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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2022-09-09 21:07:23 UTC

Update Date

2022-09-22 18:35:15 UTC

HMDB ID

HMDB0341427

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Sinapinic acid O-sulfate

Description

sulfo (2E)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enoate belongs to the class of organic compounds known as coumaric acids and derivatives. These are aromatic compounds containing Aromatic compounds containing a cinnamic acid moiety (or a derivative thereof) hydroxylated at the C2 (ortho-), C3 (meta-), or C4 (para-) carbon atom of the benzene ring. sulfo (2E)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enoate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI

Sinapinic acid
  Mrv1652310091814192D          

 20 20  0  0  0  0            999 V2000
    0.0000    2.4749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2374    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4749    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2374    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.8250    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.8403   -0.1339    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7555   -1.5607    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0448   -0.2669    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  2  0  0  0  0
  5 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 12 15  2  0  0  0  0
  3 15  1  0  0  0  0
 15 16  1  0  0  0  0
 17  9  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  2  0  0  0  0
 17 20  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0341427

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=CC(\C=C\C(=O)OS(O)(=O)=O)=CC(OC)=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C11H12O8S/c1-17-8-5-7(6-9(18-2)11(8)13)3-4-10(12)19-20(14,15)16/h3-6,13H,1-2H3,(H,14,15,16)/b4-3+

> <INCHI_KEY>
LAHUBJBDDCZJTK-ONEGZZNKSA-N

> <FORMULA>
C11H12O8S

> <MOLECULAR_WEIGHT>
304.273

> <EXACT_MASS>
304.02528805

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
32

> <JCHEM_AVERAGE_POLARIZABILITY>
28.01876447406375

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
sulfo (2E)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enoate

> <ALOGPS_LOGP>
0.18

> <JCHEM_LOGP>
1.2751983939999998

> <ALOGPS_LOGS>
-3.02

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.286963638602263

> <JCHEM_PKA_STRONGEST_ACIDIC>
-2.490030926511328

> <JCHEM_PKA_STRONGEST_BASIC>
-4.607270779053683

> <JCHEM_POLAR_SURFACE_AREA>
119.36

> <JCHEM_REFRACTIVITY>
68.2458

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.93e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
sulfo (2E)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 09-OCT-18   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: Sinapinic acid                                    
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-OCT-18         0                                  
HETATM    1  C   UNK     0       0.000   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       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       6.668  -2.310   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0       5.335  -4.620   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -2.667   0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
HETATM   17  S   UNK     0       8.002  -1.540   0.000  0.00  0.00           S+0
HETATM   18  O   UNK     0       7.169  -0.250   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       8.877  -2.913   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       9.417  -0.498   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   15                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   11                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8   17                                                       
CONECT   10    8                                                            
CONECT   11    5   12                                                       
CONECT   12   11   13   15                                                  
CONECT   13   12   14                                                       
CONECT   14   13                                                            
CONECT   15   12    3   16                                                  
CONECT   16   15                                                            
CONECT   17    9   18   19   20                                             
CONECT   18   17                                                            
CONECT   19   17                                                            
CONECT   20   17                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   40    0
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
SulfO (2E)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enoic acid	Generator
SulphO (2E)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enoate	Generator
SulphO (2E)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enoic acid	Generator
Sinapinate-O-sulfate	Generator
Sinapinate-O-sulphate	Generator
Sinapinic acid-O-sulfuric acid	Generator
Sinapinic acid-O-sulphuric acid	Generator

Chemical Formula

C₁₁H₁₂O₈S

Average Molecular Weight

304.273

Monoisotopic Molecular Weight

304.02528805

IUPAC Name

sulfo (2E)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enoate

Traditional Name

sulfo (2E)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enoate

CAS Registry Number

Not Available

SMILES

COC1=CC(\C=C\C(=O)OS(O)(=O)=O)=CC(OC)=C1O

InChI Identifier

InChI=1S/C11H12O8S/c1-17-8-5-7(6-9(18-2)11(8)13)3-4-10(12)19-20(14,15)16/h3-6,13H,1-2H3,(H,14,15,16)/b4-3+

InChI Key

LAHUBJBDDCZJTK-ONEGZZNKSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as coumaric acids and derivatives. These are aromatic compounds containing Aromatic compounds containing a cinnamic acid moiety (or a derivative thereof) hydroxylated at the C2 (ortho-), C3 (meta-), or C4 (para-) carbon atom of the benzene ring.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Cinnamic acids and derivatives

Sub Class

Hydroxycinnamic acids and derivatives

Direct Parent

Coumaric acids and derivatives

Alternative Parents

Substituents

Coumaric acid or derivatives
M-dimethoxybenzene
Dimethoxybenzene
Methoxyphenol
Phenoxy compound
Anisole
Methoxybenzene
Styrene
Phenol ether
Alkyl aryl ether
Phenol
Monocyclic benzene moiety
Benzenoid
Sulfuric acid ester
Sulfuric acid monoester
Organic sulfuric acid or derivatives
Carboxylic acid salt
Ether
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Organooxygen compound
Organic salt
Organic oxygen compound
Carbonyl group
Hydrocarbon derivative
Organic oxide
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

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	0.18	ALOGPS
logP	1.28	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	-2.5	ChemAxon
pKa (Strongest Basic)	-4.6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	119.36 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	68.25 m³·mol⁻¹	ChemAxon
Polarizability	28.02 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 Retention Times

Not Available

Predicted Kovats Retention Indices

Not Available

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Sinapinic acid O-sulfate GC-MS (Non-derivatized) - 70eV, Positive	splash10-05i0-2691000000-aa3d3c35082dbc4d0c93	2017-07-27	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Sinapinic acid O-sulfate GC-MS (1 TMS) - 70eV, Positive	splash10-0h90-3095000000-3deb1ba89f50f97709b4	2017-10-06	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 - Sinapinic acid O-sulfate 10V, Positive-QTOF	splash10-052r-0191000000-efca3a9a9df3efe4b051	2017-06-28	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sinapinic acid O-sulfate 20V, Positive-QTOF	splash10-0a4i-2390000000-ddf6c18eb8ebaef1c1d7	2017-06-28	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sinapinic acid O-sulfate 40V, Positive-QTOF	splash10-06vj-0910000000-a957e31b894474febf59	2017-06-28	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sinapinic acid O-sulfate 10V, Negative-QTOF	splash10-0udi-1039000000-ba484cfe6e6c263bfdf3	2017-06-28	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sinapinic acid O-sulfate 20V, Negative-QTOF	splash10-0pi0-2192000000-bceb8720c7babd530b63	2017-06-28	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sinapinic acid O-sulfate 40V, Negative-QTOF	splash10-001i-9550000000-1581490a8c129d2b2da0	2017-06-28	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

Not Available

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Asthma	33739820	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Asthma	33739820	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

124202101

PDB ID

Not Available

ChEBI ID

89552

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

Meister I, Zhang P, Sinha A, Skold CM, Wheelock AM, Izumi T, Chaleckis R, Wheelock CE: High-Precision Automated Workflow for Urinary Untargeted Metabolomic Epidemiology. Anal Chem. 2021 Mar 30;93(12):5248-5258. doi: 10.1021/acs.analchem.1c00203. Epub 2021 Mar 19. [PubMed:33739820 ]

Showing metabocard for Sinapinic acid O-sulfate (HMDB0341427)

MOL for HMDB0341427 (Sinapinic acid O-sulfate)

3D MOL for HMDB0341427 (Sinapinic acid O-sulfate)

3D SDF for HMDB0341427 (Sinapinic acid O-sulfate)

3D-SDF for HMDB0341427 (Sinapinic acid O-sulfate)

PDB for HMDB0341427 (Sinapinic acid O-sulfate)

3D PDB for HMDB0341427 (Sinapinic acid O-sulfate)

SMILES for HMDB0341427 (Sinapinic acid O-sulfate)

INCHI for HMDB0341427 (Sinapinic acid O-sulfate)

Structure for HMDB0341427 (Sinapinic acid O-sulfate)

3D Structure for HMDB0341427 (Sinapinic acid O-sulfate)

Predicted Retention Times

Predicted Kovats Retention Indices

GC-MS Spectra

MS/MS Spectra