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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2019-10-11 16:20:39 UTC

Update Date

2022-03-07 03:18:19 UTC

HMDB ID

HMDB0240549

Secondary Accession Numbers

None

Metabolite Identification

Common Name

O-Coumaric acid sulfate

Description

O-Coumaric acid sulfate, also known as O-coumarate sulfate, belongs to the class of organic compounds known as coumaric acids. These are aromatic compounds containing a cinnamic acid moiety hydroxylated at the C2 (ortho-), C3 (meta-), or C4 (para-) carbon atom of the benzene ring. Based on a literature review very few articles have been published on O-Coumaric acid sulfate.

Structure

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

  Mrv1652310111918202D          

 16 16  0  0  0  0            999 V2000
    0.7145   -0.4125    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
   -0.0000    0.0000    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
   -0.7145    1.2375    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
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    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 O   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
    0.4125    3.1895    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125    1.7605    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.8875    0.0000 O   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
    0.0000    2.4750    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  6  5  2  0  0  0  0
  7  3  2  0  0  0  0
  7  5  1  0  0  0  0
  8  4  2  0  0  0  0
  8  7  1  0  0  0  0
  6  9  1  4  0  0  0
 10  9  2  0  0  0  0
 11  9  1  0  0  0  0
 15  8  1  0  0  0  0
 16 12  1  0  0  0  0
 16 13  2  0  0  0  0
 16 14  2  0  0  0  0
 16 15  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0240549

> <DATABASE_NAME>
hmdb

> <SMILES>
OC(=O)C=CC1=CC=CC=C1OS(O)(=O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C9H8O6S/c10-9(11)6-5-7-3-1-2-4-8(7)15-16(12,13)14/h1-6H,(H,10,11)(H,12,13,14)

> <INCHI_KEY>
BTRJLVGUHCECAH-UHFFFAOYSA-N

> <FORMULA>
C9H8O6S

> <MOLECULAR_WEIGHT>
244.22

> <EXACT_MASS>
244.004159152

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
24

> <JCHEM_AVERAGE_POLARIZABILITY>
21.302138102119038

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-[2-(sulfooxy)phenyl]prop-2-enoic acid

> <ALOGPS_LOGP>
-0.47

> <JCHEM_LOGP>
1.357207592

> <ALOGPS_LOGS>
-2.65

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
3.529940175621069

> <JCHEM_PKA_STRONGEST_ACIDIC>
-2.1304646108447995

> <JCHEM_POLAR_SURFACE_AREA>
100.89999999999999

> <JCHEM_REFRACTIVITY>
55.03260000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.41e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-[2-(sulfooxy)phenyl]prop-2-enoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 11-OCT-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-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      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.667   0.000   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -4.001  -0.770   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       0.770   5.954   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      -0.770   3.286   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0      -1.334   5.390   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
HETATM   16  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    7                                                       
CONECT    4    2    8                                                       
CONECT    5    6    7                                                       
CONECT    6    5    9                                                       
CONECT    7    3    5    8                                                  
CONECT    8    4    7   15                                                  
CONECT    9    6   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9                                                            
CONECT   12   16                                                            
CONECT   13   16                                                            
CONECT   14   16                                                            
CONECT   15    8   16                                                       
CONECT   16   12   13   14   15                                             
MASTER        0    0    0    0    0    0    0    0   16    0   32    0
END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
O-Coumarate sulfate	Generator
O-Coumarate sulphate	Generator
O-Coumaric acid sulfuric acid	Generator
O-Coumaric acid sulphuric acid	Generator
3-[2-(Sulfooxy)phenyl]prop-2-enoate	HMDB
3-[2-(Sulphooxy)phenyl]prop-2-enoate	HMDB
3-[2-(Sulphooxy)phenyl]prop-2-enoic acid	HMDB

Chemical Formula

C₉H₈O₆S

Average Molecular Weight

244.22

Monoisotopic Molecular Weight

244.004159152

IUPAC Name

3-[2-(sulfooxy)phenyl]prop-2-enoic acid

Traditional Name

3-[2-(sulfooxy)phenyl]prop-2-enoic acid

CAS Registry Number

Not Available

SMILES

OC(=O)C=CC1=CC=CC=C1OS(O)(=O)=O

InChI Identifier

InChI=1S/C9H8O6S/c10-9(11)6-5-7-3-1-2-4-8(7)15-16(12,13)14/h1-6H,(H,10,11)(H,12,13,14)

InChI Key

BTRJLVGUHCECAH-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as coumaric acids. These are aromatic compounds containing a cinnamic acid moiety 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

Alternative Parents

Substituents

Cinnamic acid
Coumaric acid
Phenylsulfate
Arylsulfate
Styrene
Phenoxy compound
Monocyclic benzene moiety
Benzenoid
Sulfuric acid ester
Sulfate-ester
Sulfuric acid monoester
Organic sulfuric acid or derivatives
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
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: 32966057)

Excreta

Biofluid or Excreta

Urine (PMID: 32966057)

Source

Exogenous

Exogenous (HMDB: HMDB0240549)

Food

Cocoa and cocoa product

Cocoa and cocoa products (HMDB: HMDB0240549)

Coffee and coffee product

Coffee product

Coffee products (HMDB: HMDB0240549)

Tea

Tea products (HMDB: HMDB0240549)

Fat and oil

Olive oil (HMDB: HMDB0240549)

Fruit

Fruits (HMDB: HMDB0240549)

Vegetable

Vegetables (HMDB: HMDB0240549)

Legumes (HMDB: HMDB0240549)

Cereal and cereal product

Cereal product

Whole grain cereal products (HMDB: HMDB0240549)

Nut

Nuts (HMDB: HMDB0240549)

Beverage

Alcoholic beverage

Red wine (HMDB: HMDB0240549)

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	-0.47	ALOGPS
logP	1.36	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	-2.1	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	100.9 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	55.03 m³·mol⁻¹	ChemAxon
Polarizability	21.3 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]+	144.206	30932474
DeepCCS	[M-H]-	141.73	30932474
DeepCCS	[M-2H]-	177.234	30932474
DeepCCS	[M+Na]+	152.772	30932474
AllCCS	[M+H]+	152.1	32859911
AllCCS	[M+H-H2O]+	148.5	32859911
AllCCS	[M+NH4]+	155.5	32859911
AllCCS	[M+Na]+	156.5	32859911
AllCCS	[M-H]-	145.4	32859911
AllCCS	[M+Na-2H]-	145.7	32859911
AllCCS	[M+HCOO]-	146.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
O-Coumaric acid sulfate	OC(=O)C=CC1=CC=CC=C1OS(O)(=O)=O	3987.3	Standard polar	33892256
O-Coumaric acid sulfate	OC(=O)C=CC1=CC=CC=C1OS(O)(=O)=O	1839.5	Standard non polar	33892256
O-Coumaric acid sulfate	OC(=O)C=CC1=CC=CC=C1OS(O)(=O)=O	2202.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
O-Coumaric acid sulfate,1TMS,isomer #1	C[Si](C)(C)OC(=O)C=CC1=CC=CC=C1OS(=O)(=O)O	2207.2	Semi standard non polar	33892256
O-Coumaric acid sulfate,1TMS,isomer #2	C[Si](C)(C)OS(=O)(=O)OC1=CC=CC=C1C=CC(=O)O	2222.3	Semi standard non polar	33892256
O-Coumaric acid sulfate,2TMS,isomer #1	C[Si](C)(C)OC(=O)C=CC1=CC=CC=C1OS(=O)(=O)O[Si](C)(C)C	2190.5	Semi standard non polar	33892256
O-Coumaric acid sulfate,2TMS,isomer #1	C[Si](C)(C)OC(=O)C=CC1=CC=CC=C1OS(=O)(=O)O[Si](C)(C)C	2252.2	Standard non polar	33892256
O-Coumaric acid sulfate,2TMS,isomer #1	C[Si](C)(C)OC(=O)C=CC1=CC=CC=C1OS(=O)(=O)O[Si](C)(C)C	2909.4	Standard polar	33892256
O-Coumaric acid sulfate,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C=CC1=CC=CC=C1OS(=O)(=O)O	2462.0	Semi standard non polar	33892256
O-Coumaric acid sulfate,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OS(=O)(=O)OC1=CC=CC=C1C=CC(=O)O	2469.4	Semi standard non polar	33892256
O-Coumaric acid sulfate,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C=CC1=CC=CC=C1OS(=O)(=O)O[Si](C)(C)C(C)(C)C	2692.2	Semi standard non polar	33892256
O-Coumaric acid sulfate,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C=CC1=CC=CC=C1OS(=O)(=O)O[Si](C)(C)C(C)(C)C	2780.6	Standard non polar	33892256
O-Coumaric acid sulfate,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C=CC1=CC=CC=C1OS(=O)(=O)O[Si](C)(C)C(C)(C)C	2990.6	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - O-Coumaric acid 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-Coumaric acid sulfate 10V, Negative-QTOF	splash10-00dl-0090000000-3e667f65c6481e8e3793	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - O-Coumaric acid sulfate 20V, Negative-QTOF	splash10-006w-5890000000-70ea7f5dc8f9e840b316	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - O-Coumaric acid sulfate 40V, Negative-QTOF	splash10-0002-9600000000-e1c22570bfac52af2019	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - O-Coumaric acid sulfate 10V, Positive-QTOF	splash10-0002-0190000000-d040408aaa2bfdd003af	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - O-Coumaric acid sulfate 20V, Positive-QTOF	splash10-00kb-0920000000-2e8038fd330ed150d269	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - O-Coumaric acid sulfate 40V, Positive-QTOF	splash10-0gb9-3900000000-ae81a8d5fe067b59f55d	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, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
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, 1000 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, 200 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, 300 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, 400 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, 500 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, 600 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, 700 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, 800 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, 900 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

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

FDB093744

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

59950526

PDB ID

Not Available

ChEBI ID

Not Available

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

Not Available

Showing metabocard for O-Coumaric acid sulfate (HMDB0240549)

MOL for HMDB0240549 (O-Coumaric acid sulfate)

3D MOL for HMDB0240549 (O-Coumaric acid sulfate)

3D SDF for HMDB0240549 (O-Coumaric acid sulfate)

3D-SDF for HMDB0240549 (O-Coumaric acid sulfate)

PDB for HMDB0240549 (O-Coumaric acid sulfate)

3D PDB for HMDB0240549 (O-Coumaric acid sulfate)

SMILES for HMDB0240549 (O-Coumaric acid sulfate)

INCHI for HMDB0240549 (O-Coumaric acid sulfate)

Structure for HMDB0240549 (O-Coumaric acid sulfate)

3D Structure for HMDB0240549 (O-Coumaric acid sulfate)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra