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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2020-06-04 20:07:34 UTC

Update Date

2022-09-22 18:34:33 UTC

HMDB ID

HMDB0240655

Secondary Accession Numbers

None

Metabolite Identification

Common Name

o-Cresol sulfate

Description

o-cresol hydrogen sulfate, also known as O-cresolsulfuric acid or O-cresol sulphate, belongs to the class of organic compounds known as phenylsulfates. Phenylsulfates are compounds containing a sulfuric acid group conjugated to a phenyl group. Based on a literature review very few articles have been published on o-cresol hydrogen sulfate.

Structure

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

HEADER    PROTEIN                                 04-JUN-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-JUN-20         0                                  
HETATM    1  C   UNK     0    8669.3668668.160   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8668.0348667.390   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8666.7008668.160   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    8665.3668667.390   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0    8665.3668665.850   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    8666.7008665.080   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    8668.0348665.850   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0    8664.0418669.704   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0    8664.6038671.795   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0    8666.7008669.700   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0    8666.1348671.795   0.000  0.00  0.00           O+0
HETATM   12  S   UNK     0    8665.3678670.471   0.000  0.00  0.00           S+0
CONECT    1    2                                                            
CONECT    2    3    7    1                                                  
CONECT    3    2    4   10                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    2                                                       
CONECT    8   12                                                            
CONECT    9   12                                                            
CONECT   10   12    3                                                       
CONECT   11   12                                                            
CONECT   12   10    9   11    8                                             
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-Methylphenyl) sulfate	ChEBI
O-Cresol sulfate	ChEBI
O-Cresolsulfuric acid	ChEBI
O-Methylphenyl sulfate	ChEBI
O-Tolyl sulfate	ChEBI
Sulfuric acid, mono-O-tolyl ester	ChEBI
(2-Methylphenyl) sulfuric acid	Generator
(2-Methylphenyl) sulphate	Generator
(2-Methylphenyl) sulphuric acid	Generator
O-Cresol sulfuric acid	Generator
O-Cresol sulphate	Generator
O-Cresol sulphuric acid	Generator
O-Cresolsulfate	Generator
O-Cresolsulphate	Generator
O-Cresolsulphuric acid	Generator
O-Methylphenyl sulfuric acid	Generator
O-Methylphenyl sulphate	Generator
O-Methylphenyl sulphuric acid	Generator
O-Tolyl sulfuric acid	Generator
O-Tolyl sulphate	Generator
O-Tolyl sulphuric acid	Generator
Sulfate, mono-O-tolyl ester	Generator
Sulphate, mono-O-tolyl ester	Generator
Sulphuric acid, mono-O-tolyl ester	Generator
O-Cresol hydrogen sulfuric acid	Generator
O-Cresol hydrogen sulphate	Generator
O-Cresol hydrogen sulphuric acid	Generator
2-Methylphenyl hydrogen sulfate	HMDB
2-Methylphenyl hydrogen sulphate	HMDB

Chemical Formula

C₇H₈O₄S

Average Molecular Weight

188.2

Monoisotopic Molecular Weight

188.014329912

IUPAC Name

(2-methylphenyl)oxidanesulfonic acid

Traditional Name

(2-methylphenyl)oxidanesulfonic acid

CAS Registry Number

3233-56-5

SMILES

CC1=C(OS(O)(=O)=O)C=CC=C1

InChI Identifier

InChI=1S/C7H8O4S/c1-6-4-2-3-5-7(6)11-12(8,9)10/h2-5H,1H3,(H,8,9,10)

InChI Key

CYGSXDXRHXMAOV-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
Toluene
Benzenoid
Sulfuric acid ester
Sulfate-ester
Sulfuric acid monoester
Monocyclic benzene moiety
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Urine (PMID: 30087103)

Source

Exogenous

Exogenous (HMDB: HMDB0240655)

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	-0.59	ALOGPS
logP	1.71	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	-2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	63.6 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	43.07 m³·mol⁻¹	ChemAxon
Polarizability	16.9 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
DeepCCS	[M+H]+	137.973	30932474
DeepCCS	[M-H]-	135.405	30932474
DeepCCS	[M-2H]-	171.112	30932474
DeepCCS	[M+Na]+	146.509	30932474
AllCCS	[M+H]+	142.1	32859911
AllCCS	[M+H-H2O]+	138.0	32859911
AllCCS	[M+NH4]+	145.9	32859911
AllCCS	[M+Na]+	146.9	32859911
AllCCS	[M-H]-	132.8	32859911
AllCCS	[M+Na-2H]-	134.1	32859911
AllCCS	[M+HCOO]-	135.5	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.	5.19 minutes	32390414
Predicted by Siyang on May 30, 2022	12.6074 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.05 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1426.3 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	426.3 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	145.7 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	274.7 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	154.5 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	462.7 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	551.6 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	140.6 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1011.0 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	376.2 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	1227.4 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	283.9 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	342.5 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	456.2 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	252.0 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	120.4 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
o-Cresol sulfate	CC1=C(OS(O)(=O)=O)C=CC=C1	2503.4	Standard polar	33892256
o-Cresol sulfate	CC1=C(OS(O)(=O)=O)C=CC=C1	1444.9	Standard non polar	33892256
o-Cresol sulfate	CC1=C(OS(O)(=O)=O)C=CC=C1	1555.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
o-Cresol sulfate,1TMS,isomer #1	CC1=CC=CC=C1OS(=O)(=O)O[Si](C)(C)C	1548.0	Semi standard non polar	33892256
o-Cresol sulfate,1TMS,isomer #1	CC1=CC=CC=C1OS(=O)(=O)O[Si](C)(C)C	1603.7	Standard non polar	33892256
o-Cresol sulfate,1TMS,isomer #1	CC1=CC=CC=C1OS(=O)(=O)O[Si](C)(C)C	2199.7	Standard polar	33892256
o-Cresol sulfate,1TBDMS,isomer #1	CC1=CC=CC=C1OS(=O)(=O)O[Si](C)(C)C(C)(C)C	1794.3	Semi standard non polar	33892256
o-Cresol sulfate,1TBDMS,isomer #1	CC1=CC=CC=C1OS(=O)(=O)O[Si](C)(C)C(C)(C)C	1856.8	Standard non polar	33892256
o-Cresol sulfate,1TBDMS,isomer #1	CC1=CC=CC=C1OS(=O)(=O)O[Si](C)(C)C(C)(C)C	2276.9	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - o-Cresol sulfate GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - o-Cresol sulfate 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 - o-Cresol sulfate 10V, Positive-QTOF	splash10-0a4i-0900000000-5b86cd409e7bf5d7070a	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - o-Cresol sulfate 20V, Positive-QTOF	splash10-0a4i-3900000000-c0b146db029d66a4bc2e	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - o-Cresol sulfate 40V, Positive-QTOF	splash10-0006-9000000000-bdf3506bcc069c342ef2	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - o-Cresol sulfate 10V, Negative-QTOF	splash10-000i-0900000000-1a8286d1aadcdc168ec6	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - o-Cresol sulfate 20V, Negative-QTOF	splash10-000i-1900000000-20723eeed1f29e367328	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - o-Cresol sulfate 40V, Negative-QTOF	splash10-001j-9600000000-ebcff4f07340b33c1d25	2021-09-25	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	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
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	30087103	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

9790277

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

133089

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

Mair RD, Sirich TL, Plummer NS, Meyer TW: Characteristics of Colon-Derived Uremic Solutes. Clin J Am Soc Nephrol. 2018 Sep 7;13(9):1398-1404. doi: 10.2215/CJN.03150318. Epub 2018 Aug 7. [PubMed:30087103 ]

Showing metabocard for o-Cresol sulfate (HMDB0240655)

MOL for HMDB0240655 (o-Cresol sulfate)

3D MOL for HMDB0240655 (o-Cresol sulfate)

3D SDF for HMDB0240655 (o-Cresol sulfate)

3D-SDF for HMDB0240655 (o-Cresol sulfate)

PDB for HMDB0240655 (o-Cresol sulfate)

3D PDB for HMDB0240655 (o-Cresol sulfate)

SMILES for HMDB0240655 (o-Cresol sulfate)

INCHI for HMDB0240655 (o-Cresol sulfate)

Structure for HMDB0240655 (o-Cresol sulfate)

3D Structure for HMDB0240655 (o-Cresol sulfate)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra