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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2017-10-09 16:34:23 UTC

Update Date

2022-09-22 17:44:14 UTC

HMDB ID

HMDB0170765

Secondary Accession Numbers

None

Metabolite Identification

Common Name

4-Allylphenol sulfate

Description

4-Allylphenol sulfate, also known as chavicol sulfate or chavicol 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. Based on a literature review a significant number of articles have been published on 4-Allylphenol sulfate.

Structure

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

  Mrv1652306032021572D          

 14 14  0  0  0  0            999 V2000
 9998.5936 9999.1520    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9997.8795 9999.5653    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
 9997.466310000.2785    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.290810000.2785    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9997.1614 9999.1499    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.450010000.8000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.163210000.3898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.878510000.8000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.736510000.3896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.022110000.8020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.307510000.3895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.3075 9999.5645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.0220 9999.1520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.7365 9999.5645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  2  0  0  0  0
  2  5  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14  9  1  0  0  0  0
  1 12  1  0  0  0  0
  9  6  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0170765

> <DATABASE_NAME>
hmdb

> <SMILES>
OS(=O)(=O)OC1=CC=C(CC=C)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C9H10O4S/c1-2-3-8-4-6-9(7-5-8)13-14(10,11)12/h2,4-7H,1,3H2,(H,10,11,12)

> <INCHI_KEY>
KFDHKOFCRYUXLA-UHFFFAOYSA-N

> <FORMULA>
C9H10O4S

> <MOLECULAR_WEIGHT>
214.24

> <EXACT_MASS>
214.029979976

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
24

> <JCHEM_AVERAGE_POLARIZABILITY>
20.30370112243623

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
[4-(prop-2-en-1-yl)phenyl]oxidanesulfonic acid

> <ALOGPS_LOGP>
0.11

> <JCHEM_LOGP>
2.292937881

> <ALOGPS_LOGS>
-2.59

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
-1.8963618921446104

> <JCHEM_POLAR_SURFACE_AREA>
63.60000000000001

> <JCHEM_REFRACTIVITY>
52.318

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.52e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[4-(prop-2-en-1-yl)phenyl]oxidanesulfonic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 03-JUN-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-JUN-20         0                                  
HETATM    1  O   UNK     0    8664.0418665.084   0.000  0.00  0.00           O+0
HETATM    2  S   UNK     0    8662.7088665.855   0.000  0.00  0.00           S+0
HETATM    3  O   UNK     0    8661.9378667.187   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0    8663.4768667.187   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0    8661.3688665.080   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0    8669.3738668.160   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    8670.7058667.394   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8672.0408668.160   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8668.0418667.394   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8666.7088668.164   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8665.3748667.394   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8665.3748665.854   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8666.7088665.084   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8668.0418665.854   0.000  0.00  0.00           C+0
CONECT    1    2   12                                                       
CONECT    2    1    3    4    5                                             
CONECT    3    2                                                            
CONECT    4    2                                                            
CONECT    5    2                                                            
CONECT    6    7    9                                                       
CONECT    7    6    8                                                       
CONECT    8    7                                                            
CONECT    9   10   14    6                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13    1                                                  
CONECT   13   12   14                                                       
CONECT   14   13    9                                                       
MASTER        0    0    0    0    0    0    0    0   14    0   28    0
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
4-Allylphenyl hydrogen sulfate	ChEBI
Chavicol sulfate	ChEBI
p-Allylphenyl hydrogen sulfate	ChEBI
p-Allylphenyl sulfate	ChEBI
4-Allylphenyl hydrogen sulfuric acid	Generator
4-Allylphenyl hydrogen sulphate	Generator
4-Allylphenyl hydrogen sulphuric acid	Generator
Chavicol sulfuric acid	Generator
Chavicol sulphate	Generator
Chavicol sulphuric acid	Generator
p-Allylphenyl hydrogen sulfuric acid	Generator
p-Allylphenyl hydrogen sulphate	Generator
p-Allylphenyl hydrogen sulphuric acid	Generator
p-Allylphenyl sulfuric acid	Generator
p-Allylphenyl sulphate	Generator
p-Allylphenyl sulphuric acid	Generator
4-Allylphenol sulfuric acid	Generator
4-Allylphenol sulphate	Generator
4-Allylphenol sulphuric acid	Generator
Chavicol hydrogen sulfuric acid	HMDB
Chavicol hydrogen sulphate	HMDB
Chavicol hydrogen sulphuric acid	HMDB
4-Allylphenolsulfate	HMDB
4-Allylphenolsulphate	HMDB
4-Allylphenol sulfate	ChEBI

Chemical Formula

C₉H₁₀O₄S

Average Molecular Weight

214.24

Monoisotopic Molecular Weight

214.029979976

IUPAC Name

[4-(prop-2-en-1-yl)phenyl]oxidanesulfonic acid

Traditional Name

[4-(prop-2-en-1-yl)phenyl]oxidanesulfonic acid

CAS Registry Number

1823179-01-6

SMILES

OS(=O)(=O)OC1=CC=C(CC=C)C=C1

InChI Identifier

InChI=1S/C9H10O4S/c1-2-3-8-4-6-9(7-5-8)13-14(10,11)12/h2,4-7H,1,3H2,(H,10,11,12)

InChI Key

KFDHKOFCRYUXLA-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
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

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 26561314)

Source

Exogenous

Exogenous (HMDB: HMDB0170765)

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	0.11	ALOGPS
logP	2.29	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	-1.9	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	4	ChemAxon
Refractivity	52.32 m³·mol⁻¹	ChemAxon
Polarizability	20.3 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]+	141.975	30932474
DeepCCS	[M-H]-	139.58	30932474
DeepCCS	[M-2H]-	173.194	30932474
DeepCCS	[M+Na]+	147.912	30932474
AllCCS	[M+H]+	147.5	32859911
AllCCS	[M+H-H2O]+	143.6	32859911
AllCCS	[M+NH4]+	151.2	32859911
AllCCS	[M+Na]+	152.2	32859911
AllCCS	[M-H]-	142.6	32859911
AllCCS	[M+Na-2H]-	143.3	32859911
AllCCS	[M+HCOO]-	144.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
4-Allylphenol sulfate	OS(=O)(=O)OC1=CC=C(CC=C)C=C1	2704.9	Standard polar	33892256
4-Allylphenol sulfate	OS(=O)(=O)OC1=CC=C(CC=C)C=C1	1617.7	Standard non polar	33892256
4-Allylphenol sulfate	OS(=O)(=O)OC1=CC=C(CC=C)C=C1	1740.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
4-Allylphenol sulfate,1TMS,isomer #1	C=CCC1=CC=C(OS(=O)(=O)O[Si](C)(C)C)C=C1	1758.3	Semi standard non polar	33892256
4-Allylphenol sulfate,1TMS,isomer #1	C=CCC1=CC=C(OS(=O)(=O)O[Si](C)(C)C)C=C1	1765.7	Standard non polar	33892256
4-Allylphenol sulfate,1TMS,isomer #1	C=CCC1=CC=C(OS(=O)(=O)O[Si](C)(C)C)C=C1	2508.6	Standard polar	33892256
4-Allylphenol sulfate,1TBDMS,isomer #1	C=CCC1=CC=C(OS(=O)(=O)O[Si](C)(C)C(C)(C)C)C=C1	2013.8	Semi standard non polar	33892256
4-Allylphenol sulfate,1TBDMS,isomer #1	C=CCC1=CC=C(OS(=O)(=O)O[Si](C)(C)C(C)(C)C)C=C1	2016.4	Standard non polar	33892256
4-Allylphenol sulfate,1TBDMS,isomer #1	C=CCC1=CC=C(OS(=O)(=O)O[Si](C)(C)C(C)(C)C)C=C1	2587.7	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Allylphenol sulfate GC-MS (Non-derivatized) - 70eV, Positive	splash10-001i-2900000000-129b8416aca9f5d16c6a	2018-04-09	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Allylphenol sulfate GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Allylphenol 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 - 4-Allylphenol sulfate 10V, Positive-QTOF	splash10-014i-0490000000-f17fa2140439c2dbe68d	2018-04-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Allylphenol sulfate 20V, Positive-QTOF	splash10-014s-1910000000-af03a1a539388ea031e8	2018-04-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Allylphenol sulfate 40V, Positive-QTOF	splash10-0j4u-9400000000-22770cf4e3fc5731637c	2018-04-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Allylphenol sulfate 10V, Negative-QTOF	splash10-03di-0190000000-b234ed69ba248360dcb0	2018-04-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Allylphenol sulfate 20V, Negative-QTOF	splash10-001i-0920000000-b15f6c5a847cfc9dba05	2018-04-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Allylphenol sulfate 40V, Negative-QTOF	splash10-001i-3900000000-0110df733c9fbd963e09	2018-04-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Allylphenol sulfate 10V, Positive-QTOF	splash10-014i-0190000000-6b726a3d279b0b1c58b3	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Allylphenol sulfate 20V, Positive-QTOF	splash10-014i-6910000000-1773afcc627c54a527dd	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Allylphenol sulfate 40V, Positive-QTOF	splash10-016r-9300000000-446a31780b3861cb95c2	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Allylphenol sulfate 10V, Negative-QTOF	splash10-03di-0090000000-89e8ea66f7a2531ed081	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Allylphenol sulfate 20V, Negative-QTOF	splash10-03di-3090000000-e43cb2a90ce51c97c219	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Allylphenol sulfate 40V, Negative-QTOF	splash10-00ls-9000000000-f25eddd5f8e4562b37bf	2021-09-24	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	2022-08-20	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	Adult (>18 years old)	Male	Normal	26561314	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Urine	Detected 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

58170353

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

66633409

PDB ID

Not Available

ChEBI ID

133096

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

Nieman DC, Gillitt ND, Sha W, Meaney MP, John C, Pappan KL, Kinchen JM: Metabolomics-Based Analysis of Banana and Pear Ingestion on Exercise Performance and Recovery. J Proteome Res. 2015 Dec 4;14(12):5367-77. doi: 10.1021/acs.jproteome.5b00909. Epub 2015 Nov 23. [PubMed:26561314 ]

Showing metabocard for 4-Allylphenol sulfate (HMDB0170765)

MOL for HMDB0170765 (4-Allylphenol sulfate)

3D MOL for HMDB0170765 (4-Allylphenol sulfate)

3D SDF for HMDB0170765 (4-Allylphenol sulfate)

3D-SDF for HMDB0170765 (4-Allylphenol sulfate)

PDB for HMDB0170765 (4-Allylphenol sulfate)

3D PDB for HMDB0170765 (4-Allylphenol sulfate)

SMILES for HMDB0170765 (4-Allylphenol sulfate)

INCHI for HMDB0170765 (4-Allylphenol sulfate)

Structure for HMDB0170765 (4-Allylphenol sulfate)

3D Structure for HMDB0170765 (4-Allylphenol sulfate)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra