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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2013-07-22 15:50:11 UTC

Update Date

2023-02-21 17:30:20 UTC

HMDB ID

HMDB0061116

Secondary Accession Numbers

HMDB61116

Metabolite Identification

Common Name

2-aminophenol sulphate

Description

2-aminophenol sulphate belongs to the class of organic compounds known as phenylsulfates. Phenylsulfates are compounds containing a sulfuric acid group conjugated to a phenyl group. 2-aminophenol sulphate is a moderately basic compound (based on its pKa).

Structure

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

HEADER    PROTEIN                                 15-OCT-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   15-OCT-19         0                                  
HETATM    1  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.000   0.000   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       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0      -1.334   2.310   0.000  0.00  0.00           N+0
HETATM    8  O   UNK     0      -1.334   5.390   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0       0.770   5.954   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0      -0.770   3.286   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
HETATM   12  S   UNK     0       0.000   4.620   0.000  0.00  0.00           S+0
CONECT    1    2    3                                                       
CONECT    2    1    4                                                       
CONECT    3    1    5                                                       
CONECT    4    2    6                                                       
CONECT    5    3    6    7                                                  
CONECT    6    4    5   11                                                  
CONECT    7    5                                                            
CONECT    8   12                                                            
CONECT    9   12                                                            
CONECT   10   12                                                            
CONECT   11    6   12                                                       
CONECT   12    8    9   10   11                                             
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-Aminophenyl)oxidanesulfonic acid	ChEBI
2-Aminophenol hydrogen sulfate	ChEBI
2-Aminophenol sulfate	ChEBI
2-Aminophenyl sulfate	ChEBI
O-Aminophenol hydrogen sulfate	ChEBI
O-Aminophenyl hydrogen sulfate	ChEBI
Sulfuric acid mono-(2-aminophenyl ester)	ChEBI
(2-Aminophenyl)oxidanesulfonate	Generator
(2-Aminophenyl)oxidanesulphonate	Generator
(2-Aminophenyl)oxidanesulphonic acid	Generator
2-Aminophenol hydrogen sulfuric acid	Generator
2-Aminophenol hydrogen sulphate	Generator
2-Aminophenol hydrogen sulphuric acid	Generator
2-Aminophenol sulfuric acid	Generator
2-Aminophenol sulphuric acid	Generator
2-Aminophenyl sulfuric acid	Generator
2-Aminophenyl sulphate	Generator
2-Aminophenyl sulphuric acid	Generator
O-Aminophenol hydrogen sulfuric acid	Generator
O-Aminophenol hydrogen sulphate	Generator
O-Aminophenol hydrogen sulphuric acid	Generator
O-Aminophenyl hydrogen sulfuric acid	Generator
O-Aminophenyl hydrogen sulphate	Generator
O-Aminophenyl hydrogen sulphuric acid	Generator
Sulfate mono-(2-aminophenyl ester)	Generator
Sulphate mono-(2-aminophenyl ester)	Generator
Sulphuric acid mono-(2-aminophenyl ester)	Generator
2-Aminophenyl hydrogen sulfuric acid	HMDB
2-Aminophenyl hydrogen sulphate	HMDB
2-Aminophenyl hydrogen sulphuric acid	HMDB
2-Aminophenol sulphate	Generator

Chemical Formula

C₆H₇NO₄S

Average Molecular Weight

189.189

Monoisotopic Molecular Weight

189.009578407

IUPAC Name

(2-aminophenyl)oxidanesulfonic acid

Traditional Name

(2-aminophenyl)oxidanesulfonic acid

CAS Registry Number

Not Available

SMILES

NC1=CC=CC=C1OS(O)(=O)=O

InChI Identifier

InChI=1S/C6H7NO4S/c7-5-3-1-2-4-6(5)11-12(8,9)10/h1-4H,7H2,(H,8,9,10)

InChI Key

VSTZVCJQGSLNLL-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
Aniline or substituted anilines
Monocyclic benzene moiety
Sulfuric acid monoester
Sulfate-ester
Sulfuric acid ester
Benzenoid
Amine
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Primary amine
Organic oxygen compound
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 32966057)

Excreta

Biofluid or Excreta

Urine (PMID: 32966057)

Source

Endogenous

Endogenous (HMDB: HMDB0061116)

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	5.6 g/L	ALOGPS
logP	-1.3	ALOGPS
logP	0.14	ChemAxon
logS	-1.5	ALOGPS
pKa (Strongest Acidic)	-2.9	ChemAxon
pKa (Strongest Basic)	2.51	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	89.62 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	42.73 m³·mol⁻¹	ChemAxon
Polarizability	16.22 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]+	139.288	31661259
DarkChem	[M-H]-	135.927	31661259
DeepCCS	[M+H]+	132.481	30932474
DeepCCS	[M-H]-	128.652	30932474
DeepCCS	[M-2H]-	165.917	30932474
DeepCCS	[M+Na]+	141.457	30932474
AllCCS	[M+H]+	141.1	32859911
AllCCS	[M+H-H2O]+	136.8	32859911
AllCCS	[M+NH4]+	145.0	32859911
AllCCS	[M+Na]+	146.1	32859911
AllCCS	[M-H]-	132.5	32859911
AllCCS	[M+Na-2H]-	133.6	32859911
AllCCS	[M+HCOO]-	134.9	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.	3.38 minutes	32390414
Predicted by Siyang on May 30, 2022	10.9833 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	4.87 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1107.0 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	362.5 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	93.5 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	222.1 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	90.3 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	301.4 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	391.7 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	137.2 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	837.1 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	205.0 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	1011.2 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	230.2 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	269.0 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	457.2 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	230.0 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	153.4 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
2-aminophenol sulphate	NC1=CC=CC=C1OS(O)(=O)=O	3121.8	Standard polar	33892256
2-aminophenol sulphate	NC1=CC=CC=C1OS(O)(=O)=O	1712.0	Standard non polar	33892256
2-aminophenol sulphate	NC1=CC=CC=C1OS(O)(=O)=O	1737.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
2-aminophenol sulphate,1TMS,isomer #1	C[Si](C)(C)OS(=O)(=O)OC1=CC=CC=C1N	1748.2	Semi standard non polar	33892256
2-aminophenol sulphate,1TMS,isomer #1	C[Si](C)(C)OS(=O)(=O)OC1=CC=CC=C1N	1745.0	Standard non polar	33892256
2-aminophenol sulphate,1TMS,isomer #1	C[Si](C)(C)OS(=O)(=O)OC1=CC=CC=C1N	2964.3	Standard polar	33892256
2-aminophenol sulphate,1TMS,isomer #2	C[Si](C)(C)NC1=CC=CC=C1OS(=O)(=O)O	1852.6	Semi standard non polar	33892256
2-aminophenol sulphate,1TMS,isomer #2	C[Si](C)(C)NC1=CC=CC=C1OS(=O)(=O)O	1798.9	Standard non polar	33892256
2-aminophenol sulphate,1TMS,isomer #2	C[Si](C)(C)NC1=CC=CC=C1OS(=O)(=O)O	2693.4	Standard polar	33892256
2-aminophenol sulphate,2TMS,isomer #1	C[Si](C)(C)NC1=CC=CC=C1OS(=O)(=O)O[Si](C)(C)C	1852.6	Semi standard non polar	33892256
2-aminophenol sulphate,2TMS,isomer #1	C[Si](C)(C)NC1=CC=CC=C1OS(=O)(=O)O[Si](C)(C)C	1905.5	Standard non polar	33892256
2-aminophenol sulphate,2TMS,isomer #1	C[Si](C)(C)NC1=CC=CC=C1OS(=O)(=O)O[Si](C)(C)C	2432.9	Standard polar	33892256
2-aminophenol sulphate,2TMS,isomer #2	C[Si](C)(C)N(C1=CC=CC=C1OS(=O)(=O)O)[Si](C)(C)C	1882.8	Semi standard non polar	33892256
2-aminophenol sulphate,2TMS,isomer #2	C[Si](C)(C)N(C1=CC=CC=C1OS(=O)(=O)O)[Si](C)(C)C	1968.9	Standard non polar	33892256
2-aminophenol sulphate,2TMS,isomer #2	C[Si](C)(C)N(C1=CC=CC=C1OS(=O)(=O)O)[Si](C)(C)C	2503.2	Standard polar	33892256
2-aminophenol sulphate,3TMS,isomer #1	C[Si](C)(C)OS(=O)(=O)OC1=CC=CC=C1N([Si](C)(C)C)[Si](C)(C)C	1870.8	Semi standard non polar	33892256
2-aminophenol sulphate,3TMS,isomer #1	C[Si](C)(C)OS(=O)(=O)OC1=CC=CC=C1N([Si](C)(C)C)[Si](C)(C)C	2067.6	Standard non polar	33892256
2-aminophenol sulphate,3TMS,isomer #1	C[Si](C)(C)OS(=O)(=O)OC1=CC=CC=C1N([Si](C)(C)C)[Si](C)(C)C	2316.4	Standard polar	33892256
2-aminophenol sulphate,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OS(=O)(=O)OC1=CC=CC=C1N	2018.0	Semi standard non polar	33892256
2-aminophenol sulphate,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OS(=O)(=O)OC1=CC=CC=C1N	1999.5	Standard non polar	33892256
2-aminophenol sulphate,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OS(=O)(=O)OC1=CC=CC=C1N	2995.4	Standard polar	33892256
2-aminophenol sulphate,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NC1=CC=CC=C1OS(=O)(=O)O	2087.6	Semi standard non polar	33892256
2-aminophenol sulphate,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NC1=CC=CC=C1OS(=O)(=O)O	2032.8	Standard non polar	33892256
2-aminophenol sulphate,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NC1=CC=CC=C1OS(=O)(=O)O	2790.4	Standard polar	33892256
2-aminophenol sulphate,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC1=CC=CC=C1OS(=O)(=O)O[Si](C)(C)C(C)(C)C	2293.2	Semi standard non polar	33892256
2-aminophenol sulphate,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC1=CC=CC=C1OS(=O)(=O)O[Si](C)(C)C(C)(C)C	2416.6	Standard non polar	33892256
2-aminophenol sulphate,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC1=CC=CC=C1OS(=O)(=O)O[Si](C)(C)C(C)(C)C	2600.4	Standard polar	33892256
2-aminophenol sulphate,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N(C1=CC=CC=C1OS(=O)(=O)O)[Si](C)(C)C(C)(C)C	2338.2	Semi standard non polar	33892256
2-aminophenol sulphate,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N(C1=CC=CC=C1OS(=O)(=O)O)[Si](C)(C)C(C)(C)C	2431.4	Standard non polar	33892256
2-aminophenol sulphate,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N(C1=CC=CC=C1OS(=O)(=O)O)[Si](C)(C)C(C)(C)C	2617.4	Standard polar	33892256
2-aminophenol sulphate,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OS(=O)(=O)OC1=CC=CC=C1N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2513.2	Semi standard non polar	33892256
2-aminophenol sulphate,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OS(=O)(=O)OC1=CC=CC=C1N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2803.8	Standard non polar	33892256
2-aminophenol sulphate,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OS(=O)(=O)OC1=CC=CC=C1N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2555.7	Standard polar	33892256

Spectra

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	Adult (>18 years old)	Both	Normal	32966057	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	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

FDB093593

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

181670

PDB ID

Not Available

ChEBI ID

133186

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

Bondia-Pons I, Barri T, Hanhineva K, Juntunen K, Dragsted LO, Mykkanen H, Poutanen K: UPLC-QTOF/MS metabolic profiling unveils urinary changes in humans after a whole grain rye versus refined wheat bread intervention. Mol Nutr Food Res. 2013 Mar;57(3):412-22. doi: 10.1002/mnfr.201200571. Epub 2013 Jan 10. [PubMed:23307617 ]

Showing metabocard for 2-aminophenol sulphate (HMDB0061116)

MOL for HMDB0061116 (2-aminophenol sulphate)

3D MOL for HMDB0061116 (2-aminophenol sulphate)

3D SDF for HMDB0061116 (2-aminophenol sulphate)

3D-SDF for HMDB0061116 (2-aminophenol sulphate)

PDB for HMDB0061116 (2-aminophenol sulphate)

3D PDB for HMDB0061116 (2-aminophenol sulphate)

SMILES for HMDB0061116 (2-aminophenol sulphate)

INCHI for HMDB0061116 (2-aminophenol sulphate)

Structure for HMDB0061116 (2-aminophenol sulphate)

3D Structure for HMDB0061116 (2-aminophenol sulphate)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized