0.000  0.00  0.00           S+0
HETATM   11  O   UNK     0      -4.001   0.770   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      -3.437   2.874   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      -1.897   0.206   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    8                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    3    9                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   12   13                                             
CONECT   11   10                                                            
CONECT   12   10                                                            
CONECT   13   10                                                            
MASTER        0    0    0    0    0    0    0    0   13    0   26    0
END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
2-Methoxyphenyl sulfate	ChEBI
O-Methoxyphenyl hydrogen sulfate	ChEBI
O-Methoxyphenyl sulfate	ChEBI
O-Methylcatechol hydrogen sulfate	ChEBI
O-Methylcatechol sulfate	ChEBI
2-Methoxyphenyl sulfuric acid	Generator
2-Methoxyphenyl sulphate	Generator
2-Methoxyphenyl sulphuric acid	Generator
O-Methoxyphenyl hydrogen sulfuric acid	Generator
O-Methoxyphenyl hydrogen sulphate	Generator
O-Methoxyphenyl hydrogen sulphuric acid	Generator
O-Methoxyphenyl sulfuric acid	Generator
O-Methoxyphenyl sulphate	Generator
O-Methoxyphenyl sulphuric acid	Generator
O-Methylcatechol hydrogen sulfuric acid	Generator
O-Methylcatechol hydrogen sulphate	Generator
O-Methylcatechol hydrogen sulphuric acid	Generator
O-Methylcatechol sulfuric acid	Generator
O-Methylcatechol sulphate	Generator
O-Methylcatechol sulphuric acid	Generator
O-Methoxycatechol-O-sulfate	Generator
O-Methoxycatechol-O-sulfuric acid	Generator
O-Methoxycatechol-O-sulphuric acid	Generator
Guaiacol sulfuric acid	HMDB
Guaiacol sulphate	HMDB
Guaiacol sulphuric acid	HMDB

Chemical Formula

C₇H₈O₅S

Average Molecular Weight

204.2

Monoisotopic Molecular Weight

204.009244056

IUPAC Name

(2-methoxyphenyl)oxidanesulfonic acid

Traditional Name

(2-methoxyphenyl)oxidanesulfonic acid

CAS Registry Number

Not Available

SMILES

COC1=CC=CC=C1OS(O)(=O)=O

InChI Identifier

InChI=1S/C7H8O5S/c1-11-6-4-2-3-5-7(6)12-13(8,9)10/h2-5H,1H3,(H,8,9,10)

InChI Key

AQTYXAPIHMXAAV-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenylsulfates. Phenylsulfates are compounds containing a sulfuric acid group conjugated to a phenyl group.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Organic sulfuric acids and derivatives

Sub Class

Arylsulfates

Direct Parent

Phenylsulfates

Alternative Parents

Substituents

Phenylsulfate
Phenoxy compound
Anisole
Phenol ether
Methoxybenzene
Alkyl aryl ether
Monocyclic benzene moiety
Benzenoid
Sulfuric acid monoester
Sulfate-ester
Sulfuric acid ester
Ether
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Urine (PMID: 22827565)

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
Water Solubility	2.09 g/L	ALOGPS
logP	-0.6	ALOGPS
logP	1.04	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	-2.3	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	72.83 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	44.49 m³·mol⁻¹	ChemAxon
Polarizability	17.79 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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]+	144.888	31661259
DarkChem	[M-H]-	142.786	31661259
DeepCCS	[M+H]+	137.168	30932474
DeepCCS	[M-H]-	133.34	30932474
DeepCCS	[M-2H]-	170.736	30932474
DeepCCS	[M+Na]+	146.275	30932474
AllCCS	[M+H]+	143.7	32859911
AllCCS	[M+H-H2O]+	139.6	32859911
AllCCS	[M+NH4]+	147.6	32859911
AllCCS	[M+Na]+	148.7	32859911
AllCCS	[M-H]-	135.9	32859911
AllCCS	[M+Na-2H]-	136.8	32859911
AllCCS	[M+HCOO]-	137.8	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
O-methoxycatechol-O-sulphate	COC1=CC=CC=C1OS(O)(=O)=O	2775.4	Standard polar	33892256
O-methoxycatechol-O-sulphate	COC1=CC=CC=C1OS(O)(=O)=O	1515.3	Standard non polar	33892256
O-methoxycatechol-O-sulphate	COC1=CC=CC=C1OS(O)(=O)=O	1691.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
O-methoxycatechol-O-sulphate,1TMS,isomer #1	COC1=CC=CC=C1OS(=O)(=O)O[Si](C)(C)C	1661.7	Semi standard non polar	33892256
O-methoxycatechol-O-sulphate,1TMS,isomer #1	COC1=CC=CC=C1OS(=O)(=O)O[Si](C)(C)C	1705.0	Standard non polar	33892256
O-methoxycatechol-O-sulphate,1TMS,isomer #1	COC1=CC=CC=C1OS(=O)(=O)O[Si](C)(C)C	2493.7	Standard polar	33892256
O-methoxycatechol-O-sulphate,1TBDMS,isomer #1	COC1=CC=CC=C1OS(=O)(=O)O[Si](C)(C)C(C)(C)C	1903.0	Semi standard non polar	33892256
O-methoxycatechol-O-sulphate,1TBDMS,isomer #1	COC1=CC=CC=C1OS(=O)(=O)O[Si](C)(C)C(C)(C)C	1970.5	Standard non polar	33892256
O-methoxycatechol-O-sulphate,1TBDMS,isomer #1	COC1=CC=CC=C1OS(=O)(=O)O[Si](C)(C)C(C)(C)C	2550.7	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - O-methoxycatechol-O-sulphate GC-MS (Non-derivatized) - 70eV, Positive	splash10-0fk9-5920000000-752b39d4a8801b2f55a5	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - O-methoxycatechol-O-sulphate 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
Experimental LC-MS/MS	LC-MS/MS Spectrum - O-methoxycatechol-O-sulphate 30V, Negative-QTOF	splash10-0a4i-0900000000-55dcc608af0037906ab3	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - O-methoxycatechol-O-sulphate 10V, Negative-QTOF	splash10-0udi-0390000000-28a0f2e4f90e35ac55a1	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - O-methoxycatechol-O-sulphate 10V, Positive-QTOF	splash10-0a4i-0290000000-7860e9604560df9580c4	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - O-methoxycatechol-O-sulphate 20V, Positive-QTOF	splash10-0a70-0920000000-02830b32dc1e2f73e9fd	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - O-methoxycatechol-O-sulphate 40V, Positive-QTOF	splash10-0udi-9000000000-ca2b18a86013204d151b	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - O-methoxycatechol-O-sulphate 10V, Negative-QTOF	splash10-0udi-0090000000-275a3d5e7793f6dde7fc	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - O-methoxycatechol-O-sulphate 20V, Negative-QTOF	splash10-0kmi-1930000000-f1d560df0292dbb9edc4	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - O-methoxycatechol-O-sulphate 40V, Negative-QTOF	splash10-0a4i-6900000000-a9783124b34914687fb2	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - O-methoxycatechol-O-sulphate 10V, Positive-QTOF	splash10-0a6r-0960000000-64a7410131d0662273f0	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - O-methoxycatechol-O-sulphate 20V, Positive-QTOF	splash10-056s-5900000000-836176cdd31df5ecb53f	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - O-methoxycatechol-O-sulphate 40V, Positive-QTOF	splash10-0kmi-6900000000-5f28170f45c405290ab3	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - O-methoxycatechol-O-sulphate 10V, Negative-QTOF	splash10-0udi-0090000000-ca2df71642be8b8709e3	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - O-methoxycatechol-O-sulphate 20V, Negative-QTOF	splash10-0002-9210000000-44abe55c81c5a31cd536	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - O-methoxycatechol-O-sulphate 40V, Negative-QTOF	splash10-0002-9000000000-9efcbb4cb28fc520a20a	2021-10-12	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

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
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22827565	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Cancer patients undergoing total body irradiation	31424920	details

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

22473

PDB ID

Not Available

ChEBI ID

133460

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

van der Hooft JJ, de Vos RC, Mihaleva V, Bino RJ, Ridder L, de Roo N, Jacobs DM, van Duynhoven JP, Vervoort J: Structural elucidation and quantification of phenolic conjugates present in human urine after tea intake. Anal Chem. 2012 Aug 21;84(16):7263-71. doi: 10.1021/ac3017339. Epub 2012 Aug 2. [PubMed:22827565 ]

Showing metabocard for O-methoxycatechol-O-sulphate (HMDB0060013)

MOL for HMDB0060013 (O-methoxycatechol-O-sulphate)

3D MOL for HMDB0060013 (O-methoxycatechol-O-sulphate)

3D SDF for HMDB0060013 (O-methoxycatechol-O-sulphate)

3D-SDF for HMDB0060013 (O-methoxycatechol-O-sulphate)

PDB for HMDB0060013 (O-methoxycatechol-O-sulphate)

3D PDB for HMDB0060013 (O-methoxycatechol-O-sulphate)

SMILES for HMDB0060013 (O-methoxycatechol-O-sulphate)

INCHI for HMDB0060013 (O-methoxycatechol-O-sulphate)

Structure for HMDB0060013 (O-methoxycatechol-O-sulphate)

3D Structure for HMDB0060013 (O-methoxycatechol-O-sulphate)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra